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The synthetic method of rebamipide

A synthesis method and technology of rebamipide, applied in the field of rebamipide synthesis, can solve the problems of high production cost, low content of rebamipide, easy generation of impurities, etc., achieve less impurities, reduce production cost, improve yield effect

Active Publication Date: 2016-04-27
ZHEJIANG YUANLIJIAN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The present invention aims to overcome the problems of low rebamipide content in the finished product existing in the existing rebamipide synthesis method, easy to produce impurities, and high production cost, and provides an improved rebamipide synthesis method , while improving the yield of the product, it produces less impurities, less pollution to the environment, lowers the production cost, and is suitable for large-scale and high-yield production of rebamipide

Method used

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  • The synthetic method of rebamipide
  • The synthetic method of rebamipide
  • The synthetic method of rebamipide

Examples

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Effect test

Embodiment 1

[0020] Example 1, in a 500mL beaker, add 14g of raw amino acid salt, 2-amino-3-(1.2-dihydro-2-oxo-4-quinolyl) propionate hydrochloride to 250mL of purified water, add hydrogen Sodium oxide 5g, increase the temperature to 55°C, add 1g of activated carbon, stir to dissolve and filter, take the filtrate, cool down to 0°C, add dropwise the mixture of 4-chlorobenzoyl chloride and acetone or N,N-dimethylformamide Mixed solution, wherein the mixed solution containing 9.6g of 4-chlorobenzoyl chloride was stirred and added dropwise for reaction for 2 hours, left to stand for 2 hours after the reaction was completed, and the transition body was obtained by suction filtration, and the transition body was dissolved in 200mL purified water, and the temperature was controlled at At 20°C, add acid dropwise until the pH is 2, stop the dropwise addition and continue to stir for 2 hours, filter with suction to get a cake-like solid, wash it repeatedly with 70°C purified water and ethanol until t...

Embodiment 2

[0021] Example 2, in a 3000mL beaker, add 70g of raw amino acid salt, 2-amino-3-(1.2-dihydro-2-oxo-4-quinolyl) propionate hydrochloride to 250mL of purified water, add hydrogen Sodium oxide 25g, increase the temperature to 65°C, add 5g of activated carbon, stir to dissolve and filter, take the filtrate, cool down to 2°C, add dropwise the mixture of 4-chlorobenzoyl chloride and acetone or N,N-dimethylformamide The mixed solution, the mixed solution containing 48g of 4-chlorobenzoyl chloride, was stirred and added dropwise for 2 hours. After the reaction was completed, it was left to stand for 2 hours, and the transition body was obtained by suction filtration. The transition body was dissolved in 1000mL purified water, and the temperature was controlled at 20 ℃, add acid dropwise until the pH is 2, stop the dropwise addition and continue to stir for 2 hours, filter with suction to obtain a cake-like solid, wash it repeatedly with 70°C purified water and ethanol until the pH is 7...

Embodiment 3

[0022] Example 3, 14kg raw material amino acid salt, 2-amino-3-(1.2-dihydro-2-oxo-4-quinolyl) propionate hydrochloride was added to 250L purified water in a 300L glass-lined reaction tank , add 5kg of sodium hydroxide, increase the temperature to 70°C, add 1kg of activated carbon, stir to dissolve and filter, take the filtrate, cool down to 5°C, add dropwise 4-chlorobenzoyl chloride / acetone or N,N-dimethyl The mixed solution of formamide, wherein containing the mixed solution of 9.6kg of 4-chlorobenzoyl chloride, stirred and added dropwise to react for 2 hours, left standstill for 2 hours after the reaction was finished, and obtained the transition body by suction filtration, and the transition body was dissolved in 200l purified water, Control the temperature at 20°C, add acid dropwise until the pH is 2, continue stirring for 2 hours after stopping the dropwise addition, filter with suction to obtain a cake-like solid, rinse repeatedly with 70°C purified water and ethanol unti...

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Abstract

The invention provides an improved method for preparing rebamipide from 2-amino-3-(1.2-dihydro-2-oxo-4-quinolyl) propionic acid hydrochloride (abbreviated as amino acid salt) through a one-step reaction. By utilizing the method, the rebamipide with high purity can be prepared. After activated carbon is added to the amino acid salt to carry out adsorption decoloration under the alkaline condition, the amino acid salt reacts for 1 to 4 hours in alkaline alcohol liquid to obtain the finished product, wherein the yield is from 80% to 95%; and the product purity is more than 99.5%. According to the method, the yield of the rebamipide product is improved; few impurities are generated; the environment pollution is small; and the production cost is lowered. Therefore, the method provided by the invention is suitable for the large-scale production mode with the high yield.

Description

technical field [0001] The invention relates to the field of medicine preparation, in particular to a method for synthesizing rebamipide. Background technique [0002] Rebamipide, molecular formula: C19H15ClN2O4, chemical name: 2-(4-chloroformamido)-3-[2(1H)-quinolone-4-yl]propionic acid, is a new type of treatment Drugs for gastric ulcer can prevent ulcer occurrence and promote ulcer healing, increase gastric mucosal blood flow, synthesis of prostaglandin E2 and secretion of gastric mucus, remove oxygen free radicals, promote healing of peptic ulcer and improve inflammation; Rebamipide has a variety of preparation and synthesis methods, but most of them have the disadvantages that the content of rebamipide in the obtained finished product is low, and some impurities are difficult to remove. The acylation reaction process in the synthesis has strict requirements on the environmental conditions. These All raised production costs. Contents of the invention [0003] The pre...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/227
Inventor 付泽飞郑清泉邹林
Owner ZHEJIANG YUANLIJIAN PHARMA
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