1-(3-CHLORO-4-CYCLOALKYLPHENYL)-CYCLO-ALKYL-1-CARBOXYLIC ACIDS

1277239 1- Phenyl - cycloalkane - 1 - carboxylic acids;. TAKEDA YAKUHIN KOGYO KK 4 July 1969 [4 July 1968 13 July 1969 18 Jan 1969] 33732/69 Heading C2C Novel 1 - phenyl - cycloalkane - 1 - carboxylic acids of the general formula wherein X is a hydrogen or halogen atom, R is a C 3-6 alkyl or cycloalkyl group and n is an integer of from 2 to 5, and pharmaceutically acceptable salts or derivatives thereof derived by conversion of the carboxylic group, i.e. acid amides and esters and hydroxamic acids, are prepared (a) by reaction of a phenyl-acetonitrile of the. general formulawith an alkylene halide of the general; formula X1(CH 2 ) n X1, wherein X1 is a halogen atom, followed optionally by halogenation and/or hydrolysis. of the resulting 1-phenyl-cycloalkane-1-nitrile of the general formula (b)- byhalogenation of a phenyl'-acetonitrile of the second general. formula above and reaction of the resulting-phenyl-acetonitrile of the.general formula wherein X11 is a halogen atom, with an alkylene halide of the third general formula above, followed optionally by hydrolysis of the resulting 1-phenyl-cycloalkane-1-nitrile of the general formula and (c) when n is 2 ,by reaction of diazomethane with, an α-phenyl-acrylic acid of the general formula. or a pharmaceutically acceptable salt or deriva; tive thereof derived by conversion of the carboxylic group and denitrification of the resultting 3 - phenyl - 1 - pyrazoline - 3 - carboxylic acid of the general formula or pharmaceutically acceptable salt or derivative thereof derived by conversion of the carboxylic group, followed optionally by conversion of a resulting 1-phenyl-cycloalkane-1,-carboxylic acid of the first general formula above to a pharmaceutically acceptable salt or derivative thereof derived by conversion of the carboxylic group (other than a nitrile in the case of (a) and (b) above), or by conversion of a resulting pharmaceutically acceptable salt or derivative of a 1-phenyl-cycloalkane- 1 -carboxylic acid of the first general, formula above derived by conversion of the carboxylic group to the free acid. Pharmaceutical compositions having antiinflammatory activity comprise, as active ingredient, a 1-phenylcycloalkane-carboxylic acid of the first general formula above or a pharmaceutically acceptable salt or derivative thereof derived by conversion of the carboxylic group, in admixture with a pharmaceutically acceptable carrier or adjuvant, and may be administered orally or by way of injection.