Potent and selective adenosine A2A receptor antagonists: 1,2,4-Triazolo[1,5-c]pyrimidines

Bioorg Med Chem Lett. 2009 Feb 1;19(3):967-71. doi: 10.1016/j.bmcl.2008.11.075. Epub 2008 Nov 24.

Abstract

Antagonism of the adenosine A(2a) receptor offers great promise in the treatment of Parkinson's disease. In the course of exploring pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine A(2A) antagonists, which led to clinical candidate SCH 420814, we prepared 1,2,4-triazolo[1,5-c]pyrimidines with potent and selective (vs A(1)) A(2a) antagonist activity, including oral activity in the rat haloperidol-induced catalepsy model. Structure-activity relationships and plasma levels are described for this series.

MeSH terms

  • Adenosine A2 Receptor Antagonists*
  • Administration, Oral
  • Animals
  • Area Under Curve
  • Catalepsy
  • Chemistry, Pharmaceutical / methods
  • Drug Design
  • Haloperidol / pharmacology
  • Models, Chemical
  • Parkinson Disease / drug therapy*
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology*
  • Rats
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis*
  • Triazoles / pharmacology

Substances

  • Adenosine A2 Receptor Antagonists
  • Pyrimidines
  • Triazoles
  • 2-(2-furanyl)-7-(2-(4-(4-(2-methoxyethoxy)phenyl)-1-piperazinyl)ethyl)-7H-pyrazolo(4,3-e)(1,2,4)triazolo(1,5-c)pyrimidine-5-amine
  • Haloperidol