Optimization of imidazo[4,5-b]pyridine-based kinase inhibitors: identification of a dual FLT3/Aurora kinase inhibitor as an orally bioavailable preclinical development candidate for the treatment of acute myeloid leukemia

J Med Chem. 2012 Oct 25;55(20):8721-34. doi: 10.1021/jm300952s. Epub 2012 Oct 8.

Abstract

Optimization of the imidazo[4,5-b]pyridine-based series of Aurora kinase inhibitors led to the identification of 6-chloro-7-(4-(4-chlorobenzyl)piperazin-1-yl)-2-(1,3-dimethyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridine (27e), a potent inhibitor of Aurora kinases (Aurora-A K(d) = 7.5 nM, Aurora-B K(d) = 48 nM), FLT3 kinase (K(d) = 6.2 nM), and FLT3 mutants including FLT3-ITD (K(d) = 38 nM) and FLT3(D835Y) (K(d) = 14 nM). FLT3-ITD causes constitutive FLT3 kinase activation and is detected in 20-35% of adults and 15% of children with acute myeloid leukemia (AML), conferring a poor prognosis in both age groups. In an in vivo setting, 27e strongly inhibited the growth of a FLT3-ITD-positive AML human tumor xenograft (MV4-11) following oral administration, with in vivo biomarker modulation and plasma free drug exposures consistent with dual FLT3 and Aurora kinase inhibition. Compound 27e, an orally bioavailable dual FLT3 and Aurora kinase inhibitor, was selected as a preclinical development candidate for the treatment of human malignancies, in particular AML, in adults and children.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Oral
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Aurora Kinase A
  • Aurora Kinase B
  • Aurora Kinases
  • Biological Availability
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • ERG1 Potassium Channel
  • Ether-A-Go-Go Potassium Channels / antagonists & inhibitors
  • Female
  • Humans
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Imidazoles / pharmacology
  • Leukemia, Myeloid, Acute / drug therapy*
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Microsomes, Liver / metabolism
  • Models, Molecular
  • Mutation
  • Neoplasm Transplantation
  • Protein Serine-Threonine Kinases / antagonists & inhibitors*
  • Purines / chemical synthesis*
  • Purines / chemistry
  • Purines / pharmacology
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / pharmacology
  • Rats
  • Rats, Sprague-Dawley
  • Transplantation, Heterologous
  • fms-Like Tyrosine Kinase 3 / antagonists & inhibitors*
  • fms-Like Tyrosine Kinase 3 / genetics

Substances

  • 6-chloro-7-(4-(4-chlorobenzyl)piperazin-1-yl)-2-(1,3-dimethyl-1H-pyrazol-4-yl)-3H-imidazo(4,5-b)pyridine
  • Antineoplastic Agents
  • ERG1 Potassium Channel
  • Ether-A-Go-Go Potassium Channels
  • Imidazoles
  • Purines
  • Pyrazoles
  • Pyridines
  • FLT3 protein, human
  • fms-Like Tyrosine Kinase 3
  • AURKB protein, human
  • Aurka protein, mouse
  • Aurka protein, rat
  • Aurkb protein, mouse
  • Aurkb protein, rat
  • Aurora Kinase A
  • Aurora Kinase B
  • Aurora Kinases
  • Protein Serine-Threonine Kinases