US 12,286,428 B2
Tricyclic heteroaryl compounds useful as IRAK4 inhibitors
Satheesh Kesavan Nair, Bangalore (IN); Venkatram Reddy Paidi, Bangalore (IN); Kandhasamy Sarkunam, Hosur (IN); Ramesh Kumar Sistla, Bangalore (IN); John Hynes, Washington Crossing, PA (US); and Natesan Murugesan, Princeton Junction, NJ (US)
Assigned to Bristol-Myers Squibb Company, Princeton, NJ (US)
Appl. No. 17/627,915
Filed by BRISTOL-MYERS SQUIBB COMPANY, Princeton, NJ (US)
PCT Filed Jul. 16, 2020, PCT No. PCT/US2020/042241
§ 371(c)(1), (2) Date Jan. 18, 2022,
PCT Pub. No. WO2021/011724, PCT Pub. Date Jan. 21, 2021.
Claims priority of provisional application 62/875,563, filed on Jul. 18, 2019.
Prior Publication US 2022/0259205 A1, Aug. 18, 2022
Int. Cl. C07D 471/04 (2006.01); C07D 471/14 (2006.01); C07D 491/048 (2006.01)
CPC C07D 471/04 (2013.01) [C07D 471/14 (2013.01); C07D 491/048 (2013.01)] 12 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
or a salt or prodrug thereof, wherein:
W is CR5 or N;
X1 and X2 are independently C or N, provided that zero or one of X1 and X2 is N;
Ring A represented by the structure

OG Complex Work Unit Chemistry
is:

OG Complex Work Unit Chemistry
R1 is —CN or —C(O)NH2;
R2 is hydrogen or —NH(CH3);
R3 is hydrogen or F
R4 is hydrogen, F, or —CH3;
R5 is hydrogen;
each R6 is independently —CH3, —CF3, or —C(CH3)2OH;
Q is

OG Complex Work Unit Chemistry
each R7 is F, C1-3 alkyl, or C1-2 fluoroalkyl;
each R8 is independently hydrogen or —CH2OH;
n is zero, 1, 2, or 3; and
p is zero, 1 or 2.