Potent N-(1,3-thiazol-2-yl)pyridin-2-amine vascular endothelial growth factor receptor tyrosine kinase inhibitors with excellent pharmacokinetics and low affinity for the hERG ion channel

J Med Chem. 2004 Dec 2;47(25):6363-72. doi: 10.1021/jm049697f.

Abstract

A series of N-(1,3-thiazol-2-yl)pyridin-2-amine KDR kinase inhibitors have been developed that possess optimal properties. Compounds have been discovered that exhibit excellent in vivo potency. The particular challenges of overcoming hERG binding activity and QTc increases in vivo in addition to achieving good pharmacokinetics have been acomplished by discovering a unique class of amine substituents. These compounds have a favorable kinase selectivity profile that can be accentuated with appropriate substitution.

MeSH terms

  • Administration, Oral
  • Aminopyridines / chemical synthesis*
  • Aminopyridines / pharmacokinetics
  • Aminopyridines / pharmacology
  • Animals
  • Biological Availability
  • Cell Line
  • Dogs
  • ERG1 Potassium Channel
  • Electrocardiography / drug effects
  • Ether-A-Go-Go Potassium Channels
  • In Vitro Techniques
  • Lung / enzymology
  • Macaca mulatta
  • Male
  • Mice
  • Microsomes, Liver / metabolism
  • Phosphorylation
  • Potassium Channels, Voltage-Gated / metabolism*
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacokinetics
  • Pyridines / pharmacology
  • Radioligand Assay
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Vascular Endothelial Growth Factor / antagonists & inhibitors*
  • Thiazoles / chemical synthesis*
  • Thiazoles / pharmacokinetics
  • Thiazoles / pharmacology
  • Tissue Distribution
  • Vascular Endothelial Growth Factor Receptor-2 / metabolism

Substances

  • 4-(2-(5-cyanothiazol-2-ylamino)pyridin-4-ylmethyl)piperazine-1-carboxylic acid methylamide
  • Aminopyridines
  • ERG1 Potassium Channel
  • Ether-A-Go-Go Potassium Channels
  • Potassium Channels, Voltage-Gated
  • Pyridines
  • Thiazoles
  • Receptors, Vascular Endothelial Growth Factor
  • Vascular Endothelial Growth Factor Receptor-2