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Aryl compounds as ppar ligands and their use

A kind of compound, the technology of ester compound, be used in the aryl compound as PPAR ligand and its use field

Inactive Publication Date: 2009-12-02
SEOUL NAT UNIV R&DB FOUND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, PPARδ activity elicited by all ligands developed so far can only be generated by 30%–40% of the total ligand-binding pocket.

Method used

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  • Aryl compounds as ppar ligands and their use
  • Aryl compounds as ppar ligands and their use
  • Aryl compounds as ppar ligands and their use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Embodiment 1: preparation compound S1

[0098] [Process A]

[0099] 468 mg (2 mmol) of 4-iodo-2-methylphenol were dissolved in 20 ml of anhydrous tetrahydrofuran in the presence of nitrogen while maintaining the temperature at 0°C. 1.5 ml of isopropylmagnesium chloride (2M) was slowly added thereto, followed by reaction for 10 minutes. The reaction solution was cooled to -78°C, and 2.00 ml of tert-butyllithium (1.7M hexane solution, 1.0 equivalent) was slowly added thereto. After stirring for 10 minutes, 64 mg (2 mmol, 1.0 equivalent) of solid S (sulfur) was added thereto at the same temperature in one portion. The reaction was continued for 40 minutes at an elevated temperature of 15°C. Dissolve 541 mg (2 mmol, 1.0 equivalent) of 4-chloromethyl-4'-trifluoromethyl-biphenyl of formula (III) in 10 ml of anhydrous THF, and slowly add it to the above reactant at the same temperature middle. After reacting for another hour, ammonium chloride solution was used to termi...

Embodiment 2

[0101] Embodiment 2: preparation compound S2

[0102] [Process B]

[0103] 748 mg (2 mmol) of compound S1 and 290 mg (2.0 equivalents) of imidazole were completely dissolved in 20 ml of dimethylformamide. 165 mg (1.1 equivalents) of tert-butyldimethylchlorosilane was slowly added thereto, followed by stirring at room temperature for 4 hours. After the reaction was completed, the organic solvent was extracted using ammonium chloride solution and ethyl acetate. Moisture in the organic layer was dried using magnesium sulfate. Purification was performed using a silica gel column, and the solvent was distilled off under reduced pressure to obtain 928 mg (yield: 95%) of the target compound.

[0104] 1 H NMR (300MHz, CDCl 3 )δ7.67(s, 4H), δ7.50(d, 2H), δ7.27(t, 2H), δ7.13(s, 1H), δ7.05(q, 1H), δ6.66( d, 1H), δ4.04(s, 2H), δ2.15(s, 3H), δ1.01(s, 9H), δ0.20(s, 6H).

Embodiment 3

[0105] Embodiment 3: preparation compound S3

[0106] [Process C]

[0107] 977 mg (2 mmol) of compound S2 was dissolved in 20 ml of anhydrous tetrahydrofuran, and the temperature was lowered to -78°C. 3.6 ml (1.8 M, 2.0 equivalents) of lithium diisopropylamide (LDA) was slowly added thereto. Then, 274 µl (2.0 mmol) of benzyl bromide was added to the reaction solution, and the temperature was slowly raised to room temperature. After reacting for another 30 minutes, ammonium chloride solution was used to terminate the reaction, ethyl acetate and sodium chloride solution were used to extract the organic solvent, and magnesium sulfate was used to dry to remove moisture in the organic layer. After filtration, the solvent was distilled off under reduced pressure, and the residue was further treated by silica gel column chromatography to obtain 961 mg (yield: 83%) of the target compound.

[0108] 1 H NMR (300MHz, CDCl 3 )δ7.67(s, 4H), δ7.47~7.05(m, 11H), δ6.63(d, 1H), δ4.30(m,...

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Abstract

The present invention relates to a compound as a peroxisome proliferator activated receptor (PPAR) activator and a hydrate, a solvate, a stereoisomer and a pharmaceutically acceptable salt thereof, and a pharmaceutical composition, a cosmetic composition, a muscle strengthening agent, a memory improving agent, a therapeutic agent for dementia and Parkinson's disease, a functional food and a feed composition containing the same.

Description

technical field [0001] The present invention relates to compounds represented by formula (I) and hydrates, solvates, stereoisomers and pharmaceutically acceptable salts thereof as PPAR (peroxisome proliferator-activated receptor) ligands, which can be used for Treatment of obesity, hyperlipidemia, arteriosclerosis and diabetes, pharmaceutical composition, cosmetic composition, enhancer, memory improving agent, therapeutic agent for dementia and Parkinson's disease, functional food and feed composition containing them thing. [0002] [Formula I] [0003] Background technique [0004] It is known that among nuclear receptors, PPAR (peroxisome proliferator-activated receptor) has three subtypes, namely 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 and distinct expression regions in vivo. PPARα is mainly expressed in human heart, kidney, skeletal muscle and la...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/20
CPCA23K1/1612C07D261/08A23L1/30C07C323/20C07C391/02C07D213/32A23K20/111A23L33/10A61P3/00A61P3/02A61P3/04A61P3/06A61P3/10A61P9/00A61P9/10A61P21/00A61P25/16A61P25/28A61P43/00A61K31/10
Inventor 姜宪中陈政郁李在桓
Owner SEOUL NAT UNIV R&DB FOUND
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