Discovery of aryl aminoquinazoline pyridones as potent, selective, and orally efficacious inhibitors of receptor tyrosine kinase c-Kit

J Med Chem. 2008 Jun 12;51(11):3065-8. doi: 10.1021/jm800188g. Epub 2008 May 1.

Abstract

Inhibition of c-Kit has the potential to treat mast cell associated fibrotic diseases. We report the discovery of several aminoquinazoline pyridones that are potent inhibitors of c-Kit with greater than 200-fold selectivity against KDR, p38, Lck, and Src. In vivo efficacy of pyridone 16 by dose-dependent inhibition of histamine release was demonstrated in a rodent pharmacodynamic model of mast cell activation.

MeSH terms

  • Administration, Oral
  • Animals
  • Crystallography, X-Ray
  • Histamine Release / drug effects
  • Mast Cells / drug effects
  • Mast Cells / metabolism
  • Models, Molecular
  • Molecular Structure
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / pharmacokinetics
  • Protein Kinase Inhibitors / pharmacology
  • Proto-Oncogene Proteins c-kit / metabolism*
  • Pyridones / chemical synthesis*
  • Pyridones / pharmacokinetics
  • Pyridones / pharmacology
  • Quinazolines / chemical synthesis*
  • Quinazolines / pharmacokinetics
  • Quinazolines / pharmacology
  • Rats
  • Structure-Activity Relationship

Substances

  • Protein Kinase Inhibitors
  • Pyridones
  • Quinazolines
  • Proto-Oncogene Proteins c-kit