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Preparation method of Cefotiam hydrochloride

A technology of cefotiam hydrochloride and raw materials, applied in the field of pharmaceutical antibiotics, can solve the problems of increasing operation steps, increasing production costs, and no literature reports

Inactive Publication Date: 2015-11-25
谈丽娜
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The comparison of the two methods shows that although the second method is more reasonable than the first method, the protective group and the deprotective group both increase the operation steps, reduce the yield and increase the production cost.
[0007] The preparation method of ATC HCl of the present invention and the method for synthesizing cefotiam with ATC HCl all have no bibliographical information so far

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0024] Suspend 4.73g of 7-ACMT fluoroborate (0.01mol. 7-ACMT content is 79.2%) in 20ml of acetonitrile, 25ml of acetone, and 8ml of water, cool to 0-5°C, add 5.98ml of tributylamine, and stir at 0-5°C After 20 minutes, add ATC.HCL2.35g (0.011mol) and stir below 5°C for 3 hours. After the reaction, add 8ml of water, 30ml of dichloromethane and 7ml of concentrated hydrochloric acid, stir for 10 minutes, and separate the layers. Separate the water layer and raise the temperature to 25°C. , add 170ml of acetone, stir at 20-25°C for 3 hours, filter the crystals, wash the crystals with 15ml × 2 times of acetone, and vacuum-dry for 3 hours below 45°C to obtain 5.3g off-white crystalline powder of ceftiamide dihydrochloride (HPLC Purity 99.2%, moisture content 6.1%, acetone 2.5%) yield 84.5%.

example 2

[0026] Nitrile, 4ml of water, 30ml of dichloromethane, cooled to 0°C, stirred and added 3.5ml of triethylamine, stirred at 0-5°C for 20 minutes, then added ATC. Add 15ml of water and 7ml of concentrated salt, stir for 10 minutes to separate the water layer, add 170ml of acetone at 20-50°C, stir at 20-25°C for 3 hours, filter the crystals, wash the crystals with 15ml×2 times of acetone, below 45°C Vacuum-dried for 3 hours to obtain 5.32g off-white crystalline powder of ceftiamide dihydrochloride (HPLC purity 98.7%, moisture content 5.95%, acetone 3.1%) yield 84.72%

example 3

[0028] Suspend 10g of 7-ACMT fluoroborate (0.021ml, the content of 7ACMT is 79.2%) in 42ml of acetonitrile, 15ml of water, and 25ml of acetone, cool to 0-5°C, add 7.35ml of triethylamine, and stir at 0-5°C for 20 minutes , add ATC.HCL5.37g (0.025mol). Stir at 0-5°C for 3 hours, add 31.5ml of water and 14ml of concentrated hydrochloric acid after the reaction, stir for 10 minutes, let the layers stand still, separate the water layer, add 160ml of acetone at 20-25°C, then cool down to 50°C, and stir for 10 minutes After that, white crystals slowly precipitated, continued to stir for half an hour, and a large amount of crystals precipitated. Controlled 5°C and added 190ml of acetone, stirred for 2 hours, filtered the crystals, washed the crystals with 50ml x 2 times of acetone, dried in vacuum at 35°C for 5 hours, and obtained 10.54g The yield of white ceftiamide dihydrochloride crystals (HPLC purity 99.65%, water content 5.35%, acetone 0.01%) was 83.25%.

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Abstract

A preparation method of Cefotiam hydrochloride is characterized by comprising the following steps: (1) ATA is used as a raw material to prepare ATC.HCl crystals: the ATA raw material is added into solvent, dry hydrogen chloride gas is blown into the solvent, a chlorinating agent is added, a reaction is carried out at the temperature of 0-30 DEG C, and the ATC.HCl crystals are filtered out after the reaction; and (2) ATC.HCl is used as a raw material to directly synthesize Cefotiam hydrochloride: 7-ACMT is alkalified and the alkalified 7-ACMT is dissolved in an aqueous solvent, ATC.HCl is added to carry out an acylation reaction at the temperature of minus 10-35 DEG C, an organic solvent is separated out after the reaction, hydrochloric acid is added into an aqueous phase, a hydrophilic solvent which is 3-6 times greater than volume of a water layer is added, and Cefotiam hydrochloride crystals are precipitated out.

Description

technical field [0001] The invention belongs to the field of drug antibiotics, in particular to a preparation method of cefotiam hydrochloride. Background technique [0002] Cefotiam hydrochloride is a second-generation antibiotic for injection, and its dihydrochloride (CefotiamDihydrochloride) and buffer sodium carbonate mixed powder preparation (trade name Pansporin) are used clinically. The effect of this product on Gram-positive bacteria is similar to that of cefazolin, and it has a strong antibacterial effect on Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, and Haemophilus. It also has antibacterial effect on Citrobacter, Enterobacter, and indole-positive proteus. [0003] The synthetic routes of cefotiam hydrochloride all take 7-aminocephalosporanic acid (7-ACA) as raw material, and its 3-position and 1-(2-dimethylaminoethyl)-1,2,3,4- —The thiol bond reaction of tetramazole-5-mercaptan (DMMT) is generally catalyzed by sodium bicarbonate or dichlorophosp...

Claims

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Application Information

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IPC IPC(8): C07D501/36C07D501/06
CPCC07D501/36C07B2200/13C07D501/06C07D501/12
Inventor 谈丽娜
Owner 谈丽娜
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