Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents. IV. Modification of the Phenylpiperazino Moiety of 2-(Phenylpiperazino-alkoxyphenyl)thiazolidine-3-carbothloamides and the Corresponding Carboxamides(Medicinal Chemistry,Chemical)

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概要

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• Examination of the structure-activity relationships of 2-(phenylpiperazinoalkoxyphenyl)-thiazolidine-3-carbothioamides and the corresponding carboxamides (1) as new cardiotonic agents was extended by the chemical modification of the phenylpiperazino moiety. The 4-phenylpiperidme (13), 4-phenyltetrahydropyridines (17), and related derivatives were prepared from the chlorides (10) through several intermediates (12, 14, and 16) and tested for cardiotonic activity. Generally, both the 4-phenylpiperidine (13) and 4-phenyltetrahydropyridine (17) derivatives exhibited potent positive inotropic activity comparable to that of 1. The W-phenylpiperidines (9) and amide derivatives (22, 25, and 28) exhibited no significant positive inotropy. This is also the case for the phenylpropylamines (29) and the ethylenediamines (30), which are pseudo-ring analogues of 1 with respect to the piperazine moiety. The activity of the homopiperazine derivative (23) was approximately one-thirtieth of that of the corresponding piperazine derivative (1). Thus, the presence of the six-rnembered, basic azacycloalkane ring(piperidine or piperazine) with a 4-phenyl group at the end of the alkoxy side chain appears to be essential for the appearance of potent positive inotropic activity in this series of compounds.

• 社団法人日本薬学会の論文
• 1987-07-25

著者

• 石田 昭彦

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 松木 健司

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 武田 幹男

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 名手 博行

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 渡辺 章重

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 井上 勲

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 大塚 久男

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 関根 康雄

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 小田 邦幸

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 本間 靖

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 管野 毅

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 近田 美紀彦

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 仲井 英雄

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 和田 博

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 武田 幹夫

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 矢花 秀雄

  Biological Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 長尾 拓

  Biological Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 関根 康雄

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 大塚 久男

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 和田 博

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co . Ltd.

• 井上 勲

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 渡辺 章重

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 仲井 英雄

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 関根 康雄

  タナベセイヤク

• 長尾 拓

  Department Of Toxicology And Pharmacology Faculty Of Pharmaceutical Sciences University Of Tokyo

• 仲井 英夫

  田辺製薬研

• 中井 英雄

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 名手 博行

  タナベセイヤク

• Nakai H

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• Nate H

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 矢花 秀雄

  Department Of Toxicology And Pharmacology Faculty Of Pharmaceutical Sciences University Of Tokyo

• 大塚 久雄

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 本間 靖

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 管野 毅

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 武田 幹男

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 小田 邦幸

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 松木 健司

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 名手 博行

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 近田 美紀彦

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

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