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Novel process for synthesizing rebamipide

A technology of rebamipide and new process, which is applied in the field of new synthesis process of rebamipide, can solve the problems of unavailable rebamipide raw materials, high production cost, harsh process conditions, etc., and achieve simple process and high process conditions Gentle, easy-to-industrial effect

Active Publication Date: 2018-05-25
CHONGQING SHENGHUAXI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The present invention mainly solves the problems of unavailable rebamipide raw materials, harsh process conditions and high production cost, and aims to provide a new preparation process of rebamipide

Method used

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  • Novel process for synthesizing rebamipide
  • Novel process for synthesizing rebamipide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] p-Chlorobenzoylglycine methyl ester (compound 14):

[0027] Add 12.5 g (100 mmol) of glycine methyl ester hydrochloride, 125 ml of dichloromethane, and 30.3 g of triethylamine into the reaction flask, cool down to 0-5°C, add 18.4 g (105 mmol) of p-chlorobenzoyl chloride dropwise, and add After completion, the temperature was raised to 25°C for 4 h, and the complete conversion of the reactant to the product was monitored by TLC (developing solvent: dichloromethane). After completion of the reaction, add 30 mL of water and stir, separate the organic layer, add 30 mL of dichloromethane to the water layer to extract twice, combine the organic layers, wash with water until neutral, dry with 20 g of anhydrous sodium sulfate, filter off the desiccant, and concentrate under reduced pressure to nothing. As far as the slip-out, 21.5 g of solid was obtained, with a yield of 95%, which was directly used in the next step without purification. ESI-MS(m / z ) : 228 [M+1] + .

[0028]...

Embodiment 2

[0035] p-Chlorobenzoylglycine methyl ester (compound 14):

[0036] Add 12.5 g (100 mmol) of glycine methyl ester hydrochloride, 125 ml of diethyl ether, and 25.2 g (300 mmol) of sodium bicarbonate into the reaction flask, cool down to 0-5°C, add 18.4 g (105 mmol) of p-chlorobenzoyl chloride dropwise, After the addition, the temperature was raised to 25°C for 4 h, and the complete conversion of the reactant to the product was monitored by TLC (developing solvent: dichloromethane). After the reaction is complete, add 30 mL of water and stir, separate the organic layer, add 30 mL of dichloromethane to the water layer to extract twice, combine the organic layers, wash with water until neutral, dry over anhydrous sodium sulfate, filter off the desiccant, and concentrate under reduced pressure to nothing. So far, 20.6g of solid was obtained, with a yield of 91%, which was directly used in the next step without purification. ESI-MS(m / z ) : 228 [M+1] + .

[0037] Synthesis of imine...

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Abstract

The invention discloses a novel process for synthesizing rebamipide. The novel process comprises the following steps: adopting glycine methyl ester as a starting raw material, then performing amidation and chlorination to obtain chloroimide intermediate, enabling the chloroimide intermediate to react with bromomethylquinolone, and hydrolyzing to obtain the rebamipide. The novel process has the advantages that the starting raw material is low in price and easy to obtain, the reaction yield is high, the industrialization is easy to realize and the like.

Description

technical field [0001] The present invention relates to pharmaceutical chemical technology, and more specifically relates to a new synthesis process of rebamipide. Background technique [0002] Rebamipide is a quinolone compound with the chemical formula (1), and its chemical name is: 2-(4-chlorobenzamido)-3-(2(1H)-quinolone-4 -base) propionic acid, the original manufacturer is Japan Otsuka Pharmaceutical Co., Ltd. Rebamipide is an active new-generation gastric mucosal protective agent, which can improve the histological healing quality of gastric ulcer, reduce ulcer recurrence, and treat gastric mucosal damage caused by non-steroidal anti-inflammatory drugs (NSAIDs), alcohol and other factors. The damage has a good effect, and it still has a good curative effect on gastric mucosal lesions that failed to eradicate H.pylori infection, and it is the only gastric mucosal protective agent that can increase PG synthesis and scavenge and inhibit free radicals, and has high clinic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/227
CPCC07D215/227
Inventor 李子清
Owner CHONGQING SHENGHUAXI PHARMA CO LTD
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