Discovery of novel pyrazole-containing benzamides as potent RORγ inverse agonists

Bioorg Med Chem Lett. 2015 Aug 1;25(15):2985-90. doi: 10.1016/j.bmcl.2015.05.028. Epub 2015 May 22.

Abstract

The nuclear receptor RORγ plays a central role in controlling a pro-inflammatory gene expression program in several lymphocyte lineages including TH17 cells. RORγ-dependent inflammation has been implicated in the pathogenesis of several major autoimmune diseases and thus RORγ is an attractive target for therapeutic intervention in these diseases. Starting from a lead biaryl compound 4a, replacement of the head phenyl moiety with a substituted aminopyrazole group resulted in a series with improved physical properties. Further SAR exploration led to analogues (e.g., 4j and 5m) as potent RORγ inverse agonists.

Keywords: Autoimmune disease; IL-17; Inflammation; RORγ inverse agonist; Th17 cell.

MeSH terms

  • Animals
  • Autoimmune Diseases / drug therapy
  • Autoimmune Diseases / immunology
  • Benzamides / chemistry*
  • Benzamides / pharmacology*
  • Drug Inverse Agonism*
  • Humans
  • Interleukin-17 / immunology
  • Mice
  • Models, Molecular
  • Nuclear Receptor Subfamily 1, Group F, Member 3 / antagonists & inhibitors*
  • Nuclear Receptor Subfamily 1, Group F, Member 3 / chemistry
  • Nuclear Receptor Subfamily 1, Group F, Member 3 / immunology
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacology*
  • Spleen / cytology
  • Spleen / drug effects
  • Spleen / immunology
  • Th17 Cells / drug effects
  • Th17 Cells / immunology

Substances

  • Benzamides
  • Interleukin-17
  • Nuclear Receptor Subfamily 1, Group F, Member 3
  • Pyrazoles
  • pyrazole
  • benzamide