Development of a highly potent, novel M5 positive allosteric modulator (PAM) demonstrating CNS exposure: 1-((1H-indazol-5-yl)sulfoneyl)-N-ethyl-N-(2-(trifluoromethyl)benzyl)piperidine-4-carboxamide (ML380)

Patrick R Gentry, Masaya Kokubo, Thomas M Bridges, Meredith J Noetzel, Hyekyung P Cho, Atin Lamsal, Emery Smith, Peter Chase, Peter S Hodder, Colleen M Niswender, J Scott Daniels, P Jeffrey Conn, Craig W Lindsley, Michael R Wood

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Abstract

A functional high throughput screen identified a novel chemotype for the positive allosteric modulation (PAM) of the muscarinic acetylcholine receptor (mAChR) subtype 5 (M5). Application of rapid analog, iterative parallel synthesis efficiently optimized M5 potency to arrive at the most potent M5 PAMs prepared to date and provided tool compound 8n (ML380) demonstrating modest CNS penetration (human M5 EC50 = 190 nM, rat M5 EC50 = 610 nM, brain to plasma ratio (Kp) of 0.36).

OriginalsprogEngelsk
TidsskriftJournal of Medicinal Chemistry
Vol/bind57
Udgave nummer18
Sider (fra-til)7804-10
Antal sider7
ISSN0022-2623
DOI
StatusUdgivet - 25 sep. 2014
Udgivet eksterntJa

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