Isoxazoline insecticide

Abstract

The present invention provides compounds of formula (I) and pharmaceutical compositions and methods of their use that are useful for the long-lasting treatment and control of pests (e.g., fleas and ticks) in companion animals and livestock. [Formula 1] TIFF2024523313000076.tif50152

Description

[Technical field]

[0001] This invention relates to medicinal chemistry, pharmacology, and veterinary and human medicine. [Background technology]

[0002] Aryl isoxazolines are used in agriculture, forestry, turf, household, wood products, nursery crop protection and veterinary fields.Veterinary fields include companion animals and livestock, including fish.For example, such inhibitors are disclosed in WO2005 / 085216, WO2007 / 079162, US2007 / 066617, US20130131017, WO2009 / 002809, WO2009 / 112275, WO2010 / 003923, WO2010 / 070068, WO2012 / 120399, WO2013 / 079407 and WO2021 / 127188.

[0003] In many applications, long-lasting efficacy against pests is desirable. Long-lasting protection is particularly important for companion animals (e.g., dogs and cats, but also mice, guinea pigs, ferrets, rabbits) and farm animals (e.g., cattle, sheep, pigs) and fish (especially salmon and sea bass). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] WO2005 / 085216 [Patent Document 2] WO2007 / 079162 [Patent Document 3] US2007 / 066617 [Patent Document 4] US20130131017 [Patent Document 5] WO2009 / 002809 [Patent Document 6] WO2009 / 112275 [Patent Document 7] WO2010 / 003923 [Patent Document 8] WO2010 / 070068 [Patent Document 9] WO2012 / 120399 [Patent Document 10] WO2013 / 079407 [Patent Document 11] WO2021 / 127188 Summary of the Invention [Problem to be solved by the invention]

[0005] The present invention relates to compounds of formula (I) having long half-lives and their use in the control of ectoparasites in companion and livestock animals, particularly warm-blooded animals, especially dogs, cats and cattle. In many cases, compounds of formula (I) provide a long duration of action of several months after a single oral dose or injection.

[0006] The present invention further provides compounds of formula (I) that effectively treat and / or control ectoparasites in companion animals and livestock. [Means for solving the problem]

[0007] In one embodiment, the present invention provides a method for the preparation of a compound of formula (I): [ka] [During the ceremony, A1 is selected from the group consisting of CF3, CHF2, CH2F and CF2CF3; A2 is O or S; R1 is selected from the group consisting of hydrogen and halogen; R2 is selected from the group consisting of hydrogen, halogen, difluoromethyl and trifluoromethyl; R3 is selected from the group consisting of hydrogen, halogen and trifluoromethyl; R4 is selected from the group consisting of hydrogen, halogen, difluoromethyl and trifluoromethyl; R5 is selected from the group consisting of hydrogen and halogen; however, R1 can be hydrogen only if R2 is trifluoromethyl, difluoromethyl or bromo; R5 can be hydrogen only if R4 is trifluoromethyl or bromo; R3 can be hydrogen only if one of R2 or R4 is either trifluoromethyl, difluoromethyl, or bromo; R1, R3 and R5 cannot all be hydrogen when R2 and R4 are trifluoromethyl; And, At most three of R1, R2, R3, R4 and R5 are hydrogen; Q is the following [ka] selected from the group consisting of; Where: p is 0, 1 or 2; q is 0, 1, 2 or 3; r is 0 or 1; s is 0, 1 or 2; t is 0 or 1; R6, at each occurrence, is independently selected from the group consisting of: halogen; cyano; nitro; hydroxyl; -NH2; -NH(C1-C4 alkyl); -N(C1-C4 alkyl)2; C2-C5-alkoxycarbonyl; C1-C6-alkyl, where alkyl is halogen, cyano, nitro, hydroxyl, oxo, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl and and -SO2C1-C4 alkyl; C1-C6-alkoxy (wherein the alkoxy is selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, and -SO2C1-C4 alkyl). -NR8C(O)(C1-C4 alkyl) (which is optionally substituted on the C1-C4 alkyl with 1-5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl) and -N(C1-C4 alkyl)2, where R8 is selected from hydrogen and C1-C4 alkyl; -C(O)NR8(C1-C4 alkyl), which is optionally substituted on the C1-C4 alkyl with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl) and -N(C1-C4 alkyl)2, where R8 is independently selected from the group consisting of hydrogen and C1-C4 alkyl;-SC1-C6 alkyl (wherein the alkyl is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl) and -N(C1-C4 alkyl)2); and -S(O)C1-C6 alkyl (wherein the alkyl is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl) and -N(C1-C4 alkyl)2); R7, at each occurrence, is independently selected from the group consisting of oxo, C1-C4 alkyl, and C3-C6 cycloalkyl; A3 is O or S; A4 is CH or N; A5 is CH or N; A6 is CH or N; A7 is CH 2 O, S, a bond or N; A8 is CH 2 O, S, a bond or N; A9 is CH or N; A 10 is CH or N; A 11 is CH or N; A 12 is CH or N; A 13 is CH or N; A 14 is CH or N; A 15 is CH or N; A 16 is NR, O, or S, where R is selected from the group consisting of hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl; W1 is -O-, -S-, -NR9-, -NC(O)R 10 -, -CH2-, and -C(O)-; W2 is -O-, -S-, -NR9-, -NC(O)R 10 -, -CH2-, and -C(O)-; however, W1 is -O-, -S-, -NR9- or -NC(O)R 10 -, W2 is -CH2- or -C(O)-; W2 is -O-, -S-, -NR9- or -NC(O)R 10 -, W1 is -CH2- or -C(O)-; W3 is selected from the group consisting of absent, -O-, -S-, -S(O)-, -S(O)2-, -NR9-, -CH-, -N-, -CH2-, and -C(O)-; W4 is selected from the group consisting of absent, -O-, -S-, -S(O)-, -S(O)2-, -NR9-, -CH-, -N-, -CH2-, and -C(O)-; W5 is selected from the group consisting of absent, -O-, -S-, -S(O)-, -S(O)2-, -NR9-, -CH-, -N-, -CH2-, and -C(O)-; W6 is selected from the group consisting of absent, -O-, -S-, -S(O)-, -S(O)2-, -NR9-, -CH-, -N-, -CH2-, and -C(O)-; wherein the bond between W1, W2, W3 and W4 can be a single bond or a double bond; however, (i) no more than two of W1, W2, W3, and W4 are present; (ii) no more than two of W1, W2, W3 and W4 are -O-, -S-, -S(O)-, -S(O)2-, -NR9- or -C(O)-; (iii) when two of W1, W2, W3 and W4 are -O- and / or -S-, there is at least one carbon atom between them; (iv) when W1, W2, W3 or W4 is -CH- and / or -NR9-, a double bond is formed in the ring formed by W1, W2, W3 and W4; R9, at each occurrence, is independently selected from the group consisting of hydrogen and C1-C6-alkyl, where the alkyl is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, and -SO2C1-C4 alkyl; R 10 is independently selected at each occurrence from the group consisting of oxo, C1-C4 alkyl, and C3-C6 cycloalkyl; X is a 5-10 membered heteroaryl having 1 or 2 heteroatoms selected from the group of O, S, and N; wherein the carbon of the 5-10 membered heteroaryl is selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C4 alkyl (wherein the alkyl is halogen, cyano, hydroxyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, and and -C(O)NH-C1-C6 haloalkyl), C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, and -C(O)NH-C1-C6 haloalkyl; wherein any N in said heteroaryl may be substituted, as permitted by valence, with a substituent selected from the group consisting of hydrogen, C1-C4 alkyl (wherein said alkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, acetylenyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl and -C(O)NH-C1-C6 haloalkyl) and C3-C6 cycloalkyl; Or, X is [ka] selected from the group consisting of; Where: R 11 is selected from the group consisting of hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C4-C7 alkycycloalkyl, C2-C7 alkylcarbonyl, C2-C5 alkoxycarbonyl, C2-C6 alkenyl, and C2-C6 alkynyl; W is selected from the group consisting of: (i) hydrogen, (ii) C1-C6 alkyl (wherein the alkyl is halogen; cyano; hydroxyl; oxo; C1-C4 alkoxy; C3-C6 cycloalkyl (wherein the cycloalkyl is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen and cyano); acetylenyl; -NH2; C1-C7 aminocarbonyl; -NH(C1-C4 alkyl); -N(C1-C4 alkyl)2; -SC1-C4 alkyl; -S(O)C1-C4 alkyl; -SO2C1-C4 alkyl; -C (O)NH-C3-C6 cycloalkyl (wherein this is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, hydroxyl, cyano, and C1-C4 alkyl (wherein the alkyl is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C1-C4 alkoxy, C3-C6 cycloalkyl, and -NH2); -C(O)NH-C1-C6 alkyl (wherein this is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C1-C4 alkoxy, C3-C6 cycloalkyl, and -NH2); -C(O)NH-C1-C6 cyanoalkyl, which may be substituted with 1 to 5 substituents independently selected from the group consisting of aryl, C1-C4 alkoxy, C3-C6 cycloalkyl, and -NH2; -C(O)NH-C1-C6 cyanoalkyl, which may be substituted with 1 to 3 halogens; -C(O)NH-C1-C6 haloalkyl; -C(O)-4 to 7 membered heterocycloalkyl, which is bonded through a nitrogen and has 1 or 2 other heteroatoms selected from the group consisting of O, S, and N. wherein the carbon of the 4-7 membered heterocycloalkyl is halogen, cyano, nitro, hydroxyl, oxo, -NH2, C1-C7 aminocarbonyl, C1-C4 alkyl (wherein the alkyl is halogen, cyano, hydroxyl, acetylenyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl,and C3-C6 cycloalkyl, where any other N in the 4-7 membered heterocycloalkyl is, as far as valence permits, hydrogen, -NH2, C1-C7 aminocarbonyl, -SO2C1-C4 alkyl, -SO2C1-C4 haloalkyl, and C1-C4 alkyl (wherein the alkyl is halogen, cyano, hydroxyl, phenyl ... aryl, acetylenyl, C1-C4 alkoxy, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl and -C(O)NH-C1-C6 haloalkyl); 5-10 membered heteroaryl (wherein the heteroaryl is selected from the group consisting of O, S and N; and 1 or 2 heteroatoms selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C4 alkyl (wherein the alkyl is selected from the group consisting of halogen, cyano, hydroxyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, and - and C(O)NH-C1-C6 haloalkyl), C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, and -C(O)NH-C3-C6 cycloalkyl, where any N of the heteroaryl may be substituted, as far as valence permits, with hydrogen, C1-C4 alkyl (wherein the alkyl isand C3-C6 cycloalkyl, optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, acetylenyl, oxo, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 alkyl), and substituted with a substituent selected from the group consisting of C3-C6 cycloalkyl. wherein any S in the heteroaryl may be substituted with one or two oxygen atoms; phenyl, wherein the phenyl may be substituted with one to three substituents selected from the group consisting of halogen, C1-C4 alkyl, cyano, and hydroxyl; C3-C6 cycloalkyl, wherein the cycloalkyl is halogen, cyano, hydroxyl, oxo, C1-C4 alkoxy, C1-C4 alkyl, wherein the alkyl may be substituted with one to three groups selected from the group consisting of halogen and cyano; C1-C4 haloa, alkyl, -NH, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, -C(O)NH-C1-C6 haloalkyl, C2-C6 alkenyl, and C2-C6 alkynyl; and 4-7 membered heterocycloalkyl (wherein the heterocycloalkyl is selected from the group consisting of O, and having 1 or 2 heteroatoms selected from the group of S, B, and N, wherein the heterocycloalkyl may be benzo-fused, and wherein the carbons of the 4-7 membered heterocycloalkyl or the optionally benzo-fused 4-7 membered heterocycloalkyl are selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, and C1-C4 alkyl, wherein the alkyl is halogen, cyano, hydroxyl, acetylenyl, oxo, C1-C4 alkoxy, C3-C6 cycloalkyl, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl),and each of the 4- to 7-membered heteroaryl groups may be substituted with 1 to 4 substituents independently selected from the group consisting of -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, and -C(O)NH-C1-C6 haloalkyl, wherein the 4- to 7-membered heteroaryl group may be substituted with 1 to 5 substituents independently selected from the group consisting of -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, and -C(O)NH-C1-C6 haloalkyl, Any B in the 4- to 7-membered heterocycloalkyl or optionally benzofused 4- to 7-membered heterocycloalkyl is substituted with hydroxyl, as permitted by valence, and any N in the 4- to 7-membered heterocycloalkyl or optionally benzofused 4- to 7-membered heterocycloalkyl is substituted with hydrogen, -NH, C1-C7 aminocarbonyl, -SO2C1-C4 alkyl, -SO2C1-C4 haloalkyl, -C(O)-NH, C ... and 1-C4 alkyl, wherein the alkyl is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, acetylenyl, C1-C4 alkoxy, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 haloalkyl, C3-C6 cycloalkyl, 5-6 membered heteroaryl, and phenyl, wherein the phenyl is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4 alkyl, cyano, and hydroxyl, and wherein any S in the 4-7 membered heterocycloalkyl or optionally benzo-fused 4-7 membered heterocycloalkyl is selected from 1 or 2 of and optionally substituted with 1 to 5 substituents independently selected from the group consisting of: (iii) C3-C6 cycloalkyl [wherein the cycloalkyl is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, oxo, carboxy, C1-C4 alkoxy, C1-C4 alkyl (wherein the alkyl is optionally substituted with 1 to 3 groups selected from the group consisting of halogen and cyano), C1-C4 haloalkyl, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, -C(O)NH-C1-C6 haloalkyl, C2-C6 alkenyl (wherein the alkenyl is optionally substituted with 1 to 3 halogens), and C2-C6 alkynyl]; (iv) A 6-membered aryl or a 5-10-membered heteroaryl [wherein the heteroaryl has 1, 2 or 3 heteroatoms selected from the group consisting of O, S and N, and wherein the carbons of the 6-membered aryl and the 5-10-membered heteroaryl are optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl and -C(O)NH-C1-C6 alkyl], C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl and -C(O)NH-C1-C6 alkyl], 1, 2, or 3 substituents independently selected from the group consisting of cyano, -NH2, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, and -C(O)NH-C3-C6 cycloalkyl, where any N of said heteroaryl may be substituted, as permitted by valence, with a substituent selected from the group consisting of hydrogen and C1-C4 alkyl (wherein said alkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, acetylenyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 alkyl); (v) 4-7 membered heterocycloalkyl, wherein the heterocycloalkyl has 1 or 2 heteroatoms selected from the group of O, S, and N, and wherein the heterocycloalkyl is optionally benzo-fused, and wherein the carbons of the 4-7 membered heterocycloalkyl or the optionally benzo-fused 4-7 membered heterocycloalkyl are selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, C1-C4 alkoxy, C1-C4 alkyl, wherein the alkyl is selected from the group consisting of halogen, cyano, hydroxyl, acetylenyl, oxo, C1-C4 alkoxy, C3 and wherein the 4- to 7-membered heterocycloalkyl is optionally substituted by 1 to 4 substituents independently selected from the group consisting of: -C6 cycloalkyl, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, and -C(O)NH-C1-C6 haloalkyl; Any N in the optionally benzofused 4- to 7-membered heterocycloalkyl, as permitted by valence, may be selected from hydrogen, -NH, C1-C7 aminocarbonyl, -SO2C1-C4 alkyl, -SO2C1-C4 haloalkyl, -C(O)-NH, C1-C4 alkyl (wherein the alkyl is halogen, cyano, hydroxyl, acetylenyl, oxo, C1-C4 alkoxy, C3-C6 cycloalkyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 aryl, - and phenyl, wherein the phenyl is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4 alkyl, cyano, and hydroxyl, whereinany S in said 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with 1 or 2 oxygen atoms; and (vi) -NR 12 R 13 ; Where: R 12 is selected from the group consisting of hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 alkylcycloalkyl, C1-C7 alkylcarbonyl, C1-C7 aminocarbonyl, and C2-C5 alkoxycarbonyl; R 13is hydrogen, C1-C6 alkyl (wherein the alkyl is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl and -SO2C1-C4 alkyl), C3-C6 cycloalkyl, -C(O)-C1-C6 alkyl (wherein the alkyl is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl and -SO2C1-C4 alkyl); hydroxyl, oxo, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, and -SO2C1-C4 alkyl), 4- to 7-membered heterocycloalkyl [wherein the heterocycloalkyl has 1 or 2 heteroatoms selected from the group consisting of O, S, and N, and wherein the heterocycloalkyl is phenyl, ... and wherein the carbon of the 4-7 membered heterocycloalkyl or the optionally benzo-fused 4-7 membered heterocycloalkyl is selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, C1-C4 alkyl (wherein the alkyl is halogen, cyano, hydroxyl, acetylenyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH- and C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, and -C(O)NH-C1-C6 haloalkyl, and wherein any N in the 4-7 membered heterocycloalkyl or the optionally benzofused 4-7 membered heterocycloalkyl is, as far as valence permits, hydrogen, C1-C4 alkyl (wherein the alkyl is halogen, cyano, hydroxyl, acetylenyl,and phenyl, which may be substituted with 1 to 5 substituents independently selected from the group consisting of halogen, C1-C4 alkyl, cyano, and hydroxyl. wherein any S in said 4-7 membered heterocycloalkyl or optionally benzofused 4-7 membered heterocycloalkyl may be substituted with 1 or 2 oxygen atoms] and 5-10 membered heteroaryl [wherein said heteroaryl has 1 or 2 heteroatoms selected from the group consisting of O, S and N, and wherein the carbon of said 5-10 membered heteroaryl is selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C4 a, alkyl (wherein the alkyl is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 alkyl), C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -N and optionally substituted with one, two, or three substituents independently selected from the group consisting of H2, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 alkyl, where any N of the heteroaryl is, as valence permits, hydrogen, C1-C4 alkyl (wherein the alkyl is halogen, cyano, hydroxyl, acetylenyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2,-SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 alkyl; and C3-C6 cycloalkyl; Or, R 11and W together with the nitrogen to which they are attached form a 4-7 membered ring which may contain 1-2 heteroatoms selected from the group consisting of N, S and O, wherein the ring carbons are selected from cyano, hydroxyl, oxo, halogen, C1-C2 alkoxy, N,N-di-C1-C4-alkylaminocarboxyl, N-C1-C4-alkylaminocarboxyl, C1-C7 aminocarboxyl, C1-C4 alkyl (wherein the alkyl is halogen, cyano, hydroxyl, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C C(O)NH-C3-C6 cycloalkyl (wherein the cycloalkyl is optionally substituted with 1 to 3 substituents selected from the group consisting of halogen, cyano, hydroxyl, and C1-C4 alkoxy), -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, -C(O)NH-C1-C6 haloalkyl, 5-6 membered heteroaryl, and phenyl (wherein the phenyl is optionally substituted with halogen, C1-C4 alkyl, cyano, hydroxyl, C1-C2 alkoxy, N,N-di-C1-C4-alkylaminocarboxyl, N-C1-C4-alkylaminocarboxyl, and C1-C7 aminocarboxyl, any N in the 4- to 7-membered ring may be substituted with 1 to 4 substituents independently selected from the group consisting of hydrogen, C1-C4 alkyl (wherein the alkyl is halogen, cyano, hydroxyl, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, and -C(O)NH-C3-C6 cycloalkyl. groups), C3-C6 cycloalkyl (wherein the cycloalkyl is optionally substituted with 1-3 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C1-C4 alkoxy, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 alkyl), 5-6 membered heteroaryl, and phenyl (wherein the phenyl is optionally substituted with 1-3 substituents independently selected from the group consisting of halogen, C1-C4 alkyl, cyano, and hydroxyl), and any S in the 4-7 membered ring is optionally substituted with 1 or 2 oxygen atoms; Y is C1-C6 alkyl, wherein the alkyl is halogen, cyano, hydroxyl, oxo, C3-C6 cycloalkyl, C1-C4 alkoxy, acetylenyl, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -SON2NH(C1-C4 alkyl), -SON2N(C1-C4 alkyl)2, -SON2NH(C1-C4 haloalkyl), -C(O)NH-C3-C6 cycloalkyl, wherein which is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, hydroxyl, cyano and C1-C4 alkyl (wherein the alkyl is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C1-C4 alkoxy and -NH2), -C(O)NH-C1-C6 alkyl, -C(O)NH-C1-C6 cyanoalkyl (wherein the alkyl is optionally substituted with 1 to 3 halogens), -C(O)NH-C1-C6 haloalkyl, phenyl (wherein the phenyl is halogen, cyano, nitro, hydroxyl, C1-C4 alkyl (wherein the alkyl may be substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2 and -C(O)NH-C3-C6 cycloalkyl) and C3-C6 cycloalkyl (wherein the cycloalkyl is halogen, cyano, hydroxyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, C2-C6 alkenyl and C2-C6 alkynyl), 5-10 membered heteroaryl [wherein the heteroaryl is selected from the group consisting of O,and having 1 or 2 heteroatoms selected from the group of S and N, wherein the carbons of the 5-10 membered heteroaryl are selected from halogen, cyano, nitro, hydroxyl, C1-C4 alkyl (wherein the alkyl is selected from halogen, cyano, hydroxyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH- C1-C6 alkyl), C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 alkyl, where any N of the heteroaryl is optionally substituted with hydrogen, C1-C4 alkyl, or C1-C4 alkyl, as valence permits. (wherein the alkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, acetylenyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 alkyl) and a substituent selected from the group consisting of C3-C6 cycloalkyl. and 4-7 membered heterocycloalkyl, wherein the heterocycloalkyl has 1 or 2 heteroatoms selected from the group of O, S, and N, and wherein the heterocycloalkyl is optionally benzofused, wherein the carbons of the 4-7 membered heterocycloalkyl or the optionally benzofused 4-7 membered heterocycloalkyl are selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, C1-C4 alkyl, wherein the alkyl is selected from the group consisting of halogen, cyano, hydroxyl, acetylenyl, oxo, C1-C4 alkoxy, -NH2,and C3-C6 cycloalkyl, wherein any N of the 4-7 membered heterocycloalkyl or the optionally benzofused 4-7 membered heterocycloalkyl is, as valence permits, hydrogen, C1-C4 alkyl (wherein the alkyl is halogen, cyano, hydroxyl, acetylenyl, C1-C4 alkoxy, or the like). , -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl and -C(O)NH-C1-C6 alkyl), C3-C6 cycloalkyl and 5-6 membered heteroaryl, wherein any S in the 4-7 membered heterocycloalkyl or the optionally benzo-fused 4-7 membered heterocycloalkyl may be substituted by 1 or 2 oxygen atoms, The present invention provides a compound represented by the formula:

[0008] In one embodiment, the present invention further provides a composition comprising a compound of formula (I) or a salt thereof and at least one acceptable excipient, wherein the composition further comprises at least one additional active compound.

[0009] In one embodiment, the present invention further provides a method of treating pests, comprising administering to a subject in need thereof an effective amount of a compound represented by formula (I) or a salt thereof, wherein the method may further comprise an effective amount of at least one additional active compound.

[0010] In one embodiment, the present invention further provides a method for controlling pests, comprising administering to a subject in need thereof an effective amount of a compound represented by formula (I) or a salt thereof, wherein the method may further comprise an effective amount of at least one additional active compound.

[0011] In one embodiment, the present invention further provides a method of treating or controlling a pest, the method comprising contacting the environment of a subject with an effective amount of a compound of formula (I) or a salt thereof, the method optionally further comprising an effective amount of at least one additional active compound.

[0012] Thus, the present invention provides the use of a compound of the present invention as a medicament, including the use for the manufacture of a medicament. In one embodiment, the present invention provides the manufacture of a medicament comprising a compound of formula (I) or a salt thereof for treating a parasite. In one embodiment, the present invention provides the manufacture of a medicament comprising a compound of formula (I) or a salt thereof for controlling a pest.

[0013] The present invention further provides processes for preparing the compounds of the present invention and intermediates thereto. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] The term "C1-C2 alkyl" refers to an alkyl chain having 1 to 2 carbon atoms and includes methyl and ethyl.

[0015] The term "C1-C4 alkyl" refers to a straight or branched alkyl chain having from 1 to 4 carbon atoms and includes methyl, ethyl, propyl, isopropyl, butyl and the like.

[0016] Similarly, the term "C1-C6 alkyl" refers to a straight or branched alkyl chain having from 1 to 6 carbon atoms and includes methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl and the like.

[0017] The terms "C1-C4 haloalkyl" and "C1-C4 halogenoalkyl" refer to straight or branched alkyl chains having 1 to 4 carbon atoms and 1 to 5 halogens, and include fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 1,2,2-trifluoroethyl, and 3,3,3-trifluoropropyl, and the like.

[0018] The terms "C1-C6 haloalkyl" and "C1-C6 halogenoalkyl" refer to straight or branched alkyl chains having 1 to 6 carbon atoms and 1 to 5 halogens, and include fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 1,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, and 4,4,4-trifluorobutyl.

[0019] The term "C2-C6 alkenyl" refers to a straight or branched alkenyl chain having from 2 to 4 carbon atoms and one carbon-carbon double bond, and includes ethylene, propylene, iso-propylene, butylene, iso-butylene, sec-butylene, and the like.

[0020] The term "C2-C6 alkynyl" refers to a straight or branched alkynyl chain having from 2 to 4 carbon atoms and one carbon-carbon triple bond, and includes acetylene and propargyl.

[0021] The term "C1-C2 alkoxy" refers to a C1-C2 alkyl group bonded through an oxygen atom and includes methoxy and ethoxy.

[0022] The term "C1-C4 alkoxy" refers to a C1-C4 alkyl group attached through an oxygen atom and includes methoxy, ethoxy, propoxy, isopropoxy, butoxy and the like.

[0023] The term "C1-C6 alkoxy" refers to a C1-C6 alkyl group attached through an oxygen atom and includes methoxy, ethoxy, propoxy, isopropoxy, butoxy and the like.

[0024] The term "C3-C6 cycloalkyl" refers to an alkyl ring of three to six carbon atoms and includes cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. It is understood that the cycloalkyl rings can be fused, bridged, or spiro-fused.

[0025] The term "C4-C7 alkylcycloalkyl" refers to a C1-C4 alkyl substituted with a C3-C6 cycloalkyl such that the total number of carbons is 4 to 7, and includes cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylethyl, and the like.

[0026] The terms "halo", "halogen" and "halo" refer to a chloro, fluoro, bromo, or iodo atom.

[0027] The terms "4-7 membered heterocycloalkyl, wherein the heterocycloalkyl has 1 or 2 heteroatoms selected from the group O, S, N, and wherein the heterocycloalkyl is optionally benzofused" and "4-7 membered heterocycloalkyl, wherein the heterocycloalkyl has 1 or 2 heteroatoms selected from the group O, S, B, N, and wherein the heterocycloalkyl is optionally benzofused" refer to a 4-7 membered saturated or partially (but not completely) unsaturated ring having 1 or 2 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, or having 1 or 2 heteroatoms selected from the group consisting of nitrogen, oxygen, boron, and sulfur, which may contain a carbonyl to form a lactam or lactone. If sulfur is included, the sulfur may be -S-, -SO-, or -SO2-. It is understood that the heterocyclic ring can be either monocyclic or bicyclic, and any bicyclic ring can be fused, bridged, or spiro-fused. The 4-7 member definition excludes rings that are optionally benzo-fused. Also, as will be fully understood by those skilled in the art, the definition of a 4-7 membered heterocycloalkyl ring that is saturated or partially (but not completely) unsaturated applies to the heterocycloalkyl ring and not to any benzo-fused ring that is fully unsaturated in nature. It is further understood that groups can be attached as substituents through the ring heteroatoms (where valences permit), carbon atoms of the heterocycloalkyl, or carbon atoms of any benzo-fused ring. It is also understood that when an optionally benzo-fused 4-7 membered heterocycloalkyl is optionally substituted on carbon, the substituents can be present on the carbon atoms of the heterocycle and / or the benzo-fused ring.For example, and without limitation, this term includes azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, oxetanyl, thioxetanyl, dioxolanyl, tetrahydropyranyl, tetrahydrothiopyranyl, tetrahydrofuryl, hexahydropyrimidinyl, tetrahydropyrimidinyl, 2,6-diazaspiro[3.3]heptanyl, isoxazolidine, dihydroimidazolyl, indolyl, isoindolyl, and the like.

[0028] The term "5-6 membered heteroaryl" refers to a 6 membered fully unsaturated monocyclic ring having 1-5 carbon atoms and one or more (typically 1-4) heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur. For example, but not limited to, the term includes pyrrolyl, furyl, thienyl, imidazolyl, oxazoyl, isoxazoyl, thiazolyl, triazolyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridyl and pyrimidyl. It is understood that the 6 membered heteroaryl can be attached as a substituent via a ring carbon atom or a ring nitrogen atom, if such a bonding mode is available.

[0029] R 11 When and W are taken together with the nitrogen to which they are attached, the term "4- to 7-membered ring optionally containing 1-2 heteroatoms selected from the group consisting of N, S, and O" is R 11 and W represents a fully saturated or partially unsaturated (but not completely) ring having 4 to 7 ring members including the nitrogen to which it is attached, and includes azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, oxetanyl, dioxolanyl, tetrahydropyranyl, tetrahydrothiopyranyl, tetrahydrofuryl, hexahydropyrimidinyl, tetrahydropyrimidinyl, and dihydroimidazolyl.

[0030] The term "5-10 membered heteroaryl, wherein the heteroaryl has 1 or 2 heteroatoms selected from the group O, S, and N" refers to a 5-10 membered monocyclic or polycyclic fully unsaturated ring or ring system having 1 to 9 carbon atoms and 1 or 2 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur. For example, but not limited to, this term includes furyl, thienyl, pyrrolyl, imidazolyl, isothiazolyl, isoxazolyl, oxadiazolyl, oxazolyl, thiazolyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidyl, azepinyl, diazepinyl, benzofuryl, benzothienyl, indolyl, isoindolyl, benzimidazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, benzopyrazinyl, benzopyrazolyl, quinazolyl, thienopyridyl, quinolyl, isoquinolyl, and benzothiazolyl. It is understood that a 5-10 membered heteroaryl (wherein the heteroaryl has 1 or 2 heteroatoms selected from the group of O, S, and N) can be attached as a substituent via a ring carbon atom or a ring nitrogen atom, if such a bonding mode is available.

[0031] The term "oxo" refers to an oxygen atom doubly bonded to the carbon to which it is attached to form the carbonyl of an amide, ketone, or aldehyde. For example, the pryidone radical is contemplated as an oxo-substituted 6-membered heteroaryl.

[0032] The term "carboxyl" refers to the following group: [ka] This shows that.

[0033] The term "N,N-di-C1-C4-alkylaminocarboxyl" refers to the group immediately below. [ka] wherein the hydrogen on the nitrogen is replaced with two independently selected C1-C4 alkyl groups. This shows that.

[0034] Similarly, the term "N-C1-C4-alkylaminocarboxyl" refers to the group immediately below. [ka] (wherein one of the hydrogens on the nitrogen is replaced with a C1-C4 alkyl group) This shows that.

[0035] The term "C2-C5 alkoxycarbonyl" refers to the following group: [ka] wherein R is C1-C4 alkyl. This shows that.

[0036] The term "C2-C7 alkylcarbonyl" refers to the following group: [ka] wherein R is C1-C6 alkyl. This shows that.

[0037] Similarly, the term "C2-C7 haloalkylcarbonyl" refers to the group immediately above, where R is a C1-C6 haloalkyl.

[0038] The term "C1-C7 aminocarbonyl" refers to the following group: [ka] wherein R is hydrogen or C1-C4 alkyl. This shows that.

[0039] The term "nil" as used herein with respect to groups, substituents, or moieties, etc., indicates that the group, substituent, or moiety is not present. When a group, substituent, or moiety is normally bonded to two or more other groups, substituents, or moieties, the other groups, substituents, or moieties are bonded together in place of the absent group, substituent, or moiety. For example, in a compound having the structure ABC, if B is absent, A is directly bonded to C, and the compound is AC. As another example, in a compound having the structure ABC, if C is absent, the compound is AB.

[0040] The terms "salt" and "salts" refer to veterinarily or pharma- ceutically acceptable salts of organic or inorganic acids and bases. Such salts are well known in the art and include those described in the Journal of Pharmaceutical Science, 66, 2-19 (1977). One example is the hydrochloride salt.

[0041] The term "substituted", including the case where it is used in "optionally substituted", refers to a hydrogen radical that is replaced with a non-hydrogen radical (substituent) at one or more hydrogen radicals of a group. It is understood that the substituents may be the same or different at each substitution position. The combination of groups and substituents envisioned by the present invention is one that is stable or chemically feasible. For the compounds described herein, the groups and substituents can be selected according to the allowed valences of the atoms and the substituents, such that the selection and substitution result in a stable compound (e.g., a stable compound that does not spontaneously undergo transformation (e.g., transformation by rearrangement, cyclization, elimination, etc.)).

[0042] The term "stable" refers to compounds that do not change substantially when subjected to conditions that enable their production. In a non-limiting example, a stable compound or chemically feasible compound is one that does not change substantially when kept at a temperature of 40° C. or less for about one week in the absence of moisture or other chemically reactive conditions.

[0043] It is understood that when terms defined herein refer to a number of carbon atoms, the number referred to refers to the group referred to and does not include carbons that may be present within optional substituents on that group or carbons that may be present as part of a fused ring, including a benzo-fused ring.

[0044] Those skilled in the art will recognize that some of the compounds of the present invention exist as isomers. All stereoisomers (including geometric isomers, enantiomers and diastereomers) of the compounds of the present invention in any ratio are intended to be within the scope of the present invention.

[0045] As used herein, the term "(RS)" in chemical nomenclature indicates a racemic mixture at the indicated stereocenter.

[0046] As used herein, the terms "(R or S)" or "(S or R)" in chemical nomenclature refer to one of two possible configurations at the indicated stereocenter.

[0047] One of ordinary skill in the art will further recognize that some of the compounds of the present invention exist as tautomers, and all tautomeric forms of the compounds of the present invention are intended to be within the scope of the present invention.

[0048] The compounds of the present invention also include all isotopic variants in which at least one atom having a major atomic mass is replaced by an atom having the same atomic number but an atomic mass different from the major atomic mass. 23H) may provide enhanced metabolic stability. Additionally, certain isotopic variations of the compounds of the invention may be conjugated to radioactive isotopes (e.g., tritium, 3 H, or 14 C), which may be useful in drug and / or substrate tissue distribution studies. Positron emitting isotopes (e.g., 11 C. 18 F, 15 O and 13 N) substitution may be useful in positron emission tomography (PET) studies.

[0049] The terms "compounds of the invention" and "a compound of the invention" and "compounds of the present invention" and the like include embodiments of Formula (I) and the other more specific embodiments encompassed by Formula (I) described herein and the exemplary compounds described herein and salts of each of these embodiments.

[0050] Compounds of formula (I) in various embodiments, such as: Formula (I) [ka] TIFF2024523313000012.tif219126TIFF2024523313000013.tif128129A4, A5, A6, A7, A9, A 10 , A 11 , A 12 , A 14 and / or A 15 With respect to the above, it is understood that the R6 substituent, if present, replaces the hydrogen of the CH.

[0051] It is further understood that with respect to compounds of formula (Ig), the X group, if present, is attached by replacing the hydrogen of a -CH- group or a -CH- group, or R of a -NR- group, at W3, W4, W5 or W6.

[0052] Further embodiments of the compounds of the invention are described below.

[0053] (1) One embodiment relates to a compound represented by formula (I) or a salt thereof.

[0054] (a) One embodiment relates to a compound represented by formula (Ia) or a salt thereof.

[0055] (b) One embodiment relates to a compound represented by formula (Ib) or a salt thereof.

[0056] (c) One embodiment relates to a compound represented by formula (Ic) or a salt thereof.

[0057] (d) One embodiment relates to a compound represented by formula (Id) or a salt thereof.

[0058] (e) One embodiment relates to a compound represented by formula (Ie) or a salt thereof.

[0059] (f) One embodiment relates to a compound represented by formula (If) or a salt thereof.

[0060] (g) One embodiment relates to a compound represented by formula (Ig) or a salt thereof.

[0061] (h) One embodiment relates to embodiments (1), (a), (b), (c), (d), (e), (f), and (g), or salts thereof, wherein R1 is hydrogen, R2 is trifluoromethyl, R3 is hydrogen, R4 is trifluoromethyl, and R5 is halogen.

[0062] (i) One embodiment relates to embodiments (1), (a), (b), (c), (d), (e), (f) and (g), or salts thereof, wherein R1 is hydrogen, R2 is trifluoromethyl, R3 is hydrogen, R4 is halogen, and R5 is halogen.

[0063] (j) One embodiment relates to embodiments (1), (a), (b), (c), (d), (e), (f), and (g), or salts thereof, wherein R1 is hydrogen, R2 is trifluoromethyl, R3 is hydrogen, R4 is chloro, and R5 is halogen.

[0064] (k) One embodiment relates to embodiments (1), (a), (b), (c), (d), (e), (f) and (g), or salts thereof, wherein R1 is hydrogen, R2 is trifluoromethyl, R3 is hydrogen, R4 is halogen and R5 is chloro.

[0065] (l) One embodiment relates to embodiments (1), (a), (b), (c), (d), (e), (f) and (g), or salts thereof, wherein R1 is hydrogen, R2 is trifluoromethyl, R3 is hydrogen, R4 is halogen and R5 is fluoro.

[0066] (m) One embodiment relates to embodiments (1), (a), (b), (c), (d), (e), (f) and (g), or salts thereof, wherein R1 is hydrogen, R2 is trifluoromethyl, R3 is hydrogen, R4 is chloro and R5 is fluoro.

[0067] (n) One embodiment relates to embodiments (1), (a), (b), (c), (d), (e), (f), (g), (h), (i), (j), (k), (l) and (m) or salts thereof, wherein A2 is O.

[0068] (o) One embodiment relates to embodiments (1), (a), (b), (c), (d), (e), (f), (g), (h), (i), (j), (k), (l), (m), and (n), or salts thereof, wherein A1 is CF3.

[0069] (p) One embodiment relates to embodiments (1), (a), (b), (c), (d), (e), (f), (g), (h), (i), (j), (k), (l), (m) and (n) or salts thereof, wherein A1 is CHF2.

[0070] (q) One embodiment relates to embodiments (1), (a), (h), (i), (j), (k), (l), (m), (n), (o) and (p) or salts thereof, wherein A3 is S.

[0071] (r) One embodiment relates to embodiment (q) or a salt thereof, wherein p is 1 and R5 is C1-C6 alkyl.

[0072] (s) One embodiment relates to embodiment (r) or a salt thereof, wherein R6 is methyl.

[0073] (t) One embodiment relates to embodiments (1), (b), (h), (i), (j), (k), (l), (m), (n), (o) and (p) or salts thereof, wherein A4, A5 and A6 are CH.

[0074] (u) One embodiment relates to embodiment (t) or a salt thereof, wherein p is 1 and R6 is C1-C6 alkyl.

[0075] (v) One embodiment relates to embodiment (u) or a salt thereof, wherein R6 is methyl.

[0076] (w) One embodiment is A7, A8, A9, A 10 , A 11 and A 12 is CH, or a salt thereof.

[0077] (x) In one embodiment, 13 , A 14 and A 15is CH, or a salt thereof.

[0078] (y) One embodiment relates to embodiment (x) or a salt thereof, wherein W1 is -CH2- and W2 is O.

[0079] (z) In one embodiment, X is [ka] where R 11 is hydrogen; or a salt thereof.

[0080] (aa) In one embodiment, W is C1-C6 alkyl, where the alkyl is: halogen; Cyano; Hydroxyl; oxo; C1-C4 alkoxy; C3-C6 cycloalkyl, wherein the cycloalkyl is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen and cyano; Acetylenyl; -NH2; C1-C7 aminocarbonyl; -NH(C1-C4 alkyl); -N(C1-C4 alkyl)2; -SC1-C4 alkyl; -S(O)C1-C4 alkyl; -SO2C1-C4 alkyl; -C(O)NH-C3-C6 cycloalkyl, halogen, Hydroxyl, Cyano and C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, C1-C4 alkoxy, C3-C6 cycloalkyl, and -NH2 (optionally substituted with 1 to 5 substituents independently selected from the group consisting of): -C(O)NH-C1-C6 alkyl, halogen, Cyano, Hydroxyl, C1-C4 alkoxy, C3-C6 cycloalkyl, and -NH2, -C(O)NH-C1-C6 cyanoalkyl, optionally substituted with 1 to 3 halogens; -C(O)NH-C1-C6 haloalkyl; -C(O)-4 to 7 membered heterocycloalkyl, which is attached through a nitrogen and may have one or two other heteroatoms selected from the group of O, S, N, where the carbon of the 4 to 7 membered heterocycloalkyl is halogen, Cyano, Nitro, Hydroxyl, Oxo, -NH2, C1-C7 aminocarbonyl, C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, Acetylenyl, Oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 alkyl and C3-C6 Cycloalkyl and optionally substituted with 1 to 4 substituents independently selected from the group consisting of and any other N of the 4- to 7-membered heterocycloalkyl, as permitted by valence, hydrogen, -NH2, C1-C7 aminocarbonyl, -SO2C1-C4 alkyl, -SO2C1-C4 haloalkyl, C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, Acetylenyl, C1-C4 alkoxy, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, -C(O)NH-C1-C6 haloalkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of substituted with a substituent selected from the group consisting of: 5-10 membered heteroaryl, wherein the heteroaryl has 1 or 2 heteroatoms selected from the group of O, S and N, wherein the carbons of the 5-10 membered heteroaryl are halogen, Cyano, Nitro, Hydroxyl, C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, Oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, and -C(O)NH-C1-C6 haloalkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, and -C(O)NH-C3-C6 cycloalkyl and optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of: and any N in heteroaryl, valence permitting, hydrogen, C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, Acetylenyl, Oxo, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 alkyl and C3-C6 Cycloalkyl may be substituted with a substituent selected from the group consisting of and, any S in said heteroaryl is substituted with one or two oxygen atoms; Phenyl, wherein the phenyl is halogen, C1-C4 alkyl, Cyano or hydroxyl; C3-C6 cycloalkyl, wherein the cycloalkyl is halogen, Cyano, Hydroxyl, Oxo, C1-C4 alkoxy, C1-C4 alkyl (wherein the alkyl is optionally substituted with 1 to 3 groups selected from the group consisting of halogen and cyano) C1-C4 haloalkyl, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, -C(O)NH-C1-C6 haloalkyl, C2-C6 alkenyl, and C2-C6 Alkynyl and optionally substituted with 1 to 5 substituents independently selected from the group consisting of: And, 4-7 membered heterocycloalkyl, wherein said heterocycloalkyl has 1 or 2 heteroatoms selected from the group of O, S, B, N, wherein said heterocycloalkyl is optionally benzo-fused, and wherein a carbon of said 4-7 membered heterocycloalkyl or optionally benzo-fused 4-7 membered heterocycloalkyl is halogen, Cyano, Nitro, Hydroxyl, Oxo, C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, Acetylenyl, Oxo, C1-C4 alkoxy, C3-C6 cycloalkyl, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, and -C(O)NH-C1-C6 haloalkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of and optionally substituted with 1 to 4 substituents independently selected from the group consisting of and any B in said 4- to 7-membered heterocycloalkyl or optionally benzofused 4- to 7-membered heterocycloalkyl is substituted with hydroxyl, where valences permit; and any N in said 4- to 7-membered heterocycloalkyl or optionally benzofused 4- to 7-membered heterocycloalkyl, as permitted by valence, is hydrogen, -NH2, C1-C7 aminocarbonyl, -SO2C1-C4 alkyl, -SO2C1-C4 haloalkyl, -C(O)-NH2, C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, Acetylenyl, C1-C4 alkoxy, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 haloalkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of C3-C6 cycloalkyl, 5-6 membered heteroaryl, and Phenyl, wherein the phenyl is halogen, C1-C4 alkyl, Cyano and Hydroxyl may be substituted with 1 to 3 substituents independently selected from the group consisting of and is substituted with a substituent selected from the group consisting of and any S in said 4- to 7-membered heterocycloalkyl or optionally benzofused 4- to 7-membered heterocycloalkyl is substituted with 1 or 2 oxygen atoms; or a salt thereof, wherein the compound is optionally substituted with 1 to 5 substituents independently selected from the group consisting of:

[0081] (ab) In one embodiment, W is C1-C6 alkyl, where the alkyl is: -C(O)NH-C1-C6 alkyl, halogen, Cyano, Hydroxyl, C1-C4 alkoxy, C3-C6 cycloalkyl, and -NH2 and optionally substituted with 1 to 5 substituents independently selected from the group consisting of: -C(O)NH-C1-C6 cyanoalkyl, optionally substituted with 1 to 3 halogens; -C(O)NH-C1-C6 haloalkyl; and -C(O)-4 to 7 membered heterocycloalkyl, wherein the heterocycloalkyl is attached through a nitrogen and optionally has one or two other heteroatoms selected from the group of O, S, N, and wherein the carbon of the 4 to 7 membered heterocycloalkyl is halogen, Cyano, Nitro, Hydroxyl, Oxo, -NH2, C1-C7 aminocarbonyl, C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, Acetylenyl, Oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 alkyl and C3-C6 Cycloalkyl and optionally substituted with 1 to 4 substituents independently selected from the group consisting of and any other N in the 4- to 7-membered heterocycloalkyl, as valence permits, hydrogen, -NH2, C1-C7 aminocarbonyl, -SO2C1-C4 alkyl, -SO2C1-C4 haloalkyl, C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, Acetylenyl, C1-C4 alkoxy, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, -C(O)NH-C1-C6 haloalkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of

[0043] The present invention relates to embodiment (aa), or a salt thereof, wherein the compound is substituted with a substituent selected from the group consisting of:

[0082] (ac) In one embodiment, W is [ka] or a salt thereof.

[0083] (ad) One embodiment relates to embodiment (z) or a salt thereof, wherein W is C1-C6 alkyl, where the alkyl is optionally substituted with -C(O)NH-C3-C6 cycloalkyl, where the alkyl is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, hydroxyl, cyano, and C1-C4 alkyl, where the alkyl is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C1-C4 alkoxy, and -NH2.

[0084] (ae) In one embodiment, W is C1-C6 alkyl, where the alkyl is -C(O)NH-C1-C6 alkyl, which is halogen, Cyano, Hydroxyl, C1-C4 alkoxy, C3-C6 cycloalkyl, and -NH2, optionally substituted with 1 to 5 substituents independently selected from the group consisting of or a salt thereof.

[0085] (ae1) In one embodiment, W is [ka] or a salt thereof.

[0086] (ae2) In one embodiment, W is [ka] or a salt thereof.

[0087] (af) One embodiment is where W is C1-C6 alkyl, where the alkyl is a 5-10 membered heteroaryl, where the heteroaryl has 1 or 2 heteroatoms selected from the group of O, S, B, and N, and where the carbons of the 5-10 membered heteroaryl are selected from halogen, cyano, nitro, hydroxyl, C1-C4 alkyl, where the alkyl is halogen, cyano, hydroxyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C and -C(O)NH-C1-C6 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 alkyl), C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, and -C(O)NH and any B of said heteroaryl is substituted with hydroxyl, and any N of said heteroaryl is, where valence permits, hydrogen, C1-C4 alkyl (wherein said alkyl is halogen, cyano, hydroxyl, acetylenyl, oxo, C3-C6 cycloalkyl, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), and any S of said heteroaryl is substituted by 1 or 2 oxygen atoms).

[0088] (af1) One embodiment is where W is C1-C6 alkyl, where the alkyl is selected from the group consisting of pyridine, where the pyridine is halogen, cyano, nitro, hydroxyl, C1-C4 alkyl, where the alkyl is halogen, cyano, hydroxyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl), -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH and optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2 and -C(O)NH-C3-C6 cycloalkyl, or a salt thereof.

[0089] (af2) One embodiment is where W is C1-C6 alkyl, where the alkyl is thiazole, where the thiazole is halogen, cyano, nitro, hydroxyl, C1-C4 alkyl, where the alkyl is halogen, cyano, hydroxyl, oxo, C1-C4 alkoxy, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl), -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)N and H-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, and optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, and -C(O)NH-C3-C6 cycloalkyl, or a salt thereof.

[0090] (ag) In one embodiment, W is a 4-7 membered heterocycloalkyl having 1 or 2 heteroatoms selected from the group O, S, N, wherein the heterocycloalkyl is optionally benzo-fused, and wherein the carbons of the 4-7 membered heterocycloalkyl or the optionally benzo-fused 4-7 membered heterocycloalkyl are halogen, Cyano, Nitro, Hydroxyl, Oxo, C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, Acetylenyl, Oxo, C1-C4 alkoxy, C3-C6 cycloalkyl, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, and -C(O)NH-C1-C6 haloalkyl and optionally substituted with 1 to 4 substituents independently selected from the group consisting of: and any N in said 4- to 7-membered heterocycloalkyl or optionally benzofused 4- to 7-membered heterocycloalkyl, as permitted by valence, is hydrogen, -NH2, C1-C7 aminocarbonyl, -SO2C1-C4 alkyl, -SO2C1-C4 haloalkyl, -C(O)-NH2, C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, Acetylenyl, C1-C4 alkoxy, C3-C6 cycloalkyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 haloalkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of C3-C6 cycloalkyl, 5-6 membered heteroaryl, and Phenyl, wherein the phenyl is halogen, C1-C4 alkyl, Cyano and Hydroxyl and each of the substituted or unsubstituted groups is substituted with one or more substituents selected from the group consisting of: And, any S in the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl is substituted with 1 or 2 oxygen atoms, or a salt thereof.

[0091] (ag1) In one embodiment, W is a 4-7 membered heterocycloalkyl having 1 or 2 heteroatoms selected from the group O, S, N, where the heterocycloalkyl is selected from the group consisting of pyrrolyl, azetidinyl, 2-oxoazetidinyl, isoxazolidinyl, 2,6-diazaspiro[3.3]heptanyl, and 1,6-diazaspiro[3.3]heptanyl, where the carbons of the 4-7 membered heterocycloalkyl are halogen, Cyano, Nitro, Hydroxyl, Oxo, C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, Acetylenyl, Oxo, C1-C4 alkoxy, C3-C6 cycloalkyl, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, and -C(O)NH-C1-C6 haloalkyl and optionally substituted with 1 to 4 substituents independently selected from the group consisting of: and any N in the 4-7 membered heterocycloalkyl, as far as valence allows, hydrogen, -SO2C1-C4 alkyl, -SO2C1-C4 haloalkyl, -C(O)-NH2, C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, Acetylenyl, C1-C4 alkoxy, C3-C6 cycloalkyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, and -C(O)NH-C1-C6 haloalkyl and C3-C6 Cycloalkyl or a salt thereof, wherein

[0092] (ah) One embodiment relates to embodiments (ag) and (ag1), or salts thereof, wherein the carbons of the 4-7 membered heterocycloalkyl are optionally substituted with one or two substituents independently selected from the group consisting of oxo and C1-C4 alkyl, and any N of the 4-7 membered heterocycloalkyl is substituted, as valences permit, with hydrogen and C1-C4 alkyl, where the alkyl is optionally substituted with one to three halogens, cyano, acetylenyl, or C3-C6 cycloalkyl.

[0093] (ai) One embodiment relates to embodiments (ag), (ag1), and (ah), or salts thereof, wherein a carbon of the 4-7 membered heterocycloalkyl is substituted with one oxo and, where valences permit, any N of the 4-7 membered heterocycloalkyl is substituted with a C1-C4 alkyl substituted with one cyano.

[0094] (aj) One embodiment relates to embodiments (ag), (ag1), and (ah), or salts thereof, wherein a carbon of the 4-7 membered heterocycloalkyl is substituted with one oxo, and any N of the 4-7 membered heterocycloalkyl is substituted with a C1-C4 alkyl substituted with 1-3 halogens, where valences permit.

[0095] (ak) One embodiment relates to embodiments (ag), (ag1), and (ah), or salts thereof, wherein a carbon of the 4-7 membered heterocycloalkyl is substituted with one oxo and any N of the 4-7 membered heterocycloalkyl is substituted, where valences permit, with a C1-C4 alkyl substituted with one C3-C6 cycloalkyl.

[0096] (al) One embodiment relates to embodiments (ag), (ag1), and (ah), or salts thereof, wherein any N of the 4 to 7 membered heterocycloalkyl is substituted with a C1-C4 alkyl substituted with one cyano, valence permitting.

[0097] (am) One embodiment relates to embodiments (ag), (ag1), and (ah), or salts thereof, wherein any N of the 4 to 7 membered heterocycloalkyl is substituted with C1-C4 alkyl substituted with 1 to 3 halogens, where valences permit.

[0098] (an) One embodiment relates to embodiments (ag), (ag1) and (ah), or salts thereof, wherein any N of the 4 to 7 membered heterocycloalkyl is substituted with a C1-C4 alkyl substituted with one C3-C6 cycloalkyl, where valences permit.

[0099] (an1) In one embodiment, W is C3-C6 cycloalkyl, where the cycloalkyl is: halogen, Cyano, Hydroxyl, Oxo, C1-C4 alkoxy, C1-C4 alkyl (wherein the alkyl is optionally substituted with 1 to 3 groups selected from the group consisting of halogen and cyano); C1-C4 haloalkyl, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, -C(O)NH-C1-C6 alkyl, -C(O)NH-C1-C6 haloalkyl, C2-C6 alkenyl (wherein the alkenyl may be substituted with 1 to 3 halogens), and C2-C6 Alkynyl or a salt thereof, wherein the compound is optionally substituted with 1 to 5 substituents independently selected from the group consisting of:

[0100] (ao) In one embodiment, Y is C1-C6 alkyl, where the alkyl is: halogen, Cyano, Hydroxyl, Oxo, C3-C6 cycloalkyl, C1-C4 alkoxy, Acetylenyl, -NH2, C1-C7 aminocarbonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -SC1-C4 alkyl, -S(O)C1-C4 alkyl, -SO2C1-C4 alkyl, -C(O)NH-C3-C6 cycloalkyl, which is halogen, Hydroxyl, Cyano and C1-C4 alkyl, wherein the alkyl is halogen, Cyano, Hydroxyl, C1-C4 alkoxy, and -NH2 (Optionally substituted with 1 to 5 substituents independently selected from the group consisting of: -C(O)NH-C1-C6 alkyl, -C(O)NH-C1-C6 cyanoalkyl (which may be optionally substituted with 1 to 3 halogens); -C(O)NH-C1-C6 haloalkyl or a salt thereof, optionally substituted with 1 to 5 substituents independently selected from the group consisting of:

[0101] (ap) One embodiment relates to embodiment (aq) or a salt thereof, wherein Y is C1-C6 alkyl substituted with one -SO2C1-C4 alkyl.

[0102] (aq) One embodiment relates to embodiment (ao) or (ap), or a salt thereof, wherein Y is C1-C6 alkyl substituted with one -SO2CH3.

[0103] (ar) In one embodiment, W is [ka] The present invention relates to embodiment (z),

[0104] (as) In one embodiment, W is [ka] The present invention relates to embodiment (z),

[0105] (at) In one embodiment, W is [ka] The present invention relates to embodiment (z),

[0106] (au) In one embodiment, W is [ka] The present invention relates to embodiment (z),

[0107] (as) In one embodiment, W is [ka] The present invention relates to embodiment (z),

[0108] (at) In one embodiment, W is [ka] The present invention relates to embodiment (z),

[0109] (au) In one embodiment, W is [ka] The present invention relates to embodiment (z),

[0110] (xa) Another embodiment relates to each of the exemplified compounds or a salt thereof.

[0111] (xb) Another embodiment relates to each stereoisomer of each compound exemplified, depicted or named, or a salt thereof.

[0112] (xc) Another embodiment relates to salts of each of the exemplified compounds.

[0113] The compounds of the present invention can be prepared by a variety of methods, many of which have been previously described in the art, see, for example, WO2005 / 085216, WO2007 / 079162, US2007 / 066617, US20130131017, WO2009 / 002809, WO2009 / 112275, WO2010 / 003923, WO2010 / 070068, WO2012 / 120399, and WO2013 / 079407.

[0114] The present disclosure relates to compounds of formula (I) with extended half-life. Compounds of formula (I) either have a trifluoromethyl group at the meta position or a halogen at the para and / or ortho positions. Thus, compounds of formula (I) include the following features: a trifluoromethyl group at one or both meta positions; a halogen at the ortho position; a halogen at each of the ortho and para positions; or a halogen at each of the ortho positions and a trifluoromethyl at the para position. It is understood that compounds of formula (I) may have other substituents, but include the above groups. Without being bound to any particular theory, the applicant believes that inhibition of metabolism at both the ortho and para positions improves duration after oral administration or injection.

[0115] The following examples are intended to be illustrative and non-limiting and represent specific embodiments of the present invention. [ka] TIFF2024523313000026.tif194117 and each stereoisomer of the above compound.

[0116] In another aspect, disclosed is a compound of formula (II) [ka] [During the ceremony, A1 is -CF3 or -CHF2; Cy1 is [ka] Selected from; Cy2 is [ka] and T1 is [ka] TIFF2024523313000031.tif222145TIFF2024523313000032.tif142148 or a salt thereof.

[0117] In one embodiment, disclosed is a compound of formula (IIa) [ka] (wherein A1, Cy1, Cy2 and T1 are as defined above). or a salt thereof.

[0118] In another embodiment, disclosed is a compound of formula (IIb): [ka] (wherein A1, Cy1, Cy2 and T1 are as defined above). or a salt thereof.

[0119] In certain embodiments, A1 of formula (II), formula (IIa) or formula (IIb) is -CF3.

[0120] In certain embodiments, Cy1 of formula (II), formula (IIa) or formula (IIb) is [ka] It is.

[0121] In certain embodiments, Cy2 of formula (II), formula (IIa) or formula (IIb) is [ka] It is.

[0122] In certain embodiments, T1 of formula (II), formula (IIa) or formula (IIb) is [ka] It is.

[0123] In certain embodiments, disclosed is a compound of formula (II), (IIa) or (IIb), A1 is -CF3; Cy1 is [ka] Selected from; Cy2 is [ka] and; T1 is [ka] TIFF2024523313000041.tif227145TIFF2024523313000042.tif94145 or a salt thereof.

[0124] In certain embodiments, disclosed is a compound of formula (II), formula (IIa) or formula (IIb), A1 is -CF3; Cy1 is [ka] and; Cy2 is [ka] Selected from; T1 is [ka] TIFF2024523313000046.tif188150TIFF2024523313000047.tif50136 or a salt thereof.

[0125] In certain embodiments, disclosed is a compound of formula (II), formula (IIa) or formula (IIb), A1 is -CF3; Cy1 is [ka] and; Cy2 is [ka] Selected from; T1 is [ka] is or a salt thereof.

[0126] In another aspect, disclosed is a compound of formula (III): [ka] [During the ceremony, A1 is -CF3 or -CHF2; Cy3 is [ka] Selected from; Cy4 is [ka] and; T2 is [ka] selected from or a salt thereof.

[0127] In one embodiment, disclosed is a compound of formula (IIIa) [ka] (wherein A1, Cy3, Cy4 and T2 are as defined above). or a salt thereof.

[0128] In another embodiment, disclosed is a compound of formula (IIIb): [ka] (wherein A1, Cy3, Cy4 and T2 are as defined above). or a salt thereof.

[0129] In certain embodiments, A1 of formula (III), formula (IIIa), or formula (IIIb) is -CF3.

[0130] In certain embodiments, Cy3 of formula (III), formula (IIIa) or formula (IIIb) is [ka] It is.

[0131] In certain embodiments, T2 of formula (III), formula (IIIa) or formula (IIIb) is [ka] It is.

[0132] In certain embodiments, disclosed is a compound of formula (III), formula (IIIa) or formula (IIIb), A1 is -CF3; Cy3 is [ka] and; Cy4 is [ka] Selected from; T3 is [ka] is or a salt thereof.

[0133] The following examples are intended to be illustrative and non-limiting and represent specific embodiments of the present invention.

[0134] The analysis was carried out using a Waters Acquity UPLC Liquid Chromatography (LC) system coupled to a Waters SQ Detector 2 single quadrupole mass spectrometer (MS) detector. UV (DAD) collection was performed with a scan range of 200-400 nm (resolution 1.2 nm). The MS was operated with an electrospray ionization source (ESI) in both positive and negative ion modes. Capillary voltage 3.50 (kV), cone voltage 35 (V), and desolvation temperature 550°C. Desolvation gas flow rate 1000 (L / h), cone gas flow rate 50 (L / h). The MS collection range was set to 100-1500 m / z. The MS scan cycle time was 0.5 s. Data collection was performed using Waters Masslynx software.

[0135] Method A: The analysis was carried out on an Acquity UPLC BEH C18 column with a length of 50 mm, an internal diameter of 2.1 mm and a particle size of 1.7 μm. The mobile phase used was: A=water (containing 0.1% formic acid) / B=CH3CN (containing 0.1% formic acid).

[0136] Method B: The analysis was carried out on an Acquity UPLC BEH C18 column with a length of 50 mm, an internal diameter of 2.1 mm and a particle size of 1.7 μm. The mobile phase used was: A=water (containing 0.1% formic acid) / B=CH3CN.

[0137] Method C:The analysis was carried out on an Acquity UPLC BEH C18 column with a length of 50 mm, an internal diameter of 2.1 mm and a particle size of 1.7 μm. The mobile phase used was: A=water (containing 10 mM ammonium acetate) / B=CH3CN.

[0138] The analysis was carried out using an Ultra High Performance Liquid Chromatography (UHPLC) system (Make-Thermo Scientific) coupled with an ion trap mass analyzer. UV collection was performed with a scan range of 200-400 nm (1 nm resolution). MS was operated with an electrospray ionization source (ESI) using sheath gas flow (arb): 40, auxiliary gas flow (arb): 20, sweep gas flow (arb): 1, spray voltage (kv): 5, capillary temperature (°C): 350, capillary voltage (V): 30, tube lens (V): positive mode 30 and negative mode -30 in both positive and negative ion modes. MS collection range was set at 100-2000 m / z. MS scan cycle time was 3 microscans. Data collection was performed using Xcalibur software.

[0139] Method D: The analysis was carried out on an Ascentis Express C18 with a length of 5 cm, an internal diameter of 2.1 mm and a particle size of 2.7 μm. The mobile phase used was: A=water (containing 0.1% formic acid) / B=100% CH3CN.

[0140] The analysis was carried out using a Liquid Chromatography (LC) system coupled to a quadrupole mass spectrometry (MS) detector. UV (DAD) collection was performed with a scan range of 200-400 nm.

[0141] LC-MS, analytical method E: Instrument: SHIMADZU LCMS - UFLC 20-AD - LCMS 2020 MS detector; Column: Ascentis Express C18 2.7 μm, 50 × 3.0 mm; Eluent A: water + 0.05% trifluoroacetic acid by volume, Eluent B: CH3CN + 0.05% trifluoroacetic acid by volume.

[0142] LC-MS, analytical method F: Instrument: SHIMADZU LCMS - UFLC 20-AD - LCMS 2020 MS detector; Column: Kinetex EVO C18 2.6μm, 50×3.0mm; Eluent A: water + 0.05% ammonium bicarbonate by volume, Eluent B: CH3CN.

[0143] As used herein: aq indicates aqueous, br indicates broad line, CH3CN indicates acetonitrile, d indicates doublet, dd indicates doublet of doublets, DCM indicates dichloromethane, DCE indicates dichloroethane, DIPEA indicates N-diisopropylethylamine, DMF indicates N,N-dimethylformamide, DMSO indicates dimethylsulfoxide, ee indicates enantiomeric excess, ES indicates electrospray ionization, EtOAc indicates ethyl acetate, h indicates time (s), and HATU indicates 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide. hexafluorophosphate, HPLC indicates high performance liquid chromatography, iPrOH indicates isopropanol, J indicates coupling constant, LCMS indicates liquid chromatography-mass spectrometry, m / z indicates mass to charge ratio, M indicates molar concentration, m indicates multiplet, MeOH indicates methanol, min. indicates minutes, NaHCO3 indicates sodium bicarbonate, Na2CO3 indicates sodium carbonate, NEt3 indicates triethylamine, NMR indicates nuclear magnetic resonance, q indicates quartet, quint indicates quintet, rt indicates room temperature, R t indicates retention time, s indicates singlet, sat. indicates saturation, T indicates temperature, t indicates triplet, td indicates triplet of doublets, THF indicates tetrahydrofuran, wt indicates weight, and δ indicates chemical shift. EXAMPLES

[0144] 4-((R * )-5-(3-bromo-2-fluoro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((S)-1-ethyl-5-oxopyrrolidin-3-yl)-2-methylbenzamide (Example 1.1) And, 4-((S * )-5-(3-bromo-2-fluoro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((S)-1-ethyl-5-oxopyrrolidin-3-yl)-2-methylbenzamide (Example 1.2) [ka] To a stirred solution of 2-[3-bromo-2-fluoro-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.3 g, 3.5 mmol) in THF (15 mL) and water (7.5 mL) was added dipotassium carbonate (1.02 g, 7.38 mmol) and the mixture was degassed with N2-gas for 10 min. 2-Bromo-3,3,3-trifluoro-prop-1-ene (0.76 g, 4.3 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.25 g, 0.36 mmol) were added and the reaction mixture was heated at 80° C. for 3 h. The mixture was then cooled to room temperature and extracted with diethyl ether (2×10 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure to give 1-bromo-2-fluoro-5-(trifluoromethyl)-3-[1-(trifluoromethyl)vinyl]benzene as a brown liquid, which was used immediately in the next step without further purification.

[0145] To a stirred solution of methyl 4-(hydroxyiminomethyl)-2-methyl-benzoate (500 mg, 2.59 mmol) in DMF (5 mL) was added N-chlorosuccinimide (0.45 g, 3.4 mmol) at room temperature and the mixture was heated at 40° C. for 10 min. The mixture was then cooled to 0° C. and 1-bromo-2-fluoro-5-(trifluoromethyl)-3-[1-(trifluoromethyl)vinyl]benzene (1.05 g, 3.12 mmol) was added, followed by NEt3 (0.40 mL, 2.85 mmol) and the reaction was stirred at room temperature for 3 h. The reaction mixture was quenched by the addition of water (10 mL) and extracted with EtOAc (30 mL). The organic layer was washed with brine (3×15 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (0-20% EtOAc in petroleum ether) to give methyl 4-[5-[3-bromo-2-fluoro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoate as a beige semi-solid.

[0146] LC-MS (Method A) R t = 2.78 min, m / z= 528.1 [M+H] + . Lithium hydroxide monohydrate (0.12 g, 2.9 mmol) was added to a stirred solution of methyl 4-[5-[3-bromo-2-fluoro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoate (500 mg, 0.9 mmol) in THF (5 mL) and water (5 mL) at room temperature, and the mixture was heated at 60° C. for 16 h. The mixture was then cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was dissolved in water (5 mL), acidified to pH approx. 2-3 with HCl solution (1 M), and extracted with EtOAc (2×25 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure to give 4-[5-[3-bromo-2-fluoro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoic acid as a beige solid.

[0147] LC-MS (Method D) R t = 2.74 min, m / z= 514.3 [M+H] + . HATU (0.28 g, 0.74 mmol) was added to a stirred solution of 4-[5-[3-bromo-2-fluoro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoic acid (0.31 g, 0.60 mmol) and (S)-4-amino-1-ethylpyrrolidin-2-one·HCl (121 mg, 0.73 mmol) in DMF (5 mL) followed by DIPEA (0.32 mL, 1.8 mmol) at room temperature and the mixture was stirred for 2 h. The reaction mixture was quenched by adding water (5 mL) and extracted with EtOAc (3×15 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (0-50% EtOAc in petroleum ether) to give the title compound.

[0148] LC-MS (Method B) Rt = 2.26 min, m / z= 624.1 [M+H] + . 1 H NMR (DMSO-d6, 400 MHz) δ 8.77 (d, J = 6.8 Hz, 1 H), 8.45-8.40 (m, 1 H), 7.96-7.91 (m, 1 H), 7.68-7.61 (m, 2 H), 7.42 (d, J = 8.0 Hz, 1 H), 4.55 (d, J = 18 Hz, 1 H), 4.53-4.47 (m, 1 H), 4.38 (d, J = 18 Hz, 1 H), 3.72 (dd, J = 10, 7.2 Hz, 1 H), 3.29-3.17 (m, 3 H), 2.68-2.61 (m, 1 H), 2.37 (s, 3 H), 2.34-2.25 (m, 1 H), 1.03 (t, J = 7.2 Hz, 3 H). The two enantiomers were separated by SFC. The separation was carried out on Chiralcel-OJ-H (column dimensions: 250 mm x 30 mm (5 μm), flow rate: 95.0 g / min, and a CO2-based mobile phase with 10% iPrOH containing 0.2% N,N-isopropylamine as an additive) and was shown in Example 1.1: "4-((R * )-5-(3-bromo-2-fluoro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((S)-1-ethyl-5-oxopyrrolidin-3-yl)-2-methylbenzamide" and Example 1.2: "4-((S * )-5-(3-bromo-2-fluoro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((S)-1-ethyl-5-oxopyrrolidin-3-yl)-2-methylbenzamide" was obtained.

[0149] The following compounds were similarly prepared by the methods of Example 1.1 and Example 1.2. [Table 1] TIFF2024523313000064.tif217165TIFF2024523313000065.tif208165TIFF2024523313000066.tif124164 [Table 2] The compounds of the present invention are valuable active ingredients for use in controlling pests. The term "pest" includes external and internal parasites on and inside animals and in the field of hygiene. In particular, pests are fleas, ticks, mites, flies, worms and lice. Even more particularly, pests are fleas and ticks.

[0150] Animals in the context of the present invention are understood to include vertebrates. In this context, the term "vertebrates" is understood to include, for example, fish, amphibians, reptiles, birds and mammals (including humans). One preferred group of vertebrates according to the present invention includes warm-blooded animals, which include livestock (e.g., cows, horses, pigs, sheep and goats), poultry (e.g., chickens, turkeys, guinea fowl and geese), fur animals (e.g., minks, foxes, chinchillas and rabbits, etc.) and companion animals (e.g., ferrets, guinea pigs, rats, hamsters, cats and dogs), and also humans. A further group of preferred vertebrates according to the present invention includes fish (including salmon).

[0151] In the context of the present invention, ectoparasites are understood to be, in particular, insects, acarines (mites and ticks) and crustaceans (sea lice). These include insects of the following orders: Lepidoptera, Coleoptera, Homoptera, Hemiptera, Heteroptera, Diptera, Dictyoptera, Thysanoptera, Orthoptera, Anoplura, Siphonaptera, Mallophaga, Thysanura, Isoptera, Psocoptera and Hymenoptera. However, ectoparasites that may be mentioned in particular are those which cause damage to humans or animals and carry pathogens, such as flies, such as, for example, the house fly Musca domestica, Musca vetustissima, Musca autumnalis, Fannia canicularis, fruit flies Sarcophaga carnaria, sheep blowflies Lucilia cuprina, Lucilia sericata, cow flies Hypoderma bovis, cow flies Hypoderma lineatum, Chrysomyia chloropyga, human dung flies Dermatobia hominis, screwworm flies Cochliomyia hominivorax, horse flies Gasterophilus intestinalis, Oestrus ovis, biting flies such as Haematobia irritans irritans, Haematobia irritans exigua, Stomoxyscalcitrans, Tabanids (which includes the subfamilies of the family Tabanidae), for example Haematopota spp. (e.g. Haematopota pluvialis) and Tabanus spp. (e.g. Tabanus nigrovittatus), as well as the subfamily Chrysopsinae, for example Chrysops spp. (e.g. Chrysops caecutiens); Hippoboscids, for example Melophagus ovinus (sheep ked); tsetse flies, for example Glossinia spp.; Other biting insects, for example midges, for example Ceratopogonidae (biting midges), Simuliidae (Blackflies), Psychodidae (Sandflies); also blood-sucking insects, for example mosquitoes, for example Anopheles spp, Aedes spp and Culex spp, fleas, for example Ctenocephalides felis and Ctenocephalides canis (cat and dog fleas), Xenopsylla cheopis, Pulex irritans, Ceratophyllus gallinae, Dermatophilus penetrans, blood-sucking lice (order Anoplura), e.g. Linognathus spp, Haematopinus spp, Solenopotes spp, Pediculus spp,humanis; and also chewing lice (Mallophaga), such as Bovicola (Damalinia) ovis, Bovicola (Damalinia) bovis, and other Bovicola spp. Ectoparasites further include members of the following orders: Acarina, for example mites, such as Chorioptes bovis, Cheyletiella spp., Dermanyssus gallinae, Ortnithonyssus spp., Demodex canis, Sarcoptes scabiei, Psoroptes ovis and Psorergates spp., and ticks. Representative ticks include, for example, the genus Boophilus, Amblyomma, Anocentor, Dermacentor, Haemaphysalis, Hyalomma, Ixodes, Rhipicentor, Margaropus, Rhipicephalus, Argas, and Otobi. and the genera Otobius and Ornithodoros, which preferably infest vertebrates, such as warm-blooded animals, such as livestock (e.g., cattle, horses, pigs, sheep and goats), poultry (e.g., chickens, turkeys, guinea fowl and geese), fur animals (e.g., mink, foxes, chinchillas and rabbits) and companion animals (e.g., ferrets, guinea pigs, rats, hamsters, cats and dogs), and also humans and fish.

[0152] The inventive compounds according to the invention are active against all or individual developmental stages of normally susceptible animal pests and also against those that are resistant to commonly used parasiticides. This applies in particular to resistant insects and members of the order Acarina. The insecticidal, ovicidal and / or acaricidal effect of the active substances according to the invention can be expressed directly (i.e. by killing pests or destroying their eggs, for example immediately or after some time has passed after molting) or indirectly (for example by reducing the number of eggs laid and / or the hatching rate) with good efficacy corresponding to a killing rate (mortality rate) of at least 50-60%.

[0153] The compounds of the present invention can further be used against sanitary pests, in particular against sanitary pests of the orders Diptera (Muscidae, Sarcophagidae, Anophilidae and Culicidae); Orthoptera; Dictyoptera (e.g. Blattidae (cockroaches), e.g. Blatella germanica, Blatta orientalis, Periplaneta americana) and Hymenoptera (e.g. Formicidae (ants) and Vespidae (wasps)).

[0154] The compounds of formula (I) are furthermore active against ectoparasites of fish, in particular the subclass Copepoda (e.g. Siphonostomatoida (sea lice)), while being well tolerated by the fish.

[0155] The compounds of formula (I) can also be used against worms of the class Cestoda (which includes the subclass Eucestoda and Cestodaria).

[0156] The compounds of the invention also have long-lasting efficacy against plant-parasitic mites and insects. In the case of spider mites of the order Acarina, the compounds of the invention are effective against eggs, nymphs and adults of the family Tetranychidae (Tetranychus spp. and Panonychus spp.).

[0157] They are highly active against sap-sucking insects of the suborder Homoptera, in particular against sap-sucking insects of the families Aphididae, Delphacidae, Cicadellidae, Psyllidae, Loccidae, Diaspididae and Eriophydidae (e.g. rust mites on citrus fruits); against sap-sucking insects of the orders Hemiptera, Heteroptera and Thysanoptera, as well as against plant-feeding insects of the orders Lepidoptera, Coleoptera, Diptera and Orthoptera.

[0158] They are likewise suitable as soil insecticides against pests in the soil.

[0159] Thus, the compounds of formula (I) are effective against all developmental stages of sap-sucking and feeding insects on crops such as cereals, cotton, rice, corn, soybean, potato, vegetables, fruit, tobacco, hops, citrus, avocado and other crops.

[0160] The compounds of formula (I) are further active against plant nematodes such as Meloidogyne spp., Heterodera spp., Pratylenchus spp., Ditylenchus spp., Radopholus spp., and Rizoglyphus spp.

[0161] The compounds of the present invention are effective against helminths. Helminths are commercially important because they cause serious diseases in mammals and poultry, such as sheep, pigs, goats, cattle, horses, donkeys, camels, dogs, cats, rabbits, guinea pigs, hamsters, chickens, turkeys, guinea fowl and other domestic birds, as well as in exotic birds. Typical nematodes are: Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostonum, Oesophagostonum, Charbertia, Trichuris, Strontium, and the like. The genera Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris and Parascaris. The above-mentioned trematodes can be particularly exemplified by the Fasciolideae family, in particular Fasciola hepatica.

[0162] The pesticidal activity of the compounds represented by formula (I) according to the present invention corresponds to a mortality rate of about 50-60% of the above pests, more preferably a mortality rate of more than 90%, and most preferably a mortality rate of 95-100%. Preferably, the compounds of formula (I) are used internally or externally in unmodified form or, preferably, together with adjuvants conventionally used in the technical field of formulations, and can thus be processed in known manner to obtain, for example, liquid preparations (e.g., spot-ons, pour-ons, spray-ons, emulsions, suspensions, solutions, emulsions, concentrated solutions), semisolid preparations (e.g., creams, ointments, pastes, gels, liposomal preparations) and solid preparations (e.g., tablets for food additives (including capsules), powders (including soluble powders), granules, or active ingredients embedded in polymeric substances (e.g., implants and microparticles)). As with the compositions, the application method is selected according to the intended purpose and the prevailing circumstances.

[0163] The compound of the present invention can be administered alone or in the form of a composition.In practice, the compound of the present invention is usually administered in the form of a composition, i.e., mixed with at least one acceptable excipient.The proportion and nature of any acceptable excipient are determined by the characteristics of the selected compound of the present invention, the selected route of administration and standard techniques in the veterinary and pharmaceutical fields.

[0164] In one embodiment, the present invention provides a composition comprising a compound of the present invention and at least one acceptable excipient.

[0165] In carrying out such treatment and / or prevention, the compounds of the present invention can be administered in any form and route that makes the compounds bioavailable. The compounds of the present invention can be administered by various routes, including the oral route, in particular by tablets and capsules. The compounds of the present invention can be administered by parenteral routes, more particularly by inhalation, subcutaneous, intramuscular, intravenous, intraarterial, transdermal, intranasal, rectal, intravaginal, intraocular, topical, sublingual and buccal, intraperitoneal, intraadiposally, intrathecal, and via local delivery (e.g., by catheter or stent). Those skilled in the art can easily select the appropriate dosage form and route of administration depending on the specific characteristics of the selected compound, the disorder or condition to be treated, the stage of the disorder or condition, and other relevant circumstances. The pharmaceutical compositions of the present invention may be administered to a subject in the form of, for example, tablets (including chewable tablets), capsules, cachets, lozenges, wafers, elixirs, boli, ointments, transdermal patches, aerosols, inhalants, suppositories, drenches, solutions, injectables and suspensions.

[0166] The term "acceptable excipients" refers to excipients commonly used in preparing veterinary and pharmaceutical compositions and must be pure and non-toxic in the amounts used. They are generally solid, semi-solid or liquid substances that can function as a vehicle or medium for the active ingredient as a whole. Some examples of acceptable excipients can be found in "Remington's Pharmaceutical Sciences and the Handbook of Pharmaceutical Excipients" and include diluents, vehicles, carriers, ointment bases, binders, disintegrants, lubricants, glidants, sweeteners, flavorings, gel bases, sustained release matrices, stabilizers, preservatives, solvents, suspending agents, buffers, emulsifiers, dyes, propellants, coatings, and the like.

[0167] In one embodiment, the composition is adapted for oral administration (e.g., a tablet or capsule, or a liquid formulation, e.g., a solution or suspension adapted for oral administration). In one embodiment, the composition is adapted for oral administration (e.g., a chewable formulation adapted for oral administration). In yet another embodiment, the composition is a liquid or semisolid formulation, e.g., a solution or suspension or paste adapted for parenteral administration.

[0168] In one embodiment, the composition is adapted for injectable administration (eg, a solution or suspension adapted for injectable administration).

[0169] Particular compositions for use in subjects in the treatment and / or control of nematodes / helminths include: solutions; injections; emulsions, such as classical emulsions, microemulsions and self-emulsifying compositions (which are water-free organic compositions, preferably oil-based compositions, that form emulsions with bodily fluids when added to the subject's body); suspensions (drenches); pour-on formulations; food additives; powders; tablets (which include effervescent tablets); boli; capsules (which include microcapsules); and chewable treats. In particular, the composition is in the form of a tablet, capsule, food additive or chewable treat.

[0170] The compositions of the present invention are prepared by methods well known in the veterinary and pharmaceutical arts and contain at least one of the compounds of the present invention as an active ingredient. The amount of the compound of the present invention can vary depending on its particular form, and can conveniently be 1% to about 50% by weight of the unit dosage form. The pharmaceutical compositions of the present invention are preferably formulated in unit dosage form, and each dosage typically contains about 0.5 mg to about 100 mg of the compound of the present invention. To achieve a change in therapeutic dose, one or more unit dosage forms can be used.

[0171] In one embodiment, the present invention further provides a method of treating pests, comprising administering to a subject in need of such treatment an effective amount of a compound of formula (I) or a salt thereof, optionally further comprising an effective amount of at least one additional active compound.

[0172] In one embodiment, the present invention further provides a method for controlling pests, comprising administering to a subject in need of such control an effective amount of a compound of formula (I) or a salt thereof, optionally further comprising an effective amount of at least one additional active compound.

[0173] In one embodiment, the present invention further provides a method of treating or controlling a pest, the method comprising contacting the environment of a subject with an effective amount of a compound of formula (I) or a salt thereof, optionally further comprising an effective amount of at least one additional active compound.

[0174] Thus, the present invention also provides the use of the compound of the present invention as a medicament, including the use for producing a medicament. In one embodiment, the present invention provides the manufacture of a medicament comprising a compound of formula (I) or a salt thereof for treating a pest. In one embodiment, the present invention provides the manufacture of a medicament comprising a compound of the present invention or a salt thereof for controlling a pest.

[0175] The terms "treating," "to treat," "treated," or "treatment" include, but are not limited to, inhibiting, slowing, halting, reducing, ameliorating, reversing the progression or severity of existing symptoms, or preventing a disorder, condition, or disease. For example, an adult heartworm infection would be treated by administering a compound of the invention. Treatment may be applied or administered therapeutically.

[0176] The terms "control", "controlling" or "controlled" include, but are not limited to, lowering, reducing or ameliorating the risk of a symptom, disorder, condition or disease, and protecting an animal from a symptom, disorder, condition or disease. Control may refer to therapeutic, prophylactic or preventative administration. For example, larvae or immature pests may be asymptomatic, but are controlled by acting on the larvae or immature pests to prevent the infection from progressing to a symptomatic or debilitating infection by mature pests.

[0177] Thus, the use of the compounds of the invention in the treatment and / or control of pests (particularly helminths, especially endoparasitic nematodes and trematodes) refers to the use of the compounds of the invention to act on various forms of pests throughout their life cycle, regardless of whether the subject is showing symptoms including morbidity or mortality, and regardless of the stage of attack of the pest.

[0178] As used herein, "administration to a subject" includes, but is not limited to, dermal, subcutaneous, intramuscular, mucosal, submucosal, transdermal, oral or intranasal administration. Administration may include injection or topical administration (e.g., pour-on or spot-on). The pour-on or spot-on method is particularly advantageous for use with herd animals such as cattle, horses, sheep or pigs, where it is difficult or time-consuming to treat all animals orally or by injection. This method is highly favored by animal breeders because of its simplicity, and because it can of course also be used with all other animals, including individual domestic animals or pets, and because it can often be performed without the professional presence of a veterinarian.

[0179] The terms "subject" and "patient" include humans, as well as non-human mammals and fish, vertebrates as described herein, such as dogs, cats, mice, rats, guinea pigs, rabbits, ferrets, cows, horses, sheep, goats, and pigs. Particular subjects are mammalian pet or companion animals, such as dogs and cats, and also mice, guinea pigs, ferrets, and rabbits.

[0180] The term "effective amount" refers to an amount that provides the desired benefit to the subject, and includes both therapeutic and prophylactic administration, which will vary for each individual subject and will depend on many factors, such as the subject's overall health and the severity of the underlying cause of the condition being treated, concurrent treatments, and the amount of the compound of the invention used to maintain the desired response at a beneficial level.

[0181] The effective amount can be readily determined by the attending diagnostician as one of ordinary skill in the art by using known techniques and by observing results obtained under similar circumstances. In determining the effective amount, the dose, many factors are considered by the attending diagnostician, including, but not limited to: the species of the patient; its size, age and general health; the particular condition, disorder, infection or disease involved; the extent or involvement or severity of the condition, disorder or disease; the response of the individual patient; the particular compound administered; the method of administration; the bioavailability characteristics of the administered preparation; the selected dosing regimen; the use of concomitant medications; and other relevant circumstances. The effective amount, the therapeutic dose of the present invention is expected to be in the range of 0.5 mg to 100 mg. The specific amount can be determined by one of ordinary skill in the art. These doses are based on subjects weighing about 1 kg to about 20 kg, although the diagnostician can determine the appropriate dose for subjects weighing outside this weight range. The effective amount, the therapeutic dose of the present invention is expected to be in the range of 0.1 mg to 10 mg per kg of subject's body weight. Dosing regimens are anticipated to be monthly, quarterly, twice yearly or yearly administration.

[0182] The compounds of the invention may be combined with one or more other active compounds or therapies for the treatment of one or more disorders, diseases or conditions for which it is indicated, including the treatment of pests. The compounds of the invention may be administered in combination with one or more compounds or therapies for the treatment of pests and other disorders, either simultaneously, sequentially or separately.

[0183] It is therefore understood that the compositions and methods of the present invention include, optionally, an effective amount of at least one additional active compound. Additional active compounds useful in the present invention include those used to treat fleas, ticks, flies and mosquitoes, and may include macrocyclic lactones such as milbemycin oxime, imidacloprid, spinosad, pyriproxyfen, premethrin, S-methoprene, praziquantel and moxidectin. Further exemplary additional active compounds can include, but are not limited to, afoxolaner, broflanilide, fluralaner, fluxamethamide, isocycloceram, lotilaner, modofuraner, nicofluprole, sarolaner, tigoraner, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, parabendazole, thiabendazole, triclabendazole, amitraz, demiditraz, clorsulon, closantel, oxyclonazide, lafoxanide, cyphenothrin, deltamethrin, flumethrin, permethrin, cyromazine, delcantel, diamphenetide. , dicyclanil, dinotefuran, imidacloprid, nitenpyram, thiamethoxam, abamectin, doramectin, emamectin, eprinomectin, ivermectin, moxidectin, selamectin, milbemycin oxime, emodepside, epsiprantel, fipronil, fluazuron, fluhexafon, indoxacarb, levamisole, lufenuron, metaflumizone, methoprene, monepantel, morantel, niclosamide, nitroscanate, nitroxynil, novaluron, oxantel, praziquantel, pyrantel, pyriprole, pyriproxyfen, cisapronil, spinosad, spinetoram, and triflumezopyrim, or a salt of any of the above.

[0184] The activity of the compounds of the present invention can be confirmed in a variety of ways, including in vitro and in vivo methods.

[0185] Example A In vitro evaluation of feeding activity against adult cat fleas To prepare the test blood mixture for feeding to the fleas, the test substance is dissolved in dimethyl sulfoxide and diluted to the desired concentration with citrated bovine blood. To assemble the test apparatus, approximately 20 unfed adult male and female cat fleas (Ctenocephalides felis) are placed in a chamber closed at the top and bottom with gauze. One end of a metal cylinder is sealed with a parafilm membrane, the sealed bottom is placed on the chamber, and the test blood mixture is placed. The test blood mixture can be sucked by the fleas through the parafilm membrane. The blood cylinder part of the assembled test apparatus is contained at approximately 37°C in an isolated air-heated container above an isolation carrier plate that holds the flea chamber. The flea chamber part is kept at room temperature. After 48 hours, the insecticidal activity against the fleas is measured. 100% means that all fleas are dead or moribund; 0% means that no fleas are affected by the administered dose. From the dose-response curve, the EC50 of each compound was calculated (four-parameter logistic curve fitting). If the EC50 was below 20 ppm, the compound showed good insecticidal activity against cat fleas (Ctenocephalides felis).

[0186] In this test, for example, the following compounds from the preparation examples were 50 Showed <1 ppm: Examples 1.5, 1.8, 1.9, 1.11, 1.13, 1.14, 2.3, and 3.1.

[0187] In this test, for example, the following compounds from the preparation examples were 50 <5 ppm: Examples 1.1, 1.5, 1.8, 1.9, 1.11, 1.13, 1.14, 2.3, 2.4, and 3.1.

[0188] In this test, for example, the following compounds from the preparation examples were 50 <20 ppm: Examples 1.1, 1.3, 1.4, 1.5, 1.8, 1.9, 1.11, 1.13, 1.14, 2.3, 2.4, and 3.1.

[0189] With respect to the above data, when a single isomer was tested without knowing the absolute configuration of the isomer, the data indicates that the test substance is one isomer or another (e.g., Example 1.1 or its enantiomer).

[0190] Example B In vitro evaluation of contact activity against adult Rhipicephalus sanguineus In vitro contact testing with ticks is performed using adult males and females of the brown dog tick (Rhipicephalus sanguineus). To coat the test vials, the test substance is dissolved in acetone pa and diluted with acetone pa to the desired concentration. The solution is then evenly applied to the inside walls and bottom of the glass vial by rolling and rocking on an orbital shaker until the solvent has completely evaporated. For example, a 900 ppm test substance solution will have a concentration of 5 μg / cm 2 An area-based dose of 0.01 mg / cm2 is achieved. After complete evaporation of the solvent, 5-10 adult ticks are applied to each coated test vial, which is then sealed with a plastic lid with a hole and incubated in a horizontal position in the dark at room temperature and ambient humidity. The acaricidal activity is measured after 48 hours. For this purpose, the test tube is tapped to move the ticks to its bottom, and the test vial is then incubated on a hot plate at 45-50°C for no more than 5 minutes. Ticks that remain motionless at the bottom of the test vial or that move jerkily without intentionally climbing to avoid the heat are considered dead or moribund, respectively. 100% acaricidal activity means that all ticks are dead or moribund. 0% acaricidal activity means that no dead or moribund ticks were found. From the dose-response curves, the respective EC50s were calculated (four-parameter logistic curve fitting). EC50s of 5 μg / cm2 were calculated (four-parameter logistic curve fitting). 2 At application rates below this the substance exhibits good acaricidal activity against brown dog ticks (Rhipicephalus sanguineus).

[0191] In this test, for example, the following compounds from the preparation examples were 50 <0.04μg / cm 2 Examples 1.3, 1.5, 1.8, and 3.1 were shown.

[0192] In this test, for example, the following compounds from the preparation examples were 50 <0.25 μg / cm 2 Examples 1.1, 1.3, 1.4, 1.5, 1.8, and 3.1 were shown.

[0193] In this test, for example, the following compounds from the preparation examples were 50 <1μg / cm 2 Examples 1.1, 1.3, 1.4, 1.5, 1.8, 2.3, and 3.1 were shown.

[0194] With respect to the above data, when a single isomer was tested without knowing the absolute configuration of the isomer, the data indicates that the test substance is one isomer or another (e.g., Example 1.1 or its enantiomer).

[0195] Example C In vitro evaluation of contact activity against adult cat fleas In vitro contact testing with ticks is performed using adult males and females of cat fleas (Ctenocephalides felis). To coat the test vials, the test substance is dissolved in acetone pa and diluted with acetone pa to the desired concentration. The solution is then evenly applied to the inside walls and bottom of the glass vial by rolling and rocking on an orbital shaker until the solvent has completely evaporated. For example, a 900 ppm test substance solution will have a concentration of 5 μg / cm 2 An area-based dose of is achieved.

[0196] After the solvent has completely evaporated, about 10 adult fleas are applied to each coated test vial, which is then sealed with a plastic lid with holes and incubated in a horizontal position in the dark at room temperature and ambient humidity. Insecticidal activity is measured after 48 hours. Fleas that remain motionless at the bottom of the test vial or move jerkily without occasional jumps or walking in a straight line are considered dead or moribund, respectively. 100% insecticidal activity means that all fleas are dead or moribund. 0% insecticidal activity means that no fleas were affected. From the dose-response curves, the respective EC50s were calculated (four-parameter logistic curve fitting). EC50s of 5 μg / cm 2 At application rates below this, the substance exhibits good insecticidal activity against the cat flea (Ctenocephalides felis).

[0197] In this test, for example, the following compounds from the preparation examples were 50 <0.05μg / cm 2 Shown in: Example 3.1.

[0198] In this test, for example, the following compounds from the preparation examples were 50 <0.1μg / cm 2 Examples 1.1, 1.3, 1.4, 1.8, and 3.1 were given.

[0199] With respect to the above data, when a single isomer was tested without knowing the absolute configuration of the isomer, the data indicates that the test substance is one isomer or another (e.g., Example 1.1 or its enantiomer).

[0200] Example D In vitro evaluation of systemic activity against engorged female bullfrog ticks To prepare the test compound mixture for injection into ticks, the test substance is dissolved in dimethyl sulfoxide and diluted with the same solvent to the desired concentration. 1 μL of the test mixture is injected into each abdomen of 5 engorged female adult bull ticks (Rhipicephalus (Boophilus) microplus). The ticks are transferred individually to a single compartment of a 5×5 replica plate and kept in a climate chamber (28° C., 85% relative humidity). The acaricidal activity against bull ticks is evaluated after 7 days by evaluating the fertile eggs laid. Eggs that do not appear normal can be kept in a climate chamber [28° C., 85% relative humidity] until the larvae hatch after 42 days. 100% acaricidal activity means that no ticks laid eggs or the eggs laid were infertile; 0% means that all eggs are fertile. From the dose-response curve, the respective EC50 is calculated (four-parameter logistic curve fitting). If the EC50 is below 10 μg / tick application rate, the substance shows good systemic acaricidal activity against the bullfrog tick (Rhipicephalus microplus).

[0201] In this test, for example, the following compounds from the preparation examples were 50 <1 μg / tick: Examples 1.5, 1.8, 2.3 and 3.1.

[0202] In this test, for example, the following compounds from the preparation examples were 50 <2 μg / tick were shown: Examples 1.1, 1.3, 1.5, 1.8, 2.3, 2.4 and 3.1.

[0203] In this test, for example, the following compounds from the preparation examples were 50 <10 μg / tick were shown for: Examples 1.1, 1.3, 1.5, 1.8, 2.1, 2.2, 2.3, 2.4 and 3.1.

[0204] With respect to the above data, when a single isomer was tested without knowing the absolute configuration of the isomer, the data indicates that the test substance is one isomer or another (e.g., Example 1.1 or its enantiomer).

[0205] Example E In vitro evaluation of contact activity against larval Bovis ticks This in vitro contact test is performed using larvae of the bullfrog tick (Rhipicephalus microplus). To coat the test vials, the test substance is dissolved in acetone pa and diluted with acetone pa to the desired concentration. The solution is then evenly applied to the inside walls and bottom of the glass vial by rolling and rocking on an orbital shaker until the solvent has completely evaporated. For example, a 900 ppm test substance solution will have a concentration of 5 μg / cm 2 An area-based dose of 0.01 mg / kg is achieved. After complete evaporation of the solvent, 10-20 larval ticks are applied to each coated test vial, which is then sealed with a plastic lid with holes and incubated in a horizontal position in a tray maintained in a climate chamber (28°C, 85% relative humidity). The acaricidal activity is measured after 48 hours. For this purpose, the vials are placed vertically and the efficacy is evaluated using the natural negative geotactic behavior of the bovis tick larvae. Ticks that remain motionless at the bottom of the test vial or that move jerkily without intentionally climbing are considered dead or moribund, respectively. 100% acaricidal activity means that all tick larvae are dead or moribund. 0% acaricidal activity means that no tick larvae were affected. From the dose-response curves, the respective EC50s were calculated (four-parameter logistic curve fitting). EC50 is 5μg / cm 2 At application rates below this the substance exhibits good acaricidal activity against brown dog ticks (Rhipicephalus sanguineus).

[0206] In this test, for example, the following compounds from the preparation examples were50 <0.01μg / cm 2 Examples 1.3, 1.5, and 3.1 are given.

[0207] In this test, for example, the following compounds from the preparation examples were 50 <0.1μg / cm 2 Examples 1.1, 1.3, 1.4, 1.5, 2.3, and 3.1 are given.

[0208] With respect to the above data, when a single isomer was tested without knowing the absolute configuration of the isomer, the data indicates that the test substance is one isomer or another (e.g., Example 1.1 or its enantiomer).

Claims

1. Formula (I): 【Chemical 1】 [In the formula, A １ is selected from the group consisting of CF ３ , CHF ２ , CH ２ F and CF ２ CF ３ ; A ２ is O or S; R １ is selected from the group consisting of hydrogen and halogen; R ２ is selected from the group consisting of hydrogen, halogen, difluoromethyl and trifluoromethyl; ; R ３ is selected from the group consisting of hydrogen, halogen and trifluoromethyl; R ４ is selected from the group consisting of hydrogen, halogen, difluoromethyl and trifluoromethyl; ; R ５ is selected from the group consisting of hydrogen and halogen; Provided that R １ is hydrogen only when ２ R is trifluoromethyl, difluoromethyl or bromo; R ５ is hydrogen only when ４ R is trifluoromethyl or bromo; R ３ is hydrogen only when ２ R ４ or R R １ , R ３ and R ５ are hydrogen only when ２ R ４When it is trifluoromethyl, all are hydrogen It cannot be so; and, R １ 、R ２ 、R ３ 、R ４ and R ５ At most 3 of them are hydrogen; Q is selected from the group consisting of the following [Chemical Formula 2] ; Here, p is 0, 1 or 2; q is 0, 1, 2 or 3; r is 0 or 1; s is 0, 1 or 2; t is 0 or 1; R ６ is independently selected from the group consisting of the following for each occurrence: halogen; cyano; nitro; hydroxyl; -NH ２ ; -NH(C １ -C ４ alkyl); -N(C １ -C ４ alkyl) ２ ; C ２ -C ５ -alkoxycarbonyl; C １ -C ６ -Al Kill (wherein the alkyl is halogen, cyano, nitro, hydroxyl, oxo, C ３ -C ６ Cycloalkyl, C １ -C ４ Alkoxy, -NH ２ , C １ -C ７ Aminocarbonyl , -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alk Kill, -S(O)C １ -C ４ alkyl and -SO ２ C １ -C ４ selected from the group consisting of alkyl optionally substituted with 1 to 5 substituents that are independently selected; C １ -C ６ -alkoxy ( Here, the alkoxy group is halogen, cyano, nitro, hydroxyl, oxo, C ３ -C ６ Cycloalkyl, C １ -C ４ Alkoxy, -NH ２ , C １ -C ７ Aminocarbonyl, - NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl ２ , -SC １ -C ４ alkyl , -S(O)C １ -C ４ alkyl and -SO ２ C １ -C ４ independently from the group consisting of alkyl optionally substituted with 1 to 5 substituents selected; -NR ８ C(O)(C １ -C ４ alkyl) (wherein this is C １ -C ４ On the alkyl, halogen, cyano, hydroxy Ru, C ３ -C ６ Cycloalkyl, C １ -C ４ Alkoxy, -NH ２ C １ -C ７ Aminoca Rbonyl, -NH(C １ -C ４ alkyl) and -N(C １ -C ４ alkyl) ２ selected from the group consisting of may be substituted with 1 to 5 substituents independently selected therefrom, wherein R ８ is hydrogen and C １ -C ４ independently selected from the group consisting of alkyl); -C(O)NR ８ (C １ -C ４ alkyl) (wherein this is its C １ -C ４ on the alkyl, halogen, cyano, Hydroxyl, C ３ -C ６ Cycloalkyl, C １ -C ４ Alkoxy, -NH ２ 、C １ -C ７ aminocarbonyl, -NH(C １ -C ４ -alkyl) and -N(C １ -C ４ -alkyl) ２ Optionally substituted with 1 to 5 substituents independently selected from the group consisting of, wherein R ８ is independently selected from the group consisting of hydrogen and C １ -C ４ -alkyl); -SC １ -C ６ alkyl, wherein said alkyl is halogen, cyano, nitro, hydroxyl, oxo , C ３ -C ６ Cycloalkyl, C １ -C ４ Alkoxy, -NH ２ , C １ -C ７ Aminocar Bonil, -NH(C １ -C ４ alkyl) and -N(C １ -C ４ alkyl) ２ selected from the group consisting of which may be substituted with 1 to 5 substituents independently selected; and, -S(O)C １ -C ６ alkyl (wherein the alkyl is halogen, cyano, nitro, hydroxyl, o Kiso, C ３ -C ６ Cycloalkyl, C １ -C ４ Alkoxy, -NH ２ 、C １ -C ７ Amino Carbonyl, -NH(C １ -C ４ -alkyl) and -N(C １ -C ４ -alkyl) ２ consisting of Optionally substituted with 1 to 5 substituents independently selected from the group); R ７ In each entity, oxo, C １ -C ４ -alkyl and C ３ -C ６ -cycloalkyl Independently selected from the group consisting of; A ３ is O or S; A ４ is CH or N; A ５ is CH or N; A ６ is CH or N; A ７ is CHO, S, a bond or N; A ８ is CHO, S, a bond or N; A ９ is CH or N; A １０ is CH or N; A １１ is CH or N; A １２ is CH or N; A １３ is CH or N; A １４ is CH or N; A １５ is CH or N; A １６ is NR, O or S, where R is hydrogen, C １ -C ４ alkyl and C ３ -C ６ selected from the group consisting of cycloalkyl; W １ is -O-, -S-, -NR ９ -, -NC(O)R １０ -, -CH ２ - and -C( Selected from the group consisting of -O); W ２ is -O-, -S-, -NR ９ -, -NC(O)R １０ -, -CH ２ - and -C( Selected from the group consisting of -O); Provided that W １ is —O—, —S—, —NR ９ — or —NC(O)R １０ —, when W ２ is , -CH ２ - or -C(O)-; W ２ is —O—, —S—, —NR ９ — or —NC(O)R １０ —, then W １ is , -CH ２ - or -C(O)-; W ３ is non-existence, -O-, -S-, -S(O)-, -S(O) ２ -, -NR ９ -, -C H−, −N−, −CH ２ selected from the group consisting of − and −C(O)−; W ４ is non - existent, -O-, -S-, -S(O)-, -S(O) ２ -, -NR ９ -, -C H−, −N−, −CH ２ selected from the group consisting of − and −C(O)−; W ５ is non - existent, -O-, -S-, -S(O)-, -S(O) ２ -, -NR ９ -, -C H−, −N−, −CH ２ selected from the group consisting of − and −C(O)−; W ６ is non - existent, -O-, -S-, -S(O)-, -S(O) ２ -, -NR ９ -, -C H−, −N−, −CH ２ selected from the group consisting of − and −C(O)−; Here, W １ , W ２ , W ３ and W ４ The bond between is a single bond or a double bond, and can be ; Provided that (i) W １ , W ２ , W ３ and W ４ Among them, two or less do not exist; (ii) W １ , W ２ , W ３ and W ４ Among two or less of them are -O-, -S-, -S(O) -、-S(O) ２ -、-NR ９ - or -C(O)-; (iii) W １ , W ２ , W ３ and W ４ where two of W In combination, there is at least 1 carbon atom between them; (iv) W １ , W ２ , W ３ or W ４ is -CH- and / or -NR ９ -, when W １ , W ２ , W ３ and W ４ a double bond is formed within the ring formed by; R ９ In each entity, hydrogen and C １ -C ６ -alkyl (wherein the alkyl is halo Halogen, cyano, nitro, hydroxyl, oxo, C ３ -C ６ -cycloalkyl, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl) , -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ yl Kill and -SO ２ C １ -C ４ 1 to 5 substituents independently selected from the group consisting of alkyl Optionally substituted with a substituent independently selected from the group consisting of); R １０ In each entity, oxo, C １ -C ４ -alkyl and C ３ -C ６ -cycloalkyl Independently selected from the group consisting of; X is a 5- to 10-membered heteroaryl having 1 or 2 heteroatoms selected from the group of O, S, and N And is; Here, the carbon of the 5- to 10-membered heteroaryl may be substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, hydro Roxyl, C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, hydroxy Ru, oxo, C １ -C ４ alkoxy, -NH ２ C １ -C ７ aminocarbonyl, -NH( C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S (O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl, -C(O)NH-C １ -C ６ Alkyl and -C(O)NH-C １ -C ６ Optionally substituted with 1 to 5 substituents independently selected from the group consisting of haloalkyl ), C ３ -C ６ -cycloalkyl, C １ -C ４ -haloalkyl, C １ -C ４ -alkoxy, -N H ２ ,-NH(C １ -C ４ alkyl),-N(C １ -C ４ alkyl) ２ ,-C(O)NH -C ３ -C ６ Cycloalkyl, -C(O)NH-C １ -C ６ Alkyl and -C(O)NH -C １ -C ６ substituted with 1, 2 or 3 substituents independently selected from the group consisting of haloalkyl May be substituted, Here, any N within the heteroaryl, as long as the valence permits, is hydrogen, C １ -C ４ a Alkyl (wherein the alkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, acetylenyl, ox So, C １ -C ４ Alkoxy, -NH ２ , C １ -C ７ Aminocarbonyl, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl, -SO ２ C １ -C ４ alkyl, -C(O)NH-C ３ -C ６ cyclo a Lucil, -C(O)NH-C １ -C ６ Alkyl and -C(O)NH-C １ -C ６ Haloal Optionally substituted with 1 to 5 substituents independently selected from the group consisting of alkyl) and C ３ -C ６ optionally substituted with a substituent selected from the group consisting of cycloalkyl; Or, X is 【Chemical Formula 3】 Selected from the group consisting of; Here, R １１ is hydrogen, C １ -C ４ -alkyl, C １ -C ４ -haloalkyl, C ３ -C ６ -cyclo Lukil, C ４ -C ７ Alkylcycloalkyl, C ２ -C ７ alkylcarbonyl, C ２ -C ５ alkoxycarbonyl, C ２ -C ６ alkenyl and C ２ -C ６ selected from the group consisting of alkynyl; W is selected from the group consisting of the following: (i) Hydrogen, (ii) C １ - C ６ alkyl [wherein the alkyl is halogen; cyano ； Hydroxy Ru; oxo; C １ -C ４ alkoxy; C ３ -C ６ cycloalkyl (wherein the cycloal The alkyl may be substituted with 1 to 3 substituents independently selected from the group of halogen and cyano may also be); ethynyl; -NH ２ ; C １ -C ７ aminocarbonyl; -NH(C １ -C ４ alkyl); -N(C １ -C ４ alkyl) ２ ; -SC １ -C ４ alkyl; -S(O)C １ -C ４ alkyl; -SO ２ C １ -C ４ alkyl; -C(O)NH-C ３ -C ６ cyclo a Lukyl (where this is halogen, hydroxyl, cyano and C １ -C ４ alkyl (this Here, the alkyl is halogen, cyano, hydroxyl, C １ -C ４ alkoxy, C ３ - C ６ cycloalkyl and -NH ２ substituted with 1 to 5 substituents independently selected from the group consisting of Optionally substituted with 1 to 3 substituents independently selected from the group consisting of); may also be); -C(O)NH-C １ -C ６ alkyl (wherein this is halogen, cyano , hydroxyl, C １ -C ４ alkoxy, C ３ -C ６ cycloalkyl and -NH ２ consisting of Optionally substituted with 1 to 5 substituents independently selected from the group consisting of); -C(O)NH -C １ -C ６ cyanoalkyl (wherein this may be substituted with 1 to 3 halogens) i); -C(O)NH-C １ -C ６ Haloalkyl; -C(O)-4- to 7-membered heterocycle Alkyl (wherein this is bonded by nitrogen and may have 1 or 2 other heteroatoms selected from the group of O, S, and N, where the carbon of the 4- to 7-membered he Optionally substituted, where any other N of the 4- to 7-membered heterocycloalkyl is an atom Optionally substituted with 1 to 5 substituents independently selected from the group consisting of lower alkyl); H ２ 、 C １ -C ７ aminocarbonyl, C １ -C ４ alkyl (wherein the alkyl is halo Gen, cyano, hydroxyl, ethynyl, oxo, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl Kill) ２ , -SC １ , -C ４ Alkyl, -S(O)C １ , -C ４ Alkyl, -SO ２ C １ , -C ４ alkyl, -C(O)NH-C ３ -C ６ cycloalkyl and -C(O)NH-C １ -C ６ optionally substituted with 1 to 5 substituents independently selected from the group consisting of alkyl) and C ３ -C ６ substituted with 1 to 4 substituents independently selected from the group consisting of cycloalkyl Optionally substituted, where any other N of the 4- to 7-membered heterocycloalkyl is an atom As long as the price allows, hydrogen, -NH ２ , C １ -C ７ aminocarbonyl, -SO ２ C １ -C ４ Al Kill, -SO ２ C １ -C ４ Haloalkyl and C １ -C ４ Alkyl (wherein the alkyl is , halogen, cyano, hydroxyl, ethynyl, C １ -C ４ alkoxy, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S( O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Shi chloroalkyl, -C(O)NH-C １ -C ６ alkyl and -C(O)NH-C １ -C ６ halo Optionally substituted with 1 to 5 substituents independently selected from the group consisting of lower alkyl)); Substituted with a substituent selected from the group consisting of); 5- to 10-membered heteroaryl (where Here, the heteroaryl has 1 or 2 heteroatoms selected from the group of O, S, and N And the carbon of the 5- to 10-membered heteroaryl may be substituted with 1, 2, or 3 substituents independently selected from the group consisting of halogen, cyano, ni Tro, hydroxyl, C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, Hydroxyl, oxo, C １ -C ４ Alkoxy, -NH ２ 、C １ -C ７ Aminocarbonyl , -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ al Kill, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH- C ３ -C ６ cycloalkyl, -C(O)NH-C １ -C ６ alkyl and -C(O)NH- C １ -C ６ substituted with 1 to 5 substituents independently selected from the group consisting of haloalkyl may also be), C ３ -C ６ cycloalkyl, C １ -C ４ haloalkyl, C １ -C ４ alko Xy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl), -N( C １ -C ４ alkyl) ２ and -C(O)NH-C ３ -C ６ selected from the group consisting of cycloalkyl Optionally substituted with 1, 2, or 3 substituents independently selected, where the heteroaryl Any N of the reel, as long as the valence permits, is hydrogen, C １ -C ４ alkyl (wherein the alkyl R is halogen, cyano, hydroxyl, ethynyl, oxo, C ３ -C ６ cycloalkyl Kill, C １ -C ４ Alkoxy, -NH ２ C １ -C ７ Aminocarbonyl, -NH(C １ - C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O) C １ -C ４ alkyl, -SO ２ C １ -C ４ alkyl, -C(O)NH-C ３ -C ６ cyclo Alkyl and -C(O)NH-C １ -C ６ 1 independently selected from the group consisting of alkyl which may be substituted with a substituent of 0 to 5) and C ３ -C ６ selected from the group consisting of cycloalkyl Optionally substituted with a selected substituent, where any S of the heteroaryl is 1 or which may be substituted with two oxygen atoms); phenyl (wherein the phenyl is halogen N, C １ -C ４ 1 to 3 substituents selected from the group consisting of alkyl, cyano and hydroxyl which may be substituted with a substituent); C ３ -C ６ cycloalkyl (wherein the cycloalkyl is halogen, cyano, hydroxyl, oxo, C １ -C ４ alkoxy, C １ -C ４ alkyl kil (wherein the alkyl is 1 to 3 groups selected from the group consisting of halogen and cyano (which may be replaced by), C １ -C ４ haloalkyl, -NH ２ , C １ -C ７ aminocar Bonyl, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ Alkyl, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O) NH-C ３ -C ６ cycloalkyl, -C(O)NH-C １ -C ６ alkyl, -C(O)N H-C １ -C ６ haloalkyl, C ２ -C ６ alkenyl and C ２ -C ６ consisting of alkynyl optionally substituted with 1 to 5 substituents independently selected from the group heterocycloalkyl having 1 or 2 heteroatoms selected from the group consisting of O, S, B and N, wherein the heterocycloalkyl may be benzo-fused, and wherein the carbon of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro from the group consisting of independently selected 1 to 5 substituents); and may be optionally substituted with 1 to 4 substituents independently selected R, hydroxyl, oxo and C １ -C ４ alkyl, where the alkyl is halogen Cyano, hydroxyl, ethynyl, oxo, C １ -C ４ alkoxy, C ３ -C ６ cyclo Lower alkyl, -NH ２ , C １ -C ７ Aminocarbonyl, -NH(C １ -C ４ Alkyl), -N(C １ -C ４ alkyl), ２ -SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl Ru, -SO ２ C １ -C ４ alkyl, -C(O)NH-C ３ -C ６ cycloalkyl, -C( O) NH-C １ -C ６ alkyl and -C(O)NH-C １ -C ６ consisting of the group of haloalkyl from the group consisting of independently selected 1 to 5 substituents); and may be optionally substituted with 1 to 4 substituents independently selected from the group consisting of independently selected 1 to 5 substituents); and may be optionally substituted with 1 to 4 substituents independently selected from the group consisting of independently selected 1 to 5 substituents); and may be optionally substituted with 1 to 4 substituents independently selected from the group consisting of independently selected 1 to 5 substituents); and may be optionally substituted with 1 to 4 substituents independently selected from the group consisting of independently selected 1 to 5 substituents); and may be optionally substituted with 1 to 4 substituents independently selected N is, as far as the valence permits, hydrogen, -NH ２ , C １ -C ７ aminocarbonyl, -SO ２ C １ -C ４ alkyl, -SO ２ C １ -C ４ haloalkyl, -C(O)-NH ２ 、C １ -C ４ a Lukyl (wherein the alkyl is halogen, cyano, hydroxyl, ethynyl, C １ -C ４ alkoxy, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , - SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl, -SO ２ C １ -C ４ alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl and -C(O)NH-C １ -C ６ Haloalkyl optionally substituted with 1 to 5 substituents independently selected from the group consisting of, C ３ - C ６ cycloalkyl, 5- or 6-membered heteroaryl, and phenyl, where the phenyl is Halogen, C １ -C ４ independently selected from the group consisting of alkyl, cyano and hydroxyl from the group consisting of independently selected 1 to 5 substituents); and may be optionally substituted with 1 to 4 substituents independently selected from the group consisting of independently selected 1 to 5 substituents); and may be optionally substituted with 1 to 4 substituents independently selected from the group consisting of independently selected 1 to 5 substituents); and may be optionally substituted with 1 to 4 substituents independently selected from the group consisting of independently selected 1 to 5 substituents); and may be optionally substituted with 1 to 4 substituents independently selected from the group consisting of independently selected 1 to 5 substituents);]; (iii) C ３ - C ６ cycloalkyl [wherein the cycloalkyl is halogen, cyano N, hydroxyl, oxo, carboxy, C １ -C ４ alkoxy, C １ -C ４ alkyl( wherein the alkyl is substituted with 1 to 3 groups selected from the group consisting of halogen and cyano may be), C １ -C ４ haloalkyl, -NH ２ , C １ -C ７ aminocarbonyl , -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ al Kill, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH- C ３ -C ６ cycloalkyl, -C(O)NH-C １ -C ６ alkyl, -C(O)NH-C １ -C ６ haloalkyl, C ２ -C ６ alkenyl (wherein the alkenyl has 1 to 3 halo which may be substituted with a gene) and C ２ -C ６ independently selected from the group consisting of alkynyl optionally substituted with 1 to 5 substituents);]; (iv) 6-membered aryl or 5- to 10-membered heteroaryl [wherein the heteroaryl has 1, 2 or 3 heteroatoms selected from the group consisting of O, S and N, and wherein the carbon of the 6-membered aryl and the 5- to 10-membered heteroaryl may be optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano , nitro, hydroxyl, C １ -C ４ -alkyl (wherein the alkyl is halogen, cyano N, hydroxyl, oxo, C １ -C ４ alkoxy, -NH ２ C １ -C ７ aminocarbo Nil, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ Alkyl, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)N H—C ３ —C ６ cycloalkyl and —C(O)NH—C １ —C ６ selected from the group consisting of alkyl optionally substituted with 1 to 5 independently selected substituents), C ３ -C ６ cycloalkyl Ru, C １ -C ４ Haloalkyl, C １ -C ４ Alkoxy, -NH ２ , -NH(C １ -C ４ A -N(C １ -C ４ alkyl) ２ and -C(O)NH-C ３ -C ６ cycloalkyl from the group consisting of independently selected 1, 2 or 3 substituents); and may be optionally substituted with 1, 2 or 3 substituents independently selected Here, any N of the heteroaryl is, as long as the valence permits, hydrogen and C １ -C ４ alkyl wherein the alkyl is substituted with 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, ethynyl, oxo, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ al -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl and -C(O)NH-C １ -C ６ 1 to 5 substituents independently selected from the group consisting of alkyl optionally substituted with 1, 2 or 3 substituents); and may be optionally substituted with 1, 2 or 3 substituents independently selected ］； (v) 4- to 7-membered heterocycloalkyl [wherein the heterocycloalkyl is O, S and having one or two heteroatoms selected from the group of O, S and N, wherein the heterocyclic alkyl may be benzo-fused, wherein the carbon atoms of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl are halogen , cyano, nitro, hydroxyl, oxo, C １ -C ４ alkoxy, C １ -C ４ alkyl (wherein the alkyl may be halogen, cyano, hydroxyl, ethynyl, oxo, C １ -C ４ alkoxy, C ３ -C ６ cycloalkyl, -NH ２ , C １ -C ７ aminocarbonyl Le, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ a Lukyl, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH -C ３ -C ６ Cycloalkyl, -C(O)NH-C １ -C ６ Alkyl and -C(O)NH -C １ -C ６ substituted with 1 to 5 substituents independently selected from the group consisting of haloalkyl and may be substituted with 1 to 4 substituents independently selected from the group consisting of and may be substituted with 1 to 3 substituents independently selected from the group consisting of Any N of the heterocycloalkyl of the member, as long as the valence permits, is hydrogen, -NH ２ , C １ -C ７ aminocarbonyl, -SO ２ C １ -C ４ alkyl, -SO ２ C １ -C ４ haloalkyl, -SO ２ NH(C １ -C ４ alkyl), -SO ２ N(C １ -C ４ alkyl ２ , -C(O )-NH ２ 、C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, hydroxy Si, ethynyl, oxo, C １ -C ４ alkoxy, C ３ -C ６ cycloalkyl, -N H(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl,[[]] -S(O)C １ -C ４ alkyl, -SO ２ C １ -C ４ alkyl, -C(O)NH-C ３ - C ６ cycloalkyl and -C(O)NH-C １ -C ６ independently from the group consisting of haloalkyl optionally substituted with 1 to 5 substituents selected therefrom), C ３ -C ６ cycloalkyl, 5 ~6-membered heteroaryl and phenyl (wherein said phenyl is halogen, C １ -C ４ A alkyl, cyano and hydroxyl), and may be substituted with substituents selected from the group consisting of (wherein the alkyl may be halogen, cyano, hydroxyl, ethynyl, oxo, C and may be substituted with 1 to 3 substituents independently selected from the group consisting of and any S of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with one or two oxygen atoms]; and, (vi) -NR １２ R １３ ; wherein, R １２ is hydrogen, C １ -C ６ alkyl, C ２ -C ６ alkenyl, C ２ -C ６ alkynyl , C ３ -C ６ Cycloalkyl, C ４ -C ７ Alkylcycloalkyl, C １ -C ７ Alkyl Carbonyl, C １ -C ７ Aminocarbonyl and C ２ -C ５ Composed of alkoxycarbonyl selected from the group; R １３ is hydrogen, C １ -C ６ -alkyl (wherein the alkyl is halogen, cyano, ni Toro, hydroxyl, oxo, C ３ -C ６ Cycloalkyl, C １ -C ４ Alkoxy, -N H ２ 、C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl and -SO ２ C １ -C ４ optionally substituted with 1 to 5 substituents independently selected from the group consisting of alkyl good), C ３ -C ６ cycloalkyl, -C(O)-C １ -C ６ alkyl (wherein this is , halogen, cyano, nitro, hydroxyl, oxo, C ３ -C ６ -cycloalkyl, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ Alkyl and -SO ２ C １ -C ４ 1 to 5 substituents independently selected from the group consisting of alkyl may be substituted with substituents), 4- to 7-membered heterocycloalkyl [wherein the heterocyclic alkyl has one or two heteroatoms selected from the group of O, S and N, and wherein the heterocycloalkyl may be benzo-fused, and wherein the 4- to 7- membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl The carbon of the kill is halogen, cyano, nitro, hydroxyl, oxo, C １ -C ４ alkyl (wherein the alkyl may be halogen, cyano, hydroxyl, ethynyl, oxo, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ al -Kill), -N(C １ -C ４ -Alkyl) ２ , -SC １ -C ４ -Alkyl, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl , -C(O)NH-C １ -C ６ alkyl and -C(O)NH-C １ -C ６ haloalkyl or which may be substituted with 1 to 5 substituents independently selected from the group consisting of) and C ３ -C ６ It may be substituted with 1 to 4 substituents independently selected from the group consisting of cycloalkyl and may be substituted with 1 to 3 substituents independently selected from the group consisting of Any N of the 7-membered heterocycloalkyl, to the extent permitted by its valence, is hydrogen, C １ -C ４ alkyl Ru (wherein the alkyl is halogen, cyano, hydroxyl, ethynyl, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl) , -N(C １ -C ４ alkyl), ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ yl Kill, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl and - C(O)NH-C １ -C ６ substituted with 1 to 5 substituents independently selected from the group consisting of alkyl which may be substituted), C ３ -C ６ cycloalkyl, 5- or 6-membered heteroaryl and f enyl (wherein the phenyl is halogen, C １ -C ４ -alkyl, cyano and hydroxy and may be substituted with substituents selected from the group consisting of and any S of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with one or two oxygen atoms] and 5- to 10-membered heteroaryl [wherein the heteroaryl has one or two heteroatoms selected from the group of O, S and N, and wherein the carbon atoms of the 5- to 10-membered heteroaryl are halogen, cyano, nitro, and may be substituted, and wherein any N of the heteroaryl may, to the extent permitted by its valence, Hydroxyl, C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, hydro Xyl, oxo, C １ -C ４ Alkoxy, -NH ２ , C １ -C ７ Aminocarbonyl, -N H(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl, -SO ２ C １ -C ４ alkyl, -C(O)NH-C ３ - C ６ cycloalkyl and -C(O)NH-C １ -C ６ independently selected from the group consisting of alkyl which may be substituted with 1 to 5 substituents to be selected), C ３ -C ６ cycloalkyl, C １ - C ４ haloalkyl, C １ -C ４ alkoxy, -NH ２ , -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl), ２ -C(O)NH-C ３ -C ６ cycloalkyl and -C( O) NH-C １ -C ６ 1, 2 or 3 substituents independently selected from the group consisting of alkyl and may be substituted with substituents selected from the group consisting of Hydrogen, C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, hydroxyl, Ethynyl, oxo, C １ -C ４ Alkoxy, -NH ２ , C １ -C ７ Aminocarbonyl , -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ al Kill, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH- C ３ -C ６ cycloalkyl and -C(O)NH-C １ -C ６ independently from the group consisting of alkyl which may be substituted with substituents of 1 to 5 selected and C ３ -C ６ cycloalkyl and may be substituted with substituents selected from the group consisting of], and is selected from the group consisting of; or, R １１ R and W, together with the nitrogen to which they are attached, form a group consisting of N, S and O Optionally form a 4- to 7-membered ring which may contain 1 to 2 heteroatoms selected therefrom, wherein The carbon of the ring is cyano, hydroxyl, oxo, halogen, C １ -C ２ alkoxy, N, N - Di - C １ - C ４ - alkylaminocarboxyl, N - C １ - C ４ - alkylaminoca Carboxyl, C １ -C ７ Aminocarboxyl, C １ -C ４ Alkyl (wherein the alkyl is halogen, cyano, hydroxyl, C ３ -C ６ -cycloalkyl, C １ -C ４ -alkoxy Si, -NH ２ C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ and -C(O)NH-C ３ -C ６ selected from the group consisting of cycloalkyl optionally substituted with substituents 1 to 5 which are selected independently and may be the same or different), C ３ -C ６ cycloalkyl (Here, the cycloalkyl is halogen, cyano, hydroxyl and C １ -C ４ alko Optionally substituted with 1 to 3 substituents selected from the group consisting of xy), -C(O)N H-C ３ -C ６ cycloalkyl, -C(O)NH-C １ -C ６ alkyl, -C(O)NH -C １ -C ６ haloalkyl, 5- to 6-membered heteroaryl and phenyl (wherein said pheni R is halogen, C １ -C ４ alkyl, cyano, hydroxyl, C １ -C ２ alkoxy, N,N-di-C １ -C ４ -alkylaminocarboxyl, N-C １ -C ４ -alkylami Nocarboxyl and C １ -C ７ 1 independently selected from the group consisting of aminocarboxyl Optionally substituted with 1 to 4 substituents independently selected from (Optionally substituted with 1 to 3 substituents) may also be, wherein any N of the 4- to 7-membered ring is hydrogen, C １ -C ４ alkyl (this Here, the alkyl is halogen, cyano, hydroxyl, C ３ -C ６ cycloalkyl, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ al -Kill), -N(C １ -C ４ alkyl) ２ and -C(O)NH-C ３ -C ６ cycloalkyl optionally substituted with 1 to 5 substituents independently selected from the group consisting of), C ３ -C ６ Cycloalkyl, where the cycloalkyl is halogen, cyano, hydroxyl, C １ -C ４ alkoxy, -C(O)NH-C ３ -C ６ cycloalkyl and -C(O)NH- C １ -C ６ substituted with 1 to 3 substituents independently selected from the group consisting of alkyl Optionally substituted with a substituent selected from the group consisting of), 5- to 6-membered heteroaryl and phenyl (wherein the phenyl is halogen, C １ -C ４ 1 to 3 independently selected from the group consisting of alkyl, cyano and hydroxyl Optionally substituted with a substituent selected from the group consisting of (Optionally substituted with substituents) Wherein any S of the 4- to 7-membered ring may be substituted with 1 or 2 oxygen atoms ； Y is C １ -C ６ alkyl, where the alkyl is halogen, cyano, hydro Xyl, oxo, C ３ -C ６ Cycloalkyl, C １ -C ４ Alkoxy, ethynyl, - NH ２ 、 C １ - C ７ aminocarbonyl, -NH(C １ - C ４ alkyl), -N(C １ - C ４ alkyl) ２ 、 -SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl, -SO ２ C １ -C ４ alkyl, -SO ２ NH(C １ -C ４ alkyl), -SO ２ N(C １ -C ４ al Kill) ２ , -SO ２ NH(C １ , -C ４ haloalkyl), -C(O)NH-C ３ , -C ６ cyclic Lower alkyl, where this is halogen, hydroxyl, cyano and C １ -C ４ alkyl (Here, the alkyl is halogen, cyano, hydroxyl, C １ -C ４ alkoxy and -NH ２ optionally substituted with 1 to 5 substituents independently selected from the group consisting of) or Optionally substituted with 1 to 3 substituents independently selected from the group consisting of), -C(O) NH-C １ -C ６ alkyl, -C(O)NH-C １ -C ６ cyanoalkyl [wherein this which may be substituted with 1 to 3 halogens], -C(O)NH-C １ -C ６ Halo a Alkyl, phenyl [wherein the phenyl is halogen, cyano, nitro, hydroxyl, C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, hydroxyl, C ３ - C ６ Cycloalkyl, C １ -C ４ Haloalkyl, C １ -C ４ Alkoxy, -NH ２ , -N H(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ and -C(O)NH-C ３ -[[]] C ６ substituted with 1 to 3 substituents independently selected from the group consisting of cycloalkyl may also be) and C ３ -C ６ cycloalkyl (wherein the cycloalkyl is halogen, cyano No., hydroxyl, oxo, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbo Nil, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ Alkyl, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)N H—C ３ —C ６ cycloalkyl, —C(O)NH—C １ —C ６ alkyl, C ２ —C ６ al Kenyl and C ２ -C ６ substituted with 1 to 5 substituents independently selected from the group consisting of alkynyl Optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of (Optionally substituted) Optionally substituted), 5- to 10-membered heteroaryl [wherein the heteroaryl has 1 or 2 heteroatoms selected from the group of O, S And N, wherein the 5- to 10 The carbon of the heteroaryl of the member is halogen, cyano, nitro, hydroxyl, C １ -C ４ A Lukyl (wherein the alkyl is halogen, cyano, hydroxyl, oxo, C １ -C ４ Alkoxy, -NH ２ , C １ -C ７ Aminocarbonyl, -NH(C １ -C ４ Alkyl), -N(C １ -C ４ alkyl), ２ -SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl Ru, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl and -C (O)NH-C １ -C ６ Substituted with 1 to 5 substituents independently selected from the group consisting of alkyl (which may be replaced), C ３ - C ６ cycloalkyl, C １ - C ４ haloalkyl, C １ - C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl) , -N(C １ -C ４ alkyl) ２ , -C(O)NH-C ３ -C ６ cycloalkyl and -C (O)NH-C １ -C ６ 1, 2 or 3 substitutions independently selected from the group consisting of alkyl Optionally substituted with a group, wherein any N of the heteroaryl, as far as the valence permits , hydrogen, C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, hydroxyl , ethynyl, oxo, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl Le, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ a Lukyl, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH -C ３ -C ６ cycloalkyl and -C(O)NH-C １ -C ６ selected from the group consisting of alkyl which may be substituted with substituents 1 to 5 which are independently selected) and C ３ -C ６ cycloalkyl Optionally substituted with a substituent selected from the group consisting of] and 4- to 7-membered heterocycloalkyl Alkyl [wherein the heterocycloalkyl has 1 or 2 heteroatoms selected from the group of O, S and N And has, wherein the heterocycloalkyl may be benzo-fused Wherein the carbon of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4 To 7-membered heterocycloalkyl may be halogen, cyano, nitro, hydroxyl, o Quinone, C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, hydroxyl, Ethynyl, oxo, C １ -C ４ Alkoxy, -NH ２ , C １ -C ７ Aminocarbonyl , -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alk Kill, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH- C ３ -C ６ cycloalkyl and -C(O)NH-C １ -C ６ independently selected from the group consisting of alkyl which may be substituted with substituents of 1 to 5 selected and C ３ -C ６ cycloalkyl Optionally substituted with 1 to 4 substituents independently selected from the group consisting of, wherein the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocyclic Any N of lower alkyl is, as long as the valence permits, hydrogen, C １ -C ４ alkyl (wherein the a Lukir is halogen, cyano, hydroxyl, ethynyl, C １ -C ４ alkoxy, - NH ２ 、 C １ - C ７ aminocarbonyl, -NH(C １ - C ４ alkyl), -N(C １ - C ４ alkyl) ２ 、 - SC １ - C ４ alkyl, - S(O)C １ - C ４ alkyl, - SO ２ C １ -C ４ alkyl, -C(O)NH-C ３ -C ６ cycloalkyl and -C(O)NH-C １ -C ６ optionally substituted with 1 to 5 substituents independently selected from the group consisting of alkyl Good), C ３ -C ６ Selected from the group consisting of cycloalkyl and 5- to 6-membered heteroaryl Optionally substituted with a substituent to be substituted, wherein the 4- to 7-membered heterocycloalkyl or optionally The optionally benzo-fused 4- to 7-membered heterocycloalkyl, any S of which may be substituted with 1 or 2 oxygen Optionally substituted with 1 to 5 substituents independently selected from the group consisting of] atoms Optionally substituted) A compound represented by or a salt thereof. Claim 2 W is selected from the group consisting of: (i) hydrogen, (ii) C １ -C ６ alkyl [wherein the alkyl is halogen; cyano ； Hydroxy Ru; oxo; C １ -C ４ alkoxy; C ３ -C ６ cycloalkyl (wherein the cycloal The alkyl is substituted with 1 to 3 substituents independently selected from the group consisting of halogen and cyano may also be); ethynyl; -NH ２ ; C １ -C ７ aminocarbonyl; -NH(C １ -C ４ alkyl); -N(C １ -C ４ alkyl) ２ ; -SC １ -C ４ alkyl; -S(O)C １ -C ４ alkyl; -SO ２ C １ -C ４ alkyl; -C(O)NH-C ３ -C ６ cyclo a Lukyl (where this is halogen, hydroxyl, cyano and C １ -C ４ alkyl (this Here, the alkyl is halogen, cyano, hydroxyl, C １ -C ４ alkoxy, C ３ - C ６ cycloalkyl and -NH ２ substituted with 1 to 5 substituents independently selected from the group consisting of Optionally substituted with 1 to 3 substituents independently selected from the group consisting of (Optionally substituted) may also be); -C(O)NH-C １ -C ６ alkyl (wherein this is halogen, cyano , hydroxyl, C １ -C ４ alkoxy, C ３ -C ６ cycloalkyl and -NH ２ consisting of optionally substituted with 1 to 5 substituents independently selected from the group consisting of); -C(O)NH -C １ -C ６ cyanoalkyl (wherein this may be substituted with 1 to 3 halogens) i); -C(O)NH-C １ -C ６ haloalkyl; -C(O)- a 4- to 7-membered heterocycle alkyl (wherein this is attached by nitrogen and may have one or two other heteroatoms selected from the group consisting of O, S, and N, where the carbon of the 4- to 7-membered hetero cycloalkyl may be substituted with a substituent selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, -N and may be substituted, where any other N of the 4- to 7-membered heterocycloalkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of H ２ 、 C １ -C ７ aminocarbonyl, C １ -C ４ alkyl (wherein the alkyl is halo Gen, cyano, hydroxyl, ethynyl, oxo, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl Kill) ２ , -SC １ , -C ４ Alkyl, -S(O)C １ , -C ４ Alkyl, -SO ２ C １ , -C ４ alkyl, -C(O)NH-C ３ -C ６ cycloalkyl and -C(O)NH-C １ -C ６ optionally substituted with 1 to 5 substituents independently selected from the group consisting of alkyl) and C ３ -C ６ substituted with 1 to 4 substituents independently selected from the group consisting of cycloalkyl lower alkyl); 5- to 10-membered heteroaryl (wherein the heteroaryl has one or two heteroatoms selected from the group consisting of O, S, and N, where the carbon of the 5- to 10-membered hetero As long as the price allows, hydrogen, -NH ２ , C １ -C ７ aminocarbonyl, -SO ２ C １ -C ４ al Kill, -SO ２ C １ -C ４ Haloalkyl and C １ -C ４ Alkyl (wherein the alkyl is , halogen, cyano, hydroxyl, ethynyl, C １ -C ４ alkoxy, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S( O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Shi chloroalkyl, -C(O)NH-C １ -C ６ alkyl and -C(O)NH-C １ -C ６ ha aryl may be substituted with a substituent selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, -N and may be substituted with 1, 2, or 3 substituents independently selected, where any S of the heteroaryl may be substituted with one or two oxygen atoms); phenyl (wherein the phenyl may be substituted with a substituent selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, -N and may be substituted with 1 to 5 substituents independently selected, where any S of the heteroaryl may be substituted with one or Toro, hydroxyl, C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, Hydroxyl, oxo, C １ -C ４ Alkoxy, -NH ２ , C １ -C ７ Aminocarbonyl , -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl ２ , -SC １ -C ４ al Kill, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH- C ３ -C ６ cycloalkyl, -C(O)NH-C １ -C ６ alkyl and -C(O)NH- C １ -C ６ substituted with 1 to 5 substituents independently selected from the group consisting of haloalkyl may also be), C ３ -C ６ cycloalkyl, C １ -C ４ haloalkyl, C １ -C ４ alko Xy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl), -N( C １ -C ４ alkyl) ２ and -C(O)NH-C ３ -C ６ selected from the group consisting of cycloalkyl two oxygen atoms); phenyl (wherein the phenyl may be substituted with a substituent selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, -N Any N of the reel is, as long as the valence permits, hydrogen, C １ -C ４ alkyl (wherein the alkyl R is halogen, cyano, hydroxyl, ethynyl, oxo, C ３ -C ６ cycloalkyl Kill, C １ -C ４ Alkoxy, -NH ２ , C １ -C ７ Aminocarbonyl, -NH(C １ - C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O) C １ -C ４ alkyl, -SO ２ C １ -C ４ alkyl, -C(O)NH-C ３ -C ６ cyclo Alkyl and -C(O)NH-C １ -C ６ independently selected from the group consisting of alkyl 1 which may be substituted with a substituent of 0 to 5) and C ３ -C ６ selected from the group consisting of cycloalkyl and may be substituted with 1 to 5 substituents independently selected, where any S of the heteroaryl may be substituted with one or two oxygen atoms); phenyl (wherein the phenyl may be substituted with a substituent selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, -N N, C １ -C ４ 1 to 3 substituents selected from the group consisting of alkyl, cyano and hydroxyl which may be substituted with a substituent); C ３ -C ６ cycloalkyl (wherein the cycloalkyl is halogen, cyano, hydroxyl, oxo, C １ -C ４ alkoxy, C １ -C ４ alkyl alkyl (wherein the alkyl may be substituted with 1 to 3 groups selected from the group consisting of halogen and cyano); and 4- to 7-membered may be replaced by), C １ -C ４ haloalkyl, -NH ２ , C １ -C ７ aminocar Bonyl, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ Alkyl, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O) NH-C ３ -C ６ cycloalkyl, -C(O)NH-C １ -C ６ alkyl, -C(O)N H-C １ -C ６ haloalkyl, C ２ -C ６ alkenyl and C ２ -C ６ consisting of alkynyl heterocycloalkyl (wherein the heterocycloalkyl has one or two heteroatoms selected from the group consisting of O, S, B, and N, where the heterocycloalkyl may be benzo-fused, where the carbon of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with a substituent selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, -N and may be substituted with 1 to 5 substituents independently selected, where any B of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl is substituted with hydroxyl to the extent permitted by its valence, where any N of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of lower alkyl); and may be substituted with 1 to 4 substituents independently selected from the group consisting of, where any B of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl is substituted with hydroxyl to the extent permitted by its valence, where any R, hydroxyl, oxo and C １ -C ４ alkyl (wherein the alkyl is halogen,[[]] Cyano, hydroxyl, ethynyl, oxo, C １ -C ４ Alkoxy, C ３ -C ６ Cyclo Lower alkyl, -NH ２ , C １ -C ７ Aminocarbonyl, -NH(C １ -C ４ Alkyl), -N(C １ -C ４ alkyl), ２ -SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl Ru, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl, -C( O) NH-C １ -C ６ alkyl and -C(O)NH-C １ -C ６ consisting of the group of haloalkyl N of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of lower alkyl); and may be substituted with 1 to 4 substituents independently selected from the group consisting of, where any B of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl is substituted with hydroxyl to the extent permitted by its valence, where any N of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with 1 to 5 substituents independently selected from the group consisting of lower alkyl); and may be substituted with 1 to 3 substituents selected from the group consisting of and may be substituted with 1 to 3 substituents selected from the group consisting of and may be substituted with 1 to 3 substituents selected from the group consisting of lower alkyl); and may be substituted with 1 to 3 substituents selected from the group consisting of and may be substituted with 1 to 3 substituents selected from the group consisting of and may be substituted with 1 to 3 substituents selected from the group consisting of N is, to the extent permitted by its valence, hydrogen, -NH ２ , C １ -C ７ aminocarbonyl, -SO ２ C １ -C ４ alkyl, -SO ２ C １ -C ４ haloalkyl, -C(O)-NH ２ 、C １ -C ４ a Lukyl (wherein the alkyl is halogen, cyano, hydroxyl, ethynyl, C １ -C ４ alkoxy, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , - SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl, -SO ２ C １ -C ４ alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl and -C(O)NH-C １ -C ６ Haloalkyl (which may be substituted with 1 to 5 substituents independently selected from the group consisting of ル), C ３ - C ６ cycloalkyl, 5- or 6-membered heteroaryl, and phenyl (wherein said phenyl is Halogen, C １ -C ４ independently selected from the group consisting of alkyl, cyano and hydroxyl lower alkyl); and may be substituted with a substituent selected from the group consisting of and may be substituted with a substituent selected from the group consisting of and may be substituted with a substituent selected from the group consisting of lower alkyl); and may be substituted with a substituent selected from the group consisting of and may be substituted with a substituent selected from the group consisting of and may be substituted with a substituent selected from the group consisting of Any S of the 4- to 7-membered heterocycloalkyl may be substituted with one or two oxygen atoms); 1 to 5 substituents independently selected from the group consisting of may be substituted]; (iii) C ３ -C ６ -cycloalkyl [wherein the cycloalkyl is halogen, cyano N, hydroxyl, oxo, carboxy, C １ -C ４ alkoxy, C １ -C ４ alkyl( wherein the alkyl is substituted with 1 to 3 groups selected from the group consisting of halogen and cyano (which may be), C １ - C ４ haloalkyl, -NH ２ , C １ - C ７ aminocarbonyl , -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl Kill, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH- C ３ -C ６ cycloalkyl, -C(O)NH-C １ -C ６ alkyl, -C(O)NH-C １ -C ６ haloalkyl, C ２ -C ６ alkenyl (wherein the alkenyl has 1 to 3 halo which may be substituted with a gene) and C ２ -C ６ independently selected from the group consisting of alkynyl may be substituted with 1 to 5 substituents]; (iv) 5- to 10-membered heteroaryl [wherein the heteroaryl has one or two heteroatoms selected from the group of O, S, and N, and wherein the 5- to 10-membered hete may be substituted with 3 substituents, and wherein any N of the heteroaryl has a valence of The carbon of the lower real is halogen, cyano, nitro, hydroxyl, C １ -C ４ alkyl ( Here, the alkyl is halogen, cyano, hydroxyl, oxo, C １ -C ４ alkoxy Si, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl, -S O ２ C １ -C ４ alkyl, -C(O)NH-C ３ -C ６ cycloalkyl and -C(O)N H—C １ —C ６ substituted with 1 to 5 substituents independently selected from the group consisting of alkyl may also be), C ３ -C ６ cycloalkyl, C １ -C ４ haloalkyl, C １ -C ４ alko Xy, -NH ２ , -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ and - C(O)NH-C ３ -C ６ independently selected from the group consisting of cycloalkyl, 1, 2 or may be substituted with 1 to 5 substituents independently selected from the group consisting of As long as permitted, hydrogen and C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, hi Droxyl, ethynyl, oxo, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ ami N-carbonyl, -NH(C １ -C ４ -alkyl), -N(C １ -C ４ -alkyl) ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl, -SO ２ C １ -C ４ alkyl, -C (O)NH-C ３ -C ６ cycloalkyl and -C(O)NH-C １ -C ６ consisting of alkyl may be substituted); selected from the group consisting of may be substituted]; (v) 4- to 7-membered heterocycloalkyl [wherein the heterocycloalkyl has one or two heteroatoms selected from the group of O, S, and N, and wherein the heterocyclo may be optionally benzo-fused, and wherein the carbon of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl is halogen may be substituted with 1 to 5 substituents independently selected from the group consisting of may be substituted with 1 to 4 substituents independently selected from the group consisting of, and wherein the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl , cyano, nitro, hydroxyl, oxo, C １ -C ４ -alkyl (wherein the alkyl is , halogen, cyano, hydroxyl, ethynyl, oxo, C １ -C ４ alkoxy, C ３ -C ６ cycloalkyl, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ -N(alkyl), -C １ -C ４ (alkyl) ２ , -SC １ -C ４ (alkyl), -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl Kill, -C(O)NH-C １ -C ６ Alkyl and -C(O)NH-C １ -C ６ Haloalkyl may be substituted with 1 to 3 substituents independently selected from the group consisting of hydroxyl and alkoxyl); or may be substituted with 1 to 4 substituents independently selected from the group consisting of, and wherein any S of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with one or two oxygen atoms]; Any N of the loop, as long as the valence permits, is hydrogen, -NH ２ , C １ -C ７ aminocarbonyl, - SO ２ C １ -C ４ alkyl, -SO ２ C １ -C ４ haloalkyl, -C(O)-NH ２ 、C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, hydroxyl, acetylene Nil, C １ -C ４ Alkoxy, C ３ -C ６ Cycloalkyl, -NH(C １ -C ４ Alkyl ), -N(C １ -C ４ alkyl), ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ a Lukil, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl and -C(O)NH-C １ -C ６ 1 to 5 substituents independently selected from the group consisting of haloalkyl which may be substituted with a substituent), C ３ -C ６ cycloalkyl, 5- to 6-membered heteroaryl and phenyl, where the phenyl is halogen, C １ -C ４ alkyl, cyano and hyd and, wherein selected from the group; may be substituted), 4- to 7-membered heterocycloalkyl [wherein the heterocyclo alkyl has one or two heteroatoms selected from the group of O, S, and N, and (vi) -NR １２ R １３ ; wherein the heterocycloalkyl may be benzo-fused, and wherein the 4- to 7 R １２ is hydrogen, C １ -C ６ alkyl, C ２ -C ６ alkenyl, C ２ -C ６ alkynyl , C ３ -C ６ Cycloalkyl, C ４ -C ７ Alkylcycloalkyl, C １ -C ７ Alkyl Carbonyl, C １ -C ７ Aminocarbonyl and C ２ -C ５ Consisting of alkoxycarbonyl membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl R １３ is hydrogen, C １ -C ６ -alkyl (wherein the alkyl is halogen, cyano, ni Toro, hydroxyl, oxo, C ３ -C ６ Cycloalkyl, C １ -C ４ Alkoxy, -N H ２ 、C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl and -SO ２ C １ -C ４ optionally substituted with 1 to 5 substituents independently selected from the group consisting of alkyl good), C ３ -C ６ cycloalkyl, -C(O)-C １ -C ６ alkyl (wherein this is , halogen, cyano, nitro, hydroxyl, oxo, C ３ -C ６ -cycloalkyl, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ Alkyl and -SO ２ C １ -C ４ 1 to 5 substituents independently selected from the group consisting of alkyl (wherein the alkyl is halogen, cyano, hydroxyl, ethynyl, oxo, C ​ ​ ​ The carbon of the kill is halogen, cyano, nitro, hydroxyl, oxo, C １ -C ４ alkyl ​ １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ al -Kill), -N(C １ -C ４ -Alkyl ２ , -SC １ -C ４ -Alkyl, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl , -C(O)NH-C １ -C ６ alkyl and -C(O)NH-C １ -C ６ haloalkyl or optionally substituted with 1 to 5 substituents independently selected from the group consisting of) and C ３ -C ６ even if it is substituted with 1 to 4 substituents independently selected from the group consisting of cycloalkyl Well, here, the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- Any N of the 7-membered heterocycloalkyl, to the extent permitted by its valence, is hydrogen, C １ -C ４ alkyl Ru (wherein the alkyl is halogen, cyano, hydroxyl, ethynyl, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl) , -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ yl Kill, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl and - C(O)NH-C １ -C ６ substituted with 1 to 5 substituents independently selected from the group consisting of alkyl which may be replaced), C ３ -C ６ cycloalkyl, 5- to 6-membered heteroaryl and f phenyl (wherein the phenyl is halogen, C １ -C ４ -alkyl, cyano and hydroxy which may be substituted with 1 to 3 substituents independently selected from the group consisting of substituted with a substituent selected from the group consisting of, wherein any S of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with 1 or 2 oxygen atoms]; and 5- to 10-membered heteroaryl [wherein the heteroaryl has 1 or 2 heteroatoms selected from the group consisting of O, S, and N, wherein the carbon of the 5- to 10-membered heteroaryl is halogen, cyano, nitro, Hydroxyl, C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, hydro Xyl, oxo, C １ -C ４ Alkoxy, -NH ２ C １ -C ７ Aminocarbonyl, -N H(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl, -SO ２ C １ -C ４ alkyl, -C(O)NH-C ３ - C ６ cycloalkyl and -C(O)NH-C １ -C ６ independently selected from the group consisting of alkyl optionally substituted with 1 to 5 substituents selected), C ３ -C ６ cycloalkyl, C １ - C ４ haloalkyl, C １ -C ４ alkoxy, -NH ２ -, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl), ２ -C(O)NH-C ３ -C ６ cycloalkyl and -C( O) NH-C １ -C ６ One, two or three substituents independently selected from the group consisting of alkyl may be substituted, wherein any N of the heteroaryl, to the extent permitted by valence, Hydrogen, C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, hydroxyl, Ethynyl, oxo, C １ -C ４ Alkoxy, -NH ２ , C １ -C ７ Aminocarbonyl , -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ al Kill, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH- C ３ -C ６ cycloalkyl and -C(O)NH-C １ -C ６ independently from the group consisting of alkyl which may be substituted with substituents of 1 to 5 selected and C ３ -C ６ cycloalkyl may be substituted with a substituent selected from the group consisting of]; selected from the group consisting of or, R １１ R and W, together with the nitrogen to which they are attached, form a group consisting of N, S and O optionally form a 4- to 7-membered ring containing 1 to 2 heteroatoms selected therefrom, wherein The carbon of the ring is cyano, hydroxyl, oxo, halogen, C １ -C ２ alkoxy, N, N - Di - C １ - C ４ - alkylaminocarboxyl, N - C １ - C ４ - alkylamino ca Carboxyl, C １ -C ７ Aminocarboxyl, C １ -C ４ Alkyl (wherein the alkyl is halogen, cyano, hydroxyl, C ３ -C ６ -cycloalkyl, C １ -C ４ -alkoxy Si, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ and -C(O)NH-C ３ -C ６ selected from the group consisting of cycloalkyl optionally substituted with 1 to 5 substituents independently selected, C ３ -C ６ cycloalkyl (Here, the cycloalkyl is halogen, cyano, hydroxyl and C １ -C ４ alko which may be substituted with 1 to 3 substituents selected from the group consisting of), -C(O)N H-C ３ -C ６ cycloalkyl, -C(O)NH-C １ -C ６ alkyl, -C(O)NH -C １ -C ６ haloalkyl, 5- to 6-membered heteroaryl and phenyl (wherein said pheni R is halogen, C １ -C ４ -alkyl, cyano, hydroxyl, C １ -C ２ -alkoxy, N,N-di-C １ -C ４ -alkylaminocarboxyl, N-C １ -C ４ -alkylami Selected independently from the group consisting of non-carboxyl and C １ -C ７ 1 selected independently from the group consisting of aminocarboxyl which may be substituted with 1 to 4 substituents independently selected from the group consisting of which may be substituted with 1 to 3 substituents may also be, and here, any N of the 4- to 7-membered ring is hydrogen, C １ -C ４ alkyl (this Here, the alkyl is halogen, cyano, hydroxyl, C ３ -C ６ cycloalkyl, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ al -Kill), -N(C １ -C ４ -Alkyl ２ and -C(O)NH-C ３ -C ６ -Cycloalkyl optionally substituted with 1 to 5 substituents independently selected from the group consisting of), C ３ -C ６ Cycloalkyl, where the cycloalkyl is halogen, cyano, hydroxyl, C １ -C ４ alkoxy, -C(O)NH-C ３ -C ６ cycloalkyl and -C(O)NH- C １ -C ６ substituted with 1 to 3 substituents independently selected from the group consisting of alkyl ), 5- to 6-membered heteroaryl and phenyl (wherein the phenyl is halogen, C １ -C ４ 1 to 3 independently selected from the group consisting of alkyl, cyano and hydroxyl which may be substituted with a substituent selected from the group consisting of), wherein any S of the 4- to 7-membered ring may be substituted with 1 or 2 oxygen atoms ； Y is C １ -C ６ alkyl, where the alkyl is halogen, cyano, hydro Xyl, oxo, C ３ -C ６ Cycloalkyl, C １ -C ４ Alkoxy, ethynyl, - NH ２ 、 C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ 、-SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl, -SO ２ C １ -C ４ alkyl, -C(O)NH-C ３ -C ６ cycloalkyl [wherein this is halo Gen, hydroxyl, cyano and C １ -C ４ alkyl (wherein the alkyl is halogen , cyano, hydroxyl, C １ -C ４ alkoxy and -NH ２ independently selected from the group consisting of which may be substituted with 1 to 5 substituents selected therefrom); independently selected from the group consisting of 1 which may be substituted with a substituent of 0 to 3], -C(O)NH-C １ -C ６ alkyl, -C( O) NH-C １ -C ６ cyanoalkyl [wherein this is substituted with 1 to 3 halogens may also be —C(O)NH—C １ —C ６ haloalkyl, phenyl [wherein the phenyl Nil is halogen, cyano, nitro, hydroxyl, C １ -C ４ alkyl (wherein the a Lukir is halogen, cyano, hydroxyl, C ３ -C ６ cycloalkyl, C １ -C ４ ha Lower alkyl, C １ -C ４ Alkoxy, -NH ２ , -NH(C １ -C ４ Alkyl), -N( C １ -C ４ alkyl) ２ and -C(O)NH-C ３ -C ６ selected from the group consisting of cycloalkyl optionally substituted with 1 to 3 independently selected substituents) and C ３ -C ６ cycloal Kill (wherein the cycloalkyl is halogen, cyano, hydroxyl, oxo, C １ - C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl ), -N(C １ -C ４ alkyl), ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ a Lukyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl, - C(O)NH-C １ -C ６ alkyl, C ２ -C ６ alkenyl and C ２ -C ６ alkynyl or which may be substituted with 1 to 5 substituents independently selected from the group consisting of); from the group consisting of which may be substituted with 1, 2 or 3 substituents independently selected therefrom]; 5- to 10-membered he teroaryl [wherein the heteroaryl has 1 or 2 heteroatoms selected from the group consisting of O, S, and N, Gen, cyano, nitro, hydroxyl, C １ -C ４ alkyl (wherein the alkyl is ha Halogen, cyano, hydroxyl, oxo, C １ -C ４ alkoxy, -NH ２ C １ -C ７ Aminocarbonyl, -NH(C １ -C ４ -alkyl), -N(C １ -C ４ -alkyl) ２ 、- SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl, -SO ２ C １ -C ４ alkyl, -C(O)NH-C ３ -C ６ cycloalkyl and -C(O)NH-C １ -C ６ alkyl or optionally substituted with 1 to 5 substituents independently selected from the group consisting of), C ３ -C ６ Cycloalkyl, C １ -C ４ Haloalkyl, C １ -C ４ Alkoxy, -NH ２ 、C １ -C ７ aminocarbonyl, -NH(C １ -C ４ -alkyl), -N(C １ -C ４ -alkyl) ２ , -C(O)NH-C ３ -C ６ Cycloalkyl and -C(O)NH-C １ -C ６ Alkyl or wherein the carbon of the 5- to 10-membered heteroaryl may be substituted with 1, 2 or 3 substituents independently selected from the group consisting of, wherein , any N of the heteroaryl, as long as the valence permits, is hydrogen, C １ -C ４ alkyl (where wherein the alkyl is halogen, cyano, hydroxyl, acetylenyl, oxo, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl) , -N(C １ -C ４ alkyl), ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ yl Kill, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl and - C(O)NH-C １ -C ６ substituted with 1 to 5 substituents independently selected from the group consisting of alkyl which may be substituted) and C ３ -C ６ a substituent selected from the group consisting of cycloalkyl substituted]; and 4- to 7-membered heterocycloalkyl [wherein the heterocycloalkyl has 1 or 2 heteroatoms selected from the group consisting of O, S, and N, wherein the heterocycloalkyl may be benzo-fused, wherein the 4- to 7-membered hete Optionally substituted with 1 to 4 substituents on the carbon of a bicycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl, where any N of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl is substituted with a substituent selected from the group consisting of a 5- to 6-membered heteroaryl, and where any S of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with one or two oxygen atoms; The moiety is halogen, cyano, nitro, hydroxyl, oxo, C １ -C ４ alkyl (wherein , the alkyl is halogen, cyano, hydroxyl, ethynyl, oxo, C １ -C ４ alkoxy, -NH ２ , C １ -C ７ aminocarbonyl, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ alkyl, -S(O)C １ -C ４ alkyl Ru, -SO ２ C １ -C ４ Alkyl, -C(O)NH-C ３ -C ６ Cycloalkyl and -C (O)NH-C １ -C ６ substituted with 1 to 5 substituents independently selected from the group consisting of alkyl which may be replaced) and C ３ -C ６ independently selected from the group consisting of cycloalkyl Optionally substituted with 1 to 4 substituents, where any N of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl is substituted with a substituent selected from the group consisting of a 5- to 6-membered heteroaryl, and where any S of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with one or two oxygen atoms; Optionally benzo-fused 4- to 7-membered heterocycloalkyl, where any N of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl is substituted with a substituent selected from the group consisting of a 5- to 6-membered heteroaryl, and where any S of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with one or two oxygen atoms; As long as permitted, hydrogen, C １ -C ４ alkyl (wherein the alkyl is halogen, cyano, hyd Roxyl, ethynyl, C １ -C ４ Alkoxy, -NH ２ C １ -C ７ Aminocarbonyl Le, -NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -SC １ -C ４ a Lukir, -S(O)C １ -C ４ Alkyl, -SO ２ C １ -C ４ Alkyl, -C(O)NH -C ３ -C ６ Cycloalkyl and -C(O)NH-C １ -C ６ Selected from the group consisting of alkyl optionally substituted with 1 to 5 substituents independently selected, C ３ -C ６ cycloalkyl Substituted with a substituent selected from the group consisting of a 5- to 6-membered heteroaryl, where any N of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl is substituted with a substituent selected from the group consisting of a 5- to 6-membered heteroaryl, and where any S of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with one or two oxygen atoms; Optionally benzo-fused 4- to 7-membered heterocycloalkyl, where any N of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl is substituted with a substituent selected from the group consisting of a 5- to 6-membered heteroaryl, and where any S of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with one or two oxygen atoms; Optionally benzo-fused 4- to 7-membered heterocycloalkyl, where any S of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 7-membered heterocycloalkyl may be substituted with one or two oxygen atoms; Optionally substituted with 1 to 5 substituents independently selected from the group consisting of: The compound according to claim 1 or a salt thereof. Claim 3 A １ is trifluoromethyl, and A ２ is O, R １ is hydrogen, and R ２ is trifluoromethyl, and R ３ is hydrogen, and R ４ is trifluoromethyl or a halogen, and, R ５The compound according to claim 1, wherein R is halogen; or a salt thereof 。

4. R ４ is halogen, the compound according to claim 3; or a salt thereof.

5. R ４ is trifluoromethyl, the compound according to claim 3; or a salt thereof.

6. R ４ is chloro or bromo, the compound according to claim 4; or a salt thereof.

7. R ４ is bromo, the compound according to claim 4; or a salt thereof.

8. R ４ is chloro, the compound according to claim 4; or a salt thereof.

9. R ５ is fluoro, the compound according to any one of claims 1 to 8; or a salt thereof.

10. The following 【Table 1】 The compound according to claim 1, selected from the group consisting of; or a salt of any of the above 。

11. A composition comprising the compound according to claim 1 or 2 or a salt thereof and at least one acceptable carrier.

12. Use of the compound according to claim 1 or 2 or a salt thereof as a medicament.

13. Use of the compound according to claim 1 or 2 or a salt thereof in the manufacture of a medicament for treating pests.

14. Use of the compound according to claim 1 or 2 or a salt thereof in the manufacture of a medicament for treating lice.

15. Use of the compound according to claim 1 or 2 or a salt thereof in the manufacture of a medicament for controlling Madani.

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