Substituted fused bicyclic pyrrolizinones as potent, orally bioavailable hNK1 antagonists

Bioorg Med Chem Lett. 2010 Mar 15;20(6):2007-12. doi: 10.1016/j.bmcl.2010.01.065. Epub 2010 Jan 20.

Abstract

Previous work on human NK(1) (hNK(1)) antagonists in which the core of the structure is a 5,5-fused pyrrolizinone has been disclosed. The structural-activity-relationship studies on simple alpha- and beta-substituted compounds of this series provided several potent and bioavailable hNK(1) antagonists that displayed excellent brain penetration as observed by their good efficacy in the gerbil foot-tapping (GFT) model assay. Several of these compounds exhibited 100% inhibition of the foot-tapping response at 0.1 and 24h with ID(50)'s of less than 1 mpk. One particular alpha-substituted compound (2b) had an excellent pharmacokinetic profile across preclinical species with reasonable in vivo functional activity and minimal ancillary activity.

MeSH terms

  • Administration, Oral
  • Animals
  • Biological Availability
  • Bridged Bicyclo Compounds / administration & dosage
  • Bridged Bicyclo Compounds / pharmacokinetics
  • Bridged Bicyclo Compounds / pharmacology*
  • Humans
  • Neurokinin-1 Receptor Antagonists*
  • Pyrroles / administration & dosage
  • Pyrroles / pharmacokinetics
  • Pyrroles / pharmacology*

Substances

  • Bridged Bicyclo Compounds
  • Neurokinin-1 Receptor Antagonists
  • Pyrroles