ω-Aminosubstituted-acetanilide誘導体の合成とそれらの薬理作用

概要

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3', 4' (or 3', 5')-Dichloro-ω-(3-methylpiperidino) acetamidodiphenyl ether (1a, b) was obtained by reduction of the corresponding nitrophenyl ether derivative with stannous chloride and concentrated hydrochloric acid, followed by reactions with chloroacetyl chloride and 3-methylpiperidine. 3'-Chloro-β-(3-methylpiperidino) propionamidodiphenyl ether (2) was obtained by reactions of the corresponding aminodiphenyl derivative with β-bromopropionyl chloride, next with 3-methylpiperidine. 4'-Chloro-ω-(piperidino) acetamidodiphenyl ether (11) and 2 were reacted with methyl iodide to give their corresponding quaternary salts (3-4). ω-(4-Ethoxycarbonyl-4-phenylpiperidino) acetanilide derivatives (5a-w) and ω-(4-hydroxy-4-phenylpiperidino) acetanilide derivatives (6a-w) were obtained by reactions of the corresponding ω-chloroacetanilide derivatives with 4-ethoxycarbonyl-4-phenylpiperidine and 4-hydroxy-4-phenylpiperidine, respectively. The investigation of the effects of the derivatives 1a-b and 3-4 on the intestinal smooth muscle showed that the quaternary salt 3,more weak than 11,competes with acetylcholine. The analgetic action and the action on central nervous system of derivatives 5a-w and 6a-w were both weak.
公益社団法人日本薬学会の論文
1980-05-25