Patent AU-725699-B2 (AU)
Title: Sulfonamide-substituted compounds, processes for their preparation, their use as a medicament or diagnostic, and pharmaceutical preparations comprising them
Inventor: BRENDEL JOACHIM
IPC: C07D207/325
Filed: 1997-12-15
Granted: 2000-10-19
Abstract: N-(Bicyclic aryl or heteroaryl)-sulphonamide or sulphamide derivatives of formula (I) and their salts are new: X = O, S, SO, SO2, NR7, CR'8R"8 or C=O; R7 = H or -CaH2a-R9, where one CH2 is optionally replaced by O, CH=CH, C  IDENTICAL  C, CO, CO2, OCO, S, SO, SO2, NR10 or CONR10; R10 = H or A; a = 0-8; R9 = H, CF3, C2F5, C3F7, 3-8 C cycloalkyl, NMe2, NEt2, 1-piperidyl, pyrrolidino, morpholino or 4-methyl-piperazin-1-yl, pyridyl, thienyl, imidazolyl or phenyl (the latter four all optionally substituted by 1 or 2 F, Cl, Br, I, CF3, NO2, CN, NH2, OH, Me, Et, OMe, NMe2, SO2NH2, SO2Me and NHSO2Me); or R1+R7 = bond; R'8 = H, CF3, C2F5, C3F7, 1-6 C alkyl or phenyl (optionally substituted by 1 or 2 F, Cl, Br, I, CF3, NO2, CN, NH2, OH, Me, Et, OMe, NMe2, SO2NH2, SO2Me and NHSO2Me); R"8 = H, A, OR10, CO2R10 or COR10; R10 = H or A; or R'8+R1 or R"8+R1 = bond if Y = N; Y = N or CR11; R11 = H or A; R1, R2 = H, CF3, C2F5, C3F7, F, Cl, OMe, 1-6 C alkyl or phenyl (optionally substituted by 1 or 2 F, Cl, Br, I, CF3, NO2, CN, NH2, OH, Me, Et, OMe, NMe2, SO2NH2, SO2Me and NHSO2Me); or CR1R2 = 2-10 C alkylene chain; R3 = R12-CnH2n-N(R13)- or R12-CnH2n-, where one CH2 of CnH2n is optionally replaced by O, CO, S, SO, SO2 or R'10; R'10 = H, Me or Et; R12 = H, Me, 3-8 C cycloalkyl, CF3, C2F5 or C3F7; n = 0-10; R13 = H or 1-6 C alkyl; or R12+R13 = bond if n ≥ 3; or R3+R4 = 3-8 C alkylene chain, where one CH2 is optionally replaced by O, CO, S, SO, SO2 or NR'10; R4 = R14-CrH2r-, where one CH2 of CrH2r is optionally replaced by O, CH=CH, C  IDENTICAL  C, CO, CO2, OCO, S, SO, SO2, NR"10 or CONR"10; R"10 = H or A; R14 = Me, CF3, C2F5, C3F7, 3-8 C cycloalkyl, OH, CO2H, NR23R24, 1-piperidyl, 1-pyrrolidinyl, 4-morpholinyl or 4-methylpiperazin-1-yl, pyridyl, thienyl, imidazolyl or phenyl (the latter four all optionally substituted by 1 or 2 F, Cl, Br, I, CF3, NO2, CN, NH2, OH, Me, Et, OMe, NMe2, SO2NH2, SO2Me and NHSO2Me); R23, R24 = H or A; or NR23R24 = (CH2)k, where one CH2 is optionally replaced by O, S, NH, NMe or N(CH2Ph); k = 4 or 5; r = 0-20; R5+R6 = -CR15=CR16CR17=CR18-, -CR15=CR16CR17=N-, -CR15=CR16N=CR18-, -CR15=N-CR17=N-, -CR15=NN=CR18-, -N=CR16CR17=N- or -SCR15=CR16-, all bonded in either direction; R15-R18 = H, F, Cl, Br, I, 1-5C alkyl, 3-8 C cycloalkyl, CN, CF3, C2F5, C3F7, N3, NO2, -Z-CsH2s-R22, thienyl or phenyl (optionally substituted by 1 or 2 F, Cl, Br, I, CF3, NO2, CN, NH2, OH, Me, Et, OMe, NMe2, SO2NH2, SO2Me and NHSO2Me); Z = O, CO, CO2, OCO, S, SO, SO2, SO2O, SO2NR'"10, NR'"10 or CONR'"10; R'"10 = H or A; s = 0-6; R22 = H, CF3, C2F5, C3F7, 3-8 C cycloalkyl, NR19R20, CO2R21, 1-piperidyl, 1-pyrrolidinyl, 4-morpholinyl or 4-methylpiperazin-1-yl, pyridyl, thienyl, imidazolyl, quinolyl, isoquinolyl or phenyl (the latter six all optionally substituted by 1 or 2 F, Cl, Br, I, CF3, NO2, CN, NH2, OH, Me, Et, OMe, NMe2, SO2NH2, SO2Me and NHSO2Me); R19, R20 = H or A; or NR19R20 = (CH2)k, where one CH2 is optionally replaced by O, S, NH, NMe or N(CH2Ph); R21 = H or A; and A = 1-3 C alkyl; provided that Y is not CR11 if X = O.