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US 6,307,056 B1Granted
4-aryloxindoles
AssigneeHoffman-La Roche Inc.
InventorsWendy Lea Corbett, Kin-Chun Luk, Paige E. Mahaney
Life of this patent
Estimating the term…
Abstract
Disclosed are 4-aryloxindoles that inhibit or modulate protein kinases, in particular JNK protein kinases. These compounds and their pharmaceutically acceptable salts, and prodrugs of said compounds, are useful as anti-inflammatory agents, particularly useful in the treatment of rheumatoid arthritis. Also disclosed are pharmaceutical compositions containing the foregoing compounds, as well as methods for the treatment and/or control of inflammation, particularly in the treatment or control of rheumatoid arthritis, using said compounds.
Claims41
A compound of formula
- or prodrugs or pharmaceutically active metabolites of compounds of formula I, or the pharmaceutically acceptable salts of the foregoing compounds, wherein;
- A is selected from the group consisting of aryl or heteroaryl, each of which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of
- —H,
- —OR4,
- —COR4,
- —COOR4,
- —CONR6R7,
- —NR6R7,
- —CN,
- —NO2,
- —SO2R4,
- —SO2NR6R7,
- —halogen,
- —perfluoroalkyl,
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR4, —NR6R7, —COR4, —COOR4, —OCOR4, —CONR6R7, —CN, —NO2, —SO2R4, —SO2NR6R7, halogen, cycloalkyl, and heterocycle,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR4, —NR6R7, —COR4, —COOR4, —OCOR4, —CONR6R7, —CN, —NO2, —SO2R4, —SO2NR6R7, halogen, lower alkyl, and heterocycle, and
- heterocycle which is unsubstituted or substituted by the group consisting of —OR4, —NR6R7, —COR4, —COOR4, —OCOR4, —CONR6R7, —CN, —NO2, —SO2R4, —SO2NR6R7, halogen, lower alkyl, and cycloalkyl;
- R2 is selected from the group consisting of
- —H,
- —OR4,
- —COOR4,
- —CONR6R7,
- —NR6R7,
- halogen,
- —NO2,
- —CN,
- —SO2NR6R7,
- —SO2R4
- perfluoroalkyl, and
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR8, —NR6R7, —COR4, —COOR4, and —CONR6R7;
- R3 is selected from the group consisting of
- —H,
- —OR4,
- —COR4,
- —COOR4,
- —CONR6R7,
- halogen,
- —CN,
- —NR6R7,
- perfluoroalkyl, and
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR8 and —NR6R7;
- R4 is selected from the group consisting of
- —H,
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR6R7, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR6R7, lower alkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9, and
- heterocycle which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR6R7, lower alkyl, cycloalkyl, —CN, —NO2, —SO2R8, and —SO2NR8R9;
- R5 is selected from the group consisting of
- —H,
- —COR8,
- —CONR8R9, and
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR9, —NR9R10, —N(COR9)R10, —COR9, —CONR9R10, and —COOR9;
- R6 and R7 are each independently selected from the group consisting of
- —H,
- —COR8,
- —COOR8,
- —CONR8R9,
- —SO2R8,
- —SO2NR8R9,
- lower alkyl which is unsubstituted or substituted by the group consisting of
- —OR5,
- —COOR8,
- —COR8,
- —CONR8R9,
- —CN,
- —NO2,
- —SO2R8,
- —SO2NR8R9,
- —NR8R9,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- heterocycle which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- aryl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, -NR8R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9, and
- heteroaryl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- heterocycle which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- aryl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- heteroaryl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9, and
- —NR6R7 can form a ring having 3 to 7 atoms, said ring not including any additional hetero atoms or including one or more additional hetero atoms and being unsubstituted or substituted by the group consisting of one or more of lower alkyl, —OR5, —COR8, —COOR8, CONR8R9, and —NR5R9;
- R8 is selected from the group consisting of
- —H,
- lower alkyl which is unsubstituted or substituted by the group consisting of cycloalkyl, heterocycle, aryl, heteroaryl, —OR9, —NR9R10, and —N(COR9)R10,
- aryl which is unsubstituted or substituted by the group consisting of —OR9, —COOR9, —COR9, —CONR10R9, —NR10R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R9, halogen, —SO2F and —SO2NR10R9,
- heteroaryl which is unsubstituted or substituted by the group consisting of —OR9, —COOR9, —COR9, —CONR10R9, —NR10R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R9, halogen, —SO2F and —SO2NR10R9,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR9, —COOR9, —COR9, —CONR10R9, —NR10R9, lower alkyl, heterocycle, aryl, —CN, —NO2, —SO2R9, and —SO2NR10R9, and
- heterocycle which is unsubstituted or substituted by the group consisting of —OR9, —COOR9, —COR9, —CONR10R9, —NR10R9, lower alkyl, cycloalkyl, aryl, —CN, —NO2, —SO2R9, and —SO2NR10R9;
- R9 and R10 are each independently selected from the group consisting of —H, lower alkyl and aryl;
- and
- X is selected from the group consisting of ═N— and
84 more elements
A compound having the formula
- or the pharmaceutically acceptable salts of the foregoing compound, wherein;
- A is selected from the group consisting of aryl or heteroaryl, each of which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of
- —H,
- —OR4,
- —COR4,
- —COOR4,
- —CONR6R7,
- —NR6R7,
- —CN,
- —NO2,
- —SO2R4,
- —SO2NR6R7,
- —halogen,
- —perfluoroalkyl,
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR4, —NR6R7, —COR4, —COOR4, —OCOR4, —CONR6R7, —CN, —NO2, —SO2R4, —SO2NR6R7, halogen, cycloalkyl, and heterocycle,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR4, —NR6R7, COR4, —COOR4, —OCOR4, —CONR6R7, —CN, —NO2, —SO2R4, —SO2NR6R7, halogen, lower alkyl, and heterocycle, and
- heterocycle which is unsubstituted or substituted by the group consisting of —OR4, and —NR6R7, —COR4, —COOR4, —OCOR4, —CONR6R7, —CN, —NO2, —SO2R4, —SO2NR6R7, halogen, lower alkyl, and cycloalkyl;
- R2 is selected from the group consisting of
- —H,
- —OR4,
- —COOR4,
- —CONR6R7,
- —NR6R7,
- halogen,
- —NO2,
- —CN,
- —SO2NR6R7,
- —SO2R4
- perfluoroalkyl, and
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR8, —NR6R7, —COR4, —COOR4, and —CONR8R7;
- R3 is selected from the group consisting of
- —H,
- —OR4,
- —COR4,
- —COOR4,
- —CONR6R7,
- halogen,
- —CN,
- —NR6R7,
- perfluoroalkyl, and
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR8 and —NR6R7;
- R4 is selected from the group consisting of
- —H,
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR6R7, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR6R7, lower alkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9, and
- heterocycle which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR6R7, lower alkyl, cycloalkyl, —CN, —NO2, —SO2R8, and —SO2NR8R9;
- R5 is selected from the group consisting of
- —H,
- —COR8,
- —CONR8R9, and
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR9, —NR9R10, —N(COR9)R10, —COR9, —CONR9R10, and —COOR9;
- R6 and R7 are each independently selected from the group consisting of
- —H,
- —COR8,
- —COOR8,
- —CONR8R9,
- —SO2R8,
- —SO2NR8R9,
- lower alkyl which is unsubstituted or substituted by the group consisting of
- —OR5,
- —COOR8,
- —COR8,
- —CONR8R9,
- —CN,
- —NO2,
- —SO2R8,
- —SO2NR8R9,
- —NR8R9,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, heterocycle, —CN, —NO2, —SO2R8, and—SO2NR8R9,
- heterocycle which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- aryl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9, and
- heteroaryl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- heterocycle which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- aryl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- heteroaryl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9, and
- —NR6R7 can form a ring having 3 to 7 atoms, said ring not including any additional hetero atoms or including one or more additional hetero atoms and being unsubstituted or substituted by the group consisting of one or more of lower alkyl, —OR5, —COR8, —COOR8, CONR8R9, and —NR5R9;
- R8 is selected from the group consisting of
- —H,
- lower alkyl which is unsubstituted or substituted by the group consisting of cycloalkyl, heterocycle, aryl, heteroaryl, —OR9, —NR9R10, and —N(COR9)R10,
- aryl which is unsubstituted or substituted by the group consisting of —OR9, —COOR9, —COR9, —CONR10R9, —NR10R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R9, halogen, —SO2F and —SO2NR10R9,
- heteroaryl which is unsubstituted or substituted by the group consisting of —OR9, —COOR9, —COR9, —CONR10R9, —NR10R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R9, halogen, —SO2F and —SO2NR10R9,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR9, —COOR9, —COR9, —CONR10R9, —NR10R9, lower alkyl, heterocycle, aryl, —CN, —NO2, —SO2R9, and —SO2NR10R9, and
- heterocycle which is unsubstituted or substituted by the group consisting of —OR9, —COOR9, —COR9, —CONR10R9, —NR10R9, lower alkyl, cycloalkyl, aryl, —CN, —NO2, —SO2R9, and —SO2NR10R9;
- R9 and R10 are each independently selected from the group consisting of —H, lower alkyl and aryl;
- and
- X is selected from the group consisting of ═N— and
84 more elements
A compound of formula
- or the pharmaceutically acceptable salts of the foregoing compounds, wherein;
- R1, R1′ and R1″ are each independently selected from the group consisting of
- —H,
- —OR4,
- —COR4,
- —COOR4,
- —CONR6R7,
- —NR6R7,
- halogen,
- —SO2R4,
- —SO2NR6R7,
- —NO2,
- —CN,
- perfluoroalkyl,
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR4, —NR6R7, —COR4, —COOR4, —OCOR4, —CONR6R7, —CN, —NO2, —SO2R4, —SO2NR6R7, halogen, cycloalkyl, and heterocycle,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR4 and —NR6R7, —COR4, —COOR4, —OCOR4, —CONR6R7, —CN, —NO2, —SO2R4, —SO2NR6R7, halogen, lower alkyl, and heterocycle, and
- heterocycle which is unsubstituted or substituted by the group consisting of —OR4 and —NR6R7, —COR4, —COOR4, —OCOR4, —CONR6R7, —CN, —NO2, —SO2R4, —SO2NR6R7, halogen, lower alkyl, and cycloalkyl;
- R2 is selected from the group consisting of
- —H,
- —OR4,
- —COOR4,
- —CONR6R7,
- —NR6R7,
- halogen,
- —NO2,
- —CN,
- —SO2NR6R7,
- —SO2R4
- perfluoroalkyl, and
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR8, —NR6R7, —COR4, —COOR4, and —CONR6R7;
- R3 is selected from the group consisting of
- —H,
- —OR4,
- —COR4,
- —COOR4,
- —CONR6R7,
- halogen,
- —CN,
- —NR6R7,
- perfluoroalkyl, and
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR8 and —NR6R7;
- R4 is selected from the group consisting of
- —H,
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR6R7, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR6R7, lower alkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9, and
- heterocycle which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR6R7, lower alkyl, cycloalkyl, —CN, —NO2, —SO2R8, and —SO2NR8R9;
- R5 is selected from the group consisting of
- —H,
- —COR8,
- —CONR8R9, and
- lower alkyl which is unsubstituted or substituted by the group consisting of —OR9, —NR9R10, —N(COR9)R10, —COR9, —CONR9R10, and —COOR9;
- R6 and R7 are each independently selected from the group consisting of
- —H,
- —COR8,
- —COOR8,
- —CONR8R9,
- —SO2R8,
- —SO2NR8R9,
- lower alkyl which is unsubstituted or substituted by the group consisting of
- —OR5,
- —COOR8,
- —COR8,
- —CONR8R9,
- —CN,
- —NO2,
- —SO2R8,
- —SO2NR8R9,
- —NR8R9,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- heterocycle which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- aryl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9, and
- heteroaryl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- heterocycle which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- aryl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9,
- heteroaryl which is unsubstituted or substituted by the group consisting of —OR5, —COOR8, —COR8, —CONR8R9, —NR8R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R8, and —SO2NR8R9, and
- —NR6R7 can form a ring having 3 to 7 atoms, said ring not including any additional hetero atoms or including one or more additional hetero atoms and being unsubstituted or substituted by the group consisting of one or more of lower alkyl, —OR5, —COR8, —COOR8, CONR8R9, and —NR5R9;
- R8 is selected from the group consisting of
- —H,
- lower alkyl which is unsubstituted or substituted by the group consisting of cycloalkyl, heterocycle, aryl, heteroaryl, —OR9, —NR9R10, and —N(COR9)R10,
- aryl which is unsubstituted or substituted by the group consisting of —OR9, —COOR9, —COR9, —CONR10R9, —NR10R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R9, halogen, —SO2F and —SO2NR10R9,
- heteroaryl which is unsubstituted or substituted by the group consisting of —OR9, —COOR9, —COR9, —CONR10R9, —NR10R9, lower alkyl, cycloalkyl, heterocycle, —CN, —NO2, —SO2R9, halogen, —SO2F and —SO2NR10R9,
- cycloalkyl which is unsubstituted or substituted by the group consisting of —OR9, —COOR9, —COR9, —CONR10R9, —NR10R9, lower alkyl, heterocycle, aryl, —CN, —NO2, —SO2R9, and —SO2NR10R9, and
- heterocycle which is unsubstituted or substituted by the group consisting of —OR9, —COOR9, —COR9, —CONR10R9, —NR10R9, lower alkyl, cycloalkyl, aryl, —CN, —NO2, —SO2R9, and —SO2NR10R9;
- R9 and R10 are each independently selected from the group consisting of —H, lower alkyl and aryl;
- and
- X is selected from the group consisting of ═N— and
84 more elements
The compound (Z)-1,3-Dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one.
A compound selected from the group consisting of
- (Z)-1,3-Dihydro-4-phenyl-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (A),
- (Z)-4-(3-Aminophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (C),
- (Z)-4-(3-Aminophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one hydrochloride salt (D),
- (Z)-1,3-Dihydro-4-(4-methoxyphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (E),
- (Z)-1,3-Dihydro-4-(3-nitrophenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (F),
- (Z)-1,3-Dihydro-3-[(1H-pyrrol-2-yl)methylene]-4-(3-trifluoromethylphenyl)-2H-indol-2-one (G),
- (Z)-1,3-Dihydro-4-(4-methylphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (H),
- (Z)-1,3-Dihydro-4-(2-methylphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (I),
- (Z)-4-(2,4-Dichlorophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (J),
- (Z)-4-(4-Chlorophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (L),
- (Z)-1,3-Dihydro-4-(2-methoxyphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (M),
- (Z)-1,3-Dihydro-4-(1-naphthalenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (N),
- (Z)-4-(3-Chlorophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (P),
- (Z)-1,3-Dihydro-4-(4-hydroxyphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (R),
- (Z)-4-(3-Aminophenyl)-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (EE),
- (Z)-1,3-Dihydro-4-phenyl-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (GG), and
- (Z)-1,3-Dihydro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (HH).
14 more elements
A compound selected from the group consisting of
- (Z)-4-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-benzoic acid (Q),
- (Z)-3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-benzoic acid (BB),
- (Z)-4-[2,3-Dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-4-yl]-benzoic acid (II),
- (Z)-4-[2,3-Dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2-oxo-1H-indol-4-yl]-benzoic acid methyl ester (RR),
- (Z)-4-[5-Amino-2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-4-yl]-benzoic acid methyl ester (SS),
- (Z)-4-[2,3-Dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-5-[(2-thienylacetyl)amino]-1H-indol-4-yl]-benzoic acid methyl ester (WW),
- (Z)-4-[2,3-Dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-5-[(2-thienylacetyl)amino]-1H-indol-4-yl]-benzoic acid (XX),
- (Z)-4-[2,3-Dihydro-5-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2-oxo-1H-indol-4-yl]-benzoic acid methyl ester trifluoroacetate salt (AAA).
5 more elements
A compound selected from the group consisting of
- (Z)-N-[3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-phenyl]-4-hydroxybenzamide (S),
- (Z)-N-[3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methyl)ene]-1H-indol-4-yl]-phenyl]-3-bromobenzamide (T),
- (Z)-N-[3-[2,3-Dihydro-2-oxo3-[(1H-pyrrol-2-yl)methyl)ene]-1H-indol-4-yl]-phenyl]-3-cyanobenzamide (U),
- (Z)-N-[3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-phenyl]-3-nitrobenzamide (V),
- (Z)-N-[3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-phenyl]-4-fluorobenzamide (W),
- (Z)-N-[3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-phenyl]-4-nitrobenzamide (X),
- (Z)-N-[3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-phenyl]-4-methoxybenzamide (Y),
- (Z)-4-Amino-N-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]cyclohexanecarboxamide (Z),
- (Z)-N-[3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-phenyl]-4-(fluorosulfonyl)benzamide (AA),
- (Z)-N-[2-[[3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]amino]-2-oxoethyl]-4-(fluorosulfonyl)benzamide (CC).
7 more elements
A compound selected from the group consisting of
- (Z)-1,3-Dihydro-3-[(1H-pyrrol-2-yl)methylene]-4-(2-thiophenyl)-2H-indol-2-one (B),
- (Z)-1,3-Dihydro-4-(2,4-dimethoxy-6-pyrimidinyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (FF),
- (Z)-1,3-Dihydro-4-(5-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (MM),
- (Z)-1,3-Dihydro-4-(5-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one,
- (Z)-5-Amino-1,3-dihydro-4-(5-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one,
- (Z)-N-[2,3-Dihydro-4-(5-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-5-yl]-2-thiopheneacetamide (QQ),
- (Z)-1,3-Dihydro-4-(4-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (TT),
- (Z)-1,3-Dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (UU),
- (Z)-1,3-Dihydro-4-(6-indolyl)-3-[(3methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one,
- (Z)-5-Amino-1,3-dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one, and
- (Z)-N-[2,3-Dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-5-yl]-2-thiopheneacetamide (VV).
8 more elements
A compound selected from the group consisting of
- (Z)-N-[3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]methanesulfonamide (K),
- (Z)-N-[3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]-2-thiophenesulfonamide (O), and
- (Z)-N-[3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]-4-(phenylsulfonyl)-2-thiophenesulfonamide (DD).
A compound selected from the group consisting of
- (Z)-1,3-Dihydro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H- indol-2-one (JJ),
- (Z)-1,3-Dihydro--[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-4-phenyl-2H-l indol-2-one (KK),
- (Z)-N-[2,3-Dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-4-phenyl-1H-indol-5-yl]-2-thiopheneacetamide (LL),
- (Z)-5-Amino-1,3-dihydro-4-(4-hydroxyphenyl) -3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (NN),
- (Z)-N-[2,3-Dihydro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-5-yl]-2-thiopheneacetamide (OO),
- (Z)-5-Amino-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-4-phenyl-2H-indol-2-one (PP),
- (Z)-1,3-Dihydro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-5-nitro-4-phenyl-2H-indol-2-one (YY), and
- (Z)-1,3-Dihydro-5-fluoro-4-(4-hydroxyphenyl)-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one trifluoroacetate salt (ZZ).
5 more elements
A compound selected from the group consisting of
- (Z)-1,3-Dihydro-5-fluoro-4-(4-methoxyphenyl)-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one trifluoroacetate salt (BBB),
- (Z)-1,3-Dihydro-4-(3,4-dimethoxyphenyl)-5-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (CCC),
- (Z)-1,3-Dihydro-4-(2,4-dimethoxyphenyl)-5-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (DDD),
- (Z)-4-(1,3-Benzodioxol-5-yl)-1,3-dihydro-5-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one trifluoroacetate salt (EEE),
- (Z)-4-(3-Aminophenyl)-1,3-dihydro-5-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (FFF),
- (Z)-4-(3-Amino-4-methyl-phenyl)-1,3-dihydro-5-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (GGG),
- (Z)-1,3-Dihydro-5-fluoro-4-(3-hydroxyphenyl)-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (HHH),
- (Z)-1,3-Dihydro-5-fluoro-4-(4-hydroxyphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (III),
- (Z)-1,3-Dihydro-5-fluoro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (JJJ),
- 2-[3-[5-Fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-2,3-dihydro-1H-indol-4-yl]-phenylamino]-acetamide (KKK), and
- (Z)-1,3-Dihydro-5-fluoro-4-(4-hydroxymethyl-3-methoxy-phenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (LLL).
8 more elements
Dependencies are inferred from the claim text.