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Synthesis method of cefpiramide side chain acid

The technology of a cefpiramide and a synthetic method is applied in the field of synthesis of cefpiramide side chain acid, which can solve the problems of poor product stability and low product yield, and achieve the effects of low cost, easy availability of raw materials, and convenient industrial production

Inactive Publication Date: 2020-05-08
YIYUAN XINQUAN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Single non-polar solvent is mostly used when the existing process synthesizes cefpiramide side chain acid, which has the disadvantages of poor product stability and low product yield

Method used

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  • Synthesis method of cefpiramide side chain acid
  • Synthesis method of cefpiramide side chain acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The synthetic method of the cefpiramide side chain acid described in present embodiment 1, the steps are as follows:

[0035] (1) Chlorination and acylation

[0036] Add 22g of pyridine-3-carboxylic acid and 25.4g of HPGE into a mixed solvent consisting of 480ml of dichloromethane and 80ml of DMAC, stir at normal pressure and cool down to -25°C, add 4.2ml of pyridine, and then slowly dropwise add 13.4ml of phosphorus oxychloride , Control the temperature during the dropwise addition to not exceed -15°C, after the dropwise addition, control the temperature at -15°C, and react for 5 hours.

[0037] (2) Hydrolysis and crystallization

[0038] After the reaction, the temperature was raised to 15°C, and then 30% sodium hydroxide solution was slowly added dropwise to the reaction solution to adjust the pH to 8.5, and the reaction was carried out at 15°C for 1 hour. After the reaction, add 240ml of water and 1.0g of sodium metabisulfite to the reaction bottle; slowly add 480...

Embodiment 2

[0040] The synthetic method of the cefpiramide side chain acid described in present embodiment 2, the steps are as follows:

[0041] (1) Chlorination and acylation

[0042] Add 22g of pyridine-3-carboxylic acid and 28g of HPGE into a mixed solvent consisting of 468ml of dichloromethane and 55ml of DMAC, stir at normal pressure and cool down to -25°C, add 4.2ml of triethylamine, then slowly dropwise add 13.4ml of phosphorus oxychloride, During the dropwise addition, the temperature was controlled not to exceed -15°C. After the dropwise addition was completed, the temperature was controlled at -15°C, and the reaction was carried out for 5 hours.

[0043] (2) Hydrolysis and crystallization

[0044] After the reaction, the temperature was raised to 15°C, and then 30% sodium hydroxide solution was slowly added dropwise to the reaction solution to adjust the pH to 8.5, and the reaction was carried out at 15°C for 1 hour. After the reaction, add 240ml of water and 1.0g of sodium me...

Embodiment 3

[0046] The synthetic method of the cefpiramide side chain acid described in present embodiment 3, the steps are as follows:

[0047] (1) Chlorination and acylation

[0048] Add 22g of pyridine-3-carboxylic acid and 33g of HPGE to a mixed solvent consisting of 472ml of dichloromethane and 59ml of DMAC, stir at normal pressure and cool down to -25°C, add 4.2ml of pyridine, then slowly add 10.4ml of thionyl chloride dropwise, drop During the addition process, the temperature was controlled not to exceed -15°C. After the dropwise addition was completed, the temperature was controlled at -15°C, and the reaction was carried out for 5 hours.

[0049] (2) Hydrolysis and crystallization

[0050] After the reaction, the temperature was raised to 15°C, and then 30% sodium hydroxide solution was slowly added dropwise to the reaction solution to adjust the pH to 8.5, and the reaction was carried out at 15°C for 1 hour. After the reaction, add 240ml of water and 1.0g of sodium metabisulfi...

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthesis method of cefpiramide side chain acid. Pyridine-3-formic acid and methyl p-hydroxyphenylglycinate are used as raw materials, and the cefpiramide side chain acid is obtained through chlorination, acylation, hydrolysis and crystallization. The synthesis method of the cefpiramide side chain acid is simple to operate, easily available in raw materials and low in cost, adopts a dichloromethane and N, N-dimethylacetamide mixed solvent as a solvent, greatly improves the product yield and stability, has good economic benefits, and is convenient for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a synthesis method of cefpiramide side chain acid. Background technique [0002] Cefpiramide belongs to the third-generation cephalosporin antibacterial drug, which was jointly developed by Sumitomo Pharmaceutical Co., Ltd. and Yamanouchi Pharmaceutical Co., Ltd., and was first listed in Japan in 1985. It has been recorded in the American and Japanese Pharmacopoeias . Cefpiramide has a good antibacterial effect on many Gram-negative bacteria, including Pseudomonas aeruginosa, and is also effective against Staphylococcus. It is a fourth-generation cephalosporin in nature. Adverse reactions during application include allergic symptoms such as rash, urticaria, itching, and fever, and anaphylactic shock and pseudomembranous enteritis are rare. Those who have a history of allergy to cefpiramide are contraindicated. For those with liver and kidney dysfunction, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/87
CPCC07B2200/07C07D213/87
Inventor 常明珠张立明
Owner YIYUAN XINQUAN CHEM
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