The discovery and synthesis of potent zwitterionic inhibitors of renin

Bioorg Med Chem Lett. 2011 Apr 15;21(8):2430-6. doi: 10.1016/j.bmcl.2011.02.067. Epub 2011 Feb 18.

Abstract

The incorporation of a carboxylic acid within in a series of 3-amido-4-aryl substituted piperidines (represented by general structure 32) led to the discovery of potent, zwitterionic, renin inhibitors with improved off-target profiles (CYP3A4 time-dependent inhibition and hERG affinity) relative to analogous non-zwitterionic inhibitors of the past (i.e., 3). Strategies to address the oral absorption of these zwitterions are also discussed within.

MeSH terms

  • Administration, Oral
  • Animals
  • Catalytic Domain
  • Computer Simulation
  • Dogs
  • Drug Evaluation, Preclinical
  • Humans
  • Piperidines / chemical synthesis
  • Piperidines / chemistry
  • Piperidines / pharmacokinetics
  • Protease Inhibitors / chemical synthesis*
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / pharmacokinetics
  • Rats
  • Rats, Sprague-Dawley
  • Renin / antagonists & inhibitors*
  • Renin / metabolism
  • Structure-Activity Relationship

Substances

  • Piperidines
  • Protease Inhibitors
  • Renin