Oxime ether derivatives, a new class of nonsteroidal antiinflammatory compounds.
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-alpha-methylbenzylidene)-amino[oxy]acetate (36, INN name Cloximate) was chosen for clinical evaluation. The first results agree with the pharmacological prospects.
D000818:Animals; D000893:Anti-Inflammatory Agents; D004987:Ethers / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity; D007928:Lethal Dose 50; D051379:Mice; D010091:Oximes / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity; D051381:Rats; D013329:Structure-Activity Relationship
D000893:Anti-Inflammatory Agents; D004987:Ethers; D010091:Oximes