GB1415295A — Substituted phenoxy-alkyl-carboxylic acids and derivatives thereof

USPTO Abstract

1415295 Phenoxyalkyl-carboxylic acid derivatives ORCHIMED SA 16 Oct 1972 [14 Oct 1971 (2)] 47926/71 and 47927/71 Heading C2C Novel compounds I (in which R<SP>II</SP> and R<SP>V</SP> are H, CH 3 , C 2 H 5 , C 6 H 5 , p-chlorophenyl or p-fluorophenyl; R<SP>III</SP> and R<SP>IIII</SP> are H, halo, 1-5C alkyl, CF 3 , SCH 3 , SOCH 3 , SO 2 CH 3 , OCH 3 , OH, C 6 H 5 or substituted phenyl; R<SP>VI</SP> is H, 1-5 C alkyl, aryl-optionally substituted by CH 3 , CF 3 or halo-, cycloalkyl, OH, 1-6 C alkoxy, optionally substituted aryloxy, cycloalkoxy, cycloalkenyloxy, NR 3 R 4 , NHCH 2 CH 2 NR 3 R 4 or -O-alkylene-NR 3 R 4 ; Y<SP>1</SP> is OH, 1-4C alkoxy, -NR 3 R 4 , or -O-alkylene-NR 3 R 4 ; X<SP>1</SP> is O or -NORO ; R 0 is H, 1-5C, -CH 2 CH 2 NR 3 R 4 or and R 3 and R 4 are H, 1-5C alkyl, 3-7C cycloalkyl or aryl optionally substituted by halo, CH 3 and/or CF 3 ; or NR 3 R 4 is a 5-7 membered heterocyclic ring, optionally containing a further heteroatom selected from O, S and N, or is -NH(CH 2 ) 4 CH(NH 2 )COOH or -NHCH(COOH)CH 2 SH; with the provisos that (i) if R<SP>III</SP> and R<SP>IIII</SP> are not both H, then R<SP>VI</SP> is CH 3 or p-chlorophenyl and (ii) if Y<SP>1</SP> is OH or alkoxy, R<SP>VI</SP> is H or 1-5 C alkyl and one of R<SP>II</SP> and R<SP>V</SP> is H, then the other of R<SP>II</SP> and R<SP>V</SP> is CH 3 or C 2 H 5 ) are prepared by conventional chemical processes. Compounds claimed in Specification 1,268,321 are specifically disclaimed. 4 - Hydroxy - 41 i chlorobenzophenone is prepared by reaction of phenol with p-chlorobenzoyl chloride in the presence of AlCl 3 . Ethyl p-carboxyphenoxyacetate is prepared by reaction of ethyl bromoacetate with p-hydroxybenzoic acid. Pharmaceutical compositions useful as analgesics, anti-inflammatory agents, psychotropic agents, cardiovascular agents, anti-tussive agents, normolipemiants and hypocholesterolemiants comprise a compound I together with a suitable diluent or carrier.