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Method for preparing cefmenoxine hydrochloride raw material

A technology of cefmenoxime hydrochloride and raw materials, applied in the field of preparation of cefmenoxime hydrochloride, can solve problems such as poor solubility, endangering life safety, shock, death and the like

Active Publication Date: 2016-11-16
ZHEJIANG WHITESON PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Cefmenoxime hydrochloride has poor solubility and is slightly soluble in water, glucose, sodium chloride and other solutions. Sodium carbonate, a co-solvent, is added to the preparation, but the solubility is still very poor. It is difficult to dissolve in clinical application and generally takes 10-20 minutes to dissolve. completely dissolved
This increases the amount of degraded impurities during the dissolution process, forming polymer impurities, and increasing clinical allergic reactions. Severe cases can cause shock and death, directly threatening the lives of patients; and incompletely dissolved particles can form thrombus after entering the human body. Severe cases may endanger human life

Method used

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  • Method for preparing cefmenoxine hydrochloride raw material
  • Method for preparing cefmenoxine hydrochloride raw material
  • Method for preparing cefmenoxine hydrochloride raw material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Take 100g of 7-amino-3-[1-methyl-1H-tetrazole-5-thiomethyl]-ceph-3-ene-4-carboxylic acid (7-ACT), 1000ml of dichloromethane, and cool in an ice-water bath To about 5°C, add 120g of AE active ester, then add 100ml of triethylamine, continue to stir for 4 hours, extract twice with 500ml of water, combine the water phase, add 10g of activated carbon, stir for 30 minutes to decolorize, filter with suction, and wash with 200ml of water Carbon cake, combined water phase. The filtrate was adjusted to pH 2.5 with 10% hydrochloric acid, and a white solid was precipitated, stirred and grown for 3 hours, and filtered. Wash twice with 500ml ethanol and drain. Dry under reduced pressure at a temperature lower than 40°C for 10 hours until the water content is lower than 1.0%, to obtain 82.5 g of crude cefmenoxime hydrochloride.

[0022] Step 2: Take 50g of crude cefmenoxime hydrochloride, add 200mL of water for injection, add 5g of L-glutamic acid, heat up to 38°C, add 1g of dietha...

Embodiment 2

[0024] Take 100g of 7-amino-3-[1-methyl-1H-tetrazole-5-thiomethyl]-ceph-3-ene-4-carboxylic acid (7-ACT), 1000ml of dichloromethane, and cool in an ice-water bath At about 5°C, add 120g of AE active ester, then add 100ml of triethylamine, continue to stir for 4 hours, extract twice with 500ml of water, combine the water phase, add 10g of activated carbon, stir for 30 minutes to decolorize, filter with suction, and wash with 200ml of water Carbon cake, combined water phase. The filtrate was adjusted to pH 2.5 with 10% hydrochloric acid, and a white solid was precipitated, stirred and grown for 3 hours, and filtered. Wash twice with 500ml ethanol and drain. Dry under reduced pressure at a temperature lower than 40°C until the water content is lower than 1.0%, to obtain 83.2 g of crude cefmenoxime hydrochloride.

[0025] Step 2: Take 50g of cefmenoxime hydrochloride crude product, add 200mL of water for injection, add 5g of L-glutamic acid, heat up to 35°C, add 1g of diethanolam...

Embodiment 3

[0027] Take 100g of 7-amino-3-[1-methyl-1H-tetrazole-5-thiomethyl]-ceph-3-ene-4-carboxylic acid (7-ACT), 1000ml of dichloromethane, and cool in an ice-water bath At about 5°C, add 120g of AE active ester, then add 100ml of triethylamine, continue to stir for 4 hours, extract twice with 500ml of water, combine the water phase, add 10g of activated carbon, stir for 30 minutes to decolorize, filter with suction, and wash the carbon with 200ml of water cake, and combine the aqueous phases. The filtrate was adjusted to pH 2.5 with 10% hydrochloric acid, and a white solid was precipitated, stirred and grown for 3 hours, and filtered. Wash twice with 500ml ethanol and drain. Dry under reduced pressure at a temperature lower than 40°C until the water content is lower than 1.0%, to obtain 82.1 g of crude cefmenoxime hydrochloride.

[0028] Step 2: Take 50g of crude cefmenoxime hydrochloride, add 200mL of water for injection, add 5g of L-glutamic acid, heat up to 38°C, add 1g of dieth...

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Abstract

The invention belongs to the technical field of medicines, and discloses a method for preparing a cefmenoxine hydrochloride raw material. The method comprises the following steps: enabling 7-ACT as a raw material to react with AE active ester, and adjusting with hydrochloric acid so as to generate a crude product of cefmenoxine hydrochloride; adding L-glutamic acid at normal temperature, heating, adding diethanol amine, cooling, and adding ethyl acetate, thereby obtaining a novel cefmenoxine hydrochloride raw material. By adopting the method disclosed by the invention, the content of macromolecule impurities in cefmenoxine hydrochloride is smaller than 0.1%, and the cefmenoxine hydrochloride raw material can be completely dissolved within 5 seconds.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a preparation method of cefmenoxime hydrochloride which is easily soluble and has low content of high-molecular impurities. Background technique [0002] Cefmenoxime Hydrochloride (Cefmenoxime Hydrochloride), chemical name: (6R, 7R)–7–[(Z)-2–(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3 -[[(1-Methyl-1H-tetrazol-5-yl)-thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene -2-Formic acid hydrochloride (2:1). Its chemical structural formula is as follows: [0003] [0004] Cefmenoxime hydrochloride is a semi-synthetic broad-spectrum antibiotic developed and produced by Japan's Takeda Pharmaceutical Co., Ltd. It entered the Chinese market in 1996. [0005] This product is a third-generation semi-synthetic cephalosporin broad-spectrum antibiotic, which achieves bactericidal effect by inhibiting the biosynthesis of bacterial cell walls. This product has a strong...

Claims

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Application Information

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IPC IPC(8): C07D501/36
CPCC07D501/36
Inventor 芦红代
Owner ZHEJIANG WHITESON PHARMA
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