2-(3-cyano-4-substituted phenyl)-4-methyl-1, 3-selenazole-5-formic acid and formate compounds and preparation method thereof

A compound, the technology of ethyl formate, which is applied in the field of medicine and can solve problems that have not been reported

Inactive Publication Date: 2014-07-23
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 2-(3-cyano-4-substituted phenyl)-4-methyl-1,3-selenazole-5-carboxylic acid and its esters have not been reported as xanthine oxidase inhibitors

Method used

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  • 2-(3-cyano-4-substituted phenyl)-4-methyl-1, 3-selenazole-5-formic acid and formate compounds and preparation method thereof
  • 2-(3-cyano-4-substituted phenyl)-4-methyl-1, 3-selenazole-5-formic acid and formate compounds and preparation method thereof
  • 2-(3-cyano-4-substituted phenyl)-4-methyl-1, 3-selenazole-5-formic acid and formate compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0107] Example 1: Preparation of 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid (Compound 1)

[0108] (1) Addition: 0.79 g of selenium powder (10 mmol) was mixed with 0.46 g of sodium borohydride (12 mmol), and the system was evacuated and then filled with nitrogen for protection; under ice bath, 20 mL of absolute ethanol was added to obtain selenium hydrochloride Sodium solution; add 1.2 g (10 mmol) of p-hydroxybenzonitrile, reflux for 6 h; add 6 M HCl solution dropwise to make the system acidic, and continue the reaction for 1 h; add 100 mL H 2 O, stirred in an ice bath for 0.5 h, filtered, and dried to obtain the crude product of 4-hydroxyselenobenzamide with a yield of 60%. The crude product was directly used in the next reaction without purification.

[0109] (2) Cyclization: 2.0 g (10 mmol) of crude 4-hydroxyselenobenzamide in 5 mL of ethanol, stirred and heated to reflux, and 1.65 g (10 mmol) of ethyl 2-chloroacetoacetate was added dropwise. Co...

Embodiment 2

[0114] Example 2: Preparation of 2-(3-cyano-4-ethoxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid (compound 2)

[0115] 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid ethyl ester was prepared in the same manner as in Example 1.

[0116] Alkylation: crude ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-selenazole-5-carboxylate 336 mg (1 mmol), potassium carbonate 138 mg (1 mmol), 5 mg potassium iodide and 2 mL DMF were mixed, and 108 mg (1 mmol) of ethyl bromide was added dropwise under stirring at room temperature: the reaction liquid was heated to 35 °C and reacted for 8 h; after cooling, it was poured into five times the amount of water, and a solid was precipitated. Suction filtration, washing the filter cake with water, and drying to obtain crude ethyl 2-(3-cyano-4-ethoxyphenyl)-4-methyl-1,3-selenazole-5-carboxylate with a yield of 83%. The crude product was directly used in the next reaction without purification.

[0117] Hydrolysis: 364 mg (...

Embodiment 3

[0119] Example 3: Preparation of 2-(3-cyano-4-propoxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid (compound 3)

[0120] In addition to using the corresponding alkylating agent in the alkylation step, the same method as in Example 2 was used to prepare 2-(3-cyano-4-propoxyphenyl)-4-methyl-1,3- Selenazole-5-carboxylic acid (compound 3), the total yield is 17% (based on raw material p-hydroxybenzonitrile), its structural formula, 1 H-NMR and MS data are listed in Table-1 below.

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Abstract

The invention belongs to the technical field of medicines, relates to 2-(3-cyano-4-substituted phenyl)-4-methyl-1, 3-selenazole-5-formic acid and formate compounds, pharmaceutically acceptable salts, pharmaceutically acceptable solvates which have xanthine oxidase inhibitory activity and have the general formula of I, and a preparation method thereof, and also relates to use of the compounds in preparation of drugs for treating hyperuricemia and gout diseases. The formula I is shown in the specification, R and R' independently are H; or R and R' independently are straight chain or branched chain C1-C10 alkyl, C3-C10 ene alkyl, C3-C10 alkyne alkyl, C4-C7 naphthenic alkyl, and C7-C10 aryl alkyl.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to 2-(3-cyano-4-substituted phenyl)-4-methyl-1,3-selenazole-5-carboxylic acid and its ester compounds and preparation methods, in particular to 2 -(3-cyano-4-substituted phenyl)-4-methyl-1,3-selenazole-5-carboxylic acid and its esters, pharmaceutically acceptable salts, pharmaceutically acceptable solvates and their preparation methods, and the use of these compounds in medicine. 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, so reports vary from country to country larger. According to available data, the prevalence of hyperuricemia in Europe and the United States is about 2% to 18%, and the prevalence of gout is 0.2% to 1.7%. In the indigenous population of the South Pacific, hype...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D293/06A61K31/41A61P19/06
CPCC07D293/06
Inventor 张为革关奇程增进沈杞容孙俊姚飞
Owner SHENYANG PHARMA UNIVERSITY
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