The discovery of (R)-2-(sec-butylamino)-N-(2-methyl-5-(methylcarbamoyl)phenyl) thiazole-5-carboxamide (BMS-640994)-A potent and efficacious p38alpha MAP kinase inhibitor

Bioorg Med Chem Lett. 2008 Mar 15;18(6):1762-7. doi: 10.1016/j.bmcl.2008.02.031. Epub 2008 Feb 16.

Abstract

A novel structural class of p38alpha MAP kinase inhibitors has been identified via iterative SAR studies of a focused deck screen hit. Optimization of the lead series generated 6e, BMS-640994, a potent and selective p38alpha inhibitor that is orally efficacious in rodent models of acute and chronic inflammation.

MeSH terms

  • Animals
  • Arthritis / drug therapy
  • Caco-2 Cells
  • Cell Membrane Permeability / drug effects
  • Cells, Cultured
  • Crystallography, X-Ray
  • Cytochrome P-450 Enzyme Inhibitors
  • Cytochrome P-450 Enzyme System / metabolism
  • Ether-A-Go-Go Potassium Channels / antagonists & inhibitors
  • Humans
  • Lipopolysaccharides / pharmacology
  • Male
  • Mice
  • Microsomes, Liver / drug effects
  • Mitogen-Activated Protein Kinase 14 / antagonists & inhibitors*
  • Mitogen-Activated Protein Kinase 14 / metabolism
  • Molecular Structure
  • Monocytes / cytology
  • Monocytes / drug effects
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / pharmacokinetics
  • Protein Kinase Inhibitors / pharmacology*
  • Rats
  • Rats, Inbred Lew
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / pharmacokinetics
  • Thiazoles / pharmacology*
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • BMS-640994
  • Cytochrome P-450 Enzyme Inhibitors
  • Ether-A-Go-Go Potassium Channels
  • KCNH1 protein, human
  • Lipopolysaccharides
  • Protein Kinase Inhibitors
  • Thiazoles
  • Tumor Necrosis Factor-alpha
  • Cytochrome P-450 Enzyme System
  • Mitogen-Activated Protein Kinase 14

Associated data

  • PDB/3BX5