US 11,884,683 B2
Tricyclic heterocycle compounds useful as HIV integrase inhibitors
Tao Yu, Edison, NJ (US); Alan Whitehead, Scotch Plains, NJ (US); Yili Chen, Hillsborough, NJ (US); Chunrui Sun, Westfield, NJ (US); Zhiyong Hu, Livingston, NJ (US); Kake Zhao, Westfield, NJ (US); Ronald M. Kim, Summit, NJ (US); and John A. McCauley, Maple Glen, PA (US)
Assigned to Merck Sharp & Dohme LLC, Rahway, NJ (US)
Appl. No. 17/057,875
Filed by Merck Sharp & Dohme LLC, Rahway, NJ (US); Tao Yu, Edison, NJ (US); Alan Whitehead, Scotch Plains, NJ (US); Yili Chen, Hillsborough, NJ (US); Chunrui Sun, Westfield, NJ (US); Zhiyong Hu, Livingston, NJ (US); Kake Zhao, Westfield, NJ (US); Ronald M. Kim, Summit, NJ (US); and John A. McCauley, Maple Glen, PA (US)
PCT Filed May 31, 2019, PCT No. PCT/US2019/034783
§ 371(c)(1), (2) Date Nov. 23, 2020,
PCT Pub. No. WO2019/236396, PCT Pub. Date Dec. 12, 2019.
Claims priority of provisional application 62/680,794, filed on Jun. 5, 2018.
Prior Publication US 2021/0309671 A1, Oct. 7, 2021
Int. Cl. C07D 498/22 (2006.01); C07D 471/16 (2006.01); C07D 491/22 (2006.01); A61P 31/18 (2006.01); A61K 45/06 (2006.01)
CPC C07D 498/22 (2013.01) [A61K 45/06 (2013.01); A61P 31/18 (2018.01); C07D 471/16 (2013.01); C07D 491/22 (2013.01)] 17 Claims
 
1. A compound of the formula:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof,
wherein:
each occurrence of R1 is independently halo or C1-3 alkyl, wherein said alkyl groups are optionally substituted with one to three halo;
R2 is hydrogen, methyl or ethyl;
R3 is hydrogen, methyl or ethyl;
R4 is hydrogen, methyl or ethyl;
R5 is hydrogen, C1-3 alkyl, (C1-3 alkyl)OR7 or phenyl;
or R4 and R5 can be taken together with the carbon atom to which they are attached to form a 5- or 6-membered heterocyclyl group;
R6 is hydrogen, C1-6 alkyl or (C1-6 alkyl)OR7;
or R5 and R6 can be taken together with the atoms between them to form a 6-membered heterocyclyl group;
R7 is hydrogen or C1-3 alkyl, which is optionally substituted with one to three halo;
n is an integer between one and three.