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Preparation method of desacetylcefotaxime

A technology of acetyl cefotaxime and D-7-ACA, which is applied in the field of preparation of deacetyl cefotaxime, can solve the problems such as not found, and achieve the effect of improving production quality, simple and fast synthesis operation, and easy separation and purification

Inactive Publication Date: 2019-03-22
河北合佳医药科技集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there is no literature report on the preparation of this impurity by means of chemical synthesis and purification in China, and at the same time, no relevant synthesis information has been found abroad. Especially essential for impurity profile research for the consistency evaluation of generic cefotaxime sodium

Method used

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  • Preparation method of desacetylcefotaxime

Examples

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Comparison scheme
Effect test

Embodiment 1

[0036] Add 15.14g of D-7-ACA, 150mL of dichloromethane, 30mL of isopropanol into a 250mL four-necked bottle, stir at a temperature of 5-10°C, add 20.10g of AE-active ester, continue stirring evenly, add 2g of sodium metabisulfite 15 mL of triethylamine was slowly added dropwise, and the dropwise addition was completed in about 20 minutes. The reaction was stirred for 3 hours, and the temperature was controlled at 5-10°C. Then wash the water phase once with 50 mL of dichloromethane; discard the dichloromethane, decolorize the water phase with an appropriate amount of activated carbon, filter, control the temperature at 0-5°C, add 60 mL of isopropanol to the filtrate, stir, and slowly add 10 % hydrochloric acid solution, adjust the pH of the system to 1.0-2.0, stir for 30 minutes, filter with suction, dry the filter cake under reduced pressure in an oven at 40°C for 4 hours, and weigh to obtain 18.45g of the product (yield 52.36%). The purity (HPLC) of the target product obtaine...

Embodiment 2

[0038] Add 15.02g of D-7-ACA, 150mL of dichloroethane, 30mL of isopropanol into a 250mL four-necked bottle, stir at a temperature of 0-5°C, add 20.08g of AE-active ester, continue stirring evenly, add 2g of heavy Sodium sulfite, slowly add 15mL of triethylamine dropwise, the dropwise addition is completed in about 20min, stir the reaction for 3h, under the condition of temperature control 10-15°C, extract the reaction solution with purified water 3 times, 40mL each time, separate the liquid, collect and combine the aqueous phase , and then wash the water phase once with 50mL dichloroethane; discard the dichloroethane, decolorize the water phase with an appropriate amount of activated carbon, filter, control the temperature at 0-5°C, add 60mL isopropanol to the filtrate, stir, and then slowly Add 10% hydrochloric acid solution dropwise, adjust the pH of the system to 2.0-3.0, stir for 30 minutes, filter with suction, dry the filter cake under reduced pressure in an oven at 40°C ...

Embodiment 3

[0040]Add 15.08g of D-7-ACA, 150mL of dichloromethane and 30mL of methanol into a 250mL four-necked bottle, stir at -5-0°C under temperature control, add 20.01g of AE-active ester, continue stirring evenly, add 2g of sodium metabisulfite, Slowly add 15 mL of triethylamine dropwise, and the dropwise addition is completed in about 20 minutes. Stir the reaction for 3 hours. Under the condition of temperature control at 10-15°C, extract the reaction solution with purified water 3 times, 40 mL each time, separate the liquids, collect and combine the aqueous phases, and then Wash the water phase once with 50 mL of dichloromethane; discard the dichloromethane, decolorize the water phase with an appropriate amount of activated carbon, filter, control the temperature at 0-5°C, add 60 mL of methanol to the filtrate, stir, and slowly add 10% hydrochloric acid solution dropwise , adjust the pH of the system to 3.0-4.0, stir for 30 minutes, filter with suction, dry the filter cake in an ove...

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Abstract

The invention discloses a preparation method of desacetylcefotaxime. According to the method, D-7-ACA and AE-active ester are taken as reaction materials, and matching control is performed on raw material ratio, reaction temperature and system acidity or alkalinity, so that a desacetylcefotaxime finished product is formed. The invention provides a technical method for preparing desacetylcefotaximethrough a chemical synthesis means, can obtain desacetylcefotaxime standard substance with high yield, purity and convenience, and further improves the production quality of cefotaxime sodium.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation process of deacetylcefotaxime. Background technique [0002] Cefotaxime sodium ([6R-[6A,7B(Z)]]-3-[(acetoxy)methyl]-7-[2-(2-amino-4-thiazolyl)-2-(form Oxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]-2-octene-2-carboxylate) is the third broad-spectrum cephalosporin It has strong bactericidal activity against Gram-negative bacteria and positive bacteria, and its antibacterial effect on Escherichia coli, influenza bacillus, pneumonia bacillus, Proteus mirabilis, and Salmonella is stronger than that of cefoperazone; it is usually used for sensitive bacteria. It is also effective for infections caused by burns, trauma, sepsis, and central nervous system infections. [0003] Cefotaxime sodium degrades to deacetylcefotaxime during storage. Cefotaxime sodium containing deacetylcefotaxime will reduce the stability and curative effect of the drug; affect the quality a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/06
CPCC07D501/06C07D501/34
Inventor 刘振强孟龙超刘东娜梁丙辰曹晓倩王宇栋孙美婷姜鹏鹏
Owner 河北合佳医药科技集团股份有限公司
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