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Preparation method of cefdinir

A technology of cefdinir and cephalosporin, applied in the field of medicine, can solve the problems of low content, high energy consumption, long reaction time, etc., and achieve the effects of improving product yield, improving quality, and having no toxic and side effects

Inactive Publication Date: 2012-06-27
ZHEJIANG GUOBANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction is carried out at a low temperature of -10°C, the reaction time is long (24 hours), the energy consumption is large, the yield is ≤70%, and the content is low (≤95%)

Method used

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  • Preparation method of cefdinir

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] In a 1000ml four-neck flask, add 170ml tetrahydrofuran, 100ml purified water, stir evenly, at a temperature of 16°C, add 20g (0.0884mol) 7-AVCA, 36g (0.0951mol) cefdinir active new ester, stir evenly, weigh 9.40 g (0.0929mol) of triethylamine was dissolved in 30ml of tetrahydrofuran, and the tetrahydrofuran solution of triethylamine was slowly added dropwise to the four-necked bottle for about 1.5 hours. Extract twice, and the aqueous phase is about 120ml of cefdiniridine solution.

[0035] Control the temperature at 25°C, add 100ml tetrahydrofuran to the prepared cefdinirate solution, and add 13.8g (0.2580mol) NH 4 Cl, then dropwise added 51% K 2 CO 3 Solution 27g, dropwise, add 40g (0.408mol) potassium acetate, with 20%H 2 SO 4 Control the pH to 8.0-8.2, stir for 1 hour, then lower the temperature to 0-5°C and stir for 1 hour, and filter to obtain 40.5 g of a wet product of potassium salt.

[0036] Control the temperature at 25°C, dissolve the prepared potassium ...

Embodiment 2

[0038] In a 1000ml four-necked flask, add 120ml tetrahydrofuran, 150ml purified water, stir evenly, at a temperature of 16°C, add 20g (0.0884mol) 7-AVCA, 36g (0.0951mol) cefdinir active new ester, stir evenly, weigh 14.40 g (0.117mol) of triethylamine was dissolved in 30ml of tetrahydrofuran, and the tetrahydrofuran solution of triethylamine was slowly added dropwise to the four-necked bottle for about 1.5 hours. Extract twice, and the aqueous phase is about 170ml of cefdiniridine solution.

[0039] Control the temperature at 15°C, add 150ml of acetone to the prepared cefdinirate solution, and add 13.8g (0.2580mol) of NH 4 Cl, then dropwise added 51% K 2 CO 3 Solution 27g, dropwise, add 70g (0.714mol) potassium acetate, with 20%H 2 SO 4 Control the pH to 8.0-8.2, stir for 1 hour, then lower the temperature to 0-5°C and stir for 1 hour, filter to obtain 38.7 g of a wet product of potassium salt.

[0040] Control the temperature at 25°C, dissolve the prepared potassium salt...

Embodiment 3

[0042] In a 1000ml four-neck flask, add 170ml tetrahydrofuran, 100ml purified water, stir evenly, at a temperature of 16°C, add 20g (0.0884mol) 7-AVCA, 36g (0.0951mol) cefdinir active new ester, stir evenly, weigh 11.16 g (0.0976mol) of triethylamine was dissolved in 30ml of tetrahydrofuran, and the tetrahydrofuran solution of triethylamine was slowly added dropwise to the four-necked bottle for about 1.5 hours. Extract twice, and the aqueous phase is about 120ml of cefdiniridine solution.

[0043] Control the temperature at 25°C, add 40ml of tetrahydrofuran to the prepared cefdinirate solution, and add 13.8g (0.2580mol) of NH 4 Cl, then dropwise added 51% K 2 CO 3 Solution 27g, dropwise, add 10g (0.102mol) potassium acetate, with 20%H 2 SO 4 Control the pH to 8.0-8.2, stir for 1 hour, then lower the temperature to 0-5°C and stir for 1 hour, filter to obtain 39.8 g of a wet product of potassium salt.

[0044] Control the temperature at 25°C, dissolve the obtained potassiu...

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Abstract

The invention relates to a preparation method of cefdinir. According to the invention, under the effect of triethylamine, 7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-alkene-2carboxylic acid is subject to a reaction with (Z)-2-(2-aminothiazole-4-group)-2-acetyl oxyimino thioacetic acid(S-2-benzothiazole), such that a cefdinir ester liquid is obtained; the cefdinir ester liquid is extracted; an organic solvent is added to the cefdinir ester liquid; acetyl is removed by alkaline hydrolysis; sylvite of a weak acid is added to the liquid, the pH value is controlled, such that cefdinir sylvite is obtained; the sylvite is dissolved by using water; an organic solvent is added to the solution; the pH value is regulated, such that cefdinir is obtained. With the method, yield and quality are substantially improved; crystal form of the product is stable; and the method is suitable for industrialized productions.

Description

technical field [0001] The invention relates to a preparation method of cefdinir, which belongs to the technical field of medicine. Background technique [0002] Cefdinir, the chemical name is (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetamido]-8-oxo-3- Vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, the molecular formula is C14H13N5O5S2, the molecular weight is 395.42, and the structural formula is: [0003] [0004] Cefdinir is the third-generation broad-spectrum oral cephalosporin, which is effective against most Gram-positive bacteria and Gram-negative bacteria, especially Staphylococcus and Streptococcus among Gram-positive bacteria. Oral cephalosporins have stronger antibacterial activity. It is stable to β-lactamase produced by most bacteria, and has excellent antibacterial activity against β-lactamase-producing bacteria. Clinically, it is mainly suitable for the treatment of acute exacerbation of chronic bronchitis, bacterial pneumonia,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/22C07D501/04C07D501/12
Inventor 邱家军侯仲轲魏本涛王宗利吕秋波刘磊施颖峰潘伯安肖秋霞
Owner ZHEJIANG GUOBANG PHARMA
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