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6-(3,4-substituted phenyl)-2-mercaptopyrimidine-4-carboxylic acid compounds and their preparation method and use

A technology of mercaptopyrimidine and compounds, applied in the field of 6--2-mercaptopyrimidine-4-carboxylic acid compounds and their preparation, and preparation of medicines for treating gout

Active Publication Date: 2021-08-24
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 6-(3,4-substituted phenyl)-2-mercaptopyrimidine-4-carboxylic acid compounds as xanthine oxidase inhibitors have not been reported yet

Method used

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  • 6-(3,4-substituted phenyl)-2-mercaptopyrimidine-4-carboxylic acid compounds and their preparation method and use
  • 6-(3,4-substituted phenyl)-2-mercaptopyrimidine-4-carboxylic acid compounds and their preparation method and use
  • 6-(3,4-substituted phenyl)-2-mercaptopyrimidine-4-carboxylic acid compounds and their preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1: Preparation of 6-(3-bromo-4-isopropoxyphenyl)-2-mercaptopyrimidine-4-carboxylic acid (compound 1)

[0073] (Z)-4-(3-bromo-4-isopropoxyphenyl)-2-hydroxy-4-oxobut-2-enoic acid (0.66g, 2mmol), thiourea (0.76g, 10mmol ), was added to glacial acetic acid (30 mL), and the temperature was raised to 100° C. to react for 8 hours. After the system was cooled to room temperature, the organic solvent was removed under reduced pressure, and the solid was purified by column chromatography to obtain 6-(3-bromo-4-isopropoxyphenyl)-2-mercaptopyrimidine-4-carboxylic acid.

[0074] The yield of 6-(3-bromo-4-isopropoxyphenyl)-2-mercaptopyrimidine-4-carboxylic acid (compound 1) is 66%, its structural formula, 1 H-NMR and MS data are listed in Table-1 below.

Embodiment 2

[0075] Example 2: Preparation of 6-(3-bromo-4-isobutoxyphenyl)-2-mercaptopyrimidine-4-carboxylic acid (compound 2)

[0076] Except using corresponding alkylating agent in one step of alkylation, prepare 6-(3-bromo-4-isobutoxyphenyl)-2-mercaptopyrimidine-4-carboxylic acid in the same manner as in Example 1 ( Compound 2), the yield is 71%, its structural formula, 1 H-NMR and MS data are listed in Table-1 below.

Embodiment 3

[0077] Example 3: Preparation of 6-(3-bromo-4-isoamyloxyphenyl)-2-mercaptopyrimidine-4-carboxylic acid (compound 3)

[0078] 6-(3-bromo-4-isoamyloxyphenyl)-2-mercaptopyrimidine-4-carboxylic acid (compound 3) was prepared in the same manner as in Example 1, and the yield was 67%. 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 6-(3,4-substituted phenyl)-2-mercaptopyrimidine-4-carboxylic acid compounds of general formula I having xanthine oxidase inhibitory activity, pharmaceutically acceptable salts, pharmaceutically acceptable Medicinal solvates and preparation methods thereof, the invention also relates to the use of these compounds in the treatment of hyperuricemia and gout. The general structural formula of the 6-(3,4-substituted phenyl)-2-mercaptopyrimidine-4-carboxylic acid compound is as follows: wherein, R and X are as described in the claims and description.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to 6-(3,4-substituted phenyl)-2-mercaptopyrimidine-4-carboxylic acid compounds and their preparation methods and applications; specifically, 6-(3,4-substituted phenyl) - 2-mercaptopyrimidine-4-carboxylic acid compounds, pharmaceutically acceptable salts, pharmaceutically acceptable solvates and preparation methods thereof, and the use of these compounds in the preparation of medicines for treating gout. Background technique [0002] Gout is a series of inflammatory reactions caused by the accumulation of uric acid in joints and other places in the body due to purine metabolism disorder or decreased uric acid excretion. With the changes in people's diet structure and the increase in intake of animal protein and fat, the number of patients with hyperuricemia and gout has increased significantly, and has now become a global metabolic disease. The clinical features of gout are hyperuric...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/40A61P19/06
CPCA61P19/06C07D239/40
Inventor 张为革石爱龙王赫张利超王思博杨明正包凯关奇
Owner SHENYANG PHARMA UNIVERSITY
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