Slo-1 modulators for prevention and / or treatment of a disease
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- ELANCO ANIMAL HEALTH GMBH
- Filing Date
- 2025-10-09
- Publication Date
- 2026-05-15
AI Technical Summary
There is a pressing need for compounds with superior attributes in terms of activity and drug-ability profile to effectively prevent and/or treat parasitic infections, particularly endoparasitic infections, with a focus on long-lasting effects.
The use of quinoline-based compounds with specific structural variations, including alternatives A, A2, A3, A4, and A5, which incorporate various substituents such as halogens, alkyl groups, and heteroatoms, to enhance activity against helminths.
These compounds demonstrate enhanced activity and long-lasting effects in preventing and treating parasitic infections, particularly those caused by helminths, providing effective prevention and treatment solutions.
Abstract
Description
SLO-1 MODULATORS FOR PREVENTION AND / OR TREATMENT OF A DISEASEFIELD OF THE INVENTION
[0001] The present invention relates to quinoline-based compounds. The compounds of the invention are suitable for the prevention and / or treatment of a disease such as a helminthic infection. The compounds of the invention are in particular suitable for the long-term prevention and / or treatment of a disease. Further, the invention relates to a pharmaceutical composition which can also be used to prevent and / or treat a disease, in particular in longterm.BACKGROUND OF THE INVENTION
[0002] Parasitic infections in animals and humans are responsible for significant suffering. Specifically, endoparasitic infections and in particular helminthiases caused by nematodes including roundworms (such as heartworms (Dirofilaria immitis) and hookworms particularly Ancylostoma caninum) can inflict diseases through infection of, and damage to various organ systems, for example, the gastrointestinal tract, the lungs and the heart so that metabolic dysfunction, nutritional deficiencies, delayed growth, loss of productivity and death are caused.
[0003] Numerous classes of drugs are used to treat endoparasitic infections. Anthelminthic drugs are used to treat nematode infections in animals.
[0004] WO 2017 / 178416 Al concerns pyrazolopyrimidine compounds, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment, control and / or prevention of diseases, in particular of helminth infections, as a sole agent or in combination with other active ingredients.
[0005] WO 2018 / 087036 Al, WO 2019 / 025341 Al, and WO 2019 / 215182 Al relate to quinoline compounds, methods of preparing said compounds, intermediate compounds usefulfor preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment, control and / or prevention of diseases, in particular of helminth infections, as a sole agent or in combination with other active ingredients.
[0006] WO 2018 / 197401 Al covers bicyclic pyrazole compounds, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment, control and / or prevention of diseases, in particular of helminth infections, as a sole agent or in combination with other active ingredients.
[0007] WO 2019 / 002132 Al concerns azaquinoline compounds, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment, control and / or prevention of diseases, in particular of helminth infections, as a sole agent or in combination with other active ingredients.
[0008] WO 2020 / 083971 A2 relates to compounds, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for the treatment, control and / or prevention of diseases, in particular of helminth iufections, as a sole agent or in combination with other active ingredients.
[0009] WO 2021 / 204930 Al covers substituted condensed azines as anthelmintic compounds, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for the treatment, control and / or prevention of diseases, in particular of helminth infections, as a sole agent or in combination with other active ingredients.
[0010] WO 2020 / 131629 Al, WO 2020 / 131631 Al, WO 2020 / 247747 Al, WO 2022 / 106469A2 and WO 2022 / 117783 Al concern compounds which are useful in the control of endoparasites, for example heartworms, in warm-blooded animals.
[0011] WO 2021 / 018839 Al covers isoquinoline compounds, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment, control and / or prevention of diseases, in particular of helminth infections, as a sole agent or in combination with other active ingredients.
[0012] WO 2021 / 122906 Al, WO 2021 / 122911 Al, WO 2022 / 122987 Al and WO 2022 / 122988 Al relate to anthelmintic compounds. These compounds can, for example, be used in the treatment of the kind of worm disease caused by helminths such as Dirofilaria, in particular Dirofilaria immitis.
[0013] WO 2020 / 014068 Al concerns anthelminthic heterocyclic compounds and compositions comprising the same. A method of controlling helminths using these compounds is also described.
[0014] WO 2020 / 191091 Al relates to anthelmintic aza-benzotiophene and aza-benzofuran compounds and a method for the treatment, control or prevention of a parasitic infestation or infection in an animal in need thereof by administering an effective amount of these compounds to said animal.
[0015] WO 2021 / 242581 Al concerns anthelmintic heterocyclic compounds and a method for the treatment, control or prevention of a parasitic infestation or infection in an animal in need thereof by administering an effective amount of these compounds to said animal.
[0016] There is, however, still a pressing need for compounds with superior attributes in terms of activity and drug-ability profile to ensure effective prevention and / or treatment ofparasitic infections, especially endoparasitic infections. In particular, there is a need for compounds with long lasting effects against (endo)parasitic infectionsSUMMARY OF THE INVENTION
[0017] It is an object of the present invention to provide compounds with superior attributes, in particular in terms of activity, more particular in terms of long-lasting activity, to effectively prevent and / or treat a disease, in particular a disease caused by endoparasites such as helminths.
[0018] This problem is solved by the use of the compounds according to the claimed invention.
[0019] The invention concerns compounds of formula (I):according to alternative (i), (ii) (iii) or (iv), wherein according to alternative (i)A is AlA1 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Cs-Ce-halogenocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halog enoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl- CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R3 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, - SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, -NO2, -CONH2, -CH2-CONH2, -CHC=NCONH2, -COOH,Ci-C4-alkyl substituted with 1, 2 or 3 substituents selected from the group consisting of -CHO, -NO2, -SO2-Ci-C4-alkyl, and -SO-Ci-C4-alkyl,-Ci-C6-alkyl-C(=Li)-NH2wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L; is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and Ci-C4- alkoxy,Cs-Ce -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-C6-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH, 4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH, 4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains lor 2 heteratoms selected from the group consisting of O, N, and S, wherein the 4- to 6-membered heteroaryl is connected to the rest of the molecule via a carbon atom and wherein the 4- to 6- membered heteroaryl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Q is selected from the group consisting of a 5- or 6-membered aryl and 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; wherein according to alternative (ii)A is A2A2 wherein # indicates the connection to the rest of the molecule;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Cs-Ce-halogenocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halog enoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy,Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl- CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R3 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, - SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=N-SO2-(Ci-C4-alkyl), -CHC=NCONH2, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -N02, -NH2, -C0NH2, - CHO, =0 and -COOH;Rs hydrogen, halogen, -N02, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, and -CHO; s hydrogen, halogen, -N02, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, and -CHO;R7 hydrogen, halogen, -N02, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, and -CHO;Q is selected from the group consisting of a 5- or 6-membered aryl and 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SFs, and Ci-C4-alkyl, andwherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; according to alternative (iii)wherein # indicates the connection to the rest of the molecule;Y is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, -CHO, -CO-O-Ci-C4-alkyl, -NH(Ci-C4-alkyl), -S-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and -SO2-Ci-C4-alkyl;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Cs-Ce-halogenocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halog enoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl- CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1 -C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R3 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3-Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, - SC>2-Ci-C4-alkyl, and -SC>2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, halogen, cyano, -NO2, -NH2, -N(Ci-C4-alkyl)(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci-C4- alkoxy), -CONH2, -CH2-CONH2, -CHC=NCONH2, -OH, -CHO, -COOH,Ci-C4-alkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -OH, -CHO, -COOH, -NO2, -NH2, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci- C4-alkyl), -SO2-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and Ci-C4-alkoxy, Ci-C4-haloalkyl having 1 to 9 halogen atoms, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, cyano, Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, -OH, -NO2, -NH2, -CONH2, and -COOH, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from thegroup consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, and is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Q is selected from the group consisting of a 5- or 6-membered aryl and 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; wherein according to alternative (iv)A is A4A4 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Cs-Ce-halogenocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halog enoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl- CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R3 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, - SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=N-SO2-(Ci-C4-alkyl), -CHC=NCONH2,-Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl),-CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and Ci-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Q is selected from the group consisting of a 5- or 6-membered aryl and 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or wherein according to alternative (v) the compound is selected from the group consisting of8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(l-oxidothietan-3- yl) quinoline-3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-7- fluoroquinoline -3 -carboxamide ;7-bromo-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l- dioxidothietan-3 -yl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difhroro-5-(trifhioromethyl) phenyl)-4-(l,l-dioxidothietan-3-yl)-7- fluoroquinoline -3 -carboxamide ;7-chloro-8-(3-chloro-2-fhioro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l- dioxidothietan-3 -yl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)- 6, 7 -difluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difhroro-5-(trifhioromethyl) phenyl)-4-(l,l-dioxidothietan-3-yl)-6,7- difluoroquinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-7- (trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-6- fluoro-7-(trifluoromethyl) quinoline-3-carboxamide;(S)-8-(3-chloro-2-fhioro-5-(trifhioromethyl) phenyl)-N-(chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-6- (perfluoroethyl) quinoline -3 -carboxamide ;(S)-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-(chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-6- (perfluoropropyl) quino line-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-(2,3-dihydro-4H-benzo[b][l,4] oxazin-4-yl)-7- fluoro-4-(( lr,3r)-3-fluorocyclobutyl) quinoline -3 -carboxamide;4-((ls,3s)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-N-(2,3-dihydro-4H- benzo [b] [ 1 ,4] oxazin-4-yl) -7 -fluoroquinoline -3 -carboxamide ;4-((lr,3r)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-N-(2,3-dihydro-4H- benzo [b] [ 1 ,4] oxazin-4-yl) -7 -fluoroquinoline -3 -carboxamide ;8-(2,3-difluoro-5 -(trifluoromethyl) phenyl)-N-(2,3-dihydro-4H-benzo[b][l,4] oxazin-4-yl)-7-fluoro-4- ((lr,3r)-3-fluorocyclobutyl) quinoline-3-carboxamide;N-[(4S)-chroman-4-yl]-8-[2,3-difluoro-5-(trifluoromethyl) phenyl] -7-fluoro-4-(3 -fluorocyclobutyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(dicyanomethyl)-7- fluoroquinoline -3 -carboxamide ;8-(5-chloro-2-fluoro-3 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(2-chloro-5-fluoro-3-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-cyano-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -(trifluoromethoxy) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,5-dichloro-3-(trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;(S)-8-(2-chloro-3-(trifluoromethyl) phenyl)-N-(chroman-4-yl)-4-ethylquinoline-3-carboxamide;8-(2-chloro-3-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-ethyl-7-fluoroquinoline-3- carboxamide;(S)-8-(2-chloro-3-(trifluoromethyl) phenyl)-N-(chroman-4-yl)-4-morpholinoquinoline-3-carboxamide;(S)-8-(3-chloro-5-(trifluoromethyl) phenyl)-N-(chroman-4-yl)-7-fluoro-4-(3-fluoroazetidin-l-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-ethyl-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -propylquinoline-3 -carboxamide ;8-(2-chloro-3-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -(perfluoroethoxy) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(2-cyanopropan-2-yl)-7- fluoroquinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(3-cyanocyclobutyl)-7- fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-dichloro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- cyanocyclobutyl)-7-fluoroquinoline-3-carboxamide;N-((S)-chroman-4-yl)-8-(3,4-dichloro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -nitroquinoline-3 -carboxamide ;7-bromo-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;N-((S)-chroman-4-yl)-4-((ls,3R)-l-cyano-3-fluorocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7 -fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl)-8-(l-methyl-3-(trifluoromethyl)-lH- py razol-4-yl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl)-8-(l-methyl-3-(trifluoromethyl)-lH- py razol-5 -yl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl)-8-(l-(trifluoromethyl)-lH-pyrazol-4-yl) quinoline-3-carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((lr,3R,4S)-3,4- difluorocyclopentyl)-7-fluoroquinoline-3-carboxamide;8-(5-chloro-2-fluoro-3-(pentafluoro-16-sulfaneyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((ls,3R,4S)-3,4- difluorocyclopentyl)-7-fluoroquinoline-3-carboxamide;N-((S)-chroman-4-yl)-4-(2-cyanopropan-2-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7- fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-4-((lr,3S)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7- fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-4-((ls,3R)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7- fluoroquinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lR,2R)-l-cyano-2- (trifluoromethyl)cyclopropyl)-7-fluoroquinoline-3-carboxamide;8-(3-chloro-5-(difluoromethyl)-2-fluorophenyl)-N-((S)-chroman-4-yl)-4-(2-cyanopropan-2-yl)-7- fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((lr,3S)-l,3-difluorocyclobutyl)- 7 -fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((ls,3R)-l,3-difluorocyclobutyl)-7 -fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lR,3S)-3-fluoro-2,2- dimethylcyclobutyl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lS,3S)-3-fluoro-2,2- dimethylcyclobutyl) quinoline -3 -carboxamide ;N-[(4S)-chroman-4-yl]-8-[2,3-difluoro-5-(l,l,2,2,2-pentafluoroethyl) phenyl] -7-fluoro-4-(3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5-(perfluoropropan-2-yl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -(perfluoroethyl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(perfluoropropyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;7-chloro-N-((S)-chroman-4-yl)-8-(3,4-dichloro-5-(trifluoromethyl) phenyl)-4-((lR,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;7-chloro-N-((S)-chroman-4-yl)-8-(2,3-dichloro-5-(trifluoromethyl) phenyl)-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;7-chloro-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-[3-chloro-2-fluoro-5-(trifluoromethyl) phenyl]-N-[(4S)-chroman-4-yl]-6,7-difluoro-4-(3- fluorocyclobutyl) quinoline-3 -carboxamide ;N-((S)-chroman-4-yl)-4-((lr,3S)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-6,7- difluoroquinoline-3-carboxamide;N-((S)-chroman-4-yl)-4-((ls,3R)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-6,7- difluoroquinoline-3-carboxamide;8-[3-chloro-2-fluoro-5-(trifluoromethyl) phenyl]-N-[(4S)-chroman-4-yl]-4-(3-fluorocyclobutyl)-7-(trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- fluorocyclobutyl) -7 -(trifluoromethyl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((lr,3S)-3-fluorocyclobutyl)-7-(trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-6-fluoro-4-((lr,3S)-3- fluorocyclobutyl) -7 -(trifluoromethyl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l-cyanoethyl)-7-(trifluoromethyl) quinoline -3 -carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((ls,3R,4S)-3,4- difluorocyclopentyl)-7-(trifluoromethyl) quinoline -3 -carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((lr,3R,4S)-3,4- difluorocyclopentyl)-7-(trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(2-cyanopropan-2-yl)-7-(trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- cyanocyclobutyl)-7-(trifluoromethyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3-cyanocyclobutyl)-7 -(trifluoromethyl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -(perfluoropropyl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- fluorocyclobutyl) -6-(perfluoroethyl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- fluorocyclobutyl) -6-(perfluoropropyl) quinoline -3 -carboxamide ;N-[(4S)-chroman-4-yl]-4-(3-fluorocyclobutyl)-8-[2-fluoro-5-(trifluoromethyl) phenyl]-6-( 1,1, 2,2,2- pentafluoroethyl) quinoline-3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-4,4-difluoro-l,2,3,4-tetrahydronaphthalen-l- yl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl) quinoline-3-carboxamide;N-((lS)-3-bromo-4,4-difluoro-l,2,3,4-tetrahydronaphthalen-l-yl)-8-(3-chloro-2-fluoro-5- (trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4- morpholinoquinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(2-hydroxypyridin- 4-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(l,l,l- trifluoropropan-2-yl) quinoline-3-carboxamide;8-(2-chloro-5-fluoro-3-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(l,l,l- trifluoropropan-2-yl) quinoline-3-carboxamide;4-(tert-butyl)-N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7-fluoroquinoline-3- carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(perfluoroethyl) quinoline-3-carboxamide;(S)-7-chloro-N-(chroman-4-yl)-8-(3,5-dichlorophenyl)-4-(methoxy(methyl)amino) quinoline-3- carboxamide;7-chloro-N-((S)-chroman-4-yl)-4-(3-fluoroazetidin-l-yl)-8-(2,3,5-trifluorophenyl) quinoline-3- carboxamide;7-chloro-N-((S)-chroman-4-yl)-8-(2,3-dichlorophenyl)-4-ethylquinoline-3-carboxamide;(S)-7-chloro-N-(chroman-4-yl)-8-(3,5-dichlorophenyl)-4-isopropylquinoline-3-carboxamide;N-((S)-chroman-4-yl)-6,7-difluoro-4-morpholino-8-(2,3,5-trifluorophenyl) quinoline-3-carboxamide;(S)-N-(chroman-4-yl)-8-(3,5-dichlorophenyl)-4-(dimethylamino)-6-(trifluoromethyl) quinoline-3- carboxamide;(S)-N-(chroman-4-yl)-8-(2,3-dichlorophenyl)-4-(dimethylamino)-5-(trifluoromethyl)quinoline-3- carboxamide;(S)-8-(5-chloro-2-fluorophenyl)-N-(chroman-4-yl)-4-(dimethylamino)-5-(trifluoromethyl)quinoline-3- carboxamide; and(S)-N-(Chroman-4-yl)-8-(3,5-dichlorophenyl)-4-(dimethylamino)-5-(trifluoromethyl) quinoline-3- carboxamide; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0020] The inventors of the present invention have found that the compounds of the claimed invention have surprising and advantageous properties in the prevention and / or treatment of a disease, in particular of a disease caused by endoparasites such as helminths in an animal, preferably in a cat or a dog. The compounds of the claimed invention also have surprising long-lasting activity properties. It could not have been predicted by the skilled person that the pharmacokinetic properties of the compounds for use according to the invention, especially their distribution, metabolization and tolerance properties in the treated subjects, optionally further modified by formulation (e.g., by a sustained release), are so advantageous that the compounds can prevent and / or treat a disease in different body compartments for a long-term. Therefore, the compounds of the claimed invention can be effectively used for the long-term prevention and / or treatment of a disease, in particular a helminthic infection in an animal, preferably in a cat or a dog. The long-lasting activity properties also ensure that the compounds for use according to the invention can be applied in very convenient (i.e. less- frequent) and cost-efficient dosage regimens.
[0021] Without being bound by theory, the compounds of the claimed invention are considered as modulators of the calcium-activated potassium channel Slo-1 of nematodes. Slo- 1 can be regarded as the helminth' s ortholog of the human KCal .1 channel (potassium calcium-activated channel subfamily M alpha 1), which is encoded by the KCNMA1 gene (KCal. 1 and KCNMA1 are often used synonymously). Slo-1 exhibits calcium-activated potassium channel activity and voltage-gated potassium channel activity. Slo-1 channels play an important role in the neuromuscular system as well as in secretory cells among others. Thus, Slo-1 modulators are reported to be involved in several processes including behavioural response to ethanol, locomotion and pharyngeal pumping. More particularly, Slo-1 modulators disrupt neuromuscular transmission causing a flaccid paralysis and also affect feeding and egg-laying. Further, Slo-1 modulators also slow the development of the larvae and the adults of the corresponding helminth.
[0022] The claimed invention also provides a pharmaceutical composition for use the prevention and / or treatment of a disease, in particuarl a helminthic infection, comprising at least one compound of the claimed invention and at least one further ingredient. The pharmaceutical composition of the claimed invention is particularly suitable for the long-termprevention and / or treatment of a disease, in particular of a helminthic infection. The long- lasting activity properties of the pharmaceutical composition for use according to the invention have been surprising and could not have been predicted by the skilled person.DETAILED DESCRIPTION OF ILLUSTRATIVE EMBODIMENTSGeneral definitions
[0023] The term “substituted” means that one or more hydrogen atoms on the designated atom or group are replaced with a different atom or group, preferably with a selection from an indicated group, provided that the designated atom's normal valency under the existing circumstances is not exceeded. Combinations of substituents and / or variables are permissible.
[0024] The term “optionally substituted” means that the number of substituents can be equal to or different from zero. Unless otherwise indicated, it is possible that optionally substituted groups are substituted with as many optional substituents as can be accommodated by replacing a hydrogen atom with a non-hydrogen substituent on any available carbon or nitrogen atom. Commonly, it is possible for the number of optional substituents, when present, to be 1, 2, 3, 4, 5, 6, 7, 8 or 9, in particular 1, 2 or 3.
[0025] A hyphen at the beginning or at the end of a substituent indicates the point of attachment of said substituent to the rest of the molecule. Similarly, the position via which a respective subsituent is connected to the rest of the molecule may in a drawn structure be depicted by a hash sign (#)in said substituent.
[0026] Should a composite substituent be composed of more than one parts, for example. (Ci-C4-alkoxy)-(Ci-C4-alkyl)-, it is possible for the position of a given part to be at any suitable position of said composite substituent, i.e. the Ci-C4-alkoxy part can be attached to any carbon atom of the Ci-C4-alkyl part of said (Ci-C4-alkoxy)-(Ci-C4-alkyl)-group. A hyphen at the beginning or at the end of such a composite substituent indicates the point of attachment of said composite substituent to the rest of the molecule.
[0027] Should a ring, comprising carbon atoms and optionally one or more heteroatoms, such as N, O or S, be substituted with a substituent, it is possible for said substituent to be bound at any suitable position of said ring, be it bound to a suitable carbon atom and / or to a suitable heteroatom. For example, a 4- to 6-membered lactame or a 4- to 6-membered heterocycloalkanone can be substituted at the nitrogen atom.
[0028] Preparation of the compounds according to the invention and the detetermi nation of properties of compounds according to the invention requires conventional techniques known to the skilled person unless otherwise indicated. These techniques are fully explained in the literature.
[0029] Unless otherwise defined herein, scientific and technical terms used in this application shall have the meanings that are commonly understood by those of ordinary skill in the art. In case of conflict, the present specification, including definitions, will control.
[0030] The terms as mentioned in the present text have the following meanings:
[0031] The term “comprising” when used in the specification includes “consisting of’. For example, a composition “comprising” X may consist exclusively of X or may include something additional, for example, X + Y.
[0032] The word “substantially” does not exclude “completely”. For example, a composition which is “substantially free” from Y may be completely free from Y.
[0033] If within the present text any item is referred to as “as mentioned herein”, it means that it may be mentioned anywhere in the present text.
[0034] As used herein, the term “about” modifying the quantity of an ingredient, parameter, calculation, or measurement in the compositions / formulations employed in the methods of the disclosure refers to the variation in the numerical quantity that can occur. Such variation can be within an order of magnitude, typically within 10%, more typically still within 5%, of a given value or range. The term “about” also encompasses amounts that differ due to differentequilibrium conditions for a composition resulting from a particular initial mixture. Whether or not modified by the term “about”, the paragraphs include equivalents to the quantities. Reference to “about” a value or parameter herein includes (and describes) embodiments that are directed to that value or parameter per se. For example, description referring to “about X” includes description of “X”.
[0035] Numeric ranges are inclusive of the numbers defining the range.
[0036] The term “halogen atom” means a fluorine, chlorine, bromine or iodine atom, preferably a fluorine, chlorine or bromine atom, more preferably a fluorine or chlorine atom.
[0037] The term “Ci-C4-alkyl” means a linear or branched, saturated, monovalent hydrocarbon group having 1, 2, 3, or 4 carbon atoms, for example a methyl, ethyl, / / -propyl, isopropyl, / / -butyl, .scc-butyl, isobutyl or a tert-butyl group, or a further constitutional isomer thereof. Particularly, said group has 1, 2 or 3 carbon atoms (“Ci-Cs-alkyl”), for example a methyl, ethyl, / / -propyl or isopropyl group.
[0038] The term “Ci-Ce-alkyl” means a linear or branched, saturated, monovalent hydrocarbon group having 1, 2, 3, 4, 5 or 6 carbon atoms.
[0039] The term “Ci-C4-alkoxy” means a linear or branched, saturated, monovalent group of formula (Ci-C4-alkyl)-O-, in which the term “Ci-C4-alkyl” is as defined supra, for example a methoxy, ethoxy, / / -propoxy, isopropoxy, / / -butoxy, .scc-butoxy, isobutoxy, te / 7-butoxy group, pentoxy, or a further constitutional isomer thereof.
[0040] The term “Ci-C4-oalkyl-CO-” means a linear or branched, saturated, monovalent Ci-C4-alkyl group, as defined supra, connected to the rest of the molecule via a carbonyl group.
[0041] The term “C1-C4-O-CO-” means a linear or branched, saturated, monovalent group of formula (Ci-C4-alkyl)-O-C=O-, in which the term “Ci-C4-alkyl-O-” is as defined supra, forexample a methoxy, ethoxy, / / -propoxy, isopropoxy, / / -butoxy, .scc-butoxy, isobutoxy, Zc / 7-butoxy group, pentoxy, or a further constitutional isomer thereof.
[0042] The term “-NH(Ci-C4-alkyl)”, “-N(Ci-C4-alkyl)2” or “-N(Ci-C4-alkyl)(Ci-C4-alkoxy)” means a linear or branched, saturated, monovalent group in which the term “Ci-C4-alkyl” is as defined supra, for example a methylamino, ethylamino, / / -propylamino, isopropylamino, N,N- dimethylamino, 7V-methyl-7V-ethylamino, / f-diethylamino or N,O-dimethylhydroxylamino group.
[0043] The term “-S-Ci-C4-alkyl”, “-SO-Ci-C4-alkyl” or “-SO2-Ci-C4-alkyl” means a linear or branched, saturated group in which the term “Ci-C4-alkyl” is as defined supra, for example a methylsulfanyl, ethylsulfanyl, / / -propylsulfanyl, isopropylsulfanyl, / / -butylsulfanyl, sec- butylsulfanyl, isobutyl sulfanyl or Zc / 7-butyl sulfanyl group, a methylsulfmyl, ethylsulfinyl, n- propylsulfinyl, isopropylsulfinyl, / / -butylsulfinyl, .scc-butylsulfinyl, isobutyl sulfinyl or tert- butylsulfinyl group, or a methylsulfonyl, ethylsulfonyl, / / -propylsulfonyl, isopropylsulfonyl, / / -butylsulfonyl, .scc-butylsulfonyl, isobutyl sulfonyl or Zc / 7-butyl sulfonyl group.
[0044] The term “Ci-C4-halogenoalkyl” means a linear or branched, saturated, monovalent hydrocarbon group in which the term “Ci-C4-alkyl” is as defined supra, and in which one or more of the hydrogen atoms are replaced, identically or differently, with a halogen atom. Preferably, said halogen atom is a fluorine, chlorine or bromine atom, more preferably a fluorine or chlorine atom, most preferably a fluorine atom. Said Ci-C4-halogenoalkyl group is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 3,3,3-trifluoropropyl or 1 ,3 -difluoropropan-2-yl .
[0045] The term “Ci-C4-halogenoalkoxy” means a linear or branched, saturated, monovalent Ci-C4-alkoxy group, as defined supra, in which one or more of the hydrogen atoms is replaced, identically or differently, with a halogen atom. Preferably, said halogen atom is a fluorine, chlorine or bromine atom, more preferably a fluorine or chlorine atom, most preferably a fluorine atom. Said Ci-Ce-halogenoalkoxy group is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy or pentafluoroethoxy.
[0046] The term “Ci-C4-halogenoalkyl-CO-” means a linear or branched, saturated, monovalent Ci-C4-alkyl group, as defined supra, connected to the rest of the molecule via a carbonyl group, in which one or more of the hydrogen atoms is replaced, identically or differently, with a halogen atom. Preferably, said halogen atom is a fluorine, chlorine or bromine atom, more preferably a fluorine or chlorine atom, most preferably a fluorine atom.
[0047] The term “Ci-C4-halogenoalkyl-S-”, “Ci-C4-halogenoalkyl-SO-” or “Ci-C4-halogenoalkyl-SO2-” means a linear or branched, saturated, monovalent Ci-C4-alkyl group, as defined supra, connected to the rest of the molecule via a -S-, -SO- or -SO2- group, in which one or more of the hydrogen atoms is replaced, identically or differently, with a halogen atom. Preferably, said halogen atom is a fluorine, chlorine or bromine atom, more preferably a fluorine or chlorine atom, most preferably a fluorine atom.
[0048] The term “Cs-Ce-cycloalkyl” means a saturated, monovalent, monocyclic hydrocarbon ring which contains 3, 4, 5 or 6 carbon atoms (“Cs-Ce-cycloalkyl”). Said Cs-Ce-cycloalkyl group is for example, a monocyclic hydrocarbon ring, for example a cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl group.
[0049] The term “Cs-Ce-halogenocycloalkyl having 1 to 11 halogen atoms” means a saturated, monovalent, monocyclic hydrocarbon ring which contains 3, 4, 5 or 6 carbon atoms (“Cs-Ce-cycloalkyl”) and 1 to 11 halogen atoms. Said Cs-Ce-cycloalkyl group is for example, a monocyclic hydrocarbon ring, for example a cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl group. Preferably, said halogen atom is a fluorine, chlorine or bromine atom, more preferably a fluorine or chlorine atom, most preferably a fluorine atom.
[0050] The term “C4-C6-cycloalkenone” means a monocyclic, unsaturated ring containing a carbonyl group. The C4-C6-cycloalkenone can be substituted. In particular, the C4-C6- cycloalkenone can comprise further carbonyl groups. Unless otherwise indicated, it is possible for said C4-C6-cycloalkenone to be attached via a any ring carbon atom (if allowed by valency).
[0051] The term “ 4- to 10-membered heterocycloalkyl” means a monocyclic or bicyclic, saturated or partially saturated heterocycle with 4, 5, 6, 7, 8, 9, or 10 ring atoms in total, which contains one or two identical or different heteroatoms selected from the group consisting of N, O and S. Unless otherwise indicated, it is possible for said heterocycloalkyl group to be attached to the rest of the molecule via any one of the carbon atoms or, if present, a nitrogen atom. Said heterocycloalkyl group, without being limited thereto, can be a 4- membered ring, such as azetidinyl, oxetanyl or thietanyl, for example; or a 5-membered ring, such as tetrahydrofuranyl, oxolanyl, 1,3-dioxolanyl, thiolanyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, 1,1-dioxidothiolanyl, 1,2-oxazolidinyl, 1,3-oxazolidinyl, 1,3-thiazolidinyl or 1,2,4-triazolidinyl, for example; or a 6-membered ring, such as tetrahydropyranyl, tetrahydrothiopyranyl, piperidinyl, morpholinyl, dithianyl, thiomorpholinyl, piperazinyl, oxanyl, 1,3-dioxanyl, 1,4-dioxanyl or 1,2-oxazinanyl, for example; or a 7-membered ring, such as azepanyl, 1,4-diazepanyl or 1,4-oxazepanyl, for example; or a bicyclic 7-membered ring, such as 2-oxa-5-azabicyclo[4.1.0]heptan-5-yl or 6-oxa-3-azabicyclo[3.1.1]heptan, for example. Further, the 4- to 10-membered heterocycloalkyl can be substituted. The substitution can be on any carbon atom or heteroatom (if allowed by valency).
[0052] The term “5- to 6-membered aryl” means a monocyclic aromatic ring having 5 or 6 carbon ring atoms, for example a phenyl group.
[0053] The term “5- or 6-membered heteroaryl” means a monocyclic aromatic ring having 5 or 6 ring atoms, which contains one or two identical or different heteroatoms selected from the group consisting of N, O and S. Unless otherwise indicated, it is possible for said heteroaryl group to be attached via a ring carbon atom or optionally via a ring nitrogen atom (if allowed by valency). Said heteroaryl group can be a 5-membered heteroaryl group, such as, for example, thienyl, furanyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl or tetrazolyl; or a 6-membered heteroaryl group, such as, for example, pyridinyl, dihydropyridinyl, pyridazinyl, pyrimidinyl, tetrahydropyrimidinyl, pyrazinyl or triazinyl. Further, the 5- or 6-membered heteroaryl can be substituted. The substitution can be on any carbon atom or at the nitrogen atom (if present and allowed by valency).
[0054] The term “4- to 6-membered cyclic sulfone” means a monocyclic ring having 4, 5 or 6 ring atoms, which contains a sulfone group. Unless otherwise indicated, it is possible for said cyclic sulfone to be attached via any ring carbon atom (if allowed by valency).
[0055] The term “4- to 6-membered cyclic sulfinyl” means a monocyclic ring having 4, 5 or 6 ring atoms, which contains a sulfinyl group. Unless otherwise indicated, it is possible for said cyclic sulfinyl to be attached via any ring carbon atom (if allowed by valency).
[0056] The term “4- to 6-membered lactame” means a cyclic amide having 4, 5 or 6 ring atoms. Said lactame can be a azetidin-2-one, pyrrolidin-2-one or piperidin-2-one. Unless otherwise indicated, it is possible for said 4- to 6-membered lactame to be attached via a any ring carbon atom or the nitrogen atom (if allowed by valency). Further, the 4- to 10- membered lactame can be substituted. The substitution can be on any carbon atom or at the nitrogen atom (if allowed by valency).
[0057] The term “4- to 6-membered lactone” means a cyclic carboxylic ester having 4, 5 or 6 ring atoms. Said lactone can be a oxetan-2-one, oxolan-2-one or oxolan-2-one. Unless otherwise indicated, it is possible for said lactone to be attached via any ring carbon atom or (if allowed by valency).
[0058] The term “4- to 6-membered heterocycloalkanone” means a heterocycloalkyl, as defined supra, containing a carbonyl group. Said heterocycloalkanone can contain further carbonyl groups. Unless otherwise indicated, it is possible for said heterocycloalkyl group to be attached to the rest of the molecule via any one of the carbon atoms or, if present, a nitrogen atom. Further, the 4- to 6-membered heterocycloalkanone can be substituted. The substitution can be on any carbon atom or at a nitrogen atom (if allowed by valency).
[0059] When a range of values is given, said range encompasses each value and sub-range within said range. For example:"C1-C2" encompasses Ci and C2;"C1-C3" encompasses Ci, C2, C3, C1-C2, and C2-C3;"C1-C4" encompasses Ci, C2, C3, C4, C1-C2, Ci-C3, C2-C3, C2-C4, and C3-C4;"Ci-C6" encompasses Ci, C2, C3, C4, C5, C6, C1-C2, C1-C3, C1-C4, C1-C5, Ci-C6, C2-C3, C2-C4,C2-C5, C2-C6, C3-C4, C3-C5, C3-C6, C4-C5, C4-C6, and C5-C6; and"C3-C6" encompasses C3, C4, C5, C6, C3-C4, C3-C5, C3-C6, C4-C5, C4-C6, and C5-C6.
[0060] It is possible for the compounds of general formula (I) to exist as isotopic variants. The invention therefore includes one or more isotopic variant(s) of the compounds of general formula (I), particularly deuterium-containing compounds of general formula (I).
[0061] The term “isotopic variant” of a compound or a reagent is defined as a compound exhibiting an unnatural proportion of one or more of the isotopes that constitute such a compound. The expression “unnatural proportion” means a proportion of such isotope which is higher than its natural abundance. The natural abundances of isotopes to be applied in this context are described in “Isotopic Compositions of the Elements 1997”, Pure Appl. Chem., 70(1), 217-235, 1998.
[0062] Examples of such isotopes include stable and radioactive isotopes of hydrogen, carbon, nitrogen, oxygen, phosphorus, sulfur, fluorine, chlorine, bromine and iodine, such as2H (deuterium),3H (tritium),nC,13C,14C,15N,17O,18O,32P,33P,33S,34S,35S,36S,18F,36C1,82Br,123I,124I,125I,129I and131I, respectively.
[0063] With respect to the treatment and / or prevention of the disorders specified herein the isotopic variant(s) of the compounds of general formula (I) preferably contain deuterium (“deuterium-containing compounds of general formula (I)”). Isotopic variants of the compounds of general formula (I) in which one or more radioactive isotopes, such as3H or14C, are incorporated are useful, for example, in drug and / or substrate tissue distribution studies. These isotopes are particularly preferred for the ease of their incorporation and detectability. Positron emitting isotopes such as18F ornC may be incorporated into a compound of general formula (I). These isotopic variants of the compounds of general formula (I) are useful for in vivo imaging applications. Deuterium-containing and13C-containing compounds of general formula (I) can be used in mass spectrometry analyses in the context of preclinical or clinical studies.
[0064] Isotopic variants of the compounds of general formula (I) can generally be prepared by methods known to a person skilled in the art, such as those described in the schemes and / or examples herein, by substituting a reagent for an isotopic variant of said reagent, preferably for a deuterium-containing reagent. Depending on the desired sites of deuteration, in some cases deuterium from D2O can be incorporated either directly into the compounds or into reagents that are useful for synthesizing such compounds. Deuterium gas is also a useful reagent for incorporating deuterium into molecules. Catalytic deuteration of olefinic bonds and acetylenic bonds is a rapid route for incorporation of deuterium. Metal catalysts (i.e. Pd, Pt, and Rh) in the presence of deuterium gas can be used to directly exchange deuterium for hydrogen in functional groups containing hydrocarbons. A variety of deuterated reagents and synthetic building blocks are commercially available from companies such as for example C / D / N Isotopes, Quebec, Canada; Cambridge Isotope Laboratories Inc., Andover, MA, USA; and CombiPhos Catalysts, Inc., Princeton, NJ, USA.
[0065] The term “deuterium-containing compound of general formula (I)” is defined as a compound of general formula (I), in which one or more hydrogen atom(s) is / are replaced by one or more deuterium atom(s) and in which the abundance of deuterium at each deuterated position of the compound of general formula (I) is higher than the natural abundance of deuterium, which is about 0.015%. Particularly, in a deuterium-containing compound of general formula (I) the abundance of deuterium at each deuterated position of the compound of general formula (I) is higher than 10%, 20%, 30%, 40%, 50%, 60%, 70% or 80%, preferably higher than 90%, 95%, 96% or 97%, even more preferably higher than 98% or 99% at said position(s). It is understood that the abundance of deuterium at each deuterated position is independent of the abundance of deuterium at other deuterated position(s).
[0066] The selective incorporation of one or more deuterium atom(s) into a compound of general formula (I) may alter the physicochemical properties (such as for example acidity [C. L. Perrin, et al., J. Am. Chem. Soc., 2007, 129, 4490], basicity [C. L. Perrin et al., J. Am. Chem. Soc., 2005, 127, 9641], lipophilicity [B. Testa et al., Int. J. Pharm., 1984, 19(3), 271]) and / or the metabolic profile of the molecule and may result in changes in the ratio of parent compound to metabolites or in the amounts of metabolites formed. Such changes may result in certain therapeutic advantages and hence may be preferred in some circumstances. Reducedrates of metabolism and metabolic switching, where the ratio of metabolites is changed, have been reported (A. E. Mutlib et al., Toxicol. Appl. Pharmacol., 2000, 169, 102). These changes in the exposure to parent drug and metabolites can have important consequences with respect to the pharmacodynamics, tolerability and efficacy of a deuterium-containing compound of general formula (I). In some cases, deuterium substitution reduces or eliminates the formation of an undesired or toxic metabolite and enhances the formation of a desired metabolite (for example Nevirapine: A. M. Sharma et al., Chem. Res. Toxicol., 2013, 26, 410; Efavirenz: A. E. Mutlib et al., Toxicol. Appl. Pharmacol., 2000, 169, 102). In other cases, the major effect of deuteration is to reduce the rate of systemic clearance. As a result, the biological half-life of the compound is increased. The potential clinical benefits would include the ability to maintain similar systemic exposure with decreased peak levels and increased trough levels. This could result in lower side effects and enhanced efficacy, depending on the particular compound’s pharmacokinetic / pharmacodynamic relationship. ML-337 (C. J. Wenthur et al., J. Med. Chem., 2013, 56, 5208) and Odanacatib (K. Kassahun et al., WO2012 / 112363) are examples for this deuterium effect. Still other cases have been reported in which reduced rates of metabolism result in an increase in exposure of the drug without changing the rate of systemic clearance (for example Rofecoxib: F. Schneider et al., Arzneim. Forsch. / Drug. Res., 2006, 56, 295; Telaprevir: F. Maltais et al., J. Med. Chem., 2009, 52, 7993). Deuterated drugs showing this effect may have reduced dosing requirements (for example lower number of doses or lower dosage to achieve the desired effect) and / or may produce lower metabolite loads.
[0067] A compound of general formula (I) may have multiple potential sites of attack for metabolism. To optimize the above-described effects on physicochemical properties and metabolic profile, deuterium-containing compounds of general formula (I) having a certain pattern of one or more deuterium-hydrogen exchange(s) can be selected. Particularly, the deuterium atom(s) of deuterium-containing compound(s) of general formula (I) is / are attached to a carbon atom and / or is / are located at those positions of the compound of general formula (I), which are sites of attack for metabolizing enzymes such as for example cytochrome P450.
[0068] Where the plural form of the word compounds, salts, polymorph, stereoisomer, hydrates, solvates and the like, is used herein, this is taken to mean also a single compound,salt, polymorph, stereoisomer, hydrate, solvate or the like. Also, when referring to a ‘noun’ in singular, the plural is meant to be included, unless specified otherwise.
[0069] As used in the present disclosure and claims the singular forms “a”, “an” and “the” include plural forms unless the context clearly dictates otherwise.
[0070] The compounds of the present invention optionally contain one or more asymmetric centres, depending upon the location and nature of the various substituents desired. It is possible that one or more asymmetric carbon atoms are present in the (R) or (S) configuration, which can result in racemic mixtures in the case of a single asymmetric centre, and in diastereomeric mixtures in the case of multiple asymmetric centres. In certain instances, it is possible that asymmetry also be present due to restricted rotation about a given bond, for example, the central bond adjoining two substituted aromatic rings of the specified compounds. In certain instances, it is possible that asymmetry may also be present due to restricted rotation around a double bond or due to a ring structure, wherein the rotation of bonds is restricted or prevented. These geometric isomers may be indicated as cis- or transisomers or as (E)- and (Z)-i somers.
[0071] Preferred compounds are those which produce the more desirable biological activity. Separated, pure or partially purified constitutional isomers and stereoisomers or racemic or diastereomeric mixtures of the compounds of the present invention are also included within the scope of the present invention. The purification and the separation of such materials can be accomplished by standard techniques known in the art.
[0072] The optical isomers can be obtained by resolution of the racemic mixtures according to conventional processes, for example, by the formation of diastereoisomeric salts using an optically active acid or base or formation of covalent diastereomers. Examples of appropriate acids are tartaric, diacetyltartaric, ditoluoyltartaric and camphorsulfonic acid. Mixtures of diastereoisomers can be separated into their individual diastereomers on the basis of their physical and / or chemical differences by methods known in the art, for example, by chromatography or fractional crystallisation. The optically active bases or acids are then liberated from the separated diastereomeric salts. A different process for separation of opticalisomers involves the use of chiral chromatography (for example, HPLC columns using a chiral phase), with or without conventional derivatisation, optimally chosen to maximise the separation of the enantiomers. Suitable HPLC columns using a chiral phase are commercially available, such as those manufactured by Dai cel, for example, Chiracel OD and Chiracel OJ, for example, among many others, which are all routinely selectable. Enzymatic separations, with or without derivatisation, are also useful. The optically active compounds of the present invention can likewise be obtained by chiral syntheses utilizing optically active starting materials.
[0073] In order to distinguish different types of stereoisomers from each other reference is made to IUPAC Rules Section E (Pure Appl Chem 45, 11-30, 1976).
[0074] The present invention includes all possible stereoisomers of the compounds of the present invention as single stereoisomers, or as any mixture of said stereoisomers, for example, (R)- or (S)- stereoisomers, (E)- or (Z)-isomers, cis- or trans-i somers, in any ratio. Isolation of a single stereoisomer, for example, a single enantiomer or a single diastereomer, of a compound of the present invention is achieved by any suitable state of the art method, such as chromatography, especially chiral chromatography.
[0075] The present invention includes all possible tautomers of the compounds of the present invention as single tautomers, or as any mixture of said tautomers, in any ratio.
[0076] Further, the compounds of the present invention can exist as N-oxides, which are defined in that at least one nitrogen of the compounds of the present invention is oxidised. The present invention includes all such possible N-oxides.
[0077] The present invention also covers useful forms of the compounds of the present invention, such as metabolites, hydrates, solvates, prodrugs, salts, in particular pharmaceutically acceptable salts, and / or co-precipitates.
[0078] The compounds of the present invention can exist as a hydrate, or as a solvate, wherein the compounds of the present invention contain polar solvents, in particular water,methanol or ethanol for example, as structural element of the crystal lattice of the compounds. It is possible for the amount of polar solvents, in particular water, to exist in a stoichiometric or non-stoichiometric ratio. In the case of stoichiometric solvates, for example a hydrate, hemi-, (semi-), mono-, sesqui-, di-, tri-, tetra-, penta- etc. solvates or hydrates, respectively, are possible. The present invention includes all such hydrates or solvates.
[0079] Further, it is possible for the compounds of the present invention to exist in free form, for example as a free base, or as a free acid, or as a zwitterion, or to exist in the form of a salt. Said salt may be any salt, either an organic or inorganic addition salt, particularly any pharmaceutically acceptable organic or inorganic addition salt, which is customarily used in pharmacy, or which is used, for example, for isolating or purifying the compounds of the present invention.
[0080] The term “pharmaceutically acceptable salt" refers to an inorganic or organic acid addition salt of a compound of the present invention. For example, see S. M. Berge, et al. “Pharmaceutical Salts,” J. Pharm. Sci. 1977, 66, 1-19.
[0081] A suitable pharmaceutically acceptable salt of the compounds of the present invention may be, for example, an acid-addition salt of a compound of the present invention bearing a nitrogen atom, in a chain or in a ring, for example, which is sufficiently basic, such as an acidaddition salt with an inorganic acid, or “mineral acid”, such as hydrochloric, hydrobromic, hydroiodic, sulfuric, sulfamic, bisulfuric, phosphoric, or nitric acid, for example, or with an organic acid, such as formic, acetic, acetoacetic, pyruvic, trifluoroacetic, propionic, butyric, hexanoic, heptanoic, undecanoic, lauric, benzoic, salicylic, 2-(4-hydroxybenzoyl)-benzoic, camphoric, cinnamic, cyclopentanepropionic, di gluconic, 3 -hydroxy -2-naphthoic, nicotinic, pamoic, pectinic, 3 -phenylpropionic, pivalic, 2-hydroxy ethanesulfonic, itaconic, trifluoromethanesulfonic, dodecylsulfuric, ethanesulfonic, benzenesulfonic, paratoluenesulfonic, methanesulfonic, 2-naphthalenesulfonic, naphthalinedisulfonic, camphorsulfonic acid, citric, tartaric, stearic, lactic, oxalic, malonic, succinic, malic, adipic, alginic, maleic, fumaric, D-gluconic, mandelic, ascorbic, glucoheptanoic, glycerophosphoric, aspartic, sulfosalicylic, or thiocyanic acid, for example.
[0082] Further, another suitably pharmaceutically acceptable salt of a compound of the present invention which is sufficiently acidic, is an alkali metal salt, for example a sodium or potassium salt, an alkaline earth metal salt, for example a calcium, magnesium or strontium salt, or an aluminium or a zinc salt, or an ammonium salt derived from ammonia or from an organic primary, secondary or tertiary amine having 1 to 20 carbon atoms, such as ethylamine, diethylamine, triethylamine, ethyldiisopropylamine, monoethanolamine, diethanolamine, triethanolamine, dicyclohexylamine, dimethylaminoethanol, diethylaminoethanol, tris(hydroxymethyl)aminomethane, procaine, dibenzylamine, N- methylmorpholine, arginine, lysine, 1,2-ethylenediamine, 7V-methylpiperi dine, 7V-m ethylglucamine, A,7V-dimethyl-glucamine, 7V-ethyl-glucamine, 1,6-hexanediamine, glucosamine, sarcosine, serinol, 2-amino-l,3-propanediol, 3-amino-l,2-propanediol, 4-amino-l,2,3- butanetriol, or a salt with a quarternary ammonium ion having 1 to 20 carbon atoms, such as tetramethylammonium, tetraethylammonium, tetra( / / -propyl)ammonium, tetraf / / - butyl)ammonium, 7V-benzyl-A,A,7V-trimethylammonium, choline or benzalkonium.
[0083] Those skilled in the art will further recognise that it is possible for acid addition salts of the claimed compounds to be prepared by reaction of the compounds with the appropriate inorganic or organic acid via any of a number of known methods. Alternatively, alkali and alkaline earth metal salts of acidic compounds of the present invention are prepared by reacting the compounds of the present invention with the appropriate base via a variety of known methods.
[0084] The present invention includes all possible salts of the compounds of the present invention as single salts, or as any mixture of said salts, in any ratio.
[0085] Unless specified otherwise, suffixes to chemical names or structural formulae relating to salts, such as "hydrochloride", "trifluoroacetate", "sodium salt", or "x HQ", "x CF3COOH", "x Na+", for example, mean a salt form, the stoichiometry of which salt form not being specified.
[0086] Furthermore, the present invention includes all possible crystalline forms, or polymorphs, of the compounds of the present invention, either as single polymorph, or as a mixture of more than one polymorph, in any ratio.
[0087] It belongs to the skilled person’s common general knowledge and thus includes standard techniques to produce any stereoisomer, tautomer, N-oxide, hydrate, solvate, salt, or mixture of the same of a compound for use according to the claimed invention.Compounds1. Compounds according to alternative (i)
[0088] In one embodiment, the compound according to formula (I) is a compound according to alternative (i) whereinA is AlA1 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Cs-Ce-halogenocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halog enoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;FC is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy,Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl- CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R3 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, - SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, -NO2, -CONH2, -CH2-CONH2, -CHC=NCONH2, -COOH, Ci-C4-alkyl substituted with 1, 2 or 3 substituents selected from the group consisting of -CHO, -NO2, -SO2-Ci-C4-alkyl, and -SO-Ci-C4-alkyl,-Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,Cs-Ce -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -C00H, 4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -C00H,4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -C00H, 4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -C00H, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -C00H,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains lor 2 heteratoms selected from the group consisting of O, N, and S, wherein the 4- to 6-membered heteroaryl is connected to the rest of the molecule via a carbon atom and wherein the 4- to 6- membered heteroaryl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -N02, -NH2, -C0NH2, -CHO and -C00H,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -C00H,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -N02, -NH2, -C0NH2, - CHO, =0 and -C00H; is selected from the group consisting of a 5- or 6-membered aryl and 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0089] In one embodiment, the compound according to formula (I) is a compound according to alternative (i) whereinA is AlA1 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, -NO2, -CONH2, -CH2-CONH2, -CHC=NCONH2, -COOH, Ci-C4-alkyl substituted with 1, 2 or 3 substituents selected from the group consisting of -CHO, -NO2, -SO2-Ci-C4-alkyl, and -SO-Ci-C4-alkyl, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, wherein the 4- to 6-membered heteroaryl is connected to the rest of the molecule via a carbon atom and wherein the 4- to 6- membered heteroaryl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Q is selected from the group consisting of a 5- or 6-membered aryl and a 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0090] In one embodiment, the compound according to formula (I) is a compound according to alternative (i)whereinA is AlA1 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, -NO2, -CONH2, -CH2-CONH2, -CHC=N-SO2-(Cl-C4-alkyl), -CHC=NCONH2, -COOH,Ci-C4-alkyl substituted with 1, 2 or 3 substituents selected from the group consisting of -CHO, -NO2, -SO2-Ci-C4-alkyl, and -SO-Ci-C4-alkyl,-Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and Ci-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, wherein the 4- to 6-membered heteroaryl is connected to the rest of the molecule via a carbon atom and wherein the 4- to 6-membered heteroaryl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Q is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered heteroaryl contains 2 heteratoms selected from the group consisting of N, O and S, preferably the two heteroatoms in the 5 -membered heteroaryl are N, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0091] In one embodiment, the compound according to formula (I) is a compound according to alternative (i) whereinA is Alwherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, and -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms ;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, -NO2, -CONH2, -CH2-CONH2, -CHC=N-SO2-(Cl-C4-alkyl), -CHC=NCONH2, - COOH,Ci-C4-alkyl substituted with 1, 2 or 3 substituents selected from the group consisting of -CHO, -NO2, -SO2-Ci-C4-alkyl, and -SO-Ci-C4-alkyl, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2-Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C5 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(Ci-C4-alkyl), - N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH,4- to 6-membered heterocycloalkyl, wherein the 4- to 6-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 5-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 5 -membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 5-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, wherein the 4- to 6-membered heteroaryl is connected to the rest of the molecule via a carbon atom and wherein the 4- to 6- membered heteroaryl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH; is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered aryl is selected from the group consisting of pyrazole, imidazole, oxazole, isoxazole, isothiazole, thiazole, pyrazole, and imidazole, preferably the 5 -membered heteroaryl is selected from the group consisting of pyrazole, and imidazole, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent;or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0092] In one embodiment, the compound according to formula (I) is a compound according to alternative (i) whereinA is AlA1 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of O and S;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2,-NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, -NH2, - OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, brominc-NCK - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting of hydrogen, -NO2, -CONH2, -CH2-CONH2, -CHC=N-SO2-methyl, -CHC=NCONH2, -COOH, methyl, ethyl, propyl, isopropyl, tert-butyl, wherein the methyl, ethyl, propyl, isopropyl, or tert-butyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -CHO, -NO2, -SO2-methyl, and -SO-methyl,wherein# indicates the connection to the rest of the molecule,Li is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2,wherein# indicates the connection to the rest of the molecule,L2 is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), -CONH(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl,wherein# indicates the connection to the rest of the molecule,L3 is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), -CONH(ethyl), -CON(methyl)(methyl), -CON(methyl)(ethyl), -CON(ethyl)(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl, cyclopropyl, cyclobutyl, cyclopentyl wherein the cyclopropyl, cyclobutyl and cyclopently are optionally substituted with 1, 2 or 3 substituents selected from the group consisting of methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, methyl, ethyl, and -NO2,wherein# indicates the connection to the rest of the molecule,Rio is selected from the group consisting of methyl and ethyl,R11 is selected from the group consisting of -NH2, -NH(methyl), -NH(ethyl), -NH(methyl)(methyl), -NH(ethyl)(methyl), -NH(ethyl)(ethyl), methoxy, ethoxy, -OH, -NO2, -NH2, -CONH2, and -COOH,azetidine, oxetane, thietane, pyrolidine, tetrahydrofuran, tetrahydriothiophene, piperidine, tetrahydropyrane, thiane, morpholine, 1,4-dioxine, 1,4-dithiane, piperazine, imidazolidine, 1,3 -dioxolane, or 1,3 -oxathiolane, wherein the azetidine, oxetane, thietane, pyrolidine, tetrahydrofuran, tetrahydriothiophene, piperidine, tetrahydropyrane, thiane, morpholine, 1,4-dioxine, 1,4-dithiane, piperazine, imidazolidine, 1,3 -dioxolane, or 1,3 -oxathiolane is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, fluorine, chlorine, bromine, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, pyridine, pyrimidine, or pyrazine wherein pyridine, pyrimidine or pyrazine is is connected to the rest of the molecule via a carbon atom and wherein the pyridine, pyrimidine or pyrazine is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone selected from the group consisting ofwherein the 5- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, or 3 substituents selected from the group consisting of methyl, ethyl, fluorine, chlorine, -OH, -NO2, -NH2, -CONH2, -CHO, and -COOH;Q is selected from the group consisting of phenyl, pyrazole, and imidazole, wherein the phenyl, pyrazole or imidazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl, pyrazole or imidazole is substituted with at least one halogen or halogencontaining substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0093] In one embodiment, the compound according to formula (I) is a compound according to alternative (i) whereinA is AlA1 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of O;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atomsselected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, -NO2, - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, and ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting ofwherein # indicates the connection to the rest of the molecule,Q is selected from the group consisting of phenyl, and pyrazole, wherein the 6 phenyl and pyrazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl and pyrazole is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0094] In one embodiment, the compound according to formula (I) is a compound according to alternative (i) wherein the compound is selected from the group consisting of8-(3, 5 -difluoro-2 -(trifluoromethyl) phenyl)-7-fluoro-4-morpholino-N-(2,3,4a,8a-tetrahydro-4H- benzo[b]-[l,4] oxazin-4-yl) quinoline -3 -carboxamide;N-(2,3-dihydro-4H-benzo[b][l,4] oxazin-4-yl)-8-(2-fhioro-5-(trifhioromethyl) phenyl)-4- morpholinoquinoline-3 -carboxamide ; andN-(2,3-dihydro-4H-benzo[b][l,4] oxazin-4-yl)-6,7-difhroro-4-morpholino-8-(2,3,5-trifluorophenyl) quinoline-3-carboxamide; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.2. Compounds according to alternative (ii)
[0095] In one embodiment, the compound according to formula (I) is a compound according to alternative (ii) whereinA is A2wherein # indicates the connection to the rest of the molecule;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Cs-Ce-halogenocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halog enoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl- CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R3 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, - SC>2-Ci-C4-alkyl, and -SC>2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=N-SO2-(Ci-C4-alkyl), -CHC=NCONH2,-Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH,4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Rs hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, and -CHO;Re hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, and -CHO;R7 hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, and -CHO;Q is selected from the group consisting of a 5- or 6-membered aryl and 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0096] In one embodiment, the compound according to formula (I) is a compound according to alternative (ii) whereinA is A2wherein # indicates the connection to the rest of the molecule;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=N-SO2-(Cl-C4-alkyl), -CHC=NCONH2, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2,-N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-C6-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -C00H,4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -C0NH2, -CHO and -C00H,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -C0NH2, -CHO and -C00H,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -C0NH2, -CHO and -C00H,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -C0NH2, -CHO and -C00H,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -C0NH2, - CHO, =0 and -C00H;Rs hydrogen, halogen, -N02, -NH2, -OH, cyano, -C00H, and -CHO;Re hydrogen, halogen, -N02, -NH2, -OH, cyano, -C00H, and -CHO;R? hydrogen, halogen, -N02, -NH2, -OH, cyano, -C00H, and -CHO;Q is selected from the group consisting of a 5- or 6-membered aryl and a 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0097] In one embodiment, the compound according to formula (I) is a compound according to alternative (ii) whereinA is A2wherein # indicates the connection to the rest of the molecule;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=N-SO2-(Cl-C4-alkyl), -CHC=NCONH2, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen,-N02, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2is O or S and wherein -Ci-Ce-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L2is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and Ci-C4- alkoxy,Cs-Ce -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -N02, -NH2, -C0NH2, - CHO, =0 and -COOH;Rs hydrogen, halogen, -N02, -NH2, -OH, cyano, -COOH, and -CHO; s hydrogen, halogen, -N02, -NH2, -OH, cyano, -COOH, and -CHO;R? hydrogen, halogen, -N02, -NH2, -OH, cyano, -COOH, and -CHO;Q is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5— membered heteroaryl contains 2 heteratoms selected from the group consisting of N, O and S, preferably the two heteroatoms in the 5 -membered heteroaryl are N, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0098] In one embodiment, the compound according to formula (I) is a compound according to alternative (ii) whereinA is A2wherein # indicates the connection to the rest of the molecule;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, and -S-Ci-C4-alkyl;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-N02, -CH2-CONH2, -CHC=N-SO2-(Cl-C4-alkyl), -CHC=NC0NH2, -Ci-C6-alkyl-C(=Li)-NH2wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen,-N02, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2, -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L; is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and Ci-C4- alkoxy,C3-C5 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(Ci-C4-alkyl), - N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH,4- to 5 -membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 5 -membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,5 -membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen,-OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -N02, -NH2, -C0NH2, - CHO, =0 and -COOH;Rs hydrogen, halogen;Re hydrogen, halogen;R? hydrogen, halogen;Q is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered aryl is selected from the group consisting of pyrazole, imidazole, oxazole, isoxazole, isothiazole, thiazole, pyrazole, and imidazole, preferably the 5 -membered heteroaryl is selected from the group consisting of pyrazole, and imidazole, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0099] In one embodiment, the compound according to formula (I) is a compound according to alternative (ii) whereinA is A2wherein # indicates the connection to the rest of the molecule;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2,-NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propylsubstituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, -NH2, - OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, brominc-NCK - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=N-SO2-methyl, -CHC=NCONH2,wherein# indicates the connection to the rest of the molecule,Li is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2,wherein indicates the connection to the rest of the molecule,L2 is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), - CONH(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl,wherein indicates the connection to the rest of the molecule,L3 is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), - CONH(ethyl), -CON(methyl)(methyl), -CON(methyl)(ethyl), -CON(ethyl)(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl, cyclopropyl, cyclobutyl, cyclopentyl wherein the cyclopropyl, cyclobutyl and cyclopently are optionally substituted with 1, 2 or 3 substituents selected from the group consisting of methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, methyl, ethyl, and -NO2,wherein# indicates the connection to the rest of the molecule,Rio is selected from the group consisting of methyl and ethyl,Rn is selected from the group consisting of -NH2, -NH(methyl), -NH(ethyl),-NH(methyl)(methyl), -NH(ethyl)(methyl), -NH(ethyl)(ethyl), methoxy, ethoxy, -OH, -NO2, -NH2, -CONH2, and -COOH,4-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5 -membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen,-OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone selected from the group consisting ofwherein the 5- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, or 3 substituents selected from the group consisting of methyl, ethyl, fluorine, chlorine, -OH, -NO2, -NH2, -CONH2, -CHO, and -COOH;Rs hydrogen, fluorine, chlorine, bromine;Re hydrogen, fluorine, chlorine, bromine;R7 hydrogen, fluorine, chlorine, bromine;Q is selected from the group consisting of phenyl, pyrazole, and imidazole, wherein the phenyl, pyrazole or imidazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein phenyl, pyrazole or imidazole is substituted with at least one halogen or halogencontaining substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0100] In one embodiment, the compound according to formula (I) is a compound according to alternative (ii) whereinA is A2wherein # indicates the connection to the rest of the molecule; is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, -NO2, - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, and ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting ofwherein # indicates the connection to the rest of the molecule,Rs hydrogen, fluorine, chlorine, bromine;Re hydrogen, fluorine, chlorine, bromine;R? hydrogen, fluorine, chlorine, bromine;Q is selected from the group consisting of phenyl, and pyrazole, wherein the phenyl and pyrazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl and pyrazole is substituted with at least one halogen or halogencontaining substituent;or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.3. Compounds according to alternative (iii)
[0101] In one embodiment, the compound according to formula (I) is a compound according to alternative (iii) whereinA3 wherein # indicates the connection to the rest of the molecule;Y is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, -CHO, -CO-O-Ci-C4-alkyl, -NH(Ci-C4-alkyl), -S-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and -SO2-Ci-C4-alkyl;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Cs-Ce-halogenocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halog enoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy,Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, - SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, halogen, cyano, -NO2, -NH2, -N(Ci-C4-alkyl)(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci-C4- alkoxy), -CONH2, -CH2-CONH2, -CHC=NCONH2, -OH, -CHO, -COOH,Ci-C4-alkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -OH, -CHO, -COOH, -NO2, -NH2, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci- C4-alkyl), -SO2-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and Ci-C4-alkoxy, Ci-C4-haloalkyl having 1 to 9 halogen atoms, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,Cs-Ce -cycloalkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, cyano, Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, -OH, -NO2, -NH2, -CONH2, and -COOH, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH, 4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, and is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -N02, -NH2, -C0NH2, - CHO, =0 and -COOH; is selected from the group consisting of a 5- or 6-membered aryl and 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0102] In one embodiment, the compound according to formula (I) is a compound according to alternative (iii) whereinA is A3A3 wherein # indicates the connection to the rest of the molecule;Y is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, -CHO, -CO-O-Ci-C4-alkyl, -NH(Ci-C4-alkyl), -S-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and -SO2-Ci-C4-alkyl;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkylhaving 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SC>2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms; Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, halogen, cyano, -NO2, -NH2, -N(Ci-C4-alkyl)(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci-C4- alkoxy), -CONH2, -CH2-CONH2, -CHC=NCONH2, -OH, -CHO, -COOH,Ci-C4-alkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -OH, -CHO, -COOH, -NO2, -NH2, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci- C4-alkyl), -SO2-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and Ci-C4-alkoxy, Ci-C4-haloalkyl having 1 to 9 halogen atoms, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, cyano, Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, -OH, -NO2, -NH2, -CONH2, and -COOH, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH,4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, and is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH; is selected from the group consisting of a 5- or 6-membered aryl and a 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent;or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0103] In one embodiment, the compound according to formula (I) is a compound according to alternative (iii) whereinwherein # indicates the connection to the rest of the molecule;Y is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, -CHO, -CO-O-Ci-C4-alkyl, -NH(Ci-C4-alkyl), -S-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and -SO2-Ci-C4-alkyl;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1- -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SC>2-Ci-C4-alkyl, and -SC>2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, halogen, cyano, -NO2, -NH2, -N(Ci-C4-alkyl)(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci-C4- alkoxy), -CONH2, -CH2-CONH2, -CHC=NCONH2, -OH, -CHO, -COOH,Ci-C4-alkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -OH, -CHO, -COOH, -NO2, -NH2, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci- C4-alkyl), -SO2-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and Ci-C4-alkoxy, Ci-C4-haloalkyl having 1 to 9 halogen atoms, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, cyano, Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, -OH, -NO2, -NH2, -CONH2, and -COOH, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, and is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Q is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered heteroaryl contains 2 heteratoms selected from the group consisting of N, O and S, preferably the two heteroatoms in the 5 -membered heteroaryl are N, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0104] In one embodiment, the compound according to formula (I) is a compound according to alternative (iii) whereinA is A3A3 wherein # indicates the connection to the rest of the molecule;Y is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, -CHO, and -CO-O-Ci-C4-alkyl;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, and -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4is selected from the group consisting of hydrogen, halogen, cyano, -NO2, -NH2, -N(Ci-C4-alkyl)(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci-C4- alkoxy), -CONH2, -CH2-CONH2, -CHC=NCONH2, -OH, -CHO, -COOH,Ci-C4-alkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -OH, -CHO, -COOH, -NO2, -NH2, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci- C4-alkyl), -SO2-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and Ci-C4-alkoxy,Ci-C4-haloalkyl having 1 to 9 halogen atoms, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2, -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl),-CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and Ci-C4- alkoxy,C3-C5 -cycloalkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, cyano, Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, -OH, -NO2, -NH2, -CONH2, and -COOH, -N(Ci-C4-alkyl)(C4-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(Ci-C4-alkyl), - N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 6-membered heterocycloalkyl, wherein the 4- to 6-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 5-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH, 4- to 5 -membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH, 4- to 5-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 5 -membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, and is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituentsselected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -C00H;Q is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered aryl is selected from the group consisting of pyrazole, imidazole, oxazole, isoxazole, isothiazole, thiazole, pyrazole, and imidazole, preferably the 5 -membered heteroaryl is selected from the group consisting of pyrazole, and imidazole, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0105] In one embodiment, the compound according to formula (I) is a compound according to alternative (iii) whereinA is A3A3 wherein # indicates the connection to the rest of the molecule;Y is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, -NH2, -OH, cyano, -COOH, methoxy, ethoxy, propxy, isopropxy, -CHO, and -CO-O-methyl and -CO-O-ethyl;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2,-NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, -NH2, - OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, brominc-NCK - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, -NO2, -NH2, -N(methyl)2, -N(ethyl)2, -N(methyl)(methoxy), -N(methyl)(ethoxy), -N(ethyl)(methoxy), -CONH2, -CH2-CONH2, -CHC=NCONH2, -OH, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, tert-butyl, wherein methyl, ethyl, propyl, isopropyl, or tertbutyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -OH, -CHO, -COOH, -NO2, -NH2, -NH(methyl) -NH(ethyl), -N(methyl)2, -N(ethyl)2, -SO2-methyl, -SO-methyl,methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, butyl substituted with 1, 2, 3, 4, 5, 6, 7, 8, or 9 halogen atoms selected from the group consisting of F, Cl, and Br, tert-butyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br,wherein# indicates the connection to the rest of the molecule,Li is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2,wherein# indicates the connection to the rest of the molecule,L2is O or SRs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), - CONH(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl,# indicates the connection to the rest of the molecule,L3 is O or SRs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), - CONH(ethyl), -CON(methyl)(methyl), -CON(methyl)(ethyl), -CON(ethyl)(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl, cyclopropyl, cyclobutyl, cyclopentyl wherein cyclopropyl, cyclobutyl and cyclopently are optionally substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, , methyl, ethyl, -OH, -NO2, -NH2, -CONH2, and - COOH,wherein# indicates the connection to the rest of the molecule,Rio is selected from the group consisting of methyl and ethyl,R11 is selected from the group consisting of -NH2, -NH(methyl), -NH(ethyl), -NH(methyl)(methyl), -NH(ethyl)(methyl), -NH(ethyl)(ethyl), methoxy, ethoxy, -OH, - NO2, -NH2, -CONH2, and -COOH, azetidine, oxetane, thietane, pyrolidine, tetrahydrofuran, tetrahydriothiophene, piperidine, tetrahydropyrane, thiane, morpholine, 1,4-dioxine, 1,4-dithiane, piperazine, imidazolidine, 1,3 -dioxolane, or 1,3 -oxathiolane, wherein the azetidine, oxetane, thietane, pyrolidine, tetrahydrofuran, tetrahydriothiophene, piperidine, tetrahydropyrane, thiane, morpholine, 1,4-dioxine, 1,4-dithiane, piperazine, imidazolidine, 1,3 -dioxolane, or 1,3 -oxathiolane is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4— membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, fluorine, chlorine, bromine, -OH, -NO2, - NH2, -CONH2, -CHO and -COOH, pyridine, pyrimidine, or pyrazine wherein the pyridine, pyrimidine or pyrazine is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of fluroine, chlorine, bromine, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 5- to 6-membered heterocycloalkanone selected from the group consisting ofwherein the 5- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, or 3 substituents selected from the group consisting of methyl, ethyl, fluorine, chlorine, -OH, -NO2, -NH2, -CONH2, -CHO, and -COOH; is selected from the group consisting of phenyl, pyrazole, and imidazole, wherein the 6 phenyl, pyrazole or imidazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from thegroup consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl, pyrazole or imidazole is substituted with at least one halogen or halogencontaining substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0106] In one embodiment, the compound according to formula (I) is a compound according to alternative (iii) whereinwherein # indicates the connection to the rest of the molecule;Y is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, - NH2, -OH, cyano, -COOH, -CHO, and -CO-O-methyl and -CO-O-ethyl;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxysubstituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, -NO2, - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, and ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting of fluorine, chlorine, bromine, cyano, -NO2, -NH2, -N(methyl)2, -N(methyl)(methoxy), -CONH2,-CH2-CONH2, methyl, ethyl, propyl, isopropyl, tert-butyl,methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br,wherein # indicates the connection to the rest of the molecule,Q is selected from the group consisting of phenyl, and pyrazole, wherein the phenyl and pyrazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl and pyrazole is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0107] In one embodiment, the compound according to formula (I) is a compound according to alternative (iii) wherein the compound is selected from the group consisting of ethyl l-(8-(3-chloro-2-fhioro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lr,3r)-3-fluorocyclobutyl) quinoline-3 -carboxamido)- 1 ,2,3 ,4-tetrahydro- 1 ,4-methanonaphthalene-9-carboxylate; and8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-(3,4-dihydro-l,4-methanonaphthalen-l(2H)-yl)-7- fluoro-4-(( lr,3r)-3-fluorocyclobutyl) quinoline -3 -carboxamide;or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.4. Compounds according to alternative (iv)
[0108] In one embodiment, the compound according to formula (I) is a compound according to alternative (iv) whereinA is A4A4 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Cs-Ce-halogenocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halog enoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl- CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkylhaving 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, - SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=N-SO2-(Ci-C4-alkyl), -CHC=NCONH2, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Q is selected from the group consisting of a 5- or 6-membered aryl and 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0109] In one embodiment, the compound according to formula (I) is a compound according to alternative (iv) whereinA is A4A4 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,-SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=NCONH2,-Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl),-CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and Ci-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -N02, -NH2, -C0NH2, - CHO, =0 and -COOH; is selected from the group consisting of a 5- or 6-membered aryl and a5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, andwherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0110] In one embodiment, the compound according to formula (I) is a compound according to alternative (iv) whereinA is A4A4 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SC>2-Ci-C4-alkyl, and -SC>2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=NCONH2,-Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -C00H;Q is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered heteroaryl contains 2 heteratoms selected from the group consisting of N, O and S, preferably the two heteroatoms in the 5 -membered heteroaryl are N, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.[OlH] In one embodiment, the compound according to formula (I) is a compound according to alternative (iv) whereinA is A4A4 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-C00H, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, and -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=NCONH2,-Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2, and -CSN(Ci-C4-alkyl)(Ci- C4-alkyl),-Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C5 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(Ci-C4-alkyl), - N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 5 -membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 5 -membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5 -membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen,-OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Q is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered aryl is selected from the group consisting of pyrazole, imidazole, oxazole, isoxazole, isothiazole, thiazole, pyrazole, and imidazole, preferably the 5 -membered heteroaryl is selected from the group consisting of pyrazole, and imidazole, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0112] In one embodiment, the compound according to formula (I) is a compound according to alternative (iv) whereinA is A4wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of O and S;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2,-NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, isopropyl, propyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, -NH2, - OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, brominc-NCK - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=NCONH2,wherein# indicates the connection to the rest of the molecule,Li is O or S,R8is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -N02, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2.wherein# indicates the connection to the rest of the molecule,L2is O or S,R8is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), - CONH(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl,wherein# indicates the connection to the rest of the molecule,L3 is O or SR8is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), - CONH(ethyl), -CON(methyl)(methyl), -CON(methyl)(ethyl), -CON(ethyl)(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl, cyclopropyl, cyclobutyl, cyclopentyl wherein the cyclopropyl, cyclobutyl and cyclopently are optionally substituted with 1, 2 or 3 substituents selected from the group consisting of methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, methyl, ethyl, and -NO2,wherein# indicates the connection to the rest of the molecule,Rio is selected from the group consisting of methyl and ethyl,Rn is selected from the group consisting of -NH2, -NH(methyl), -NH(ethyl), - NH(methyl)(methyl), -NH(ethyl)(methyl), -NH(ethyl)(ethyl), methoxy, ethoxy, -OH, - NO2, -NH2, -CONH2, and -COOH,4-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5 -membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, fluorine, chlorine, bromine, -OH, -NO2, -NH2, - CONH2, -CHO and -COOH,5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone selected from the group consisting ofwherein the 5- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, or 3 substituents selected from the group consisting of methyl, ethyl, fluorine, chlorine, -OH, -NO2, -NH2, -CONH2, -CHO, and -COOH;Q is selected from the group consisting of phenyl, pyrazole, and imidazole, wherein the 6 phenyl, pyrazole or imidazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl, pyrazole or imidazole is substituted with at least one halogen or halogencontaining substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0113] In one embodiment, the compound according to formula (I) is a compound according to alternative (iv) whereinA is A4A4 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of O and S;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atomsselected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, -NO2, - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, and ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting of-NO2, -CH2-CONH2,wherein # indicates the connection to the rest of the molecule,Q is selected from the group consisting of phenyl, and pyrazole, wherein the phenyl and pyrazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl and pyrazole is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
[0114] In one embodiment, the compound according to formula (I) is a compound according to alternative (iv) wherein the compound is selected from the group consisting of4-(2-amino-l-cyano-2-oxoethyl)-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4- yl) -7 -fluoroquinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(methyl(2- (methylamino) -3 ,4-dioxocyclobut- 1 -en- 1 -yl)amino) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((S)-6- oxopiperidin-3-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((R)-5- oxotetrahydrofuran-3 -yl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((2-methoxy-3,4- dioxocyclobut- 1 -en- 1 -yl)(methyl)amino) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((S)-2- oxopiperidin-4-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(2,6-dioxopiperidin-4-yl)-7- fluoroquinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((R)-2- oxoimidazolidin-4-yl) quinoline -3 -carboxamide;N-((S)-chroman-4-yl)-8-(2,3-dichloro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;N-((S)-chroman-4-yl)-7-fluoro-4-((R)-l-methyl-5-oxopyrrolidin-3-yl)-8-(2,3,5-trifluorophenyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(6-oxo-l, 2,3,6- tetrahydropyridin-4-yl) quinoline -3 -carboxamide;N-((S)-chroman-4-yl)-7-fluoro-4-(5-oxo-l-(trifluoromethyl) pyrrolidin-3-yl)-8-(2,3,5-trifluorophenyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(5-oxopyrrolidin-3- yl) quinoline-3 -carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7-fluoro-4-(l- (trifluoromethyl)cyclopropyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((S)-2,5-dioxopyrrolidin-3- yl) -7 -fluoroquinoline-3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7-fluoro-4-(5-oxopyrrolidin-3-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(l-(trifluoromethyl)cyclopropyl) quinoline-3-carboxamide;4-(l-amino-2-methyl-l-oxopropan-2-yl)-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl) -N-((S)- chroman-4-yl)-7-fluoroquinoline-3-carboxamide;4-(l-amino-2-methyl-l-thioxopropan-2-yl)-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)- chroman-4-yl)-7-fluoroquinoline-3-carboxamide;- I l l -N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((R)-2,2-dimethyl-5- oxopyrrolidin-3 -yl) -7 -fluoroquinoline-3 -carboxamide ;2-(8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-3-(((S)-chroman-4-yl) carbamoyl)-7- fluoroquinolin-4-yl)-Nl,Nl,N3,N3-tetramethylmalonamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l-(dimethylamino)-2- methyl-l-oxopropan-2-yl)-7-fluoroquinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(2-methyl-l- (methylamino)-l-oxopropan-2-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,3-dimethyl-2,4,6- trioxohexahydropyrimidin-5 -yl)-7 -fluoroquinoline -3 -carboxamide ;2-(8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-3-(((S)-chroman-4-yl) carbamoyl)-7- fluoroquinolin-4-yl)malonamide ;2-(8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-3-(((S)-chroman-4-yl) carbamoyl)-7- fluoroquinolin-4-yl)-Nl,N3-dimethylmalonamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l -cyano- 1 -(methylsulfonyl) ethyl)-7 -fluoroquinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(2-methyl-l- (methylamino)-l-thioxopropan-2-yl) quinoline-3-carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-6,7-difluoro-4-((S)-5-oxopyrrolidin-3-yl) quinoline-3-carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-(l,l-dioxidothietan-3-yl)-7- (trifluoromethyl) quinoline -3 -carboxamide; and8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((S)- cyano(methylsulfonyl)methyl)-7-(trifluoromethyl) quinoline-3-carboxamide; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.5. Compounds according to alternative (v)
[0115] In one embodiment, the compound according to formula (I) is a compound according to alternative (v)wherein the compound is selected from the group consisting of8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(l-oxidothietan-3- yl) quinoline-3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-7- fluoroquinoline -3 -carboxamide ;7-bromo-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l- dioxidothietan-3 -yl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difhioro-5-(trifhroromethyl) phenyl)-4-(l,l-dioxidothietan-3-yl)-7- fluoroquinoline -3 -carboxamide ;7-chloro-8-(3-chloro-2-fhroro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l- dioxidothietan-3 -yl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)- 6, 7 -difluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difhioro-5-(trifhroromethyl) phenyl)-4-(l,l-dioxidothietan-3-yl)-6,7- difluoroquinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-7- (trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-6- fluoro-7-(trifluoromethyl) quinoline-3-carboxamide;(S)-8-(3-chloro-2-fhioro-5-(trifhroromethyl) phenyl)-N-(chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-6- (perfluoroethyl) quinoline -3 -carboxamide ;(S)-8-(3-chloro-2-fhioro-5-(trifhroromethyl) phenyl)-N-(chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-6- (perfluoropropyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-(2,3-dihydro-4H-benzo[b][l,4] oxazin-4-yl)-7- fluoro-4-(( lr,3r)-3-fluorocyclobutyl) quinoline -3 -carboxamide;4-((ls,3s)-3-cyanocyclobutyl)-8-(2,3-difhioro-5-(trifluoromethyl) phenyl)-N-(2,3-dihydro-4H- benzo [b] [ 1 ,4] oxazin-4-yl) -7 -fluoroquinoline -3 -carboxamide ;4-((lr,3r)-3-cyanocyclobutyl)-8-(2,3-difhroro-5-(trifluoromethyl) phenyl)-N-(2,3-dihydro-4H- benzo [b] [ 1 ,4] oxazin-4-yl) -7 -fluoroquinoline -3 -carboxamide ;8-(2,3-difluoro-5 -(trifluoromethyl) phenyl)-N-(2,3-dihydro-4H-benzo[b][l,4] oxazin-4-yl)-7-fluoro-4- ((lr,3r)-3-fluorocyclobutyl) quinoline-3-carboxamide;N-[(4S)-chroman-4-yl]-8-[2,3-difluoro-5-(trifluoromethyl) phenyl] -7-fluoro-4-(3 -fluorocyclobutyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(dicyanomethyl)-7- fluoroquinoline -3 -carboxamide ;8-(5-chloro-2-fluoro-3 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(2-chloro-5-fluoro-3-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-cyano-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -(trifluoromethoxy) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,5-dichloro-3-(trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;(S)-8-(2-chloro-3-(trifluoromethyl) phenyl)-N-(chroman-4-yl)-4-ethylquinoline-3-carboxamide;8-(2-chloro-3-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-ethyl-7-fluoroquinoline-3- carboxamide;(S)-8-(2-chloro-3-(trifluoromethyl) phenyl)-N-(chroman-4-yl)-4-morpholinoquinoline-3-carboxamide;(S)-8-(3-chloro-5-(trifluoromethyl) phenyl)-N-(chroman-4-yl)-7-fluoro-4-(3-fluoroazetidin-l-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-ethyl-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -propylquinoline-3 -carboxamide ;8-(2-chloro-3-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -(perfluoroethoxy) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(2-cyanopropan-2-yl)-7- fluoroquinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(3-cyanocyclobutyl)-7- fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-dichloro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- cyanocyclobutyl)-7-fluoroquinoline-3-carboxamide;N-((S)-chroman-4-yl)-8-(3,4-dichloro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -nitroquinoline-3 -carboxamide ;7-bromo-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;N-((S)-chroman-4-yl)-4-((ls,3R)-l-cyano-3-fluorocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7 -fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl)-8-(l-methyl-3-(trifluoromethyl)-lH- py razol-4-yl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl)-8-(l-methyl-3-(trifluoromethyl)-lH- py razol-5 -yl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl)-8-(l-(trifluoromethyl)-lH-pyrazol-4-yl) quinoline-3-carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((lr,3R,4S)-3,4- difluorocyclopentyl)-7-fluoroquinoline-3-carboxamide;8-(5-chloro-2-fluoro-3-(pentafluoro-16-sulfaneyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((ls,3R,4S)-3,4- difluorocyclopentyl)-7-fluoroquinoline-3-carboxamide;N-((S)-chroman-4-yl)-4-(2-cyanopropan-2-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7- fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-4-((lr,3S)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7- fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-4-((ls,3R)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7- fluoroquinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lR,2R)-l-cyano-2- (trifluoromethyl)cyclopropyl)-7-fluoroquinoline-3-carboxamide;8-(3-chloro-5-(difluoromethyl)-2-fluorophenyl)-N-((S)-chroman-4-yl)-4-(2-cyanopropan-2-yl)-7- fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((lr,3S)-l,3-difluorocyclobutyl)- 7 -fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((ls,3R)-l,3-difluorocyclobutyl)-7 -fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lR,3S)-3-fluoro-2,2- dimethylcyclobutyl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lS,3S)-3-fluoro-2,2- dimethylcyclobutyl) quinoline -3 -carboxamide ;N-[(4S)-chroman-4-yl]-8-[2,3-difluoro-5-(l,l,2,2,2-pentafluoroethyl) phenyl] -7-fluoro-4-(3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5-(perfluoropropan-2-yl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -(perfluoroethyl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(perfluoropropyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;7-chloro-N-((S)-chroman-4-yl)-8-(3,4-dichloro-5-(trifluoromethyl) phenyl)-4-((lR,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;7-chloro-N-((S)-chroman-4-yl)-8-(2,3-dichloro-5-(trifluoromethyl) phenyl)-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;7-chloro-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-[3-chloro-2-fluoro-5-(trifluoromethyl) phenyl]-N-[(4S)-chroman-4-yl]-6,7-difluoro-4-(3- fluorocyclobutyl) quinoline-3 -carboxamide ;N-((S)-chroman-4-yl)-4-((lr,3S)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-6,7- difluoroquinoline-3-carboxamide;N-((S)-chroman-4-yl)-4-((ls,3R)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-6,7- difluoroquinoline-3-carboxamide;8-[3-chloro-2-fluoro-5-(trifluoromethyl) phenyl]-N-[(4S)-chroman-4-yl]-4-(3-fluorocyclobutyl)-7- (trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- fluorocyclobutyl) -7 -(trifluoromethyl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((lr,3S)-3-fluorocyclobutyl)-7- (trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-6-fluoro-4-((lr,3S)-3- fluorocyclobutyl) -7 -(trifluoromethyl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l-cyanoethyl)-7- (trifluoromethyl) quinoline -3 -carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((ls,3R,4S)-3,4- difluorocyclopentyl)-7-(trifluoromethyl) quinoline -3 -carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((lr,3R,4S)-3,4- difluorocyclopentyl)-7-(trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(2-cyanopropan-2-yl)-7- (trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- cyanocyclobutyl)-7-(trifluoromethyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3-cyanocyclobutyl)-7 -(trifluoromethyl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -(perfluoropropyl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- fluorocyclobutyl) -6-(perfluoroethyl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- fluorocyclobutyl) -6-(perfluoropropyl) quinoline -3 -carboxamide ;N-[(4S)-chroman-4-yl]-4-(3-fluorocyclobutyl)-8-[2-fluoro-5-(trifluoromethyl) phenyl]-6-( 1,1, 2,2,2- pentafluoroethyl) quinoline-3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-4,4-difluoro-l,2,3,4-tetrahydronaphthalen-l- yl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl) quinoline-3-carboxamide;N-((lS)-3-bromo-4,4-difluoro-l,2,3,4-tetrahydronaphthalen-l-yl)-8-(3-chloro-2-fluoro-5- (trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4- morpholinoquinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(2-hydroxypyridin- 4-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(l,l,l- trifluoropropan-2-yl) quinoline-3-carboxamide;8-(2-chloro-5-fluoro-3-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(l,l,l- trifluoropropan-2-yl) quinoline-3-carboxamide;4-(tert-butyl)-N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7-fluoroquinoline-3- carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(perfluoroethyl) quinoline-3-carboxamide;(S)-7-chloro-N-(chroman-4-yl)-8-(3,5-dichlorophenyl)-4-(methoxy(methyl)amino) quinoline-3- carboxamide;7-chloro-N-((S)-chroman-4-yl)-4-(3-fluoroazetidin-l-yl)-8-(2,3,5-trifluorophenyl) quinoline-3- carboxamide;7-chloro-N-((S)-chroman-4-yl)-8-(2,3-dichlorophenyl)-4-ethylquinoline-3-carboxamide;(S)-7-chloro-N-(chroman-4-yl)-8-(3,5-dichlorophenyl)-4-isopropylquinoline-3-carboxamide; N-((S)-chroman-4-yl)-6,7-difluoro-4-morpholino-8-(2,3,5-trifluorophenyl) quinoline-3-carboxamide; (S)-N-(chroman-4-yl)-8-(3,5-dichlorophenyl)-4-(dimethylamino)-6-(trifluoromethyl) quinoline-3- carboxamide;(S)-N-(chroman-4-yl)-8-(2,3-dichlorophenyl)-4-(dimethylamino)-5-(trifluoromethyl)quinoline-3- carboxamide;(S)-8-(5-chloro-2-fluorophenyl)-N-(chroman-4-yl)-4-(dimethylamino)-5-(trifluoromethyl)quinoline-3- carboxamide; and(S)-N-(Chroman-4-yl)-8-(3,5-dichlorophenyl)-4-(dimethylamino)-5-(trifluoromethyl) quinoline-3- carboxamide; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.Prevention and / or treatment of a disease, including long-term prevention and / or treatment of a disease
[0116] The claimed invention concerns compounds for use in the prevention and / or treatment of a disease.
[0117] In one embodiment, the compounds of the invention or the pharmaceutical compositions of the invention exert a reachback activity. The term “reachback activity” refers to the ability of a compound of the invention or a pharmaceutical composition of the invention to eliminate parasitic larvae that have been present in the subject to be treated before the compound of the invention or the pharmaceutical composition of the invention has been administered. Thus, the reachback activity allows the retroactive killing of parasiticlarvae that have already been present in the subject to be treated and provides protection against the development of adult helminths for a period of time prior to the actual administration of the compound of the invention or the pharmaceutical composition of the invention. Preferably, the larval infection that took place not more than two months before administration of the compound of the invention or the pharmaceutical composition of the invention.
[0118] In one embodiment, the compound for use in the prevention and / or treatment of a disease has an EC50 value from 0. 1 nM to 200 nM, preferably from 0.5 nM to 100 nM, more preferably from 1 nM to 10 nM. Compounds for use according to the invention with such EC50 values are particularly suitable in the prevention and / or treatment of a disease, in particular in the prevention and / or treatment of an helminthic infection in an animal, preferably in a cat or a dog. Methods to determine the EC50 value of a given compound are part of the common general knowledge of the skilled person.
[0119] In particular, the claimed invention also concerns compounds for use in the long-term prevention and / or treatment of a disease.
[0120] In one embodiment, the compounds of the invention or the pharmaceutical compositions of the invention exert a residual activity or a residual protection. The term “residual activity” or “residual protection” as used herein relates to an activity of a compound of the invention or a pharmaceutical composition of the invention to eliminate parasitic larvae that have been introduced into the subject after the compound of the invention or the pharmaceutical composition of the invention has been administered. Thus, the residual activity allows to kill parasitic larvae that have been transmitted to the subject after administration of the compound of the invention or the pharmaceutical composition of the invention and provides provides protection against the development of an helminthic infection for a period of time after the actual administration of the compound of the invention or the pharmaceutical composition of the invention. Preferably, the larval infection took place not more than three months after administration of the compound of the invention or the pharmaceutical composition of the invention.
[0121] In one embodiment, the compound for use in the long-term prevention and / or treatment of a disease has a half-life of at least 5 days, preferably at least 10 days, more preferably at least 15 days, and most preferably at least 20 days. Compounds for use according to the invention with such a halflife are particularly suitable in the long-term prevention and / or treatment of a disease, in particular in the long-term prevention and / or treatment of an helminthic infection in an animal, preferably in a cator a dog. Methods to determine the half-life of a given compound are part of the common general knowledge of the skilled person.
[0122] In one embodiment, the compound for use in the long-term prevention and / or treatment of a disease has a plasma clearance of less than 0.2 L / h / kg, preferably less than 0.15 L / h / kg and most preferably less than 0. 1 L / h / kg. Compounds for use according to the invention with such a plasma clearance are particularly suitable in the long-term prevention and / or treatment of a disease, in particular in the long-term prevention and / or treatment of an helminthic infection in an animal, preferably in a cat or a dog. Methods to determine the plasma-clearance of a given compound are part of the common general knowledge of the skilled person.
[0123] The compounds of the invention can have further favorable properties supporting the prevention and / or treatment of a disease by these compounds, including the long-term prevention and / or treatment of a disease by these compounds. This could, e.g., concern the solubility of the compounds, their non-toxicity over broad dose ranges as well as their hepatic recirculation.
[0124] In one embodiment, the term “long-term” means a period of time of at least 15 days, preferably at least one month, more preferably at least one and a half months, even more preferably at least two months, and most preferably at least three months. It was surprising that the compounds for use according to the claimed invention have this long-term effect of preventing and / or treating a disease, in particular an helminthic infection in an animal, preferably in a cat or a dog.
[0125] In one embodiment, the term “long-term” means that the prevention and / or treatment of a disease is held for a period of time of at least 15 days, preferably at least one month, more preferably at least one and a half months, even more preferably at least two months, and most preferably at least three months with an efficacy of at least 40%, preferably at least 50%, more preferably at least 60%, even more preferably at least 70%, still more preferably at least 80% and most preferably at least 90%.
[0126] The term “efficacy” as used herein means the power to produce any effect on the prevention and / or treatment a disease. It belongs to the skilled person’s common general knowledge to choose and apply a suitable standard technique to determine the efficacy in preventing and / or treating a given disease when using a compound according to the claimed invention. For example, in case the disease is a helminthic infection, the skilled person could determine the prevention and / or treatment efficacies of the used compound as described in in vivo assay 2 of the Experimental Section below.
[0127] In one embodiment, the term “for use in the long-term prevention and / or treatment of a disease” means that the compound prevents and / or treats the onset of a disease occurring or arising at least 15 days after its administration, preferably at least one month after its administration, more preferably at least one and a half months after its administration, even more preferably at least two months after its administration, and most even more preferably at least three months after its administration. The compounds of the claimed invention are particularly effective to prevent and / or treat the onset of a disease, in particular the onset of an helmintic infection in an animal, preferably in a cat or a dog, when the disease occurs in these time intervals after administration of the compound.
[0128] The terms "treating" or "preventing“ of a disease or disorder includes preventing or protecting against the disease or disorder (that is, causing the clinical symptoms not to develop), inhibiting the disease or disorder (i.e., arresting or suppressing the development of clinical symptoms), and / or relieving the disease or disorder (i.e., causing the regression of clinical symptoms). It is not always possible to distinguish between ..preventing" and ..suppressing" a disease or disorder since the ultimate inductive event or events may be unknown or latent. Accordingly, the term „prophylaxis" can also be understood to constitute a type of „treatment" that encompasses both ..preventing" and ..suppressing". The term „treatment" can thus include „prophylaxis" .
[0129] In one embodiment, the compound for use according to the invention (i.e. the active compound) is formulated in a form that enables a sustained release of the compound when administered to a subject. This has the advantage that the long-term properties of the compounds for use according to the invention can be further modulated and / or enhanced so that a particularly efficient long-term effect regarding the prevention and / or treatment of a disease is achieved, in particular in the long-term prevention and / or treatment of an helminthic infection in an animal, preferably in a cat or a dog.
[0130] The term “enables a sustained release” means in particular “ensures a sustained release”.
[0131] The term “sustained release” is known by the skilled person and refers to the delivery of a compound at a programmed rate that leads to a compound delivery for a prolonged period of time compared the delivery of a compound formulated in a conventional rapid-release formulation, in particular a conventional rapid-release tablet or suspension administered orally. In one embodiment, the “sustained release” is effected by a subcutaneous injection that has sustained release relative to thePO administration. Such sustained release is derived from the inherent solubility characteristics of the molecule and the route of administration. A conventional rapid-release tablet or suspension is one that is not formulated to release the compound in a modified way. Rapid-release tablets or suspensions are in particular those which, according to the USP release method using apparatus 2 (paddle), have a Q value (30 minutes) of 75 %.
[0132] The skilled person knows and / or can readily identify by standard techniques suitable formulations that allow a sustained release of the administered compound. For example, microencapsulation could be used. Another strategy could be to use compound-polymer conjugates (for example hydrogels) to ensure a sustained-release of the active compound.Disease
[0133] The claimed invention concerns compounds for use in the prevention and / or treatment of a disease.
[0134] In particular, the claimed invention also concerns compounds for use in the long-term prevention and / or treatment of a disease.
[0135] In one embodiment, the disease is a helminithic infection. The compounds according to the claimed invention are particularly efficient in the long-term prevention (i.e. prophylaxis) and / or treatment of helminthic infections, preferably gastro-intestinal and extra-intestinal helminthic infections. By using the compounds of the present invention for long-term prevention and / or treatment of a disease, in particular a helminthic infection, a reduction or prevention of illness, cases of deaths and performance reductions are achieved in the subjects in need thereof such as animals (in the case of meat, milk, wool, hides, eggs, honey and the like). This ensures economical and simpler animal keeping and better animal well-being.
[0136] Helminths pathogenic for humans or animals include, for example, acanthocephala, nematodes, pentastoma and platyhelmintha (e.g. monogenea, cestodes and trematodes).Exemplary helminths include, but are not limited to:Monogenea:for example Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglocephalus spp.Cestodes: from the order of the Pseudophyllidea, for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp., Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp. from the order of the Cyclophyllida, for example: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.Trematodes: from the class of the Digenea, for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Omithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.Nematodes: from the order of the Trichinellida, for example: Capillaria spp., Eucoleus spp., Paracapillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp. from the order of the Tylenchida, for example: Micronema spp., Parastrongyloides spp., Strongyloides spp. from the order of the Rhabditina, for example: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp.,Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.; Omithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafdaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Tricho strongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp. from the order of the Spirurida, for example: Acanthocheilonema spp., Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifdaria spp., Crassicauda spp., Dipetalonema spp., Dirofdaria spp., Dracunculus spp.; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp.;Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp., Stephanofdaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp.Acantocephala: from the order of the Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp.; from the order of the Moniliformida, for example: Moniliformis spp. from the order of the Polymorphida, for example: Filicollis spp.; from the order of the Echinorhynchida, for example: Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.Pentastoma: from the order of the Porocephalida, for example: Linguatula spp.
[0137] The compounds of the invention are in particular suitable to treat nematodes and trematodes. Typcial nematodes include Filariidae, Selariidcte. Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostonum, Oesophagostomrm, Charbertia, Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris and Parascaris. The trematodes include, in particular, the family of Fasciolideae, especially Fasciola hepatica.
[0138] A particular parasite to be treated and / or and controlled by the compounds of the invention is the heartworm (Dirofdaria immitis).
[0139] Subjects, in particular animals, in need of treatment or prevention include those already with the disorder or disease condition as well as those in which the disorder or disease condition is to be prevented.Pharmaceutical composition
[0140] The claimed invention also concerns a pharmaceutical composition for use in the prevention and / or treatment of a disease comprising at least one compound according the claimed invention and at least one further ingredient.
[0141] The claimed invention also also concerns a pharmaceutical composition for use in the long-term prevention and / or treatment of a disease comprising at least one compound according the claimed invention and at least one further ingredient.
[0142] In one embodiment, the pharmaceutical composition comprises at least one compound of general formula (I) of the present invention and at least one or more further active ingredients, in particular for the treatment and / or prevention of an endo- and / or ectoparasiticidal infection.
[0143] The term “active ingredient” as used herein refers to an ingredient that has a pharmaceutical effect, in particular a pharmaceutical effect related to the prevention and / or treatment of an endo- and / or ectoparasiticidal infection.
[0144] The term “endoparasite” as used herein is known to the skilled person and refers in particular to helminths.
[0145] The term “ectoparasite” as used herein is known to the skilled person and refers in particular to arthropods, particularly insects or acarids.
[0146] In one embodiment, the present invention covers a pharmaceutical composition for use in the prevention and / or treatment of a disease, including the long-term prevention and / or treatment of a disease comprising:• one or more first active ingredients, in particular compounds of general formula (I) as defined supra, and• one or more further active ingredients, in particular one or more endo- and / or ectoparasiticides.Such pharmaceutical compositions have the advantage that they are particularly efficient to prevent and / or treat endo- and ectoparasitic infections simulateneously.
[0147] Further active ingredients in form of endo- and / or ectoparasiticides are known by the skilled person and are described, for example, in the Pesticide Manual (“The Pesticide Manual” 16th Ed., British Crop Protection Council 2012) or can be searched in the internet (for example, http: / / www.alanwood.net / pesticides).
[0148] Examples of ectoparasiticides and / or endoparasiticides are insecticides, acaricides and nematicides, and include in particular:(1) Acetylcholinesterase (AChE) inhibitors, such as, for example, carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.(2) GABA-gated chloride channel blockers, such as, for example, cyclodiene-organochlorines, for example chlordane and endosulfan or phenylpyrazoles (fiproles), for example ethiprole and fipronil.(3) Sodium channel modulators, such as, for example, pyrethroids, e.g. acrinathrin, allethrin, d-cis- trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, biore smethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin [(lR)-trans-isomer], deltamethrin, empenthrin [(EZ)-(lR)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(lR)-trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [( 1R)- isomer)], tralomethrin and transfluthrin or DDT or methoxychlor.(4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, such as, for example, neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, such as, for example, spinosyns, e.g. spinetoram and spinosad.(6) Glutamate -gated chloride channel (GluCl) allosteric modulators, such as, for example, avermectins / milbemycins, for example abamectin, emamectin benzoate, lepimectin and milbemectin.(7) Juvenile hormone mimics, such as, for example juvenile hormone analogues, e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.(9) Modulators of Chordotonal Organs, such as, for example pymetrozine or flonicamid.(10) Mite growth inhibitors, such as, for example clofentezine, hexythiazox and diflovidazin or etoxazole.(12) Inhibitors of mitochondrial ATP synthase, such as, ATP disruptors such as, for example, diafenthiuron or organotin compounds, for example azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradifon.(13) Uncouplers of oxidative phosphorylation via disruption of the proton gradient, such as, for example, chlorfenapyr, DNOC and sulfluramid.(14) Nicotinic acetylcholine receptor channel blockers, such as, for example, bensultap, cartap hydrochloride, thiocylam, and thiosultap-sodium.(15) Inhibitors of chitin biosynthesis, type 0, such as, for example, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.(16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.(17) Moulting disruptor (in particular for Diptera, i.e. dipterans), such as, for example, cyromazine.(18) Ecdysone receptor agonists, such as, for example, chromafenozide, halofenozide, methoxyfenozide and tebufenozide.(19) Octopamine receptor agonists, such as, for example, amitraz.(20) Mitochondrial complex III electron transport inhibitors, such as, for example, hydramethylnone or acequinocyl or fluacrypyrim.(21) Mitochondrial complex I electron transport inhibitors, such as, for example from the group of the METI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).(22) Voltage -dependent sodium channel blockers, such as, for example indoxacarb or metaflumizone.(23) Inhibitors of acetyl CoA carboxylase, such as, for example, tetronic and tetramic acid derivatives, e.g. spirodiclofen, spiromesifen and spirotetramat.(25) Mitochondrial complex II electron transport inhibitors, such as, for example, 6eto-ketonitrile derivatives, e.g. cyenopyrafen and cyflumetofen and carboxanilides, such as, for example, pyflubumide.(28) Ryanodine receptor modulators, such as, for example, diamides, e.g. chlorantraniliprole, cyantraniliprole and flubendiamide, further active ingredients such as, for example, Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Chinomethionat, Chloroprallethrin, Cryolite, Cyclaniliprole, Cycloxaprid, Cyhalodiamide, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, epsilon- Momfluthrin, Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, hnidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tioxazafen, Thiofluoximate, Triflumezopyrim and iodomethane; furthermore preparations based on Bacillus firmus (1-1582, BioNeem, Votivo), and also the following compounds: l-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3-(trifluoromethyl)-lH-l,2,4-triazole- 5-amine (known from W02006 / 043635) (CAS 885026-50-6), {l'-[(2E)-3-(4-chlorophenyl)prop-2-en- 1 -yl] -5 -fluorospiro [indol-3 ,4'-piperidin] - 1 (2H)-yl } (2-chloropyridin-4-yl)methanone (known from W02003 / 106457) (CAS 637360-23-7), 2-chloro-N-[2-{l-[(2E)-3-(4-chlorophenyl)prop-2-en-l- yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from W02006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-l,8-diazaspiro[4.5]dec-3-en-2- one (known from WO 2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8- methoxy-2-oxo-l,8-diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate (known from EP2647626) (CAS1440516-42-6) , 4-(but-2-yn-l-yloxy)-6-(3,5-dimethylpiperidin-l-yl)-5-fluoropyrimidine (known from W02004 / 099160) (CAS 792914-58-0), PF1364 (known from JP2010 / 018586) (CAS 1204776-60-2), N-[(2E)-l-[(6-chloropyridin-3-yl)methyl]pyridin-2(lH)-ylidene]-2,2,2-trifluoroacetamide (known from WO2012 / 029672) (CAS 1363400-41-2), (3£)-3-[l-[(6-chloro-3-pyridyl)methyl]-2- pyridylidene]- 1,1,1 -trifluoro-propan-2 -one (known from WO2013 / 144213) (CAS 1461743-15-6), , N- [3 -(benzylcarbamoyl)-4-chlorophenyl] - 1 -methyl-3 -(pentafluoroethyl)-4-(trifluoromethyl)- 1H- pyrazole -5 -carboxamide (known from WO2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-A- [4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5- (trifluoromethyl)-3 -isoxazolyl] -2 -methyl -A-(cA- 1 -oxido-3 -thietanyl) -benzamide, 4-[5 -(3 ,5 - dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-A-(traM5-l-oxido-3-thietanyl) -benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2- methyl-A-(cA-l-oxido-3-thietanyl)benzamide (known from WO 2013 / 050317 Al) (CAS 1332628-83- 7), A-|3-chloro-l-(3-pyridinyl)-l / / -pyrazol-4-yl|-A-cthyl-3-|(3.3.3-trifluoropropyl)siilfinyl|- propanamide, (+)-A-|3-chloro-l-(3-pyridinyl)-l / / -pyrazol-4-yl|-A-cthyl-3-|(3.3.3-trifluoropropyl) sulfinyl] -propanamide and (-)-A-|3-chloro- l-(3-pyridinyl)-l / / -pyrazol-4-yl |-A-cthyl-3-|(3.3.3- trifluoropropyl)sulfmyl]-propanamide (known from WO 2013 / 162715 A2, WO 2013 / 162716 A2, US 2014 / 0213448 Al) (CAS 1477923-37-7), 5-[[(2£)-3-chloro-2-propen-l-yl]amino]-l-[2,6-dichloro- 4-(trifluoromethyl)phenyl] -4- [(trifluoromethyl)sulfmyl] - 17 / -py razolc-3 -carbonitrile (known from CN 101337937 A) (CAS 1105672-77-2), 3-bromo-A-[4-chloro-2-methyl-6-[(methylamino) thioxomethyl]phenyl]-l-(3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); W[4-chloro-2-[[(l,l-dimethylethyl)amino] carbonyl] -6-methylphenyl] - 1 -(3-chloro-2-pyridinyl)-3 -(fluoromethoxy)- 17 / -Py razolc-5 -carboxamide (known from WO 2012 / 034403 Al) (CAS 1268277-22-0), A-[2-(5-amino-l, 3, 4-thiadiazol-2-yl)-4- chloro-6-methylphenyl] -3 -bromo- 1 -(3 -chloro-2-pyridinyl)- 1 H-py razole-5 -carboxamide (known from WO 2011 / 085575 Al) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-l-yl)oxy] phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)-pyrimidine (known from CN 101337940 A) (CAS 1108184-52-6); (IE)- and 2(Z)-2-|2-(4-cyanophcnyl)-l-|3-(trifluoromcthyl)phcnyl |cthylidcnc|-A'-|4- (difhioromethoxy)phenyl]-hydrazinecarboxamide (known from CN 101715774 A) (CAS 1232543-85- 9); 3 -(2, 2-dichlorocthcnyl)-2.2-dimcthyl-4-( l / / -bcnzimidazol -2 -yl)phenyl -cyclopropanecarboxylic acid ester (known from CN 103524422 A) (CAS 1542271-46-4); (4aS)-7-chloro-2,5-dihydro-2- [ [(methoxycarbonyl) [4- [(trifluoromethyl)thio] phenyl] amino] carbonyl] -indeno [ 1 ,2-e ] [ 1 , 3 ,4] oxadiazinc-4a(3 / / )-carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69- 2); 6-deoxy-3-O-ethyl-2,4-di-O-methyl-, l-| '-|4-| I -|4-( I. l.2.2.2-pcntafluorocthoxy)phcnyl|-l / / -l.2.4-triazol-3-yl]phenyl]carbamate]-a-L-mannopyranose (known from US 2014 / 0275503 Al) (CAS 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin- 3-yl)-3-aza-bicyclo[3.2.1 ]octane (CAS 1253850-56-4), (8-awfi)-8-(2-cyclopropyhnethoxy-4- trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1 ]octane (CAS 933798-27-7), (8-5y«)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl- pyridazin-3-yl)-3-aza-bicyclo[3.2.1 ]octane (known from WO 2007040280 Al, WO 2007040282 Al) (CAS 934001-66-8), N-[3-chloro-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3-[(3,3,3- frifluoropropyl)thio]-propanamide (known from WO 2015 / 058021 Al, WO 2015 / 058028 Al) (CAS 1477919-27-9), N-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-l- (3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxamide (known from CN 103265527 A) (CAS 1452877- 50-7), 5-(l,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (known from WO 2013 / 115391 Al) (CAS 1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-l- methyl-l,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010 / 066780 Al, WO 2011 / 151146 Al) (CAS 1229023-34-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-l-methyl-l,8- diazaspiro [4.5] decane-2, 4-dione (known from WO 2014 / 187846 Al) (CAS 1638765-58-8), 3-(4- chloro-2,6-dimethylphenyl)-8-methoxy-l -methyl -2 -oxo-1, 8-diazaspiro[4.5]dec-3-en-4-yl-carbonic acid ethyl ester (known from WO 2010 / 066780 Al, WO 2011151146 Al) (CAS 1229023-00-0), N-[l- [(6-chloro-3-pyridinyl)methyl]-2(U7)-pyridinylidene]-2,2,2-trifluoro-acetamide (known from DE 3639877 Al, WO 2012029672 Al) (CAS 1363400-41-2), [N(£)]-N-[l-[(6-chloro-3-pyridinyl)methyl] -2(lH)-pyridinylidene]-2,2,2-trifluoro-acetamide, (known from WO 2016005276 Al) (CAS 1689566- 03-7), [N(Z)]-N-[l-[(6-chloro-3-pyridinyl)methyl]-2(lH)-pyridinylidene]-2,2,2-trifluoro-acetamide, (CAS 1702305-40-5), 3-ew o-3-[2-propoxy-4-(trifhioromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2- pyridinyl]oxy]-9-azabicyclo[3.3.1]nonane (known from WO 2011 / 105506 Al, WO 2016 / 133011 Al) (CAS 1332838-17-1).
[0149] Active ingredients with unknown or non-specific mode of action, e.g., fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplure, flutenzin, bromopropylate, cryolite;
[0150] Active ingredients from other classes, e.g. butacarb, dimetilan, cloethocarb, phosphocarb, pirimiphos (-ethyl), parathion (-ethyl), methacrifos, isopropyl o-salicylate, trichlorfon, sulprofos, propaphos, sebufos, pyridathion, prothoate, dichlofenthion, demeton-S- methyl sulphone, isazofos, cyanofenphos, dialifos, carbophenothion, autathiofos,aromfenvinfos (-methyl), azinphos (-ethyl), chlorpyrifos (-ethyl), fosmethilan, iodofenphos, dioxabenzofos, formothion, fonofos, flupyrazofos, fensulfothion, etrimfos; organochlorines, e.g. camphechlor, lindane, heptachlor; or phenylpyrazoles, e.g. acetoprole, pyrafluprole, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. sarolaner, afoxolaner, lotilaner, fluralaner; pyrethroids, e.g. (cis-, trans-), metofluthrin, profluthrin, flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protrifenbute, pyresmethrin, RU15525, terallethrin, cis-resmethrin, heptafluthrin, , bioethanomethrin, biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin, clocythrin, cyhalothrin (lambda-), chlovaporthrin, or halogenated carbonhydrogen compounds (HCHs); neonicotinoids, e.g. nithiazine; dicloromezotiaz, triflumezopyrim; macrocyclic lactones, e.g. nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin oxime; triprene, epofenonane, diofenolan;Biologicals, hormones or pheromones, for example natural products, e.g. thuringiensin, codlemone or neem components; dinitrophenols, e.g. dinocap, dinobuton, binapacryl; benzoylureas, e.g. fluazuron, penfluron; amidine derivatives, e.g. chlormebuform, cymiazole, demiditraz;
[0151] Bee hive varroa acaricides, for example organic acids, e.g. formic acid, oxalic acid. Non-limiting examples of insecticides and acaricides of particular interest for use in animal health are and include in particular [i.e. Mehlhorn et al Encyclpaedic Reference of Parasitology 4thedition (ISBN 978-3-662-43978-4)]:
[0152] Effectors at arthropod ligand gated chloride channels: chlordane, heptachlor, endoculfan. Dieldrin, bromocyclen, toxaphene, lindane, fipronil, pyriprole, sisapronil, afoxolaner, fluralaner, sarolaner, lotilaner, fluxametamide, broflanilide, avermectin, doramectin, eprinomectin, ivermectin, milbemycin, moxidectin, selamectin;
[0153] Modulators of arthropod octopaminergic receptors: amitraz, BTS27271, cymiazole, demiditraz;
[0154] Effectors at arthropod voltage-gated sodium channels: DDT, methoxychlor, metaflumizone, indoxacarb, cinerin I, cinerin II, jasmolin I, jasmolin II, pyrethrin I, pyrethrin II, allethrin, alphacypermethrin, bioallethrin, betacyfluthrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, etofenprox, fenvalerate, flucythrinate, flumethrin, halfenprox, permethrin, phenothrin, resmethrin, tau-fluvalinate, tetramethrin;
[0155] Effectors at arthropod nicotinic cholinergic synapses (acetylcholine esterase, acetylcholine receptors): bromoprypylate, bendiocarb, carbaryl, methomyl, promacyl, propoxur, azamethiphos, chlorfenvinphos, chlorpyrifos, coumaphos, cythioate, diazinon, diclorvos, dicrotophos, dimethoate, ethion, famphur, fenitrothion, fenthion, heptenophos, malathion, naled, phosmet, phoxim, phtalofos, propetamphos, temephos, tetrachlorvinphos, trichlorfon, imidacloprid, nitenpyram, dinotefuran, spinosad, spinetoram;
[0156] Effectors on arthropod development processes: cyromazine, dicyclanil, diflubenzuron, fluazuron, lufenuron, triflumuron, fenoxycarb, hydroprene, methoprene, pyriproxyfen, fenoxycarb, hydroprene, S-methoprene, pyriproxyfen.
[0157] Exemplary active ingredients from the group of endoparasiticides, as a further or other active ingredient in the present invention, include, without limitation, anthelmintically active compounds and antiprotozoal active compounds.
[0158] Anthelmintically active compounds, including, without limitation, the following nematicidally, trematicidally and / or cestoci dally active compounds:from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, ivermectin, emamectin, milbemycin; from the class of benzimidazoles and probenzimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimin, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole-sulphoxide, albendazole, flubendazole; from the class of depsipeptides, preferably cyclic depsipetides, in particular 24-membered cyclic depsipeptides, for example: emodepside, PF1022A; from the class of tetrahydropyrimidines, for example: morantel, pyrantel, oxantel; from the class of imidazothiazoles, for example: butamisole, levamisole, tetramisole; from the class of aminophenylamidines, for example: amidantel, deacylated amidantel (dAMD), tribendimidine; from the class of aminoacetonitriles, for example: monepantel; from the class of paraherquamides, for example: paraherquamide, derquantel; from the class of salicylanilides, for example: tribromsalan, bromoxanide, brotianide, clioxanide, closantel, niclosamide, oxyclozanide, rafoxanide; from the class of substituted phenols, for example: nitroxynil, bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan; from the class of organophosphates, for example: trichlorfon, naphthalofos, dichlorvos / DDVP, crufomate, coumaphos, haloxon; from the class of piperazinones / quinolines, for example: praziquantel, epsiprantel; from the class of piperazines, for example: piperazine, hydroxyzine;from the class of tetracyclines, for example: tetracyclin, chlorotetracycline, doxycyclin, oxytetracyclin, rolitetracyclin; from diverse other classes, for example: bunamidine, niridazole, resorantel, omphalotin, oltipraz, nitroscanate, nitroxynile, oxamniquine, mirasan, miracil, lucanthone, hycanthone, hetolin, emetine, diethylcarbamazine, dichlorophen, diamfenetide, clonazepam, bephenium, amoscanate, clorsulon.
[0159] Antiprotozoal active ingredients in the present invention, including, without limitation, the following active ingredients: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class of polylether ionophore, for example: monensin, salinomycin, maduramicin, narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones, for example: enrofloxacin, pradofloxacin; from the class of quinines, for example: chloroquine; from the class of pyrimidines, for example: pyrimethamine; from the class of sulfonamides, for example: sulfaquinoxaline, trimethoprim, sulfaclozin; from the class of thiamines, for example: amprolium; from the class of lincosamides, for example: clindamycin; from the class of carbanilides, for example: imidocarb; from the class of nitrofuranes, for example: nifurtimox; from the class of quinazolinone alkaloids, for example: halofuginon; from diverse other classes, for example: oxamniquin, paromomycin;from the class of vaccines or antigenes from microorganisms, for example: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus.
[0160] All named further active ingredients can, if their functional groups enable this, optionally form salts with suitable bases or acids.
[0161] In one embodiment, the pharmaceutical composition is a fixed combination.The term “fixed combination” is known to persons skilled in the art and is defined as a combination wherein, for example, a first active ingredient, such as one or more compounds of general formula (I) of the present invention, and a further active ingredient are present together in one unit dosage or in one single entity. One example of a “fixed combination” is a pharmaceutical composition wherein a first active ingredient and a further active ingredient are present in admixture for simultaneous administration, such as in a formulation. Another example of a “fixed combination” is a pharmaceutical composition wherein a first active ingredient and a further active ingredient are present in one unit without being in admixture.
[0162] In one embodiment, the pharmaceutical composition is a non-fixed combination or a kit-of-parts. The terms “non-fixed combination” or “kit-of-parts” are known to persons skilled in the art and are defined as a combination wherein a first active ingredient and a further active ingredient are present in more than one unit. One example of a non-fixed combination or kit-of-parts is a combination wherein the first active ingredient and the further active ingredient are present separately. It is possible for the components of the non-fixed combination or kit-of-parts to be administered separately, sequentially, simultaneously, concurrently or chronologically staggered.Subjects
[0163] According to the invention, the claimed compounds are used for the prevention and / or treatment of a disease in a subject in need thereof.
[0164] According to the invention, the claimed compounds are also used for the long-term prevention and / or treatment of a disease in a subject in need thereof.
[0165] Subject as used herein in particular means a human and a non-human animal. Unless expressly stated otherwise, the term “animal” as used herein refers to a “non-human animal”. Preferably, the non-human animal is an animal, in particular a farm animal, preferably selected from the group consisting of cattle, poultry, sheep, swine and companion animals such as cats and dogs. Preferably, the non-human animal is a mammal. Particularly preferably, the subject is a dog. The compounds for use according to the invention have particularly good long-lasting properties in preventing and / or treating a disease such as a helminthic infection in an animal.Use of the compounds
[0166] The claimed invention also concerns the use of a compound according to the invention for the prevention and / or treatment of a disease, in particular a helminthic infection in animals.
[0167] The claimed invention also concerns the use of a compound according to the invention for long-term prevention and / or treatment of a disease, in particular a helminthic infection in animals.
[0168] In one embodiment, the compound or the pharmaceutical composition for use according to the invention, as described supra, are used for the prevention and / or treatment of a disease, in particular of a helminthic infection, particularly of a gastro-intestinal and a extra- intestinal helminth infection, more particularly of a gastro-intestinal and a extra-intestinal infections with nematodes.
[0169] In one embodiment, the compound or the pharmaceutical composition for use according to the invention, as described supra, are used for the long-term prevention and / or treatment of a disease, in particular of a helminthic infection, particularly of a gastro-intestinaland a extra-intestinal helminth infection, more particularly of a gastro-intestinal and a extra- intestinal infections with nematodes.
[0170] In one embodiment, the compound or the pharmaceutical composition for use according to the invention, as described supra, are used for the preparation of a medicament suitable for the prevention and / or treatment of a disease, in particular of a helminthic infection, particularly of a gastro-intestinal and a extra-intestinal helminth infection, more particularly of a gastro-intestinal and a extra-intestinal infections with nematodes.
[0171] In one embodiment, the compound or the pharmaceutical composition for use according to the invention, as described supra, are used for the preparation of a medicament suitable for the long-term prevention and / or treatment of a disease, in particular of a helminthic infection, particularly of a gastro-intestinal and a extra-intestinal helminth infection, more particularly of a gastro-intestinal and a extra-intestinal infections with nematodes.
[0172] In one embodiment the compound or the pharmaceutical composition for use according to the invention, as described supra, are used as a long-term anthelmintic agent, in particular as a long-term nematicidal agent, a long-term platyhelminthicidal agent, a longterm acanthocephalicidal agent, or a long-term pentastomicidal agent.Method of treatment
[0173] The claimed invention also concerns a method for prevention and / or treatment of a disease comprising the administration of a compound or a pharmaceutical composition according to the invention at an effective dose to a subject in need thereof. The claimed invention also concerns a method for long-term prevention and / or treatment of a disease comprising the administration of a compound or a pharmaceutical composition according to the invention at an effective dose to a subject in need thereof.
[0174] A variety of administration routes are available for administering the compounds and the pharmaceutical composition according to the invention. The particular mode selected will depend upon the particular subject group selected, the age and general health status of thesubject, the particular condition being treated and the dosage required for therapeutic and / or prophylactic efficacy. The methods of this invention may be practiced using any mode of administration that produces effective levels of prevention and / or treatment of a disease, in particular a helminthic infection, without causing clinically unacceptable adverse effects.
[0175] The method comprises administering an effective amount of the compound or the pharmaceutical composition according to the invention to the subject in need thereof. Such effective amount is any amount that causes a prevention and / or treatment of a disease such as an helminthic infection. The skilled person knows methods to assess the presence and progression of an helminthic infection. A skilled person further knows that the effective amount depends on the subject such as the animal species, age, weight, stage of disease, as well as other factors known in the art.
[0176] It is possible for the compounds and the pharmaceutical composition according to the invention to have systemic and / or local activity. For this purpose, they can be administered in a suitable manner, such as, for example, via the oral, parenteral, pulmonary, nasal, sublingual, lingual, buccal, rectal, vaginal, dermal, transdermal, conjunctival, otic route or as an implant or stent.
[0177] It is possible for the compounds and the pharmaceutical composition for use according to the invention to be administered in suitable administration forms.
[0178] In one embodiment, the compound or the pharmaceutical composition for use according to the invention is administered orally. For oral administration, it is possible to formulate the compounds and the pharmaceutical composition according to the invention to dosage forms known in the art that deliver the compounds of the invention rapidly and / or in a modified manner, such as, for example, tablets (uncoated or coated tablets, for example with enteric or controlled release coatings that dissolve with a delay or are insoluble), orally- disintegrating tablets, films / wafers, films / lyophylisates, capsules (for example hard or soft gelatine capsules), sugar-coated tablets, granules, pellets, chewables (for example soft chewables), powders, emulsions, suspensions, aerosols or solutions. It is possible toincorporate the compounds and the pharmaceutical composition according to the invention in crystalline and / or amorphised and / or dissolved form into said dosage forms.
[0179] In one embodiment, the compound or the pharmaceutical composition for use according to the invention is administered parenterally. Parenteral administration can be effected with avoidance of an absorption step (for example intravenously, intraarterially, intracardially, intraspinally or intralumbally) or with inclusion of absorption (for example intramuscularly, subcutaneously, intracutaneously, percutaneously or intraperitoneally). In one embodiment, the compound or the pharmaceutical composition for use according to the invention is administered subcutanteously. Administration forms which are suitable for parenteral administration are, for example, preparations for injection and infusion in the form of solutions, suspensions, emulsions, lyophylisates or sterile powders.
[0180] In one embodiment, the compound or the pharmaceutical composition for use according to the invention is administered subcutaneously in a form enabling a sustained release of the compound or the active compound in the pharmaceutical composition. This has the advantage that a particularly efficient long-term effect regarding the prevention and / or treatment of a disease is achieved, in particular in the long-term prevention and / or treatment of an helminthic infection in an animal, preferably in a cat or a dog.
[0181] Other suitable administration routes are, for example, pharmaceutical forms for inhalation (inter alia powder inhalers, nebulizers), nasal drops, nasal solutions, nasal sprays; tablets / films / wafers / capsules for lingual, sublingual or buccal administration; suppositories; eye drops, eye ointments, eye baths, ocular inserts, ear drops, ear sprays, ear powders, earrinses, ear tampons; vaginal capsules, aqueous suspensions (lotions, mixturae agitandae), lipophilic suspensions, emulsions, ointments, creams, transdermal therapeutic systems (such as, for example, patches), milk, pastes, foams, spot-ons, dusting powders, implants or stents.
[0182] The compounds and the pharmaceutical composition according to the invention can be incorporated into suitable administration forms. This can be effected in a manner known by the skilled person, in particular by mixing with pharmaceutically suitable excipients.
[0183] In one embodiment, the total amount of the compound for use according to the invention is administered in ranges from about 0.001 mg / kg to about 200 mg / kg body weight per day, preferably from about 0.005 mg / kg to about 100 mg / kg body weight per day and most preferably from about 0.01 mg / kg to about 50 mg / kg body weight per day. These administration characteristics ensure that the prevention and / or treatment of a disease, in particular the prevention and / or treatment of an helminthic infection in animals, is particularly effective, also for long-term.
[0184] In one embodiment, the dosage for administration by injection, including intravenous, intramuscular, subcutaneous and parenteral injections, and use of infusion techniques is from 0.01 to 200 mg / kg of total body weight. In one embodiment, the dosage for rectal administration is from 0.01 to 200 mg / kg of total body weight. In one embodiment, the dosage for vaginal administration is from 0.01 to 200 mg / kg of total body weight.
[0185] In one embodiment, the dosage for topical administration is from 0.1 to 200 mg of total body weight. In one embodiment, the dosage for transdermal administration is 0.01 to 200 mg / kg of total body weight. In one embodiment, the dosage for administration by inhalation is from 0.01 to 100 mg / kg of total body weight.
[0186] In one embodiment, the compound or the pharmaceutical composition for use according to the invention is administered at most every 15 days, preferably at most once every month, more preferably at most once every one and a half months, even more preferably at most once every two months, and most preferably at most once every three months. In one embodiment, the compound or the pharmaceutical composition for use according to the invention is administered once every 15 days, preferably once every month, more preferably once every one and a half months, even more preferable once every two months, and most preferably once every three months. This has the advantage that an effective prevention and / or treatment of a disease, in particular of a helminthic infection in animals, is achieved while at the same time a convenient dosage regimen is applied, also for long-term.
[0187] In addition, "drug holidays" are possible, in which a subject is not dosed with a drug for a certain period of time. Such drug holidays can be beneficial to the overall balance between pharmacological effect and tolerability.Experimental section - General procedures1. General methods
[0188] All solvents used were commercially available and were used without further purification. Reactions were typically run using anhydrous solvents under an inert atmosphere of nitrogen.
[0189] Proton NMR spectra were recorded using a Bruker DMX300 (JH NMR: 300 MHz;13C NMR: 75 MHz), Bruker Avance III 400 (XH NMR: 400 MHz;13C NMR: 100 MHz) or Bruker 400 Ultrashield (' H NMR: 400 MHz;13C NMR: 100 MHz). All deuterated solvents contained typically 0.03% to 0.05% v / v tetramethylsilane, which was used as the reference signal (set at d 0.00 for both1H and13C). Chemical shifts (5) are displayed in parts per million [ppm]; the following abbreviations are used: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, br. = broad; coupling constants are displayed in Hertz [Hz],
[0190] Preparative reverse-phase HPLC was performed using Varian HPLC system. The column used was XB ridge Prep C18 OBD Column, 5 um, 19 x 150 mm. The instrument uses reverse-phase conditions (CHUN / water, containing 0.1% Ammonium hydrogen carbonate or formic acid).2. Analysis methodsLC-MS, Method AInstrument: SHIMADZU LCMS - 2020 - LCMS 2020 MS detector; Column: HALO 2.0 pm, 30 x 3.0 mm; eluent A: water + 0.05 vol % trifluoroacetic acid, eluent B: CH3CN + 0.05 vol % trifluoroacetic acid; gradient: assigned for each compound; flow 1.2 mL / min; temperature: 40°C; PDA scan: 190 - 400 nm.LC-MS, Method BInstrument: SHIMADZU LCMS - 2020 - LCMS 2020 MS detector; Column: Shim-pack XR-ODS 2.6 pm, 50 x 3.0 mm; eluent A: water + 0.05 vol % ammonium hydrogenocarbonate, eluent B: CH3CN; gradient: assigned for each compound; flow 1.2 mL / min; temperature: 40 °C; PDA scan: 190 - 400 nm.LC-MS, Method CInstrument: SHIMADZU LCMS - 2020 - LCMS 2020 MS detector; Column: Kinetex EVO C18 - 100A 2.6 pm, 30 x 3.0 mm; eluent A: water + 6.5 mM ammonium hydrogencarbonate, eluent B: CH3CN; gradient: assigned for each compound; flow 1.2 mL / min; temperature: 40 °C; PDA scan: 190 - 400 nm.LC-MS, Method DMS instrument type: Agilent Technologies 6130 Quadrupole LC-MS; HPLC instrument type: Agilent Technologies 1260 Infinity; column: Waters XSelect (Cl 8, 30x2.1mm, 3.5p); flow: 1 mL / min; column temp: 35°C; eluent A: 0.1% formic acid in acetonitrile; eluent B: 0.1% formic acid in water; lin. gradient: t=0 min 5% A, t=l .6 min 98% A, t=3 min 98% A; detection: DAD (220-320 nm); detection: MSD (ESI pos / neg) mass range: 100 - 800; detection: ELSD (PL-ELS 2100): gas flow 1.2 mL / min, gas temp: 70°C, neb: 50°C.LC-MS, Method EMS instrument type: Agilent Technologies LC / MSD SL; HPLC instrument type: Agilent Technologies 1100 Series; column: Waters XSelect (C18, 30x2.1mm, 3.5p); flow: 1 mL / min; column temp: 25°C, eluent A: 95% acetonitrile + 5% 10 mM ammonium bicarbonate in water, eluent B: 10 mM ammonium bicarbonate in water pH=9.0; lin. gradient: t=0 min 5% A, t=l .6 min 98% A, t=3 min 98% A; detection: DAD (220-320 nm); detection: MSD (ESI pos / neg) mass range: 100 - 800.LC-MS, Method FMS instrument type: Agilent Technologies LC / MSD SL; HPLC instrument type: Agilent Technologies 1100 Series; column: Waters XSelect (C18, 50x2.1mm, 3.5p; flow: 0.8 mL / min; column temp: 25°C; eluent A: 95% acetonitrile + 5% 10 mM ammonium bicarbonate in water; eluent B: 10 mM ammonium bicarbonate in water pH=9.0; lin. gradient: t=0 min 5% A, t=3.5 min 98% A, t=6 min 98% A; detection: DAD (220-320 nm); detection: MSD (ESI pos / neg) mass range: 100-800.NMR peak lists1H-NMR data of selected examples are written in form of 1H-NMR peak lists. To each signal peak are listed the d -value in ppm and the signal intensity in round brackets. Between the d-value - signal intensity pairs are semicolons or commas as delimiters.The peak list of an example has therefore the form:□di (intensity i); D d2 (intensity 2); ; Ddi (intensity 1); ; Ddn(intensityn) or□di (intensity 1); D d2 (intensity 2); ; Ddi (intensity 1); ; Ddn(intensityn)Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown. For calibrating chemical shift for ’H spectra, we use tetramethylsilane and / or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore, in NMR peak lists, tetramethylsilane peak can occur but not necessarily.The1H-NMR peak lists are similar to classical 1H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.
[0191] Additionally, they can show like classical ’H-NMR prints signals of solvents, stereoisomers of the target compounds, which are also object of the invention, and / or peaks of impurities.3. Synthesis of example 1.0Synthetic schemeExample 1.0: 8-(3,5-difluoro-2-(trifluoromethyl) phenyl)-7-fluoro-4-morpholino-N-(2,3,4a,8a- tetr ahydro-4H-benzo [b] -[1,4] oxazin-4-yl) quinoline-3-carboxamideStep 1: diethyl 2-(((2-bromo-3-fluorophenyl) amino) methylene) malonate (Int-1)A solution of 2-bromo-3 -fluoroaniline (130 g, 0.684 mol) and diethyl 2-(ethoxymethylene) propanedioate (177.52 g, 0.82 mol, 164.37 mL) in PhMe (1 L) was stirred at 110°C for 16 hours under nitrogen atmosphere and monitored by LCMS (The reaction was repeated five times, each batch was 130 g, total 650 g). The reaction mixture was concentrated under vacuum to remove PhMe. Then the mixture was poured into PE and the precipitate was collected by filtration. The filter cake was washed with PE and dried in vacuum to afford title compound (1.1 kg, 83% yield) as a white solid. LC-MS (Method A, 0.01-1.80 min 5-100% B, 1.80-1.82 min 5% B): Rt = 1.473 min; MS (ESIpos): m / z = 360 (M+H)+.Step 2: ethyl 8-bromo-7-fluoro-4-hydroxyquinoline-3-carboxylate (Int-2)A solution of diethyl 2-(((2-bromo-3 -fluorophenyl) amino) methylene) malonate (360 g, 0.93 mol) in PI12O (2.5 L) was stirred at 250°C for 1 h (The reaction was repeated three times, each batch was360 g, total 1.08 kg). The reaction mixture was cooled to room temperature and poured into PE, the precipitate was collected by filtration. The filter cake was washed with PE and dried in vacuum to afford title compound (750 g, 79% yield) as a white solid. LC-MS (Method A, 0.01-1.80 min 5-100% B, 1.80-1.82 min 5% B): Rt = 1.587 min; MS (ESIpos): m / z = 314 (M+H)+.Step 3: ethyl 4,8-dibromo-7-fluoroquinoline-3-carboxylate (Int-3)To a stirred solution of ethyl 8-bromo-7-fluoro-4-hydroxyquinoline-3-carboxylate (150 g, 444.12 mmol) in DMF (50 mL) and CH2CI2 (1.5 L) was slowly added POBr, (165.52 g, 577.35 mmol) in portions at 0°C under nitrogen atmosphere. Then the reaction mixture was stirred for 1 hour at rt and monitored by TLC. The reaction was quenched with ice sat.aq. NaHCOs. The mixture was adjusted pH to 7 and extracted with DCM. The combined organic layers were washed with NaCl saturated solution, dried over anhydrous Na2SC>4 and concentrated under vacuum to afford title compound (156 g, 91% yield) as a light-yellow solid. LC-MS (Method A, 0.01-1.80 min 5-100% B, 1.80-1.82 min 5% B): Rt = 1.472 min; MS (ESIpos): m / z = 376 (M+H)+.Step 4: ethyl 8-bromanyl-7-fluoranyl-4-morpholin-4-yl-quinoline-3-carboxylate (Int-4)To a stirred solution of ethyl 4,8-dibromo-7-fluoroquinoline-3-carboxylate (10 g, 26.7 mmol) in DMF (50 mL) was added DIEA (4. 12 g, 32 mmol) and morpholine (2.78 g, 32 mmol), the result mixture was stirred at 50 °C for 4 h and monitored by LCMS. The reaction mixture was poured into ice waterand the precipitate was collected by filtration. The filter cake was washed with water and dried to get a crude product. The crude was purified by trituration with EtOAc:PE (1 : 15) to title compound (9 g, 88% yield) as an off-white solid. LC-MS (Method A, 0.01-1.80 min 5-100% B, 1.80-1.82 min 5% B): Rt = 1.323 min; MS (ESIpos): m / z = 383 / 385 (M+H)+.Step 5: 4-nitro-3,4-dihydro-2H-benzo[b]-[l,4] oxazine (Int-5)Into a 40-mL round-bottom flask, was placed 3,4-dihydro-2H-benzo[b]-[l,4] oxazine (2 g, 14.8 mmol) in MeCN (16 mL), then added NaNCE (1.02 g, 14.8 mmol) in H2O (4 mb) at 0 °C, the resulting solution was stirred for 30 min at 0 °C. The resulting solution was allowed to slowly warm to rt. After 4 h, the resulting mixture was extracted with CH3CN, dried over anhydrous sodium sulfate. After filtration the title compound was obtained (1.5 g, 56% yield) as a yellow solid. LC-MS (Method A, 0.01-1.50 min 10-95% B, 1.50-2.00 min 95-95% B): Rt = 1.223 min; MS (ESIpos): m / z = 181 (M+H)+.Step 6: 2,3-dihydro-4H-benzo[b]-[l,4] oxazin-4-amine (Int-6)Into a 40-mL round-bottom flask, was placed 2,3-dihydro-4H-benzo[b]-[l,4]oxazin-4-amine (1.5 g, 8.3 mmol) in THF (15 mL), then added LiAlEL (5 mL, 10 mmol, 2 M in THF) at 0 °C, the resulting solution was allowed to slowly warm to rt for 6 h. The resulting mixture was quenched with Na2SO4- IOH2O (2 g) and diluted with DCM (20 mL). After filtration and concentration, the crude product was purified by silica column with DCM / MeOH = 10 / 1 to give title compound (700 mg, 56% yield) as a brown oil. LC-MS (Method B, 0.01-1.50 min 10-95% B, 1.50-2.00 min 95-95% B): Rt= 0.687 min; MS (ESIpos): m / z = 151 (M+H)+.Step 7: l-bromo-3,5-difluoro-2-(trifluoromethyl) benzene (int-7)Into a 8-mL round-bottom flask, was placed 3,5-difluoro-2-(trifluoromethyl) aniline (2 g, 10.15 mmol) in HBr (16 mL), Then added NaNCL (700 mg, 10. 15 mmol) at -5 °C, The resulting solution was stirred for 1 hour at -5°C, then CuBr (2.18 g, 15.22 mmol) was added to the mixture. The resulting solution was allowed to slowly warm to rt. After 4 hours, the resulting mixture was extracted with hexane, dried over anhydrous sodium sulfate. After filtration a solution of l-bromo-3,5-difluoro-2- (trifluoromethyl) benzene in hexane (80 mL) was obtained. The solution was directly used in the next step. GCMS (ESIpos) = 260.Step 8: (3,5-difluoro-2-(trifluoromethyl) phenyl) boronic acid (int-8)To a 100 mL 3 -necked round bottle equipped with thermometer was charged with l-bromo-3,5- difluoro-2-(trifluoromethyl) benzene (2.0 g, 7.66 mmol) and anhydrous THF (20 mL) and hexane (100 mL). Then the bottle was evacuated and filled with nitrogen three times. After cooling to -20 °C, a solution of isopropyl magnesium chloride in THF (5.7 mL, 2 M in THF, 11.49 mmol) was added slowly. Then the resulting mixture was stirred at -10 °C for 2 h. This was followed by addition of triisopropyl borate (389 mg, 2.07 mmol) in one portion. The resulting mixture was allowed to warm to room temperature. After stirring overnight, much white solid precipitated. The mixture was treated with IN HC1 (500 mL) and stirred for 1 h at room temperature. The resulting solution was extracted with EA, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to give title compound (800 mg, 46% yield) as a brown semi-solid. LC-MS (Method A): Rt= 0.856 min; MS (ESIpos): m / z = 225 (M-H)+.Step 9: ethyl 8-(3,5-difluoro-2-(trifluoromethyl) phenyl)-7-fluoro-4-morpholinoquinoline-3- carboxylate (Int-9)To a solution of ethyl 8-bromo-7-fluoro-4-morpholinoquinoline-3-carboxylate (200 mg, 521.90 pmol) in dioxane (8 mL), was added (3,5-difluoro-2-(trifluoromethyl) phenyl) boronic acid (413 mg, 1.83mmol), 3G XPhos Pd (44 mg, 52.19 pmol) and H2O (1 mL). The reaction mixture was stirred for 6 h at 100 °C under nitrogen atmosphere. After cooling to room temperature, the resulting mixture was treated with water and extracted with EtOAc, dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc: petroleum ether = 0-20%) to afford title compound (200 mg, 79% yield) as a yellow solid. LC-MS (Method B, 0.01-1.50 min 10-95% B, 1.50-2.00 min 95-95% B): Rt= 1.234 min; MS (ESIpos): m / z = 485 (M+H)+.Step 10: 8-(3,5-difluoro-2-(trifluoromethyl) phenyl)-7-fluoro-4-morpholinoquinoline-3- carboxylic acid (Int-10)To a solution of ethyl 8-(3,5-difluoro-2-(trifluoromethyl) phenyl)-7-fluoro-4-morpholinoquinoline-3- carboxylate (220 mg, 454.18 pmol) in THF (3 mL), was added MeOH (3 mL), H2O (3 mL) and LiOH (55 mg, 2.27 mmol). The reaction mixture was stirred for 18 h at rt. Upon completion of the reaction, the THF and MeOH were removed in vacuo and water was added, the pH value of the mixture was adjusted to 4 with 1 M HC1. The resulting mixture was extracted with EtOAc. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford title compound (170 mg, 82% yield) as yellow oil. LC-MS (Method A, 0.01-1.50 min 10-95% B, 1.50-2.00 min 95-95% B): Rt = 1.012 min; MS (ESIpos): m / z = 457 (M+H)+.Step 11: 8-(3,5-difluoro-2-(trifluoromethyl) phenyl)-7-fluoro-4-morpholino-N-(2,3,4a,8a- tetrahydro-4H-benzo[b]-[l,4] oxazin-4-yl) quinoline-3-carboxamide (example 1.0)To a solution of 8-(3,5-difluoro-2-(trifluoromethyl)phenyl)-7-fluoro-4-morpholinoquinoline-3-carboxylic acid (170 mg, 372.53 pmol) in DMF (5 mL), was added 2,3-dihydro-4H-benzo[b]- [l,4]oxazin-4-amine (57 mg, 372.53 pmol), HATU (170 mg, 447 pmol) and DIPEA (193 mg, 1.49 mmol, 259.55 pL). The resulting solution was stirred at rt. LCMS analysis showed reaction completed. Upon completion of the reaction, the resulting mixture was treated with water and extracted with EtOAc. The organic layers were combined, concentrated under vacuum. The residue purified by silica gel column chromatography (petroleum ether: EtOAc = 10: 1) and further purified by Prep-HPLC (Mobile Phase A: water(10 mmol / L NH4HCO3), Mobile Phase B: ACN; Gradient: 8% B to 45% B in 7 min) to afford 8-(3,5-difhioro-2-(trifluoromethyl) phenyl)-7-fluoro-4-morpholino-N-(2,3,4a,8a- tetrahydro-4H-benzo[b]-[l,4] oxazin-4-yl) quinoline -3 -carboxamide (42% yield) as a white solid.'H NMR (400 MHz, DMSO-d6) 5 10.74 (s, 1H), 8.82 (s, 1H), 8.39 (dd, 1H), 7.81 - 7.68 (m, 2H), 7.33 (d, 1H), 7.01 (d, 1H), 6.84 - 6.70 (m, 3H), 4.38 (t, 2H), 3.93 - 3.86 (m, 4H), 3.68 (s, 2H), 3.35 - 3.24 (m, 4H). LC-MS (Method C, 0.01-1.90 min 30-70% B, 1.90-2.00 min 70-95% B, 2.00-2.70 min 95% B): Rt = 1.683 min; MS (ESIpos): m / z = 589 (M-H)+.4. Synthesis of example 2.06Synthetic schemeExample 2.06: N-[(4S)-chroman-4-yl]-8-[2,3-difluoro-5-(trifluoromethyl) phenyl]-7-fluoro-4-(3- fluorocyclobutyl) quinoline-3-carboxamideStep 1: ethyl 8-bromo-4-(3,3-dimethoxy-l-(methoxycarbonyl) cyclobutyl)-7-fluoroquinoline-3- carboxylate (Int-11)To a stirred solution of methyl 3, 3 -di (methoxy) cyclobutene carboxylate (78.67 g, 452.14 mmol) in THF (800 mL) was added LiHMDS (493 mL, 493.36 mmol) dropwise at -78°C under nitrogen atmosphere. After 1 hour, to the above mixture was added ethyl 4,8-dibromo-7-fluoroquinoline-3- carboxylate (155 g, 411.14 mmol) in THF (200 mL) dropwise at -78°C. Then the mixture was stirred for 4 hours and monitored by TLC. The reaction was quenched with 10% aqueous NH4CI. The resulting mixture was extracted with EtOAc and water. The combined organic layers were washed with NaCl saturated solution, dried over anhydrous Na2SC>4 and concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with PE:EtOAc (17:3) to afford title compound (100 g, 41% yield) as a yellow solid. LC-MS (Method A, 0.01-1.80 min 5-100% B, 1.80- 1.82 min 5% B): Rt = 1.401 min; MS (ESIpos): m / z = 470 (M+H)+.Step 2: 8-bromo-7-fluoro-4-(3-oxocyclobutyl) quinoline-3-carboxylic acid (Int-12)A solution of ethyl 8-bromo-4-(3,3-dimethoxy-l-(methoxycarbonyl) cyclobutyl) -7-fluoroquinoline - 3-carboxylate (100 g, 212.64 mmol) and NaOH (42.52 g, 1.06 mol) in DME (300 mL) and H2O (200 mL) was stirred at 50°C for 12 hours under nitrogen atmosphere and monitored by LCMS. Then the mixture was adjusted pH to 2 by HC1 (4 N) and stirred at 50°C for 2 hours under nitrogen atmosphere The mixture was concentrated under vacuum to remove DME. The resulting mixture was filtered, the filter cake was washed with n-Hexane to get title compound (63 g, 70% yield) as a yellow solid. LC-MS (Method A, 0.01-1.80 min 5-100% B, 1.80-1.82 min 5% B): Rt =1.480 min; MS (ESIpos): m / z = 338 (M+H)+.Step 3: 8-bromo-N-[(4S)-chroman-4-yl]-7-fluoro-4-(3-oxocyclobutyl) quinoline-3-carboxamide (Int-13)To a stirred solution of 8-bromo-7-fluoro-4-(3-oxocyclobutyl) quinoline-3 -carboxylic acid (63 g, 186.32 mmol), (4S)-chroman-4-amine (29.19 g, 195.64 mmol), HATU (106.27 g, 279.48 mmol) in DMF (900 mL) was added DIEA (72.24 g, 558.96 mmol) dropwise at 0°C under nitrogen atmosphere. Then the mixture was stirred at rt for 2 hours and monitored by LCMS. The reaction mixture was poured into water and the precipitate was collected by filtration. The resulting mixture was filtered, the filter cake was washed with water to get a crude. The crude was purified by trituration with EtOAc:PE (1:5) to get title compound (80 g, 78% yield) as an off-white solid. LC-MS (Method B, 0.01-1.80 min 5-100% B, 1.80-1.82 min 5% B): Rt =1.271 min; MS (ESIpos): m / z = 469 (M+H)+.Step 4: l,2-difluoro-3-iodo-5-(trifluoromethyl)benzene (Int-14)To a solution of l,2-difhioro-4-(trifluoromethyl) benzene (60 g, 329.67 mmol) in CF3SO3H (250 mL) was slowly added NIS (81.6 g, 362.63 mmol) at 0°C under nitrogen atmosphere. Then the mixture was stirred at rt for 3-6 hours and monitored by GCMS. The reaction mixture was poured into ice water and extracted with n-Hexane 3 times. The combined organic layers were washed with NaCl saturated solution, dried over anhydrous Na2SC>4 and concentrated under vacuum below 15 °C to afford title compound (73 g, 237.02 mmol) as a light-yellow oil. GC-MS = 308.Step 5: (2,3-difluoro-5-(trifluoromethyl) phenyl) boronic acid (Int-15)To a stirred solution of 1 l,2-difluoro-3-iodo-5 -(trifluoromethyl) benzene (73 g, 237.02 mmol) in THF (250 mL) was slowly added iPrMgCl (2 M, 154.07 mL) at -40°C under N2. The reaction was stirred at -40°C for 30min. The reaction was monitored by TLC. TLC showed trace STM. To the above solution was slowly added B(OiPr)s (66.87 g, 355.53 mmol, 82.04 mL) (dissolved in 30mL THF) at -40°C. The reaction was left to return to rt and was stirred for 16 hr. The reaction was monitored by LCMS. The mixture was acidified to pH 3~4 with 4 N HC1 solution at 0°C. After stirring at rt for 2 hr and monitored by LCMS. The LCMS showed no significant change. The resulting mixture was extracted with EtOAc and H2O. The combined organic layers were washed with NaCl saturated solution, dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure to get title compound (60 g, crude) as a light-yellow oil. LC-MS (Method C, 0.01-1.80 min 10-95% B, 1.80- 1.82 min 10% B): Rt = 1.214 min; MS (ESIpos): m / z = 227 (M+H)+.Step 6: N-[(4S)-chroman-4-yl]-8-[2,3-difluoro-5-(trifluoromethyl) phenyl] -7-fluoro-4-(3- oxocyclobutyl) quinoline-3-carboxamide (Int-16)A solution of 8-bromo-N-[(4S)-chroman-4-yl]-7-fluoro-4-(3-oxocyclobutyl) quinoline-3 -carboxamide (80 g, 170.47 mmol), (2,3-difhroro-5-(trifhioromethyl) phenyl) boronic acid (96.27 g, 426.16 mmol), CsF (51.79 g, 340.93 mmol) and XPhos Pd G3 (14.43 g, 17.05 mmol) in PhMe (800 mL) and H2O (160 mL) was stirred at 100°C for 4 hours and monitored by LCMS. The mixture was concentrated under vacuum to remove PhMe. The residue was extracted with EtOAc and water. The combined organic layers were washed with NaCl saturated solution, dried over anhydrous Na2SO4 and concentrated under vacuum to get a crude. The crude was purified by silica gel column chromatography, eluted with PE:EtOAc (7:3). The residue was purified by trituration withhexane:EtOAc (10: 1) to get title compound (55 g, 48% yield) as a white solid. LC-MS (Method C, 0.01-1.80 min 10-95% B, 1.80-1.82 min 10% B): Rt = 1.214 min; MS (ESIpos): m / z = 571 (M+H)+.Step 7: N-[(4S)-chroman-4-yl]-8-[2,3-difluoro-5-(trifluoromethyl) phenyl] -7-fluoro-4-(3- hydroxycyclobutyl) quinoline-3-carboxamide (int-17)To a stirred solution of N-[(4S)-chroman-4-yl]-8-[2,3-difluoro-5-(trifluoromethyl) phenyl] -7-fluoro-4- (3 -oxocyclobutyl) quinoline-3 -carboxamide (55 g, 96.41 mmol) in THF (360 mL) and MeOH (120 mL) was added NaHE (3.65 g, 96.41 mmol) in portions at 0°C. Then the mixture was stirred at rt for 2 hours and monitored by LCMS. The mixture was concentrated under vacuum to remove MeOH. The resulting mixture was extracted with EtOAc and water. The combined organic layers were washed with NaCl saturated solution, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by trituration with EtOAc / PE (1:5) to get title compound (43 g, 66% yield) as a light-yellow solid. LC-MS (Method C, 0.01-1.80 min 10-95% B, 1.80-1.82 min 10% B): Rt = 1.214 min; MS (ESIpos): m / z = 573 (M+H)+.Step 8: N-[(4S)-chroman-4-yl]-8-[2,3-difluoro-5-(trifluoromethyl) phenyl] -7-fluoro-4-(3- fluorocyclobutyl) quinoline-3-carboxamide (Example 2.06)To a stirred solution of N-[(4S)-chroman-4-yl]-8-[2,3-difhioro-5-(trifluoromethyl) phenyl] -7-fluoro-4- (3 -hydroxy cyclobutyl) quinoline -3 -carboxamide (11 g, 16.33 mmol) in CH2CI2 (100 mL) was addedBAST (7.21 g, 32.66 mmol) (dissolved in 5 m DCM) dropwise at -60°C under nitrogen atmosphere. Then the mixture was stirred and warmed to 0°C for 2 hours and monitored by LCMS. (The reaction was repeated four times, each batch was 11 g, total 44 g). The reaction was quenched with cold sat.aq. NaHCOs solution. The resulting mixture was extracted with DCM and water. The combined organic layers were washed with NaCl saturated solution, dried over anhydrous Na2SC>4 and concentrated under vacuum. The residue was purified by reverse phase flash with the following conditions: [Column: C18 Column, 330; Mobile Phase A: Water(10 mmol / L NH4HCO3), Mobile Phase B: ACN; Flow rate: 100 mL / min; Gradient: 0% B to 40% B in 5 min, 40% B to 70% B in 30 min, 58% B 30 min; Wave Length: 254 / 220 nm; RT(min): 80. Then the crude product was further purified by trituration with EtOAc and hexane (1 / 15) to afford N-[(4S)-chroman-4-yl]-8-[2,3-difhroro-5-(trifhioromethyl) phenyl] -7-fluoro-4-(3 -fluorocyclobutyl) quinoline-3 -carboxamide (8.34 g, 22% yield) as a white solid.'HNMR (400 MHz, DMSO-d6) 5 9.18 (dd, J = 8.0, 3.2 Hz, 1H), 8.77 (d, J = 4.1 Hz, 1H), 8.40 - 8.26 (m, 1H), 8.15 (ddd, J = 9.8, 7.0, 2.2 Hz, 1H), 7.84 - 7.71 (m, 2H), 7.34 (d, J = 7.6 Hz, 1H), 7.17 (t, J = 7.8 Hz, 1H), 6.91 (t, J = 7.4 Hz, 1H), 6.80 (d, J = 8.2 Hz, 1H), 5.30 - 5.15 (m, 2H), 4.76 (p, J = 8.9 Hz, 1H), 4.28 - 4.23 (m, 2H), 2.98 - 2.86 (m, 4H), 2.25 - 2.05 (m, 2H). LC-MS (Method B, 0.01-1.70 min 50-80% B, 1.70-2.30 min 80%-95% B): Rt = 1.443 min; MS (ESIpos): m / z = 573 (M-H) .The compounds listed in Table 2 below were prepared in analogy to Example 2.06.Table 2: meta CFs lower phenyl ring (position 8 - quinoline)5. Synthesis of example 3.01Synthetic schemeExample 3.01: N-[(4S)-chroman-4-yl]-8-[2,3-difluoro-5-(l,l,2,2,2-pentafluoroethyl) phenyl]-7- fluoro-4-(3-fluorocyclobutyl) quinoline-3-carboxamideStep 1: l,2-difluoro-3-methoxy-5-(perfluoroethyl) benzene (lnt-18)To a solution of 5 -bromo- l,2-difluoro-3 -methoxybenzene (10 g, 44.84 mmol) and 2, 2, 3,3,3- pentakis(fluoranyl)propanoic acid, sodium hydride (10.06 g, ...
Claims
C l a i m s1. A compound of formula (I):according to alternative (i), (ii) (iii) or (iv), wherein according to alternative (i)A is AlA1 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Cs-Ce-halogenocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halog enoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R.2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy,Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl- CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R3 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, - SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, -NO2, -CONH2, -CH2-CONH2, -CHC=NCONH2, -COOH, Ci-C4-alkyl substituted with 1, 2 or 3 substituents selected from the group consisting of -CHO, -NO2, -SO2-Ci-C4-alkyl, and -SO-Ci-C4-alkyl,-Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,Cs-Ce -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -C00H, 4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -C0NH2, -CHO and -C00H,4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -C0NH2, -CHO and -C00H, 4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -C0NH2, -CHO and -C00H, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -C0NH2, -CHO and -C00H,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains lor 2 heteratoms selected from the group consisting of O, N, and S, wherein the 4- to 6-membered heteroaryl is connected to the rest of the molecule via a carbon atom and wherein the 4- to 6- membered heteroaryl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -C0NH2, -CHO and -C00H,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -C0NH2, -CHO and -C00H,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -C0NH2, - CHO, =0 and -C00H; is selected from the group consisting of a 5- or 6-membered aryl and 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; wherein according to alternative (ii)A is A2wherein # indicates the connection to the rest of the molecule;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Cs-Ce-halogenocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halog enoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl- CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R3 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxyhaving 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, - SC>2-Ci-C4-alkyl, and -SC>2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=N-SO2-(Ci-C4-alkyl), -CHC=NCONH2,-Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH,4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;R5hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, and -CHO;Re hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, and -CHO;R7hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, and -CHO;Q is selected from the group consisting of a 5- or 6-membered aryl and 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; according to alternative (iii)A3 wherein # indicates the connection to the rest of the molecule;Y is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, -CHO, -CO-O-Ci-C4-alkyl, -NH(Ci-C4-alkyl), -S-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and -SO2-Ci-C4-alkyl;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,Cs-Ce-halogenocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halog enoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SC>2-Ci-C4-alkyl, and -SC>2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl- CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R3 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, - SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, halogen, cyano, -NO2, -NH2, -N(Ci-C4-alkyl)(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci-C4- alkoxy), -CONH2, -CH2-CONH2, -CHC=NCONH2, -OH, -CHO, -COOH, Ci-C4-alkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -OH, -CHO, -COOH, -NO2, -NH2, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci- C4-alkyl), -SO2-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and Ci-C4-alkoxy, Ci-C4-haloalkyl having 1 to 9 halogen atoms, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl),-CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and Ci-C4- alkoxy,C3-C6 -cycloalkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, cyano, Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, -OH, -NO2, -NH2, -CONH2, and -COOH, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH, 4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, and is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituentsselected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -C00H;Q is selected from the group consisting of a 5- or 6-membered aryl and 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; wherein according to alternative (iv)A is A4A4 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-C00H, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Cs-Ce-halogenocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halog enoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-C0-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -S0-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -C00H, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy,Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl- CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SC>2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C3- Ce-halog enocycloalkyl having 1 to 11 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkyl-CO-, Ci-C4-halgenoalkyl-CO- having 1 to 9 halogen atoms, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)2, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, - SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=N-SO2-(Ci-C4-alkyl), -CHC=NCONH2, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH,4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Q is selected from the group consisting of a 5- or 6-membered aryl and 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or wherein according to alternative (v) the compound is selected from the group consisting of8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(l-oxidothietan-3- yl) quinoline-3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-7- fluoroquinoline -3 -carboxamide ;7-bromo-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l- dioxidothietan-3 -yl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-(l,l-dioxidothietan-3-yl)-7- fluoroquinoline -3 -carboxamide ;7-chloro-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l- dioxidothietan-3 -yl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)- 6, 7 -difluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-(l,l-dioxidothietan-3-yl)-6,7- difluoroquinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-7- (trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-6- fluoro-7-(trifluoromethyl) quinoline-3-carboxamide;(S)-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-(chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-6- (perfluoroethyl) quinoline -3 -carboxamide ;(S)-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-(chroman-4-yl)-4-(l,l-dioxidothietan-3-yl)-6- (perfluoropropyl) quino line-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-(2,3-dihydro-4H-benzo[b][l,4] oxazin-4-yl)-7- fluoro-4-(( lr,3r)-3-fluorocyclobutyl) quinoline -3 -carboxamide;4-((ls,3s)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-N-(2,3-dihydro-4H- benzo [b] [ 1 ,4] oxazin-4-yl) -7 -fluoroquinoline -3 -carboxamide ;4-((lr,3r)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-N-(2,3-dihydro-4H- benzo [b] [ 1 ,4] oxazin-4-yl) -7 -fluoroquinoline -3 -carboxamide ;8-(2,3-difluoro-5 -(trifluoromethyl) phenyl)-N-(2,3-dihydro-4H-benzo[b][l,4] oxazin-4-yl)-7-fluoro-4- ((lr,3r)-3-fluorocyclobutyl) quinoline-3-carboxamide;N-[(4S)-chroman-4-yl]-8-[2,3-difluoro-5-(trifluoromethyl) phenyl] -7-fluoro-4-(3 -fluorocyclobutyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(dicyanomethyl)-7- fluoroquinoline -3 -carboxamide ;8-(5-chloro-2-fluoro-3 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(2-chloro-5-fluoro-3-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-cyano-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -(trifluoromethoxy) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,5-dichloro-3-(trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;(S)-8-(2-chloro-3-(trifluoromethyl) phenyl)-N-(chroman-4-yl)-4-ethylquinoline-3-carboxamide;8-(2-chloro-3-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-ethyl-7-fluoroquinoline-3- carboxamide;(S)-8-(2-chloro-3-(trifluoromethyl) phenyl)-N-(chroman-4-yl)-4-morpholinoquinoline-3-carboxamide;(S)-8-(3-chloro-5-(trifluoromethyl) phenyl)-N-(chroman-4-yl)-7-fluoro-4-(3-fluoroazetidin-l-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-ethyl-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -propylquinoline-3 -carboxamide ;8-(2-chloro-3-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -(perfluoroethoxy) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(2-cyanopropan-2-yl)-7- fluoroquinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(3-cyanocyclobutyl)-7- fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-dichloro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- cyanocyclobutyl)-7-fluoroquinoline-3-carboxamide;N-((S)-chroman-4-yl)-8-(3,4-dichloro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -nitroquinoline-3 -carboxamide ;7-bromo-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;N-((S)-chroman-4-yl)-4-((ls,3R)-l-cyano-3-fluorocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7 -fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl)-8-(l-methyl-3-(trifluoromethyl)-lH- py razol-4-yl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl)-8-(l-methyl-3-(trifluoromethyl)-lH- py razol-5 -yl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl)-8-(l-(trifluoromethyl)-lH-pyrazol-4-yl) quinoline-3-carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((lr,3R,4S)-3,4- difluorocyclopentyl)-7-fluoroquinoline-3-carboxamide;8-(5-chloro-2-fluoro-3-(pentafluoro-16-sulfaneyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((ls,3R,4S)-3,4- difluorocyclopentyl)-7-fluoroquinoline-3-carboxamide;N-((S)-chroman-4-yl)-4-(2-cyanopropan-2-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7- fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-4-((lr,3S)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7- fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-4-((ls,3R)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7- fluoroquinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lR,2R)-l-cyano-2- (trifluoromethyl)cyclopropyl)-7-fluoroquinoline-3-carboxamide;8-(3-chloro-5-(difluoromethyl)-2-fluorophenyl)-N-((S)-chroman-4-yl)-4-(2-cyanopropan-2-yl)-7- fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((lr,3S)-l,3-difluorocyclobutyl)- 7 -fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((ls,3R)-l,3-difluorocyclobutyl)- 7 -fluoroquinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lR,3S)-3-fluoro-2,2- dimethylcyclobutyl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lS,3S)-3-fluoro-2,2- dimethylcyclobutyl) quinoline -3 -carboxamide ;N-[(4S)-chroman-4-yl]-8-[2,3-difluoro-5-(l,l,2,2,2-pentafluoroethyl) phenyl] -7-fluoro-4-(3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5-(perfluoropropan-2-yl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -(perfluoroethyl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(perfluoropropyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;7-chloro-N-((S)-chroman-4-yl)-8-(3,4-dichloro-5-(trifluoromethyl) phenyl)-4-((lR,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;7-chloro-N-((S)-chroman-4-yl)-8-(2,3-dichloro-5-(trifluoromethyl) phenyl)-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;7-chloro-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;8-[3-chloro-2-fluoro-5-(trifluoromethyl) phenyl]-N-[(4S)-chroman-4-yl]-6,7-difluoro-4-(3- fluorocyclobutyl) quinoline-3 -carboxamide ;N-((S)-chroman-4-yl)-4-((lr,3S)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-6,7- difluoroquinoline-3-carboxamide;N-((S)-chroman-4-yl)-4-((ls,3R)-3-cyanocyclobutyl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-6,7- difluoroquinoline-3-carboxamide;8-[3-chloro-2-fluoro-5-(trifluoromethyl) phenyl]-N-[(4S)-chroman-4-yl]-4-(3-fluorocyclobutyl)-7-(trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- fluorocyclobutyl) -7 -(trifluoromethyl) quinoline -3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((lr,3S)-3-fluorocyclobutyl)-7- (trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-6-fluoro-4-((lr,3S)-3- fluorocyclobutyl) -7 -(trifluoromethyl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l-cyanoethyl)-7- (trifluoromethyl) quinoline -3 -carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((ls,3R,4S)-3,4- difluorocyclopentyl)-7-(trifluoromethyl) quinoline -3 -carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((lr,3R,4S)-3,4- difluorocyclopentyl)-7-(trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(2-cyanopropan-2-yl)-7- (trifluoromethyl) quinoline -3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- cyanocyclobutyl)-7-(trifluoromethyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3-cyanocyclobutyl)-7 -(trifluoromethyl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((lr,3S)-3- fluorocyclobutyl) -7 -(perfluoropropyl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- fluorocyclobutyl) -6-(perfluoroethyl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((ls,3R)-3- fluorocyclobutyl) -6-(perfluoropropyl) quinoline -3 -carboxamide ;N-[(4S)-chroman-4-yl]-4-(3-fluorocyclobutyl)-8-[2-fluoro-5-(trifluoromethyl) phenyl]-6-( 1,1, 2,2,2- pentafluoroethyl) quinoline-3 -carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-4,4-difluoro-l,2,3,4-tetrahydronaphthalen-l- yl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl) quinoline-3-carboxamide;N-((lS)-3-bromo-4,4-difluoro-l,2,3,4-tetrahydronaphthalen-l-yl)-8-(3-chloro-2-fluoro-5- (trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3-fluorocyclobutyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4- morpholinoquinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(2-hydroxypyridin- 4-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(l,l,l- trifluoropropan-2-yl) quinoline-3-carboxamide;8-(2-chloro-5-fluoro-3-(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(l,l,l- trifluoropropan-2-yl) quinoline-3-carboxamide;4-(tert-butyl)-N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7-fluoroquinoline-3- carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(perfluoroethyl) quinoline-3-carboxamide;(S)-7-chloro-N-(chroman-4-yl)-8-(3,5-dichlorophenyl)-4-(methoxy(methyl)amino) quinoline-3- carboxamide;7-chloro-N-((S)-chroman-4-yl)-4-(3-fluoroazetidin-l-yl)-8-(2,3,5-trifluorophenyl) quinoline-3- carboxamide;7-chloro-N-((S)-chroman-4-yl)-8-(2,3-dichlorophenyl)-4-ethylquinoline-3-carboxamide;(S)-7-chloro-N-(chroman-4-yl)-8-(3,5-dichlorophenyl)-4-isopropylquinoline-3-carboxamide;N-((S)-chroman-4-yl)-6,7-difluoro-4-morpholino-8-(2,3,5-trifluorophenyl) quinoline-3-carboxamide;(S)-N-(chroman-4-yl)-8-(3,5-dichlorophenyl)-4-(dimethylamino)-6-(trifluoromethyl) quinoline-3- carboxamide;(S)-N-(chroman-4-yl)-8-(2,3-dichlorophenyl)-4-(dimethylamino)-5-(trifluoromethyl)quinoline-3- carboxamide;(S)-8-(5-chloro-2-fluorophenyl)-N-(chroman-4-yl)-4-(dimethylamino)-5-(trifluoromethyl)quinoline-3- carboxamide; and(S)-N-(Chroman-4-yl)-8-(3,5-dichlorophenyl)-4-(dimethylamino)-5-(trifluoromethyl) quinoline-3- carboxamide; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same. . A compound according to claim 1, wherein according to alternative (i)A is AlA1 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;FC is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, -NO2, -CONH2, -CH2-CONH2, -CHC=NCONH2, -COOH, Ci-C4-alkyl substituted with 1, 2 or 3 substituents selected from the group consisting of -CHO, -NO2, -SO2-Ci-C4-alkyl, and -SO-Ci-C4-alkyl, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH,4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, wherein the 4- to 6-membered heteroaryl is connected to the rest of the molecule via a carbon atom and wherein the 4- to 6- membered heteroaryl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH; is selected from the group consisting of a 5- or 6-membered aryl and a 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent;wherein according to alternative (ii)A is A2wherein # indicates the connection to the rest of the molecule;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=N-SO2-(Cl-C4-alkyl), -CHC=NCONH2, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl),-Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-Ce-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Rs hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, and -CHO; s hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, and -CHO;R? hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, and -CHO;Q is selected from the group consisting of a 5- or 6-membered aryl and a 5- or 6-membered heteroaryl,wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; according to alternative (iii)wherein # indicates the connection to the rest of the molecule;Y is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, -CHO, -CO-O-Ci-C4-alkyl, -NH(Ci-C4-alkyl), -S-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and -SO2-Ci-C4-alkyl;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1- -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, halogen, cyano, -NO2, -NH2, -N(Ci-C4-alkyl)(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci-C4- alkoxy), -CONH2, -CH2-CONH2, -CHC=NCONH2, -OH, -CHO, -COOH,Ci-C4-alkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -OH, -CHO, -COOH, -NO2, -NH2, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci- C4-alkyl), -SO2-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and Ci-C4-alkoxy, Ci-C4-haloalkyl having 1 to 9 halogen atoms, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, cyano, Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, -OH, -NO2, -NH2, -CONH2, and -COOH, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from thegroup consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, and is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Q is selected from the group consisting of a 5- or 6-membered aryl and a 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; wherein according to alternative (iv)A is A4A4 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,-SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=NCONH2,-Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl),-CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and Ci-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -N02, -NH2, -C0NH2, - CHO, =0 and -COOH; is selected from the group consisting of a 5- or 6-membered aryl and a5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of N, O and S, wherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, andwherein the 5- or 6-membered aryl or the 5- or 6-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
3. A compound according to claim 1 or 2, wherein according to alternative (i)A is AlA1 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SC>2-Ci-C4-alkyl, and -SC>2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, -NO2, -CONH2, -CH2-CONH2, -CHC=N-SO2-(Cl-C4-alkyl), -CHC=NCONH2, -COOH,Ci-C4-alkyl substituted with 1, 2 or 3 substituents selected from the group consisting of -CHO, -NO2, -SO2-Ci-C4-alkyl, and -SO-Ci-C4-alkyl, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, wherein the 4- to 6-membered heteroaryl is connected to the rest of the molecule via a carbon atom and wherein the 4- to 6- membered heteroaryl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Q is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered heteroaryl contains 2 heteratoms selected from the group consisting of N, O and S, preferably the two heteroatoms in the 5 -membered heteroaryl are N, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; wherein according to alternative (ii)A is A2wherein # indicates the connection to the rest of the molecule;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,-SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=N-SO2-(Cl-C4-alkyl), -CHC=NCONH2, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl),-CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and Ci-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -N02, -NH2, -C0NH2, - CHO, =0 and -COOH; hydrogen, halogen, -N02, -NH2, -OH, cyano, -COOH, and -CHO; hydrogen, halogen, -N02, -NH2, -OH, cyano, -COOH, and -CHO; hydrogen, halogen, -N02, -NH2, -OH, cyano, -COOH, and -CHO; is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5— membered heteroaryl contains 2 heteratoms selected from the group consisting of N, O and S, preferably the two heteroatoms in the 5 -membered heteroaryl are N, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituentsselected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; according to alternative (iii)wherein # indicates the connection to the rest of the molecule;Y is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, -CHO, -CO-O-Ci-C4-alkyl, -NH(Ci-C4-alkyl), -S-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and -SO2-Ci-C4-alkyl;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1- -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SC>2-Ci-C4-alkyl, and -SC>2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, halogen, cyano, -NO2, -NH2, -N(Ci-C4-alkyl)(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci-C4- alkoxy), -CONH2, -CH2-CONH2, -CHC=NCONH2, -OH, -CHO, -COOH,Ci-C4-alkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -OH, -CHO, -COOH, -NO2, -NH2, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci- C4-alkyl), -SO2-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and Ci-C4-alkoxy, Ci-C4-haloalkyl having 1 to 9 halogen atoms, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C6 -cycloalkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, cyano, Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, -OH, -NO2, -NH2, -CONH2, and -COOH, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 10-membered heterocycloalkyl, wherein the 4- to 10-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, and is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Q is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered heteroaryl contains 2 heteratoms selected from the group consisting of N, O and S, preferably the two heteroatoms in the 5 -membered heteroaryl are N, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; wherein according to alternative (iv)A is A4A4 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of NH, O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-C1-C4- halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,-SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci -C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-C1-C4 -alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, -S-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO-Ci-C4-alkyl, -SO-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SO2-Ci-C4-alkyl, and -SO2-Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=NCONH2,-Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, and -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl),-CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and Ci-C4- alkoxy,C3-C6 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-C6-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(CI-C4- alkyl), -N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 6-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -N02, -NH2, -C0NH2, - CHO, =0 and -COOH; is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered heteroaryl contains 2 heteratoms selected from the group consisting of N, O and S, preferably the two heteroatoms in the 5 -membered heteroaryl are N, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent;or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
4. A compound according to any one of claims 1-3, wherein according to alternative (i)A is AlA1 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, and -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms ;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, -NO2, -CONH2, -CH2-CONH2, -CHC=N-SO2-(Cl-C4-alkyl), -CHC=NCONH2, - COOH,Ci-C4-alkyl substituted with 1, 2 or 3 substituents selected from the group consisting of -CHO, -NO2, -SO2-Ci-C4-alkyl, and -SO-Ci-C4-alkyl,-Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2-Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C5 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(Ci-C4-alkyl), - N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 6-membered heterocycloalkyl, wherein the 4- to 6-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -CONH2, -CHO and -COOH,4- to 5-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 5 -membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 5-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -N02, -NH2, -CONH2, -CHO and -COOH,4- to 6-membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, wherein the 4- to 6-membered heteroaryl is connected to the rest of the molecule via a carbon atom and wherein the 4- to 6- membered heteroaryl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -C00H;Q is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered aryl is selected from the group consisting of pyrazole, imidazole, oxazole, isoxazole, isothiazole, thiazole, pyrazole, and imidazole, preferably the 5 -membered heteroaryl is selected from the group consisting of pyrazole, and imidazole, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; wherein according to alternative (ii)A is A2wherein # indicates the connection to the rest of the molecule;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -C00H, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, and -S-Ci-C4-alkyl;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -C00H, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=N-SO2-(Cl-C4-alkyl), -CHC=NCONH2, -Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2, -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C5 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(Ci-C4-alkyl), - N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 5 -membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 5 -membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5 -membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen,-OH, -N02, -NH2, -CONH2, -CHO and -COOH,4- to 5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Rs hydrogen, halogen;Rs hydrogen, halogen;R7 hydrogen, halogen;Q is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered aryl is selected from the group consisting of pyrazole, imidazole, oxazole, isoxazole, isothiazole, thiazole, pyrazole, and imidazole, preferably the 5 -membered heteroaryl is selected from the group consisting of pyrazole, and imidazole, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; according to alternative (iii)wherein # indicates the connection to the rest of the molecule;Y is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -COOH, Ci-C4-alkoxy, -CHO, and -CO-O-Ci-C4-alkyl;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, and -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of hydrogen, halogen, cyano, -NO2, -NH2, -N(Ci-C4-alkyl)(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci-C4- alkoxy), -CONH2, -CH2-CONH2, -CHC=NCONH2, -OH, -CHO, -COOH,Ci-C4-alkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -OH, -CHO, -COOH, -NO2, -NH2, -NH(Ci-C4-alkyl), -N(Ci-C4-alkyl)(Ci- C4-alkyl), -SO2-Ci-C4-alkyl, -SO-Ci-C4-alkyl, and Ci-C4-alkoxy, Ci-C4-haloalkyl having 1 to 9 halogen atoms, -Ci-C6-alkyl-C(=Li)-NH2wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2, -Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH, -Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C5 -cycloalkyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, cyano, Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, -OH, -NO2, -NH2, -CONH2, and -COOH, -N(Ci-C4-alkyl)(C4-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(Ci-C4-alkyl), - N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -COOH, 4- to 6-membered heterocycloalkyl, wherein the 4- to 6-membered heterocycloalkyl contains 1 or 2 heteroatoms selected from the group consisting of O, N and S, and wherein the 4- to 10-membered heterocycloalkyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -N02, -NH2, -C0NH2, -CHO and -COOH,4- to 5-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 5 -membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, 4- to 5-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 5 -membered heteroaryl wherein the 4- to 6-membered heteroaryl contains 1 or 2 heteratoms selected from the group consisting of O, N, and S, and is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4- to 5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -CONH2, - CHO, =0 and -COOH;Q is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered aryl is selected from the group consisting of pyrazole, imidazole, oxazole, isoxazole, isothiazole, thiazole, pyrazole, and imidazole, preferably the 5 -membered heteroaryl is selected from the group consisting of pyrazole, and imidazole, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; wherein according to alternative (iv)A is A4A4 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of O and S;Ri is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO,-COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms,Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, -S-Ci-C4-alkyl, and -S-Ci- C4-halogenoalkyl having 1 to 9 halogen atoms;R2 is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, -COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;Rs is selected from the group consisting of hydrogen, halogen, -NO2, -NH2, -OH, cyano, -CHO, - COOH, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=NCONH2,-Ci-C6-alkyl-C(=Li)-NH2 wherein Li is O or S and wherein Ci-C6-alkyl-C(=Li)-NH2 is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of halogen, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2, and -CSN(Ci-C4-alkyl)(Ci- C4-alkyl),-Ci-C6-alkyl-C(=L2)-NH(Ci-C4-alkyl) wherein L2 is O or S and wherein -Ci-C6-alkyl-C(=L2)- NH(Ci-C4-alkyl) is optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CONH(Ci-C4-alkyl), -CONH2, -CO-N(Ci-C4-alkyl)(Ci-C4-alkyl), -CSNH(Ci-C4-alkyl), -CSNH2, -CSN(Ci-C4-alkyl)(Ci-C4-alkyl), halogen, -NO2, -NH2, -OH, - CHO and -COOH,-Ci-C6-alkyl-C(=L3)-N(Ci-C4-alkyl)(Ci-C4-alkyl) wherein L3 is O or S and optionally substituted with 1, 2 or 3 subsituents selected from the group consisting of cyano, -CO-N(Ci- C4-alkyl)(Ci-C4-alkyl), -CO-NH(Ci-C4-alkyl), -CONH2, ), -CSNH(Ci-C4-alkyl), -CSNH2, - CSN(Ci-C4-alkyl)(Ci-C4-alkyl), -NO2, -NH2, -OH, -CHO, -COOH, halogen, and C1-C4- alkoxy,C3-C5 -cycloalkyl substituted with 1, 2 or 3 substituents selected from the group consisting of Ci-C4-haloalkyl having 1 to 7 halogen atoms, Ci-C4-alkyl, and -NO2, -N(Ci-C4-alkyl)(C4-cycloalkenone) wherein the C4-Ce-cycloalkenone is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -NH2, -NH(Ci-C4-alkyl), - N(Ci-C4-alkyl)2, Ci-C4-alkoxy, -OH, -NO2, -NH2, -CONH2, =0, and -C00H,4- to 5 -membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -C0NH2, -CHO and -C00H,4- to 5 -membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -C0NH2, -CHO and -C00H,5 -membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen,-OH, -NO2, -NH2, -C0NH2, -CHO and -C00H,4- to 5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -C0NH2, -CHO and -C00H,5- to 6-membered heterocycloalkanone wherein the 4- to 6-membered heterocycloalkanone contains 1 or 2 heteroatoms selected from the group consisting of N, S and O and wherein the 4- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, 3 or 4 substituents selected from the group consisting of Ci-C4-alkyl, halogen, -OH, -NO2, -NH2, -C0NH2, - CHO, =0 and -C00H;Q is selected from the group consisting of phenyl and a 5-membered heteroaryl, wherein the 5 -membered aryl is selected from the group consisting of pyrazole, imidazole, oxazole, isoxazole, isothiazole, thiazole, pyrazole, and imidazole, preferably the 5 -membered heteroaryl is selected from the group consisting of pyrazole, and imidazole, wherein the phenyl or the 5- membered heteroaryl is substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, -SF5, and Ci-C4-alkyl, and wherein the phenyl or the 5-membered heteroaryl is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
5. A compound according to any one of claims 1-4,wherein according to alternative (i)A is AlA1 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of O and S;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2,-NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, -NH2, - OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, brominc-NCK - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1,2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting of hydrogen, -NO2, -CONH2, -CH2-CONH2, -CHC=N-SO2-methyl, -CHC=NCONH2, -COOH, methyl, ethyl, propyl, isopropyl, tert-butyl, wherein the methyl, ethyl, propyl, isopropyl, or tert-butyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -CHO, -NO2, -SO2-methyl, and -SO-methyl,wherein# indicates the connection to the rest of the molecule,Li is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2,wherein# indicates the connection to the rest of the molecule,L2is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), -CONH(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl,wherein# indicates the connection to the rest of the molecule,L3 is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), -CONH(ethyl), -CON(methyl)(methyl), -CON(methyl)(ethyl), -CON(ethyl)(ethyl) and -CSNH2,Rs is selected from the group consisting of methyl and ethyl, cyclopropyl, cyclobutyl, cyclopentyl wherein the cyclopropyl, cyclobutyl and cyclopently are optionally substituted with 1, 2 or 3 substituents selected from the group consisting of methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, methyl, ethyl, and -NO2,wherein# indicates the connection to the rest of the molecule,Rio is selected from the group consisting of methyl and ethyl,R11 is selected from the group consisting of -NH2, -NH(methyl), -NH(ethyl), -NH(methyl)(methyl), -NH(ethyl)(methyl), -NH(ethyl)(ethyl), methoxy, ethoxy, -OH, -NO2, -NH2, -CONH2, and -COOH, azetidine, oxetane, thietane, pyrolidine, tetrahydrofuran, tetrahydriothiophene, piperidine, tetrahydropyrane, thiane, morpholine, 1,4-dioxine, 1,4-dithiane, piperazine, imidazolidine, 1,3 -dioxolane, or 1,3 -oxathiolane, wherein the azetidine, oxetane, thietane, pyrolidine, tetrahydrofuran, tetrahydriothiophene,piperidine, tetrahydropyrane, thiane, morpholine, 1,4-dioxine, 1,4-dithiane, piperazine, imidazolidine, 1,3 -dioxolane, or 1,3 -oxathiolane is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4-membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, fluorine, chlorine, bromine, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH, pyridine, pyrimidine, or pyrazine wherein pyridine, pyrimidine or pyrazine is is connected to the rest of the molecule via a carbon atom and wherein the pyridine, pyrimidine or pyrazine is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone selected from the group consisting ofwherein the 5- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, or 3 substituents selected from the group consisting of methyl, ethyl, fluorine, chlorine, -OH, -NO2, -NH2, -CONH2, -CHO, and -COOH;Q is selected from the group consisting of phenyl, pyrazole, and imidazole, wherein the phenyl, pyrazole or imidazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl, pyrazole or imidazole is substituted with at least one halogen or halogencontaining substituent; wherein according to alternative (ii)A is A2wherein # indicates the connection to the rest of the molecule;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2,-NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R.2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, -NH2, - OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, brominc-NCK - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=N-SO2-methyl, -CHC=NCONH2,wherein# indicates the connection to the rest of the molecule,Li is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2,wherein# indicates the connection to the rest of the molecule,L2 is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), - CONH(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl,wherein# indicates the connection to the rest of the molecule,L3 is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), - CONH(ethyl), -CON(methyl)(methyl), -CON(methyl)(ethyl), -CON(ethyl)(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl, cyclopropyl, cyclobutyl, cyclopentyl wherein the cyclopropyl, cyclobutyl and cyclopently are optionally substituted with 1, 2 or 3 substituents selected from the group consisting of methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, methyl, ethyl, and -NO2,wherein# indicates the connection to the rest of the molecule,Rio is selected from the group consisting of methyl and ethyl,R11 is selected from the group consisting of -NH2, -NH(methyl), -NH(ethyl),-NH(methyl)(methyl), -NH(ethyl)(methyl), -NH(ethyl)(ethyl), methoxy, ethoxy, -OH, -NO2, -NH2, -CONH2, and -COOH,4-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5 -membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of Ci-C4-alkyl, Ci-C4-haloalkyl having 1 to 7 halogen atoms, halogen,-OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone selected from the group consisting ofwherein the 5- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, or 3 substituents selected from the group consisting of methyl, ethyl, fluorine, chlorine, -OH, -NO2, -NH2, -CONH2, -CHO, and -COOH;R5hydrogen, fluorine, chlorine, bromine;Re hydrogen, fluorine, chlorine, bromine;R7hydrogen, fluorine, chlorine, bromine;Q is selected from the group consisting of phenyl, pyrazole, and imidazole, wherein the phenyl, pyrazole or imidazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from thegroup consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein phenyl, pyrazole or imidazole is substituted with at least one halogen or halogencontaining substituent; according to alternative (iii)A is A3A3 wherein # indicates the connection to the rest of the molecule;Y is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, - NH2, -OH, cyano, -COOH, methoxy, ethoxy, propxy, isopropxy, -CHO, and -CO-O-methyl and -CO-O-ethyl;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2,-NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, -NH2, - OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2,3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, brominc-NCK - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, -NO2, -NH2, -N(methyl)2, -N(ethyl)2, -N(methyl)(methoxy), -N(methyl)(ethoxy), -N(ethyl)(methoxy), -CONH2, -CH2-CONH2, -CHC=NCONH2, -OH, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, tert-butyl, wherein methyl, ethyl, propyl, isopropyl, or tertbutyl is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of cyano, -OH, -CHO, -COOH, -NO2, -NH2, -NH(methyl) -NH(ethyl), -N(methyl)2, -N(ethyl)2, -SO2-methyl, -SO-methyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, butyl substituted with 1, 2, 3, 4, 5, 6, 7, 8, or 9 halogen atoms selected from the group consisting of F, Cl, and Br, tert-butyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br,wherein indicates the connection to the rest of the molecule,R8is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -N02, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2.wherein# indicates the connection to the rest of the molecule,L2is O or SR8is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), - CONH(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl,wherein# indicates the connection to the rest of the molecule,L3 is O or SR8is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), - CONH(ethyl), -CON(methyl)(methyl), -CON(methyl)(ethyl), -CON(ethyl)(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl, cyclopropyl, cyclobutyl, cyclopentyl wherein cyclopropyl, cyclobutyl and cyclopently are optionally substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, , methyl, ethyl, -OH, -NO2, -NH2, -CONH2, and - COOH,wherein# indicates the connection to the rest of the molecule,Rio is selected from the group consisting of methyl and ethyl,Rn is selected from the group consisting of -NH2, -NH(methyl), -NH(ethyl), -NH(methyl)(methyl), -NH(ethyl)(methyl), -NH(ethyl)(ethyl), methoxy, ethoxy, -OH, - NO2, -NH2, -CONH2, and -COOH, azetidine, oxetane, thietane, pyrolidine, tetrahydrofuran, tetrahydriothiophene, piperidine, tetrahydropyrane, thiane, morpholine, 1,4-dioxine, 1,4-dithiane, piperazine, imidazolidine, 1,3 -dioxolane, or 1,3 -oxathiolane, wherein the azetidine, oxetane, thietane, pyrolidine, tetrahydrofuran, tetrahydriothiophene, piperidine, tetrahydropyrane, thiane, morpholine, 1,4-dioxine, 1,4-dithiane, piperazine, imidazolidine, 1,3 -dioxolane, or 1,3 -oxathiolane is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4-membered cyclic sulfone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4— membered cyclic sulfinyl optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, fluorine, chlorine, bromine, -OH, -NO2, - NH2, -CONH2, -CHO and -COOH, pyridine, pyrimidine, or pyrazine wherein the pyridine, pyrimidine or pyrazine is optionally substituted with 1, 2 or 3 substituents selected from the group consisting of -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of fluroine, chlorine, bromine, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone selected from the group consisting ofwherein the 5- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, or 3 substituents selected from the group consisting of methyl, ethyl, fluorine, chlorine, -OH, -NO2, -NH2, -CONH2, -CHO, and -COOH; is selected from the group consisting of phenyl, pyrazole, and imidazole, wherein the 6 phenyl, pyrazole or imidazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl, pyrazole or imidazole is substituted with at least one halogen or halogencontaining substituent; wherein according to alternative (iv)A is A4A4 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of O and S;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2,-NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, isopropyl, propyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, -NH2, - OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, brominc-NCK - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting of-NO2, -CH2-CONH2, -CHC=NCONH2,wherein indicates the connection to the rest of the molecule,Li is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, and -CSNH2,wherein indicates the connection to the rest of the molecule,L2is O or S,Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), - CONH(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl,wherein indicates the connection to the rest of the molecule,L3 is O or SRs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, -NO2, -NH2, -OH, -CHO, -COOH, cyano, -CONH2, -CONH(methyl), - CONH(ethyl), -CON(methyl)(methyl), -CON(methyl)(ethyl), -CON(ethyl)(ethyl) and -CSNH2,Rg is selected from the group consisting of methyl and ethyl,cyclopropyl, cyclobutyl, cyclopentyl wherein the cyclopropyl, cyclobutyl and cyclopently are optionally substituted with 1, 2 or 3 substituents selected from the group consisting of methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, methyl, ethyl, and -NO2,wherein# indicates the connection to the rest of the molecule,Rio is selected from the group consisting of methyl and ethyl,R11 is selected from the group consisting of -NH2, -NH(methyl), -NH(ethyl), -NH(methyl)(methyl), -NH(ethyl)(methyl), -NH(ethyl)(ethyl), methoxy, ethoxy, -OH, - NO2, -NH2, -CONH2, and -COOH,4-membered cyclic sulfone substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,4-membered cyclic sulfinyl substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5 -membered lactame optionally substituted with 1, 2 or 3 substituents selected from the group constisting of methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, fluorine, chlorine, bromine, -OH, -NO2, -NH2, - CONH2, -CHO and -COOH,5 -membered lactone optionally substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, -OH, -NO2, -NH2, -CONH2, -CHO and -COOH,5- to 6-membered heterocycloalkanone selected from the group consisting ofwherein the 5- to 6-membered heterocycloalkanone is optionally substituted with 1, 2, or 3 substituents selected from the group consisting of methyl, ethyl, fluorine, chlorine, -OH, -NO2,-NH2, -CONH2, -CHO, and -COOH;Q is selected from the group consisting of phenyl, pyrazole, and imidazole, wherein the 6 phenyl, pyrazole or imidazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl, pyrazole or imidazole is substituted with at least one halogen or halogencontaining substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
6. A compound according to any one of claims 1-5, wherein according to alternative (i)A is AlA1 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of O;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br and propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, -NO2, - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, and ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting ofwherein # indicates the connection to the rest of the molecule,Q is selected from the group consisting of phenyl, and pyrazole, wherein the 6 phenyl and pyrazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl and pyrazole is substituted with at least one halogen or halogen-containing substituent; wherein according to alternative (ii)A is A2wherein # indicates the connection to the rest of the molecule;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2,3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, -NO2, - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, and ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br; is selected from the group consisting ofwherein # indicates the connection to the rest of the molecule,Rs hydrogen, fluorine, chlorine, bromine;Re hydrogen, fluorine, chlorine, bromine;R? hydrogen, fluorine, chlorine, bromine;Q is selected from the group consisting of phenyl, and pyrazole, wherein the phenyl and pyrazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl and pyrazole is substituted with at least one halogen or halogencontaining substituent;according to alternative (iii)A is A3A3 wherein # indicates the connection to the rest of the molecule;Y is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, - NH2, -OH, cyano, -COOH, -CHO, and -CO-O-methyl and -CO-O-ethyl;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, -NO2, - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, and ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting of fluorine, chlorine, bromine, cyano, -NO2, -NH2, -N(methyl)2, -N(methyl)(methoxy), -CONH2,-CH2-CONH2, methyl, ethyl, propyl, isopropyl, tert-butyl,methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br,cyclopropyl, cyclobutyl, cyclopentyl,wherein # indicates the connection to the rest of the molecule,Q is selected from the group consisting of phenyl, and pyrazole, wherein the phenyl and pyrazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl and pyrazole is substituted with at least one halogen or halogen-containing substituent; wherein according to alternative (iv)A is A4A4 wherein # indicates the connection to the rest of the molecule;Xi is selected from the group consisting of O and S;Ri is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, methoxy, ethoxy, propoxy, isopropoxy, methoxy substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethoxy substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, isopropoxy substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and propoxysubstituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;R2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine -NO2, cyano, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br;Rs is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, -NO2, - NH2, -OH, cyano, -CHO, -COOH, methyl, ethyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, and ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br;R4 is selected from the group consisting of-NO2, -CH2-CONH2,wherein # indicates the connection to the rest of the molecule,Q is selected from the group consisting of phenyl, and pyrazole, wherein the phenyl and pyrazole is substituted with 1, 2 or 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methyl substituted with 1, 2 or 3 halogen atoms selected from the group consisting of F, Cl and Br, ethyl substituted with 1, 2, 3, 4 or 5 halogen atoms selected from the group consisting of F, Cl and Br, propyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, isopropyl substituted with 1, 2, 3, 4, 5, 6, or 7 halogen atoms selected from the group consisting of F, Cl and Br, and -SF5, and wherein the phenyl and pyrazole is substituted with at least one halogen or halogen-containing substituent; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
7. A compound according to any one of claims 1-6, wherein according to alternative (i) the compound is selected from the group consisting of8-(3, 5 -difluoro-2 -(trifluoromethyl) phenyl)-7-fluoro-4-morpholino-N-(2,3,4a,8a-tetrahydro-4H- benzo[b]-[l,4] oxazin-4-yl) quinoline -3 -carboxamide;N-(2,3-dihydro-4H-benzo[b][l,4] oxazin-4-yl)-8-(2-fhioro-5-(trifhioromethyl) phenyl)-4- morpholinoquinoline-3 -carboxamide ; andN-(2,3-dihydro-4H-benzo[b][l,4] oxazin-4-yl)-6,7-difhroro-4-morpholino-8-(2,3,5-trifluorophenyl) quinoline-3-carboxamide;wherein according to alternative (iii) the compound is selected from the group consisting of ethyl l-(8-(3-chloro-2-fhroro-5-(trifluoromethyl) phenyl)-7-fhroro-4-((lr,3r)-3-fluorocyclobutyl) quinoline-3 -carboxamido)- 1 ,2,3 ,4-tetrahydro- 1 ,4-methanonaphthalene-9-carboxylate; and8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-(3,4-dihydro-l,4-methanonaphthalen-l(2H)-yl)-7- fhroro-4-((lr,3r)-3-fluorocyclobutyl) quinoline -3 -carboxamide; or wherein according to alternative (iv) the compound is selected from the group consisting of4-(2-amino-l-cyano-2-oxoethyl)-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)-chroman-4- yl) -7 -fluoroquinoline-3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(methyl(2-(methylamino) -3 ,4-dioxocyclobut- 1 -en- 1 -yl)amino) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((S)-6- oxopiperidin-3-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((R)-5- oxotetrahydrofuran-3 -yl) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((2-methoxy-3 ,4- dioxocyclobut- 1 -en- 1 -yl)(methyl)amino) quinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((S)-2- oxopiperidin-4-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(2,6-dioxopiperidin-4-yl)-7- fluoroquinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-((R)-2- oxoimidazolidin-4-yl) quinoline -3 -carboxamide;N-((S)-chroman-4-yl)-8-(2,3-dichloro-5-(trifluoromethyl) phenyl)-7-fluoro-4-((lr,3S)-3- fluorocyclobutyl) quinoline-3 -carboxamide ;N-((S)-chroman-4-yl)-7-fhroro-4-((R)-l-methyl-5-oxopyrrolidin-3-yl)-8-(2,3,5-trifluorophenyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(6-oxo-l,2,3,6- tetrahydropyridin-4-yl) quinoline -3 -carboxamide;N-((S)-chroman-4-yl)-7-fluoro-4-(5-oxo-l-(trifluoromethyl) pyrrolidin-3-yl)-8-(2,3,5-trifluorophenyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(5-oxopyrrolidin-3- yl) quinoline-3 -carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7-fluoro-4-(l- (trifluoromethyl)cyclopropyl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((S)-2,5-dioxopyrrolidin-3- yl) -7 -fluoroquinoline-3 -carboxamide ;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-7-fluoro-4-(5-oxopyrrolidin-3-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(l-(trifluoromethyl)cyclopropyl) quinoline-3-carboxamide;4-(l-amino-2-methyl-l-oxopropan-2-yl)-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl) -N-((S)- chroman-4-yl)-7-fluoroquinoline-3-carboxamide;4-(l-amino-2-methyl-l-thioxopropan-2-yl)-8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-N-((S)- chroman-4-yl)-7-fluoroquinoline-3-carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-((R)-2,2-dimethyl-5- oxopyrrolidin-3 -yl) -7 -fluoroquinoline-3 -carboxamide ;2-(8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-3-(((S)-chroman-4-yl) carbamoyl)-7- fluoroquinolin-4-yl)-Nl,Nl,N3,N3-tetramethylmalonamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l-(dimethylamino)-2- methyl-l-oxopropan-2-yl)-7-fluoroquinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(2-methyl-l- (methylamino)-l-oxopropan-2-yl) quinoline-3-carboxamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l,3-dimethyl-2,4,6- trioxohexahydropyrimidin-5 -yl)-7 -fluoroquinoline -3 -carboxamide ;2-(8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-3-(((S)-chroman-4-yl) carbamoyl)-7- fluoroquinolin-4-yl)malonamide ;2-(8-(3-chloro-2-fluoro-5-(trifluoromethyl) phenyl)-3-(((S)-chroman-4-yl) carbamoyl)-7- fluoroquinolin-4-yl)-Nl,N3-dimethylmalonamide;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-(l -cyano- 1 -(methylsulfonyl) ethyl)-7 -fluoroquinoline -3 -carboxamide ;8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-7-fluoro-4-(2-methyl-l- (methylamino)-l-thioxopropan-2-yl) quinoline-3-carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-6,7-difluoro-4-((S)-5-oxopyrrolidin- 3-yl) quinoline-3-carboxamide;N-((S)-chroman-4-yl)-8-(2,3-difluoro-5-(trifluoromethyl) phenyl)-4-(l,l-dioxidothietan-3-yl)-7- (trifluoromethyl) quinoline -3 -carboxamide; and8-(3-chloro-2-fluoro-5 -(trifluoromethyl) phenyl)-N-((S)-chroman-4-yl)-4-((S)- cyano(methylsulfonyl)methyl)-7-(trifluoromethyl) quinoline-3-carboxamide; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of the same.
8. A compound according to any one of claims 1 to 8, for use in the prevention and / or treatment of a disease.
9. A compound according to any one of claims 1 to 8, for use in the long-term prevention and / or treatment of a disease.
10. Pharmaceutical composition for use in the prevention and / or treatment of a disease, comprising at least one compound according to any one of claims 1 to 8 and at least one further ingredient.11 . Pharmaceutical composition for use in the long-term prevention and / or treatment of a disease, comprising at least one compound according to any one of claims 1 to 8 and at least one further ingredient.
12. Compound for use according according to claim 8 or 9 or the pharmaceutical composition according to claim 10 or 11, wherein the disease is a helminithic infection.
13. Compound for use accordingto any one of claims 8, 9 or 12 or the pharmaceutical composition according to claim 10, 11 or 12, wherein the compound is used for the prevention and / or treatment of a disease in an animal, preferably in a companion animal, most preferably in a cat or a dog, and most preferably in a dog.
14. Compound for use according to any one of claims 9, 12 or 13 the pharmaceutical composition for use according to any one of claims 11, 12 or 13, wherein the compound has- a half-life of at least 5 days, preferably at least 10 days, more preferably at least 15 days, and most preferably at least 20 days; and / or- a plasma clearance of less than 0.2 L / h / kg, preferably less than 0.15 L / h / kg and most preferably less than 0.1 L / h / kg.
15. Compound for use according to any one of claims 9, 12, 13 or 14 or the pharmaceutical composition for use according to any one of claims 11, 12, 13 or 14, wherein the “long-term prevention and / or treatment of a disease” means that the compound prevents and / or treats the onset of a disease occurring at least 15 days after its administration, preferably at least one month after its administration, more preferably at least one and a half months after its administration, even more preferably at least two months after its administration, and most preferably at least three months after its administration.