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Preparation method of cefminox sodium

A technology of cefminox sodium and cephem, which is applied in the field of preparation of cefminox sodium, can solve the problems of cumbersome processing, unsuitability for industrial application, and many steps of refining and purification, and achieve simple operation process, uniform crystal form, and fluidity Good results

Active Publication Date: 2014-04-02
HAINAN HULUWA PHARMA GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are many steps of refining and purification, and the treatment is cumbersome, so it is not suitable for industrial application.

Method used

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  • Preparation method of cefminox sodium
  • Preparation method of cefminox sodium
  • Preparation method of cefminox sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of cefminox sodium

[0031] 1674.4g (3.52mol) 7β-bromoacetamide-7α-methoxyl group-3-(1-methyl-1H-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid and 855.4 Add g (7.04mol) D-cysteine ​​hydrochloride into 2730ml of water, stir to dissolve, adjust the pH of the reaction system to 6.8 with a 10% aqueous sodium bicarbonate solution by mass percent, and keep stirring at 0°C for 2 hours. Afterwards, the temperature was raised to 2°C, and the reaction was stirred for 2.5 hours, and the stirring rate was maintained at 450 rpm. After the reaction was completed, the reaction liquid was purified by a chromatographic column filled with non-polar macroporous resin X5, and water was used as the eluent. The eluent was collected, concentrated under reduced pressure, cooled, and a solid was precipitated, filtered to obtain 1900 g of a crude solid product, which was dissolved in 7β-bromoacetamide-7α-methoxyl-3-(1-methyl-1H-5-tetrazolyl) Based on thiomethyl-3-cephem-4-carbo...

Embodiment 2

[0035] Preparation of cefminox sodium

[0036]7β-bromoacetamide-7α-methoxy-3-(1-methyl-1H-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid 1674.4g (3.52mol) and D -Add 855.4g (7.04mol) of cysteine ​​hydrochloride into 2730ml of water, stir and dissolve, adjust the pH value of the reaction system to 6.0 with a 10% aqueous solution of sodium bicarbonate, and react with stirring at -5°C After 1.5 hours, raise the temperature to 1.5°C, stir for 1.5 hours, and keep the stirring rate at 300 rpm. After the reaction, the reaction solution is purified by a chromatographic column filled with non-polar macroporous resin X5, and water is used as the elution eluent, collected eluent, concentrated under reduced pressure, cooled, precipitated solid, filtered to obtain 1880g solid crude product, and 7β-bromoacetamide-7α-methoxy-3-(1-methyl-1H-5-tetrazole Based on thiomethyl-3-cephem-4-carboxylic acid, the yield of the crude product is 98.62%, the mp of the crude product is 85.8°C to 86.3°C...

Embodiment 3

[0040] Preparation of cefminox sodium

[0041] 7β-bromoacetamide-7α-methoxy-3-(1-methyl-1H-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid 1674.4g (3.52mol) and D -Add 855.4g (7.04mol) of cysteine ​​hydrochloride into 2730ml of water, stir and dissolve, adjust the pH value of the reaction system to 7.0 with a 10% aqueous solution of sodium bicarbonate with a concentration of 10% by mass, and react with stirring at -3°C After 2.5 hours, raise the temperature to 3°C, stir for 2 hours, and keep the stirring rate at 400 rpm. After the reaction, purify the reaction solution through a chromatographic column filled with non-polar macroporous resin X5, using water as the eluent , collected the eluent, concentrated under reduced pressure, cooled, precipitated solid, and filtered to obtain 1890g solid crude product, which was converted to 7β-bromoacetamide-7α-methoxy-3-(1-methyl-1H-5-tetrazolyl ) thiomethyl-3-cephem-4-carboxylic acid), the yield of the crude product is 99.15%, the m...

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Abstract

The invention discloses a preparation method of cefminox sodium, which comprises the following steps: 7 beta-bromoacetamide-7 alpha-methoxy-3-(1-methyl-1H-5-tetrazyl)sulfur methyl-3- cephem-4-carboxylic acid and D-cysteine hydrochloride are dissolved in water, the pH value is regulated to 6.0-7.0 by sodium bicarbonate, condensation reaction is carried out, and reaction products are post-treated to obtain the cefminox sodium. In the method, cefminox sodium raw material can be prepared through low-temperature reaction, a nonpolar macroporous resin X5 chromatography column is used for purification, ethanol-aqueous solution or anhydrous alcohol recrystallization and other simple operations are adopted to obtain target products, the yield and the purity of the target products are high, the products have uniform crystal forms and good fluidity, no special equipment is needed for the production, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a preparation method of cefminox sodium. Background technique [0002] Anti-infective drugs are a powerful weapon for human beings to fight against infectious diseases. They are the largest in number, most in variety, and fastest growing, and the market demand for drugs in this area has always been very strong. According to statistics, the sales of anti-infective drugs account for about 15% of the world's drug sales, second only to cardiovascular drugs. In my country, anti-infective drugs account for about 14% of the total drug sales market share, ranking first among all types of drugs. [0003] Cefminox sodium, chemical name: (+)-(6R,7S)-7-[(S)-2-(2-amino-2-carboxyethylthio)acetamido]-7-methoxy- 3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2- Sodium ene-2-carboxylate, CAS number: 75498-96-3, molecular weight: 541.56, molecular fo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/36C07D501/04
Inventor 刘全国陈克领
Owner HAINAN HULUWA PHARMA GRP CO LTD
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