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PPARgamma/delta dual agonist, preparation method thereof and application of PPARgamma/delta dual agonist as medicine

A compound and alkyl technology, applied in the field of medicine, can solve the problems of PPARγ/δ dual agonists that have not been reported in the literature

Active Publication Date: 2020-06-16
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, PPARα / γ dual agonists, PPARα / γ / δ pan-agonists and PPARα / δ dual agonists have been reported in a large number of literatures, but so far there has been no literature report on PPARγ / δ dual agonists

Method used

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  • PPARgamma/delta dual agonist, preparation method thereof and application of PPARgamma/delta dual agonist as medicine
  • PPARgamma/delta dual agonist, preparation method thereof and application of PPARgamma/delta dual agonist as medicine
  • PPARgamma/delta dual agonist, preparation method thereof and application of PPARgamma/delta dual agonist as medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] (Z)-2-(4-((6-methoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)-2,6-dimethylphenoxy)acetic acid ( I-1)

[0087]

[0088] 6-Methoxy-3-benzofuranone 1a (1.0g, 6.1mmol) and methyl 2-(4-formyl-2,6-dimethylphenoxy)acetate 2a (1.3g, 6.1mmol ) was dissolved in ethanol / DMF (20mL, 1:1, v / v) mixed solvent, and 2.3mL of 50% KOH aqueous solution was added dropwise at room temperature, and the solution was reacted at room temperature for 4 hours. After the reaction was detected by TLC, the reaction solution was poured into 30mL of water , adjusted the pH to 1-2 with concentrated hydrochloric acid under vigorous stirring, suction filtered after cooling, washed the filter cake with a small amount of cold water, recrystallized with methanol / DMF (1:1, v / v) to obtain 1.2 g of light yellow crystals, and the yield was 56 %.

[0089] 1 H NMR (300MHz, DMSO-d 6 )δ: 7.75-7.62(m, 3H), 7.13(d, J=1.9Hz, 1H), 6.86, 6.83(dd, J=8.6, 2.0Hz, 1H), 6.69(s, 1H), 4.45(s , 2H), 3.94(s, 3H), 2.31(s, 6H)....

Embodiment 2

[0091] (Z)-2-(4-((6-ethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)-2,6-dimethylphenoxy)acetic acid ( I-2)

[0092]

[0093] Referring to the preparation method of I-1, 0.64 g of light yellow crystals was obtained with a yield of 50%.

[0094] 1 H NMR (300MHz, DMSO-d 6 )δ: 7.76-7.62(m, 3H), 7.08(s, 1H), 6.81(d, J=8.5Hz, 1H), 6.68(s, 1H), 4.45(s, 2H), 4.22(q, J =6.8Hz, 2H), 2.31(s, 6H), 1.39(t, J=6.8Hz, 3H). 13 C NMR (75MHz, DMSO-d 6 )δ: 181.97, 170.40, 168.41, 167.02, 157.19, 147.18, 132.37, 131.50, 128.20, 114.31, 112.32, 109.64, 100.35, 69.37, 65.04, 16.61, 14.78. - .Anal.calcd.For C 21 h 20 o 6 : C, 68.47; H, 5.47; Found: C, 68.62; H, 5.31.

Embodiment 3

[0096] (Z)-2-(4-((6-propoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)-2,6-dimethylphenoxy)acetic acid ( I-3)

[0097]

[0098] Referring to the preparation method of I-1, 0.49 g of light yellow crystals was obtained with a yield of 35%.

[0099] 1 H NMR (300MHz, DMSO-d 6 )δ: 7.76-7.63(m, 3H), 7.11(d, J=1.6Hz, 1H), 6.84, 6.81(dd, J=8.5, 1.8Hz, 1H), 6.69(s, 1H), 4.45(s , 2H), 4.12(t, J=6.5Hz, 2H), 2.31(s, 6H), 1.85-1.73(m, 2H), 1.01(t, J=7.4Hz, 3H). 13 C NMR (75MHz, DMSO-d 6 )δ: 181.93, 170.42, 167.20, 162.52, 157.15, 147.20, 132.37, 131.53, 128.32, 114.31, 112.32, 109.64, 99.99, 70.77, 65.04, 22.25, 16.63, 10.18. - .Anal.calcd.For C 22 h 22 o 6 : C, 69.10; H, 5.80; Found: C, 69.35; H, 5.71.

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Abstract

The invention relates to a novel PPAR gamma / delta dual agonist as shown in a general formula (I) which is described in the specification, a preparation method thereof and an application of a pharmaceutical composition containing the derivative in preparation of drugs for preventing or / and treating glucose metabolic disorder or / and lipid metabolic disorder diseases. The PPAR gamma / delta dual agonist has excellent in-vivo hypoglycemic activity and blood fat regulating effect, can be applied to preparation of drugs for preventing or / and treating metabolic syndrome related diseases such as diabetes, obesity, hyperlipidemia, atherosclerosis, fibrosis and fatty liver, and has a wide application prospect.

Description

technical field [0001] The invention relates to a class of PPARγ / δ dual agonists, a preparation method and application thereof, and belongs to the technical field of medicine. The derivative structures involved in the present invention are unique and novel in this field. 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, atherosclerosis Cirrhosis and fatty liver, etc. 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 more than 92 million diabetics. More...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/83A61P3/00A61P3/04A61P3/06A61P3/10A61P1/16A61P9/10A61K31/343
CPCA61P1/16A61P3/00A61P3/04A61P3/06A61P3/10A61P9/10C07D307/83
Inventor 张陆勇李政周宗涛
Owner GUANGDONG PHARMA UNIV
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