Preparation method of 3,4-substitituted thiobenzamide and application of 3,4-substitituted thiobenzamide in febuxostat synthesis

A technology of thiobenzamide and thioacetamide, applied in the direction of organic chemistry, etc., can solve the problems of large discharge pollution of three wastes, complicated operation and the like

Inactive Publication Date: 2014-11-26
CHONGQING SHENGHUAXI PHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The operation steps of the method are to place 4-hydroxybenzonitrile, hydrogen sulfide gas and solvent water in a closed high-pressure device, and heat to 70° C. for an addition reaction to obtain 4-hydroxythio

Method used

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  • Preparation method of 3,4-substitituted thiobenzamide and application of 3,4-substitituted thiobenzamide in febuxostat synthesis
  • Preparation method of 3,4-substitituted thiobenzamide and application of 3,4-substitituted thiobenzamide in febuxostat synthesis
  • Preparation method of 3,4-substitituted thiobenzamide and application of 3,4-substitituted thiobenzamide in febuxostat synthesis

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Experimental program
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Effect test

Embodiment 1

[0023] Table 1 The research results of changing the reaction solvent and temperature and other factors

[0024]

[0025] The 4-hydroxythiobenzamide obtained by the above method is used as a raw material to synthesize Febuxostat according to the methods of patents JP6-329647 / 1994 and JP10-45733 / 1998.

[0026] Example 2

Embodiment 2

[0028] Table 2 The research results of changing the reaction solvent and temperature and other factors

[0029]

[0030] Using the 4-hydroxy-3-nitrothiobenzamide obtained by the above method as a raw material, Febuxostat was synthesized by referring to the method of patent EP0513379 / 1992.

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Abstract

The invention relates to a preparation method of 3,4-substituted thiobenzamide. The 3,4-substituted thiobenzamide prepared by the method can be used to synthesis of febuxostat, a novel drug for treating gout.

Description

technical field [0001] The invention discloses a method for preparing 3,4-substituted thiobenzamide, and the product of the method can be used in the synthesis of new anti-gout drug Febuxostat. Background technique [0002] Febuxostat was first approved by the European Medicines Agency (EMA) in April 2008 for the treatment of hyperuricemia and related diseases caused by it, such as gout. The chemical name of febuxostat is: 2-(3-cyano-4-isobutoxy)phenyl-4-methyl-5-thiazolecarboxylic acid, and its chemical structure is as follows. [0003] [0004] The core part of the molecular structure of febuxostat is a 2-substituted phenylthiazole derivative, and its synthesis is mainly based on 3,4-substituted thiobenzamide (2) and 2-halogenated ethyl acetoacetate The ester (3) is formed by cyclization, and the reaction formula is as follows. [0005] [0006] According to the description of the patent EP0513379 / 1992, compound 2 and 2-halogenated ethyl acetoacetate (3) are synthe...

Claims

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Application Information

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IPC IPC(8): C07C327/48C07D277/56
Inventor 李能刚
Owner CHONGQING SHENGHUAXI PHARMA CO LTD
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