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■ Synthesis of Novel Potent Non-narcotic Less Side-effect Analgesics: 2’-Acylthio- and 2’-Alkylthio-6,7-benzomorphans

Mikio Hori, Masatoshi Ban, Eiji Imai, Noriyuki Iwata, Yutaka Baba, Hajime Fujimura, Masakatsu Nozaki, and Masayuki Niwa

*Department of Pharmacognosy, Gifu College of Pharmacy, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

2’-Acylthio- and 2’-alkylthio-6,7-benzomorphans were synthesized from 2’-hydroxy-6,7-benzomorphans in 4 steps. Newman-Kwart rearrangement of 2’-N,N-dimethylthiocarbamoyloxy derivatives proceeded in almost quantitative yields to give rearranged 2’-N,N-dimethylcarbamoylthio derivatives. Reductive cleavage and successive acylation afforded title compounds. These novel sulfur-containing benzomorphans showed strong analgesic activities with less side effects.