GB1353362A - Alpha-phenoxy-alkonic acids and derivatives thereof - Google Patents

Abstract

1353362 α-Phenoxyacetic acids CIBAGEIGY AG 17 June 1971 [10 Dec 1970 5 Feb 1971 7 May 1971] 28455/71 Addition to 1332824 Heading C2C Novel α-phenoxyacetic acids in which the α-position is substituted by an alkyl residue having 5 to 12 carbon atoms and the phenyl residue is substituted by a singly unsaturated cycloalkenyl residue the double bond of which extend from the carbon atom adjacent to the phenyl residue to an adjacent carbon atom, or an ester or amide thereof may be prepared by condensation of a phenol that is substituted by a singly unsaturated cycloalkenyl residue the double bond of which extend from the carbon atom adjacent to the phenyl residue to an adjacent carbon atom, with an ester of a glycolic acid that is reactively esterified at the alcoholic hydroxyl group and is substituted in the α- position by a C 5-12 alkyl residue and, if desired, forming a free acid, an amide or a salt thereof or resolving isomers. The intermediates p-(1-cyclohexenyl) and (1- cyclo-octenyl)-phenol may be prepared by forming a Grignard reagent with p-bromo anisole, reacting it with cyclohexanone or cyclo-octanone, followed by dehydration of p-(1-hydroxycyclohexyl) anisole to p-(1-cyclohexenyl)-anisole (p-(1-cyclo-octenyl)-anisole is formed directly as the product of the Grignard reaction), followed by demethylation to form the free phenol. Pharmaceutical compositions of the α-phenoxyacetic acids have a serum-lipid-lowering action when administered orally, parenterally or rectally with the usual excipients.