Oximino-piperidino-piperidine-based CCR5 antagonists. Part 2: synthesis, SAR and biological evaluation of symmetrical heteroaryl carboxamides

Bioorg Med Chem Lett. 2003 Feb 24;13(4):709-12. doi: 10.1016/s0960-894x(02)01063-6.

Abstract

The synthesis, SAR and biological evaluation of symmetrical amide analogues of our clinical candidate SCH 351125 are described. A series of potent and orally bioavailable CCR5 antagonists containing symmetrical 2,6-dimethyl isonicotinamides and 2, 6-dimethyl pyrimidines amides were generated with enhanced affinity for the CCR5 receptor.

MeSH terms

  • Amides / chemical synthesis*
  • Amides / pharmacokinetics
  • Amides / pharmacology
  • Animals
  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / pharmacokinetics
  • Anti-HIV Agents / pharmacology
  • CCR5 Receptor Antagonists*
  • Chemokine CCL5 / antagonists & inhibitors
  • Cyclic N-Oxides
  • Drug Evaluation, Preclinical
  • HIV-1 / drug effects
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Heterocyclic Compounds, 3-Ring / pharmacokinetics
  • Heterocyclic Compounds, 3-Ring / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Oximes
  • Piperidines / chemical synthesis*
  • Piperidines / pharmacokinetics
  • Piperidines / pharmacology
  • Pyridines
  • Rats
  • Structure-Activity Relationship

Substances

  • Amides
  • Anti-HIV Agents
  • CCR5 Receptor Antagonists
  • Chemokine CCL5
  • Cyclic N-Oxides
  • Heterocyclic Compounds, 3-Ring
  • Oximes
  • Piperidines
  • Pyridines
  • Ancriviroc