Discovery and Characterization of AZD6738, a Potent Inhibitor of Ataxia Telangiectasia Mutated and Rad3 Related (ATR) Kinase with Application as an Anticancer Agent

J Med Chem. 2018 Nov 21;61(22):9889-9907. doi: 10.1021/acs.jmedchem.8b01187. Epub 2018 Nov 10.

Abstract

The kinase ataxia telangiectasia mutated and rad3 related (ATR) is a key regulator of the DNA-damage response and the apical kinase which orchestrates the cellular processes that repair stalled replication forks (replication stress) and associated DNA double-strand breaks. Inhibition of repair pathways mediated by ATR in a context where alternative pathways are less active is expected to aid clinical response by increasing replication stress. Here we describe the development of the clinical candidate 2 (AZD6738), a potent and selective sulfoximine morpholinopyrimidine ATR inhibitor with excellent preclinical physicochemical and pharmacokinetic (PK) characteristics. Compound 2 was developed improving aqueous solubility and eliminating CYP3A4 time-dependent inhibition starting from the earlier described inhibitor 1 (AZ20). The clinical candidate 2 has favorable human PK suitable for once or twice daily dosing and achieves biologically effective exposure at moderate doses. Compound 2 is currently being tested in multiple phase I/II trials as an anticancer agent.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology*
  • Ataxia Telangiectasia Mutated Proteins / antagonists & inhibitors*
  • Cell Line, Tumor
  • Chemical Phenomena
  • Clinical Trials as Topic
  • Drug Discovery*
  • Female
  • Humans
  • Indoles
  • Mice
  • Models, Molecular
  • Molecular Conformation
  • Morpholines
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacokinetics
  • Protein Kinase Inhibitors / pharmacology*
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacokinetics
  • Pyrimidines / pharmacology*
  • Sulfonamides
  • Sulfoxides / chemistry
  • Sulfoxides / pharmacokinetics
  • Sulfoxides / pharmacology*
  • Tissue Distribution

Substances

  • Antineoplastic Agents
  • Indoles
  • Morpholines
  • Protein Kinase Inhibitors
  • Pyrimidines
  • Sulfonamides
  • Sulfoxides
  • ceralasertib
  • ATR protein, human
  • Ataxia Telangiectasia Mutated Proteins