Discovery of 5-chloro-N2-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (AZD1480) as a novel inhibitor of the Jak/Stat pathway

J Med Chem. 2011 Jan 13;54(1):262-76. doi: 10.1021/jm1011319. Epub 2010 Dec 7.

Abstract

The myeloproliferative neoplasms, polycythemia vera, essential thrombocythemia, and idiopathic myelofibrosis are a heterogeneous but related group of hematological malignancies characterized by clonal expansion of one or more myeloid lineages. The discovery of the Jak2 V617F gain of function mutation highlighted Jak2 as a potential therapeutic target in the MPNs. Herein, we disclose the discovery of a series of pyrazol-3-yl pyrimidin-4-amines and the identification of 9e (AZD1480) as a potent Jak2 inhibitor. 9e inhibits signaling and proliferation of Jak2 V617F cell lines in vitro, demonstrates in vivo efficacy in a TEL-Jak2 model, has excellent physical properties and preclinical pharmacokinetics, and is currently being evaluated in Phase I clinical trials.

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Dogs
  • Female
  • Humans
  • In Vitro Techniques
  • Janus Kinase 2 / antagonists & inhibitors*
  • Janus Kinase 2 / chemistry
  • Mice
  • Mice, Nude
  • Microsomes, Liver / metabolism
  • Models, Molecular
  • Phosphorylation
  • Protein Conformation
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / pharmacokinetics
  • Pyrazoles / pharmacology
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / pharmacokinetics
  • Pyrimidines / pharmacology
  • Rats
  • STAT Transcription Factors / metabolism
  • STAT Transcription Factors / physiology*
  • STAT3 Transcription Factor / metabolism
  • STAT5 Transcription Factor / metabolism
  • Signal Transduction
  • Stereoisomerism
  • Structure-Activity Relationship
  • Xenograft Model Antitumor Assays

Substances

  • AZD 1480
  • Pyrazoles
  • Pyrimidines
  • STAT Transcription Factors
  • STAT3 Transcription Factor
  • STAT5 Transcription Factor
  • Janus Kinase 2