The design of a novel series of muscarinic receptor antagonists leading to AZD8683, a potential inhaled treatment for COPD

Bioorg Med Chem Lett. 2013 Dec 1;23(23):6248-53. doi: 10.1016/j.bmcl.2013.09.092. Epub 2013 Oct 4.

Abstract

A novel series of muscarinic receptor antagonists was developed, with the aim of identifying a compound with high M3 receptor potency and a reduced risk of dose-limiting side effects with potential for the treatment of COPD. Initial compound modifications led to a novel cycloheptyl series, which was improved by focusing on a quinuclidine sub-series. A wide range of N-substituents was evaluated to determine the optimal substituent providing a high M3 receptor potency, high intrinsic clearance and high human plasma protein binding. Compounds achieving in vitro study criteria were selected for in vivo evaluation. Pharmacokinetic half-lives, inhibition of bronchoconstriction and duration of action, as well as systemic side effects, induced by the compounds were assessed in guinea-pig models. Compounds with a long duration of action and good therapeutic index were identified and AZD8683 was selected for progression to the clinic.

Keywords: Bronchoconstriction; COPD; Muscarinic M(3) antagonist; Salivation.

MeSH terms

  • Administration, Inhalation
  • Animals
  • Bronchoconstriction / drug effects
  • Cycloheptanes / chemistry*
  • Cycloheptanes / pharmacokinetics
  • Cycloheptanes / pharmacology*
  • Disease Models, Animal
  • Guinea Pigs
  • Humans
  • Molecular Structure
  • Muscarinic Antagonists / administration & dosage*
  • Muscarinic Antagonists / chemistry*
  • Muscarinic Antagonists / pharmacokinetics
  • Pulmonary Disease, Chronic Obstructive / drug therapy*
  • Receptors, Muscarinic / chemistry
  • Receptors, Muscarinic / metabolism

Substances

  • Cycloheptanes
  • Muscarinic Antagonists
  • Receptors, Muscarinic