Synthesis and antiinflammatory activity of 3-chloro-4-cyclopropylmethoxyphenylacetic acid and its alpha-methyl homologue.

The synthesis of 3-chloro-4-cyclopropylmethoxyphenylacetic acid (I) from 3-chloro-4-hydroxyacetophenone (III) by the etherification with cyclopropylmethyl bromide and by the Willgerodt reaction is described. The alpha-methyl homologue (II) was also prepared from 4-benzyloxy-3-chlorophenylacetate (VIII). The antiinflammatory, analgesic and antipyretic activities of the lysine salts of (I) (ISF 2508) and (II) (ISF 2606) were tested in comparison with alclofenac and phenylbutazone. The new ocmpounds compare favourably with the standards; in particular ISF 2508 was selected for further pharmacological studies.