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Thiazole compound (as ppard) ligand and pharmaceutical, cosmetic and health food comprised thereof

A compound, thiazole technology, applied in the fields of thiazole compounds as PPARδ ligands and pharmaceuticals, cosmetics and health foods containing them, can solve the problems that do not mention the pharmacological effects of selective activators

Inactive Publication Date: 2009-12-16
SEOUL NAT UNIV R&DB FOUND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And the document only describes the mass spectrum of the generated racemate for M + +1 value, the racemate consists of 1 H-NMR confirms and acts as a selective activator of PPARδ, but the document does not mention pharmacological effects as a selective activator of PPARδ

Method used

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  • Thiazole compound (as ppard) ligand and pharmaceutical, cosmetic and health food comprised thereof
  • Thiazole compound (as ppard) ligand and pharmaceutical, cosmetic and health food comprised thereof
  • Thiazole compound (as ppard) ligand and pharmaceutical, cosmetic and health food comprised thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Embodiment 1: the preparation of the compound of formula 8 (step A)

[0093] 500 mg (2.14 mmol) of 4-iodo-2-methylphenol were dissolved in anhydrous tetrahydrofuran under nitrogen while maintaining the temperature at 0°C. 1.1 ml of isopropylmagnesium chloride (2M-diethyl ether solution, 2.16 mmol) was slowly added thereto, followed by reaction for 10 minutes. The reaction solution was cooled to -78°C, and 2.77 ml of tert-butyllithium (1.7M-heptane solution, 4.70 mmol) was slowly added thereto. After reacting for 20 minutes, 69 mg of S (2.14 mmol) was added thereto, and then the reaction was continued until the temperature of the reactant reached 15°C. After 40 minutes, 624 mg (2.14 mmol) of 5-chloromethyl-4-methyl-2-[(4-trifluoromethyl)phenyl]-thiazole represented by formula 7 was dissolved in 2 ml of anhydrous THF , at the same temperature (15 ° C) slowly added to the above reactants. After continuing the reaction for one hour, the reaction was terminated by adding ...

Embodiment 2

[0096] Embodiment 2: the preparation of the compound of formula 9 (R 1 =t-Bu(CH 3 ) 2 Si-, step B)

[0097] 500 mg (1.26 mmol) of the compound of formula 8 and 171 mg (2.52 mmol) of imidazole were completely dissolved in 5 ml of dimethylformamide. 209 mg (1.38 mmol) of tert-butyldimethylchlorosilane was slowly added thereto, followed by stirring at room temperature for 4 hours. After the reaction was complete, the organic solvent was extracted with ammonium chloride solution and ethyl acetate. The moisture in the organic phase was dried over magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane / ethyl acetate=10 / 1, v / v) to obtain 610 mg (yield: 95%) of the target compound.

[0098] 1 H NMR (300MHz, CDCl 3 ): 7.97(d, 2H, J=8.1Hz), 7.65(d, 2H, J=8.2Hz), 7.19(d, 1H, J=1.9Hz), 7.07(m, 1H), 6.69(d, 1H, J=8.3Hz), 4.11(s, 2H), 2.21(s, 3H), 2.11(s, 3H), 1.01(s, 9H), 0.2...

Embodiment 3

[0100] Embodiment 3: the preparation of the compound of formula 10 (R 1 =t-Bu(CH 3 ) 2 Si-, step C)

[0101] The compound (R 1 =t-Bu(CH 3 ) 2 -) was dissolved in 5 ml of anhydrous tetrahydrofuran in the presence of nitrogen and the temperature was lowered to -78°C. 619 µl (2.0 M ether solution, 1.24 mmol) of lithium diisopropylamide was slowly added thereto, followed by reaction for 10 minutes. Then, 77 µl (0.65 mmol) of benzyl bromide was added to the reaction solution, followed by stirring at the same temperature (-78°C) for 30 minutes. The reaction was terminated by adding 5 ml of ammonium chloride solution. The moisture in the organic phase was dried over magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane / ethyl acetate=10 / 1, v / v) to obtain 265 mg (yield: 75%) of the target compound.

[0102] 1H NMR (300MHz, CDCl 3 ): δ7.97(d, 2H, J=8.1Hz), 7.65(d, 2H,...

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PUM

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Abstract

The present invention relates to a thiazole compound as a peroxisome proliferator activated receptor d (PPARd) activator or pharmaceutically acceptable salts thereof, and a pharmaceutical composition, a functional cosmetic composition, a health food, health beverages, a food additive and animal feeds containing the same.

Description

technical field [0001] The present invention relates to a thiazole compound represented by formula 1 as a PPARδ (peroxisome proliferator-activated receptor δ) ligand, and a pharmaceutical composition, a cosmetic composition, a health food, a health drink, a food additive and an animal compound containing the same. Feed, the thiazole compound can be used for treating obesity, hyperlipidemia, arteriosclerosis, diabetes, dementia, Alzheimer's disease and Parkinson's disease and for strengthening muscles or improving memory. [0002] [Formula 1] [0003] Background technique [0004] Among various nuclear receptors, it is known that PPAR (peroxisome proliferator-activated receptor) contains three subtypes: PPARα, PPARγ and PPARδ (Nature, 1990, 347, p645-650., Proc. Natl. Acad. Sci. USA 1994, 91, p7335-7359). PPARα, PPARγ, and PPARδ have tissue-specific functions in vivo and are expressed at different sites. PPARα is mainly expressed in human heart, kidney, skeletal muscle ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/26A61K31/426A61P3/00A61P25/28
CPCA61K8/49C07D277/26A61Q19/06A61K31/426A61P21/00A61P25/16A61P25/28A61P3/00A61P3/04A61P3/06A61P39/00A61P43/00A61P9/10A61P3/10
Inventor 姜宪中高在濚黄厚商
Owner SEOUL NAT UNIV R&DB FOUND
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