US 11,981,676 B1
Pyrazolo[4,3-c][2,6]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 Jan. 16, 2024, as Appl. No. 18/414,429.
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 471/14 (2006.01); A61K 31/4375 (2006.01); A61P 35/00 (2006.01)
CPC C07D 471/14 (2013.01) [A61K 31/4375 (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 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-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; 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, or wherein R3 and R4, taken together with a nitrogen atom to which they are attached, form a nitrogen-containing heterocycle, such nitrogen-containing heterocycle being optionally substituted with from one to three substituents independently selected from the group consisting of a straight or branched C1-C6alkyl group, a halogen atom, a straight or branched C1-C6 alkoxy group, a straight or branched C1-C6 trihaloalkyl group, and a hydroxy group.