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Synthesis and analgesic activity of cyclohexenylmethylamines and related compounds.

1984; Pharmaceutical Society of Japan; Volume: 32; Issue: 6 Linguagem: Inglês

10.1248/cpb.32.2279

1347-5223

Takeshi Kato, Harumitsu Ishii, Kiyohisa Kawai, YOICHI SAWA,

Synthesis of heterocyclic compounds

N, N-Dimethyl-(6-benzyl-2-cyclohexenyl) methylamine derivatives (I) were prepared by dehydrochlorination of the 1, 2-cis-N, N-dimethyl-(6-benzyl-2-chlorocyclohexyl) methylamines (XII), which were obtained by the reaction of the 1, 2-trans-cyclohexanol derivatives (X) with thionyl chloride. The cyclohexenylmethylamine derivatives and related compounds were examined for analgesic activity by using the phenylquinone writhing method. Some of them, in particular, 1, 6-trans-N, N-dimethyl-(6-benzyl-4, 4-dimethyl-2-cyclohexenyl) methylamine hydrochloride (37) showed pronounced pharmacological activities. Structure-activity relationships are discussed.