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PPAR alpha/gamma dual agonist and its application

A dual agonist and compound technology, which is applied in the field of medicine, can solve the problem of single effect and achieve the effect of promoting fat cell differentiation, increasing mRNA level, and lowering blood sugar level

Inactive Publication Date: 2014-10-22
SHANGHAI UNIV OF T C M
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In terms of the treatment of metabolic syndrome, the hypoglycemic drugs or lipid-lowering drugs currently used in clinical practice have single effects, and none of them have the effects of lowering blood lipids and blood sugar at the same time. New drugs that have both effects at the same time are expected in clinical practice

Method used

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  • PPAR alpha/gamma dual agonist and its application
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  • PPAR alpha/gamma dual agonist and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Preparation of psoralen flavone methyl ether (compound of formula A)

[0030] 10.0kg of psoralen medicinal material was reflux extracted with 8 times the volume (80L) of ethanol aqueous solution with a volume fraction of 95%, refluxed for 2 hours each time, refluxed and extracted 3 times in total, combined extracts, concentrated under reduced pressure to obtain extract (approx. 800mL); add 1 times the amount (800mL) of water to the extract to suspend, then extract with petroleum ether (1000mL×3) and ethyl acetate (1000mL×3) in sequence, and collect the ethyl acetate extract; recover under reduced pressure Carry out silica gel column chromatography after ethyl acetate, and carry out gradient elution with petroleum ether and ethyl acetate successively (10:1-1:5); Apply the obtained fraction to silica gel column chromatography: use cyclohexane-acetone gradient first Elution (9:1-1:1), then use reverse column chromatography methanol-water gradient elution (60% me...

Embodiment 2

[0035] Embodiment 2: the preparation of formula B compound

[0036] Take 20mg of psoralen dihydroflavone [English name is bavachin, also isolated from psoralen herb, the method of obtaining it can be found in the literature Bioorg.Med.Chem.2004,12:4387-4392.] dissolved in 1mL of pyridine, and then Add 1 mL of acetic anhydride, let stand at room temperature for 24 hours, then add 10 mL of ethyl acetate solvent, back-extract with water, collect the organic phase, concentrate, and perform Sephadex LH-20 column chromatography to obtain the compound of formula B as a white powder.

[0037] 1 H-NMR (CDCl 3 ,400MHz)δ:1.72(3H,s,CH3-5''),1.77(3H,s,CH3-4''),2.34(6H,s,2×CH 3CO),2.88(1H,dd,J=2.8,16.8Hz,H-3),3.06(1H,dd,J=13.2,16.8Hz,H-3),3.23(2H,d,J=7.2Hz, H-1''),5.22(1H,m,H-2''),5.49(1H,dd,J=2.8,13.2Hz,H-2),6.80(1H,s,H-8),7.18 (2H,d,J=8.4Hz,H-3',5'),7.51(2H,d,J=8.4Hz,H-2',6'),7.82(1H,s,H-5).

Embodiment 3

[0038] Embodiment 3: the preparation of formula C compound

[0039] Dissolve 20mg of psoralen dihydroflavone methyl ether [compound of formula A] in 1mL of pyridine, then add 1mL of acetic anhydride, let stand at room temperature for 24h, then add 10mL of ethyl acetate solvent, back-extract with water, collect the organic phase, concentrate, Sephadex LH-20 column chromatography, the compound of formula C is obtained as white powder.

[0040] 1 H-NMR (CDCl 3 ,400MHz)δ:1.72(3H,s,CH3-5''),1.76(3H,s,CH3-4''),2.35(3H,s,CH3CO),2.83(1H,dd,J=2.8, 16.8Hz,H-3),3.04(1H,dd,J=13.2,16.8Hz,H-3),3.27(2H,d,J=7.2Hz,H-1''),3.88(3H,s, OCH3),5.29(1H,m,H-2''),5.47(1H,dd,J=2.8,13.2Hz,H-2),6.47(1H,s,H-8),7.18(2H,d ,J=8.4Hz,H-3',5'),7.52(2H,d,J=8.4Hz,H-2',6'),7.70(1H,s,H-5).

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Abstract

The present invention discloses a PPAR α / γ dual agonist and its application. The PPAR α / γ dual agonist comprises an effective amount of the compounds represented by formula I or / and its pharmaceutically acceptable derivative. Wherein, R1is selected from alkoxyl or ester group; R2 is selected from hydroxyl or ester group. The PPAR α / γ dual agonist according to the present invention can be used for preparing drugs and functional foods for preventing or / and treating metabolic syndrome, especially glucose or / and lipid disorders, with extensive and bright prospects of application.

Description

technical field [0001] The invention relates to a PPARα / γ dual agonist and application thereof, belonging to the technical field of medicine. Background technique [0002] Metabolic syndrome is a common disease characterized by abnormal glucose and lipid metabolism, accompanied by elevated low-density lipoprotein and low high-density lipoprotein cholesterol. The common symptoms are obesity, diabetes, hyperlipidemia and atherosclerosis Among them, diabetic patients often have hyperlipidemia, cardiovascular disease, diabetic nephropathy, diabetic neuropathy and other diseases. [0003] According to the World Health Organization, more than 220 million people worldwide suffer from diabetes. Among them, China has become the country with the largest number of diabetics in the world, with a total of 92 million diabetics. According to the "New England Journal of Medicine" published on March 25, 2010 According to the data of the research report, there are currently more than 92 milli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/32A61K31/352A61P3/10A61P3/04A61P3/06A61P9/10A23L1/30
CPCC07D311/32A23L33/10A23V2002/00A61K31/353A61P3/04A61P3/06A61P3/10A61P9/10A23V2200/328
Inventor 郭夫江黄诚冯丽李医明
Owner SHANGHAI UNIV OF T C M
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