Method for synthesizing cefuroxime sodium

A cefuroxime acid and synthetic method technology, applied in organic chemistry, antibacterial drugs, etc., can solve the problems of high production cost, removal of unfavorable impurities, and influence on product yield, so as to reduce production cost, increase product yield, and improve The effect of stability

Active Publication Date: 2008-10-22
YIYUAN XINQUAN CHEM
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AI Technical Summary

Problems solved by technology

Although the yields of these two steps are relatively high, the strong alkaline environment used in the first step is extremely destructive to β-lactam antibiotics, which not only affects the yield of the product but also damages the stability of the product. sex
A lar

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0025] Example 1:

[0026] 1. Preparation of MDCC (Decarbamyl Cefuroxime):

[0027] According to the preparation steps of Comparative Example 1, after the water phase was combined, cephalosporin ester hydrolase was used to remove the acetyl group at position 3, 24.25 g of solid phase cephalosporin ester hydrolase was added, and 15% (mass percentage) hydrogen was continuously used. Sodium oxide adjusts the pH so that the pH of the solution is controlled between 7.0 and 7.5, until the pH of the reaction solution is stable, and the crystallization procedure is the same as that of Comparative Example 1. After drying, 48.5 g of the dry product was obtained, the content was 96.22%, and the yield was 92.50%.

[0028] 2. Preparation of Cefuroxime Acid:

[0029] According to the preparation of Comparative Example 1, add purified water to complete the hydrolysis, add 320ml of purified water again, adjust the pH value of the feed solution to 6.0-6.2 with solid sodium carbonate, let it stand ...

Example Embodiment

[0030] Example 2

[0031] 1. Preparation of MDCC (Decarbamyl Cefuroxime):

[0032] According to the preparation steps of Comparative Example 1, after the water phase was combined, cephalosporin ester hydrolase was used to remove the 3-position acetyl group, and 45 g of solid phase cephalosporin ester hydrolase was added, and the pH was continuously adjusted with 15% sodium hydroxide. The pH of the solution is controlled between 7.0 and 7.2, until the pH of the reaction solution is stable and unchanged, and the crystallization procedure is the same as that of Comparative Example 1. After drying, 49.1 g of the dry product was obtained, the content was 96.72%, and the yield was 93.10%.

[0033] 2. Preparation of Cefuroxime Acid:

[0034] According to the preparation of Comparative Example 1, add purified water to complete the hydrolysis, add 320ml of purified water again, strictly control the jacket temperature at 35~40℃, the vacuum degree at 0.09~0.095MPa, and distill under reduced ...

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Abstract

The invention relates to a synthesis method for cefuroxime acid, which includes the following steps: (1) N-acylation reaction is first carried out by using 7-ACA and methoxy imino furan ammonium acetate as materials; then, the 3 bit acetyl of the reaction product is hydrolyzed; finally MDCC is crystallized out by using hydrochloride in water phase; (2) the MDCC and a strong carbamoyl agent P-isocyanate are done with nucleophilic addition in an organic solvent to obtain chlorosulfonation cefuroxime; cefuroxime acid is obtained after the hydrolyzation; then a product is crystallized. The main technical features of the method are as follows: the adoption of a strong alkaline environment is avoided during the period of the hydrolysis of the step (1); while the mild-conditioned enzymatic hydrolysis is adopted to cause the yield of the product to be improved by more than 8 percent and reach 93 percent, and the stability of the product can be improved at the same time. The cefuroxime acid of the step (2) crystallizing in the water phase environment facilitates the removing of impurities and acid media, improves the stability of products and lowers the production cost simultaneously.

Description

Technical field [0001] The invention relates to a method for synthesizing cefuroxime acid. Background technique [0002] Cefuroxime series belong to the second generation of cephalosporins, which have a broad-spectrum antibacterial effect. The distinguishing feature is the high stability of the hydrolytic enzymes that produce drug-damaging effects on bacteria, thus ensuring excellent antibacterial activity. It is rarely used in clinical applications. An adverse reaction occurred. [0003] Cefuroxime was first successfully developed and patented by Glaxo Wellcome. The product was first marketed in the UK, Ireland, Germany and Italy in 1978 under the trade name "Cilixin", and subsequently sold in many countries and regions around the world. It was approved by the U.S. FDA on December 28, 1987, and was listed in the U.S. in 1988. Because of its definite curative effect, it is widely used to fight various infections caused by sensitive fungi. In the early 1990s, the drug had become a...

Claims

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Application Information

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IPC IPC(8): C07D501/34A61P31/04
Inventor 刘成学陈传贵周磊
Owner YIYUAN XINQUAN CHEM
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