Journal of Medicinal Chemistry 1979-05-01

Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates.

P M Manoury, A P Dumas, H Najer, D Branceni, M Prouteau, F M Lefevre-Borg

文献索引：J. Med. Chem. 22(5) , 554-9, (1979)

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摘要

A series of (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates has been prepared and screened for analgesic and antiinflammatory properties in mice and rats. The tabulated results reveal several 2-(4-substituted phenyl-1-piperazinyl)ethyl 2-(7- or 8-substituted 4-quinolinylamino)benzoates to be six to nine times more potent analgesics than the reference compounds (glafenine and aminopyrine) and to possess minor antinflammatory activity. Compound 45, 2-[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]ethyl 2-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoate (antrafenine), showed marked analgesic activity, long duration of action, and excellent tolerance in pharmacological and toxicological studies, as well as in clinical trials.