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Synthetic method of carbenicillin sodium impurity G

A technology of carbenicillin sodium and synthesis method, which is applied in the field of medicinal chemistry, can solve problems such as poor stability and difficult preparation of carbenicillin sodium impurity G, and achieve the effects of environmental friendliness, high product purity, simple and safe preparation

Inactive Publication Date: 2016-12-07
SHANGHAI NEW ASIA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The present invention aims at overcoming the above-mentioned defects, and provides a kind of environmentally friendly, simple and safe process for preparing carbenicillin sodium impurity G, which can solve the problem of difficult preparation of carbenicillin sodium impurity G, while overcoming carbenicillin sodium impurity G. Benzicillin sodium impurity G and carbenicillin sodium impurity D are in poor stability due to interconversion during the preparation process or after obtaining the product

Method used

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  • Synthetic method of carbenicillin sodium impurity G
  • Synthetic method of carbenicillin sodium impurity G
  • Synthetic method of carbenicillin sodium impurity G

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] At room temperature, 20g penicillin sodium was dissolved in 100ml water, slowly added dropwise 10M sodium hydroxide aqueous solution, kept the solution pH value between 11.5-12.5, stirred for 2 hours. Slowly add 75% concentrated hydrochloric acid to the reaction solution to adjust the pH value to about 5.4, add 300ml of isopropanol under stirring, and cool the mixture to 1-5°C, filter and dry to obtain 18.1g of white crystal G.

Embodiment 2

[0055] Dissolve 20g of penicillin sodium in 200ml of water, slowly add 20M potassium hydroxide aqueous solution dropwise, keep the pH value of the solution at around 13, and react with stirring at 50°C for 1 hour. Heat filtration to remove insoluble matter, place the filtrate in an ice-salt bath, add 5M acetic acid while stirring, adjust the pH value to about 4, add 95% ethanol while stirring, until no new crystals are produced, and The mixture was cooled to -5-0°C for 1 hour to fully crystallize, and 12.5 g of white crystals G were obtained by filtration, and 11.9 g of crystals were obtained after repeated washing with ethanol and drying.

Embodiment 3

[0057] Dissolve 20g of penicillin sodium in 50ml of water, slowly add 5M sodium ethoxide aqueous solution dropwise, keep the pH value of the solution at about 10, and stir at room temperature for 10 hours. After the reaction is over, add 10M formic acid, adjust the pH value to about 6, add acetone while stirring until no new crystals are produced, and cool the mixture to 1-5°C to fully crystallize for 10 hours, filter and bake After drying, 8 g of crystals were obtained.

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Abstract

The invention provides a synthetic method of carbenicillin sodium impurity G. In the method, penicillin sodium is subjected to a degradation reaction under the effect of a strong alkali to prepare the carbenicillin sodium impurity G at lower than 50 DEG C. The method can effectively control inter-conversion between the carbenicillin sodium impurity G and carbenicillin sodium impurity D, is environment-friendly, is simple and safe, is high in product purity and provides guarantee for researching on quality control and inspection of impurities of a carbenicillin sodium product.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a method for synthesizing the impurity G of carbenicillin sodium. Background technique [0002] Carbenicillin is a broad-spectrum semisynthetic antipseudomonal penicillin. The product is carbenicillin sodium salt. The mechanism of action of carbenicillin is to affect the synthesis of bacterial cell wall by interfering with mucopeptide cross-linking, resulting in defect or weakness of cell wall, deformity of bacteria, followed by rapid dissolution and death, thus playing an antibacterial effect. Carbenicillin is a broad-spectrum semi-synthetic penicillin. Its antibacterial spectrum is basically similar to that of ampicillin. It is characterized by its strong effect on Pseudomonas aeruginosa and indole-positive Proteus, and its effect on other Gram-positive and negative bacteria is similar to or weaker than that of ampicillin. This product is not resistant to penicillinase and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/06
CPCC07D277/06
Inventor 管海英蒋海平崔万胜曾垂宇商鼎
Owner SHANGHAI NEW ASIA PHARMA