US 12,122,775 B1
Substituted pyrido[4,3-e]pyrrolo[1,2-a]pyrazines as CK2 inhibitors
Michelyne Haroun, Al-Ahsa (SA); and Christophe Tratrat, Al-Ahsa (SA)
Assigned to KING FAISAL UNIVERSITY, Al-Ahsa (SA)
Filed by KING FAISAL UNIVERSITY, Al-Ahsa (SA)
Filed on Jan. 16, 2024, as Appl. No. 18/413,246.
Int. Cl. A61K 31/4985 (2006.01); A61P 35/00 (2006.01); C07D 471/14 (2006.01); C07D 487/04 (2006.01)
CPC C07D 471/14 (2013.01) [A61K 31/4985 (2013.01); A61P 35/00 (2018.01)] 20 Claims
 
1. A compound having the formula I:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt or stereoisomer thereof,
wherein:
R is C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, (CH2)2-3NR3R4, (CH2)1-2Ar, C(O)—(CH2)2-3NR3R4, C(O)Ar, S(O)2—(CH2)2-3NR3R4, S(O)2Ar, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cyanocycloalkyl, or Ar;
Ar is aryl or 5- or 6-membered heteroaryl, wherein the aryl or 5- or 6-membered heteroaryl is optionally substituted with one, two, or three substituents independently selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C(O)R1, C(O)NR1R2, C(O)OR1, NR1R2, NHC(O)R1, NHC(O)NHR1, NHC(O)OR1, NHS(O)2R1, NHS(O)2NHR1, OR1, S(O)2NR1R2, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, and C3-C6 cyanocycloalkyl;
each R1 is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, or C3-C6 cyanocycloalkyl;
each R2 is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, or C3-C6 cyanocycloalkyl;
each R3 is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, or C3-C6 cyanocycloalkyl; and
each R4 is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, or C3-C6 cyanocycloalkyl; or
any R3 and R4, taken together with the nitrogen atom to which they are attached, independently forms a nitrogen-containing heterocyclyl, wherein each nitrogen-containing heterocyclyl is optionally and independently substituted with one, two, or three substituents independently selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 trihaloalkyl, OH, and OC1-C6 alkyl.