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Preparation method of cefotetan

A technology of cefotetan and intermediates, applied in the direction of organic chemistry, etc., can solve the problems of high quality, low product yield, high production cost, etc.

Inactive Publication Date: 2013-10-16
HAINAN HERUI PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The overall reaction control of the second step is difficult, not suitable for large-scale industrial production, and its yield is lower than the first process, and the quality is not as high as the first process
In the process of researching the first process route, the inventors found that the reaction conditions of the first process route had many deficiencies, such as not only high production cost, extremely complicated operation, but also the darker color of the product made, the product low yield

Method used

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  • Preparation method of cefotetan

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0098] 1) Preparation of intermediate CefoD-1

[0099] Add the organic solvents dichloromethane and 7-MAC into the cleaned and dried glass-lined reaction tank, stir and cool to -20°C, and slowly add the alkaline reagent pyridine dropwise for about 15 minutes. Cool to -25°C, add chloroacetyl chloride dropwise, and complete the addition in about 10 to 20 minutes, and control the temperature during the dropwise addition to not exceed -15°C. Insulate and stir for 15 minutes, then take a sample and send it for inspection (7-MAC≤2.0%, if the reaction is not complete, extend the reaction time until the reaction is complete).

[0100] Add purified water, sodium chloride, and concentrated hydrochloric acid into a glass-lined reaction tank, and stir until completely dissolved. Transfer the solution into a glass-lined reaction tank that has been completely reacted. During the transfer process, the temperature should not exceed 5°C. layer, and the upper water phase is sent to the sewage...

Embodiment 2

[0130] 1) Preparation of intermediate CefoD-1

[0131] The process includes reaction, hydrolysis, decolorization and crystallization, in which:

[0132] The reaction described is: add 7.52kg of organic solvents dichloromethane and 1kg of 7-MAC into the reaction tank, stir and cool to -20°C, slowly add 0.2kg of alkaline reagent pyridine dropwise, after 15 minutes, cool to -25°C and then Add 0.25 kg of chloroacetyl chloride dropwise, and finish adding in 10-20 minutes. During the dropping process, control the temperature not to exceed -15°C, keep warm and stir for 15 minutes, and send samples for inspection. If 7-MAC≤2.0%, the reaction is complete; if 7-MAC> 2.0%, the reaction is not complete, prolong the reaction time until the reaction is complete.

[0133] After the reaction is complete, carry out hydrolysis, decolorization and crystallization.

[0134] Described hydrolysis comprises the steps:

[0135] (i) Add purified water, sodium chloride and concentrated hydrochloric ...

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Abstract

The invention relates to a preparation method of cefotetan. The method comprises the steps of: under an alkaline condition, reacting the starting raw material 7-MAC with chloroacetyl chloride in an organic solvent so as to obtain the intermediate CefoD-1; under nitrogen protection, adding aluminium trichloride into anisole, stirring for dissolving, and leaving the obtained solution for standby application; taking another organic solvent, into which the intermediate CefoD-1 is added under stirring, then adding the standby solution for reacting, thus obtaining the intermediate CefoD-2; reactingthe intermediate CefoD-2 with 3, 5-dithiol-4-isothiazole formic acid trisodium salt until that a sampled cefotetan tautomer is detected less than 4.0%, after the reaction conducting a post-treatment,thus obtaining cefotetan. With improved yield and reduced cost, the method of the invention, without final heating concentration, can generate products with a shallow color and almost invariant purity.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to provide a preparation method of cefotetan, an antibacterial drug. Background technique [0002] Cefotetan is an important antibiotic, which was first developed by Fujisawa Company in Japan and first listed in Japan in the late 1980s. Astra Company obtained the marketing right of this product outside Japan. Cefotetan’s The injection was approved to go on the market in the United States in 2003, under the trade name CEFOZAN. It has been used for many years in the treatment of gram-negative infections resistant to more common antibiotics and has the following chemical structure: [0003] [0004] Cefotetan (Cefotetan) is a cephamycin antibiotic synthesized from methylthiotetrazolium cephalexin and aminocarboxyethylene dithiabutanecarboxylate. It is a semi-synthetic broad-spectrum cephalosporin. The effect on Gram-negative bacteria is stronger than that of the first and second...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/57C07D501/04C07D501/12
Inventor 朱正兵张稳稳
Owner HAINAN HERUI PHARMA
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