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Prepn process of aztreonam

A technology of aztreonam and benzhydryl aztreonam, applied in the direction of organic chemistry, can solve the problems of high cost of trifluoroacetic acid, inability to recycle and apply, and inability to recycle, and achieve low cost, high yield, and mild reaction conditions Effect

Active Publication Date: 2007-06-06
CHINA RESOURCES SAIKE PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The more common problem in the above-mentioned method is that the cost of using trifluoroacetic acid in the reaction is high, and it cannot be recycled. The yield of hydrochloric acid or sulfuric acid is low, and ring-opening products are generated, and they cannot be recycled and applied mechanically, which is harmful to the environment.

Method used

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  • Prepn process of aztreonam
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  • Prepn process of aztreonam

Examples

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Effect test

Embodiment 1

[0023] Embodiment 1: Preparation of aztreonam by deprotection of tert-butyl aztreonam

[0024] Add 20g of tert-butylaztreonam and 100ml of anhydrous formic acid into a 250ml flask, stir and react at room temperature for 3 hours, after the reaction is completed, recover formic acid under reduced pressure, add 100ml of deionized water to the obtained oil, and stir at 0°C to 5°C After half an hour, a white solid was formed, filtered, the filter cake was washed with cold water and cold acetone, and dried to obtain 13.3 g of the product. Yield 75%.

Embodiment 2

[0025] Embodiment 2: Preparation of aztreonam by deprotection of tert-butyl aztreonam

[0026] Add 20g of tert-butylaztreonam and 100ml of 50% formic acid aqueous solution into a 250ml flask, stir and react at room temperature for 3 hours, after the reaction is complete, cool to 0°C-5°C and stir for 1 hour, a white solid is formed, filter, and collect the obtained formic acid aqueous solution Apply mechanically, filter cake is washed with cold water and cold acetone, and drying obtains 11.3g aztreonam product. Yield 63.8%.

Embodiment 3

[0027] Embodiment 3: benzhydryl aztreonam deprotection preparation aztreonam

[0028] Add 20g of benzhydryl aztreonam and 100ml of anhydrous formic acid into a 250ml flask, stir and react at room temperature for 3 hours, after the reaction is completed, recover formic acid under reduced pressure, add 100ml of deionized water to the obtained oil, After stirring for half an hour, a white solid was formed, filtered, the filter cake was washed with cold water and cold acetone, and dried to obtain 9.8 g of the product. Yield 68%.

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Abstract

The present invention relates to the preparation process of Aztreonam as one kind of antibacterial medicine. The preparation process includes the reaction of Aztreonam with protected side chain and formic acid or its water solution to obtain Aztreonam.

Description

Technical field: [0001] The invention relates to a synthesis method of an antibacterial drug aztreonam, which comprises the step of reacting side chain protected aztreonam with formic acid or formic acid aqueous solution to obtain aztreonam. Background technique: [0002] Aztreonam is an antibacterial drug developed by Bristol-Myers Squibb Company of the United States. It was launched in Italy in 1984. It is a monocyclic β-lactam antibiotic that can be synthesized artificially. The antimicrobial spectrum mainly includes Gram-negative bacteria, such as Escherichia coli, Klebsiella, Serratia, Proteus mirabilis, Haemophilus influenzae, Citrobacter, Pseudomonas aeruginosa, Neisseria gonorrhoeae, etc. It is mainly used clinically for respiratory tract, lung infection, urinary tract infection, abdominal infection, bone and joint infection, skin and soft tissue inflammation, gynecological infection, and gonorrhea caused by sensitive Gram-negative bacteria. Because aztreonam can en...

Claims

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Application Information

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IPC IPC(8): C07D417/12C07D277/00C07D205/00
Inventor 杨琰刘亚杰
Owner CHINA RESOURCES SAIKE PHARMA
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