US 12,071,437 B1
Pyrazolo[1,5-a]pyrido[4,3-e]pyrimidine-2-carboxylic acids 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. 12, 2024, as Appl. No. 18/411,323.
Int. Cl. C07D 471/14 (2006.01); A61K 31/519 (2006.01); A61P 35/00 (2006.01)
CPC C07D 471/14 (2013.01) [A61K 31/519 (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, 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, —SOCH2CH2CH2NHR3, —SO2CH2CH2CH2NR3R4, C1-C6 straight chain alkyl, C3-C6 branched alkyl, C3-C6 cycloalkyl, halo-C1-C6 straight chain alkyl, halo-C3-C6 branched alkyl, halo-C3-C6 cycloalkyl, cyano-C1-C6 straight chain alkyl, cyano-C3-C6 branched alkyl, and cyano-C3-C6 cycloalkyl;
Ar is an aryl ring or a 5 or 6 membered heteroaryl ring, wherein 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 chain alkyl, C3-C6 branched alkyl, C3-C6 cycloalkyl, halo-C1-C6 straight chain alkyl, halo-C3-C6 branched alkyl, halo-C3-C6 cycloalkyl, cyano-C1-C6 straight chain alkyl, cyano-C3-C6 branched alkyl, and cyano-C3-C6 cycloalkyl;
R1 and R2 are each independently selected from the group consisting of hydrogen, C1-C6 straight chain alkyl, C3-C6 branched alkyl, C3-C6 cycloalkyl, halo-C1-C6 straight chain alkyl, halo-C3-C6 branched alkyl, halo-C3-C6 cycloalkyl, cyano-C1-C6 straight chain alkyl, cyano-C3-C6 branched alkyl, and cyano-C3-C6 cycloalkyl; and
R3 and R4 are each independently selected from hydrogen, C1-C6 straight chain alkyl, C3-C6 branched alkyl, C3-C6 cycloalkyl, halo-C1-C6 straight chain alkyl, halo-C3-C6 branched alkyl, halo-C3-C6 cycloalkyl, cyano-C1-C6 straight chain alkyl, cyano-C3-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 C1-C6 alkyl group, a branched C3-C6 alkyl group, a halogen atom, a straight C1-C6 alkoxy group, a branched C3-C6 alkoxy group, a straight C1-C6 trihaloalkyl group, a branched C3-C6 trihaloalkyl group, and a hydroxy group.