US 11,746,103 B2
ALK-5 inhibitors and uses thereof
Bettina Franz, South Jordan, UT (US); Adam Siddiqui-Jain, South Jordan, UT (US); Steven L. Warner, Sandy, UT (US); Siva Reddy Basireddy, Telangana (IN); Srinivas Padakanti, Telangana (IN); and Naresh Kumar, Telangana (IN)
Assigned to Sumitomo Pharma Oncology, Inc., Marlborough, MA (US)
Filed by Sumitomo Pharma Oncology, Inc., Marlborough, MA (US)
Filed on Apr. 29, 2022, as Appl. No. 17/733,650.
Application 17/733,650 is a continuation of application No. PCT/US2021/072858, filed on Dec. 10, 2021.
Claims priority of provisional application 63/166,621, filed on Mar. 26, 2021.
Claims priority of provisional application 63/123,894, filed on Dec. 10, 2020.
Prior Publication US 2022/0315563 A1, Oct. 6, 2022
Int. Cl. C07D 401/14 (2006.01); C07D 403/12 (2006.01); C07D 403/14 (2006.01); C07D 405/14 (2006.01); C07D 413/14 (2006.01); A61P 35/00 (2006.01); C07D 471/08 (2006.01)
CPC C07D 403/14 (2013.01) [A61P 35/00 (2018.01); C07D 401/14 (2013.01); C07D 403/12 (2013.01); C07D 405/14 (2013.01); C07D 413/14 (2013.01); C07D 471/08 (2013.01)] 27 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
R1 is a C1-C5 alkyl, C3-C5 carbocycle, or a halogen;
R2 is an aryl of at least 6 carbon atoms or nitrogen-containing heteroaryl of at least 6 atoms, optionally substituted with one or more of:
(i) one or more halogens;
(ii) a C1-C6 alkyl optionally substituted with a hydroxyl or one or more halogen wherein, when selected to be an alkyl larger than C3, the alkyl is present at a position on the aryl or heteroaryl of R2 which is meta- or para- to the amino bond to the aryl or heteroaryl of R2;
(iii) a sulfonamide;
(iv) a monocyclic, bicyclic, or spirocyclic carbocycle which is optionally substituted with a hydroxyl, one or more halogen, or one or more linear, branched, or cyclic alkyl moieties of up to 6 carbon atoms which are optionally substituted with hydroxy or one or more halogen, wherein said carbocycle is attached to the aryl or heteroaryl of R2 by a single bond or a methylene or ethylene linker and wherein, when present and selected to be a carbocycle larger than cyclopropyl, the carbocycle is at a position on the aryl or heteroaryl of R2 which is meta- or para- to the amino bond to the aryl or heteroaryl of R2; or
(v) a monocyclic, bicyclic or spirocyclic heterocycle which may contain up to 3 heteroatoms which are selected independently from N and O, and which is optionally and independently substituted with one or more C1-C6 alkyl or C3-C6 carbocycle which are optionally substituted with hydroxy or one or more halogen, wherein said heterocycle is attached to the aryl or heteroaryl of R2 by a single bond or a methylene or ethylene linker and wherein, when present, said heterocycle is at a position on the aryl of R2 which is meta- or para- to the amino bond to said aryl;
R3 is —H, —F, or —Cl;
R4 is —H, a halogen, or a C1-C3 alkyl or cyclopropyl optionally substituted with one or more —F; and
R5 is —H, —F, or a C1-C3 alkyl or cyclopropyl optionally substituted with one or more —F.