N-[5-(5-fluoropyridin-3-yl)-1H-pyrazol-3-yl]-4-piperidin-1-ylbutyramide (SEN78702, WYE-308775): a medicinal chemistry effort toward an α7 nicotinic acetylcholine receptor agonist preclinical candidate

J Med Chem. 2012 Nov 26;55(22):10277-81. doi: 10.1021/jm3013568. Epub 2012 Nov 2.

Abstract

α7 Nicotinic acetylcholine receptors (α7 nAChR) represent promising therapeutic candidates for the treatment of cognitive impairment associated with Alzheimer's disease (AD) and schizophrenia. A medicinal chemistry effort around previously reported compound 1 (SEN15924, WAY-361789) led to the identification of 12 (SEN78702, WYE-308775) a potent and selective full agonist of the α7 nAChR that demonstrated improved plasma stability, brain levels, and efficacy in behavioral cognition models.

MeSH terms

  • Animals
  • Brain / drug effects*
  • CHO Cells
  • Calcium / metabolism
  • Chemistry, Pharmaceutical
  • Cognition / drug effects*
  • Cricetinae
  • ERG1 Potassium Channel
  • Ether-A-Go-Go Potassium Channels / antagonists & inhibitors*
  • Humans
  • Models, Molecular
  • Nicotinic Agonists / chemical synthesis
  • Nicotinic Agonists / pharmacology*
  • Piperidines / chemical synthesis
  • Piperidines / pharmacology*
  • Pyrazoles / chemical synthesis
  • Pyrazoles / pharmacology*
  • Rats
  • Receptors, Nicotinic / chemistry*
  • Receptors, Nicotinic / metabolism
  • Structure-Activity Relationship
  • alpha7 Nicotinic Acetylcholine Receptor

Substances

  • Chrna7 protein, human
  • Chrna7 protein, rat
  • ERG1 Potassium Channel
  • Ether-A-Go-Go Potassium Channels
  • N-(5-(5-fluoropyridin-3-yl)-1H-pyrazol-3-yl)-4-piperidin-1-ylbutyramide
  • Nicotinic Agonists
  • Piperidines
  • Pyrazoles
  • Receptors, Nicotinic
  • alpha7 Nicotinic Acetylcholine Receptor
  • Calcium