US 12,304,916 B2
Thienopyridinyl and thiazolopyridinyl compounds useful as IRAK4 inhibitors
Saleem Ahmad, Wall, NJ (US); Ling Li, Pennington, NJ (US); Hong Wu, New Hope, PA (US); and John Hynes, Washington Crossing, PA (US)
Assigned to Bristol-Myers Squibb Company, Princeton, NJ (US)
Appl. No. 17/628,976
Filed by BRISTOL-MYERS SQUIBB COMPANY, Princeton, NJ (US)
PCT Filed Jul. 22, 2020, PCT No. PCT/US2020/042962
§ 371(c)(1), (2) Date Jan. 21, 2022,
PCT Pub. No. WO2021/016289, PCT Pub. Date Jan. 28, 2021.
Claims priority of provisional application 62/877,334, filed on Jul. 23, 2019.
Prior Publication US 2022/0267348 A1, Aug. 25, 2022
Int. Cl. C07D 495/04 (2006.01); C07D 513/04 (2006.01)
CPC C07D 495/04 (2013.01) [C07D 513/04 (2013.01)] 7 Claims
 
1. A compound of Formula (I)

OG Complex Work Unit Chemistry
or a salt thereof, wherein:
X is CR4 or N;
R1 is:
(i) —C(O)NHR1a or —C(O)NH(CH2)1-3R1b; or
(ii) triazolyl substituted with —CH2CH2CH(CH3)2, —CH2CH2CH2OH, —CH2CH2C(CH3)2OH, or —CH2(cyclopropyl);
R1a is:
(i) —CH2CH2CN, —CH2CH2OCH3, —CH2CH2OCH2CH3, —CH2CH2CH(CH3)OH, —CH2CH2S(O)2CH3, —CH2CH2NHS(O)2CH3, —CH2CHFC(CH3)2OH, or —CH2CH2CH2NHS(O)2CH3; or
(ii) cyclobutyl, cyclohexyl, or piperidinyl, each substituted with —OH, —NH2, —C(O)CH3, —OC(O)CH3, —NHC(O)CH3, or —NHC(O)OCH3:
R1b is cyclopropyl, cyclobutyl, pyrrolidinyl, piperidinyl, dioxidothiomorpholinyl, triazolyl, or pyridinyl, each substituted with zero to 3 substituents independently selected from F, —OH, and —CH2OH;
R2 is —CH2CH3, —CH(CH3)2, —CH(CH3)CH2OH, cyclopropyl, cyclopentyl, oxetanyl tetrahydropyranyl, or difluoroethylpyrazolyl;
R3 is R3a or —NHR3a;
R3a is pyrazolyl, thiazolyl, phenyl, pyridinyl, pyridinonyl, pyridazinyl, pyrrolo[2,3-b]pyridinyl, or imidazolo[1,2-a]pyridinyl, each substituted with zero to 1 substituent selected from F, —CN, —CH3, —OCH3, —NH2, —S(O)2CH3, and pyrazolyl; and
each R4 is independently hydrogen, F, Cl, —CH3, or —CF3.