Design and synthesis of 6-phenylnicotinamide derivatives as antagonists of TRPV1

Bioorg Med Chem Lett. 2008 Oct 15;18(20):5609-13. doi: 10.1016/j.bmcl.2008.08.105. Epub 2008 Aug 31.

Abstract

6-Phenylnicotinamide (2) was previously identified as a potent TRPV1 antagonist with activity in an in vivo model of inflammatory pain. Optimization of this lead through modification of both the biaryl and heteroaryl components has resulted in the discovery of 6-(4-fluorophenyl)-2-methyl-N-(2-methylbenzothiazol-5-yl)nicotinamide (32; SB-782443) which possesses an excellent overall profile and has been progressed into pre-clinical development.

MeSH terms

  • Administration, Oral
  • Animals
  • Benzothiazoles / chemical synthesis*
  • Benzothiazoles / pharmacology
  • Capsaicin / chemistry
  • Cell Line
  • Chemistry, Pharmaceutical / methods*
  • Drug Design
  • Guinea Pigs
  • Humans
  • Inflammation
  • Inhibitory Concentration 50
  • Models, Chemical
  • Niacinamide / analogs & derivatives*
  • Niacinamide / chemical synthesis*
  • Niacinamide / chemistry
  • Niacinamide / pharmacology
  • Rats
  • TRPV Cation Channels / antagonists & inhibitors*
  • TRPV Cation Channels / chemistry*

Substances

  • 6-(4-fluorophenyl)-2-methyl-N-(2-methylbenzothiazol-5-yl)nicotinamide
  • Benzothiazoles
  • TRPV Cation Channels
  • TRPV1 protein, human
  • Niacinamide
  • Capsaicin