Discovery of INT131: a selective PPARγ modulator that enhances insulin sensitivity

Bioorg Med Chem. 2013 Feb 15;21(4):979-92. doi: 10.1016/j.bmc.2012.11.058. Epub 2012 Dec 10.

Abstract

PPARγ is a member of the nuclear hormone receptor family and plays a key role in the regulation of glucose homeostasis. This Letter describes the discovery of a novel chemical class of diarylsulfonamide partial agonists that act as selective PPARγ modulators (SPPARγMs) and display a unique pharmacological profile compared to the thiazolidinedione (TZD) class of PPARγ full agonists. Herein we report the initial discovery of partial agonist 4 and the structure-activity relationship studies that led to the selection of clinical compound INT131 (3), a potent PPARγ partial agonist that displays robust glucose-lowering activity in rodent models of diabetes while exhibiting a reduced side-effects profile compared to marketed TZDs.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Administration, Oral
  • Animals
  • Binding Sites
  • Crystallography, X-Ray
  • Cytochrome P-450 CYP3A
  • Cytochrome P-450 Enzyme Inhibitors
  • Cytochrome P-450 Enzyme System / metabolism
  • Diabetes Mellitus, Experimental / drug therapy
  • Half-Life
  • Insulin Resistance
  • Male
  • Mice
  • PPAR gamma / agonists*
  • PPAR gamma / metabolism
  • Protein Structure, Tertiary
  • Quinolines / chemistry*
  • Quinolines / pharmacokinetics
  • Quinolines / therapeutic use
  • Rats
  • Rats, Sprague-Dawley
  • Rats, Zucker
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacokinetics
  • Sulfonamides / therapeutic use

Substances

  • Cytochrome P-450 Enzyme Inhibitors
  • INT 131
  • PPAR gamma
  • Quinolines
  • Sulfonamides
  • Cytochrome P-450 Enzyme System
  • Cyp3a2 protein, rat
  • Cytochrome P-450 CYP3A