Discovery of piperidine ethers as selective orexin receptor antagonists (SORAs) inspired by filorexant.

Abstract:

:Highly selective orexin receptor antagonists (SORAs) of the orexin 2 receptor (OX2R) have become attractive targets both as potential therapeutics for insomnia as well as biological tools to help further elucidate the underlying pharmacology of the orexin signaling pathway. Herein, we describe the discovery of a novel piperidine ether 2-SORA class identified by systematic lead optimization beginning with filorexant, a dual orexin receptor antagonist (DORA) that recently completed Phase 2 clinical trials. Changes to the ether linkage and pendant heterocycle of filorexant were found to impart significant selectivity for OX2R, culminating in lead compound PE-6. PE-6 displays sub-nanomolar binding affinity and functional potency on OX2R while maintaining >1600-fold binding selectivity and >200-fold functional selectivity versus the orexin 1 receptor (OX1R). PE-6 bears a clean off-target profile, a good overall preclinical pharmacokinetic (PK) profile, and reduces wakefulness with increased NREM and REM sleep when evaluated in vivo in a rat sleep study. Importantly, subtle structural changes to the piperidine ether class impart dramatic changes in receptor selectivity. To this end, our laboratories have identified multiple piperidine ether 2-SORAs, 1-SORAs, and DORAs, providing access to a number of important biological tool compounds from a single structural class.

journal_name

Bioorg Med Chem Lett

authors

Raheem IT,Breslin MJ,Bruno J,Cabalu TD,Cooke A,Cox CD,Cui D,Garson S,Gotter AL,Fox SV,Harrell CM,Kuduk SD,Lemaire W,Prueksaritanont T,Renger JJ,Stump C,Tannenbaum PL,Williams PD,Winrow CJ,Coleman PJ

doi

10.1016/j.bmcl.2014.12.056

subject

Has Abstract

pub_date

2015-02-01 00:00:00

pages

444-50

issue

3

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(14)01364-X

journal_volume

25

pub_type

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