Substituted imidazo[1,2-a]pyrazines as LSD1 inhibitors
View Patent ↗The present invention is directed to imidazo[1,2-a]pyrazine derivatives of Formula I, or a pharmaceutically acceptable salt thereof, which are LSD1 inhibitors useful in the treatment of diseases such as cancer.
1. A compound of Formula I:
or a pharmaceutically acceptable salt thereof, wherein:
Ring A is C 6-10 aryl or 5-10 membered heteroaryl comprising carbon and 1, 2, 3, or 4 heteroatoms selected from N, O, and S, wherein said C 6-10 aryl and 5-10 membered heteroaryl are each optionally substituted by 1, 2, 3, or 4 substituents independently selected from R A ;
Ring B is C 6-10 aryl; 5-10 membered heteroaryl comprising carbon and 1, 2, 3 or 4 heteroatoms selected from N, O, and S; C 3-10 cycloalkyl; or 4-10 membered heterocycloalkyl comprising carbon and 1, 2, 3 or 4 heteroatoms selected from N, O, and S; wherein said C 6-10 aryl, 5-10 membered heteroaryl, C 3-10 cycloalkyl, and 4-10 membered heterocycloalkyl are each optionally substituted by 1, 2, 3, or 4 substituents independently selected from R B ;
R 1 is halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, Cy 1 , CN, OR a1 , SR a1 , C(O)R b1 , C(O)NR c1 R d1 , C(O)OR a1 , OC(O)R b1 , OC(O)NR c1 R d1 , NR c1 R d1 , NR c1 C(O)R b1 , NR c1 C(O)OR a1 , NR c1 C(O)NR c1 R d1 , C(═NR e1 )R b1 , C(═NR e1 )NR c1 R d1 , NR c1 C(═NR e1 )NR c1 R d1 , NR c1 S(O)R b1 , NR c1 S(O) 2 R b1 , NR c1 S(O) 2 NR c1 R d1 , S(O)R b1 , S(O)NR c1 R d1 , S(O) 2 R b1 , or S(O) 2 NR c1 R d1 ; wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted with 1, 2, or 3 substituents independently selected from Cy 1 , halo, CN, OH, OR a1 , SR a1 , C(O)R b1 , C(O)NR c1 R d1 , C(O)OR a1 , OC(O)R b1 , OC(O)NR c1 R d1 , NR c1 R d1 , NR c1 C(O)R b1 , NR c1 C(O)OR a1 , NR c1 C(O)NR c1 R d1 , C(═NR e1 )R b1 , C(═NR e1 )NR c1 R d1 , NR c1 C(═NR e1 )NR c1 R d1 , NR c1 S(O)R b1 , NR c1 S(O) 2 R b1 , NR c1 S(O) 2 NR c1 R d1 , S(O)R b1 , S(O)NR c1 R d1 , S(O) 2 R b1 , and S(O) 2 NR c1 R d1 ;
R 2 and R 3 are each independently selected from H, halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, Cy 2 , CN, OR a2 , SR a2 , C(O)R b2 , C(O)NR c2 R d2 , C(O)OR a2 , OC(O)R b2 , OC(O)NR c2 R d2 , NR c2 R d2 , NR c2 C(O)R b2 , NR c2 C(O)OR a2 , NR c2 C(O)NR c2 R d2 , C(═NR e2 )R b2 , C(═NR e2 )NR c2 R d2 , NR c2 C(═NR e2 )NR c2 R d2 , NR c2 S(O)R b2 , NR c2 S(O) 2 R b2 , NR c2 S(O) 2 NR c2 R d2 , S(O)R b2 , S(O)NR c2 R d2 , S(O) 2 R b2 , and S(O) 2 NR c2 R d2 ; wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted with 1, 2, or 3 substituents independently selected from Cy 2 , halo, CN, OR a2 , SR a2 , C(O)R b2 , C(O)NR c2 R d2 , C(O)OR a2 , OC(O)R b2 , OC(O)NR c2 R d2 , NR c2 R d2 , NR c2 C(O)R b2 , NR c2 C(O)OR a2 , NR c2 C(O)NR c2 R d2 , C(═NR e2 )R b2 , C(═NR e2 )NR c2 R d2 , NR c2 C(═NR e2 )NR c2 R d2 , NR c2 S(O)R b2 , NR c2 S(O) 2 R b2 , NR c2 S(O) 2 NR c2 R d2 , S(O)R b2 , S(O)NR c2 R d2 , S(O) 2 R b2 , and S(O) 2 NR c2 R d2 ;
each R A is independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, CN, NO 2 , OR a4 , SR a4 , C(O)R b4 , C(O)NR c4 R d4 , C(O)OR a4 , OC(O)R b4 , OC(O)NR c4 R d4 , NR c4 R d4 , NR c4 C(O)R b4 , NR c4 C(O)OR a4 , NR c4 C(O)NR c4 R d4 , C(═NR e4 )R b4 , C(═NR e4 )NR c4 R d4 , NR c4 C(═NR e4 )NR c4 R d4 , NR c4 S(O)R b4 , NR c4 S(O) 2 R b4 , NR c4 S(O) 2 NR c4 R d4 , S(O)R b4 , S(O)NR c4 R d4 , S(O) 2 R b4 , and S(O) 2 NR c4 R d4 , wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted by 1, 2, or 3, substituents independently selected from halo, C 1-6 haloalkyl, CN, NO 2 , OR a4 , SR a4 , C(O)R b4 , C(O)NR c4 R d4 , C(O)OR a4 , OC(O)R b4 , OC(O)NR c4 R d4 , NR c4 R d4 , NR c4 C(O)R b4 , NR c4 C(O)OR a4 , NR c4 C(O)NR c4 R d4 , C(═NR e4 )R b4 , C(═NR e4 )NR c4 R d4 , NR c4 C(═NR e4 )NR c4 R d4 , NR c4 S(O)R b4 , NR c4 S(O) 2 R b4 , NR c4 S(O) 2 NR c4 R d4 , S(O)R b4 , S(O)NR c4 R d4 , S(O) 2 R b4 , and S(O) 2 NR c4 R d4 ;
each R B is independently selected from Cy 3 , halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, CN, NO 2 , OR a5 , SR a5 , C(O)R b5 , C(O)NR c5 R d5 , C(O)OR a5 , OC(O)R b5 , OC(O)NR c5 R d5 , NR c5 R d5 , NR c5 C(O)R b5 , NR c5 C(O)OR a5 , NR c5 C(O)NR c5 R d5 , C(═NR e5 )R b5 , C(═NR e5 )NR c5 R d5 , NR c5 C(═NR e5 )NR c5 R d5 , NR c5 S(O)R b5 , NR c5 S(O) 2 R b5 , NR c5 S(O) 2 NR c5 R d5 , S(O)R b5 , S(O)NR c5 R d5 , S(O) 2 R b5 , and S(O) 2 NR c5 R d5 , wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted by 1, 2, or 3 substituents independently selected from Cy 3 , halo, C 1-6 haloalkyl, CN, NO 2 , OR a5 , SR a5 , C(O)R b5 , C(O)NR c5 R d5 , C(O)OR a5 , OC(O)R b5 , OC(O)NR c5 R d5 , NR c5 R d5 , NR c5 C(O)R b5 , NR c5 C(O)OR a5 , NR c5 C(O)NR c5 R d5 , C(═NR e5 )R b5 , C(═NR e5 )NR c5 R d5 , NR c5 C(═NR e5 )NR c5 R d5 , NR c5 S(O)R b5 , NR c5 S(O) 2 R b5 , NR c5 S(O) 2 NR c5 R d5 , S(O)R b5 , S(O)NR c5 R d5 , S(O) 2 R b5 , and S(O) 2 NR c5 R d5 ;
each Cy 1 , Cy 2 , Cy 3 , and Cy 4 is independently selected from C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, and 4-10 membered heterocycloalkyl, each of which is optionally substituted with 1, 2, 3, or 4 substituents independently selected from R Cy ;
each R Cy is independently selected from halo, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, C 2-6 alkenyl, C 2-6 alkynyl, phenyl, C 3-7 cycloalkyl, 5-6 membered heteroaryl, 4-7 membered heterocycloalkyl, phenyl-C 1-4 alkyl-, C 3-7 cycloalkyl-C 1-4 alkyl-, (5-6 membered heteroaryl)-C 1-4 alkyl-, and (4-7 membered heterocycloalkyl)-C 1-4 alkyl-, CN, NO 2 , OR a6 , SR a6 , C(O)R b6 , C(O)NR c6 R d6 , C(O)OR a6 , OC(O)R b6 , OC(O)NR c6 R d6 , C(═NR e6 )NR c6 R d6 , NR c6 C(═NR e6 )NR c6 R d6 , NR c6 R d6 , NR c6 C(O)R b6 , NR c6 C(O)OR a6 , NR c6 C(O)NR c6 R d6 , NR c6 S(O)R b6 , NR c6 S(O) 2 R b6 , NR c6 S(O) 2 NR c6 R d6 , S(O)R b6 , S(O)NR c6 R d6 , S(O) 2 R b6 , and S(O) 2 NR c6 R d6 , wherein said C 1-4 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, phenyl, C 3-7 cycloalkyl, 5-6 membered heteroaryl, 4-7 membered heterocycloalkyl, phenyl-C 1-4 alkyl-, C 3-7 cycloalkyl-C 1-4 alkyl-, (5-6 membered heteroaryl)-C 1-4 alkyl-, and (4-7 membered heterocycloalkyl)-C 1-4 alkyl- are each optionally substituted by 1, 2, or 3 substituents independently selected from C 1-6 alkyl, C 1-4 haloalkyl, C 1-6 cyanoalkyl, halo, CN, NO 2 , OR a6 , SR a6 , C(O)R b6 , C(O)NR c6 R d6 , C(O)OR a6 , OC(O)R b6 , OC(O)NR c6 R d6 , C(═NR e6 )NR c6 R d6 , NR c6 C(═NR e6 )NR c6 R d6 , NR c6 R d6 , NR c6 C(O)R b6 , NR c6 C(O)OR a6 , NR c6 C(O)NR c6 R d6 , NR c6 S(O)R b6 , NR c6 S(O) 2 R b6 , NR c6 S(O) 2 NR c6 R d6 , S(O)R b6 , S(O)NR c6 R d6 , S(O) 2 R b6 , and S(O) 2 NR c6 R d6 ;
each R a1 is independently selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, and Cy 4 ; wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted with 1, 2, or 3 substituents independently selected from Cy 4 , halo, CN, OR a3 , SR a3 , C(O)R b3 , C(O)NR c3 R d3 , C(O)OR a3 , OC(O)R b3 , OC(O)NR c3 R d3 , NR c3 R d3 , NR c3 C(O)R b3 , NR c3 C(O)OR a3 , NR c3 C(O)NR c3 R d3 , C(═NR e3 )R b3 , C(═NR e3 )NR c3 R d3 , NR c3 C(═NR e3 )NR c3 R d3 , NR c3 S(O)R b3 , NR c3 S(O) 2 R b3 , NR c3 S(O) 2 NR c3 R d3 , S(O)R b3 , S(O)NR c3 R d3 , S(O) 2 R b3 , and S(O) 2 NR c3 R d3 ;
each R b1 , R c1 , and R d1 is independently selected from H, C 1-6 alkyl, C 1-4 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl-, wherein said C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl- are each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
or any R c1 and R d1 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C 1-6 alkyl, C 3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C 6-10 aryl, 5-6 membered heteroaryl, C 1-6 haloalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 , wherein said C 1-6 alkyl, C 3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C 6-10 aryl, and 5-6 membered heteroaryl are each optionally substituted by 1, 2, or 3 substituents independently selected from halo, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
each R a2 , R b2 , R c2 , and R d2 is independently selected from H, C 1-6 alkyl, C 1-4 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl-, wherein said C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl- are each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
or any R c2 and R d2 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C 1-6 alkyl, C 3-7 cycloalkyl, 4-7 membered heterocycloalkyl, phenyl, 5-6 membered heteroaryl, C 1-6 haloalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 , wherein said C 1-6 alkyl, C 3-7 cycloalkyl, 4-7 membered heterocycloalkyl, phenyl, and 5-6 membered heteroaryl are each optionally substituted by 1, 2, or 3 substituents independently selected from halo, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
each R a3 , R b3 , R c3 , and R d3 is independently selected from H, C 1-6 alkyl, C 1-4 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl-, wherein said C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl- are each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
or any R c3 and R d3 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C 1-6 alkyl, C 3-7 cycloalkyl, 4-7 membered heterocycloalkyl, phenyl, 5-6 membered heteroaryl, C 1-6 haloalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 , wherein said C 1-6 alkyl, C 3-7 cycloalkyl, 4-7 membered heterocycloalkyl, phenyl, and 5-6 membered heteroaryl are each optionally substituted by 1, 2, or 3 substituents independently selected from halo, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
each R a4 , R b4 , R c4 , and R d4 is independently selected from H, C 1-6 alkyl, C 1-4 haloalkyl, C 2-6 alkenyl, and C 2-6 alkynyl, wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
or any R c4 and R d4 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C 1-6 alkyl, C 1-6 haloalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
each R a5 , R b5 , R c5 , and R d5 is independently selected from H, C 1-6 alkyl, C 1-4 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl-, wherein said C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl- are each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
or any R c5 and R d5 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C 1-6 alkyl, C 3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C 6-10 aryl, 5-6 membered heteroaryl, C 1-6 haloalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 , wherein said C 1-6 alkyl, C 3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C 6-10 aryl, and 5-6 membered heteroaryl are each optionally substituted by 1, 2, or 3 substituents independently selected from halo, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
each R a6 , R b6 , R c6 , and R d6 is independently selected from H, C 1-6 alkyl, C 1-4 haloalkyl, C 2-6 alkenyl, and C 2-6 alkynyl, wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
or any R c6 and R d6 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C 1-6 alkyl, C 1-6 haloalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
each R a7 , R b7 , R c7 , and R d7 is independently selected from H, C 1-4 alkyl, C 1-4 haloalkyl, C 2-4 alkenyl, and C 2-4 alkynyl, wherein said C 1-4 alkyl, C 2-4 alkenyl, and C 2-4 alkynyl are each optionally substituted with 1, 2, or 3 substituents independently selected from OH, CN, amino, halo, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkylthio, C 1-4 alkylamino, di(C 1-4 alkyl)amino, C 1-4 haloalkyl, and C 1-4 haloalkoxy; and
each R e1 , R e2 , R e3 , R e4 , R e5 , R e6 , and R e7 is independently selected from H, C 1-4 alkyl, and CN.
2. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:
Ring A is phenyl optionally substituted by 1, 2, or 3 substituents independently selected from R A ;
Ring B is phenyl or 5-6 membered heteroaryl comprising carbon and 1 or 2 heteroatoms selected from N; wherein said phenyl or 5-6 membered heteroaryl is optionally substituted by 1, or 2 substituents independently selected from R B ;
R 1 is halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, Cy 1 , CN, OR a1 , SR a1 , C(O)R b1 , C(O)NR c1 R d1 , C(O)OR a1 , OC(O)R b1 , OC(O)NR c1 R d1 , NR c1 R d1 , NR c1 C(O)R b1 , NR c1 C(O)OR a1 , NR c1 C(O)NR c1 R d1 , NR c1 S(O)R b1 , NR c1 S(O) 2 R b1 , NR c1 S(O) 2 NR c1 R d1 , S(O)R b1 , S(O)NR c1 R d1 , S(O) 2 R b1 , or S(O) 2 NR c1 R d1 ; wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted with 1, 2, or 3 substituents independently selected from Cy 1 , halo, CN, OH, OR a1 , SR a1 , C(O)R b1 , C(O)NR c1 R d1 , C(O)OR a1 , OC(O)R b1 , OC(O)NR c1 R d1 , NR c1 R d1 , NR c1 C(O)R b1 , NR c1 C(O)OR a1 , NR c1 C(O)NR c1 R d1 , NR c1 S(O)R b1 , NR c1 S(O) 2 R b1 , NR c1 S(O) 2 NR c1 R d1 , S(O)R b1 , S(O)NR c1 R d1 , S(O) 2 R b1 , and S(O) 2 NR c1 R d1 ;
R 2 is H, halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, Cy 2 , CN, OR a2 , SR a2 , C(O)R b2 , C(O)NR c2 R d2 , C(O)OR a2 , OC(O)R b2 , OC(O)NR c2 R d2 , NR c2 R d2 , NR c2 C(O)R b2 , NR c2 C(O)OR a2 , NR c2 C(O)NR c2 R d2 , NR c2 S(O)R b2 , NR c2 S(O) 2 R b2 , NR c2 S(O) 2 NR c2 R d2 , S(O)R b2 , S(O)NR c2 R d2 , S(O) 2 R b2 , or S(O) 2 NR c2 R d2 ; wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted with 1, 2, or 3 substituents independently selected from Cy 2 , halo, CN, OR a2 , SR a2 , C(O)R b2 , C(O)NR c2 R d2 , C(O)OR a2 , OC(O)R b2 , OC(O)NR c2 R d2 , NR c2 R d2 , NR c2 C(O)R b2 , NR c2 C(O)OR a2 , NR c2 C(O)NR c2 R d2 , NR c2 S(O)R b2 , NR c2 S(O) 2 R b2 , NR c2 S(O) 2 NR c2 R d2 , S(O)R b2 , S(O)NR c2 R d2 , S(O) 2 R b2 , and S(O) 2 NR c2 R d2 ;
R 3 is H;
each R A is independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, CN, OR a4 , SR a4 , C(O)R b4 , C(O)NR c4 R d4 , NR c4 R d4 , NR c4 C(O)R b4 , NR c4 S(O) 2 R b4 , S(O)R b4 , S(O)NR c4 R d4 , S(O) 2 R b4 , and S(O) 2 NR c4 R d4 , wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted by 1, 2, or 3, substituents independently selected from halo, C 1-6 haloalkyl, CN, OR a4 , SR a4 , C(O)R b4 , C(O)NR c4 R d4 , NR c4 R d4 , NR c4 C(O)R b4 , NR c4 S(O) 2 R b4 , S(O)R b4 , S(O)NR c4 R d4 , S(O) 2 R b4 , and S(O) 2 NR c4 R d4 ;
each R B is independently selected from Cy 3 , halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, CN, OR a5 , SR a5 , C(O)R b5 , C(O)NR c5 R d5 , C(O)OR a5 , OC(O)R b5 , OC(O)NR c5 R d5 , NR c5 R d5 , NR c5 C(O)R b5 , NR c5 C(O)OR a5 , NR c5 C(O)NR c5 R d5 , NR c5 S(O)R b5 , NR c5 S(O) 2 R b5 , NR c5 S(O) 2 NR c5 R d5 , S(O)R b5 , S(O)NR c5 R d5 , S(O) 2 R b5 , and S(O) 2 NR c5 R d5 , wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted by 1, 2, or 3 substituents independently selected from Cy 3 , halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, CN, OR a5 , SR a5 , C(O)R b5 , C(O)NR c5 R d5 , C(O)OR a5 , OC(O)R b5 , OC(O)NR c5 R d5 , NR c5 R d5 , NR c5 C(O)R b5 , NR c5 C(O)OR a5 , NR c5 C(O)NR c5 R d5 , NR c5 S(O)R b5 , NR c5 S(O) 2 R b5 , NR c5 S(O) 2 NR c5 R d5 , S(O)R b5 , S(O)NR c5 R d5 , S(O) 2 R b5 , and S(O) 2 NR c5 R d5 ;
each Cy 1 , Cy 2 , Cy 3 , and Cy 4 is independently selected from C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, and 4-10 membered heterocycloalkyl, each of which is optionally substituted with 1, 2, 3, or 4 substituents independently selected from R Cy ;
each R Cy is selected from halo, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, C 2-6 alkenyl, C 2-6 alkynyl, phenyl, C 3-7 cycloalkyl, 5-6 membered heteroaryl, 4-7 membered heterocycloalkyl, phenyl-C 1-4 alkyl-, C 3-7 cycloalkyl-C 1-4 alkyl-, (5-6 membered heteroaryl)-C 1-4 alkyl-, and (4-7 membered heterocycloalkyl)-C 1-4 alkyl-, CN, NO 2 , OR a6 , SR a6 , C(O)R b6 , C(O)NR c6 R d6 , C(O)OR a6 , OC(O)R b6 , OC(O)NR c6 R d6 , NR c6 R d6 , NR c6 C(O)R b6 , NR c6 C(O)OR a6 , NR c6 C(O)NR c6 R d6 , NR c6 S(O)R b6 , NR c6 S(O) 2 R b6 , NR c6 S(O) 2 NR c6 R d6 , S(O)R b6 , S(O)NR c6 R d6 , S(O) 2 R b6 , and S(O) 2 NR c6 R d6 , wherein said C 1-4 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, phenyl, C 3-7 cycloalkyl, 5-6 membered heteroaryl, 4-7 membered heterocycloalkyl, phenyl-C 1-4 alkyl-, C 3-7 cycloalkyl-C 1-4 alkyl-, (5-6 membered heteroaryl)-C 1-4 alkyl-, and (4-7 membered heterocycloalkyl)-C 1-4 alkyl- are each optionally substituted by 1, 2, or 3 substituents independently selected from C 1-6 alkyl, C 1-4 haloalkyl, C 1-6 cyanoalkyl, halo, CN, NO 2 , OR a6 , SR a6 , C(O)R b6 , C(O)NR c6 R d6 , C(O)OR a6 , OC(O)R b6 , OC(O)NR c6 R d6 , NR c6 R d6 , NR c6 C(O)R b6 , NR c6 C(O)OR a6 , NR c6 C(O)NR c6 R d6 , NR c6 S(O)R b6 , NR c6 S(O) 2 R b6 , NR c6 S(O) 2 NR c6 R d6 , S(O)R b6 , S(O)NR c6 R d6 , S(O) 2 R b6 , and S(O) 2 NR c6 R d6 ;
each R a1 is independently selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, and Cy 4 ; wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted with 1, 2, or 3 substituents independently selected from Cy 4 , halo, CN, OR a3 , SR a3 , C(O)R b3 , C(O)NR c3 R d3 , C(O)OR a3 , OC(O)R b3 , OC(O)NR c3 R d3 , NR c3 R d3 , NR c3 C(O)R b3 , NR c3 C(O)OR a3 , NR c3 C(O)NR c3 R d3 , NR c3 S(O)R b3 , NR c3 S(O) 2 R b3 , NR c3 S(O) 2 NR c3 R d3 , S(O)R b3 , S(O)NR c3 R d3 , S(O) 2 R b3 , and S(O) 2 NR c3 R d3 ;
each R b1 , R c1 , and R d1 is independently selected from H, C 1-6 alkyl, C 1-4 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl-, wherein said C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl- are each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
or any R c1 and R d1 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C 1-6 alkyl, C 3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C 6-10 aryl, 5-6 membered heteroaryl, C 1-6 haloalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 , wherein said C 1-6 alkyl, C 3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C 6-10 aryl, and 5-6 membered heteroaryl are each optionally substituted by 1, 2, or 3 substituents independently selected from halo, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , C(═NR e7 )NR c7 R d7 , NR c7 C(═NR e7 )NR c7 R d7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
each R a2 , R b2 , R c2 , and R d2 is independently selected from H, C 1-6 alkyl, C 1-4 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl-, wherein said C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl- are each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
each R a3 , R b3 , R c3 , and R d3 is independently selected from H, C 1-6 alkyl, C 1-4 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl-, wherein said C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-4 alkyl-, C 3-10 cycloalkyl-C 1-4 alkyl-, (5-10 membered heteroaryl)-C 1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C 1-4 alkyl- are each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, halo, CN, OR a7 , SR a7 , C(O)R b7 , C(O)NR c7 R d7 , C(O)OR a7 , OC(O)R b7 , OC(O)NR c7 R d7 , NR c7 R d7 , NR c7 C(O)R b7 , NR c7 C(O)NR c7 R d7 , NR c7 C(O)OR a7 , S(O)R b7 , S(O)NR c7 R d7 , S(O) 2 R b7 , NR c7 S(O) 2 R b7 , NR c7 S(O) 2 NR c7 R d7 , and S(O) 2 NR c7 R d7 ;
each R a4 , R b4 , R c4 , and R d4 is independently selected from H and C 1-3 alkyl;
each R a5 , R b5 , R c5 , and R d5 , is independently selected from H or C 1-3 alkyl;
each R a6 , R b6 , R c6 , and R d6 is independently selected from H or C 1-3 alkyl; and
each R a7 , R b7 , R c7 , and R d7 is independently selected from H or C 1-3 alkyl.
3. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:
Ring A is phenyl optionally substituted by 1, 2, or 3 substituents independently selected from R A ;
Ring B is phenyl, pyridyl, or pyrimidinyl, each optionally substituted by 1 or 2 substituents independently selected from R B ;
R 1 is halo, C 1-3 alkyl, Cy 1 , OR a1 , SR a1 , C(O)NR c1 R d1 , NR c1 R d1 , NR c1 C(O)R b1 , or NR c1 C(O)NR c1 R d1 ; wherein said C 1-3 alkyl is optionally substituted with 1, 2, or 3 substituents independently selected from Cy 1 , halo, CN, OH, OR a1 , C(O)NR c1 R d1 , NR c1 R d1 , and NR c1 C(O)R b1 ;
R 2 is H, halo, C 1-3 alkyl, C 1-3 haloalkyl, Cy 2 , C(O)NR c2 R d2 , NR c2 R d2 , or NR c2 C(O)R b2 ; wherein said C 1-3 alkyl is optionally substituted with 1, 2, or 3 substituents independently selected from Cy 2 , halo, CN, OR a2 , C(O)NR c2 R d2 , NR c2 R d2 , and NR c2 C(O)R b2 ;
R 3 is H;
each R A is independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, CN, OR a4 , SR a4 , C(O)R b4 , C(O)NR c4 R d4 , NR c4 R d4 , NR c4 C(O)R b4 NR c4 S(O) 2 R b4 , S(O)R b4 , S(O)NR c4 R d4 , S(O) 2 R b4 , and S(O) 2 NR c4 R d4 , wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted by 1, 2, or 3, substituents independently selected from halo, C 1-6 haloalkyl, CN, OR a4 , SR a4 , C(O)R b4 , C(O)NR c4 R d4 , NR c4 R d4 , NR c4 C(O)R b4 , NR c4 S(O) 2 R b4 , S(O)R b4 , S(O)NR c4 R d4 , S(O) 2 R b4 , and S(O) 2 NR c4 R d4 ;
each R B is independently selected from Cy 3 , halo, C 1-6 alkyl, C 1-6 haloalkyl, CN, OR a5 , C(O)NR c5 R d5 , NR c5 R d5 , NR c5 C(O)R b5 , NR c5 C(O)OR a5 , NR c5 C(O)NR c5 R d5 , NR c5 S(O)R b5 , NR c5 S(O) 2 R b , and NR c5 S(O) 2 NR c5 R d5 , wherein said C 1-6 alkyl is optionally substituted by 1, 2, or 3 substituents independently selected from Cy 3 , halo, C 1-6 haloalkyl, CN, OR a5 , C(O)NR c5 R d5 , NR c5 R d5 , and NR c5 C(O)R b5 ;
each Cy 1 , Cy 2 , Cy 3 , and Cy 4 is independently selected from phenyl, cyclopropyl, azetidinyl, piperidinyl, pyrrolidinyl, diazapanyl, and diazaspirononanyl, each of which is optionally substituted with 1 or 2 substituents independently selected from R Cy ;
each R Cy is independently selected from halo, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, CN, OR a6 , and NR c6 R d6 ;
each R a1 is independently selected from C 1-3 alkyl and Cy 4 ; wherein said C 1-3 alkyl is optionally substituted with 1, 2, or 3 substituents independently selected from Cy 4 , halo, CN, and OR a3 , and NR c3 R d3 ;
each R b1 , R c1 , and R d1 is independently selected from H, C 1-3 alkyl, C 1-3 haloalkyl, phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyridinyl, pyrimidinyl, azetidinyl, piperidinyl, pyrrolidinyl, thiazolyl, phenyl-C 1-2 alkyl-, cyclopropyl-C 1-2 alkyl-, cyclobutyl-C 1-2 alkyl-, cyclopentyl-C 1-2 alkyl-, cyclohexyl-C 1-2 alkyl-, pyridinyl-C 1-2 alkyl-, pyrimidinyl-C 1-2 alkyl-, azetidinyl-C 1-2 alkyl-, piperidinyl-C 1-2 alkyl-, pyrrolidinyl-C 1-2 alkyl-, and thiazolyl-C 1-2 alkyl-, wherein said C 1-3 alkyl, C 1-3 haloalkyl, phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyridinyl, pyrimidinyl, azetidinyl, piperidinyl, pyrrolidinyl, thiazolyl, phenyl-C 1-2 alkyl-, cyclopropyl-C 1-2 alkyl-, cyclobutyl-C 1-2 alkyl-, cyclopentyl-C 1 -2 alkyl-, cyclohexyl-C 1 -2 alkyl-, pyridinyl-C 1-2 alkyl-, pyrimidinyl-C 1-2 alkyl-, azetidinyl-C 1-2 alkyl-, piperidinyl-C 1-2 alkyl-, pyrrolidinyl-C 1-2 alkyl-, and thiazolyl-C 1-2 alkyl- are each optionally substituted with 1, 2, or 3 substituents independently selected from C 1-3 alkyl, C 1-3 haloalkyl, halo, CN, OR a7 , and NR c7 R d7 ;
or any R c1 and R d1 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with NR c7 R d7 ;
each R a2 , R b2 , R c2 , and R d2 is independently selected from H, C 1-3 alkyl, C 1-3 haloalkyl, phenyl, cyclopropyl, cyclobutyl, cyclopropyl-C 1-2 alkyl-, cyclobutyl-C 1-2 alkyl-, pyridinyl, pyrimidinyl, isoxazolyl, azetidinyl, piperidinyl, and pyrrolidinyl, wherein said C 1-3 alkyl, C 1-3 haloalkyl, phenyl, cyclopropyl, cyclobutyl, cyclopropyl-C 1-2 alkyl-, cyclobutyl-C 1-2 alkyl-, pyridinyl, pyrimidinyl, isoxazolyl, azetidinyl, piperidinyl, and pyrrolidinyl are each optionally substituted with 1 or 2 substituents independently selected from C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, halo, CN, OR a7 , and NR c7 R d7 ;
each R a3 , R b3 , R c3 , and R d3 is independently selected from H, C 1-3 alkyl, C 1-3 haloalkyl, phenyl, cyclopropyl, cyclobutyl, cyclopropyl-C 1-2 alkyl-, cyclobutyl-C 1-2 alkyl-, pyridinyl, pyrimidinyl, isoxazolyl, azetidinyl, piperidinyl, and pyrrolidinyl, wherein said C 1-3 alkyl, C 1-3 haloalkyl, phenyl, cyclopropyl, cyclobutyl, cyclopropyl-C 1-2 alkyl-, cyclobutyl-C 1-2 alkyl-, pyridinyl, pyrimidinyl, isoxazolyl, azetidinyl, piperidinyl, and pyrrolidinyl are each optionally substituted with 1 or 2 substituents independently selected from C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, halo, CN, OR a7 , and NR c7 R d7 ;
each R a4 , R b4 , R c4 , and R d4 is independently selected from H and C 1-3 alkyl;
each R a5 , R b5 , R c5 , and R d5 is independently selected from H or C 1-3 alkyl;
each R a6 , R b6 , R c6 , and R d6 is independently selected from H or C 1-3 alkyl; and
each R a7 , R b7 , R c7 , and R d7 is independently selected from H or C 1-3 alkyl.
4. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring A is phenyl optionally substituted by 1, 2, 3, or 4 substituents independently selected from R A .
5. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring A is phenyl substituted by one R A .
6. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring A is phenyl substituted by CN.
7. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring B is phenyl, C 3-10 cycloalkyl, 4-10 membered heterocycloalkyl, or 5-6 membered heteroaryl, each optionally substituted by 1, 2, 3, or 4 substituents independently selected from R B .
8. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring B is phenyl or 5-6 membered heteroaryl, each optionally substituted by 1, 2, 3, or 4 substituents independently selected from R B .
9. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring B is phenyl, pyridyl, 3-oxo-3,4-dihydro-2H-1,4-benzoxazinyl, 2,3-dihydro-1,4-benzodioxinyl, pyrrolo[2,3-b]pyridinyl, pyrazolo[3,4-b]pyridinyl, 1,3-benzothiazolyl, 2-oxo-2,3-dihydro-1,3-benzoxazolyl, indazolyl, 2-oxo-2,3-dihydro[1,3]oxazolo[4,5-b]pyridinyl, 2,3-dihydro-1H-indenyl, 2-oxo-2,3-dihydro-1H-indolyl, quinoxalinyl, 2-oxo-1,2,3,4-tetrahydroquinolinyl, benzimidazolyl, 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazinyl, 2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridinyl, or pyrimidinyl, each optionally substituted by 1, 2, 3, or 4 substituents independently selected from R B .
10. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring B is phenyl, pyridyl, or pyrimidinyl, each optionally substituted by 1, 2, 3, or 4 substituents independently selected from R B .
11. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring B is phenyl, pyridyl, 3-oxo-3,4-dihydro-2H-1,4-benzoxazinyl, 2,3-dihydro-1,4-benzodioxinyl, pyrrolo[2,3-b]pyridinyl, pyrazolo[3,4-b]pyridinyl, 1,3-benzothiazolyl, 2-oxo-2,3-dihydro-1,3-benzoxazolyl, indazolyl, 2-oxo-2,3-dihydro[1,3]oxazolo[4,5-b]pyridinyl, 2,3-dihydro-1H-indenyl, 2-oxo-2,3-dihydro-1H-indolyl, quinoxalinyl, 2-oxo-1,2,3,4-tetrahydroquinolinyl, benzimidazolyl, 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazinyl, 2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridinyl, or pyrimidinyl, each optionally substituted by 1, 2, 3, or 4 substituents independently selected from Cy 3 , halo, C 1-6 alkyl, C 1-6 haloalkyl, OR a5 , CN, NR c5 C(O)OR a5 , and NR c5 R d5 .
12. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring B is phenyl, pyridyl, or pyrimidinyl, each optionally substituted by one substituent selected from Cy 3 , halo, C 1-6 alkyl, C 1-6 haloalkyl, OR a5 , and NR c5 R d5 .
13. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring B is phenyl, pyridyl, 3-oxo-3,4-dihydro-2H-1,4-benzoxazinyl, 2,3-dihydro-1,4-benzodioxinyl, pyrrolo[2,3-b]pyridinyl, pyrazolo[3,4-b]pyridinyl, 1,3-benzothiazolyl, 2-oxo-2,3-dihydro-1,3-benzoxazolyl, indazolyl, 2-oxo-2,3-dihydro[1,3]oxazolo[4,5-b]pyridinyl, 2,3-dihydro-1H-indenyl, 2-oxo-2,3-dihydro-1H-indolyl, quinoxalinyl, 2-oxo-1,2,3,4-tetrahydroquinolinyl, benzimidazolyl, 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazinyl, 2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridinyl, or pyrimidinyl, each optionally substituted by 1, 2, 3, or 4 substituents independently selected from chloro, methyl, trifluoromethyl, piperidinyl, methoxy, ethyl, 2-oxopyrrolidinyl, methyl(tetrahydrofuran-2-ylmethyl)amino, fluoro, 2-oxo-1,3-oxazolidinyl, amino, cyano, hydroxymethyl, (4-(methylsulfonyl)piperazin-1-yl)methyl, hydroxy, morpholin-4-ylmethyl, (CH 3 O)(C═O)N(CH 3 ), (CH 3 O)(C═O)N(CH 3 )-methyl, 1-hydroxyethyl, cyanomethyl, 3-methyl-2-oxoimidazolidinyl or dimethylamino.
14. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring B is phenyl, pyridyl, or pyrimidinyl, each optionally substituted by chloro, methyl, trifluoromethyl, piperidinyl, methoxy, or dimethylamino.
15. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring B is phenyl substituted by methyl.
16. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is C 1-6 alkyl, Cy 1 , OR a1 , SR a1 , C(O)NR c1 R d1 , NR c1 R d1 , NR c1 C(O)R b1 , or NR c1 C(O)NR c1 R d1 wherein said C 1-6 alkyl is optionally substituted with 1, 2, or 3 substituents independently selected from Cy 1 , halo, CN, OH, OR a1 , SR a1 , C(O)R b1 , C(O)NR c1 R d1 , C(O)OR a1 , OC(O)R b1 , OC(O)NR c1 R d1 , NR c1 R d1 , NR c1 C(O)R b1 , NR c1 C(O)OR a1 , NR c1 C(O)NR c1 R d1 , C(═NR e1 )R b1 , C(═NR e1 )NR c1 R d1 , NR c1 C(═NR e1 )NR c1 R d1 , NR c1 S(O)R b1 , NR c1 S(O) 2 R b1 , NR c1 S(O) 2 NR c1 R d1 , S(O)R b1 , S(O)NR c1 R d1 , S(O) 2 R b1 , and S(O) 2 NR c1 R d1 .
17. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is C 1-6 alkyl, Cy 1 , OR a1 , SR a1 , C(O)NR c1 R d1 , NR c1 R d1 , NR c1 C(O)R b1 , or NR c1 C(O)NR c1 R d1 , wherein said C 1-6 alkyl is optionally substituted with Cy 1 , OH, or OR a1 .
18. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is OR a1 .
19. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is C 1-6 alkyl substituted with 1 or 2 substituents independently selected from Cy 1 or OR a1 .
20. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is Cy 1 optionally substituted with 1 or 2 substituents independently selected from C 1-4 alkyl or NR c6 R d6 .
21. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is pyrrolidin-3-ylmethoxy, 2-pyrrolidin-3-ylethyl, [pyrrolidin-3-yloxy]methyl, [3-(dimethylamino)pyrrolidin-1-yl]methyl, [3-(dimethylamino)pyrrolidin-1-yl]ethyl, (1-methylpyrrolidin-3-yl)oxy, 3-(dimethylamino)propoxy, piperidin-3-ylmethoxy, [1, methylpyrrolidin-3-yl]methoxy, [1-methylpiperidin-3-yl]methoxy, [pyrrolidin-3-ylmethyl]thio, 4-(dimethylamino)piperidin-1-yl, 3-(dimethylamino)propyl](methyl)amino, [2-(1-methylpyrrolidin-2-yl)ethyl]amino, (1-methylpiperidin-4-yl)amino, 4-methyl-1,4-diazepan-1-yl, 2,7-diazaspiro[4.4]non-2-yl, 2,7-diazaspiro[3.5]non-7-yl, 3-(dimethylamino)-N-methylpyrrolidine, [2-(2-amino-1,3-thiazol-4-yl)ethyl]amino, azetidin-3-ylmethylaminocarbonyl, 3-(dimethylamino)piperidin-1-yl, [1-(2-hydroxyethyl)piperidin-3-yl]methoxy, [1-(2-cyanoethyl)piperidin-3-yl]methoxy, [1-ethylpiperidin-3-yl]methoxy, or 1-methylazetidin-3-ylaminocarbonyl.
22. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is pyrrolidin-3-ylmethoxy, 2-pyrrolidin-3-ylethyl, [pyrrolidin-3-yloxy]methyl, [3-(dimethylamino)pyrrolidin-1-yl]methyl, [3-(dimethylamino)pyrrolidin-1-yl]ethyl, (1-methylpyrrolidin-3-yl)oxy, 3-(dimethylamino)propoxy, piperidin-3-ylmethoxy, [1, methylpyrrolidin-3-yl]methoxy, [1-methylpiperidin-3-yl]methoxy, [pyrrolidin-3-ylmethyl]thio, 4-(dimethylamino)piperidin-1-yl, 3-(dimethylamino)propyl](methyl)amino, [2-(1-methylpyrrolidin-2-yl)ethyl]amino, (1-methylpiperidin-4-yl)amino, 4-methyl-1,4-diazepan-1-yl, 2,7-diazaspiro[4.4]non-2-yl, 2,7-diazaspiro[3.5]non-7-yl, 3-(dimethylamino)-N-methylpyrrolidine, [2-(2-amino-1,3-thiazol-4-yl)ethyl]amino, azetidin-3-ylmethylaminocarbonyl, or 1-methylazetidin-3-ylaminocarbonyl.
23. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein each R a1 is independently selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, and Cy 4 ; wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted with 1, 2, or 3 substituents independently selected from Cy 4 , halo, CN, OR a3 , SR a3 , C(O)R b3 , C(O)NR c3 R d3 , C(O)OR a3 , OC(O)R b3 , OC(O)NR c3 R d3 , NR c3 R d3 , NR c3 C(O)R b3 , NR c3 C(O)OR a3 , NR c3 C(O)NR c3 R d3 , C(═NR e3 )R b3 , C(═NR e3 )NR c3 R d3 , NR c3 C(═NR e3 )NR c3 R d3 , NR c3 S(O)R b3 , NR c3 S(O) 2 R b3 , NR c3 S(O) 2 NR c3 R d3 , S(O)R b3 , S(O)NR c3 R d3 , S(O) 2 R b3 , and S(O) 2 NR c3 R d3 .
24. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein each R a1 is C 1-6 alkyl optionally substituted with 1 or 2 substituents independently selected from Cy 4 and NR c3 R d3 .
25. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein each R a1 is C 1-3 alkyl optionally substituted with pyrrolidinyl, piperidinyl, or dimethylamino, wherein said pyrrolidinyl and piperidinyl are each optionally substituted with 1, 2, or 3 substituents independently selected from methyl, ethyl, cyanoethyl, and hydroxyethyl.
26. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 2 is H, C 1-6 alkyl, C 1-6 haloalkyl, Cy 2 , or C(O)NR c2 R d2 , wherein said C 1-6 alkyl is optionally substituted with 1, 2, or 3 substituents independently selected from Cy 2 , halo, CN, OR a2 , SR a2 , C(O)R b2 , C(O)NR c2 R d2 , C(O)OR a2 , OC(O)R b2 , OC(O)NR c2 R d2 , NR c2 R d2 , NR c2 C(O)R b2 , NR c2 C(O)OR a2 , NR c2 C(O)NR c2 R d2 , C(═NR e2 )R b2 , C(═NR e2 )NR c2 R d2 , NR c2 C(═NR e2 )NR c2 R d2 , NR c2 S(O)R b2 , NR c2 S(O) 2 R b2 , NR c2 S(O) 2 NR c2 R d2 , S(O)R b2 , S(O)NR c2 R d2 , S(O) 2 R b2 , and S(O) 2 NR c2 R d2 .
27. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 2 is H, C 1-6 alkyl, C 1-6 haloalkyl, Cy 2 , or C(O)NR c2 R d2 , wherein said C 1-6 alkyl is optionally substituted with 1 or 2 substituents independently selected from Cy 2 , CN, OR a2 , and NR c2 R d2 .
28. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 2 is H, methyl, trifluoromethyl, 4-methylphenyl, cyanomethyl, methylaminocarbonyl, dimethylaminocarbonyl, cyclopropylaminocarbonyl, 1-methylazetidin-3-ylaminocarbonyl, hydroxymethyl, azetidin-1-ylmethyl, cyclopropylmethylaminomethyl, (isoxazol-3-ylamino)methyl, dimethylaminomethyl, or dimethylaminoethyl.
29. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 2 is H.
30. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 3 is H.
31. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R A is CN.
32. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein each R B is independently selected from Cy 3 , halo, C 1-6 alkyl, C 1-6 haloalkyl, CN, NR c5 C(O)OR a5 NR c5 R d5 and OR a5 .
33. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein each R B is independently selected from Cy 3 , halo, C 1-6 alkyl, C 1-6 haloalkyl, and OR a5 .
34. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R B is C 1-6 alkyl.
35. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R B is methyl, chloro, trifluoromethyl, piperidinyl, methoxy, ethyl, 2-oxopyrrolidinyl, methyl(tetrahydrofuran-2-ylmethyl)amino, fluoro, 2-oxo-1,3-oxazolidinyl, amino, cyano, hydroxymethyl, (4-(methylsulfonyl)piperazin-1-yl)methyl, hydroxy, morpholin-4-ylmethyl, (CH 3 O)(C═O)N(CH 3 ), (CH 3 O)(C═O)N(CH 3 )-methyl, 1-hydroxyethyl, cyanomethyl, 3-methyl-2-oxoimidazolidinyl or dimethylamino.
36. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R B is methyl.
37. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein each Cy 1 is independently selected from 5-10 membered heteroaryl and 4-10 membered heterocycloalkyl, each of which is optionally substituted with 1, 2, 3, or 4 substituents independently selected from R Cy .
38. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein each Cy 1 is independently selected from 5-10 membered heteroaryl and 4-10 membered heterocycloalkyl, each of which is optionally substituted with 1 or 2 substituents independently selected from C 1-4 alkyl and NR c6 R d6 .
39. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Cy 1 is 4-10 membered heterocycloalkyl, each of which is optionally substituted with 1, 2, 3, or 4 substituents independently selected from R Cy .
40. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Cy 1 is azetidinyl, piperidinyl, pyrrolidinyl, diazapanyl, or diazaspirononanyl, each optionally substituted with 1 or 2 substituents independently selected from R Cy .
41. The compound of claim 1 , having Formula II:
or a pharmaceutically acceptable salt thereof, wherein n is 0, 1, 2, 3, or 4.
42. The compound of claim 41 , or a pharmaceutically acceptable salt thereof, wherein group:
is selected from any one of Formulae (B-1) to (B-15):
wherein any one of the groups of Formulae (B-1) to (B-15) is optionally substituted with 1, 2, 3, or 4 substituents independently selected from R B .
43. The compound of claim 1 , having Formula IIa:
or a pharmaceutically acceptable salt thereof.
44. The compound of claim 1 , having Formula III:
or a pharmaceutically acceptable salt thereof, wherein n is 0, 1, 2, 3, or 4 and wherein m is 0, 1, 2, 3, or 4.
45. The compound of claim 1 , having Formula IV:
or a pharmaceutically acceptable salt thereof, wherein m is 0, 1, 2, 3, or 4.
46. The compound of claim 1 , having Formula V:
or a pharmaceutically acceptable salt thereof.
47. The compound of claim 1 , having Formula VI:
or a pharmaceutically acceptable salt thereof.
48. The compound of claim 1 , having Formula VII:
or a pharmaceutically acceptable salt thereof.
49. The compound of claim 48 , or a pharmaceutically acceptable salt thereof, wherein group:
is selected from any one of Formulae (B-1a) to (B-15a):
wherein any one of the groups of Formulae (B-1a) to (B-15a) is optionally substituted with 1, 2, 3, or 4 substituents independently selected from R B .
50. The compound of claim 1 selected from:
4-{5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-[5-(4-methylphenyl)-8-(2-pyrrolidin-3-ylethyl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-(5-(4-methylphenyl)-8-{[(3R)-pyrrolidin-3-yloxy]methyl}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-[8-{[(3S)-3-(dimethylamino)pyrrolidin-1-yl]methyl}-5-(4-methylphenyl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-{[(3R)-3-(dimethylamino)pyrrolidin-1-yl]methyl}-5-(4-methylphenyl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-{2-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]ethyl}-5-(4-methylphenyl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-{5-(4-methylphenyl)-8-[(1-methylpyrrolidin-3-yl)oxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-[8-[3-(dimethylamino)propoxy]-5-(4-methylphenyl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-{5-(4-methylphenyl)-8-[(3R)-piperidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{5-(4-methylphenyl)-8-[(3S)-piperidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-(5-(4-methylphenyl)-8-{[(3R)-1-methylpyrrolidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-(4-methylphenyl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-(4-methylphenyl)-8-{[(3R)-pyrrolidin-3-ylmethyl]thio}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(4-methylphenyl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-[[3-(dimethylamino)propyl](methyl)amino]-5-(4-methylphenyl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-(5-(4-methylphenyl)-8-{[2-(1-methylpyrrolidin-2-yl)ethyl]amino}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-{5-(4-methylphenyl)-8-[(1-methylpiperidin-4-yl)amino]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-[8-(4-methyl-1,4-diazepan-1-yl)-5-(4-methylphenyl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-(2,7-diazaspiro[4.4]non-2-yl)-5-(4-methylphenyl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-(2,7-diazaspiro[3.5]non-7-yl)-5-(4-methylphenyl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
(3R)—N-[6-(4-cyanophenyl)-5-(4-methylphenyl)imidazo[1,2-a]pyrazin-8-yl]-3-(dimethylamino)-N-methylpyrrolidine-1-carboxamide;
(3S)—N-[6-(4-cyanophenyl)-5-(4-methylphenyl)imidazo[1,2-a]pyrazin-8-yl]-3-(dimethylamino)-N-methylpyrrolidine-1-carboxamide;
4-[8-{[2-(2-amino-1,3-thiazol-4-yl)ethyl]amino}-5-(4-methylphenyl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
N-(azetidin-3-ylmethyl)-6-(4-cyanophenyl)-5-(4-methylphenyl)imidazo[1,2-a]pyrazine-8-carboxamide;
6-(4-cyanophenyl)-N-(1-methylazetidin-3-yl)-5-(4-methylphenyl)imidazo[1,2-a]pyrazine-8-carboxamide;
4-{(5-phenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{5-(4-chlorophenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{8-[(3R)-pyrrolidin-3-ylmethoxy]-5-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{5-(4-piperidin-1-ylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{5-(4-methoxyphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{5-[2-(dimethylamino)pyrimidin-5-yl]-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-(5-[6-(dimethylamino)pyridin-3-yl]-8-{[(3R)-1-methylpyrrolidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-{2-methyl-5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-[5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]-2-(trifluoromethyl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-{2,5-bis(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{2-(cyanomethyl)-5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
6-(4-cyanophenyl)-N-methyl-5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo-[1,2-a]pyrazine-2-carboxamide;
6-(4-cyanophenyl)-N,N-dimethyl-5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazine-2-carboxamide;
6-(4-cyanophenyl)-N-cyclopropyl-5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazine-2-carboxamide;
6-(4-cyanophenyl)-N-(1-methylazetidin-3-yl)-5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazine-2-carboxamide;
4-{2-(hydroxymethyl)-5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{2-[(dimethylamino)methyl]-5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{2-(azetidin-1-ylmethyl)-5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{2-{[(cyclopropylmethyl)amino]methyl}-5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{2-[(isoxazol-3-ylamino)methyl]-5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-(2-[(dimethylamino)methyl]-5-(4-methylphenyl)-8-{[(3R)-1-methylpyrrolidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile; and
4-{2-[2-(dimethylamino)ethyl]-5-(4-methylphenyl)-8-[(3R)-pyrrolidin-3-ylmethoxy]imidazo[1,2-a]pyrazin-6-yl}benzonitrile,
or a pharmaceutically acceptable salt of any of the aforementioned.
51. The compound of claim 1 selected from:
4-{8-{[(3R)-1-methylpiperidin-3-yl]methoxy}-5-[6-(2-oxopyrrolidin-1-yl)pyridin-3-yl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-(5-(4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-(2,3-dihydro-1,4-benzodioxin-6-yl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-[6-(dimethylamino)pyridin-3-yl]-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(8-{[(3R)-1-methylpiperidin-3-yl]methoxy}-5-{6-[methyl(tetrahydrofuran-2-ylmethyl)amino]pyridin-3-yl}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-[8-{[(3R)-1-methylpiperidin-3-yl]methoxy}-5-(1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-{[(3R)-1-methylpiperidin-3-yl]methoxy}-5-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-(5-(1,3-benzothiazol-5-yl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-{8-{[(3S)-3-(dimethylamino)pyrrolidin-1-yl]methyl}-5-[6-(2-oxopyrrolidin-1-yl)pyridin-3-yl]imidazo[1,2-a]pyrazin-6-yl)}benzonitrile;
4-{8-[4-(dimethylamino)piperidin-1-yl]-5-[6-(2-oxopyrrolidin-1-yl)pyridin-3-yl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(3-methyl-2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-{[(3R)-1-ethylpiperidin-3-yl]methoxy}-5-(1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(5-fluoro-3-methyl-2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-{[(3R)-1-ethylpiperidin-3-yl]methoxy}-5-(3-methyl-2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-{[(3R)-1-(2-cyanoethyl)piperidin-3-yl]methoxy}-5-(3-methyl-2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-{[(3R)-1-(2-hydroxyethyl)piperidin-3-yl]methoxy}-5-(1-methyl-1H-indazol-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(3-methyl-2-oxo-2,3-dihydro[1,3]oxazolo[4,5-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-{8-[4-(dimethylamino)piperidin-1-yl]-5-[6-(2-oxo-1,3-oxazolidin-3-yl)pyridin-3-yl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{5-(3-amino-1-methyl-1H-indazol-5-yl)-8-[4-(dimethylamino)piperidin-1-yl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
5-(6-(4-cyanophenyl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-5-yl)-2-methylbenzonitrile;
4-(5-[3-(hydroxymethyl)-4-methylphenyl]-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-(4-methyl-3-{[4-(methylsulfonyl)piperazin-1-yl]methyl}phenyl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-[4-(hydroxymethyl)-3-methylphenyl]-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-(3-hydroxy-2,3-dihydro-1H-inden-5-yl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-[4-(hydroxymethyl)phenyl]-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-{8-{[(3R)-1-methylpiperidin-3-yl]methoxy}-5-[4-(morpholin-4-ylmethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
methyl [5-(6-(4-cyanophenyl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-5-yl)-2-methylphenyl]methylcarbamate;
methyl [4-(6-(4-cyanophenyl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-5-yl)phenyl]methylcarbamate;
4-(5-(2-hydroxy-2,3-dihydro-1H-inden-5-yl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-(7-fluoro-3-hydroxy-2,3-dihydro-1H-inden-5-yl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-(1-hydroxy-2,3-dihydro-1H-inden-5-yl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-[3-fluoro-4-(hydroxymethyl)-5-methylphenyl]-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-[3,5-difluoro-4-(hydroxymethyl)phenyl]-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-(5-fluoro-6-methoxypyridin-3-yl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
methyl [4-(6-(4-cyanophenyl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-5-yl)-2-fluorobenzyl]methylcarbamate;
4-(5-[4-(1-hydroxyethyl)-3-methylphenyl]-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-[3-(1-hydroxyethyl)-4-methylphenyl]-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-(7-fluoro-1-hydroxy-2,3-dihydro-1H-inden-5-yl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-[2-fluoro-4-(morpholin-4-ylmethyl)phenyl]-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-[2-(hydroxymethyl)-4-methylphenyl]-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(5-[3-(cyanomethyl)-4-methylphenyl]-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(5,6-dimethylpyridin-3-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(2-hydroxy-2,3-dihydro-1H-inden-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(5-hydroxy-6-methylpyridin-3-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(3-hydroxy-2,3-dihydro-1H-inden-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-{8-[4-(dimethylamino)piperidin-1-yl]-5-[3-(hydroxymethyl)-4-methylphenyl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{8-[4-(dimethylamino)piperidin-1-yl]-5-[3-fluoro-4-(hydroxymethyl)-5-methylphenyl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(1-methyl-2-oxo-2,3-dihydro-1H-indol-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-{8-[3-(dimethylamino)piperidin-1-yl]-5-[6-(2-oxopyrrolidin-1-yl)pyridin-3-yl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{8-[4-(dimethylamino)piperidin-1-yl]-5-[6-(3-methyl-2-oxoimidazolidin-1-yl)pyridin-3-yl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{8-[4-(dimethylamino)piperidin-1-yl]-5-quinoxalin-6-ylimidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-{8-[4-(dimethylamino)piperidin-1-yl]-5-[2-(hydroxymethyl)-1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{8-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-[6-(2-oxopyrrolidin-1-yl)pyridin-3-yl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(3-ethyl-2-oxo-2,3-dihydro[1,3]oxazolo[4, 5-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(1-methyl-1H-benzimidazol-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(4-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-{8-[4-(dimethylamino)piperidin-1-yl]-5-[6-(4-methyl-3-oxopiperazin-1-yl)pyridin-3-yl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-{8-[4-(dimethylamino)piperidin-1-yl]-5-[3-(hydroxymethyl)-1-methyl-1H-indazol-5-yl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(1-methyl-2-oxo-2,3-dihydro-1H-pyrrolo [2,3-b]pyridin-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-(8-[4-(dimethylamino)piperidin-1-yl]-5-{2-[(1R)-1-hydroxyethyl]-1-methyl-1H-benzimidazol-5-yl}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-(8-[4-(dimethylamino)piperidin-1-yl]-5-{2-[(1S)-1-hydroxyethyl]-1-methyl-1H-benzimidazol-5-yl}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(1,2-dimethyl-1H-benzimidazol-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(5-methoxy-6-methylpyridin-3-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile;
5-(6-(4-cyanophenyl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy)}imidazo[1,2-a]pyrazin-5-yl)-2-methylnicotinonitrile;
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(5-hydroxy-6-methoxypyridin-3-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile; and
4-(5-(5-hydroxy-6-methoxypyridin-3-yl)-8-{[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile;
or a pharmaceutically acceptable salt thereof.
52. A pharmaceutical composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier or excipient.
53. A method of inhibiting lysine specific demethylase-1 comprising contacting a compound of claim 1 , or a pharmaceutically acceptable salt thereof, with said lysine specific demethylase-1.