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Method for synthesizing 1 beta methyl carbapenem antibiotic

A technology of methyl carbapenem and synthesis method, applied in the directions of bulk chemical production, organic chemistry, etc., can solve problems such as low efficiency, unfavorable large-scale production, etc., and achieve the effect of simplifying the operation process and being beneficial to large-scale production

Inactive Publication Date: 2011-01-05
SHENZHEN HAIBIN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0026] The deprotection methods of penem ester publicly reported in the current patent literature are obtained by catalytic hydrogenolysis of palladium carbon or platinum carbon as a catalyst in a buffer solution system. Good for mass production

Method used

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  • Method for synthesizing 1 beta methyl carbapenem antibiotic
  • Method for synthesizing 1 beta methyl carbapenem antibiotic
  • Method for synthesizing 1 beta methyl carbapenem antibiotic

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Preparation of Meropenem (Compound I)

[0063]

[0064]10.0 g of meropenem (compound Ia), 300.0 g of acetonitrile, 300 g of water, 5.5 g of 3,5,-lutidine, and 4.8 g of 5% palladium carbon were added to a 2L autoclave, and the air was removed. Introduce hydrogen, react at room temperature for 6 hours, after the reaction is complete, collect palladium carbon by filtration, add 400 g of acetone to the filtrate, stir and crystallize at -15°C for 20 hours, filter, and dry the product to obtain 5.7 g of meropenem (compound I) trihydrate , The mass yield is 57.0%.

[0065] The target compound (compound I) is a known substance, and the retention time and mass spectrum of the target product obtained in Example 1 in HPLC are consistent with the existing literature.

Embodiment 2

[0067] Preparation of Meropenem (Compound I)

[0068]

[0069] Add 12.0 g of meropenem (compound Ia), 300.0 g of acetone, 300 g of water, 5.5 g of 3,5,-lutidine, and 4.8 g of 5% palladium carbon into a 2L autoclave, remove the air, Introduce hydrogen and react at room temperature for 10 hours. After the reaction is complete, collect palladium carbon by filtration, add 400 g of acetone to the filtrate, stir and crystallize at -20°C for 20 hours, filter, and dry the product to obtain 5.9 g of meropenem (compound I) trihydrate , The mass yield is 49.2%.

[0070] The target compound (compound I) is a known substance, and the retention time and mass spectrum of the target product obtained in Example 2 in HPLC are consistent with the existing literature.

Embodiment 3

[0072] Preparation of Meropenem (Compound I)

[0073]

[0074] Put 20.0 g of meropenem (compound Ia), 600.0 g of acetonitrile, 600 g of water, 5.5 g of 3,5,-lutidine, and 8.5 g of palladium carbon into a 2L autoclave, remove the air, and feed Hydrogen, react at room temperature for 6 hours, after the reaction is complete, collect palladium carbon by filtration, add 400g of acetonitrile to the filtrate, stir and crystallize at 0°C for 24 hours, filter, and dry the product to obtain 9.8g of meropenem (Compound I) trihydrate, the mass yield Rate 49.0%.

[0075] The target compound (compound I) is a known substance, and the retention time and mass spectrum of the target product obtained in Example 3 in HPLC are consistent with the existing literature.

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Abstract

The invention relates to a method for synthesizing 1 beta methyl carbapenem antibiotic, comprising the following steps of: (1) adding an organic solvent, water, pivaloyloxymethyl ester, organic base and a catalyst to a reactor, introducing hydrogen, and then reacting for above 15 minutes, wherein the pressure of the hydrogen is controlled in 10.0 MPa, and the reaction temperature is controlled below 70 DEG C; (2) monitoring by using a HPLC (High Performance Liquid Chromatography), removing the hydrogen after finishing reaction, and filtering and recovering the catalyst (palladium charcoal or platinum charcoal); and (3) cooling a filtrate, adding a crystallizing solvent, stirring and devitrifying for above 10 minutes, and then filtering to obtain a corresponding target compound. The method has convenient operation, and a reaction liquid can be directly added to the solvent for crystallization without purification.

Description

technical field [0001] The invention relates to a method for synthesizing 1β-methyl carbapenem antibiotics. Background technique [0002] Carbapenem antibiotics are a new type of fully synthetic β-lactam antibiotics, which have strong antibacterial activity against Gram-positive bacteria and negative bacteria, aerobic bacteria, and anaerobic bacteria. Since the discovery of thiamycin in 1976, the research on carbapenem antibiotics has made great progress. In particular, 1β-methyl carbapenem antibiotics have good chemical stability and are stable to β-lactamase and renal dehydropeptide-I enzymes. They are currently one of the first-choice drugs for the treatment of severe and multidrug-resistant bacterial infections. It has been more and more widely used in clinical practice. [0003] Currently commercialized 1β-methyl carbapenem antibiotics include meropenem (I), biapenem (II), doripenem (III) and ertapenem (IV), the general structure of which is as follows : [0004] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D477/06C07D477/20C07D519/06
CPCY02P20/55
Inventor 赵鹏任鹏徐建忠徐登峰江枫鲁亮辉苏昌明陈波
Owner SHENZHEN HAIBIN PHARMA
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