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Preparation method of cefozopran hydrochloride

A technology of cefazolam hydrochloride and hydrochloric acid, applied in the field of pharmaceutical antibiotics, can solve the problems of unfavorable continuity, large-scale industrial production, low cefazolam yield, long reaction time, etc., and achieves elimination of discoloration phenomenon, excellent quality, The effect of low product loss

Inactive Publication Date: 2013-03-06
国药集团致君(苏州)制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In these known synthetic methods, adopting 7-ACA or 7-AACA as raw material to prepare cefozopram has low yield, poor quality, and long reaction time, which is unfavorable for continuous and large-scale industrial production

Method used

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  • Preparation method of cefozopran hydrochloride
  • Preparation method of cefozopran hydrochloride
  • Preparation method of cefozopran hydrochloride

Examples

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Embodiment 1

[0064] (1) GCLE12.5g, NaI4.1g, acetone 80ml at 30°C, stirred for 15 minutes. Then, 4.5 g of imidazopyridazine was added, the temperature was raised to 35° C., and the mixture was stirred for 5 hours. Add 125 ml of isopropanol, and stir for 30 minutes after addition. Cool down to 0° C., stir for 1 hour, filter, and wash the filter cake twice with a mixture of 50 ml of isopropanol and 30 ml of acetone. Drying in vacuo gave a yellow-green solid (GIMPE). Add 25 ml of phenol, raise the temperature to 50°C, and stir for 10 hours. Cool down to 40°C, add 10ml of isopropyl ether and 5ml of isopropanol mixture, and then stir for 20 minutes. The reaction solution was added to 60ml of isopropyl ether, and a yellow solid was precipitated. After stirring for 60 minutes, it was filtered, and the filter cake was washed with 30ml of acetone and 40ml of isopropyl ether. The filter cake was added into a mixture of 1.2 g of sodium bicarbonate, 45 ml of water, and 10 ml of acetone and stirred ...

Embodiment 2

[0067] (1) 13g of GCLE, 4.1g of NaI, 80ml of acetone were stirred at 30°C for 15 minutes. Then, 4.5 g of imidazopyridazine was added, the temperature was raised to 35° C., and the mixture was stirred for 7 hours. Add 130 ml of isopropanol, and stir for 30 minutes after addition. Cool down to 0° C., stir for 1 hour, filter, and wash the filter cake twice with 50 ml of isopropanol. Drying in vacuo gave a yellow-green solid (GIMPE). Add 25 ml of phenol, raise the temperature to 50°C, and stir for 10 hours. Cool down to 40°C, add 10ml of isopropyl ether and 5ml of isopropanol mixture, and then stir for 20 minutes. The reaction liquid was added into 60ml of isopropyl ether, and a yellow solid was precipitated. After stirring for 60 minutes, it was filtered, and the filter cake was mixed and washed with 40ml of isopropyl ether. The filter cake was added to a mixture of 1 g of sodium bicarbonate, 45 ml of water, and 10 ml of acetone and stirred to dissolve. Add 10ml of isopropyl...

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Abstract

The invention discloses a preparation and purification method of cefozopran hydrochloride. The method comprising the following steps of: with GCLE (7-phenylethyl amide-3-chloromethyl-3-cephem-4-carboxylic p-methoxybenzyl methyl) as a raw material, preparing cefozopran and hydrochlorinating to obtain cefozopran hydrochloride. The preparation method of the invention has simple preparation process, and comprises the following steps of: combining the extraction and the crystallization of the purification part by adopting a mixed solvent; and adding a water-soluble reducing agent in the easy discoloration step to obtain a finished product with high yield and good color. The cefozopran hydrochloride prepared by using the method of the invention reaches the total yield not lower than 65 percent.

Description

technical field [0001] The invention relates to the preparation of cefozopran, in particular to a method for preparing and purifying cefozopran hydrochloride, which belongs to the field of drug antibiotics. Background technique [0002] Cefozopran, chemical name 1-[[(6R,7R)-7-[[(2Z)-(5-amino-1,2,4-thiadiazol-3-yl)(methoxy Amino)acetyl]amino]-2-carboxylic acid-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]imidazol[1, 2-b] inner salt of pyridazine, its structural formula is shown in formula (1). [0003] [0004] Cefozopran is less stable, so it is in the form of cefozopran hydrochloride (Cefozopran hydrochloride) when it is prepared and used, and its structural formula is as shown in formula (1'). [0005] [0006] Cefazolam hydrochloride is the fourth-generation cephalosporin for injection developed by Japan's Takeda Pharmaceutical Company. Cefuzolam has a high affinity to penicillin 1 and protein 2 of Staphylococcus aureus and penicillin 3 of Escherichia col...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/06
CPCY02P20/55
Inventor 史利军孙元强
Owner 国药集团致君(苏州)制药有限公司
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