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Xanthine oxidase inhibitor

A technology of compounds and solvates, applied in the field of xanthine oxidase inhibitors, can solve problems such as no reports yet

Inactive Publication Date: 2016-11-23
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 2-(3-cyano / nitro-4-substituted phenyl)-4-methyl-2H-1,2,3-triazole-4-carboxylic acid and formylhydrazide as xanthine oxidase inhibitors Drug research has not yet been reported

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1: Preparation of 2-(3-cyano-4-n-propoxyphenyl)-5-methyl-2H-1,2,3,-triazole-4-carboxylic acid (compound 1)

[0067] (1) Diazotization and condensation:

[0068] Crude 5-amino-2-n-propoxybenzonitrile (0.48 g, 2.6 mmol), 15% HCl solution (5 mL), was added to H 2 O (5mL), stirred for 30 minutes under ice-bath conditions; NaNO was slowly added dropwise to the system 2 (0.27g, 3.0mmol) of the aqueous solution, dripping finished, continue to react in ice bath for 30 minutes; Add the ethanol solution of ethyl acetoacetate (0.39g, 3mmol) in the system, then use the saturated aqueous solution of sodium acetate to adjust the pH of the system to Neutral, reacted for 30 minutes; a yellow solid was precipitated, suction filtered, the filter cake was washed with water, and dried to obtain crude ethyl 2-(3-cyano-4-n-propoxyphenylhydrazone)-3-oxobutanoate, which was collected as The rate is 83%.

[0069] (2) ring closure:

[0070] Crude ethyl 2-(3-cyano-4-n-propoxyphenylhyd...

Embodiment 2

[0074] Example 2: Preparation of 2-(3-cyano-4-isopropoxyphenyl)-5-methyl-2H-1,2,3,-triazole-4-carboxylic acid (compound 2)

[0075] Except using different raw materials, 2-(3-cyano-4-isopropoxyphenyl)-5-methyl-2H-1,2,3,-triazole was prepared in the same manner as in Example 1 -4-formic acid (compound 2), the total yield is 68% (based on raw material 4-isopropoxy-3-cyanoaniline), its structural formula, 1 H-NMR and MS data are listed in Table-1 below.

Embodiment 3

[0076] Example 3: Preparation of 2-(3-cyano-4-n-butoxyphenyl)-5-methyl-2H-1,2,3,-triazole-4-carboxylic acid (compound 3)

[0077] Except using different raw materials, 2-(3-cyano-4-n-propoxyphenyl)-5-methyl-2H-1,2,3,-triazole was prepared in the same manner as in Example 1 -4-formic acid (compound 3), the total yield is 69% (based on raw material 4-n-butoxy-3-cyanoaniline), its structural formula, 1 H-NMR and MS data are listed in Table-1 below.

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PUM

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Abstract

The invention belongs to the technical field of medicine and relates to 2-(3-cyano / nitro-4-substituted phenyl)-4-methyl-2(i)H( / i)-1,2,3-triazole-4-methane acid and formyl hydrazine compounds shown in the formula I, medicinal salt and medicinal solvate and a preparation method thereof. The substituent definition of the compounds is defined as claim books and manuals. The invention further relates to application of the compounds in preparation of medicine for treatment of hyperuricemia and gout diseases.

Description

technical field [0001] The invention belongs to the technical field of medicine and relates to a series of xanthine oxidase inhibitors, in particular to 2-(3-cyano / nitro-4-substituted phenyl)-4-methyl-2H-1,2,3- Triazole-4-carboxylic acid or 2-(3-cyano / nitro-4-substituted phenyl)-4-methyl-2H-1,2,3-triazole-4-carboxhydrazide compounds and its uses. Background technique [0002] Gout is a global metabolic disease, and its prevalence is affected by various factors such as economic development, environment, eating habits, race, genetics, medical level, diagnostic criteria, and statistical methods. Big. In recent years, the prevalence of gout has been increasing year by year no matter in European and American countries or in Asian countries. The prevalence rates of hyperuricemia and gout in my country also show a linear upward trend. According to statistics, the total prevalence rate of gout in all age groups is about 0.84%. [0003] Gout is caused by the excessive production ...

Claims

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Application Information

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IPC IPC(8): C07D249/06A61K31/4192A61P19/06
CPCC07D249/06
Inventor 张为革石爱龙关奇王赫包凯冯东杰阎殊琦吴越王德发李晓娜
Owner SHENYANG PHARMA UNIVERSITY
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