Nonpeptide Arginine Vasopressin Antagonists for Both V_<1A> and V_2 Receptors : Synthesis and Pharmacological Properties of 4'-(1,4,5,6-Tetrahydroimidazo[4,5-d][1]benzoazepine-6-carbonyl)benzanilide Derivatives and 4'-(5,6-Dihydro-4H-thiazolo[5,4-d][1]ben

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概要

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• Arginine vasopressin (AVP) has a dual action mainly in the periphery, i.e., vasoconstriction and water reabsorption via V_<1A> and V_2 receptors; it may play a role in a number of diseases, including congestive heart failure (CHF), hypertension, renal discase, edema, and hyponatremia. We have attempted to develop a new series of orally active AVP antagonists for both V_<1A> and V_2 receptors based on the hypothesis that the blockade of both V_<1A> and V_2 receptors might be beneficial to CHF patients. In this report, a series of compounds structurally related to 4'-(1,4,5,6-tetrahydroimidazo[4,5-d][1]benzoazepine-6-carbonyl)benzanilide and 4'-(5,6-dihydro-4H-thiazolo[5,4-d][1]benzoazepine-6-carbonyl)benzanilide were synthesized and examined for AVP antagonist activity for both V_<1A> and V_2 receptors. As a result, it was found that the 4'-(1,4,5,6-tetrahydroimidazo[4,5-d][1]benzoazepine-6-carbonyl)-2-phenylbenzanilide derivatives showed potent binding affinity for both V_<1A> and V_2 receptors. Especially, 4'-(2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzoazepine-6-carbonyl)-2-phenylbenzanilide monohydrochloride (18,YM087=conivaptan hydrochloride) exhibited potent binding affinity and AVP antagonist activity, after intravenous administration, for both V_<1A> and V_2 receptors. Furthermore, YM087 exhibited the most potent oral activity for the V_2 receptor. Details of the synthesis and pharmacological properties of this series are presented.

• 公益社団法人日本薬学会の論文
• 2000-01-01

著者

• TANAKA Akihiro

  Institute for Drug Discovery Research, 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

• 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.

• 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.

• Tanaka Akihiro

  Institute For Drug Discovery Research Yamanouchi Pharmaceutical Co. Ltd.

• KOSHIO Hiroyuki

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

• Koshio Hiroyuki

  Institute For Drug Discovery Research Yamanouchi Pharmaceutical Co. Ltd.

• Yatsu Takeyuki

  Astellas Pharma Inc. Ibaraki Jpn

• Tahara Atsuo

  Drug Discovery Research Astellas Pharma Inc.

• Matsuhisa Akira

  Institute For Drug Discovery Research Astellas Pharma Inc.

• Koshio Hiroyuki

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

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