US 12,134,617 B1
Pyrimido[1′6′:1,5]pyrazolo[4,3-c][1,7]naphthyridines 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. 10, 2024, as Appl. No. 18/409,768.
Int. Cl. C07D 471/22 (2006.01); A61K 31/519 (2006.01); A61P 35/00 (2006.01)
CPC C07D 471/22 (2013.01) [A61K 31/519 (2013.01); A61P 35/00 (2018.01)] 16 Claims
 
1. A compound having the formula I:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof, wherein:
R is selected from the group consisting of —Ar, —CH2Ar, —CH2CH2Ar, —COAr, —SO2Ar, —CH2CH2NHR3, —CH2CH2NR3R4, —CH2CH2CH2NHR3, —CH2CH2CH2NR3R4, —COCH2CH2NHR3, —COCH2CH2NR3R4, —COCH2CH2CH2NHR3, —COCH2CH2CH2NR3R4, —SO2CH2CH2NHR3, —SO2CH2CH2NR3R4, —SO2CH2CH2CH2NHR3, —SO2CH2CH2CH2NR3R4, C1-C6 alkyl, C1-C6 branched alkyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C1-C6 branched alkyl, halo-C3-C6 cycloalkyl, cyano-C1-C6 alkyl, cyano-C1-C6 branched alkyl, and cyano-C3-C6 cycloalkyl;
Ar is an aryl ring or a 5 or 6 membered heteroaryl ring, either of the aryl ring or the heteroaryl ring being optionally substituted with one or more substituents selected from the group consisting of halogen, cyano, —OH, —OR1, —NH2, —NHR1, —NR1R2, —CONH2, —CONHR1, —CONR1R2, —SO2NH2, —SO2NHR1, —SO2NR1R2, —NHCOR1, —NHCO2R1, —NHCONHR1, —NHSO2NHR1, —NHSO2R1, —COR1, —CO2R1, C1-C6 straight chained alkyl, C1-C6 branched alkyl, C3-C6 cycloalkyl, halo-C1-C6 straight chain alkyl, halo-C1-C6 branched alkyl, halo-C3-C6 cycloalkyl, cyano-C1-C6 straight chain alkyl, cyano-C1-C6 branched alkyl, and cyano-C3-C6 cycloalkyl;
R1 and R2 are each independently selected from the group consisting of hydrogen, C1-C6straight chained alkyl, C1-C6 branched alkyl, C3-C6 cycloalkyl, halo-C1-C6 straight chain alkyl, halo-C1-C6 branched alkyl, halo-C3-C6 cycloalkyl, cyano-C1-C6 straight chain alkyl, cyano-C1-C6 branched alkyl, and cyano-C3-C6 cycloalkyl; and
R3 and R4 are each independently selected from hydrogen, C1-C6 alkyl, C1-C6 branched alkyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C1-C6 branched alkyl, halo-C3-C6 cycloalkyl, cyano-C1-C6 alkyl, cyano-C1-C6 branched alkyl, and a cyano-C3-C6 cycloalkyl.