Patent HU-9903371-A2 (HU)
Title: Carboxylic acid derivatives, their production and use of them for producing pharmaceutical compositions
Inventor: DR AMBERG WILHELM
IPC: C07D215/22
Filed: 1997-04-04
Abstract: 2-(Hetero)aryloxyalkanoic acid derivatives of formula (I) are new. X = N or CR12; Y = N or CH; Z = S or O; R = tetrazole, nitrile, CHO, COOR8, COO(CH2)pS(O)kR7 or C(O)R1, CONHSO2R9, COCH2SO2R9 or NR10R11; R1 = succinylimidoxy or N-linked 5-membered heteroaromatic (such as pyrrolyl, pyrazolyl, imidazolyl or triazolyl) (optionally substituted by 1 or 2 halo, 1-4C alkyl or 1-4C alkoxy; R2 = H, OH, NH2, NH(1-4C alkyl), N(1-4C alkyl)2, halo, 1-4C alkyl, 1-4C haloalkyl, 1-4C alkoxy, 1-4C haloalkoxy or 1-4C alkylthio; R3 = H, OH, halo, 1-4C alkyl, NH2, 1-4C haloalkyl, 1-4C alkoxy, 1-4C haloalkoxy, NH(1-4C alkyl), N(1-4C alkyl)2, NH(1-4C alkoxy) or 1-4C alkylthio; R4, R5 = Ph or naphthyl (optionally substituted by V, 1-4C haloalkoxy or phenoxy) or 3-7C cycloalkyl; R4+R5 = ortho-linked Ph or naphthyl, (where the link is a bond, methylene, ethylene, ethenylene, O, S, SO2, NH or N-alkyl; R6 = H, 1-8C alkyl, 3-6C alkenyl or 3-6C alkynyl (where the groups are optionally substituted by halo, OH, SH, COOH, NO2, CN, 1-4C alkoxy, 3-6C alkenyloxy, 3-6C alkynyloxy, 1-4C alkylthio, 1-4C haloalkoxy, 1-4C alkylcarbonyl, 1-4C alkoxycarbonyl, 3-8C alkylcarbonylalkyl, 1-4C alkylamino, 1-4C dialkylamino, or Ph or OPh (both optionally substituted halo, NO2, CN, 1-4C alkyl, 1-4C haloalkyl, 1-4C alkoxy, 1-4C haloalkoxy or 1-4C alkylthio), Ph, naphthyl (both optionally substituted by V, 1-4C haloalkoxy, phenoxy, dioxomethylene or dioxoethylene), or 5-6 membered heteroaryl (containing 1-3N and/or 1 S or O, optionally substituted by 1-4 halo and/or 1-2 1-4C alkyl, 1-4C haloalkyl, 1-4C alkoxy, 1-4C haloalkoxy, 1-4C alkylthio, Ar, OAr or COAr); Ar = phenyl (optionally substituted by 1-5 halo and/or 1-3 1-4C alkyl, 1-4C haloalkyl, 1-4C alkoxy, 1-4C haloalkoxy or 1-4C alkylthio); k = 0-2; p = 1-4; R7 = 1-4C alkyl, 3-7C cycloalkyl, 3-6C alkenyl, 3-6C alkynyl or Ph (optionally substituted by 1 or more V); V = halo, NO2, CN, 1-4C alkyl, 1-4C haloalkyl, OH, 1-4C alkoxy, 1-4C alkylthio, SH, NH2, 1-4C alkylamino or 1-4C dialkylamino); R8 = H, alkali or alkaline earth metal (such as Li, Na, K, Ca, Mg or Ba), NH4, organic ammonium (such as tert. (1-4C alkyl)ammonium), 3-8C cycloalkyl, 1-8C alkyl, benzyl (optionally substituted by 1 or more of V or 3-6C alkenyl or 3-6C alkynyl (both optionally substituted by 1-5 halo), Ph (optionally substituted by 1-5 halo and/or 1-3 other V), or N-linked 5-membered heteroaromatic (containing 1-3N, and substituted by 1-2 halo and/or 1-2 of 1-4C alkyl, 1-4C haloalkyl, 1-4C alkoxy, Ph, 1-4C haloalkoxy or 1-4C alkylthio), (especially optionally substituted pyrazolyl, triazolyl or imidazolyl); R9 = 1-4C alkyl, 3-6C alkenyl, 3-6C alkynyl or 3-8C cycloalkyl (all optionally substituted by 1-4C alkoxy, 1-4C alkylthio and/or Ph) or optionally substituted Ph; R10, R11 = halo, 1-7C alkyl, 3-7C cycloalkyl, 3-7C alkenyl, 3-7C alkynyl, benzyl or Ph (optionally substituted); or R10+R11 = 4-7C alkylene optionally containing a heteroatom (optionally substituted by 1-4C alkyl); R12 = H or 1-5C alkyl; or CR12+CR2 or CR12+CR3 complete a 5-6 membered alkylene or alkenylene ring (optionally with one CH2 replaced by NH, N(1-4C alkyl), S or O, and optionally substituted by 1 or 2 of 1-4C alkyl).