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Cephe alkene onium salt compound and its preparation and use in preparation of cefepime

A technology of cephems and compounds, applied in the field of preparing cefepime, can solve the problems of high cost, achieve the effects of reducing reaction steps, controlling environmental pollution, and good yield

Active Publication Date: 2005-07-27
GUANGZHOU BAIYUNSHAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

CN101682 also uses GCLH as a raw material to carry out the 4-position esterolysis reaction, 3-position substitution, and 7-position enzymatic hydrolysis reaction to prepare cefepime after the 7-position acylation. higher

Method used

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  • Cephe alkene onium salt compound and its preparation and use in preparation of cefepime
  • Cephe alkene onium salt compound and its preparation and use in preparation of cefepime
  • Cephe alkene onium salt compound and its preparation and use in preparation of cefepime

Examples

Experimental program
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Embodiment Construction

[0050] One, preparation 7-phenylacetamido-3-(1-methyl-1-pyrrolidinium base) methyl-3-cephem-4-carboxylate methoxybenzyl ester (I)

[0051] (A1) Preparation of iodide

[0052] Put 9.73g GCLE and 40ml dichloromethane into the reaction bottle, seal it and avoid light, stir in a water bath at 20-25°C, add dropwise a solution of 4.5g sodium iodide and 20ml acetone, react for 2 hours, drain the solvent, add 50ml dichloromethane, The reactant was dissolved, washed once with 100ml water, and then saturated with 50ml Na 2 S 2 o 3 Wash twice, add anhydrous Na 2 SO 4 Dry, filter, wash the filter cake with 10ml of dichloromethane, combine the filtrate into another dry reaction bottle, stir mechanically, cool down in an ice-salt bath, add 2.1ml of N-methylpyrrolidine dropwise when the internal temperature is ≤0°C, and react After 1 hour, the reaction solution was added into a stirred flask containing 600 ml of isopropanol, and a solid was precipitated, filtered with suction, washed tw...

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Abstract

A cepha alkene onium salt compound, its production and use are disclosed. The constitutional formula and surface features of 7-phenylacetyl amino-group-3-(1-methyl-1-pentazane onium group ) methyl-3-cepha alkane-4-carboxylic acid methoxyl carbobenzoxy group are also disclosed. The production is carried out by taking GCLE original material, nucleophilic substituting reacting, removing blocking group and thiaoxamidine side chain active ester reacting. It achieves low cost, stable product quality, and no environmental pollution.

Description

technical field [0001] The invention relates to a cephalosporin intermediate and a synthesis method thereof, and the application of the intermediate to prepare cefepime. Background technique [0002] Cefepime is the fourth-generation cephalosporin, which has strong antibacterial and bactericidal effects on most Gram-positive cocci and Gram-negative bacilli, including drug-resistant strains capable of producing β-lactamase and green Pseudomonas. Clinically used for systemic infection, especially in the treatment of meningitis, respiratory infection, appendicitis, cholecystitis and other infections. [0003] At present, there are many methods for synthesizing cefepime, and the synthetic route is different due to different starting materials, such as condensation at the 7-position first, substitution at the 3-position, or vice versa. Different starting materials can be selected to prepare different intermediates. The process routes and process conditions for the synthesis of ...

Claims

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Application Information

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IPC IPC(8): A61P31/04C07D501/30
Inventor 于沛白梅文青陈仕勇
Owner GUANGZHOU BAIYUNSHAN PHARM CO LTD
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