2,6-Disubstituted N-arylsulfonyl piperidines as gamma-secretase inhibitors

Bioorg Med Chem Lett. 2007 Jan 1;17(1):57-62. doi: 10.1016/j.bmcl.2006.09.094. Epub 2006 Oct 4.

Abstract

A novel piperidine series of gamma-secretase inhibitors, potentially useful for the treatment of Alzheimer's disease, is disclosed. SAR investigation revealed the requirement for cis-stereochemistry of the substituents attached to the core, which resulted in the chair-like diaxial conformation of the piperidine ring. The series was optimized to provide inhibitors with IC(50)'s in the single-digit nanomolar range. Absolute stereochemistry of the active enantiomer was assigned.

MeSH terms

  • Alzheimer Disease / drug therapy*
  • Amyloid Precursor Protein Secretases / antagonists & inhibitors*
  • Inhibitory Concentration 50
  • Piperidines / chemical synthesis
  • Piperidines / chemistry*
  • Protease Inhibitors / chemical synthesis
  • Protease Inhibitors / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Piperidines
  • Protease Inhibitors
  • Amyloid Precursor Protein Secretases