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Sulfonyl-substituted bicyclic compounds as modulators of ppar
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A kind of compound, alkyl technology, applied in the field of sulfonyl-substituted bicyclic aryl derivatives
Active Publication Date: 2013-08-21
KALYPSYS INC
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Interestingly, transcription of PPAR-γ target genes for lipid storage and lipogenesis was not altered
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[0266] Indanyl-2-acetic acid methyl ester (1.0 g, 5.26 mmol) was added to a stirred chlorosulfonic acid solution (5 mL) at 0°C. The solution was stirred at 0°C for 0.5 hours, then at room temperature for 3 hours. The resulting solution was poured slowly on ice and extracted with ether (3 x 100 mL). dry (Na 2 SO 4 ) and concentration of the combined organic layers gave a mixture of methyl 5-chlorosulfonyl-indane-2-acetate and methyl 4-chlorosulfonyl-indane-2-acetate (1.38 g, 4.78 mmol, 91%). This mixture of sulfonyl chlorides was used in the next step without further purification. The mixture of sulfonyl chlorides (370 mg, 1.28 mmol) was dissolved in anhydrous THF (10 mL). 1-(4-Trifluoromethylphenyl)piperazine (315 mg, 1.37 mmol), triethylami...
Embodiment 2
[0271]
[0272] {4-[4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-indan-2-yl}-acetic acid: according to the method of Example 1 using Example 1 Step 1 {4-[4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-indan-2-yl}-acetic acid methyl ester synthetic compound {4-[4-(4-tri Fluoromethyl-phenyl)-piperazine-1-sulfonyl]-indan-2-yl}-acetic acid. 1 H NMR (400MHz, MeOH-d 4 )δ7.60(d, 1H), 7.52(d, 2H), 7.51(d, 1H), 7.31(t, 1H), 7.15(d, 2H), 3.53(dd, 1H), 3.42(m, 4H ), 3.25(m, 4H), 3.20(m, 1H), 3.00(dd, 1H), 2.87(m, 1H), 2.72(m, 1H), 2.47(m, 2H); LCMS: 468.8(M+ 1) + .
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Abstract
The present invention discloses compounds that are modulators of peroxisome proliferator-activated receptors (PPARs), pharmaceutical compositions containing them, and methods of using them to treat diseases.
Description
[0001] This application claims priority to US Provisional Applications 60 / 623,252 and 60 / 679,813, which are hereby incorporated by reference as if written herein. technical field [0002] The present invention relates to novel sulfonyl-substituted bicyclic aryl derivatives and the use of these compounds to modulate nuclear receptor-mediated processes, particularly peroxisome proliferator-activated receptor (PPAR)-mediated processes for the treatment of approach to various diseases. Background technique [0003] Peroxisome proliferators are a structurally diverse group of compounds that, when administered to mammals, cause a marked increase in the size and number of hepatic and renal peroxisomes, as well as concomitant depletion of enzymes required for cycling through beta-oxidation Increased expression improves the ability of peroxisomes to metabolize fatty acids. (Lazarow and Fujiki, Ann, Rev. Cell Biol. 1:489-530 (1985); Vamecq and Draye, Essays Biochem. 24:1115-225 (1989...
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