US 12,269,827 B1
Substituted pyrazino[1′,2′:1,5]pyrazolo[4,3-c][1,6]naphthyridines as CK2 inhibitors
Christophe Tratrat, Al-Ahsa (SA); and Michelyne Haroun, Al-Ahsa (SA)
Assigned to KING FAISAL UNIVERSITY, Al-Ahsa (SA)
Filed by KING FAISAL UNIVERSITY, Al-Ahsa (SA)
Filed on Dec. 19, 2023, as Appl. No. 18/545,059.
Int. Cl. A61K 31/4985 (2006.01); A61P 35/00 (2006.01); A61P 35/02 (2006.01); C07D 471/22 (2006.01); C07D 487/22 (2006.01)
CPC C07D 471/22 (2013.01) [A61K 31/4985 (2013.01); A61P 35/00 (2018.01); A61P 35/02 (2018.01)] 11 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)2-3NR1R2, (CH2)1-2Ar, C(O)—(CH2)2-3NR1R2, C(O)Ar, S(O)2—(CH2)2-3NR1R2, 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; and
each R2 is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, or C3-C6 cyanocycloalkyl.
 
11. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof.