Discovery of novel non-peptide CCR1 receptor antagonists

J Med Chem. 1999 Nov 4;42(22):4680-94. doi: 10.1021/jm990316l.

Abstract

Ligands for the CCR1 receptor (MIP-1alpha and RANTES) have been implicated in a number of chronic inflammatory diseases, most notably multiple sclerosis and rheumatoid arthritis. Because these ligands share a common receptor, CCR1, we sought to discover antagonists for this receptor as an approach to treating these disorders. A novel series of 4-hydroxypiperidines has been discovered by high throughput screening (HTS) which potently inhibits the binding of MIP-1alpha and RANTES to the recombinant human CCR1 chemokine receptor. The structure-activity relationships of various segments of this template are described as the initial HTS lead 1 was optimized synthetically to the highly potent receptor antagonist 6s. This compound has been shown to have at least 200-fold selectivity for inhibition of CCR1 over other human 7-TM receptors, including other chemokine receptors. In addition, data obtained from in vitro functional assays demonstrate the functional antagonism of compound 6s and structurally related analogues against the CCR1 receptor in a concentration dependent manner. The discovery and optimization of potent and selective CCR1 receptor antagonists represented by compound 6s potentially represent a novel approach to the treatment of chronic inflammatory diseases.

MeSH terms

  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / metabolism
  • Calcium / metabolism
  • Cell Line
  • Chemokine CCL3
  • Chemokine CCL4
  • Chemokine CCL5 / metabolism
  • Drug Evaluation, Preclinical
  • Humans
  • Macrophage Inflammatory Proteins / metabolism
  • Macrophage Inflammatory Proteins / pharmacology
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Nitriles / metabolism
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Piperidines / metabolism
  • Receptors, CCR1
  • Receptors, Chemokine / antagonists & inhibitors*
  • Receptors, Chemokine / metabolism
  • Recombinant Proteins / antagonists & inhibitors
  • Recombinant Proteins / metabolism
  • Structure-Activity Relationship

Substances

  • 4-(4-chlorophenyl)-4-hydroxy-alpha,alpha-diphenyl-1-piperidinepentanenitrile
  • Anti-Inflammatory Agents
  • CCR1 protein, human
  • Chemokine CCL3
  • Chemokine CCL4
  • Chemokine CCL5
  • Macrophage Inflammatory Proteins
  • Nitriles
  • Piperidines
  • Receptors, CCR1
  • Receptors, Chemokine
  • Recombinant Proteins
  • Calcium