GB1240911A - Phenoxyacetic acids, process for their manufacture and compositions containing them - Google Patents

Abstract

1,240,911. Phenoxyacetic acids. CIBAGEIGY A.G. 1 April, 1969 [3 April, 1968; 27 Jan., 1969], No. 16956/69. Heading C2C. Novel compounds I in which R is a bicycloalkyl radical in which each ring has 5-7 ring members; Ph is an optionally substituted phenylene radical and " alk " is a 1-7C alkylene or 2-7C alkenylene radical and functional derivatives thereof are prepared by (1) reaction of compounds R-Ph-OH or salts thereof with a reactive ester of the alcohol HO-alk-Y, where Y is COOH or a functionally modified form thereof, (2) reaction of compounds R-Ph-OH or salts thereof with an alkanal, alkenal, alkanone or alkenone corresponding to the residue alk in the presence of a tri- or tetrahalogenated methane derivative and a strong base or (3) reducing the residue Z in a compound Z-Ph-O-alk-Y, where Z is a bicycloalkenyl or α-hydroxy-bicycloalkyl residue capable of being reduced to R and if desired in any of (1)-(3) forming a salt or converting a resulting salt into the free base or separating a mixture of isomers. Intermediates isolated are (A) 4-(3,4,5,6,7,8, 9,10 - octahydro - 1 - naphthyl) - anisole, prepared by reaction of 4-bromoanisole, Mg and 1-oxodecahydronaphthalene by a Grignard reaction; (B) 4 - (1 - decahydronaphthyl) - anisole prepared by reduction of (A); (C) 4-(1-decahydronaphthyl)-phenol, prepared by reaction of (B) with conc. HC1; the cis isomers of (A), (B) and (C) prepared similarly; and trans-4-(2-decahydronaphthyl)-phenol, prepared by reaction of 2- decahydronaphthol with phenol and AlCl 3 or by reaction of the corresponding cis-isomer with AlCl 3 . Pharmaceutical compositions comprise a compound I, together with suitable carriers and are administered enterally or parenterally as bloodcholesterol-level reducing agents.