Patent DE-19903126-A1 (DE)
Title: New sulphur substituted sulphonylaminocarboxylic acid N-arylamide derivatives used for treating e.g. cardiovascular diseases and atherosclerosis
Inventor: SCHINDLER URSULA
IPC: C07D213/71
Filed: 1999-01-27
Abstract: Sulphur substituted sulphonylaminocarboxylic acid N-arylamide derivatives (I) are new. Sulphur substituted sulphonylaminocarboxylic acid N-arylamide derivatives (I) and their salts are new. A<1> = phenylene, naphthylene or heteroarylene (all optionally substituted by halo, 1-5C alkyl, phenyl, tolyl, CF3, NO2, OH, 1-5C alkoxy, O-(2-4C alkyl)-O-(1-3C alkyl), 1-2C alkylenedioxy, NH2, NH(1-3C alkyl), N(1-3C alkyl)2, NHCHO, NHCO(1-5C alkyl), CN, CONH2, CONH(1-3C alkyl), CON(1-3C alkyl)2, COOH, COO(1-5C alkyl), heterocyclyl, CHO, CO(1-5C alkyl), SOn-(1-4C alkyl), SOn-phenyl or SOn-tolyl); A<2> = benzene, naphthalene, saturated or partially unsaturated 3- to 7-membered carbocyclyl,  monocyclic 5- to 7-membered heterocyclyl containing one or more N, O or S atoms or bicyclic 8- to 10-membered heterocyclyl containing one or more N, O or S atoms; R<1> = aryl, heterocyclyl or 1-18C alkyl optionally substituted by R<4> or when n = 2, R<1> may also be NR<5>R<6> or when n = 0, R<1> may also be CN; R<2> = aryl, heterocyclyl, NR<5>R<6> or 1-10C alkyl optionally substituted by R<4>; R<3> = H, halo, CF3, OH, 1-7C alkoxy, O-(2-4C alkyl)-O-(1-7C alkyl), aryloxy, 1-2C alkylenedioxy, NO2, CN, NR<7>R<8>, CONR<7>R<8>, COOH, COO(1-5C alkyl), heterocyclyl, SOn-(1-5C alkyl) or 1-5C alkyl optionally substituted by R<4>; R<4> = F, OH, 1-10C alkoxy, O-(2-4C alkyl)-O-(1-7 alkyl), aryloxy, CN, NR<7>R<8>, CONH2, CONH(1-3C alkyl), CON(1-3C alkyl)2, COOH, COO(1-5C alkyl), heterocyclyl or oxo; R<5> = H, 1-10C alkyl (optionally substituted by R<4> and/or aryl), aryl, heterocyclyl, CONR<7>R<8>, CO-aryl or CO-(1-10C alkyl) (optionally substituted by R<4>); R<6>  = a group R<5> or NR<5>R<6> = 5- to 8-membered saturated or partially unsaturated ring also containing N, O or S and optionally substituted by one or more F, 1-5C alkyl, 1-3C hydroxyalkyl, (1-3C alkyl)-O-(1-4C alkyl), aryl, CF3, OH, 1-7C alkoxy, aryloxy, O-(2-4C alkyl)-O-(1-7C alkyl), 2-3C alkylenedioxy, NR<7>R<8>, CN, CONH2, CONH(1-3C alkyl), CON(1-3C alkyl)2, COOH, COO(1-5C alkyl), CHO, CO(1-5C alkyl), SOn-(1-4C alkyl), SOn-NH2, SOn-NH(1-3C alkyl), SOn-N(1-3C alkyl)2, oxo, (CH2)mNH2, (CH2)m-NH(1-4C alkyl) or (CH2)m-N(1-4C alkyl)2 (in which N-(1-4C alkyl)2 optionally forms a 5- to 7-membered ring also containing O, S or NR<5>); R<7> = H or 1-7C alkyl optionally substituted by OH, 1-5C alkoxy, NH2, NH(1-4C alkyl) or N(1-4C alkyl)2 which optionally forms a 5- to 7-membered ring also containing O, S or NR<5>; R<8> = a group R<7> or CO-(1-4C alkyl); aryl = phenyl, naphthyl or heteroaryl (all optionally substituted by one or more halo, 1-5C alkyl, phenyl, tolyl, CF3, OCF3, NO2, OH, 1-5C alkoxy, O-(2-4C alkyl)-O-(1-3C alkyl), 1-2C alkylenedioxy, NH2, NH(1-3C alkyl), N(1-3C alkyl)2, NHCHO, NHCO(1-5C alkyl), CN, CONH2, CONH(1-3C alkyl), CON(1-3C alkyl)2, COOH, COO(1-5C alkyl), heterocyclyl, CHO, CO-(1-5C alkyl), SOn-(1-4C alkyl), SOn-phenyl or SOn-tolyl); heteroaryl, heteroarylene = monocyclic 5- or 6-membered aromatic heterocyclyl or bicyclic 8- to 10-membered aromatic heterocyclyl each containing N, O or S; heterocyclyl = mono- or poly-cyclic 5- to 11-membered saturated or partially unsaturated heterocyclyl containing one or more N, O or S atoms and optionally substituted by one or more F, 1-5C alkyl, OH, 1-5C alkoxy, -O-(2-4C alkyl)-O-(1-3C alkyl), NH2, NH(1-3C alkyl), N(1-3C alkyl)2, CN, CONH2, CONH(1-3C alkyl), CON(1-3C alkyl)2, COOH or COO(1-5C alkyl); n = 0-2; m = 2-4 and X = O or NH or a N-atom forming an anellate imidazole ring; excluding (I) in which A<2> = 3,5-dichlorophenyl, R<2> = Me, X = O and R<1>-SOn-A<1> = 5-chloro-2-(4-chlorophenylmercapto)phenyl. An Independent claim is included for the preparation of (I).