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US 12,215,107 B1Granted
Pyrazino[1′,2′:1,5]pyrazolo[4,3-c] [2,6] naphthyridine compounds as CK2 inhibitors
AssigneeKing Faisal University
InventorsChristophe Tratrat, Michelyne Haroun
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Abstract
Novel pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]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 pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]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.
Claims20
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, —SO2CH2CH2CH2NR3R4, 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;
- 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 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.
3 more elements
A compound having the formula I:
- or a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof, wherein:
- R is a -phenyl substituted with one or more substituents independently selected from the group consisting of —NR1R2, —OH, —NHCOR1, a straight or branched C1-C6 alkyl, —CONHR1, a halogen, —SO2NHR1, and —OR1;
- a —CH2CH2CH2NR1R2 group;
- a pyridyl group substituted with a methyl;
- a —CH2phenyl group substituted with a chlorine;
- and a —CH2pyridyl;
- and
- R1 and R2 are independently a straight chain C1-C6 alkyl group.
5 more elements
A compound selected from the group consisting of:
- N-(3-chlorophenyl)pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-amine (1);
- N-(m-tolyl)pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-amine (2);
- N,N-dimethyl-3-(pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-ylamino)benzamide (3);
- N1,N1-dimethyl-N3-(pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-yl)benzene-1,3-diamine (4);
- N-(3-methoxyphenyl)pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-amine (5);
- 3-(pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-6-ylamino) phenol (6);
- N-(3-isopropylphenyl)pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-amine (7);
- N-(3-(pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-ylamino)phenyl) acetamide (8);
- N-methyl-3-(pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-ylamino)benzenesulfonamide (9);
- N-(4-methoxyphenyl)pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-amine (10);
- N-(p-tolyl)pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-amine (11);
- N1,N1-dimethyl-N4-(pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-yl)benzene-1,4-diamine (12);
- N-(2-methylpyridin-4-yl)pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-amine (13);
- N-(3-chlorobenzyl)-10aH-pyrido[3′,4′:4,5]pyrrolo[3,2-c][2,6]naphthyridin-5-amine (14);
- N-(pyridin-3-ylmethyl)pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-amine (15);
- N1,N1-dimethyl-N3-(pyrazino[1′,2′:1,5]pyrazolo[4,3-c][2,6]naphthyridin-5-yl) propane-1,3-diamine (16);
- and
- a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof.
15 more elements
Dependencies are inferred from the claim text.