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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
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  • 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 cumbersome and difficult. operate
[0007] At present, domestic manufacturers of cefotiam hydrochloride preparations mainly rely on imported raw materials for packaging. There are also manufacturers in China that produce this product, but the yield and product purity are low. Therefore, a new synthetic method for this product is developed. and routes have certain social and economic benefits

Method used

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  • Cefotiam hydrochloride compound in new path
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  • 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%.

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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

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Application Information

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