Synthesis of Carumonam (AMA-1080) and a Related Compound Starting from (2R, 3R)-Epoxysuccinic Acid

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概要

• 論文の詳細を見る

• In the course of the chemical modification of sulfazecin, several 4-carbamoyl-2-azetidinone-1-sulfonic acid derivatives were synthesized with the aim of improving the antibacterial activity. Among those compounds, (3S, 4S)-3-[2-(2-aminothiazol-4-yl)-(Z)-2-(1-carboxy-1-methylethoxyimino) acetamido]-4-carbamoyl-2-azetidinone-1-sulfonic acid (2) was found to have potent antibacterial activity, comparable to that of carumonam (1,AMA-1080 ; Ro 17-2301), against gramnegative bacteria. Efficient synthetic pathways to prepare 1 and 2 in large quantities were developed based on (2R, 3R)-epoxysuccinic acid (5), an easily accessible fermentation product, as a starting chiral synthon.

• 社団法人日本薬学会の論文
• 1985-09-25

著者

• 岸本 彰二

  Pharmaceutical Research Laboratories Iii Takeda Chemical Industries Ltd.

• 千代 道行

  Central Research Division, Takeda Chemical Industries, Ltd.

• 橋口 昌平

  Central Research Division, Takeda Chemical Industries, Ltd.

• 冨本 光美

  Central Research Division, Takeda Chemical Industries, Ltd.

• 岸本 彰二

  Central Research Division, Takeda Chemical Industries, Ltd.

• 松尾 泰介

  Central Research Division, Takeda Chemical Industries, Ltd.

• 落合 道彦

  Central Research Division, Takeda Chemical Industries, Ltd.

• 岸本 彰二

  Pharmaceutical Research Laboratories Iii Pharmaceutical Research Division Takeda Chemical Industries

• 千代 道行

  Central Research Division Takeda Chemical Industries Ltd.

• 橋口 昌平

  Central Research Division Takeda Chemical Industries Ltd.

• 冨本 光美

  Central Research Division Takeda Chemical Industries Ltd.

• 落合 道彦

  Central Research Division Takeda Chemical Industries Ltd.

• 松尾 泰介

  Central Research Division Takeda Chemical Industries Ltd.

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