Bradykinin B1 receptor antagonists: an alpha-hydroxy amide with an improved metabolism profile

Bioorg Med Chem Lett. 2008 Sep 15;18(18):5107-10. doi: 10.1016/j.bmcl.2008.07.126. Epub 2008 Aug 5.

Abstract

A series of carbo- and heterocyclic alpha-hydroxy amide-derived bradykinin B1 antagonists was prepared and evaluated. A 4,4-difluorocyclohexyl alpha-hydroxy amide was incorporated along with a 2-methyl tetrazole in lieu of an oxadiazole to afford a suitable compound with good pharmacokinetic properties, CNS penetration, and clearance by multiple metabolic pathways.

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amides / pharmacokinetics
  • Amides / pharmacology*
  • Animals
  • Bradykinin B1 Receptor Antagonists*
  • Central Nervous System / drug effects
  • Combinatorial Chemistry Techniques
  • Drug Design
  • Humans
  • Molecular Structure
  • Rats
  • Structure-Activity Relationship
  • Tetrazoles / chemical synthesis*
  • Tetrazoles / chemistry
  • Tetrazoles / pharmacokinetics
  • Tetrazoles / pharmacology*

Substances

  • Amides
  • Bradykinin B1 Receptor Antagonists
  • Tetrazoles