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Method for synthesizing rebamipide

A synthetic method, the technology of rebamipide, applied in the field of synthesis of rebamipide, can solve problems such as complex production process, expensive starting materials, and difficulty in industrialization, so as to simplify the synthesis process, avoid incomplete reaction, and process conditions mild effect

Inactive Publication Date: 2018-02-09
CHONGQING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] In view of the above-mentioned deficiencies in the prior art, the purpose of the present invention is to provide a new process for the synthesis of rebamipide, which solves the technical problems in the prior art such as expensive starting materials, complicated production process, high cost and difficulty in industrialization.

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  • Method for synthesizing rebamipide
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  • Method for synthesizing rebamipide

Examples

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Embodiment 1

[0043] 1) Synthesis of p-chlorobenzoyl glycine methyl ester (compound 14):

[0044] Add 12.5g (100mmol) of glycine methyl ester hydrochloride into a reaction flask containing 125ml of dichloromethane, stir and dissolve thoroughly, then add 30.3g of triethylamine, then cool at 0-5°C, and pour into the above reaction solution 18.4g (105mmol) p-chlorobenzoyl chloride was added dropwise for acylation reaction, and after the addition was completed, the temperature was raised to 25°C for 4 hours, and TLC monitored that the reactant was completely converted into the product (the developing solvent was 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, add 20 g of anhydrous sodium sulfate to dry, filter off the desiccant, and concentrate under reduced pressure to Until there is no slip-out, 21.5 g of soli...

Embodiment 2

[0052] 1) p-chlorobenzoyl glycine methyl ester (compound 14):

[0053] Add 12.5g (100mmol) of glycine methyl ester hydrochloride into a reaction flask containing 125ml of diethyl ether, stir well to dissolve, then add 25.2g (300mmol) of sodium bicarbonate, then cool at 0-5°C, and drop 18.4g (105 mmol) p-chlorobenzoyl chloride, after the addition, the temperature was raised to 25° C. for 4 h, and TLC monitored that the reactant was completely converted into the product (the developing solvent was 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 layer, add 50 mL of water to the organic layer, wash 3 times until neutral, add anhydrous sodium sulfate to dry, filter off Desiccant, concentrated under reduced pressure until there is no slip-out, to obtain 20.6g of solid p-chlorobenzoylglycine methyl ester, the yield is 91%, which is directly ...

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Abstract

The invention discloses a method for synthesizing rebamipide. The method includes carrying out acylation and chlorination on glycine methyl ester to obtain chlorimide intermediates; carrying out substitution reaction on the chlorimide intermediates and bromomethyl quinolinone; carrying out hydrolysis to obtain the rebamipide. The glycine methyl ester is used as a starting material. The method hasthe advantages that the starting material is low in cost and is easily available, the method is high in reaction yield, industrialization can be facilitated, and the like.

Description

technical field [0001] The present invention relates to pharmaceutical chemical technology, and more specifically relates to a method for synthesizing rebamipide. Background technique [0002] Rebamipide (Rebamipide, 1) is a quinolinone compound with chemical formula as shown in (1), and its chemical name is: 2-(4-chlorobenzamido)-3-(2-(1H )-quinolinone-4-yl)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 cannot eradicate H.pylori infection, and it is the only gastric mucosal protective agent that can increase PG synthesis and scavenge and inhibit free radical...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/227
CPCC07D215/227
Inventor 沟引宁
Owner CHONGQING UNIV OF TECH
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