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Method for preparing cefixime compound

A technology of cefixime and cefixime methyl ester, which is applied in the field of preparation of cefixime compounds, can solve the problems of harsh reaction conditions, expensive solvents, unfavorable continuity, etc., and achieve increased product yield, increased yield and Purity, the effect of shortening the production cycle

Inactive Publication Date: 2013-12-25
TIANJIN UNIVERSITY OF TECHNOLOGY
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Problems solved by technology

[0010] It can be seen from the above preparation method that THF is used in this process, and the solvent is expensive and difficult to recover, and the mother liquor after crystallization and centrifugation of cefixime methyl ester (MFCEF) will take away part of the material, affecting the yield; Synthesis of cefixime methyl ester (MFFCEF) will generate a by-product 2-mercaptobenzothiazole, which has good solubility in tetrahydrofuran, and can be partially dissolved in the water phase during extraction, which has a certain impact on the yield of subsequent products and the quality of finished products. In addition, the process has harsh reaction conditions and long reaction time, which is not conducive to continuous and large-scale process production

Method used

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  • Method for preparing cefixime compound
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  • Method for preparing cefixime compound

Examples

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Effect test

Embodiment 1

[0032] A preparation method of cefixime compound, the steps are as follows:

[0033] 1) In a 1000mL four-neck flask, add 300mL of dichloromethane, 45mL of ethanol, and 15mL of purified water, stir and cool down to 0-2°C, add 50g of 7-AVCA, 100g of MICA active ester, and slowly add triethylamine dropwise at 5°C It takes about 0.5 hours for 25g of amine, and the temperature is raised to 5-10°C after the addition is completed, and the reaction is carried out under this condition for 5 hours, the pH is controlled at 7.5-8.0, and the reaction is stopped when 7-AVCA<0.5wt% in the reaction solution is detected by HPLC. A solution of cefixime methyl ester was prepared.

[0034] 2) Add 150mL of purified water to the above cefixime methyl ester solution, stir for 10 minutes, let stand to separate the water phase, extract the organic phase twice with 150mL of pure water, combine the water phase, add 1g hydrosulfite, 1g ethylenediamine Tetraacetic acid and 5g activated carbon were decolo...

Embodiment 2

[0039] A kind of preparation method step of cefixime compound is as follows:

[0040] 1) In a 1000mL four-neck bottle, add 350mL of chloroform, 60mL of methanol, and 25mL of purified water, stir and cool down to 0-5°C, add 50g of 7-AVCA, 120g of MICA active ester, and slowly add 28g of triethylamine dropwise at 5°C After about 1 hour, the dropwise addition was completed and the temperature was raised to 8-12°C. Under this condition, the reaction was carried out for 5.5 hours, and the pH was controlled at 7.5-8.0. The reaction was stopped by detecting 7-AVCA<0.5% in the reaction solution by HPLC, and Cefixime A was obtained. ester solution.

[0041] 2) Add 200 mL of purified water to the above cefixime methyl ester solution, stir for 10 minutes, and let stand to separate the water phase. The organic phase was extracted twice with 100 mL of purified water, the aqueous phase was combined, 0.5 g of hydrosulfite and 0.5 g of ethylenediaminetetraacetic acid were added, 2.5 g of act...

Embodiment 3

[0045] A preparation method of cefixime compound, the steps are as follows:

[0046] 1) In a 1000mL four-necked bottle, add 300mL of ethyl acetate, 50mL of methanol, and 30mL of purified water, stir and cool down to 5-8°C, add 50g of 7-AVCA, 125g of MICA active ester, and slowly add 25g of cyclohexylamine dropwise at 5°C After about 0.5 hours, the dropwise addition was completed and the temperature was raised to 10-15°C. Under this condition, the reaction was carried out for 6 hours, and the pH was controlled at 8.0-8.5. The 7-AVCA<0.5% in the reaction solution was detected by HPLC to stop the reaction, and Cefixime A was obtained. ester solution.

[0047] 2) After the reaction, add 150 mL of purified water, stir for 10 minutes, and let stand to separate the water phase. The organic phase was extracted twice with 150 mL of pure water, the aqueous phase was combined, 1.5 g of hydrosulfite and 1.5 g of ethylenediaminetetraacetic acid were added, 5 g of activated carbon was deco...

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Abstract

The invention provides a method for preparing a cefixime compound. According to the method for preparing the cefixime compound, 7-AVCA is used as a raw material, cefixime methyl ester is obtained through action of the 7-AVCA and MICA active ester by means of an acylation reaction on 7-amno of the 7-AVCA, the cefixime methyl ester is not separated, inorganic base hydrolysis and a refining reaction are directly conducted on the cefixime methy ester, and therefore cefixime is obtained. The method for preparing the cefixime compound has the advantages that original expensive reagents such as tetrahydrofuran difficult to recycle are replaced by an organic solvent, the organic solvent and water are immiscible, the reaction solvent is easy to recycle and reuse, the pollution to the environment is reduced, and the production cost is reduced; acylation and hydrolysis are integrated, operation is simplified, the production period is shortened, the yield and the purity are improved, and large-scale industrial production is facilitated.

Description

technical field [0001] The invention relates to medicine synthesis technology, in particular to a preparation method of cefixime compound. Background technique [0002] Cefixime is the third-generation oral cephalosporin, first developed and marketed by Fujisawa Pharmaceutical Co., Ltd., Japan, and approved by the US FDA in 1987. It has been widely clinically used in more than 80 countries, mainly for sensitive bacteria Respiratory tract infection, urinary tract infection, meningitis, ENT infection, biliary tract infection, pyelonephritis, etc. The cefixime compound has a broad antibacterial spectrum, and has good antibacterial activity against most Enterobacteriaceae bacteria such as Streptococcus pyogenes, Pneumococcus, Streptococcus agalactiae, Neisseria gonorrhoeae, Influenza bacilli, Morakata, Escherichia coli, and Klebsiella pneumoniae. The commonly used production process is to use 7-amino-3-vinyl-cephalosporanic acid (7-AVCA) to acylate the side chain acid active e...

Claims

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Application Information

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IPC IPC(8): C07D501/22C07D501/04C07D501/06
Inventor 刘金彪黄磊孙永跃
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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