Sankyo Company, Limited

Eiichi Misaka

Atsusuke Terada

Shigeru Tanaka

Kazuyuki Wachi

Shunji Naruto

Phenylacetic derivatives of formula (I): ##STR1## (wherein R represents a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group and n represents an integer from 1 to 3) and salts and esters thereof have analgesic, antipyretic and anti-inflammatory activity and may be prepared by reducing the corresponding acid or ester having an oxo group at the 2-position of the cycloalkylidene ring system and, if necessary, salifying the resulting product.

Phenylacetic acid derivatives, their preparation and compositions

Compounds of formula (I): ##STR1## its salts, and resolved forms thereof, especially the compound of formula (II): ##STR2## and its salts are new analgesic and/or anti-inflammatory agents. The agents are prepared by resolution at the 2-position of a suitable starting material such as the compound (IV): ##STR3## or an optionally partly resolved form thereof, with subsequent reduction and optional resolution to give the trans form.

Analgesic and anti-inflammatory agents

Novel 4-(2-oxo-1-cycloalkylidenemethyl)phenylacetic acid derivatives and non-toxic pharmaceutically acceptable salts thereof are useful as anti-inflammatory agents. The compounds may be prepared by reacting a p-formylphenylacetic acid ester derivative with an enamine of cycloalkanone and hydrolyzing the resulting product, or with a cycloalkanone in the presence of a base.

Process for the preparation of cycloalkylidenemethylphenylacetic acid

Cycloalkylidenemethylphenylacetic acid derivatives and process for the

4-(2-Oxo- or hydroxyimino-cycloalkan-1-ylmethyl)phenylacetic acid derivative and nontoxic pharmaceutically acceptable salt thereof are useful as an anti-inflammatory agent. The above 2-oxo-compound may be prepared by (a) hydrolyzing and decarboxylating 4-(1-alkoxycarbonyl-2-oxocycloalkan-1-ylmethyl)phenylacetic acid ester derivative or (b) reacting p-halomethylphenylacetic acid ester derivative with an enamine of cycloalkanone and hydrolyzing the resulting product. And further, the above 2-hydroxyimino-compound may be prepared by (c) reacting 4-(2-oxocycloalkan-1-ylmethyl)phenylacetic acid derivative (the product of process (a) or (b)) with hydroxylamine or (d) reacting a dilithium salt of cycloalkanone oxime with p-halomethyl- or p-sulfonyloxymethyl-phenylacetic acid ester derivative and hydrolyzing the resulting product.

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Hiromachi, Japan

Eiichi Misaka