Synthesis of constrained benzocinnolinone analogues of CEP-26401 (irdabisant) as potent, selective histamine H3 receptor inverse agonists

Bioorg Med Chem Lett. 2012 Jun 15;22(12):4198-202. doi: 10.1016/j.bmcl.2012.04.001. Epub 2012 Apr 26.

Abstract

A novel class of benzocinnolinones analogs of irdabisant were designed and synthesized as histamine H3R antagonists/inverse agonists. Modifications to the pyridazinone portion of the core and linker led to the identification of molecules with excellent target potency and selectivity with improved rat pharmacokinetic properties and reduced potential hERG liabilities.

MeSH terms

  • Animals
  • CHO Cells
  • Cell Membrane / drug effects
  • Cell Membrane / metabolism
  • Cricetinae
  • Dose-Response Relationship, Drug
  • Drug Inverse Agonism
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Heterocyclic Compounds, 3-Ring / pharmacology
  • Histamine Agonists / chemical synthesis*
  • Histamine Agonists / pharmacology
  • Histamine H3 Antagonists / chemical synthesis*
  • Histamine H3 Antagonists / pharmacology
  • Molecular Structure
  • Nootropic Agents / chemical synthesis*
  • Nootropic Agents / pharmacology
  • Pyridazines / chemical synthesis*
  • Pyridazines / pharmacology
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / pharmacology
  • Rats
  • Receptors, Histamine H3 / chemistry*
  • Receptors, Histamine H3 / metabolism
  • Structure-Activity Relationship

Substances

  • Heterocyclic Compounds, 3-Ring
  • Histamine Agonists
  • Histamine H3 Antagonists
  • Nootropic Agents
  • Pyridazines
  • Pyrrolidines
  • Receptors, Histamine H3
  • 6-(4-(3-(2-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-pyridazin-3-one