57330-37-7Relevant articles and documents
Practical, highly convergent, asymmetric synthesis of a selective PPARγ modulator
Maligres, Peter E.,Humphrey, Guy R.,Marcoux, Jean-Francois,Hillier, Michael C.,Zhao, Dalian,Krska, Shane,Grabowski, Edward J.J.
experimental part, p. 525 - 534 (2010/04/22)
A practical, highly convergent, asymmetric synthesis of a selective PPARγ modulator 1 is described. The inhibitor contains two key components, a 6-trifluoromethoxy-3-acylindole (6) and (R)-raryloxybutanoic acid derivative (10). Twomethods were developed to overcome the regioselectivity issues encountered in the preparation of the 6-substituted indole. The first involved an intramolecular Heck reaction of an iodoaryl enamine. The second involved application of a catalytic Meerwein arylation reaction between 2-nitro-4-trifluoromethoxyaniline and isopropenyl acetate and subsequent reductive cyclization. The α-aryloxybutanoic acid was prepared via an asymmetric hydrogenation of the corresponding α-aryloxy-α,β- unsaturated acid. Tetrabutylammonium iodidecatalyzed coupling of the two fragments and ester hydrolysis completed the convergent synthesis. The described convergent synthesis was used to prepare >3 kg of drug substance 1 in 50% overall yield and with >99.5% ee.
INDOLES HAVING ANTI-DIABETIC ACTIVITY
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Page/Page column 29, (2008/06/13)
Indoles of Formula (I) having -X-aryl-(CH2)x#191-oxazolidinedione and -X-heteroaryl-(CH2)X-oxazolidinedione substituents on the N atom of the indole ring, where x is 0 or 1, and -X-is a bond or -CH2-, and their thiazolidinedione analogs, are PPAR gamma agonists or partial agonists and are useful in the treatment and control of type II diabetes, including hyperglycemia, dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obesity that are often associated with type 2 diabetes.
INDOLES HAVING ANTI-DIABETIC ACTIVITY
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Page 54, (2010/02/06)
Indoles having aryloxyalkanoic acid substituents or arylalkanoic acid substituents are agonists or partial agonists of PPAR gamma and are useful in the treatment and control of hyperglycemia that is symptomatic of type II diabetes, as well as dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obesity that are often associated with type 2 diabetes.