Cefotiam hydrochloride compound in new path

A technology of cefotiam hydrochloride and compounds, which is applied in the field of drug synthesis, can solve the problems of high solvent requirements, difficult operation, low yield and product purity, and achieve the effects of high product purity, reduced usage, and low cost of raw materials

Inactive Publication Date: 2010-01-27
HAINAN LINGKANG PHARMA CO LTD
View PDF2 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, hydrogen chloride gas is used, and the reaction is difficult to control, difficult to operate, and the yield is low
Chinese patent CN101096373A discloses a preparation method of cefotiam dihydrate dihydrochloride. In this method, boron trifluoride is used as a catalyst, acylation reaction is required, and the solvent requirement is relatively high, and the reaction steps are

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
  • Cefotiam hydrochloride compound in new path
  • Cefotiam hydrochloride compound in new path
  • Cefotiam hydrochloride compound in new path

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 Synthesis of 2-formylaminothiazole-4-acetic acid

[0034] In the 98% formic acid solution of 1500ml, add the 2-aminothiazole-4-acetic acid of 316 grams (2mol) and 30 grams of 4A molecular sieves, this mixture is heated to 60 ℃ of reaction 3 hours, removes unnecessary formic acid by distillation under reduced pressure, will Add 3000ml of ethyl acetate to the residue, filter to remove molecular sieves, wash the organic phase with 2000ml of distilled water, dry the organic phase with anhydrous sodium sulfate, and distill under reduced pressure to obtain 353 grams of 2-formylaminothiazole-4-acetic acid, the yield 95%.

Embodiment 2

[0035] The synthesis of embodiment 2 cefotiam hydrochloride

[0036] 93 grams of 2-formylaminothiazole-4-acetic acid and 90 ml of N, N-diisopropylethylamine are added to 400 ml of dimethylformamide, the reactant is cooled to 10 ° C, and 97 grams of ( 0.51mol) p-toluenesulfonyl chloride, stirred and reacted at this temperature for 1 hour, then added 210 grams (0.5mol) of 7-ACMT and 295ml triethylamine, stirred vigorously at 5-10°C for 0.5 hours, then added 6mol / l 320ml of hydrochloric acid was reacted at 50°C for 1 hour, then cooled to room temperature and stirred with 4 liters of acetone, the solid was precipitated, filtered, washed with acetone, and vacuum-dried at 40°C to obtain 281g of product, yield: 93.8%.

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 cefotiam hydrochloride compound in a new path. The preparation method comprises the following steps: allowing 2-aminothiazole-4-acetic acid to react with methanoic acid to generate 2-formylaminothiazol-4-acetic acid, adding 7-ACMT and triethylamine, taking N, N-diisopropylethylamine and dimethylfomamide as solvent, taking p-toluene sulfonylchloride as a catalyst, stirring to react, and then adding hydrochloric acid to obtain the cefotiam hydrochloride.

Description

technical field [0001] The invention relates to a cephalosporin compound, in particular to a new route of cefotiam hydrochloride compound, which belongs to the technical field of drug synthesis. Background technique [0002] Cefotiam hydrochloride, chemical name: (6R-trans)-7-[[(2-amino-4-thiazolyl)acetyl]amino]-3-[[[1-[(2-(dimethyl Amino)ethyl]-1H-tetrazol-5-yl]thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxy Acid dihydrochloride, molecular formula: C 18 h 23 N 9 o 4 S 3 2HCl, molecular weight: 598.6, structural formula: [0003] [0004] Cefotiam hydrochloride is a second-generation cephalosporin antibiotic, and its effect on gram-positive bacteria is similar to that of cefazolin, while it is effective on gram-negative bacteria such as Haemophilus, Escherichia coli, Klebsiella, and mirabilis. Proteus, etc. have better effects, and also have antibacterial effects on Enterobacter, Citrobacter, and indole-positive Proteus. Its mechanism of action is ...

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
IPC IPC(8): C07D501/36C07D501/06B01J31/02A61P31/04
Inventor 王明
Owner HAINAN LINGKANG PHARMA CO LTD
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