Studies on the Synthesis of Condensed Heterocyclic Isoquinolone Derivatives. I. Studies on the Synthesis and Pharmacology of Thiazino, Oxazino and Pyrimido Isoquinolones

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概要

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• 5-Oxo-1,2,3,5-tetrahydro-5H-imidazo [1,2-b] isoquinoline (IIa) and related compounds were synthesized from homophthalic acid and an aliphatic 1,2- or 1,3-diamine. In addition, homophthalic acids or o-carboxyphenylmalonic acid diesters were allowed to react with an aliphatic 1,2- or 1,3-aminoalcohol or aminothiol with heating in the presence of p-toluenesulfonic acid, yielding a series of oxazolo- or oxazino-isoquinolones (VI) or thiazolo- or thiazino-isoquinolones (IV). Oxidation of IV gave the corresponding sulfoxides (VII) and sulfones (VIII). Treatment of o-cyanomethylbenzenesulfonyl chloride with an N-alkyl 1,2- or 1,3-diamine gave N-alkyl-imidazo- or pyrimido-benzothiazine-5,5-dioxide (XI). The compounds thus prepared were evaluated for their anti-inflammatory effect in rats, using the carrageenin paw edema method, and some of the condensed heterocyclic isoquinolone derivatives were found to exhibit strong anti-inflammatory activity. These compounds were also examined for analgesic activity in terms of the inhibition of acetic acid induced writhing. Compound VIIIk showed stronger anti-inflammatory activity than phenylbutazone, as well as analgesic activity comparable to that of aminopyrine, and had very low toxicity.

• 公益社団法人日本薬学会の論文
• 1979-10-25

著者

• 村上 増雄

  Central Research Laboratories, Yamanouchi Pharmaceutical Co., Ltd.

• 磯村 八州男

  Central Research Laboratories, Yamanouchi Pharmaceutical Co., Ltd.

• 伊藤 徳樹

  Central Research Laboratories, Yamanouchi Pharmaceutical Co., Ltd.

• 本間 弘茂

  Central Research Laboratories, Yamanouchi Pharmaceutical Co., Ltd.

• 久保 一夫

  Central Research Laboratories, Yamanouchi Pharmaceutical Co., Ltd.

• 久保 一夫

  Central Research Laboratories Yamanouchi Pharmaceutical Co. Ltd.

• 磯村 八州男

  Central Research Laboratories Yamanouchi Pharmaceutical Co. Ltd.

• 僧都 勲

  Central Research Laboratories, Yamanouchi Pharmaceutical Co., Ltd.

• 伊藤 徳樹

  Central Research Laboratories Yamanouchi Pharmaceutical Co. Ltd.

• 磯村 八州男

  山之内製薬

• 本間 弘茂

  Central Research Laboratories Yamanouchi Pharmaceutical Co. Ltd.

• 僧都 勲

  Central Research Laboratories Yamanouchi Pharmaceutical Co. Ltd.

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