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Benzofuran derivative, its preparation method and its application in medicine

A technology of pharmacy and compound, which is applied in the field of benzofuran derivatives, its preparation and its application in medicine, and can solve problems such as increasing the burden on diabetic patients

Inactive Publication Date: 2017-05-03
SICHUAN HAISCO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above hypoglycemic drugs have side effects, such as hypoglycemia, weight gain, cardiovascular risk and urogenital infection (Vinod S. Deshmukh et al. (2013). International Journal of Basic & Clinical Pharmacology, 2, 4-11), these Side effects further increase the burden on diabetic patients, therefore, it is necessary to develop a new generation of hypoglycemic drugs with novel mechanisms of action

Method used

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  • Benzofuran derivative, its preparation method and its application in medicine
  • Benzofuran derivative, its preparation method and its application in medicine
  • Benzofuran derivative, its preparation method and its application in medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0468] 2-(6-((3-(3-methoxy-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-5-yl)benzyl)oxy)-2 , 3-dihydrobenzofuran-3-yl)acetic acid (compound 1)

[0469] 2-(6-((3-(3-methoxy-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-5-yl)benzyl)oxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

[0470]

[0471] The first step: 5-bromo-3-methoxy-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran (1a)

[0472] 5-bromo-3-methoxy-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran

[0473]

[0474] In an anhydrous and oxygen-free atmosphere, add sodium hydride (48 mg, 1.99 mmol) to 5-bromo-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-3-ol under an ice-water bath 2G (450 mg, 1.66 mmol) in dry tetrahydrofuran (15 mL), stirred for 20 minutes. Iodomethane (471 mg, 3.32 mmol) was added to the mixture, and the mixture was raised to room temperature for 1 hour. After the reaction was completed, saturated aqueous ammonium chloride (15 mL) was added to quench the reaction, water (25 mL) was added, and extracted with ethyl aceta...

Embodiment 2

[0496] 2-(6-((3-(3-ethoxy-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-5-yl)benzyl)oxy)-2 , 3-dihydrobenzofuran-3-yl)acetic acid (compound 2)

[0497] 2-(6-((3-(3-ethoxy-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-5-yl)benzyl)oxy)-2,3-dihydrobenzofur an-3-yl) acetic acid

[0498]

[0499] The first step: 5-bromo-3-ethoxy-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran (2a)

[0500] 5-bromo-3-ethoxy-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran

[0501]

[0502] In an anhydrous and oxygen-free atmosphere, add sodium hydride (80 mg, 3.32 mmol) to 5-bromo-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-3-ol 2G under ice-cooling (750mg, 2.76mmol) in dry tetrahydrofuran (20mL) and stirred for 20 minutes. Ethyl iodide (0.45 mL, 3.52 mmol) was added to the mixture, raised to room temperature for 5 hours, heated to reflux for 2 hours, and the reaction was completed. Add water (20 mL) to dilute the reaction solution, add saturated aqueous ammonium chloride solution (10 mL), and extract with ethy...

Embodiment 3

[0524] 2-(6-((3-(3-(2-methoxyethyl)-4,6-dimethyl-2,3-dihydrobenzofuran-5-yl)benzyl)oxy)- 2,3-Dihydrobenzofuran-3-yl)acetic acid (compound 3)

[0525] 2-(6-((3-(3-(2-methoxyethyl)-4,6-dimethyl-2,3-dihydrobenzofuran-5-yl)benzyl)oxy)-2,3-dihydroben zofuran-3-yl) acetic acid

[0526]

[0527] The first step: 2-(5-bromo-4,6-dimethylbenzofuran-3-yl)acetonitrile (3a)

[0528] 2-(5-bromo-4,6-dimethylbenzofuran-3-yl)acetonitrile

[0529]

[0530] In an anhydrous and oxygen-free atmosphere, slowly add diethoxy cyanomethyl phosphate (1.1 g, 6.22 mmol) dropwise to a solution of sodium hydride (149 mg, 6.22 mmol) in tetrahydrofuran (20 mL) at 0°C, and stir for 10 minutes , 5-bromo-4,6-dimethylbenzofuran-3(2H)-one 2E (1.0g, 4.15mmol) tetrahydrofuran solution was slowly added dropwise to the mixture, raised to 35°C and continued to stir for 3 hours . Add saturated ammonium chloride solution (20mL) and water (20mL) to the reaction solution, extract with ethyl acetate (20mL×3), comb...

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Abstract

Disclosed is a benzofuran derivative, its preparation method and its application in medicine, specifically related to the compound represented by the general formula (I) or its stereoisomer, hydrate, solvate, co-crystal, A pharmaceutically acceptable salt or prodrug, a preparation method thereof, a pharmaceutical composition comprising the same, and the use of the compound or the pharmaceutical composition in medicine, especially as a GPR40 receptor (G protein-coupled receptor) agonist, Wherein the definition of each substituent in the general formula (I) is the same as the definition in the description.

Description

technical field [0001] The present invention relates to a benzofuran derivative, its preparation method and its application in medicine, in particular to a novel benzofuran derivative with function regulating function of G protein-coupled receptor 40 (GPR40) receptor Or its stereoisomer, hydrate, solvate, co-crystal, pharmaceutically acceptable salt or prodrug, its preparation method and its pharmaceutical composition and its application in medicine. Background technique [0002] Diabetes and its complications have seriously affected people's quality of life and become one of the important causes of death. Excessively high blood sugar levels in diabetes lead to typical symptoms of polyuria, polydipsia and polyphagia in patients. Complications of diabetes such as Kidney damage, diabetic ketoacidosis, and heart disease can be life-threatening. Type II diabetes is the most common type of diabetes, mainly occurs in adulthood, mainly manifested as insufficient insulin secretion ...

Claims

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Application Information

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IPC IPC(8): C07D307/83C07D307/88C07D307/79C07D307/94A61K31/343A61P3/10A61P3/00A61P9/12A61P7/00A61P13/12A61P5/50A61P17/00A61P27/02
CPCC07D307/79C07D307/80C07D307/82C07D307/83C07D307/94A61P3/00A61P3/10A61P5/50A61P7/00A61P9/12A61P13/12A61P17/00A61P27/02
Inventor 张晨王健民何平雷鸣叶飞魏用刚邓炳初
Owner SICHUAN HAISCO PHARMA CO LTD
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