Design, synthesis, and evaluation of conformationally restricted acetanilides as potent and selective β3 adrenergic receptor agonists for the treatment of overactive bladder

J Med Chem. 2014 Feb 27;57(4):1437-53. doi: 10.1021/jm4017224. Epub 2014 Feb 5.

Abstract

A series of conformationally restricted acetanilides were synthesized and evaluated as β3-adrenergic receptor agonists (β3-AR) for the treatment of overactive bladder (OAB). Optimization studies identified a five-membered ring as the preferred conformational lock of the acetanilide. Further optimization of both the aromatic and thiazole regions led to compounds such as 19 and 29, which have a good balance of potency and selectivity. These compounds have significantly reduced intrinsic clearance compared to our initial series of pyridylethanolamine β3-AR agonists and thus have improved unbound drug exposures. Both analogues demonstrated dose dependent β3-AR mediated responses in a rat bladder hyperactivity model.

MeSH terms

  • Acetanilides / chemical synthesis*
  • Acetanilides / pharmacology*
  • Acetanilides / therapeutic use
  • Adrenergic beta-3 Receptor Agonists / chemical synthesis*
  • Adrenergic beta-3 Receptor Agonists / pharmacology*
  • Adrenergic beta-3 Receptor Agonists / therapeutic use
  • Animals
  • CHO Cells
  • Cricetinae
  • Cricetulus
  • Drug Design
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Urinary Bladder, Overactive / drug therapy*

Substances

  • Acetanilides
  • Adrenergic beta-3 Receptor Agonists