Discovery of Highly Isoform Selective Orally Bioavailable Phosphoinositide 3-Kinase (PI3K)-γ Inhibitors

J Med Chem. 2018 Jun 28;61(12):5435-5441. doi: 10.1021/acs.jmedchem.8b00447. Epub 2018 Jun 18.

Abstract

In this paper, we describe the discovery and optimization of a new chemotype of isoform selective PI3Kγ inhibitors. Starting from an HTS hit, potency and physicochemical properties could be improved to give compounds such as 15, which is a potent and remarkably selective PI3Kγ inhibitor with ADME properties suitable for oral administration. Compound 15 was advanced into in vivo studies showing dose-dependent inhibition of LPS-induced airway neutrophilia in rats when administered orally.

MeSH terms

  • Adenosine Triphosphate / metabolism
  • Administration, Oral
  • Animals
  • Binding Sites
  • Biological Availability
  • Crystallography, X-Ray
  • Dogs
  • Dose-Response Relationship, Drug
  • Drug Evaluation, Preclinical / methods
  • Enzyme Inhibitors / administration & dosage
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacokinetics
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Isoenzymes
  • Leukocyte Disorders / chemically induced
  • Leukocyte Disorders / drug therapy
  • Lipopolysaccharides / toxicity
  • Phosphatidylinositol 3-Kinases / chemistry
  • Phosphatidylinositol 3-Kinases / metabolism
  • Phosphoinositide-3 Kinase Inhibitors*
  • Phthalimides / chemistry
  • Rats
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Isoenzymes
  • Lipopolysaccharides
  • Phosphoinositide-3 Kinase Inhibitors
  • Phthalimides
  • phthalimidine
  • Adenosine Triphosphate