Optimization of an Imidazo[1,2- a]pyridine Series to Afford Highly Selective Type I1/2 Dual Mer/Axl Kinase Inhibitors with In Vivo Efficacy

J Med Chem. 2021 Sep 23;64(18):13524-13539. doi: 10.1021/acs.jmedchem.1c00920. Epub 2021 Sep 3.

Abstract

Inhibition of Mer and Axl kinases has been implicated as a potential way to improve the efficacy of current immuno-oncology therapeutics by restoring the innate immune response in the tumor microenvironment. Highly selective dual Mer/Axl kinase inhibitors are required to validate this hypothesis. Starting from hits from a DNA-encoded library screen, we optimized an imidazo[1,2-a]pyridine series using structure-based compound design to improve potency and reduce lipophilicity, resulting in a highly selective in vivo probe compound 32. We demonstrated dose-dependent in vivo efficacy and target engagement in Mer- and Axl-dependent efficacy models using two structurally differentiated and selective dual Mer/Axl inhibitors. Additionally, in vivo efficacy was observed in a preclinical MC38 immuno-oncology model in combination with anti-PD1 antibodies and ionizing radiation.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / therapeutic use*
  • Axl Receptor Tyrosine Kinase
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Screening Assays, Antitumor
  • Female
  • Imidazoles / chemical synthesis
  • Imidazoles / therapeutic use*
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Mice, Nude
  • Molecular Structure
  • Neoplasms / drug therapy*
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / therapeutic use*
  • Proto-Oncogene Proteins / metabolism
  • Pyridines / chemical synthesis
  • Pyridines / therapeutic use*
  • Receptor Protein-Tyrosine Kinases / metabolism
  • Structure-Activity Relationship
  • c-Mer Tyrosine Kinase / metabolism

Substances

  • Antineoplastic Agents
  • Imidazoles
  • Protein Kinase Inhibitors
  • Proto-Oncogene Proteins
  • Pyridines
  • Mertk protein, mouse
  • Receptor Protein-Tyrosine Kinases
  • c-Mer Tyrosine Kinase
  • Axl Receptor Tyrosine Kinase
  • AXL receptor tyrosine kinase, mouse