US 11,932,634 B2
Diacylglycerol kinase modulating compounds
Michael Graupe, Pacifica, CA (US); Juan A. Guerrero, Clayton, CA (US); Stephen D. Holmbo, Kirkland, WA (US); Jesse M. Jacobsen, Seattle, WA (US); Tetsuya Kobayashi, Pleasanton, CA (US); Leena B. Patel, Seattle, WA (US); Heath A. Weaver, Seattle, WA (US); Jie Xu, Foster City, CA (US); and Suet C. Yeung, Redmond, WA (US)
Assigned to Gilead Sciences, Inc., Foster City, CA (US)
Filed by Gilead Sciences, Inc., Foster City, CA (US)
Filed on Jun. 21, 2022, as Appl. No. 17/845,469.
Claims priority of provisional application 63/213,893, filed on Jun. 23, 2021.
Prior Publication US 2023/0060004 A1, Feb. 23, 2023
Int. Cl. C07D 413/14 (2006.01); C07D 239/95 (2006.01); C07D 401/04 (2006.01); C07D 401/12 (2006.01); C07D 401/14 (2006.01); C07D 403/12 (2006.01); C07D 413/04 (2006.01); C07D 417/12 (2006.01); C07D 471/04 (2006.01)
CPC C07D 413/14 (2013.01) [C07D 239/95 (2013.01); C07D 401/04 (2013.01); C07D 401/12 (2013.01); C07D 401/14 (2013.01); C07D 403/12 (2013.01); C07D 413/04 (2013.01); C07D 417/12 (2013.01); C07D 471/04 (2013.01); C07B 2200/05 (2013.01)] 20 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein
R1 is hydrogen, C1-6 alkyl, or halogen;
R2 is hydrogen, C1-6 alkyl, or halogen;
R3 is hydrogen, C1-6 alkyl, or halogen;
R4 is hydrogen, C1-6 alkyl, or halogen;
R7 is hydrogen or C1-6 alkyl optionally substituted with —OH;
R5 is C1-6 alkyl or C1-6 haloalkyl;
R6 is phenyl substituted with C2-8 alkynyl, the alkynyl is substituted with 1 or 2 R6j which can be the same or different; the phenyl of R6 is optionally substituted with one additional R6a;
or

OG Complex Work Unit Chemistry
is

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
n is 0, 1, or 2;
each R6a is independently halogen, C2-8 alkynyl, phenyl, heterocycloalkyl, or heteroaryl, wherein the phenyl, heterocycloalkyl, or heteroaryl is each optionally substituted with 1 to 3 R6e, and the alkynyl is optionally substituted with 1 to 4 R6j which can be the same or different, wherein the heterocycloalkyl is a 3 to 10 membered ring having 1 to 3 heteroatoms each independently N, O or S, and the heteroaryl is a 5 or 6 membered ring having 1 to 3 heteroatoms each independently N, O or S;
each R6j is independently halogen, C1-6 haloalkyl, —OR6j1, —CN, —N(R6j1)(R6j2), —N(R6j1)C(O)R6j2, C3-10 cycloalkyl, heteroaryl, or heterocycloalkyl, wherein the cycloalkyl, heteroaryl, or heterocycloalkyl is optionally substituted with 1 to 3 R6p which can be the same or different, the heterocycloalkyl is a 3 to 10 membered ring having 1 to 3 heteroatoms each independently N, O or S; and the heteroaryl is a 5 or 6 membered ring having 1 to 3 heteroatoms each independently N, O or S;
each R6j1 and R6j2 independently hydrogen, C1-6 alkyl, C1-6 haloalkyl, or C3-10 cycloalkyl optionally substituted with C1-6 haloalkyl;
each R6p is independently halogen, C1-6 alkyl, C1-6 haloalkyl, —C(O)R6p1, or heterocycloalkyl, the heterocycloalkyl is a 3 to 10 membered ring having 1 to 3 heteroatoms each independently N, O or S;
R6p1 is C1-6 alkyl, or C3-10 cycloalkyl;
each R6e is independently C1-6 alkyl, C3-6 cycloalkyl, heterocycloalkyl, halogen, C1-6 haloalkyl, or —CN, wherein the cycloalkyl and heterocycloalkyl are optionally substituted with 1 to 3 R6h which can be the same or different, and the heterocycloalkyl is a 3 to 10 membered ring having 1 to 3 heteroatoms each independently N, O or S;
and each R6h is independently C1-6 alkyl, C1-6 haloalkyl, ═O, or —OH.