US 12,291,532 B2
Substituted xanthines as modulators of TRPC5 activity
Kai Gerlach, Ingelheim am Rhein (DE)
Assigned to Boehringer Ingelheim International GmbH, Ingelheim Am Rhein (DE); and Hydra Biosciences, LLC, Belmont, MA (US)
Appl. No. 17/312,831
Filed by Boehringer Ingelheim International GmbH, Ingelheim am Rhein (DE); and Hydra Biosciences, LLC, Belmont, MA (US)
PCT Filed Dec. 10, 2019, PCT No. PCT/EP2019/084373
§ 371(c)(1), (2) Date Jun. 10, 2021,
PCT Pub. No. WO2020/120449, PCT Pub. Date Jun. 18, 2020.
Claims priority of application No. 18212059 (EP), filed on Dec. 12, 2018.
Prior Publication US 2022/0056032 A1, Feb. 24, 2022
Int. Cl. A61K 31/519 (2006.01); C07D 473/06 (2006.01); C07D 487/04 (2006.01)
CPC C07D 473/06 (2013.01) 25 Claims
 
1. A compound of formula I:

OG Complex Work Unit Chemistry
or a stereoisomer thereof,
wherein:
R1 is CH2CH3, CH(CH3)2, CH2CH(CH3)2, or cyclobutyl;
R2 is:

OG Complex Work Unit Chemistry
R3 is H, P, or C1-C3 alkyl, wherein the C1-C3 alkyl is optionally substituted with one or more F substituents;
R4 is H or F; and
R5 is:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein R5 is further optionally substituted with any one of (a), (b), or (c):
(a) one or more F substituents; or
(b) one or more C1-C3 fluoroalkyl substituents; or
(c) one or more F substituents and one or more C1-C3 fluoroalkyl substituents.
 
4. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or excipient and the compound according to claim 1, or a stereoisomer thereof.