Method for synthesizing cefpirome sulfate

A cefpirome sulfate and synthetic method technology, applied in chemical recovery, organic chemistry, etc., can solve the problems of many side reactions, high production cost, and long reaction time, so as to shorten the reaction time, increase the product yield, and reduce the production rate. cost effect

Inactive Publication Date: 2010-06-23
YIYUAN XINQUAN CHEM
View PDF0 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the yields of these two steps are relatively high, the first step will use a strong alkaline environment, which has a greater impact on the stability of the product and more side reactions, and 2,3 cyclopentenopyridine and N,N -Diethylaniline is azeotropic, and it is difficult to obtain recycling. On the other hand, the reaction time between 7-ACA and 2,3 cyclopentenopyridine is long, which is not conducive to industrial production
The main disadvantages are: (1) high production cost (2) many side reactions (3) low utilization rate of raw materials

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
  • Method for synthesizing cefpirome sulfate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 1. Synthesis of quaternary ammonium salt intermediates

[0022] Add cyclopentenopyridine 26.61g (0.223mol) in the four-necked flask and be dissolved in 100ml cyclohexane, under N 2 Under protection, stirred and added TMSI 12.06g (0.06mol) dropwise, slowly raised the temperature to 70°C, refluxed for 4h, and cooled to room temperature.

[0023] 2.7-Synthesis of ACP

[0024] Add 100ml of dichloromethane and 13.6g (0.05mol) of 7-aminocephalosporanic acid (7-ACA) into the three-necked flask, stir and dropwise add 19.33g (0.12mol) of hexamethyldisilazane at 15°C, dropwise After the addition, react at 15°C for 50min, add the quaternary ammonium salt intermediate solution prepared in step (1), react at 5°C for 1.5h, then slowly raise the temperature to 15°C, and add 100ml DMF and 56ml concentrated Hydrochloric acid, stirred and cooled to 0°C, slowly added the above solution into the mixture, stirred and reacted for 30 minutes. 50ml of water was added thereto, and after stir...

Embodiment 2

[0028] 1. Synthesis of quaternary ammonium salt intermediates

[0029] Add cyclopentenopyridine 29.85g (0.25mol) in four-necked flask and be dissolved in 100ml cyclohexane, under N 2 Under protection, stirred and added TMSI 12.06g (0.06mol) dropwise, slowly raised the temperature to 70°C, refluxed for 4h, and cooled to room temperature.

[0030] 2.7-Synthesis of ACP

[0031] Add 100ml of acetonitrile and 13.6g (0.05mol) of 7-aminocephalosporanic acid (7-ACA) into the three-necked flask, stir and add 19.33g (0.12mol) of hexamethyldisilazane dropwise at 15°C, and the dropwise addition is completed React at 15°C for 50min, add the quaternary ammonium salt intermediate solution prepared in step (1), react at 5°C for 1.5h, then slowly heat up to 15°C, in a three-necked flask, add 100ml DMF and 56ml concentrated hydrochloric acid, stir After cooling to 0°C, the above solution was slowly added to the mixture, and stirred for 30 minutes. 50ml of water was added thereto, and after s...

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 relates to a method for synthesizing cefpirome sulfate. The method comprises the following steps: firstly, preparing 2,3-cyclopentenopyridine and trimethylsilyl iodide into quaternary ammonium salt intermediate compound; Secondly, performing carboxyl and amido protection for 7-ACA through hexamethyl disilylamine, and finally adding quaternary ammonium salt intermediate compound into the well protected 7-ACA solution for rapid reaction to obtain cefpirome mother nuclide 7-ACP; Thirdly, performing N- acidylation reaction to 7-ACP and AE active ester in the mixed phase of DMF and water, and obtaining cefpirome sulfate after salt forming reaction. By using step one to obtain quaternary ammonium salt intermediate compound, not only N,N- diethylaniline is saved, but also the side chain 2,3-cyclopentenopyridine is easy to rectify and recycle, thereby greatly reducing the production cost; simultaneously, the disadvantages of strong alkalinity and a large amount of side reaction of 2,3-cyclopentenopyridine are overcome. By using the method, the yield rate and the purity of the product can be improved.

Description

technical field [0001] The present invention relates to the synthetic method of cefpirome sulfate. technical background [0002] As the fourth-generation cephalosporin antibiotic, cefpirome has stronger antibacterial effect, wider antibacterial spectrum, and maintains effective blood drug concentration for a longer time. It is especially suitable for neutropenia patients with infections, severe lower respiratory tract infections, Sepsis, bacteremia, concurrent upper and lower urinary tract infections, and skin and soft tissue infections have effects on multidrug-resistant Enterobacteriaceae, Citrobacter, and Klebsiella and Escherichia coli producing ceftazidime hydrolase. [0003] Cefpirome Sulfate (Cefpirome Sulfate) was listed in Mexico and Sweden in 1992, under the trade name Cefrom, and is currently on the market in nearly 20 countries around the world. It has a superior effect of penetrating the outer membrane of bacteria, and plays an antibacterial effect by hindering...

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): C07D501/46C07D501/04
CPCY02P20/582
Inventor 周磊王孟陈娇吕光海
Owner YIYUAN XINQUAN CHEM
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap