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Method for preparing cefdinir

A technology for cefdinir and cefdinir active ester, which is applied in the field of preparation of cefdinir, can solve problems such as difficulty in obtaining raw materials, reduce product yield, prolong production cycle, etc., and achieve shortening production cycle, improving yield and saving The effect of the solvent

Inactive Publication Date: 2011-08-17
GUANGDONG LIGUO PHARMACY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The disadvantages of this method are: the raw materials are not easy to obtain, the product yield is low, the preparation process needs chromatographic separation and freeze-drying, and the process is complicated
[0009] The shortcoming of this method is: need to use strong base when cefdinirate intermediate is hydrolyzed into cefdinir, require low temperature simultaneously, equipment burden is heavy, and reaction system is strong base system during strong base hydrolysis, easily causes reaction product degradation and other The generation of impurities is not conducive to product quality; at the same time, the intermediate of cefdinir needs to be separated, which prolongs the production cycle and reduces the product yield

Method used

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  • Method for preparing cefdinir
  • Method for preparing cefdinir

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Add 180mL of purified water, 20.0g of 7-AVCA and 36g of cefdinir active ester (acetoxyimide) into a 500mL four-necked reaction flask, add 140mL of tetrahydrofuran under stirring, cool down to 0°C, add 16mL of triethylamine, and heat up to 20°C, stirred and reacted for 9 hours, sampled and detected by HPLC that the residual amount of 7-AVCA was less than 1.0%, then added 120mL dichloromethane to the reaction solution, stirred for 30 minutes and then stood still for 30 minutes, separated into layers, and the lower dichloromethane phase was reused Extract with 50mL of purified water, stir for 30 minutes, let stand for 30 minutes, separate layers, recover the organic solvent from the lower dichloromethane phase, combine the upper water phase and add 80mL of dichloromethane to wash, stir for 30 minutes, let stand for 30 minutes, and separate layers , the lower dichloromethane phase is used for organic solvent recovery, 2g of activated carbon is added to the upper water phase,...

Embodiment 2

[0035] Add 180mL of purified water, 20.0g7-AVCA and 36g of cefdinir active ester (acetoxyimide) into a 500mL four-necked reaction flask, add 160mL of acetone under stirring, cool to 0°C, add 17mL of triethylamine, and heat up to 20°C, stirred and reacted for 11 hours, sampled by HPLC to detect that the residual amount of 7-AVCA was less than 1.0%, then added 120mL of dichloromethane to the reaction solution, stirred for 30 minutes and then stood still for 30 minutes, separated into layers, and the lower dichloromethane phase was reused Extract with 50mL of purified water, stir for 30 minutes, let stand for 30 minutes, separate layers, recover the organic solvent from the lower dichloromethane phase, combine the upper water phase and add 80mL of dichloromethane to wash, stir for 30 minutes, let stand for 30 minutes, and separate layers , the lower dichloromethane phase is used for organic solvent recovery, 2g of activated carbon is added to the upper water phase, stirred and dec...

Embodiment 3

[0038] Add 180mL of purified water, 20.0g7-AVCA and 36g of cefdinir active ester (acetoxyimide) into a 500mL four-necked reaction flask, add 160mL of ethanol under stirring, cool down to 0°C, add 16mL of triethylamine, and heat up to 20°C, stirred and reacted for 10 hours, sampled and detected by HPLC that the residual amount of 7-AVCA was less than 1.0%, then added 120mL dichloromethane to the reaction solution, stirred for 30 minutes and then stood still for 30 minutes, separated into layers, and the lower dichloromethane phase was reused Extract with 50mL of purified water, stir for 30 minutes, let stand for 30 minutes, separate layers, recover the organic solvent from the lower dichloromethane phase, combine the upper water phase and add 80mL of dichloromethane to wash, stir for 30 minutes, let stand for 30 minutes, and separate layers , the lower dichloromethane phase is used for organic solvent recovery, 2g of activated carbon is added to the upper water phase, stirred an...

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Abstract

The invention discloses a method for preparing cefdinir. The method comprises the following steps of: generating a cefdinir ester intermediate by 7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo [4.2.0] octy-2-alkene-2-carboxylic acid (7-AVCA) and cefdinir active ester (acetoxy imide) in the presence of organic base, and hydrolyzing the cefdinir ester intermediate by using immobilized carboxylic ester hydrolase to generate the cefdinir. In the method for preparing the cefdinir, the reaction condition is mild, an ultralow temperature reaction is avoided, process steps are reduced, and organic solvent is saved; and due to the adoption of enzyme hydrolysis, the reaction is easy to control, and yield is high, so the method is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of chemical pharmacy, in particular to a preparation method of cefdinir. Background technique [0002] Cefdinir is the third-generation oral cephalosporin antibiotic developed by Fujisawa Pharmaceutical Co., Ltd. in Japan in October 1991 to overcome the weak antibacterial effect of Cefixime on Staphylococcus aureus. Listed, showing a broad-spectrum antibacterial effect, especially for Gram-positive bacteria such as Staphylococcus aureus, Streptococcus, and Pneumococcus, showing good antibacterial ability. Cefdinir is stable to β-lactamase, and its chemical structure is characterized by the introduction of aminothiazolyl and hydroxylimine groups on the 7-position side chain of the 7-aminocephalosporanic acid skeleton, and the introduction of up vinyl. Clinically, cefdinir is mainly used for the treatment of acute exacerbation of chronic bronchitis, bacterial pneumonia, upper respiratory tract infection, skin and soft...

Claims

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Application Information

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IPC IPC(8): C07D501/22C07D501/06
Inventor 潘行远曾建江曾良兵楼秋霞黄剑锋
Owner GUANGDONG LIGUO PHARMACY
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