Oxime ether derivatives, a new class of nonsteroidal antiinflammatory compounds

Article abstract of DOI:10.1021/jm00219a018

A series of new 2-hydroxyethyl and carboxyalkyl ethers of aromatic oximes was found to possess pronounced antiinflammatory activity in the carrageenan-induced edema test in the rat. The activity was limited mainly to derivatives of p-haloacetophenone oxime and of p-halobenzaldehyde oxime. Nevertheless the hydroxyethyl and carboxyalkyl groups may be converted into many derivatives with maintenance of activity. Some structure-activity relationships are in contrast to those of the well-known antiinflammatory arylacetic acids. The activity is limited to the E stereoisomers. The hydrochloride of 2-(dimethylamino)ethyl (E)-[[(p-chloro-α- methylbenzylidene)-amino]oxy]acetate (36, INN name Cloximate) was cosen for clinical evaluation. The first results agree with the pharmacological prospects.