Antagonists of the human A(2A) adenosine receptor. 4. Design, synthesis, and preclinical evaluation of 7-aryltriazolo[4,5-d]pyrimidines

J Med Chem. 2009 Jan 8;52(1):33-47. doi: 10.1021/jm800961g.

Abstract

Antagonism of the human A(2A) receptor has been implicated as a point of therapeutic intervention in the alleviation of the symptoms associated with Parkinson's disease. This is thought to occur, at least in part, by increasing the sensitivity of the dopaminergic neurons to the residual, depleted levels of striatal dopamine. We herein describe a novel series of functionalized triazolo[4,5-d]pyrimidine derivatives that display functional antagonism of the A(2A) receptor. Optimization of these compounds has resulted in improvements in potency, selectivity, and the pharmacokinetic properties of key derivatives. These efforts have led to the discovery of 60 (V2006/BIIB014), which demonstrates strong oral activity in commonly used models of Parkinson's disease. Furthermore, this derivative has shown excellent preclinical pharmacokinetics and has successfully completed phase I clinical studies. This compound is presently undergoing further clinical evaluation in collaboration with Biogen Idec.

MeSH terms

  • Adenosine A2 Receptor Antagonists*
  • Amines / chemistry
  • Animals
  • Azoles / chemical synthesis*
  • Azoles / chemistry
  • Azoles / pharmacology*
  • Azoles / therapeutic use
  • Drug Design*
  • Drug Evaluation, Preclinical
  • Gait Disorders, Neurologic / chemically induced
  • Gait Disorders, Neurologic / drug therapy
  • Haloperidol / pharmacology
  • Humans
  • Mice
  • Molecular Structure
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology*
  • Pyrimidines / therapeutic use
  • Rats
  • Receptor, Adenosine A2A / classification
  • Receptor, Adenosine A2A / metabolism
  • Structure-Activity Relationship

Substances

  • Adenosine A2 Receptor Antagonists
  • Amines
  • Azoles
  • Pyrimidines
  • Receptor, Adenosine A2A
  • Haloperidol
  • pyrimidine