Discovery of selective and orally bioavailable protein kinase Cθ (PKCθ) inhibitors from a fragment hit

J Med Chem. 2015 Jan 8;58(1):222-36. doi: 10.1021/jm500669m. Epub 2014 Jul 7.

Abstract

Protein kinase Cθ (PKCθ) regulates a key step in the activation of T cells. On the basis of its mechanism of action, inhibition of this kinase is hypothesized to serve as an effective therapy for autoimmune diseases such as rheumatoid arthritis (RA), inflammatory bowel disease (IBD), and psoriasis. Herein, the discovery of a small molecule PKCθ inhibitor is described, starting from a fragment hit 1 and advancing to compound 41 through the use of structure-based drug design. Compound 41 demonstrates excellent in vitro activity, good oral pharmacokinetics, and efficacy in both an acute in vivo mechanistic model and a chronic in vivo disease model but suffers from tolerability issues upon chronic dosing.

Publication types

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

MeSH terms

  • Administration, Oral
  • Animals
  • Area Under Curve
  • Arthritis, Experimental / drug therapy
  • Biological Availability
  • Cells, Cultured
  • Chromatography, Liquid
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Drug Design
  • Drug Discovery
  • Female
  • Humans
  • Isoenzymes / antagonists & inhibitors*
  • Isoenzymes / chemistry*
  • Isoenzymes / metabolism
  • Mass Spectrometry
  • Mice, Inbred BALB C
  • Mice, Inbred DBA
  • Models, Molecular
  • Molecular Structure
  • Protein Binding
  • Protein Kinase C / antagonists & inhibitors*
  • Protein Kinase C / chemistry*
  • Protein Kinase C / metabolism
  • Protein Kinase C-theta
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / pharmacokinetics
  • Protein Kinase Inhibitors / pharmacology*
  • Protein Structure, Tertiary
  • Rats
  • Small Molecule Libraries / chemistry
  • Small Molecule Libraries / pharmacokinetics
  • Small Molecule Libraries / pharmacology
  • T-Lymphocytes / drug effects

Substances

  • Isoenzymes
  • Protein Kinase Inhibitors
  • Small Molecule Libraries
  • PRKCQ protein, human
  • Protein Kinase C
  • Protein Kinase C-theta