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Method for synthesizing cefuroxime axetil dimer

A technology of furoxetin axetil dimer and cefuroxime, which is applied in the field of synthesis of cefuroxime axetil dimer, can solve the problems of difficulty in establishing quality control methods, difficulty in obtaining impurity reference substances, and low impurity content, etc. To achieve the effect of ensuring the safety of clinical application

Inactive Publication Date: 2020-10-02
JIANGSU QINGJIANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] This isomer is a polymer impurity produced in the production process. Cefuroxime axetil itself consists of two chiral isomers, and the dimer obtained after dimerization and condensation contains three chiral isomers. At the same time, due to the The impurity content is low, and it is difficult to obtain the reference substance of this impurity through separation and purification. At present, there is basically no supply of this impurity at home and abroad, which brings certain difficulties to the establishment of quality control methods.

Method used

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  • Method for synthesizing cefuroxime axetil dimer
  • Method for synthesizing cefuroxime axetil dimer
  • Method for synthesizing cefuroxime axetil dimer

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Add paraldehyde (158.6g, 1.2mol) and tetrahydrofuran (500ml) into the reaction flask, add trimethylbromosilane (183.7g, 1.2mol) dropwise, after the addition is complete, stir and heat to reflux for 5 hours; to room temperature, add triethylamine (100ml) and cefuroxime (42.4g, 1.0mol), then raise the temperature to reflux, stir the reaction for 2-12h, cool to room temperature, concentrate under reduced pressure, successively use 10% sodium sulfite solution, 10% Wash with sodium carbonate solution and purified water, dry over anhydrous sodium sulfate, and concentrate at 35-40°C to obtain a yellow oil. Recrystallization from acetone gave 68.8 g of cefuroxime axetil dimer, with a yield of 75%.

Embodiment 2

[0019] Add paraldehyde (79.3g, 0.6mol) and diethyl ether (500ml) into the reaction flask, add trimethylbromosilane (91.8g, 0.6mol) dropwise, after the addition is complete, stir and heat to reflux for 6 hours; To room temperature, add triethylamine (50ml) and cefuroxime (21.2g, 0.5mol), then raise the temperature to reflux, stir and react for 8h, cool to room temperature, concentrate under reduced pressure, use 10% sodium sulfite solution, 10% sodium carbonate successively The solution was washed with purified water, dried over anhydrous sodium sulfate, and concentrated at 25-40°C to obtain a yellow oil. Recrystallization from acetone gave 30.95 g of cefuroxime axetil dimer, with a yield of 67.5%.

Embodiment 3

[0021] Add paraldehyde (79.3g, 0.6mol) and tetrahydrofuran (500ml) into the reaction flask, add trimethylbromosilane (91.8g, 0.6mol) dropwise, after the addition is complete, stir and heat to reflux for 5 hours; To room temperature, add potassium carbonate (150g) and cefuroxime (21.2g, 0.5mol), then raise the temperature to reflux, stir and react for 10h, cool to room temperature, concentrate under reduced pressure, use 10% sodium sulfite solution, 10% sodium carbonate solution successively , washed with purified water, dried over anhydrous sodium sulfate, and concentrated at 25-40°C to obtain a yellow oil. Recrystallization from acetone gave 26.3 g of cefuroxime axetil dimer, with a yield of 57.4%.

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Abstract

The invention discloses a method for synthesizing a cefuroxime axetil dimer, wherein the synthetic route comprises the steps: performing esterification condensation on cefuroxime serving as an initialraw material, paracetaldehyde and trimethylbromosilane to obtain the cefuroxime axetil dimer. The method has the advantages of simplicity in operation, mild reaction conditions, high yield, pure product and the like, and is suitable for synthesizing the cefuroxime axetil dimer.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for synthesizing cefuroxime axetil dimer. Background technique [0002] Cefuroxime axetil is the prodrug of cefuroxime (API), which belongs to the semi-synthetic second-generation broad-spectrum cephalosporins. It is a cephalosporin antibiotic developed by GlaxoSmithKline (GSK) in the UK. The product has a wide antibacterial spectrum, is effective against a variety of Gram-positive and Gram-negative bacteria, and is stable against β-lactamase. Because of its definite curative effect, low renal toxicity and small side effects, it is widely used to fight against sensitive bacteria. of various infections. Its antibacterial mechanism is to inhibit the synthesis of bacterial cell walls by binding to bacterial proteins, causing defects in the destruction of bacterial cell walls, leakage of substances in the bacteria, and death of the bacteria. Clinical use of cefuroxime axetil ...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07D501/34C07D501/04
CPCC07D519/00C07D501/34C07D501/04
Inventor 隽海龙王崇益
Owner JIANGSU QINGJIANG PHARMA
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