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US 7,119,090 B2Granted
Pyrrole substituted 2-indolinone protein kinase inhibitors
AssigneeSugen, Inc.
InventorsPeng Cho Tang, Li Sun, Gerald McMahon
Life of this patent
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Abstract
The present invention relates to novel pyrrole substituted 2-indolinone compounds and physiologically acceptable salts and prodrugs thereof which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.
Claims10
A pyrrole substituted 2-indolinone having the chemical
- structure:
- wherein:
- R1 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, hydroxy, alkoxy, C-carboxy, O-carboxy, acetyl, C-amido, C-thioamido, sulfonyl and trihalomethanesulfonyl;
- R2 is selected from the group consisting of hydrogen, halo, alkyl, cycloalkyl, aryl, heteroaryl and heteroalicyclic;
- R3, R4, R5 and R6 are independently selected from the group consisting of hydrogen, alkyl, trihaloalkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, heteroalicyclic, hydroxy, alkoxy, aryloxy, mercapto, alkylthio, arylthio, sulfinyl, sulfonyl, S-sulfonamido, N-sulfonamido, trihalomethane-sulfonamido, carbonyl, C-carboxy, O-carboxy, C-amido, N-amido, cyano, nitro, halo, O-carbamyl, N-carbamyl, O-thiocarbamyl, N-thiocarbamyl, amino and —NR11R12;
- R11 and R12 are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl, carbonyl, acetyl, sulfonyl, trifluoromethanesulfonyl and, combined, a five- or six-member heteroalicyclic ring;
- R7 is selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, heteroalicyclic, hydroxy, alkoxy, aryloxy, carbonyl, acetyl, C-amido, C-thioamido, amidino, C-carboxy, O-carboxy, sulfonyl and trihalomethane-sulfonyl;
- R8 and R10 are independently selected from the group consisting of hydrogen, alkyl, trihaloalkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, heteroalicyclic, hydroxy, alkoxy, aryloxy, mercapto, alkylthio, arylthio, sulfinyl, sulfonyl, S-sulfonamido, N-sulfonamido, carbonyl, C-carboxy, O-carboxy, cyano, nitro, halo, O-carbamyl, N-carbamyl, O-thiocarbamyl, N-thiocarbamyl, C-amido, N-amido, amino and —NR11R12 and
- R9 is alkyl substituted with —NR11R12.
6 more elements
A compound selected from the group consisting of:
- 3-[3,5-Dimethyl-4-(3-morpholin-4-ylpropyl)-1H-pyrrol-2-ylmethylene]-1,3-dihydroindol-2-one
- 5-Bromo-3-[3,5-dimethyl-4-(3-morpholin-4-ylpropyl)-1H-pyrrol-2-ylmethylene]-1,3-dihydroindol-2-one
- 3-[3,5-Dimethyl-4-(3-morpholin-4-ylpropyl)-1H-pyrrol-2-ylmethylene]-6-phenyl-1,3-dihydroindol-2-one
- 3-[3,5-Dimethyl-4-(3-morpholin-4-ylpropyl)-1H-pyrrol-2-ylmethylene]-6-2-methoxyphenyl)-1,3-dihydroindol-2-one
- 3-[3,5-Dimethyl-4-(3-morpholin-4-ylpropyl)-1H-pyrrol-2-ylmethylene]-6-(3-methoxyphenyl)-1,3-dihydroindol-2-one
- 3-[3,5-Dimethyl4-(3-morpholin-4-ylpropyl)-1 H-pyrrol-2-ylmethylene]-6-(4-methoxyphenyl)-1,3-dihydroindol-2-one
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-1,3-dihydroindol-2-one
- 5-Bromo-3-[4-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-1,3-dihydroindol-2-one
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-6-pheny-1,3-dihydroindol-2-one
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-6-(2-methoxyphenyl)-1,3-dihydroindol-2-one
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-6-(3-methoxyphenyl)-1,3-dihydroindol-2-one
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-6-(4-methoxyphenyl)-1,3-dihydroindol-2-one
- 5-Chloro-3-[4-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-1,3-dihydroindol-2-one
- 6-Chloro-3-[4-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-1,3-dihydroindol-2-one
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-5-methoxy-1,3-dihydroindol-2-one
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-6-methoxy-1,3-dihydroindol-2-one
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-5-methyl-1,3-dihydroindol-2-one
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-4-methyl-1,3-dihydroindol-2-one
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]4-(2-hydroxyethyl)-1,3-dihydroindol-2-one
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3 -dihydro-1H-indole-5-sulfonic acid amide
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid isopropylamide
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-5-(morpholine-4-sulfonyl)-1,3-dihydroindol-2-one, and
- 3-[4-(3-Dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid dimethylamide.
20 more elements
Dependencies are inferred from the claim text.