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Preparation method of cefmenoxime hydrochloride

A technology of cefmenoxime hydrochloride and hydrochloride, which is applied in the field of medicine and chemical industry, can solve the problems of high cost, low product purity and yield, and increased cost, and achieve the effects of less pollution, improved color, and reduced degradation

Active Publication Date: 2018-08-10
山东四环药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The used raw material triphenylchloromethane and p-toluenesulfonyl chloride of this method are all more expensive, can make cost increase a lot in industrialized production process, and gained product purity and productive rate are all lower

Method used

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  • Preparation method of cefmenoxime hydrochloride
  • Preparation method of cefmenoxime hydrochloride
  • Preparation method of cefmenoxime hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] (1) Under stirring, add 100.0g (0.5mol) of aminothiaxamic acid to 1000ml of dichloromethane, then add 106.0g (0.52mol) of N,O-bis(trimethylsilyl)acetamide dropwise, and add it in about 0.5h. , Then heat to 40℃;

[0045] (2) Add 227.7g (2.25mol) of triethylamine dropwise to the solution of the compound of formula III, dropwise add 62.0g (0.52mol) of thionyl chloride, add it in about 0.5h, control the temperature at 0℃ and react for 2h, then cool to At -17~-13°C, add 174.2g (0.47mol) of 7-ATCA.HCl, react at this temperature for 2h, and monitor the reaction with 7-ATCA.HCl≤1.0%. After the reaction is completed, add 1000 ml of water, adjust the pH value to 6-7 with 35% hydrochloric acid solution, stir to separate the liquids, and retain the aqueous phase; the organic phase is extracted with 500 ml and 300 ml of water successively, and the aqueous phases are combined.

[0046] (3) Add 25 g of activated carbon and 25 g of alumina to the combined water phase to decolorize for 0.5 ...

Embodiment 2

[0048] (1) Add 100.0g (0.5mol) of axamic acid to 1000ml of dichloromethane while stirring, then add 84.0g (0.52mol) of hexamethyldisilazane dropwise, add it in about 0.5h, and then heat to 45°C, After stirring for 4 hours, it was cooled to 2°C, and the solution of the compound of formula III was directly used in the next reaction.

[0049] (2) Add 258.5g (2.0mol) of N,N-diisopropylethylamine, 62.7g (0.52mol) of pivaloyl chloride dropwise to the solution of the compound of formula III, add it in about 0.5h, and control the temperature at 2℃ React for 3h, then cool to -19~-15°C, add 166.0g (0.45mol) of 7-ATCA.HCl, react at this temperature for 3h, reaction monitoring 7-ATCA.HCl≤1.0%. After the reaction is completed, add 1000 ml of water, adjust the pH to 6-7 with 35% hydrochloric acid solution, stir and separate the liquids, and retain the aqueous phase; the organic phase is extracted with 500 ml and 400 ml of water in turn, and the aqueous phases are combined.

[0050] (3) Add 12.5...

Embodiment 3

[0052] (1) Under stirring, add 100.0g (0.5mol) of the axamic acid of formula II into a mixed solvent of 900ml of dichloromethane and 100ml of N,N-dimethylformamide (DMF), and then add dropwise hexamethyldisilazane After adding 82.3g (0.51mol) in about 0.5h, it was heated to 42°C, stirred for 2h, and then cooled to 2°C. The solution of the compound of formula III was directly used in the next reaction.

[0053] (2) Add 258.5g (2.0mol) of N,N-diisopropylethylamine dropwise to the solution of the compound of formula III, add 59.5g (0.50mol) of thionyl chloride dropwise, and finish adding in about 0.5h, control the temperature to 0 React at ℃ for 2h, then cool to -17~-13℃, add 174.2g (0.47mol) of 7-ATCA.HCl, react at this temperature for 2h, and monitor the reaction with 7-ATCA.HCl≤1.0%. After the reaction is completed, add 1000 ml of water, adjust the pH value to 6-7 with 35% hydrochloric acid solution, stir to separate the liquids, and retain the aqueous phase; the organic phase is...

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PUM

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Abstract

The invention discloses a preparation method of cefmenoxime hydrochloride. The method includes the steps: performing trimethylsilyl protection on methoxyiminoacetic acid; performing carboxyl activation by the aid of activating reagents; performing reaction with 7-ATCA hydrochloride; performing acidification by the aid of hydrochloric acid, growing the grain in a cooling manner to obtain the cefmenoxime hydrochloride. The purity of the cefmenoxime hydrochloride prepared by the method is higher than 99.5%, and the mole yield of products is 88% or more. According to the method, raw materials arecheap and easy to obtain, the purity of the products is high, yield is high, and industrial production can be achieved.

Description

Technical field [0001] The invention belongs to the field of medicine and chemical industry, and specifically relates to a preparation method of antibiotic medicine cefmenoxime hydrochloride. Background technique [0002] Cefmenoxime hydrochloride belongs to the third-generation semi-synthetic cephalosporin antibiotic. It has better antibacterial effect than cefotaxime and cefoperazone. It is widely used in the treatment of bacterial infections such as gram-positive and negative bacteria. In addition, hydrochloric acid Cefmenoxime has a strong antibacterial effect on Proteus, Serratia marcescens, Haemophilus influenzae, and Enterobacter. It also has a strong antibacterial and bactericidal effect against peptococcus, peptostreptococcus, etc. It can be used for sepsis, respiratory tract infections, liver and gallbladder infections, meningitis, empyema, peritonitis, reproductive system infections, urinary tract infections and burns caused by sensitive bacteria. Surgical wound infec...

Claims

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Application Information

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IPC IPC(8): C07D501/02C07D501/36
CPCC07D501/02C07D501/36
Inventor 张晓君李刚熊自常郭建军刘慧敏徐春海
Owner 山东四环药业股份有限公司
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