Synthesis and analgesic activity of some spiro[dibenz[b,f]oxepin-10,4'-piperidine] derivatives

Abstract
A series of 10,11-dihydro-11-oxospiro[dibenz[b,f]oxepin-10,4''-piperidine] derivatives was synthesized and evaluated for analgesic activity in the phenylquinone writhing assay (PQW) and the tail-flick test in mice. Preliminary structure-activity correlations indicate that optimum activity is associated with a short-chain (R .ltoreq. C2) N substituent and a nuclear fluorine function as exemplified by 9b. This compound when administered orally was equipotent to morphine in protecting against mouse writhing. The observation that the PQW activity of 9b remained relatively unchanged after naloxone challenge seems to favor a nonnarcotic profile.

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