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Process for the preparation of imipenem

A technology of imipenem and general formula, applied in the field of imipenem preparation, can solve problems such as troublesome multi-step purification process and the like

Inactive Publication Date: 2005-11-09
RANBAXY LAB LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reagents used for activation are not commercially available and their preparation involves a cumbersome multi-step purification process

Method used

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  • Process for the preparation of imipenem
  • Process for the preparation of imipenem
  • Process for the preparation of imipenem

Examples

Experimental program
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Effect test

Embodiment 1

[0048] Step a) prepare enol phosphate intermediate

[0049] A solution of (3R,5R,6S)-2-oxo-6-[(1R)-1-hydroxyethyl]carbapenem-3-carboxylic acid p-nitrobenzyl ester (30 g) was dissolved under N, In a mixture of N-dimethylacetamide (300ml) and dichloromethane (150ml). The solution was cooled to -55°C and 4-(dimethylamino)pyridine (0.17 g) was added followed by diisopropylethylamine (26.7 g). The mixture was stirred at -55°C for 5 minutes, then a solution of diphenyl chlorophosphate (25.4 g) in dichloromethane (30 ml) was added dropwise at -55°C to -45°C. The reaction mixture thus obtained was stirred for an additional 30 minutes to obtain the enol phosphate.

[0050] Step b) preparation of thanamycin ester

[0051] The reaction mixture from step a) was further cooled to -70°C to -75°C and 2-aminoethanethiol hydrochloride (12 g) was added over 10 minutes at -75°C to -60°C in N,N-di Solution in methylacetamide (60ml). The reaction mixture was stirred for an additional 60 minut...

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Abstract

The present invention relates to an improved, cost effective and industrially advantageous process for the preparation of imipenem.

Description

field of invention [0001] The present invention relates to an improved, low-cost, effective and industrially advantageous preparation method of imipenem. Background of the invention [0002] Imipenem monohydrate shown in the general formula I is an N-iminomethyl derivative of thanamycin, and has the general structural formula I. [0003] [0004] Formula I [0005] It is the first new β-lactam antibiotic that can be used clinically, and it has a carbapenem (carbapenem) ring system. Imipenem exhibits an extremely broad spectrum of activity against Gram-positive and Gram-negative aerobic and anaerobic organisms, partly due to its high stability in the presence of β-lactamase. [0006] Imipenem was first described in US Patent No. 4,194,047. Several general methods for preparing thanamycin N-methylene derivatives including imipenem from thanamycin have been listed in US Patent No. 4,194,047. It has been found that the method for preparing imipene...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D477/00A61K31/407A61P31/04C07D477/02C07D477/20
CPCC07D477/02C07D477/20Y02P20/55A61P31/04
Inventor Y·库马N·特瓦里B·P·莱
Owner RANBAXY LAB LTD
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