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Challenges in the development of an M 4 PAM in vivo tool compound: The discovery of VU0467154 and unexpected DMPK profiles of close analogs
Journal article   Open access   Peer reviewed

Challenges in the development of an M 4 PAM in vivo tool compound: The discovery of VU0467154 and unexpected DMPK profiles of close analogs

Michael R Wood, Meredith J Noetzel, Michael S Poslusney, Bruce J Melancon, James C Tarr, Atin Lamsal, Sichen Chang, Vincent B Luscombe, Rebecca L Weiner, Hyekyung P Cho, …
Bioorganic & medicinal chemistry letters, Vol.27(2), pp.171-175
01/15/2017
DOI: 10.1016/j.bmcl.2016.11.086
PMCID: PMC5340297
PMID: 27939174
url
https://doi.org/10.7270/q2wm1gc0View
Open Access

Abstract

This letter describes the chemical optimization of a novel series of M positive allosteric modulators (PAMs) based on a 5-amino-thieno[2,3-c]pyridazine core, developed via iterative parallel synthesis, and culminating in the highly utilized rodent in vivo tool compound, VU0467154 (5). This is the first report of the optimization campaign (SAR and DMPK profiling) that led to the discovery of VU0467154, and details all of the challenges faced in allosteric modulator programs (steep SAR, species differences in PAM pharmacology and subtle structural changes affecting CNS penetration).
Animals Humans Ligands Nucleoside Transport Proteins - metabolism Pyridazines - administration & dosage Pyridazines - chemical synthesis Pyridazines - pharmacokinetics Pyridazines - pharmacology Rats, Sprague-Dawley Receptor, Muscarinic M4 - agonists Structure-Activity Relationship Thiophenes - administration & dosage Thiophenes - chemical synthesis Thiophenes - pharmacokinetics Thiophenes - pharmacology

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