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Cefepime hydrochloride compound prepared by new synthetic method

A technology of cefepime hydrochloride and a synthesis method, which is applied in the directions of organic compound/hydride/coordination complex catalyst, chemical instrument and method, chemical/physical process, etc. , low yield, etc.

Inactive Publication Date: 2010-02-03
HAINAN LINGKANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have found that the use of solid resin will absorb a large amount of cefepime feed solution, which is not easy to wash and recover, resulting in a low yield
The recovery and reuse of solid resin will easily affect the product quality, because the cephalosporin feed liquid inside the resin is difficult to completely remove, and the cefepime feed liquid is easy to decompose at normal temperature, and the decomposition product will enter the feed liquid when it is used next time. unnecessary impurities
Moreover, the use of hydrochloric acid with a high concentration in production will volatilize strongly acidic hydrogen chloride gas, which will be adsorbed on the inner surface of the reaction equipment, causing corrosion to the equipment, not only reducing the service life of the production equipment, but also making the product mixed with insoluble particles. As a result, indicators such as clarity and heavy metals of the preparation do not meet the requirements of the Pharmacopoeia
[0008] The synthesis technology of cefepime hydrochloride is relatively difficult. Although there has been some progress in the research of its synthesis technology in China, the cost is high and the quality is not good.

Method used

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  • Cefepime hydrochloride compound prepared by new synthetic method
  • Cefepime hydrochloride compound prepared by new synthetic method
  • Cefepime hydrochloride compound prepared by new synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The synthesis of embodiment 12-(2-formylaminothiazol-4-yl)-2-methoxyimine acetic acid

[0036] Add 201 g of 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid into 2L of formic acid, and at the same time add 30 g of 4A molecular sieve as a catalyst, heat up to 60 ° C for 4 hours, and distill under reduced pressure to remove most of the Formic acid, add 1L of water, stir, extract with 500ml of ethyl acetate, dry over anhydrous sodium sulfate, concentrate under reduced pressure to get 2-(2-formylaminothiazol-4-yl)-2-methoxyiminoacetic acid 217g, yield 95%.

Embodiment 2

[0037] The synthesis of embodiment 2 cefepime hydrochloride

[0038] 100g of 2-(2-formylaminothiazol-4-yl)-2-methoxyimine acetic acid and 80ml of N,N-diisopropylethylamine were added to 400ml of N,N-dimethylformaldehyde In the amide, cool the reactant to 10°C, add 86g (0.45mol) p-toluenesulfonyl chloride, keep this temperature and stir for 1 hour, then add 187g (0.44mol) 7-MPYCA and 260ml triethylamine, in 5-10 Stir vigorously at ℃ for 30 minutes, then add 4L of acetone and stir to precipitate a solid, filter, wash with 1L of acetone or dichloromethane, and dry under vacuum at 40°C to obtain 223.6 g of cefepime hydrochloride, with a yield of 94%.

[0039] Product Structural Characterization

[0040] 1. Melting point: 150°C.

[0041] 2. Elemental analysis:

[0042] Theoretical value C: 39.9%, H: 4.9%, O: 16.8%, Cl: 12.4%, N: 14.7%, S: 11.2%

[0043] Found C: 39.3%, H: 4.7%, O: 17.2%, Cl: 12.6%, N: 14.4%, S: 11.6%

[0044] It can be confirmed by the above elemental analysis...

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Abstract

The invention relates to a cefepime hydrochloride compound prepared by a new synthetic method. The method comprises the following steps: first enabling aminothiazoly loximate to react with formic acidto generate 2-(2-formammidotiezol-4-group)-2-methoxyimino acetic acid, then adding 7-MPYCA and triethylamine, taking N,N-diisopropylethylamine and N,N-dimethylformamide as solvents and p-toluenesulfonyl chloride as a catalyst, stirring the above substances to react to prepare the cefepime hydrochloride.

Description

technical field [0001] The invention relates to a cefepime hydrochloride compound with a new synthesis method, which belongs to the technical field of medicinal chemistry. Background technique [0002] Cefepime hydrochloride, its chemical name is: 1-[[(6R,7R)-7-[2-(2-amino-4-thiazolyl)-glyoxylamide]-2-carboxy-8-oxo -5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-methylpyrrolidine chloride, 72-(Z)-(O-methyl oxime), hydrochloride monohydrate, molecular formula: C 19 h 25 ClN 6 o 5 S 2 ·HCl·H 2 O, molecular weight: 571.49, structural formula: [0003] [0004] It is a broad-spectrum fourth-generation cephalosporin, which achieves bactericidal effect by inhibiting the biosynthesis of bacterial cell walls. In vitro tests show that this product has effects on Gram-positive bacteria and negative bacteria, especially the activity of Streptococcus and Streptococcus pneumoniae is greatly enhanced. At present, it is mainly used clinically for various infections caused by...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/46C07D501/06B01J31/02A61P31/04
Inventor 王明
Owner HAINAN LINGKANG PHARMA CO LTD
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