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Phenoxyacetic acid derivative, preparation process thereof and use thereof as medicaments

A compound and alkyl technology, applied in the field of phenoxyacetic acid derivatives, their preparation and their use as medicines, can solve problems such as side effects, edema side effects, hypoglycemia and weight gain

Inactive Publication Date: 2015-02-04
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing methods for the treatment of diabetes all have certain defects.
Examples include insulin injections and sulfonylureas, which may cause hypoglycemia and weight gain; metformin, alpha-glucosidase inhibitors, and GLP-1 analogs, which may cause gastrointestinal side effects; PPAR-γ agonists, which may cause weight gain and edema side effects; DPP-IV inhibitors may cause suprapharyngitis, headache and infection side effects

Method used

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  • Phenoxyacetic acid derivative, preparation process thereof and use thereof as medicaments
  • Phenoxyacetic acid derivative, preparation process thereof and use thereof as medicaments
  • Phenoxyacetic acid derivative, preparation process thereof and use thereof as medicaments

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] 2-(4-((2′,6′-Dimethyl-4′-(3-(methylsulfonyl)propyl)-[1,1′-biphenyl]-3-)methoxy) Phenoxy)acetic acid (I-1)

[0100]

[0101]

[0102] Compound IV (200mg, 0.49mmol) was dissolved in 10mL acetone, and K was added sequentially 2 CO 3 (134mg, 0.97mmol), catalytic amount of KI and compound V-1 (88mg, 0.49mmol), heated and refluxed overnight, after the reaction, filtered, and the filtrate was concentrated under reduced pressure. The residue was separated by silica gel column chromatography (eluent system: petroleum ether and ethyl acetate) to obtain the target product VI-1 (210 mg, white solid), yield: 84.3%.

[0103] Compound VI-1 (200mg, 0.39mmol) was dissolved in 6mL of tetrahydrofuran, methanol and water (2:3:1) three-component solvent, 2M sodium hydroxide solution (0.78mL, 1.56mmol) was added, and the reaction was stirred at room temperature for 2h After the reaction is over, add 10 mL of water, add 1M hydrochloric acid dropwise to the reaction solution pH 3, extract with eth...

Embodiment 2

[0106] 2-(4-((2′,6′-Dimethyl-4′-(3-(methylsulfonyl)propyl)-[1,1′-biphenyl]-3-)methoxy) 2-methylphenoxy)acetic acid (I-2)

[0107]

[0108] Compound IV (200mg, 0.49mmol) was dissolved in 10mL acetone, and K was added sequentially 2 CO 3 (134 mg, 0.97 mmol), catalytic amount of KI and compound V-2 (95 mg, 0.49 mmol), heated and refluxed overnight, after the reaction was completed, filtered, and the filtrate was concentrated under reduced pressure. The residue was separated by silica gel column chromatography (eluent system: petroleum ether and ethyl acetate) to obtain the target product VI-2 (180 mg, white solid), yield: 70.3%.

[0109] Compound VI-2 (170mg, 0.32mmol) was dissolved in 6mL of tetrahydrofuran, methanol and water (2:3:1) three-component solvent, 2M sodium hydroxide solution (0.64mL, 1.28mmol) was added, and the reaction was stirred at room temperature for 2h After the reaction is over, add 10 mL of water, add 1M hydrochloric acid dropwise to the reaction solution pH 3,...

Embodiment 3

[0112] 2-(2-Chloro-4-((2′,6′-dimethyl-4′-(3-(methylsulfonyl)propyl)-[1,1′-biphenyl]-3- )Methoxy)phenoxy)acetic acid (I-3)

[0113]

[0114] Compound IV (200mg, 0.49mmol) was dissolved in 10mL acetone, and K was added sequentially 2 CO 3 (134mg, 0.97mmol), catalytic amount of KI and compound V-3 (105mg, 0.49mmol), heated and refluxed overnight, after the reaction was over, filtered, and the filtrate was concentrated under reduced pressure. The residue was separated by silica gel column chromatography (eluent system: petroleum ether and ethyl acetate) to obtain the target product VI-3 (220 mg, white solid), yield: 82.7%.

[0115] Compound VI-3 (210mg, 0.40mmol) was dissolved in 6mL tetrahydrofuran, methanol and water (2:3:1) three-component solvent, 2M sodium hydroxide solution (0.79mL, 1.58mmol) was added, and the reaction was stirred at room temperature for 2h After the reaction is over, add 10 mL of water, add 1M hydrochloric acid dropwise to the reaction solution pH 3, extract w...

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PUM

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Abstract

The invention discloses a phenoxyacetic acid derivative, a preparation process thereof and use thereof as medicaments, and provides a compound shown as formula (I) and a physiologically acceptable salt thereof, wherein the symbols are as defined in the specification. The compound or physiologically acceptable salt thereofhas GPR40 (G-protein-coupled receptor) regulation function, can cause increase in insulin release, and is useful to be used as an insulin secretagogue or medicaments for prevention or treatment of diabetes and the like.

Description

Technical field [0001] The present invention relates to a new phenoxyacetic acid derivative, its preparation method, and a pharmaceutical combination group containing the derivative, and its use as a therapeutic agent, especially as a GPR40 agonist and in the preparation of drugs for the treatment of diseases such as diabetes and metabolic disorders the use of. Background technique [0002] Diabetes is a disease of energy metabolism, divided into type 1 diabetes (insulin-dependent diabetes) and type 2 diabetes (non-insulin-dependent diabetes). At present, there are about 366 million diabetic patients in the world, accounting for 6.4% of the world's population. Among them, type 2 diabetic patients account for about 90-95% of the total number of diabetic patients. [0003] Diabetes can be treated with dietary regulation and exercise. When these cannot relieve symptoms, medications are needed. Current drug treatments for diabetes include: biguanides such as metformin, which can red...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/18C07C59/70C07C235/20A61K31/192A61P3/10A61P3/00
Inventor 黄文龙钱海王学堃崔建戴雨轩李政赵天笑
Owner CHINA PHARM UNIV
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