Discovery of biphenyl piperazines as novel and long acting muscarinic acetylcholine receptor antagonists

J Med Chem. 2008 Oct 9;51(19):5915-8. doi: 10.1021/jm800935u. Epub 2008 Sep 18.

Abstract

A series of novel biphenyl piperazines was discovered as highly potent muscarinic acetylcholine receptor antagonists via high throughput screening and subsequent optimization. Compound 5c with respective 500- and 20-fold subtype selectivity for M3 over M2 and M1 exhibited excellent inhibitory activity and long duration of action in a bronchoconstriction in vivo model in mice via intranasal administration. The novel inhaled mAChR antagonists are potentially useful therapeutic agents for the treatment of chronic obstructive pulmonary disease.

MeSH terms

  • Administration, Intranasal
  • Animals
  • Bronchial Provocation Tests
  • Bronchoconstriction / drug effects*
  • Bronchoconstrictor Agents / pharmacology
  • Bronchodilator Agents / chemical synthesis
  • Bronchodilator Agents / chemistry
  • Bronchodilator Agents / pharmacology*
  • Disease Models, Animal
  • Drug Evaluation, Preclinical
  • Methacholine Chloride / pharmacology
  • Mice
  • Molecular Structure
  • Piperazines / chemical synthesis
  • Piperazines / chemistry
  • Piperazines / pharmacology*
  • Receptors, Muscarinic / drug effects*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Bronchoconstrictor Agents
  • Bronchodilator Agents
  • Piperazines
  • Receptors, Muscarinic
  • Methacholine Chloride