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US 11,952,378 B1Granted
Pyrrolo[2,3-c]isoquinoline-1,2-dione compounds as CK2 inhibitors
AssigneeKing Faisal University
InventorsChristophe Tratrat, Michelyne Haroun
Life of this patent
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Abstract
Novel pyrrolo[2,3-c]isoquinoline-1,2-dione, a method of synthesizing said compounds, a pharmaceutical composition comprising said compounds and a suitable carrier, and a method of using the compounds. The pyrrolo[2,3-c]isoquinoline-1,2-dione 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.
Claims18
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, —COCH2Ar, —CH2CH2NHR1, —CH2CH2NR1R2, —CH2CH2CH2NHR1, —CH2CH2CH2NR1R2, —COCH2NHR1, —COCH2NR1R2, —COCH2CH2NHR1, and —COCH2CH2NR1R2;
- 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, —CF3, —OH, —OR1, —NH2, —NHR1, —NR1R2, —CONH2, —CONHR1, —CONR1R2, —SO2NH2, —SO2NHR1, —SO2NR1R2, —NHCOR1, —NHCO2R1, —NHCONHR1, —NHSO2NHR1, —NHSO2R1, —NHCH2COR1, —NHCH2CO2R1, —NHCH2CONHR1, —COR1, —CO2R1, —OCH2CO2R1, —OCH2COR1, —OCH2CONHR1, —OCH2CONR1R2, 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
- 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, or wherein R1 and R2, 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-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.
2 more elements
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, —CF3, —NHCOR1, a straight or branched C1-C6 alkyl, —CONR1R2, halogen, —SO2NR1R2, and —OR1;
- a —CH2CH2NR1R2 group;
- a pyridyl group substituted with a methyl, and a —CH2phenyl group substituted with a chlorine;
- and
- R1 and R2 are independently a straight chain C1-C6 alkyl group or wherein R1 and R2 are taken together with the nitrogen atom to which they are attached to form a nitrogen-containing heterocycle, such nitrogen-containing heterocycle being optionally substituted with a straight or branched C1-C6 alkyl group.
3 more elements
A compound selected from the group consisting of:
- 5-((3-chlorophenyl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (1);
- 1,2-dioxo-5-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (2);
- 5-((3-methoxyphenyl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (3);
- 1,2-dioxo-5-((3-(trifluoromethyl)phenyl)amino)-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (4);
- 5-((3-(dimethylamino)phenyl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (5);
- 5-((3-isopropylphenyl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (6);
- 5-((3-(dimethylcarbamoyl)phenyl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (7);
- 5-((3-(N-methylsulfamoyl)phenyl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (8);
- 5-((3-acetamidophenyl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (9);
- 5-((4-chlorophenyl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (10);
- 5-((4-methoxyphenyl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (11);
- 5-((4-(dimethylamino)phenyl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (12);
- 5-((2-methylpyridin-4-yl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (13);
- 5-((3-chlorobenzyl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (14);
- 5-((2-(dimethylamino)ethyl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (15);
- 5-((2-(4-methylpiperazin-1-yl)ethyl)amino)-1,2-dioxo-2,3-dihydro-1H-pyrrolo[2,3-c]isoquinoline-7-carboxylic acid (16);
- and
- a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof.
15 more elements
Dependencies are inferred from the claim text.