US 2019/0292188 A1 · IMIDAZOPYRIMIDINES AND TRIAZOLOPYRIMIDINES AS A2A / A2B INHIBITORS

Abstract

This application relates to compounds of Formula (I): or pharmaceutically acceptable salts or stereoisomers thereof, which modulate the activity of adenosine receptors, such as subtypes A2A and A2B receptors, and are useful in the treatment of diseases related to the activity of adenosine receptors including, for example, cancer, inflammatory diseases, cardiovascular diseases, and neurodegenerative diseases.

Claims44

Dependent claims

(canceled)

A compound of Formula (I):

or a pharmaceutically acceptable salt thereof;
wherein:
X is N;
R1 is selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, and C1-6 haloalkyl;
R2 is selected from C1-6 alkyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, (4-14 membered heterocycloalkyl)-C1-6 alkyl-, C(O)Rb2, C(O)NRc2Rd2, C(O)ORa2, and NRc2Rd2, wherein the C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- are each optionally substituted with 1, 2, 3, 4, or 5 independently selected RC substituents;
and
wherein the C1-6 alkyl of R2 is substituted with 1, 2, 3, 4, or 5 independently selected RC substituents;
Cy1 is 3-cyanophenyl;
Cy2 is C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, or 4-14 membered heterocycloalkyl, wherein the C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, or 4-14 membered heterocycloalkyl is optionally substituted with 1, 2, 3, 4, 5, 6, 7, or 8 independently selected RF substituents;
each Ra2, Rc2, and Rd2 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of Ra2, Rc2, and Rd2 are each optionally substituted with 1, 2, 3, 4, 5, 6, 7, or 8 independently selected RG substituents;
or any Rc2 and Rd2 attached to the same N atom, together with the N atom to which they are attached, form a 5- or 6-membered heteroaryl or a 4-14 membered heterocycloalkyl group, wherein the 5- or 6-membered heteroaryl or 4-14 membered heterocycloalkyl group is optionally substituted with 1, 2, 3, or 4 independently selected RG substituents;
each Rb2 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of Rb2 are each optionally substituted with 1, 2, 3, 4, 5, 6, 7, or 8 independently selected RG substituents;
each RC, RF, and RG is independently selected from D, halo, oxo, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-54 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, (4-14 membered heterocycloalkyl)-C1-6 alkyl-, CN, NO2, ORa4, SRa4, NHORa4, C(O)Rb4, C(O)NRc4Rd4, C(O)NRc4(Ra4), C(O)ORa4, OC(O)Rb4, OC(O)NRc4Rd4, NRc4Rd4, NRc4NRc4Rd4, NRc4C(O)Rb4, NRe4C(O)ORa4, NRc4C(O)NRc4Rd4, C(═NRe4)Rb4, C(═NRe4)NRc4Rd4, NRc4C(═NRe4)NRc4Rd4, NRc4C(═NRe4)Rb4, NRc4S(O)Rb4, NRc4S(O)NRc4Rd4, NRc4S(O)2Rb4, NRc4S(O)(═NRe4)Rb4, NRc4S(O)2NRc4Rd4, S(O)Rb4, S(O)NRc4Rd4, S(O)2Rb4, S(O)2NRc4Rd4, OS(O)(═NRe4)Rb4, OS(O)2Rb4, SF5, P(O)Rf4Rg4, OP( )(ORh4)(ORi4), P(O)(Rh4)(ORi4), and BRj4Rk4, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of RC, RF, and RG are each optionally substituted with 1, 2, 3, 4, 5, 6, 7, or 8 independently selected RH substituents;
each Ra4, Rc4 and Rd4 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of Ra4, Rc4, and Rd4 are each optionally substituted with 1, 2, 3, 4, 5, 6, 7, or 8 independently selected RH substituents;
or, any Rc4 and Rd4 attached to the same N atom, together with the N atom to which they are attached, optionally form a 5- or 6-membered heteroaryl or a 4-14 membered heterocycloalkyl group, wherein the 5- or 6-membered heteroaryl or 4-14 membered heterocycloalkyl group is optionally substituted with 1, 2, 3, or 4 independently selected RH substituents;
each Rb4 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of Rb4 are each optionally substituted with 1, 2, 3, 4, 5, 6, 7, or 8 independently selected RH substituents;
each Re4 is independently selected from H, OH, CN, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-;
each Rf4 and Rg4 is independently selected from H, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-;
each Rh4 and Ri4 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-;
each Rj4 and Rk4 is independently selected from OH, C1-6 alkoxy, and C1-6 haloalkoxy;
or, any Rj4 and Rk4 attached to the same B atom, together with the B atom to which they are attached, form a 5- or 6-membered heterocycloalkyl group optionally substituted with 1, 2, 3, or 4 substituents independently selected from C1-6 alkyl and C1-6 haloalkyl;
each RH is independently selected from D, halo, oxo, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, (4-14 membered heterocycloalkyl)-C1-6 alkyl-, CN, NO2, ORa5, SRa5, NHORa5, C(O)Rb5, C(O)NRc5Rd5, C(O)NRc5(ORa5), C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)ORa5, NRc5C(O)NRc5Rd5, C(═NRe5)Rb5, C(═NRe5)NRc5Rd5, NRc5C(═NRe5)NRc5Rd5, NRc5C(═NRe5)Rb5, NRc5S(O)Rb5, NRc5S(O)NRc5Rd5, NRc5S(O)2Rb5, NRc5S(O)(═NRe5)Rb5, NRc5S(O)2NRc5Rd5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, S(O)2NRc5Rd5, OS(O)(═NRe5)Rb5, OS(O)2Rb5, SF5, P(O)Rf5Rg5, OP(O)(ORh5)(ORi5), P(O)(ORh5)(ORi5), and BRj5Rk5, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of RH are each optionally substituted with 1, 2, 3, or 4 independently selected RI substituents;
each Ra5, Rc5, and Rd5 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of Ra5, Rc5, and Rd5 are each optionally substituted with 1, 2, 3, or 4 independently selected RI substituents;
or any Rc5 and Rd5 attached to the same N atom, together with the N atom to which they are attached, form a 5- or 6-membered heteroaryl or a 4-14 membered heterocycloalkyl group, wherein the 5- or 6-membered heteroaryl or 4-14 membered heterocycloalkyl group is optionally substituted with 1, 2, 3, or 4 independently selected RI substituents;
each Rb5 is independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of Rb5 are each optionally substituted with 1, 2, 3, or 4 independently selected RI substituents;
each Re5 is independently selected from H, OH, CN, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-;
each Rf5 and Rg5 is independently selected from H, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-;
each Rh5 and Ri5 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-;
each Rj5 and Rk5 is independently selected from OH, C1-6 alkoxy, and C1-6 haloalkoxy;
or, any Rj5 and Rk5 attached to the same B atom, together with the B atom to which they are attached, form a 5- or 6-membered heterocycloalkyl group optionally substituted with 1, 2, 3, or 4 substituents independently selected from C1-6 alkyl and C1-6 haloalkyl;
each RI is independently selected from D, halo, oxo, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-, CN, NO2, ORa6, SRa6, NHORa6, C(O)Rb6, C(O)NRc6Rd6, C(O)NRc6(ORa6), C(O)ORa6, OC(O)Rb6, OC(O)NRc6Rd6, NRc6Rd6, NRc6NRc6Rd6, NRc6C(O)Rb6, NRc6C(O)ORa6, NRc6C(O)NRc6Rd6, C(═NRe6)Rb6, C(═NRe6)NRc6Rd6, NRc6C(═NRe6)NRc6Rd6, NRc6C(═NRe6)Rb6, NRc6S(O)Rb6, NRc6S(O)NRc6Rd6, NRc6S(O)2Rb6, NRc6S(O)(═NRe6)Rb6, NRc6S(O)2NRc6Rd6, S(O)Rb6, S(O)NRc6Rd6, S(O)2Rb6, S(O)2NRc6Rd6, OS(O)(═NRe6)Rb6, OS(O)2Rb6, SF5, P(O)Rf6Rg6, OP(O)(ORh6)(ORi6), P(O)(ORh6)(ORi6), and BRj6Rk6, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of RI are each optionally substituted with 1, 2, 3, or 4 independently selected RJ substituents;
each Ra6, Rc6, and Rd6 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of Ra6, Rc6, and Rd6 are each optionally substituted with 1, 2, 3, or 4 independently selected RJ substituents;
or any Rc6 and Rd6 attached to the same N atom, together with the N atom to which they are attached, form a 5- or 6-membered heteroaryl or a 4-14 membered heterocycloalkyl group, wherein the 5- or 6-membered heteroaryl or 4-14 membered heterocycloalkyl group is optionally substituted with 1, 2, 3, or 4 independently selected RJ substituents;
each Rb6 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of Rb6 are each optionally substituted with 1, 2, 3, or 4 independently selected RJ substituents;
each Re6 is independently selected from H, OH, CN, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-;
each Rf6 and Rg6 is independently selected from H, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-;
each Rh6 and Ri6 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-;
each Rj6 and Rk6 is independently selected from OH, C1-6 alkoxy, and C1-6 haloalkoxy;
or, any Rj6 and Rk6 attached to the same B atom, together with the B atom to which they are attached, form a 5- or 6-membered heterocycloalkyl group optionally substituted with 1, 2, 3, or 4 substituents independently selected from C1-6 alkyl and C1-6 haloalkyl;
each RJ is independently selected from D, halo, oxo, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-, CN, NO2, ORa7, SRa7, NHORa7, C(O)Rb7, C(O)NRc7Rd7, C(O)NRc7(ORa7), C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)ORa7, NRc7C(O)NRc7Rd7, C(═NRe7)Rb7, C(═NRe7)NRc7Rd7, NRc7C(═NRe7)NRc7Rd7, NRc7C(═NRe7)Rb7, NRc7S(O)Rb7, NRc7S(O)NRc7Rd7, NRc7S(O)2Rb7, NRc7S(O)(═NRe7)Rb7, NRc7S(O)2NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, S(O)2NRc7Rd7, OS(O)(═NRe7)Rb7, OS(O)2Rb7, SF5, P(O)Rf7Rg7, OP(O)(ORh7)(ORi7), P(O)(ORh7)(ORi7), and BRj7Rk7, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of RJ are each optionally substituted with 1, 2, 3, or 4 independently selected RK substituents;
each Ra7, Rc7, and Rd7 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of Ra7, Rc7, and Rd7 are each optionally substituted with 1, 2, 3, or 4 independently selected RK substituents;
or any Rc7 and Rd7 attached to the same N atom, together with the N atom to which they are attached, form a 5- or 6-membered heteroaryl or a 4-14 membered heterocycloalkyl group, wherein the 5- or 6-membered heteroaryl or 4-14 membered heterocycloalkyl group is optionally substituted with 1, 2, 3, or 4 independently selected RK substituents;
each Rb7 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl- of Rb7 are each optionally substituted with 1, 2, 3, or 4 independently selected RK substituents;
each Re7 is independently selected from H, OH, CN, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, and 4-14 membered heterocycloalkyl;
each Rf7 and Rg7 is independently selected from H, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-;
each Rh7 and Ri7 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-;
each Rj7 and Rk7 is independently selected from OH, C1-6 alkoxy, and C1-6 haloalkoxy;
or, any Rj7 and Rk7 attached to the same B atom, together with the B atom to which they are attached, form a 5- or 6-membered heterocycloalkyl group optionally substituted with 1, 2, 3, or 4 substituents independently selected from C1-6 alkyl and C1-6 haloalkyl;
each RK is independently selected from H, D, OH, halo, oxo, CN, C(O)OH, NH2, NO2, SF5, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-14 aryl, C3-14 cycloalkyl, 5-14 membered heteroaryl, 4-14 membered heterocycloalkyl, C6-14 aryl-C1-6 alkyl-, C3-14 cycloalkyl-C1-6 alkyl-, (5-14 membered heteroaryl)-C1-6 alkyl-, and (4-14 membered heterocycloalkyl)-C1-6 alkyl-;
and
wherein any heteroaryl group of any of the above-recited substituents optionally comprises an N-oxide on any ring-forming nitrogen.

48 more elements

Dependencies are inferred from the claim text.

Imidazopyrimidines and triazolopyrimidines as a2a / a2b inhibitors

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Imidazopyrimidines and triazolopyrimidines as a2a / a2b inhibitors

Life of this patent

Abstract

Claims44