DERIVATIVES OF THE 2-(LOWER ALKYL)-3-(LOWER ALKYL)-4-PHENYL-3- OR 4-CYCLOHEXENECARBOXYLIC ACIDS

摘要

1,237,054. Cyclohexene carboxylic acid ester derivatives. ORTHO PHARMACEUTICAL CORP. 25 Sept., 1969 [26 Sept., 1968 (2)], No. 47324/69. Heading C2C. Novel compounds I in which R is H, 1-7 C alkanoyloxy, halo, cyclopentoxy, OH, 1-7 C alkyl or 1-7 C alkoxy; R11 and R111 are 1-3 C alkyl; R1 is 9-20 C alkyl, 2-20 C alkenyl, hydroxy-1-7 C alkyl, dihydroxy-1-7 C alkyl, adamantyl, adamantyl-1-7 C alkyl, furyl, furyl-1-7 C alkyl, phenyl, phenyl-1-7 C alkyl, diphenyl- 1-7 C alkyl, cycloalkyl, cycloalkyl-1-7 C alkyl, carbo-1-7 C alkoxy-1-7 C alkyl, 1-7 C alkoxy-1-7 C alkyl, carbo-1-7 C alkoxyphenyl, piperidyl, piperidyl-1-7 C alkyl or phenylcyclohexenylmethyl in which the phenyl group may be substituted by R and the cyclohexenyl group is substituted by H or 1-3 C alkyl and the dotted lines represent a 3- or 4- double bond are prepared (1) by reacting the appropriate acid halide with R1OH; (2) by reacting an appropriate metal salt with R1 halide or R1-SO 2 alkyl; (3) by reacting an approriate anhydride with R1OH; (4) by dehydration of a compound II in the presence of a Lewis acid; (5) esterifying an appropriate acid with R1OH; (6) by transesterifying one compound I into one in which R1 has a different value under basic catalysis or (7) by reacting an appropriate acid with R 1 R 2 CN 2 or R 1 R 2 C=CR 3 R 4 (R 1 -R 4 are substituted or unsubstituted alkyl or alkenyl radicals. Intermediates isolated are the acid chlorides corresponding to compounds I and are prepared by reaction of thionyl chloride with the appropriate acid. Pharmaceutical compositions for parenteral or oral administration as reproduction suppressing agents comprise a compound I, together with a suitable carrier and/or diluent.