2-[(3aR,4R,5S,7aS)-5-{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxyethoxy}-4-(2-methylphenyl)octahydro-2H-isoindol-2-yl]-1,3-oxazol-4(5H)-one: a potent human NK1 receptor antagonist with multiple clearance pathways

J Med Chem. 2013 Jul 25;56(14):5940-8. doi: 10.1021/jm400751p. Epub 2013 Jul 9.

Abstract

Hydroisoindoline 2 has been previously identified as a potent, brain-penetrant NK1 receptor antagonist with a long duration of action and improved profile of CYP3A4 inhibition and induction compared to aprepitant. However, compound 2 is predicted, based on data in preclinical species, to have a human half-life longer than 40 h and likely to have drug-drug-interactions (DDI), as 2 is a victim of CYP3A4 inhibition caused by its exclusive clearance pathway via CYP3A4 oxidation in humans. We now report 2-[(3aR,4R,5S,7aS)-5-{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxyethoxy}-4-(2-methylphenyl)octahydro-2H-isoindol-2-yl]-1,3-oxazol-4(5H)-one (3) as a next generation NK1 antagonist that possesses an additional clearance pathway through glucuronidation in addition to that via CYP3A4 oxidation. Compound 3 has a much lower propensity for drug-drug interactions and a reduced estimated human half-life consistent with once daily dosing. In preclinical species, compound 3 has demonstrated potency, brain penetration, and a safety profile similar to 2, as well as excellent pharmacokinetics.

MeSH terms

  • Cytochrome P-450 CYP3A
  • Cytochrome P-450 CYP3A Inhibitors
  • Drug Interactions
  • Glucuronides / metabolism
  • Humans
  • Isoindoles / chemical synthesis*
  • Isoindoles / chemistry
  • Isoindoles / pharmacokinetics
  • Isoindoles / pharmacology
  • Metabolic Clearance Rate
  • Neurokinin-1 Receptor Antagonists / chemical synthesis*
  • Neurokinin-1 Receptor Antagonists / chemistry
  • Neurokinin-1 Receptor Antagonists / pharmacokinetics
  • Neurokinin-1 Receptor Antagonists / pharmacology
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry
  • Oxazoles / pharmacokinetics
  • Oxazoles / pharmacology
  • Peptide Fragments / pharmacology
  • Substance P / analogs & derivatives
  • Substance P / pharmacology

Substances

  • 2-(5-(1-(3,5-bis(trifluoromethyl)phenyl)-2-hydroxyethoxy)-4-(2-methylphenyl)octahydro-2H-isoindol-2-yl)-1,3-oxazol-4(5H)-one
  • Cytochrome P-450 CYP3A Inhibitors
  • Glucuronides
  • Isoindoles
  • Neurokinin-1 Receptor Antagonists
  • Oxazoles
  • Peptide Fragments
  • GR 73632
  • Substance P
  • Cytochrome P-450 CYP3A
  • CYP3A4 protein, human