Imidazo[1,2-α]pyridines. II. Ozonolysis of Imidazo[1,2-α]pyridines and Synthesis of Carfiotonic Agents

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概要

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• The metabolite of loprinone (E-1020) in dogs, 5-(2-aminopyridin-5-yl)-1,2-dihydro-6-methyl-2-oxo-3-pyridine-carbonitrile (9), was prepared via ozonolysis of imidazo[1,2-α]pyridinylpyridines and evaluated for positive inotropic activity. Its potency was less than that of loprinone and milrinone. Among compounds related to loprinone which were synthesized using the versatile intermediates (10a, b) obtained during the preparation of 9,only 5-(2-aminoimidazo[1,2-α]pyridin-6-yl)-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile (27) retained the activity of loprinone. The electron-withdrawing substituents at hte 2-position of imidazo[1,2-α]pyridine reduced the activity of the parent compound.The ozonolysis of imidazo[1,2-α]pyridine derivatives under neutral confitions afforded 2-acylaminopyridine derivatives in a 30-55% yield independent of the substituents at the 2-position of imidazo[1,2-α]pyridine. It is possible to use imidazo[1,2-α]pyridine as protected 2-aminopyridines, and 2,3-unsubstituted imidazo[1,2-α]pyridines are convenient for that purpose from the viewpoint of ease of preparation of the starting material.

• 公益社団法人日本薬学会の論文
• 1992-03-25

著者

• 須田 眞次

  エーザイ株式会社 筑波研究所

• 米田 直樹

  エーザイ株式会社 筑波研究所

• 山中 基資

  Eisai Tsukuba Research Laboratories

• 須田 眞次

  Eisai Tsukuba Research Laboratories

• 大原 秀人

  Eisai Tsukuba Research Laboratories

• 山中 基資

  Eisai Co. Ltd. Tsukuba Research Laboratories

• 米田 直樹

  Eisai Tsukuba Research Laboratories

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