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1/5 Cefamandole sodium compound

The technology of cefamandide sodium and montdol sodium is applied in the directions of organic chemistry, pharmaceutical formulations, medical preparations containing active ingredients, etc., and can solve the problems of low thermal decomposition temperature, unqualified turbidity, poor fluidity and the like, Achieve wide application prospects, stable product quality, and good thermal stability.

Active Publication Date: 2019-05-10
HAINAN MEIDA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In addition, the cefamandole sodium compound prepared by the above method is an anhydrous substance, which has serious problems such as poor storage stability, low thermal decomposition temperature, poor fluidity, and easy moisture absorption.
Thereby affecting the product quality, resulting in unclear preparation products, unqualified turbidity, and reducing the stability of the preparation

Method used

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  • 1/5 Cefamandole sodium compound
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  • 1/5 Cefamandole sodium compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The preparation of embodiment 1 1 / 5 cefamandole sodium compound

[0026] (1) 1L acetonitrile, 200g 3-acetoxymethyl-5-sulfur-7-amino-8-oxo-1-azabicyclooct-2-ene-2carboxylic acid, 1kg methylmercaptotetrazolium, Mix 900ml of boron trifluoride / acetonitrile complex, heat up to 30°C, stir rapidly for 2 hours, cool down to 0°C after the reaction, mix the reaction liquid with 1.5L of purified water pre-cooled to 0°C, and stir slowly until After crystals are precipitated, stir for another 30 minutes, add 10% ammonia water to adjust the pH value to 3.0, control the temperature at 0-5° C., grow the crystals for 2 hours, filter, wash twice with 1 L of acetone, and dry in vacuum to obtain a white crystalline powder (6R ,7R)-7amino-3[(Z)-2-(4-methylthiazol)-5-yl]vinyl-8oxo-5-thia-1-azabicyclo[4.2.0]octane -2-ene-2-carboxylic acid 221g;

[0027] (2) (6R,7R)-7amino-3[(Z)-2-(4-methylthiazol)-5-yl]vinyl-8oxo-5-thia-1-azabicyclo [4.2.0] Mix oct-2-ene-2-carboxylic acid with 2L of ethyl ...

Embodiment 2

[0029] The preparation of embodiment 2 1 / 5 cefamandole sodium compound

[0030] (1) Mix 1.5L acetonitrile, 300g 3-acetoxymethyl-5-sulfur-7-amino-8-oxo-1-azabicyclooct-2-ene-2carboxylic acid, 1.5kg methylmercaptotetraazole Mix oxazole and 1.4L boron trifluoride / acetonitrile complex, raise the temperature to 40°C, stir the reaction rapidly for 1h, cool down to 5°C after the reaction, and mix the reaction solution with 2.25L purified water pre-cooled to 5°C, Stir slowly until crystals are precipitated, then stir for 30 minutes, add 10% ammonia water to adjust the pH to 3.4, control the temperature at 0-5°C, grow crystals for 3 hours, filter, wash twice with 1.5L of acetone, and dry in vacuum to obtain white crystals Sexual powder (6R,7R)-7amino-3[(Z)-2-(4-methylthiazol)-5-yl]vinyl-8oxo-5-thia-1-azabicyclo[4.2 .0] oct-2-ene-2-carboxylic acid 324g;

[0031] (2) (6R,7R)-7amino-3[(Z)-2-(4-methylthiazol)-5-yl]vinyl-8oxo-5-thia-1-azabicyclo [4.2.0] Mix oct-2-ene-2-carboxylic acid wi...

Embodiment 3

[0033] The preparation of embodiment 3 1 / 5 cefamandole sodium compound

[0034] (1) 1.25L acetonitrile, 250g 3-acetoxymethyl-5-sulfur-7-amino-8-oxo-1-azabicyclooct-2-ene-2 ​​carboxylic acid, 1.25kg methylmercaptotetraazole Mix oxazole and 1.17L boron trifluoride / acetonitrile complex, heat up to 35°C, stir rapidly for 2 hours, cool down to 3°C after the reaction, mix the reaction solution with 1.88L purified water pre-cooled to 2°C, Stir slowly until crystals are precipitated, then stir for 30 minutes, add 10% ammonia water to adjust the pH to 3.2, control the temperature at 0-5°C, grow crystals for 2 hours, filter, wash twice with 1.3L of acetone, and dry in vacuum to obtain white crystals Sexual powder (6R,7R)-7amino-3[(Z)-2-(4-methylthiazol)-5-yl]vinyl-8oxo-5-thia-1-azabicyclo[4.2 .0] Oct-2-ene-2-carboxylic acid 262g;

[0035] (2) (6R,7R)-7amino-3[(Z)-2-(4-methylthiazol)-5-yl]vinyl-8oxo-5-thia-1-azabicyclo [4.2.0] Mix oct-2-ene-2-carboxylic acid with 2.5L ethyl acetate, s...

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Abstract

The invention discloses a 1 / 5 water cefamandole sodium compound and a preparation method thereof. Each mol of cefamandole sodium compound contains 1 / 5 mol of water. The cefamandole sodium compound prepared by the method disclosed by the invention has low impurity content and good stability and has a wider application prospect.

Description

technical field [0001] The invention belongs to the technical field of chemical engineering medicine crystallization, and in particular relates to a 1 / 5 aquacefamandol sodium compound and a preparation method thereof. Background technique [0002] Cefamandole sodium was successfully created in 1972 by U.S. Lilly Company, and it was first listed in the UK in 1978. Cefamandole sodium is also known as formic acid (acyl) benzyl tetrazole cephalosporin sodium, oxybenzyl tetrazole cephalosporin sodium, Cefadoxazole, oxyzole cephalosporin, Pioneer oxybenzazole, cefamandole formate sodium, Pioneer oxybenzazole, etc., are the second-generation semi-synthetic cephalosporins with strong bactericidal effect, and also have the first-generation And some of the advantages of the third-generation cephalosporins, more stable to β-lactamase, broad antibacterial spectrum. [0003] It is reported in the literature that the synthesis of cefamandole sodium mainly contains the following routes: r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/36C07D501/04A61K31/546A61P31/04
CPCC07D501/04C07D501/36
Inventor 廖爱国
Owner HAINAN MEIDA PHARMA