Discovery of 4-[(Z)-(4-bromophenyl)- (ethoxyimino)methyl]-1'-[(2,4-dimethyl-3- pyridinyl)carbonyl]-4'-methyl-1,4'- bipiperidine N-oxide (SCH 351125): an orally bioavailable human CCR5 antagonist for the treatment of HIV infection

J Med Chem. 2001 Oct 11;44(21):3339-42. doi: 10.1021/jm015526o.

Abstract

Structure-activity studies on piperidino-piperidine 3 led to the discovery of SCH 351125 (1), a selective CCR5 antagonist with potent activity against RANTES binding (K(i) = 2 nM), which possesses subnanomolar activity in blocking viral entry and has excellent antiviral potency versus a panel of primary HIV-1 viral isolates. Compound 1, which has good oral bioavailability in rats, dogs, and monkeys, is proposed as a potential therapeutic agent for the treatment of HIV-1 and has entered human clinical trials.

MeSH terms

  • Administration, Oral
  • Animals
  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacokinetics
  • Anti-HIV Agents / pharmacology
  • Biological Availability
  • CCR5 Receptor Antagonists*
  • Cell Line
  • Cyclic N-Oxides / chemical synthesis*
  • Cyclic N-Oxides / chemistry
  • Cyclic N-Oxides / pharmacokinetics
  • Cyclic N-Oxides / pharmacology
  • Dogs
  • Drug Evaluation, Preclinical
  • HIV-1 / drug effects
  • Humans
  • In Vitro Techniques
  • Leukocytes, Mononuclear / virology
  • Macaca fascicularis
  • Oximes
  • Piperazines / chemical synthesis*
  • Piperazines / chemistry
  • Piperazines / pharmacokinetics
  • Piperazines / pharmacology
  • Piperidines*
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / pharmacokinetics
  • Pyridines / pharmacology
  • Rats
  • Structure-Activity Relationship

Substances

  • Anti-HIV Agents
  • CCR5 Receptor Antagonists
  • Cyclic N-Oxides
  • Oximes
  • Piperazines
  • Piperidines
  • Pyridines
  • Ancriviroc