Preparation method for improving product quality of cefotaxime sodium

A technology for cefotaxime sodium and cefotaxime acid, which is applied in the field of organic synthesis, can solve the problems of unfavorable production, research and utilization, high product color grade and high product impurities, and achieves the improvement of product market competitiveness, high content, high color good effect

Inactive Publication Date: 2019-09-27
辽宁美亚制药有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 1. During the reaction process, the problem of oxidative degradation is prone to occur, resulting in the result of more impurities in the product
[0006] 2. Due to the existence of impurities and other reasons, the product has a high color grade, which is not conducive to subsequent production, research and utilization

Method used

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  • Preparation method for improving product quality of cefotaxime sodium
  • Preparation method for improving product quality of cefotaxime sodium
  • Preparation method for improving product quality of cefotaxime sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Add 400ml of chloroform to a dry and clean four-neck bottle, add 20g of 7-aminocephalosporanic acid, 5g of methanol, and 5g of pure water at a temperature controlled below 10°C, add DIPEA dropwise at a temperature controlled to pH7.0-9.0, and then statically separate layers , to separate the upper layer of organic impurities. Control the temperature below 20°C and add 26g of AE-active ester to condense for 2-5hr.

[0050] Then add 30ml of pure water for extraction, add 60ml of ethyl acetate to the aqueous phase and stir for 5-10min, then static and separate layers. Add 8.3 g of sodium isooctanoate / 120 ml of absolute ethanol to the aqueous phase, decolorize with activated carbon for 20 minutes and filter. The temperature of the filtrate was controlled below 30°C, 160ml of acetone was added, and the crystal was grown for 60min. After adding 500ml of acetone dropwise, wait until the crystals are completely precipitated. Filter, drain and then wash with acetone, drain and ...

Embodiment 2

[0053] Add 300ml of dichloromethane to a dry and clean four-neck bottle, add 20g of 7-aminocephalosporanic acid, 10g of ethanol, and 8g of pure water under temperature control below 10°C, add TEA dropwise under temperature control to pH7.0-9.0, and then statically separate layers , to separate the upper layer of organic impurities. Control the temperature below 20°C and add 27g of AE-active ester to condense for 2-5hr.

[0054] Then add 50ml of pure water for extraction, add 100ml of 2-methyltetrahydrofuran into the water phase, stir for 5-10min, and then separate the layers. Add 6.5 g of sodium acetate to the aqueous phase and stir for 10 min, decolorize with activated carbon for 15 min and filter. The temperature of the filtrate was controlled below 30°C, 280ml of acetone was added, and the crystal was grown for 60min. Add 850ml of acetone in the later stage until the crystals are completely precipitated. Filter, drain and then wash with acetone, drain and dry to obtain 2...

Embodiment 3

[0057] Add 200ml of carbon tetrachloride to a dry and clean four-necked bottle, add 20g of 7-aminocephalosporanic acid, 2.5g of ethanol, and 2.5g of pure water under temperature control below 10°C, and add ethylenediamine dropwise under temperature control to pH7.0-9.0 , and then static layered, separate the upper layer of organic impurities. Control the temperature below 20°C and add 28g of AE-active ester to condense for 2-5hr.

[0058] Then add 60ml of pure water for extraction, add 120ml of ethyl acetate to the aqueous phase and stir for 5-10min, then static and separate layers. Add 8.3 g of sodium isooctanoate / 120 ml of absolute ethanol to the water phase, decolorize with activated carbon for 15 minutes and filter. The temperature of the filtrate was controlled below 30°C, 325ml of acetone was added, and the crystal was grown for 60min. Add 900ml of acetone in the later stage until the crystals are completely precipitated. Filter, drain and then wash with acetone, drai...

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Abstract

The invention provides a preparation method for improving the product quality of cefotaxime sodium. The preparation method is characterized in that after pure water and organic alcohol are added into a reaction solvent, 7-aminocephalosporanic acid is dissolved under a neutral/slightly alkaline condition; then an impurity layer is separated; then a condensation reaction is performed with 2-(2-amino-4-thiazolyl)-2-methoxyiminoacetic to generate cefotaxime; a cefotaxime water solution obtained through extraction is directly added into an alcoholic solution of sodium acetate or sodium iso-octoate for a salt forming reaction without crystallization; decarbonization and sterile filtration are performed; then crystallization is performed by utilizing the solvent to obtain the target product cefotaxime sodium. The cefotaxime sodium prepared by the method provided by the invention is high in purity and good in yield.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of the antibacterial drug cefotaxime sodium, in particular to a preparation method for improving the product quality of cefotaxime sodium. Background technique [0002] The chemical name of cefotaxime sodium is (6R,7R)-3-[(acetoxy)methyl]-7-[(2-amino-4-thiazolyl)-(methoxyimino)acetamido] -Sodium 8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate. It is the third-generation cephalosporin antibiotic product for injection. [0003] At present, the technology of this variety is mainly 7-aminocephalosporanic acid and 2-methoxyimino-2-(2-amino-4-thiazolyl)-(z)-phenylhydrazolyl thioacetate in dichloromethane or 2 - in a solvent such as methyl tetrahydrofuran, then add solvents such as organic alcohols, use organic bases to catalyze the synthesis of cefotaxime acid, then extract carbon with water to remove and filter, add dilute acid dropwise to adjust the pH ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/06C07D501/12
CPCC07D501/06C07D501/12C07D501/34
Inventor 张岩沈东奇冯程
Owner 辽宁美亚制药有限公司
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