Cyclic urea derivatives as potent NK1 selective antagonists. Part II: Effects of fluoro and benzylic methyl substitutions

Bioorg Med Chem Lett. 2006 Feb 15;16(4):1065-9. doi: 10.1016/j.bmcl.2005.10.072. Epub 2005 Nov 14.

Abstract

A series of novel five-membered urea derivatives as potent NK1 receptor antagonists is described. The effects of substitution of a 4-fluoro group at the phenyl ring and the introduction of an alpha-methyl group at the benzylic position to improve potency and duration of in vivo activity are discussed. Several compounds with high affinity and sustained in vivo activity were identified.

MeSH terms

  • Animals
  • Anti-Anxiety Agents / chemical synthesis
  • Anti-Anxiety Agents / chemistry*
  • Anti-Anxiety Agents / pharmacology*
  • Benzyl Alcohols / chemistry
  • Crystallography, X-Ray
  • Drug Evaluation, Preclinical
  • Fluorine / chemistry
  • Gerbillinae
  • Models, Molecular
  • Molecular Structure
  • Motor Activity / drug effects
  • Neurokinin-1 Receptor Antagonists*
  • Structure-Activity Relationship
  • Urea / analogs & derivatives*
  • Urea / chemical synthesis
  • Urea / pharmacology*

Substances

  • Anti-Anxiety Agents
  • Benzyl Alcohols
  • Neurokinin-1 Receptor Antagonists
  • Fluorine
  • Urea