Preparation of Non-peptide, Highly Potent and Selective Antagonists of Arginine Vasopressin V_<1A> Receptor by Introduction of Alkoxy Groups

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概要

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• A series of compounds structurally related to 4'-[(4, 4-difluoro-5-methylidene-2, 3, 4, 5-tetrahydro-1H-1-benzoazepin-1-yl) carbonyl] benzanilide were synthesized and evaluated for arginine vasopressin (AVP) antagonistic activity. Compounds with alkoxy groups (especially ethoxy group) at the 2'-position of benzanilide possessed potent affinity and selectivity for the V_<1A> receptor versus V_2 receptor. Further study has shown that the introduction of 4, 4-dimethylaminopiperidino and morpholino groups at carbonylmethylene exhibited more potent affinity and selectivity for V_<1A> receptors. Consequently, we found that the (Z)-4'-({4, 4-Difluoro-5-[(4-dimethylamino-piperidino)carbonylmethylene]-2, 3, 4, 5-tetrahydro-1H-1-benzoazepin-1-yl}carbonyl)-2-ethoxybenzanilide monohydrochloride (8d) and the (Z)-4'-[(4, 4-Difluoro-5-morpholinocarbamoylethylene-2, 3, 4, 5-tetrahydro-1H-1-benzoazepin-1-yl) carbonyl]-2-ethoxybenzanilide (8q) exhibited potent and selective V_<1A> receptor antagonist activity. The synthesis and pharmacological properties of these compounds are detailed in this paper.

• 公益社団法人日本薬学会の論文
• 2003-09-01

著者

• TANAKA Akihiro

  Corporate Communications Department, Yamanouchi Pharmaceutical Co., Ltd.

• Tanaka A

  Faculty Of Pharmaceutical Sciences Tokyo University Of Science

• Tanaka A

  Yamanouchi U.k. Ltd. Surrey Gbr

• 増田 明

  富山医科薬科大学麻酔科

• SHIMADA Yoshiaki

  Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd.

• TANIGUCHI Nobuaki

  Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd.

• MATSUHISA Akira

  Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd.

• YATSU Takeyuki

  Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd.

• TAHARA Atsuo

  Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd.

• Yatsu Takeyuki

  Institute For Drug Discovery Research Yamanouchi Pharmaceutical Co. Ltd.

• Matsuhisa Akira

  Institute For Drug Discovery Research Yamanouchi Pharmaceutical Co. Ltd.

• Matsuhisa Akira

  Gastrointestinal Research Laboratories Institute For Drug Discovery Research Yamanouchi Pharmaceutic

• Taniguchi Nobuaki

  Institute For Drug Discovery Research Yamanouchi Pharmaceutical Co. Ltd.

• Shimada Yoshiaki

  Institute For Drug Discovery Research Yamanouchi Pharmaceutical Co. Ltd.

• Yatsu Takeyuki

  Astellas Pharma Inc. Ibaraki Jpn

• Tanaka Akihiro

  Corporate Communications Department Yamanouchi Pharmaceutical Co. Ltd.

• Tahara Atsuo

  Drug Discovery Research Astellas Pharma Inc.

• Matsuhisa Akira

  Institute For Drug Discovery Research Astellas Pharma Inc.

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