Development of Highly Potent, G-Protein Pathway Biased, Selective, and Orally Bioavailable GPR84 Agonists

J Med Chem. 2024 Jan 11;67(1):110-137. doi: 10.1021/acs.jmedchem.3c00951. Epub 2023 Dec 26.

Abstract

Orphan G-protein-coupled receptor 84 (GPR84) is a receptor that has been linked to cancer, inflammatory, and fibrotic diseases. We have reported DL-175 as a biased agonist at GPR84 which showed differential signaling via Gαi/cAMP and β-arrestin, but which is rapidly metabolized. Herein, we describe an optimization of DL-175 through a systematic structure-activity relationship (SAR) analysis. This reveals that the replacement of the naphthalene group improved metabolic stability and the addition of a 5-hydroxy substituent to the pyridine N-oxide group, yielding compounds 68 (OX04528) and 69 (OX04529), enhanced the potency for cAMP signaling by 3 orders of magnitude to low picomolar values. Neither compound showed detectable effects on β-arrestin recruitment up to 80 μM. Thus, the new GPR84 agonists 68 and 69 displayed excellent potency, high G-protein signaling bias, and an appropriate in vivo pharmacokinetic profile that will allow investigation of GPR84 biased agonist activity in vivo.

MeSH terms

  • GTP-Binding Proteins* / metabolism
  • Receptors, G-Protein-Coupled* / metabolism
  • Signal Transduction
  • Structure-Activity Relationship
  • beta-Arrestins / metabolism

Substances

  • Receptors, G-Protein-Coupled
  • GTP-Binding Proteins
  • beta-Arrestins