Invention of novel 3-aminopiperidin-2-ones as calcitonin gene-related peptide receptor antagonists

Bioorg Med Chem Lett. 2024 Nov 1:112:129944. doi: 10.1016/j.bmcl.2024.129944. Epub 2024 Sep 2.

Abstract

A novel series of 3-amino-piperidin-2-one-based calcitonin gene-related peptide (CGRP) receptor antagonists was invented based upon the discovery of unexpected structure-activity observations. Initial exploration of the structure-activity relationships enabled the generation of a moderately potent lead structure (4). A series of modifications, including ring contraction and inversion of stereocenters, led to surprising improvements in CGRP receptor affinity. These studies identified compound 23, a structurally novel potent, orally bioavailable CGRP receptor antagonist.

Keywords: CGRP receptor antagonist; Calcitonin gene-related peptide; Migraine.

MeSH terms

  • Animals
  • Calcitonin Gene-Related Peptide Receptor Antagonists* / chemical synthesis
  • Calcitonin Gene-Related Peptide Receptor Antagonists* / chemistry
  • Calcitonin Gene-Related Peptide Receptor Antagonists* / pharmacology
  • Humans
  • Molecular Structure
  • Piperidines* / chemical synthesis
  • Piperidines* / chemistry
  • Piperidines* / pharmacology
  • Rats
  • Receptors, Calcitonin Gene-Related Peptide / metabolism
  • Structure-Activity Relationship

Substances

  • Calcitonin Gene-Related Peptide Receptor Antagonists
  • Piperidines
  • Receptors, Calcitonin Gene-Related Peptide