Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Environment-friendly method for preparing antibacterial medicine cefodizime acid with low cost

A technology for ceftazidime and antibacterial drugs, which is applied in the new preparation field, can solve the problems of low yield, poor reaction degree and high impurities, and achieves the effects of reducing cost, saving energy consumption and reducing pollution

Inactive Publication Date: 2019-07-12
SHANGHAI NEW ASIA PHARMA +1
View PDF7 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above process, the reaction is complicated, requires multiple purification processes and protection and deprotection processes, the reaction degree is poor, the yield is low, and the color grade of the obtained product is relatively high, and the impurities are relatively high, which is not conducive to subsequent production, research and utilization.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Environment-friendly method for preparing antibacterial medicine cefodizime acid with low cost
  • Environment-friendly method for preparing antibacterial medicine cefodizime acid with low cost

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0044] At room temperature, 150 ml of dimethyl carbonate, 20 g of 7-aminocephalosporanic acid, and 15 g of MMTA were added. Add 15g of boron trifluoride-dimethyl carbonate complex and 2g of methanesulfonic acid at the same temperature, control the temperature at 35-40°C and time the reaction for 1-2.0hr, then lower the temperature to below 20°C and add 320ml of pure water for hydrolysis.

[0045] Then add 2g of activated carbon for decolorization and filter for 20min. Control the temperature of the filtrate below 5°C, add dropwise a dilute alkali solution to adjust the pH to 3.8-4.0, and precipitate crystals. After filtering, the filter cake was washed with pure water, and then washed with acetone after draining, and the wet product of TACS was obtained after draining.

[0046] The purity of the high-pressure liquid phase is 98.2%, and the color grade is lower than the yellow-green standard colorimetric solution No. 3.

Embodiment 1-2

[0048] Add 150ml of dichloromethane to the reactor to control the temperature below 10 degrees, add 24ml of methanol, add the above TACS wet product, add 2ml of triethylamine dropwise under stirring to dissolve it, and then add 26g of AE-active ester. Timed reaction 2.0-5.0hr. Add 500ml of pure water to extract the organic phase, then add 2g of activated carbon to the water phase to decolorize for 20min, filter, wash the carbon cake with 30ml of water, add ethanol to the filtrate, add dilute acid to acetone to adjust the pH=3.5-3.7 to precipitate crystals. Suction filtration, wash the filter cake with pure water, and drain. The filter cake was washed with acetone and drained. The dried cefodizime acid is 28.5g.

[0049] The purity of the high-pressure liquid phase is 98.9%, and the color grade is lower than the yellow-green standard colorimetric solution No. 3.

Embodiment 2-1

[0051] At room temperature, 120ml of dimethyl carbonate, 20g of 7-aminocephalosporanic acid, and 15g of MMTA were added. Add 10 g of boron trifluoride-dimethyl carbonate complex and 5 days of concentrated sulfuric acid at the same temperature, control the temperature at 35-40°C and time the reaction for 1-2.0 hours, then cool down to below 20°C and add 320ml of pure water for hydrolysis. Then add 2g of activated carbon for decolorization and filter for 20min. Control the temperature of the filtrate below 5°C, add dropwise a dilute alkali solution to adjust the pH to 3.8-4.0, and precipitate crystals. After filtering, the filter cake was washed with pure water, and then washed with acetone after draining, and the wet product of TACS was obtained after draining.

[0052] The purity of the high-pressure liquid phase is 98.5%, and the color grade is lower than the yellow-green standard colorimetric solution No. 3.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides an environment-friendly method for preparing an antibacterial medicine cefodizime acid with low cost. The method is characterized by comprising the steps that under the condition of taking dimethyl carbonate as a solvent, a boron trifluoride complex is adopted for catalyzing a condensation reaction of 7-aminocephalosporanic acid and 2-sulfydryl-4-methyl-5-thiazole acetic acid to obtain an intermediate 7-amidogen-3-(5-carboxymethyl-4-methyl-1,3-thiazole-2-mercapto methyl)cephalosporin-2-alkene-2-carboxylic acid, and through wet processing, the intermediate and AE active ester are subjected to direct condensation to obtain a target product. The crude cefodizime acid product produced through the method is high in content and good in color class, and the maximum impuritycontent of cefodizime sodium synthesized by the cefodizime acid can be controlled below 0.1%.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a new preparation method of the antibacterial drug cefodizime. Background technique [0002] Cefodizime acid chemical name (6R,7R)-7-[(2-amino-4-thiazolyl)-(methoxyimino)acetamido]-3-[[(5-carboxymethyl-4- Methyl-2-thiazolyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, for third generation injection An important precursor of cefodizime sodium. [0003] At present, the technology of this variety is mainly 7-aminocephalosporanic acid and 1-(2-dimethylaminoethyl)-1H-5-mercaptotetrazolium in pure water and catalyzed synthesis of TACS with inorganic alkali solution under high temperature conditions. That is, 7-amino-3-(5-carboxymethyl-4-methyl-1,3-thiazole-2-mercaptomethyl) cef-2-ene-2-carboxylic acid, then add organic alcohol and other solvents, drop Add dilute acid to adjust the pH to crystallize, and centrifuge to obtain a completely dried TACS solid....

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/36C07D501/06
CPCC07D501/06C07D501/36
Inventor 于永宏刘明张义勋
Owner SHANGHAI NEW ASIA PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com