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Method for preparing cefmenoxime hydrochloride

A technology of cefmenoxime hydrochloride and hydrochloride, which is applied in the field of compound preparation, can solve the problems of low yield, complicated synthetic route, and high production cost, and achieve the effects of low color grade, high purity, and low cost

Inactive Publication Date: 2012-09-19
SHANDONG LUKANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, there are many documents about the synthetic route of cefmenoxime hydrochloride, such as: DE27132, US3262932, JP80-38349, JP84-53492, CN101555251A, etc., but all have the disadvantages of complicated synthetic route, low yield and high production cost

Method used

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  • Method for preparing cefmenoxime hydrochloride
  • Method for preparing cefmenoxime hydrochloride
  • Method for preparing cefmenoxime hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 260ml of dichloromethane, 5ml of ethanol and 35ml of isopropanol into a 500ml four-necked bottle, cool down to -7°C, add 20g of 7-ACT hydrochloride and 21g of active ester of compound AE represented by formula III in sequence, and dropwise add 20ml of triethylamine, After 20 minutes of dripping. At the end of the drop, keep warm at -3°C for 5 hours for condensation reaction. The endpoint was detected by high performance liquid chromatography. After the reaction was complete, 150 ml of anhydrous salt was added, and the layers were separated. The organic phase was extracted once more with 90 ml of anhydrous salt, the aqueous phases were combined, and the aqueous phase was back-extracted with dichloromethane. The pH value of the aqueous phase was adjusted to 6-7 with acid, and 1 g of activated carbon and 0.1 g of sodium bisulfite were added for decolorization for 20 min. Filter and wash the filter cake with 70ml of water. Another 1000ml four-necked bottle was instal...

Embodiment 2

[0029] Add 26L of dichloromethane, 5L of ethanol and 35L of isopropanol to a 50L reaction tank, cool down to -8°C, add 2kg of 7-ACT hydrochloride and 2.1kg of compound AE active ester represented by formula III in sequence, and add 2.0L of triethylamine dropwise , 20min after dripping. At the end of the dropping, keep warm at -4°C for 5 hours for condensation reaction. The endpoint was detected by high performance liquid chromatography. After the reaction was complete, 15 L of anhydrous salt was added, and the layers were separated. The organic phase was extracted once more with 9 L of anhydrous salt, the aqueous phases were combined, and the aqueous phase was back-extracted with dichloromethane. The pH value of the aqueous phase was adjusted to 6-7 with acid, and 0.12 kg of activated carbon and 0.012 kg of sodium bisulfite were added for decolorization for 20 minutes. Filter and wash the filter cake with 7L of water. Another 100L reaction tank was prepared, and 18L of acet...

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Abstract

The invention discloses a method for preparing cefmenoxime hydrochloride, which comprises the following steps: uniformly mixing 7-ACT hydrochloride shown in a formula II and AE active ester shown in a formula III under the condition that methylene dichloride and a solvent exist for condensation reaction and obtaining the cefmenoxime hydrochloride shown in a formula I after reaction. The method has the benefits that the cefmenoxime hydrochloride can be synthesized in one step, the cefmenoxime hydrochloride is not required to be separated, a reversely-dropping crystallization method is adopted, the synthetic line is short, the cost is low, the reaction conditions are wild, and the production is convenient; and the cefmenoxime hydrochloride product is high in yield and purity and low in color grade and has an important application value.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a method for preparing cefmenoxime hydrochloride. Background technique [0002] Cefmenoxime hydrochloride (cefmenoxime hydrochloride), the chemical name is (6R, 7R)-7-[2-(2-amino-4-thiazolyl)(methoxyimino)acetamido]-3-[[(1- Methyl-1H-tetrazol-5-yl)-thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Salt, its chemical structural formula is as shown in formula I. [0003] [0004] Formula I [0005] Cefmenoxime hydrochloride is a semi-synthetic broad-spectrum antibiotic developed and produced by Japan's Takeda Pharmaceutical Co., Ltd. It was launched in Japan in 1983 and entered the latest version of the Pharmacopoeia of the United States, Japan and other countries. It was launched in my country in 2000. [0006] Cefmenoxime hydrochloride is a third-generation cephalosporin, which has antibacterial effects on Gram-negative and positive aerobic and anaero...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/36C07D501/06C07D501/12
Inventor 翟昌梅王小丹
Owner SHANDONG LUKANG PHARMA
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