Pyrido[2,3-d]pyrimidine angiotensin II antagonists

J Med Chem. 1994 Feb 18;37(4):542-50. doi: 10.1021/jm00030a013.

Abstract

A series of pyrido[2,3-d]pyrimidine angiotensin II (A II) antagonists was synthesized and tested for antagonism of A II. Compounds with a biphenylyltetrazole pharmacophore and small alkyl groups at the 2- and 4-positions of the pyridopyrimidine ring were found to be the most potent in an AT1 receptor binding assay and in blocking the A II pressor response in anesthetized, ganglion-blocked A II-infused rats. 5,8-Dihydro-2,4-dimethyl-8-[(2'-(1H-tetrazol-5-yl) [1,1'-biphenyl]-4-yl)methyl]pyrido[2,3-d]pyrimidin-7(6H)-one (4a) was one of the more potent compounds in the binding assay and was the most efficacious compound in the A II-infused rat model. Further study of 4a in Goldblatt (2K-1C) rats showed the compound to have oral bioavailability and to be an efficacious and potent compound in a high renin form of hypertension.

MeSH terms

  • Animals
  • Blood Pressure / drug effects
  • Liver / drug effects
  • Liver / metabolism
  • Male
  • Pressoreceptors / drug effects
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacokinetics
  • Pyridines / pharmacology*
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / pharmacokinetics
  • Pyrimidines / pharmacology*
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship
  • Tetrazoles / chemical synthesis*
  • Tetrazoles / pharmacokinetics
  • Tetrazoles / pharmacology*

Substances

  • Pyridines
  • Pyrimidines
  • Tetrazoles
  • tasosartan