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(CAS: 1788055-12-8 )

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Background Information of VU0486846

VU0486846 is a novel muscarinic acetylcholine receptor 1 (M1) positive allosteric modulator (PAM). M1 PAMs hold great promise for the treatment of cognitive impairment, schizophrenia, and Alzheimer’s disease.

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Mechanism and Indications

Signaling Pathways Neuronal Signaling GPCR/G Protein
Target mAChR
Research Area Neurological Disease

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase

Chemical Information

M.Wt Formula CAS No. Synonyms
432.51 C25H28N4O3 1788055-12-8

Structure Information of VU0486846

Smiles C1C=C2O[[email protected]@H](C(N([[email protected]]3CCCC[[email protected]@H]3O)[H])=O)CN(CC3C=CC(N4N=CC=C4)=CC=3)C2=CC=1 |&1:4,7,12,r|
InChI InChI=1/C25H28N4O3/c30-22-8-3-1-6-20(22)27-25(31)24-17-28(21-7-2-4-9-23(21)32-24)16-18-10-12-19(13-11-18)29-15-5-14-26-29/h2,4-5,7,9-15,20,22,24,30H,1,3,6,8,16-17H2,(H,27,31)/t20-,22-,24+/s3

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[1].Engers JL, et al. VU6007477, a Novel M1 PAM Based on a Pyrrolo[2,3-b]pyridine Carboxamide Core Devoid of Cholinergic Adverse Events. ACS Med Chem Lett. 2018 Sep 4;9(9):917-922.
Herein, we report the chemical optimization of a new series of M1 positive allosteric modulators (PAMs) based on a novel pyrrolo[2,3-b]pyridine core, developed via scaffold hopping and iterative parallel synthesis. The vast majority of analogs in this series proved to display robust cholinergic seizure activity. However, by removal of the secondary hydroxyl group, VU6007477 resulted with good rat M1 PAM potency (EC50 = 230 nM, 93% ACh max), minimal M1 agonist activity (agonist EC50 > 10 μM), good CNS penetration (rat brain/plasma K p = 0.28, K p,uu = 0.32; mouse K p = 0.16, K p,uu = 0.18), and no cholinergic adverse events (AEs, e.g., seizures). This work demonstrates that within a chemical series prone to robust M1 ago-PAM activity, SAR can result, which affords pure M1 PAMs, devoid of cholinergic toxicity/seizure liability.

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