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US 12,577,234 B2Granted
Antagonists of the muscarinic acetylcholine receptor M4
AssigneeVanderbilt University
InventorsCraig W. Lindsley, P. Jeffrey Conn, Darren W. Engers, Julie L. Engers, Kayla J. Temple, Aaron M. Bender, Logan A. Baker
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Abstract
Disclosed herein are substituted hexahydro-1H-cyclopenta[c]pyrrole compounds, which may be useful as antagonists of the muscarinic acetylcholine receptor M4 (mAChR M4). Also disclosed herein are methods of making the compounds, pharmaceutical compositions comprising the compounds, and methods of treating disorders using the compounds and compositions.
Claims20
A compound of formula (I):
- or a pharmaceutically acceptable salt thereof, wherein:
- A is an arylene or a five- or six-membered heteroarylene having 1, 2, or 3 heteroatoms independently selected from N, O, and S;
- Q is selected from NRa, O, and —NRb—C(O)—;
- m is 0, 1, or 2;
- R1 is selected from cycloalkyl, Br, —ORC, —NRdRe, and —NHCORf;
- n is 1 or 2;
- each R2 is independently selected from hydrogen, C1-C4 alkyl, halo, and —ORg;
- R3 is selected from hydrogen and C1-C4 alkyl;
- R4 is selected from —(CRhRi)p—Y′, hydrogen, C1-C8 alkyl, and C2-C8 alkenyl;
- R5 is selected from hydrogen, C1-C4 alkyl, halo, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy;
- Y′ is selected from cycloalkyl, cycloalkenyl, heterocycle, aryl, and heteroaryl;
- each Ra, Rb, Rd, Re, Rf, and Rg is independently selected from hydrogen, C1-C4 alkyl, C3-C6 cycloalkyl, and aryl;
- each RC is independently selected from hydrogen, C3-C6 cycloalkyl, and aryl;
- each Rh is independently selected from hydrogen and C1-C4 alkyl;
- each Ri is independently selected from hydrogen, C1-C4 alkyl, C3-C6 cycloalkyl, and aryl;
- and p is 0, 1, 2, 3, or 4;
- wherein each aryl, heteroaryl, arylene, heteroarylene, cycloalkyl, cycloalkenyl, and heterocycle is independently unsubstituted or substituted with 1-5 substituents.
14 more elements
Dependencies are inferred from the claim text.