Synthesis and Biological Activity of 4-Amino-5-chloro-2-ethoxy-3-hydroxybenzamides, Metabolites of a New Gastroprokinetic Agent, Mosapride

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概要

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• To confirm the proposed structures of the minor metabolites of a potential gastroprokinetic agent, mosapride, 4-amino-5-chloro-2-ethoxy-3-hydroxy-N-(2-morpholinylmethyl)benzamide (3) and the N-(5-oxo-2-morpholinyl)-methyl analogue 4 were prepared. As the common intermediate, 2-ethoxy-3-hydroxy-4-nitrobenzoic acid (15) was propared via the regioselective ethylation of 2,3-dihydroxybenzaldehyde (10) and subsequent nitration of the resultant 2-ethoxy-3-hydroxybenzaldehyde (11). The key intermediate 15 was converted into the benzamides 3 and 4. After enzymatic treatment of the isolated metabolites, their structures were identified by comparison with the synthetic compounds. Serotonin-4 receptor binding affinity of these metabolites was found to be lower than that of mosapride.

• 社団法人日本薬学会の論文
• 1996-08-15

著者

• 森江 俊哉

  大日本製薬株式会社創薬研究所

• Kato Satoru

  Kanazawa Univ. Kanazawa Jpn

• 賀登 志朗

  大日本製薬株式会社創薬研究所

• YOSHIDA Naoyuki

  Discovery Pharmacology II Group, Pharmacolgy & Microbiology Research Laboratories, Dainippon Pharmac

• MORIE Toshiya

  Discovery Research Laboratories I, Dainippon Pharmaceutical Co., Ltd.,

• KATO Shiro

  Discovery Research Laboratories I, Dainippon Pharmaceutical Co., Ltd.,

• Kato S

  Discovery Research Laboratories I Dainippon Pharmaceutical Co. Ltd.

• Kato S

  Chemistry Research Laboratories Dainippon Pharmaceutical Co. Ltd.

• Kato Shiro

  Discovery Research Laboratories I Dainippon Pharmaceutical Co. Ltd.

• 吉田 直之

  大日本製薬株式会社創薬研究所

• Yoshida Naoyuki

  Discovery Pharmacology Ii Group Pharmacolgy & Microbiology Research Laboratories Dainippon Pharm

• Yoshida N

  Discovery Research Laboratories I Dainippon Pharmaceutical Co. Ltd.

• Kato Satoru

  Department Of Molecular Neurobiology Graduate School Of Medicine University Of Kanazawa

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