2-Arylselenazole compounds and medicinal composition thereof

A compound, the technology of selenazole, which is applied in the field of xanthine oxidase inhibitors to treat gout and hyperuricemia, 2-aryl selenazole compounds, can solve the problems of large toxic and side effects

Active Publication Date: 2014-06-11
NANJING LIFECARE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As far as the chronic disease of gout is concerned, the design of new drugs targeting xanthine oxidase has received extensive attention, and a variety of highly active compounds have entered clinical trials, but they still face many problems such as high toxicity and side effects, and more in-depth research is needed. Research

Method used

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  • 2-Arylselenazole compounds and medicinal composition thereof
  • 2-Arylselenazole compounds and medicinal composition thereof
  • 2-Arylselenazole compounds and medicinal composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0145] Synthesis of 2-(3-cyano-4-ethoxyphenyl)-4-methyl-selenazole-5-carboxylic acid (6)

[0146]

[0147] Step A: Add absolute ethanol (540mL) dropwise to a mixture of selenium powder (50.0g, 0.633mol) and sodium borohydride (26.4g, 0.698mol) within 3 to 4 hours under ice-water bath and nitrogen protection, After the addition was complete, the temperature was raised to room temperature and stirring was continued for 1 hour. Then add a pyridine solution (126mL) containing p-hydroxybenzonitrile (18.84g, 0.158mol), raise the temperature to reflux, then slowly add 2M hydrochloric acid solution (320mL) dropwise, and the dropwise addition time is not less than 4 hours, and reflux after the addition is completed. overnight. TLC analysis indicated that the reaction was complete. Most of the ethanol was evaporated under reduced pressure, diluted with water (400mL), extracted with ethyl acetate (200mL×2), the combined organic phase was washed with 2M hydrochloric acid (100mL), the...

Embodiment 2

[0156] Synthesis of 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-selenazole-5-carboxylic acid (7)

[0157]

[0158] For the experimental operation, see Step E and Step F in Example 1.

[0159] 1 H NMR (DMSO-d 6 , 400MHz) δ8.26(d, J=2.4Hz, 1H), 8.18(dd, J=2.0, 9.2Hz, 1H), 7.34(d, J=9.2Hz, 1H), 4.00(d, J=6.8 Hz, 2H), 2.63(s, 3H), 2.14~2.04(m, 1H), 1.02(d, J=6.8Hz, 6H). MS (EI, m / z): 363.2 [M-H] - .

Embodiment 3

[0161] Synthesis of 2-(3-cyano-4-isopropoxyphenyl)-4-methyl-selenazole-5-carboxylic acid (8)

[0162]

[0163] For the experimental operation, see Step E and Step F in Example 1.

[0164] 1 H NMR (DMSO-d 6 , 400MHz) δ8.29(d, J=2.4Hz, 1H), 8.20(dd, J=2.4, 8.8Hz, 1H), 7.38(d, J=8.8Hz, 1H), 4.94~4.88(m, 1H ), 2.65(s, 3H), 1.36(d, J=6.0Hz, 6H). MS (EI, m / z): 349.1 [M-H] - .

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Abstract

The invention discloses 2-arylselenazole compounds and a medicinal composition thereof. The 2-arylselenazole compounds are compounds represented by formula (I) or pharmaceutically acceptable salts thereof. The 2-arylselenazole compounds have a xanthine oxidase inhibition activity. The compounds or pharmaceutically acceptable salts thereof can be applied to prepare medicines for preventing or treating hyperuricemia, gout, diabetic nephropathy, inflammatory diseases and neurological system diseases.

Description

technical field [0001] The invention relates to a class of 2-aryl selenazole compounds and applications thereof, specifically belonging to the field of medicinal chemistry. The present invention also relates to the preparation method of these compounds, the pharmaceutical composition containing these compounds and their medical application, especially the application as xanthine oxidase inhibitor to treat gout and hyperuricemia. Background technique [0002] Gout is a disease caused by the excessive production of uric acid due to the disorder of purine metabolism in the body, and the deposition of sodium urate in the body. Gout is the second most common metabolic disease after diabetes, and this disease has been listed by the United Nations as one of the twenty chronic diseases in the 21st century. Epidemiological studies at home and abroad have shown that with the improvement of human living standards and the extension of average human life expectancy, the incidence of hyp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D293/06C07D421/10C07D421/12C07D495/04A61K31/41A61K31/4439A61K31/5377A61K31/496A61K31/4365A61P19/06A61P13/12A61P29/00A61P25/00
CPCC07D495/04A61K31/41C07D421/10A61K31/4365A61K31/496C07D293/06A61K31/4439A61K31/5377C07D421/12A61P13/12A61P19/06A61P25/00A61P29/00A61P43/00
Inventor 史东方傅长金吴捷刘俊
Owner NANJING LIFECARE PHARM CO LTD
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