Synthesis of 2-Aryl-2,3-dihydro-3-piperazinylmethyl-1,5-benzothiazepin-4(5H)-ones and Related Compounds
スポンサーリンク
概要
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A series of trans- (12) and cis-2-aryl-2,3-dihydro-3-piperazinylmethy-1,5-benzothiazepin-4(5H)-ones(13) and related compounds were synthesized. Diethyl arylmethylenemalonates (3) were heated with 2-aminobenzenethiol (4) in the presence of triethylamine hydrochloride to afford trans-2-aryl-3-ethoxycarbonyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-ones (7) together with 2-aryl-benzothiazoles (6). Heating of the adducts of 3 and 4 also gave 6 and 7. Reduction of 7 yielded the 3-hydroxymethyl compounds (8), which were converted to the 3-chloromethyl (9), 3-methanesulfonyloxymethyl (10), and 3-(4-toluenesulfonyloxymethyl) compounds (11). Heating of 9-11 with piperazines gave 12 and 13. Optical resolution of the 2-phenyl-3-piperazylmethyl (13a) and 2-phenyl-3-(4-methylpiperazinylmethyl) compounds (13b) afforded (-)-13a, an active metabolite of (-)-13b, and (-)-13b (hydrochloride : BTM-1086), a potent anti-ulcer agent with gastric antisecretory and gastric mucosal blood flow-increasing activities, respectively.
- 公益社団法人日本薬学会の論文
- 1988-02-25
著者
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堀 幹夫
Gifu Pharmaceutical University
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大野 左千雄
Research Laboratories, Maruko Seiyaku Co., Ltd.,
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水越 清史
Research Laboratories, Maruko Seiyaku Co., Ltd.,
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水越 清史
Research Laboratories Maruko Seiyaku Co. Ltd.
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泉 喜八郎
Research Laboratories, Maruko Pharmaceutical Co., Ltd.,
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加藤 和雄
Research Laboratories, Maruko Pharmaceutical Co., Ltd.,
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加藤 和雄
Research Laboratories Maruko Pharmaceutical Co. Ltd.
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大野 左千雄
Research Laboratories Maruko Seiyaku Co. Ltd.
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大野 佐千雄
Research Laboratories Maruko Pharmaceutical Co. Ltd.
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泉 喜八郎
Research Laboratories Maruko Pharmaceutical Co. Ltd.
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