Cefminox sodium compound reducing adverse reactions and preparation thereof

A cefminox sodium and adverse reaction technology, applied in the field of antibiotics, can solve the problems of unsecured safety, complicated synthesis operation process, low yield of final product, etc. Simple and effective in reducing adverse reactions

Active Publication Date: 2016-09-07
福安药业集团庆余堂制药有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis operation process of this method is complex, and after repeated extractions, the yield of the final product is low, and a large amount of organic solvents are used, so the safety cannot be guaranteed
[0010] The above-mentioned synthetic methods all use relatively toxic reagents or solvents, and the preparation process is complicated and the yield is low.

Method used

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  • Cefminox sodium compound reducing adverse reactions and preparation thereof
  • Cefminox sodium compound reducing adverse reactions and preparation thereof
  • Cefminox sodium compound reducing adverse reactions and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) 358g 7β-amino-7a-methoxy-3-(1-methyl-1H-tetrazolium-5-thiomethyl)-3-cephem-4-carboxylic acid and 94.5g chloroacetic acid were dissolved In 3L of dichloromethane, add 30g of 3A molecular sieve and 200g of magnesium sulfate, react at 40°C, TLC detects that the reaction is complete, filter, wash with water, and distill off the solvent under reduced pressure to obtain 433g of 7β-chloroacetamido-7a-methoxy- 3-(1-Methyl-1H-tetrazole-5-thiomethyl)-3-cephem-4-carboxylic acid;

[0029] (2) 433g 7β-chloroacetamido-7a-methoxy-3-(1-methyl-1H-tetrazolium-5-thiomethyl)-3-cephem-4-carboxylic acid and 157gD-semi Add cystine hydrochloride to 2L water, then add 20g EDTA and 309g sodium thiosulfate, react at 30°C, TLC detects that the reaction is complete, cool to room temperature, add 2L acetone, precipitate crystals, filter, and dry to obtain 528g cefamidox Nuo sodium, the yield is 97.5%, and the purity is determined by HPLC, and the purity is 99.2%.

Embodiment 2

[0031] (1) 358g 7β-amino-7a-methoxy-3-(1-methyl-1H-tetrazolium-5-thiomethyl)-3-cephem-4-carboxylic acid and 99.2g chloroacetic acid were dissolved In 3L of chloroform, add 40g of 3A molecular sieve and 220g of sodium sulfate, react at 50°C, TLC detects that the reaction is complete, filter, wash with water, and distill off the solvent under reduced pressure to obtain 432.2g of 7β-chloroacetamido-7a-methoxy-3 -(1-Methyl-1H-tetrazole-5-thiomethyl)-3-cephem-4-carboxylic acid;

[0032](2) 432.2g 7β-chloroacetamido-7a-methoxy-3-(1-methyl-1H-tetrazolium-5-thiomethyl)-3-cephem-4-carboxylic acid and 164.5gD - Add cysteine ​​hydrochloride to 2L of water, then add 25g of EDTA and 370g of sodium thiosulfate, react at 40°C, TLC detects that the reaction is complete, cool to room temperature, add 2L of ethanol, precipitate crystals, filter, and dry to obtain 525g Cefminox sodium, the yield is 97%, and the purity measured by HPLC is 99.0%.

Embodiment 3

[0034] (1) 358g 7β-amino-7a-methoxy-3-(1-methyl-1H-tetrazolium-5-thiomethyl)-3-cephem-4-carboxylic acid and 104g chloroacetic acid were dissolved in 2.5L ethyl acetate, add 20g 3A molecular sieve and 250g calcium chloride, react at 60°C, TLC detects that the reaction is complete, filter, wash with water, and distill off the solvent under reduced pressure to obtain 433.1g 7β-chloroacetamido-7a-methoxy Base-3-(1-methyl-1H-tetrazol-5-thiomethyl)-3-cephem-4-carboxylic acid;

[0035] (2) 433.1g 7β-chloroacetamido-7a-methoxy-3-(1-methyl-1H-tetrazolium-5-thiomethyl)-3-cephem-4-carboxylic acid and 173gD- Add cysteine ​​hydrochloride to 2L water, then add 30g EDTA and 412g sodium thiosulfate, react at 50°C, TLC detects that the reaction is complete, cool to room temperature, add a mixed solution of 1500ml ethanol and 500ml acetone, and crystallize. Filter and dry to obtain 530g cefminox sodium, the yield is 97.9%, and the purity measured by HPLC is 99.5%. Comparative example 1:

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Abstract

The invention relates to an antibiotic drug, in particular to a preparation process of cefminox sodium compound reducing adverse reactions and a preparation of the cefminox sodium compound. The preparation process has the advantages such as high yield and high purity and is suitable for industrial production, and an obtained product has significant improvements in terms of product stability, preparations to reduce adverse reactions, and clinical application.

Description

technical field [0001] The invention relates to an antibiotic, in particular to a cefminox sodium compound capable of reducing adverse reactions and a preparation thereof. Background technique [0002] Cefminox sodium is a third-generation cephalosporin developed by Meiji Seika Co., Ltd. in Japan in 1987 and has been widely used in my country. Cefminox has broad-spectrum antibacterial activity against Gram-positive and Gram-negative bacteria, especially against Escherichia coli, Klebsiella, Haemophilus influenzae, Proteus and Bacteroides fragilis . Its mechanism of action is that it has a strong affinity for the penicillin-binding protein at the usual site of action of β-lactam antibiotics, can inhibit the synthesis of cell walls, and bind to peptidoglycan, inhibiting the combination of peptidoglycan and lipoprotein to promote bacteriolysis. Shows strong bactericidal power in a short time. This product is suitable for respiratory system infection, urinary system infection...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/57C07D501/04A61K31/546A61K9/14A61K47/02A61P31/04
CPCA61K9/0019A61K9/143A61K31/546C07D501/04C07D501/57
Inventor 蒋晨胡昌勤周晓东
Owner 福安药业集团庆余堂制药有限公司
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