A Small-Molecule Oral Agonist of the Human Glucagon-like Peptide-1 Receptor

David A. Griffith(Pfizer (United States)), David J. Edmonds(Pfizer (United States)), Jean‐Philippe Fortin(Pfizer (United States)), Amit S. Kalgutkar(Pfizer (United States)), J. Brent Kuzmiski(Pfizer (United States)), Paula M. Loria(Pfizer (United States)), Aditi R. Saxena(Pfizer (United States)), Scott W. Bagley(Pfizer (United States)), Clare Buckeridge(Pfizer (United States)), John M. Curto(Pfizer (United States)), David R. Derksen(Pfizer (United States)), João M. Dias(Pfizer (United States)), Matthew C. Griffor(Pfizer (United States)), Seungil Han(Pfizer (United States)), V. Margaret Jackson(Pfizer (United States)), Margaret S. Landis(Pfizer (United States)), Daniel J. Lettiere(Pfizer (United States)), Chris Limberakis(Pfizer (United States)), Yuhang Liu(Pfizer (United States)), Alan M. Mathiowetz(Pfizer (United States)), Jayesh C. Patel(Heptares Therapeutics (United Kingdom)), David W. Piotrowski(Pfizer (United States)), David A. Price(Pfizer (United States)), Roger B. Ruggeri(Pfizer (United States)), David A. Tess(Pfizer (United States))
Journal of Medicinal Chemistry
June 1, 2022
Cited by 153Open Access
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Abstract

Peptide agonists of the glucagon-like peptide-1 receptor (GLP-1R) have revolutionized diabetes therapy, but their use has been limited because they require injection. Herein, we describe the discovery of the orally bioavailable, small-molecule, GLP-1R agonist PF-06882961 (danuglipron). A sensitized high-throughput screen was used to identify 5-fluoropyrimidine-based GLP-1R agonists that were optimized to promote endogenous GLP-1R signaling with nanomolar potency. Incorporation of a carboxylic acid moiety provided considerable GLP-1R potency gains with improved off-target pharmacology and reduced metabolic clearance, ultimately resulting in the identification of danuglipron. Danuglipron increased insulin levels in primates but not rodents, which was explained by receptor mutagensis studies and a cryogenic electron microscope structure that revealed a binding pocket requiring a primate-specific tryptophan 33 residue. Oral administration of danuglipron to healthy humans produced dose-proportional increases in systemic exposure (NCT03309241). This opens an opportunity for oral small-molecule therapies that target the well-validated GLP-1R for metabolic health.


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