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Preparation method of decarbamoyl cefuroxime

A technology of carbamoyl head and amino cephalosporanic acid is applied in the field of preparation of decarbamoyl cefuroxime, can solve the problems of reducing chemical reaction process, harsh temperature conditions, long production cycle and the like, and achieves production equipment and operation protection. Low requirements, mild reaction conditions, and the effect of improving product yield

Active Publication Date: 2018-08-24
GUANGDONG LIGUO PHARMACY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Disadvantages of the existing technology: the production process is complex and the production cycle is long; the temperature of the condensation reaction process is required to be controlled below -35°C, and the energy consumption is large; the process uses a highly toxic methanol solvent, which is not conducive to the protection of the operator and affects the production. High requirements for equipment and operation protection
However, diphenyldiazomethane is prone to danger during use, which is not conducive to actual product production
[0005] Chinese patent application CN101289457A discloses that D-7-ACA is used to replace 7-ACA as a raw material to react with SMIA acid chloride to synthesize decarbamoyl cefuroxime. This process reduces the chemical reaction process required in the synthesis and shortens the production cycle, but The temperature conditions are still very harsh, and the reaction temperature is generally between -60 and -40°C

Method used

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  • Preparation method of decarbamoyl cefuroxime
  • Preparation method of decarbamoyl cefuroxime

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 150 mL of purified water to the reaction flask, and add 27.2 g of 7-aminocephalosporanic acid, 2 g of sodium hydroxide, 2.79 g of 2-amino-3-(4-imidazolyl)propionic acid and 0.62 g of 1-benzyl-4- (Methoxymethyl)-N-phenylpiperidin-4-amine, and cooled to 0°C, reacted under stirring, and monitored the reaction by HPLC to obtain 3-deacetyl-7-amino-cephalosporanic acid solution;

[0033] Add 31.2g of phosphorus pentachloride to another reaction flask, and add 90mL of methylene chloride, add 27.9g of 2-methoxyimino-2-furan ammonium acetate (SMIA) under stirring, and control the temperature at 25°C. Reacted for 0.5 hours, and the end point of the reaction was monitored by HPLC to obtain an acid chloride solution;

[0034] Add half of the obtained acid chloride solution to the 3-deacetyl-7-amino-cephalosporanic acid solution, add 4.1g of sodium acetate, stir and react, then add the remaining acid chloride solution to the reaction system, and then add 4.1g of acetic acid Sod...

Embodiment 2

[0037] Add 150 mL of purified water to the reaction flask, and add 27.2 g of 7-aminocephalosporanic acid, 2 g of sodium hydroxide, 1.35 g of 2-amino-3-(4-imidazolyl)propionic acid and 0.4 g of 1-benzyl-4- (Methoxymethyl)-N-phenylpiperidin-4-amine, and cooled to 10°C, reacted under stirring, and monitored the reaction by HPLC to obtain 3-deacetyl-7-amino-cephalosporanic acid solution;

[0038] Add 31.2g phosphorus pentachloride in another reaction flask, and add 90mL redistilled dichloromethane, add 2-methoxyimino-2-furan ammonium acetate (SMIA) 27.9g under stirring, control temperature is 30 ℃ for 0.5 hours, and the end point of the reaction was monitored by HPLC to obtain an acid chloride solution;

[0039] Add half of the obtained acid chloride solution to the 3-deacetyl-7-amino-cephalosporanic acid solution, add 5.7g of sodium acetate, stir the reaction, then add the remaining acid chloride solution to the reaction system, and then add 5.7g of acetic acid Sodium, continue ...

Embodiment 3

[0042] Add 150 mL of purified water to the reaction flask, and add 27.2 g of 7-aminocephalosporanic acid, 2 g of sodium hydroxide, 2.79 g of 2-amino-3-(4-imidazolyl)propionic acid and 0.62 g of 1-benzyl-4- (Methoxymethyl)-N-phenylpiperidin-4-amine, and cooled to 5° C., reacted under stirring, and monitored the reaction by HPLC to obtain 3-deacetyl-7-amino-cephalosporanic acid solution;

[0043] Add 31.2g of phosphorus pentachloride to another reaction flask, and add 90mL of methylene chloride, add 27.9g of 2-methoxyimino-2-furan ammonium acetate (SMIA) under stirring, and control the temperature at 20°C. Reacted for 0.5 hours, and the end point of the reaction was monitored by HPLC to obtain an acid chloride solution;

[0044] Add half of the obtained acid chloride solution to the 3-deacetyl-7-amino-cephalosporanic acid solution, add 5.7g of sodium acetate, stir the reaction, then add the remaining acid chloride solution to the reaction system, and then add 5.7g of acetic acid...

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Abstract

The invention belongs to the field of preparation of pharmaceutical intermediates, and particularly relates to a preparation method of decarbamoyl cefuroxime. The method comprises steps as follows: 7-aminocephalosporanic acid as a mother nucleus for synthesis of decarbamoyl cefuroxime is subjected to esterolysis, a product is then subjected to condensation reaction with an acyl chloride liquor of2-methoxyimino-2-furyl acetic acid ammonium, a reaction product is left to stand and subjected to crystallization by ethanol / hydrochloric acid, washing, suction filtration and drying are performed, and the product decarbamoyl cefuroxime is obtained. According to the method, 7-aminocephalosporanic acid is taken as the raw material and crystalized by ethanol and is safe and low in toxicity, and theproduction cycle is shortened; meanwhile, reaction conditions of the method are mild, and industrial production is facilitated.

Description

technical field [0001] The invention belongs to the field of preparation of pharmaceutical intermediates, in particular to a preparation method of decarbamoyl cefuroxime. Background technique [0002] Cefuroxime (cefuroxime) was produced in the United Kingdom. In 1975, Glaxo Company took the lead in developing the second-generation semi-synthetic cephalosporin, namely cefuroxime. Cefuroxime began to play an important role in clinical medicine. Cefuroxime is a broad-spectrum antibiotic, targeting Gram-negative bacteria and Gram-positive bacteria. Cefuroxime inhibits the bacterial cell wall of the patient, making it difficult to synthesize, or causing damage and defects in the bacterial cell wall of the patient, resulting in the death of the bacteria , so as to achieve the purpose of antibacterial. At present, cefuroxime is widely used in clinical medicine, and it can be used in the treatment of infection or postoperative infection of various diseases such as genitourinary sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/06C07D501/04
CPCC07D501/04C07D501/06C07D501/34
Inventor 曾建江王宝许伟龙廖庆番王雄强陈开明
Owner GUANGDONG LIGUO PHARMACY
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