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Production method of tigecycline raw medicinal material

A technology for tigecycline and a production method, which is applied in the directions of chemical instruments and methods, anti-infective drugs, drug combinations, etc., can solve the problems of increasing the impurity content of isomers, affecting product quality, and difficult to separate by-products, and achieves overcoming The effect of high difficulty, improved quality, and high yield

Active Publication Date: 2014-12-24
HUNAN ER KANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has short steps, but the by-products of the condensing agent used are difficult to separate, which affects the quality of the product, and the direct use of organic acids will also increase the content of isomer impurities in the product

Method used

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  • Production method of tigecycline raw medicinal material
  • Production method of tigecycline raw medicinal material
  • Production method of tigecycline raw medicinal material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add glycine (10.00g, 0.13mol) and triethylamine (15.00g, 0.15mol) into dichloromethane (50ml), stir under ice bath until the temperature of the system is below 5°C, at this temperature the above system drops 2-Chloro-2-methylpropane (14.00 g, 0.15 mol) diluted with dichloromethane (20 mL) was added. After the dropwise addition, react for 1 h. The pH was adjusted to 10 with sodium hydroxide solution, and the reaction was stirred at room temperature for 30 min. Add hydrochloric acid to the reaction system, adjust the pH to 5 and stir at room temperature for 1 h. Extract with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, distilled under reduced pressure and dried to obtain compound 2 (16.59 g), with a yield of 95%.

Embodiment 2

[0035] Add glycine (10.00g, 0.13mol) and triethylamine (20.21g, 0.20mol) into dichloromethane (50ml), stir under ice bath until the temperature of the system is below 5°C, at this temperature the above system drops Add 2-chloro-2-methylpropane (18.49g, 0.20mol) diluted with dichloromethane (20ml). After the dropwise addition, react for 1 h. The pH was adjusted to 10 with sodium hydroxide solution, and the reaction was stirred at room temperature for 30 min. Add hydrochloric acid to the reaction system, adjust the pH to 5 and stir at room temperature for 1 h. Extract with ethyl acetate. The organic phase was dried with anhydrous sodium sulfate, distilled under reduced pressure and dried to obtain compound 2 (16.86 g), with a yield of 96.5%.

Embodiment 3

[0037] Compound 2 (16.59 g, 0.13 mol) and potassium hydroxide (7.10 g, 0.13 mol) were added to isopropanol. Heat to reflux for 3h, cool and filter, and wash the filter cake with an appropriate amount of dichloromethane. After drying, the crude product (21.32 g) was obtained and used directly in the next reaction.

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Abstract

The invention discloses a production method of a tigecycline raw medicinal material and particularly relates to a method which comprises the following steps: by using glycine as a raw material, carrying out a reaction with 2-chloro-2-methylpropane to prepare tertiary butyl glycine; then forming corresponding salt with an inorganic alkali and reacting with tertiary butyl acyl chloride to generate anhydride; and carrying out a condensation reaction on anhydride and 9-amino minocyline to prepare tigecycline. The production method of the tigecycline raw medicinal material disclosed by the invention has the advantages that the raw material is low in price and easily available, and products with high purity and high yield are obtained by adjusting a synthetic route.

Description

Technical field [0001] The invention discloses a production method of adding cordin substang -drug, which involves the field of chemical raw material synthesis. Background technique [0002] Donnah was developed by Wyeth in the United States and was used for the treatment of patients with complex skin and skin structure or complex abdominal infection in the age of 18 and over 18 years old.Its chemical name is (4S, 4AS, 5AR, 12AS) -9- (2- (2- (Unitarine) acetyamin) -4, 7-double (diophytamine) -1, 4, 4A, 5, 5A, 6, 11, 12A-octagoor-3, 10,12, 12A-tetraxyl-1, 11-di-oxygen-2-萘 pyrameamide, which is the first new generation of glycinamateinTetracycline antibiotics of Tetracycline.Its structure is similar to tetracycline drugs. In June 2005, the US FDA approved for adult complex skin and soft tissue infection (CSSSLS) and adult complex abdominal infections, including complex appendicitis, burns infection, abdominal abscess, deep soft tissue infection and ulcerInfect.Donnales are still in...

Claims

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Application Information

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IPC IPC(8): C07C237/26C07C231/12A61P31/00
Inventor 帅放文章家伟王向峰
Owner HUNAN ER KANG PHARMA
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