Discovery of (3-(4-(2-Oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone (AZD1979), a Melanin Concentrating Hormone Receptor 1 (MCHr1) Antagonist with Favorable Physicochemical Properties

J Med Chem. 2016 Mar 24;59(6):2497-511. doi: 10.1021/acs.jmedchem.5b01654. Epub 2016 Feb 5.

Abstract

A novel series of melanin concentrating hormone receptor 1 (MCHr1) antagonists were the starting point for a drug discovery program that culminated in the discovery of 103 (AZD1979). The lead optimization program was conducted with a focus on reducing lipophilicity and understanding the physicochemical properties governing CNS exposure and undesired off-target pharmacology such as hERG interactions. An integrated approach was taken where the key assay was ex vivo receptor occupancy in mice. The candidate compound 103 displayed appropriate lipophilicity for a CNS indication and showed excellent permeability with no efflux. Preclinical GLP toxicology and safety pharmacology studies were without major findings and 103 was taken into clinical trials.

MeSH terms

  • Animals
  • Anti-Obesity Agents / pharmacology
  • Azetidines / chemical synthesis*
  • Azetidines / pharmacology*
  • Body Weight / drug effects
  • Brain / drug effects
  • Brain / metabolism
  • Drug Discovery
  • Ether-A-Go-Go Potassium Channels / antagonists & inhibitors
  • Female
  • Lipids / chemistry
  • Mice
  • Mice, Inbred C57BL
  • Models, Molecular
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / pharmacology*
  • Potassium Channel Blockers / chemical synthesis
  • Potassium Channel Blockers / pharmacology
  • Receptors, Somatostatin / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • AZD1979
  • Anti-Obesity Agents
  • Azetidines
  • Ether-A-Go-Go Potassium Channels
  • Lipids
  • Mchr1 protein, mouse
  • Oxadiazoles
  • Potassium Channel Blockers
  • Receptors, Somatostatin