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Synthesis process of cefpirome and its analog

A technology of cefpirome and its analogues, which is applied in the field of new synthetic technology of the fourth-generation cephalosporin antibiotic cefpirome and its analogues, which can solve the problems of low yield, limited application prospects, harsh reaction conditions, etc. , to achieve the effect of cheap iodination reagent, simple synthesis process route and convenient operation

Inactive Publication Date: 2006-05-17
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yields of these methods are not high, and expensive iodination reagents need to be used, and the reaction conditions are harsh, which limits their application prospects

Method used

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  • Synthesis process of cefpirome and its analog
  • Synthesis process of cefpirome and its analog
  • Synthesis process of cefpirome and its analog

Examples

Experimental program
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Effect test

Embodiment 1

[0020] The synthesis of embodiment 1, cefpirome:

[0021] (1), mix 102g of sodium iodide and 2L of acetone together and stir evenly, add 167g of GCLE at 0°C, and monitor the reaction process with high performance liquid chromatography;

[0022] (2), after the reaction is complete, the reaction solution is poured into a separatory funnel, ethyl acetate and water are added, and the liquid is separated, and the organic layer is washed with an aqueous solution of sodium thiosulfate and saturated brine, dried over anhydrous sodium sulfate, and filtered;

[0023] (3), stir the filtrate, and slowly add 163 g of 2,3-cyclopentenopyridine ethyl acetate solution dropwise at -25°C, after the dropwise addition, continue the reaction, and monitor the reaction process with high performance liquid chromatography;

[0024] (4), after the reaction is complete, filter, the filter cake is rinsed with ethyl acetate, and vacuum-dried to obtain 180 g of a light yellow solid;

[0025] (5), above-men...

Embodiment 2

[0029] Embodiment 2, the synthesis of cefpirome analogue:

[0030] (1) Mix 120g of sodium iodide and 2L of acetone and stir evenly, add 195g of GCLE at 0°C, and monitor the reaction process with high performance liquid chromatography;

[0031] (2), after the reaction is complete, the reaction solution is poured into a separatory funnel, ethyl acetate and water are added, and the liquid is separated, and the organic layer is washed with an aqueous solution of sodium thiosulfate and saturated brine, dried over anhydrous sodium sulfate, and filtered;

[0032] (3), stirring the filtrate, slowly dripping an ethyl acetate solution of 126 g of pyridine at -5° C., after the dropwise addition, continue the reaction, and monitor the reaction process with high performance liquid chromatography;

[0033] (4), after the reaction is complete, filter, the filter cake is rinsed with ethyl acetate, and vacuum-dried to obtain 216 g of a light yellow solid;

[0034] (5), above-mentioned light y...

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Abstract

The present invention discloses the new synthesis process of cefpirome and its analog, and prepares cefpirome and its analog with 7-phenacetylamino-3-chloromethyl cephalo olefine acid p-methoxybenzyl ester as material and through certain technological process. The synthesis process has the advantages of cheap iodinating reagent, simple synthesis path, convenient operation, high yield and low cost.

Description

technical field [0001] The invention relates to a medicine preparation process, in particular to a new synthesis process of the fourth-generation cephalosporin antibiotic cefpirome and its analogues. Background technique [0002] Cefpirome (Cefpirome) belongs to the fourth-generation cephalosporin antibiotics. The drug was first successfully developed by the former German company Hoechst, and it was first listed in Sweden and Mexico in 1992. Its trade name is Cefrom. Later, it was successively sold in Britain, France, Germany, Japan, South Korea and other countries. It is the antibiotic with the strongest antibacterial activity against Gram-positive bacteria among the third and fourth-generation cephalosporins known. At present, the excellent antibacterial effect of the drug in vitro and in animal infection models has been confirmed by a large number of clinical trial reports worldwide. It has been successfully applied at home and abroad: (1) Acquired severe lower respirato...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34A61P11/00A61P13/00A61P17/00A61P31/04
Inventor 段学民郑鹏武许艳杰陈立功李阳闫喜龙王敏涂其冬
Owner JIANGXI SCI & TECH NORMAL UNIV
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