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Synthesis method of ertapenem monosodium salt

A synthetic method, the technology of ertapenem, which is applied in the field of synthesis of ertapenem monosodium salt, can solve the problems of potential safety hazards and high cost of ertapenem

Pending Publication Date: 2020-01-17
WUHAN QR PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome the problems of high cost and potential safety hazards of ertapenem in the prior art, and provide a new method for preparing ertapenem sodium salt

Method used

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  • Synthesis method of ertapenem monosodium salt
  • Synthesis method of ertapenem monosodium salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Under the condition of -30°C, the penem mother nucleus MAP with the protective group and the equimolar equivalent of the side chain of ertapenem were docked in the solvent tetrahydrofuran and triethylamine to generate an intermediate product; the above intermediate product was prepared as Palladium-charcoal is used as a catalyst and sodium bicarbonate is used as an alkalizing agent to carry out hydrogenation deprotection to obtain the crude product of ertapenem monosodium salt, and then through the method of resin purification, ertapenem monosodium salt can be refined to obtain ertapenem monosodium salt, namely [4R ,5S,6S]-3-[[(3S,5S)-5-[[(3-carboxyphenyl)amino]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxy Ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monosodium salt, the yield was 69.3%.

Embodiment 2

[0017] Under the condition of -10°C, the penem mother nucleus MAP with a protective group of formula I and the side chain of ertapenem of formula II were docked in the solvent diisopropylamine and acetonitrile to generate an intermediate product; The intermediate product is hydrogenated and deprotected with palladium-charcoal as a catalyst and sodium bicarbonate as an alkalizing agent to obtain a crude product of ertapenem monosodium salt, and then purified by resin purification to obtain ertapenem monosodium salt. Namely [4R,5S,6S]-3-[[(3S,5S)-5-[[(3-carboxyphenyl)amino]-3-pyrrolidinyl]thio]-6-[(1R)- 1-Hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monosodium salt, yield 65.7%.

Embodiment 3

[0019] Under the condition of -20°C, the penem nucleus MAP with the protective group of formula I and the side chain of ertapenem of formula II were docked in the solvent diisopropylethylamine and dichloromethane to generate intermediate Product; the above-mentioned intermediate product is hydrogenated and deprotected with palladium-charcoal as a catalyst and sodium bicarbonate as an alkalizing agent to obtain a crude product of ertapenem monosodium salt, and then purified by resin purification to obtain ertapenem Monosodium salt, namely [4R,5S,6S]-3-[[(3S,5S)-5-[[(3-carboxyphenyl)amino]-3-pyrrolidinyl]thio]-6-[ (1R)-1-Hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monosodium salt, yield 64.8% .

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Abstract

The invention provides a synthesis method of ertapenem sodium salt. The synthesis method comprises the following steps: reacting a penem mother nucleus MAP with a protective group with an ertapenem side chain to generate an intermediate product; and performing hydrogenation deprotection and salt formation on the intermediate product to prepare an ertapenem monosodium salt crude product, and then performing refining on the crude ertapenem monosodium salt through a resin purification method to obtain ertapenem monosodium salt. The synthesis method has greatly improved yield, reduced cost, simplified operation steps, low required reagent price and environmental friendliness.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a method for synthesizing ertapenem monosodium salt. Background technique [0002] Ertapenem (ertapenem) is a new type of broad-spectrum carbapenem antibiotic developed by Merck Pharmaceutical Company of the United States. The penem antibiotic that is stable to DHP-1 can obtain satisfactory curative effect for the treatment of community-acquired mixed infections. This product was launched in the United States and Europe in November 2001 and April 2002, respectively. The drug is currently all dependent on imports in the country, and there is no manufacturer to produce it. [0003] At present, many companies in China have devoted themselves to the research and development of ertapenem, and most of them adopt the route in Merck's patent (patent number: US2004 / 0235817A1), but this route has problems such as high cost and potential safety hazards. Contents of the invention [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D477/20C07D477/08C07D477/02
CPCC07D477/20C07D477/08C07D477/02C07B2200/07Y02P20/55
Inventor 申理滔喻林唐红伟
Owner WUHAN QR PHARMA CO LTD
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