Title:
PRODUCTION OF CARBAPENEMS
Document Type and Number:
Japanese Patent JP3479720
Kind Code:
B2
Abstract:
PURPOSE: To obtain carbapenems in high yield by reacting an azetidine derivative with imidazoles, then reacting the resultant compound with an inorganic salt, a dicarboxylic acid derivative, an azide compound and an acid, carrying out the cyclizing reaction and further reacting the resultant reactional product with an acid.
CONSTITUTION: A compound expressed by formula I (R1 is protecting group of OH) is reacted with N,N'-carbonylimidazole or a halogenated carbonic acid ester and imidazole in the presence of a base to provide a compound expressed by formula II, which is then reacted with an inorganic salt and a compound expressed by the formula R2OOCCH2COOH (R2 is protecting group of carboxyl) to afford a compound expressed by formula III. The resultant compound is reacted with an azide compound and further with an acid to provide a compound expressed by formula IV, which is then subjected to the cyclizing reaction to afford a compound expressed by formula V. The obtained compound expressed by formula V is reacted with an acid expressed by the formula R3OH (R3 is acyl) or its reactive derivative to provide the objective compounds expressed by formula VI useful as a synthetic intermediate for 1- methylcarbapenem antibiotic substances having excellent antimicrobial action.
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Inventors:
Yoshitaka Fujiwara
Tomohiro Akiyama
Shuichi Nishimura
Toshimitsu Hatano
Toshio Kumagai
Hisashi Shimizu
Tomohiro Akiyama
Shuichi Nishimura
Toshimitsu Hatano
Toshio Kumagai
Hisashi Shimizu
Application Number:
JP18114492A
Publication Date:
December 15, 2003
Filing Date:
July 08, 1992
Export Citation:
Assignee:
Takeda GmbH
Japan Wysledding Co., Ltd.
Japan Wysledding Co., Ltd.
International Classes:
C07D477/00; (IPC1-7): C07D477/00
Domestic Patent References:
| JP1203367A | ||||
| JP125779A |
Other References:
Ｊ． Ａｍ． Ｃｈｅｍ． Ｓｏｃ．， １９８０， １０２， ｐ．６１６１−６１６３
Attorney, Agent or Firm:
Yo Sekiguchi (3 outside)
Shuichi Takahashi (3 others)
Shuichi Takahashi (3 others)