6-substituted aminopyrazino[2′,1′:2,3]imidazo[4,5-c][1,7]naphthyridine compounds as CK2 inhibitors
AssigneeKing Faisal University
InventorsMichelyne Haroun, Christophe Tratrat
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Abstract
Novel 6-substituted aminopyrazino[2′,1′:2,3]imidazo[4,5-c][1,7]naphthyridine compounds, a method of synthesizing said compounds, a pharmaceutical composition comprising said compounds and a suitable carrier, and a method of using the compounds. The 6-substituted aminopyrazino[2′,1′:2,3]imidazo[4,5-c][1,7]naphthyridine compounds, identified as CK2 inhibitors, are useful as anticancer and/or antitumor agents, and as agents for treating other kinase-associated conditions including inflammation, pain, and certain immunological disorders, and other types of diseases such as diabetes, viral infection, neurodegenerative diseases.
Claims17
A compound having the formula I:
- 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, and —SO2CH2CH2CH2NR3R4;
- Ar is optionally substituted and is an aryl ring or a 5 or 6 membered heteroaryl ring, wherein either of the aryl ring or the heteroaryl ring is optionally substituted with one or more substituents selected from the group consisting of halogen, cyano, hydroxy, —OR1, —NH2, —NHR1, —NR1R2, —CONH2, —CONHR1, —CONR1R2, —SO2NH2, —SO2NHR1, —SO2NR1R2, —NHCOR1, —NHCO2R1, —NHCONHR1, —NHSO2NHR1, —NHSO2R1, —COR1, —CO2R1, a C1-C6 straight chain alkyl, a C1-C6 branched alkyl, a C3-C6 cycloalkyl, a halo-C1-C6 straight chain alkyl, a halo-C1-C6 branched alkyl, a halo-C3-C6 cycloalkyl, a cyano-C1-C6 straight chain alkyl, a cyano-C1-C6 branched chain alkyl, and a cyano-C3-C6 cycloalkyl;
- R1 and R2 are each independently selected from the group consisting of hydrogen, a C1-C6 straight chain alkyl, a C1-C6 branched alkyl, a C3-C6 cycloalkyl, a halo-C1-C6 straight chain alkyl, a halo-C1-C6 branched alkyl, a halo-C3-C6 cycloalkyl, a cyano-C1-C6 straight chain alkyl, a cyano-C1-C6 branched alkyl, and a cyano-C3-C6 cycloalkyl;
- and
- R3 and R4 are each independently selected from the group consisting of hydrogen, a C1-C6 straight chain alkyl, a C1-C6 branched alkyl, a C3-C6 cycloalkyl, a halo-C1-C6 straight chain alkyl, a halo-C1-C6 branched alkyl, a halo-C3-C6 cycloalkyl, a cyano-C1-C6 straight chain alkyl, a cyano-C1-C6 branched alkyl, and a cyano-C3-C6 cycloalkyl, or wherein R3 and R4, 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-C6 alkyl group, a halogen atom, a straight or branched C1-C6 alkoxy group, a straight or branched C1-C6 trihaloalkyl group, and a hydroxy group.
A compound having the formula I:
- or a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof, wherein:
- R is phenyl substituted with one or more substituents independently selected from the group consisting of —NR1R2, a straight or branched C1-C6 alkyl, —CONR1R2, halogen, hydroxy, and —OR1, wherein R1 and R2 are independently a straight chain C1-C6 alkyl group;
- a —CH2CH2CH2NR3R4 group, wherein R3 and R4 are independently a straight chain C1-C6 alkyl group;
- a —CH2phenyl group substituted with a chlorine;
- a pyridin-3-ylmethyl group;
- or a 2-methylpyridin-4-yl group.
Dependencies are inferred from the claim text.