(AZA)INDOL- Y BENZOFURAN-3-SULFANOAMIDAS

Abstract

Claim 1: A compound characterized in that it has the formula (1), wherein X¹ is N or C(R⁷); X² is NH, S or O; X³ is N or C(R¹²); R² is selected from hydrogen, fluorine, chlorine, bromine, iodine and methoxy; R⁴ is selected from hydrogen, methoxy and halogen; R⁵ is selected from hydrogen, halogen, cyano, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₃ alkylcarbonyl, C₁₋₃ alkoxycarbonyl, C₁₋₃ alkylsulfinyl, and C₁₋₃ alkylsulfonyl, wherein each alkyl or alkoxy can be optionally substituted or more times selected from halogen, C₁₋₃ alkoxy, C₂₋₃ alkynyl, C₂₋₃ alkenyl, cyano, azido, hydroxyl, and C₁₋₃ alkylaminocarbonyl, or R⁵ forms a ring together with R⁶ as described herein; R⁶ is selected from hydrogen, hydroxy, halogen, cyano, azido, nitro, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₁₋₆ alkoxy, C₃₋₇ cycloalkyl, C₃₋₆ cycloalkenyl, C₃₋₇ heterocycloalkyl, C₃₋₇ heterocycloalkenyl, phenyl, C₅₋₁₀ heteroaryl, C₈₋₁₀ heterocyclyl, -ORˣ, -SRˣ, -SORˣ, SO₂Rˣ,-pentafluorosulfanyl, NRʸRᶻᶻ, -NRʸCORˣ, -NRʸCO₂Rˣ, -NRˣCONRʸRᶻ, -NRʸSORˣ, -NRʸSO₂Rˣ, -CORˣ, -CO₂Rˣ, -CONRʸRᶻ, wherein each alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, heterocycloalkyl, cycloalkenyl, phenyl, heteroaryl or heterocyclyl group at R⁶ may be unsubstituted or substituted with one or more substituents selected from halogen, hydroxy, oxo, cyano, azido, nitro, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₃ alkyl, cycloalkyl C₃₋₇, C₃₋₇ heterocycloalkyl, phenyl, C₅₋₁₀ heteroaryl, ORˣ, -SRˣ, -SORˣ, SO₂Rˣ, -pentafluorosulfanyl, NRʸRᶻ, -NRʸCORˣ, -NRʸCO₂Rˣ, -CORˣ, -CO₂Rˣ, -CONRʸRᶻ, wherein Rˣ, Rʸ, Rᶻ and Rᶻᶻ are independently selected from hydrogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₃₋₇ cycloalkyl, C₃₋₆ cycloalkenyl, C₃₋₇ cycloalkyl C₁₋₆, phenyl, C₁₋₆ phenylalkyl, C₃₋₇ heterocycloalkyl, C₃₋₇ heterocycloalkyl, C₁₋₆ alkyl, C₅₋₆ heteroaryl or C₁₋₆ heteroarylalkyl,any of which groups may be unsubstituted or substituted with one or more substituents, selected from those described above, or Rʸ and Rᶻ, or Rʸ and Rᶻᶻ together with the amino atom to which they are both attached may form an aromatic or non-aromatic, unsubstituted or substituted C₅₋₆ heterocycle, wherein Rᶻᶻ is other than hydrogen, or (i) R⁶ forms together with R⁷ and the carbon atoms to which they are attached a 5- or 6-membered aromatic or non-aromatic ring that may optionally contain one or more heteroatoms selected from S, O, and N, and wherein said ring may be unsubstituted or substituted with one or more substituents selected from halogen, hydroxy, cyano, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl C₃₋₇, cycloalkyl C₃₋₇C₁₋₃, heterocycloalkyl C₃₋₇C₁₋₃, and alkoxy C₁₋₆, wherein each alkyl or alkoxy can be unsubstituted or substituted with one or more halogen substituents selected,(ii) R⁶ forms together with R⁵ and the carbon atoms to which R⁶ and R⁵ are attached, a 1,3-dioxolane that may be unsubstituted or substituted with one or two substituents selected from fluoro and methyl, or hydroxy, cyano, C₁₋₆ haloalkoxy preferably C₁₋₃ fluoroalkoxy and C₁₋₆ alkoxy; R⁷ is selected from hydrogen, halogen, cyano, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₂₋₆ alkynyl, C₂₋₆ alkenyl, C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylthio, C₃₋₇ cycloalkyl, C₃₋₇ cycloalkyl, C₃₋₇ cycloalkyloxy, C₃₋₄ heterocycloalkyl, C₃₋₇ heterocycloalkyloxy, phenyl, phenyloxy, phenylsulfonyl, phenylsulfinyl, C₅₋₆ heteroaryl, C₅₋₆ heteroaryloxy, C₅₋₆ heteroaryl C₁₋₃ alkyl, C₅₋₆ heteroaryl C₁₋₃ alkoxy, C₃₋₆ cycloalkyl C₁₋₂ alkyl, C₃₋₆ cycloalkyl C₁₋₃ alkoxy, C₃₋₆ heterocycloalkyloxy, C₃₋₆ heterocycloalkyl C₁₋₂ alkyl, C₁₋₂ heterocycloalkyl-alkyloxy, C₁₋₂ phenylalkyl, C₁₋₂ phenylalkoxy,wherein each group in R⁷ may be unsubstituted or substituted with one or more substituents selected from halogen, hydroxy, cyano, C₁₋₆ haloalkoxy, or R⁷ forms a ring together with R⁶ as described herein; R⁸ is selected from hydrogen, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₁₋₆ alkoxy, cyano and halogen, wherein each alkyl or alkoxy may be unsubstituted or substituted with one or more substituents selected from halogen and C₁₋₃ alkoxy, or forms a ring system together with R⁹, as described herein; R⁹ is selected from hydrogen, halogen, cyano, azide, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₂₋₆ alkenyl, C₂₋₆ alkynyl and halogen, wherein each alkyl or alkoxy can be unsubstituted or substituted with one or more substituents selected from halogen and C₁₋₃ alkoxy,or R⁹ together with R⁸ or R¹⁰ and the C atoms to which they are attached forms a 5 or 6-membered ring that can be optionally further substituted and that can contain one or more ring-forming heteroatoms selected from N, S, O and Se; wherein the ring formed by R⁹ together with R⁸ or R⁹⁰ and the ring to which they are attached are selected from a bicyclic ring system selected from (a) 2,1,3-benzothiadiazole, (b) 2,1,3-benzoselenadiazole, (c) 2,1,3-benzoxadiazole, (d) 1,3-benzothiazole, (e) 1,3-benzoxazole which may be unsubstituted or may be partially hydrogenated and unsubstituted or substituted with oxo, (f) 1,3-benzodioxol which may be unsubstituted or substituted with one or two substituents selected from fluoro and methyl, (g) benzothiophene, which may be unsubstituted or may be partially hydrogenated and unsubstituted or substituted with one or two substituents selected from oxo, methyl or fluoro, wherein the benzothiophene is partially hydrogenated to 1,(h) 3-dihydro-2-benzothiophene, which can be optionally substituted with two oxos to form 1,1-dioxido-2,3-dihydro-1-benzothiophene, and which can be optionally substituted further, (h) 1,3-dihydro-2-benzofuran which can be substituted with oxo to form 3-oxo-1,3-dihydrobenzofuran, which can be optionally substituted further with one or more, and (i) 2,3-dihydro-1H-isoindole, which is either unsubstituted or substituted with oxo to give 3-oxo-2,3-dihydro-1H-isoindole, which can be optionally substituted further; R¹⁰ is selected from hydrogen, halogen, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cyano, C₁₋₆ cyanoalkyl, C₁₋₆ cyanoalkyloxy, C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylthio, C₃₋₆ cycloalkyl, C₃₋₆ cycloalkyloxy, C₃₋₆ heterocycloalkyl, C₃₋₆ heterocycloalkyl, amino, azido, pentafluorosulfanyl, nitro, C₁₋₃ alkylaminocarbonyl, di-C₁₋₃ alkylaminocarbonyl,C₁₋₃ alkylsulfinyl and C₁₋₃ alkylsulfonyl, wherein each alkyl, alkenyl, alkynyl or alkoxy group may be unsubstituted or substituted with one or more substituents selected from halogen, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ hydroxyalkoxy, optionally halogenated C₁₋₆ alkylthio, optionally halogenated C₁₋₃ alkylcarbonyl, optionally halogenated C₁₋₃ alkyloxycarbonyl, optionally halogenated C₁₋₃ alkylsulfonyl, optionally halogenated C₁₋₃ alkylsulfinyl, C₁₋₃ alkylaminocarbonyl, C₁₋₃ dialkylaminocarbonyl, hydroxy, cyano, nitro, oxo, C₃₋₆ cycloalkyl, C₃₋₆ cycloalkoxy, C₃₋₆ heterocycloalkyl, C₃₋₆ heterocycloalkoxy, phenyl, phenyloxy and C₅₋₆ heteroaryl, wherein any C₃₋₆ cycloalkyl, C₃₋₆ heterocycloalkyl, phenyl and heteroaryl residues may be unsubstituted or substituted with one or more residues selected from halogen, hydroxy, hydroxymethyl, oxo, cyano, nitro, amino, optionally halogenated or hydroxylated C₁₋₃ alkyl, optionally hydroxylated or halogenated,optionally hydroxylated or halogenated C₁₋₃ alkoxy, optionally halogenated C₁₋₃ alkylcarbonyl, and optionally halogenated C₁₋₃ alkoxycarbonyl, wherein the amino group may be substituted with one or two groups selected from C₁₋₃ alkyl, C₁₋₃ alkylsulfonyl, C₁₋₃ alkylcarbonyl, and C₁₋₃ alkoxycarbonyl, or R⁹⁰ forms a ring system together with R⁹, as described herein; R¹¹ is selected from hydrogen, halogen, cyano, azide, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl, C₁₋₆ alkylsulfonyl, and C₁₋₆ alkylsulfinyl, C₂₋₆ alkenyl, and C₂₋₆ alkynyl, wherein each alkyl or alkoxy can be unsubstituted or substituted with one or more substituents selected from halogen and halogenated or unsubstituted C₁₋₃ alkoxy; R¹², if present, is selected from hydrogen, C₁₋₆ alkyl, C₁₋₆ alkoxy and halogen, wherein each alkyl or alkoxy can be unsubstituted or substituted with one or more substituents selected from halogen and C₁₋₃ alkoxy,halogenated or unsubstituted; and pharmaceutically acceptable salts, solvates, isotopes and co-crystals thereof.

Claims

1. A (aza)indole or benzofuran-3-sulfonamide compound characterized in that it is selected from the following list: TABLES FOLLOW, and any pharmaceutically acceptable salt, solvate, isotope, and cocrystal thereof. 26 Claims follow