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New cefotiam hydrochloride synthesis method and applications of cefotiam hydrochloride in sterile powder injection

A technology of cefotiam hydrochloride and hydrochloric acid, which is applied in the field of synthesis of cefotiam hydrochloride, can solve the problems of infeasibility, excessively increasing the consumption of 2-mercaptobenzimidazole compounds, and low yield, so as to avoid long reaction steps, Environmental friendliness and high yield

Inactive Publication Date: 2017-12-19
CHONGQING SHENGHUAXI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But, this synthetic method will obtain high yield, needs the 3-position methylene activation of 7-aminocephalosporanic acid to be prepared into formula three compound, increases the material consumption of 2-mercaptobenzimidazole compound in vain; If 7-aminocephalosporanic acid Direct reaction with Formula 2, the yield is too low to be feasible

Method used

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  • New cefotiam hydrochloride synthesis method and applications of cefotiam hydrochloride in sterile powder injection
  • New cefotiam hydrochloride synthesis method and applications of cefotiam hydrochloride in sterile powder injection
  • New cefotiam hydrochloride synthesis method and applications of cefotiam hydrochloride in sterile powder injection

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reference example 1

[0019] Reference example 1 preparation of formula one compound

[0020] Add 20g (73.5mmol) of 7-aminocephalosporanic acid and 7.5g (188mmol) of sodium hydroxide into 100mL of ethanol aqueous solution, react at -15°C for 2h, adjust the pH value to 1-2 with hydrochloric acid, keep the reaction for 1h, and separate to obtain Formula 1 compound 13g.

Embodiment 1

[0021] The preparation of embodiment 1 cefotiam hydrochloride

[0022] Add 10 g (47 mmol) of the compound of formula 1, 22 g (70 mmol) of the compound of formula 2, and 10 mL of 1 mol / L hydrochloric acid aqueous solution into 100 mL of acetonitrile, and react at 45°C for 3 h. Evaporate most of the acetonitrile under reduced pressure, add 50mL of water, 10mL of concentrated hydrochloric acid, stir at room temperature for 1h, filter with suction, cool the filtrate to 0-5°C, add acetone dropwise until a large amount of turbidity appears, keep stirring for 1h, continue to add 300mL of acetone dropwise, keep warm Stir for 1 h, filter and dry with suction to obtain 25 g of white cefotiam hydrochloride crystalline powder, with a molar yield of 88%, an HPLC content of 98.30%, and a maximum of 0.45% simple impurities.

Embodiment 2

[0023] The preparation of embodiment 2 cefotiam hydrochloride

[0024] Add 20 g (94 mmol) of the compound of formula 1, 38 g (122 mmol) of the compound of formula 2, and 19 mL of 1 mol / L hydrochloric acid aqueous solution into 200 mL of acetonitrile, and react at 30°C for 6 h. Evaporate most of the acetonitrile under reduced pressure, add 100mL of water, 20mL of concentrated hydrochloric acid, stir at room temperature for 1h, filter with suction, cool the filtrate to 0-5°C, add acetone dropwise until a large amount of turbidity appears, keep stirring for 1h, continue to add 600mL of acetone dropwise, keep warm Stir for 1 h, filter and dry with suction to obtain 48 g of white cefotiam hydrochloride crystalline powder, with a molar yield of 85%, an HPLC content of 98.12%, and a maximum simple compound of 0.46%.

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Abstract

The invention discloses a new cefotiam hydrochloride synthesis method, which comprises that a compound represented by a formula 1 and a compound represented by a formula 2 are subjected to a reaction to prepare the cefotiam hydrochloride. According to the present invention, the method has advantages of short reaction steps, simple and convenient operation, high yield, atom economy, low cost and environment friendliness; and the cefotiam hydrochloride prepared through the synthesis method has good quality, and can be used for preparing the cefotiam hydrochloride powder injection for clinical use.

Description

technical field [0001] The invention relates to the technical field of medical chemicals, in particular to a new method for synthesizing cefotiam hydrochloride. Background technique [0002] Cefotiam hydrochloride (cefotiam hydrochloride), the chemical name is (6R,7R)-7-[(2-amino-4-thiazolyl)acetamido]-3-[[[1-[2-(dimethylamine Base) ethyl]-1H-tetrazol-5-yl]thio]methyl]-8-oxo-5-thio-1-azabicyclo[4.2.0]oct2-ene-2- Carboxylic acid dihydrochloride, the structure is as follows: [0003] [0004] It is a second-generation semi-synthetic cephalosporin developed by Takeda Corporation of Japan and first launched in Japan in 1981. It has a strong bactericidal effect on a wide range of microorganisms (including Gram-positive and negative pathogens). At present, the clinically used preparations are all sterile freeze-dried mixed powder preparations composed of cefotiam hydrochloride and buffer sodium carbonate. [0005] The classic method of synthesizing cefotiam hydrochloride is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/04C07D501/36A61K9/14A61K31/546A61P31/04
CPCC07D501/36A61K9/0019A61K9/143A61K31/546C07D501/04
Inventor 刘军
Owner CHONGQING SHENGHUAXI PHARMA CO LTD
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