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Synthesizing method of rebamipide

A synthesis method and technology of rebamipide, applied in the field of synthesis of rebamipide, can solve the problems of low content of rebamipide, easy generation of impurities and high production cost, and achieve lower production cost, less impurities and less pollution Effect

Active Publication Date: 2013-05-22
ZHEJIANG YUANLIJIAN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Synthesizing method of rebamipide

Examples

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Effect test

Embodiment 1

[0022] 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 4-chlorobenzoyl chloride / alcohol dropwise, which contains 9.6g of 4-chlorobenzoyl chloride The mixed solution was stirred and added dropwise for 2 hours. After the reaction, it was allowed to stand for 2 hours. The transition body was obtained by suction filtration. The transition body was dissolved in 200 mL of purified water, and the temperature was controlled at 20°C. Stirring was continued for 2 hours after addition, filter cake-like solid was obtained by suction filtration, washed repeatedly with 70°C purified water and ethanol until the pH was 7, and 13.2 g of white crystal powder was obtained after drying, which was the finished rebamipide, with a yiel...

Embodiment 2

[0023] 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 4-chlorobenzoyl chloride / alcohol dropwise, which contains 48g of 4-chlorobenzoyl chloride The mixed solution was stirred and added dropwise for 2 hours. After the reaction, it was allowed to stand for 2 hours. The transition body was obtained by suction filtration. The transition body was dissolved in 1000 mL of purified water, and the temperature was controlled at 20°C. Then continue to stir for 2 hours, suction filter to obtain a filter cake solid, wash with 70°C purified water and ethanol repeatedly until the pH is 7, and dry to obtain 65.5g of white crystal powder, which is the finished product rebamipide, with a yield of 93.6% , the content of rebamip...

Embodiment 3

[0024] 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 / alcohol, which contains 4-chlorobenzoyl A mixture of 9.6 kg of acid chloride was stirred and added dropwise to react for 2 hours. After the reaction was completed, it was allowed to stand for 2 hours, and the transition body was obtained by suction filtration. The transition body was dissolved in 200 l of purified water, and the temperature was controlled at 20°C. Add the acid dropwise until the pH was 2. , continue to stir for 2 hours after stopping the dropwise addition, filter cake-like solids by suction filtration, rinse repeatedly with 70°C purified water and ethanol until the pH is 7, and obta...

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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 Gastric ulcer drugs can prevent ulcers and promote ulcer healing, increase gastric mucosal blood flow, prostaglandin E 2 The synthesis of rebamipide and the secretion of gastric mucus can remove oxygen free radicals, promote the healing of peptic ulcer and the improvement of inflammation; rebamipide has a variety of preparation and synthesis methods, but most of them have low rebamipide content in the obtained finished product, and There are disadvantages that some impurities are difficult to remove, and the acylation reaction process in the synthesis requires relatively strict environmental conditions, which all increase the production cost. Contents of the in...

Claims

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Application Information

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IPC IPC(8): C07D215/227
Inventor 付泽飞郑清泉邹林
Owner ZHEJIANG YUANLIJIAN PHARMA
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