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Synthesis method for antidepressant drug vilazodone

A technology for a drug vilazodone and a synthesis method, which is applied in the field of drug synthesis and can solve problems such as increasing the difficulty of purification, reducing reaction steps and the like

Inactive Publication Date: 2013-06-19
南京正济医药销售有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The third method: Heinrich T et al. further improved on the basis of Bathe A, eliminating the step of protection and deprotection, and putting the ammoniation in the last step, reducing the reaction steps, but increasing the difficulty of final purification

Method used

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  • Synthesis method for antidepressant drug vilazodone
  • Synthesis method for antidepressant drug vilazodone
  • Synthesis method for antidepressant drug vilazodone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The first step: the preparation of intermediate 5-nitrobenzofuran-2-carboxylic acid

[0035]

[0036] Add 30g of 5-nitrosalicylaldehyde in a 1L three-necked flask, dissolve it with 170mL of N,N-dimethylformamide, then add 49.6g of potassium carbonate and 29.9g of ethyl bromoacetate in sequence, and the temperature of the reaction solution is raised to 90 ° C, magnetic stirring reaction. After TLC detection of 5-nitrosalicylaldehyde disappearance, 30 g of water was added, and the stirring reaction at 90° C. was continued. Cool the reaction solution after the TLC detection detection reaction is completed. Pour the cooled reaction liquid into 1.8 L of 1 mol / L dilute hydrochloric acid, stir for half an hour and then filter, recrystallize the obtained solid with 30 mL of methanol and 150 mL of ethyl acetate, and filter to obtain 31.7 g of the product, with a yield of 85%

[0037] The second step: the preparation of intermediate 5-nitrobenzofuran-2-carboxamide

[0038] ...

Embodiment 2

[0050] This embodiment is the same as Embodiment 1, the difference is the following steps:

[0051] The first step: the preparation of intermediate 5-nitrobenzofuran-2-carboxylic acid

[0052]

[0053] Add 30g of 5-nitrosalicylaldehyde in a 1L three-necked flask, dissolve it with 170mL of N,N-dimethylformamide, then add 54.5g of potassium carbonate and 59.8g of ethyl bromoacetate in sequence, and the temperature of the reaction solution is raised to 130°C, magnetic stirring reaction. After TLC detection of 5-nitrosalicylaldehyde disappearance, 30 g of water was added, and the stirring reaction at 90° C. was continued. Cool the reaction solution after the TLC detection detection reaction is completed. Pour the cooled reaction solution into 1.8 L of 1 mol / L dilute hydrochloric acid, stir for half an hour and then filter, recrystallize the obtained solid with 30 mL of methanol and 150 mL of ethyl acetate, and filter to obtain 29.8 g of the product, with a yield of 80%

[00...

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Abstract

The present invention provides a synthesis method for an antidepressant drug vilazodone, belonging to the technical field of drug synthesis, and the method comprises the steps of: reacting 5-nitrosalicylaldehyde as a raw material with ethyl bromoacetate under the action of potassium carbonate by heating, to obtain a compound 5-nitrobenzofuran-2-carboxylic acid via hydrolysis; adding in aqueous ammonia after the reaction between 5-nitro-benzofuran-2-carboxylic acid and isobutyl chloroformate is completed, to give 5-nitrobenzofuran-2-carboxamide; reducing the 5-nitrobenzofuran-2-carboxamide by using sodium hydrosulfite to give an intermediate 5-aminobenzofuran-2-carboxamide; cyclizing the 5-aminobenzofuran-2-carboxamide with bis(2-chloroethyl)amine in the action of an alkaline to give 5-piperazinyl-benzofuran-2-carboxamide; and subjecting the 5-piperazinyl-benzofuran-2-carboxamide and 3-(4-chloro-butyl)-5-cyano indole to a substitution reaction to obtain the vilazodone. According to the synthesis method of the invention, the raw materials are cheap, and the reaction process is simple.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a synthesis method of the antidepressant vilazodone. technical background [0002] Vilazodone, English name vilazodone, is a benzofuran derivative, its chemical name is 5-[4-[4-(3-butyl-5-cyano)indole]-1-piperazine]benzene And furan-2-carboxamide. Its chemical structural formula is as follows: [0003] [0004] Vilazodone, originally developed by Merck KGaA, is a 5-HT dual-action antidepressant, which has both selective reuptake inhibition of 5-HT and partial activation of 5-HT1A receptors , and is also the first novel antidepressant of the indolealkylamine class. Vilazodone has a unique mechanism of action, rapid and clear clinical efficacy, less side effects on sexual function, and has a better prospect than traditional SSRI antidepressants. [0005] Currently, there are three main methods for the synthesis of vilazodone reported in the literature. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12
Inventor 葛敏
Owner 南京正济医药销售有限公司
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