Optimization and structure-activity relationship of a series of 1-phenyl-1,8-naphthyridin-4-one-3-carboxamides: identification of MK-0873, a potent and effective PDE4 inhibitor

Bioorg Med Chem Lett. 2008 Oct 15;18(20):5554-8. doi: 10.1016/j.bmcl.2008.09.009. Epub 2008 Sep 6.

Abstract

A SAR study of a series of 1-phenyl-1,8-naphthyridin-4-one-3-carboxamides is described. Optimization of the series was based on in vitro potency against PDE4, inhibition of the LPS-induced production of TNF-alpha in human whole blood and minimizing affinity for the hERG potassium channel. From these studies, compounds 18 and 20 (MK-0873) were identified as optimized PDE4 inhibitors with good overall in vitro and in vivo profiles and selected as development candidates.

MeSH terms

  • Animals
  • Chemistry, Pharmaceutical / methods*
  • Cyclic Nucleotide Phosphodiesterases, Type 4 / chemistry*
  • Dogs
  • Drug Design
  • ERG1 Potassium Channel
  • Ether-A-Go-Go Potassium Channels / chemistry
  • Humans
  • Inhibitory Concentration 50
  • Lipopolysaccharides / chemistry
  • Models, Chemical
  • Naphthyridines / chemical synthesis*
  • Naphthyridines / pharmacology
  • Protein Binding
  • Rats
  • Saimiri
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • ERG1 Potassium Channel
  • Ether-A-Go-Go Potassium Channels
  • KCNH2 protein, human
  • Lipopolysaccharides
  • MK 0873
  • Naphthyridines
  • Tumor Necrosis Factor-alpha
  • Cyclic Nucleotide Phosphodiesterases, Type 4