US 7,741,337 B2Granted

Azonafide derivatives, methods for their production and pharmaceutical compositions therefrom

AssigneeUnibioscreen S.A.

InventorsEric Van Quaquebeke, Jérôme Tuti, Laurent Van den Hove, Robert Kiss, Francis Darro

Life of this patent

Estimating the term…

Abstract

The present invention is directed to azonafide derivatives obtained by reacting azonafide with aldehydes, acyl halides, thioacyl halides, monoisocyanates, isothiocyanates, sulfonyl halides, monohalogenoalkanes, monohalogenoalkenes or monohalogenoalkynes, and are useful as active ingredients of pharmaceutical compositions for the prevention and treatment of cell proliferative disorders, in particular several forms of cancer.

Claims4

Dependent claims

A substituted azonafide derivative selected from the group consisting of:

11-{[(1Z)-(2,5-dihydroxyphenyl)methylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,5-dihydroxyphenyl)methylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-1,3-benzodioxol-5-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1E)-1,3-benzodioxol-5-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
methyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
4-chloro-N-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}butanamide;
2-(4-chlorophenyl)-N-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}acetamide;
1-(1,3-benzodioxol-5-yl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}urea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-pentylurea;
1-(1,3-benzodioxol-5-yl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-8-yl}urea;
1-(1,3-benzodioxol-5-yl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-8-yl}urea hydrochloride;
N-({2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-8-yl}carbamoyl)benzamide hydrochloride;
ethyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
phenyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
N-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-oxododecanamide;
N-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-oxo-5-phenylpentanamide;
ethyl 6-({2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}amino)-4,6-dioxohexanoate;
4-fluorophenyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
octyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
allyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
isobutyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
4-chlorobutyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
n-butyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-bromophenyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-(trifluoromethoxy)phenyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[2-methoxyethyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-isopropylphenyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-methoxyphenyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[ethyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[allyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[2-methoxyphenyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-(3-pyridyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-(2-trifluoromethoxy4-bromophenyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-(2-furylmethyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-trifluoromethylphenyl]thiourea;
1-(1,3-benzodioxol-4-yl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}thiourea;
1-(2,1,3-benzothiadiazol-5-yl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}thiourea;
1-(1,3-benzodioxol-4-ylmethyl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[2-(trifluoromethoxy)phenyl]thiourea;
11-{[(1Z)-(2-methylbenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-methylbenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-methylbenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-methoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-methoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-methoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-propoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-phenoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3 (2H)-dione;
11-{[(1Z)-3-(3,4-dichlorophenoxy)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-3-(3,5-dichlorophenoxy)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-bromobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-bromobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-bromobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-chlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-chlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-chlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,3-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,4-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,6-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3,4-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3,5-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,3-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,4-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,5-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,6-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3,4-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3,5-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,3,4-trifluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-(trifluoromethyl)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-(trifluoromethyl)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-(trifluoromethyl)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-(trifluoromethoxy)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-aminobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-nitrobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-nitrobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-nitrobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(Z)-(3-cyanobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(Z)-(4-cyanobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
1-{[(1Z)-(4-dimethylaminobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-diethylaminobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-methylbenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-methylbenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-methylbenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-methoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-methoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-methoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-propoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-phenoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-3-(3,4-dichlorophenoxy)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-3-(3,5-dichlorophenoxy)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-bromobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-bromobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-bromobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-chlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-chlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-chlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,3-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,4-dichlorobenzylidene]amino}-2-[2-(dimethylamino)-ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,6-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3,4-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3,5-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,3-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,4-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,5-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,6-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3,4-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3,5-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,3,4-trifluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-(trifluoromethyl)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-(trifluoromethyl)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-(trifluoromethyl)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-(trifluoromethoxy)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-aminobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-nitrobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-nitrobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-nitrobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-cyanobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-cyanobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-dimethylaminobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-diethylaminobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(cyclohexylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(cyclooctylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(cyclohexylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(cyclooctylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(pyrrol-2-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(thien-2-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(thien-3-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(pyrrolidinylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(pyrid-4-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(pyrid-3-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(pyrrol-2-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(thien-2-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(thien-3-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(pyrrolidinylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(pyrid-4-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
and
11-{[(1Z)-(pyrid-3-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione,
and/or a pharmaceutically acceptable salt thereof.

140 more elements

Dependencies are inferred from the claim text.

Facts

Application: 12/093,086Filed 9 Nov 2006 · us provisional application
Priority: EP 054472519 Nov 2005
Published: US 2008/0292585 A127 Nov 2008
Granted: 22 Jun 2010
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07D 405/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61P 35/00
Antineoplastic agents
C07D 221/18
Ortho- or peri-condensed ring systems: ring systems of four or more rings
C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links

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Application60/734,912Us provisional application · filed 9 Nov 2005
US 2008/0292585 A1Pre-grant publication · published 27 Nov 2008
US 7,741,337 B2This patent

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Abstract

A substituted azonafide derivative selected from the group consisting of:

11-{[(1Z)-(2,5-dihydroxyphenyl)methylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,5-dihydroxyphenyl)methylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-1,3-benzodioxol-5-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1E)-1,3-benzodioxol-5-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
methyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
4-chloro-N-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}butanamide;
2-(4-chlorophenyl)-N-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}acetamide;
1-(1,3-benzodioxol-5-yl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}urea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-pentylurea;
1-(1,3-benzodioxol-5-yl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-8-yl}urea;
1-(1,3-benzodioxol-5-yl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-8-yl}urea hydrochloride;
N-({2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-8-yl}carbamoyl)benzamide hydrochloride;
ethyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
phenyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
N-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-oxododecanamide;
N-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-oxo-5-phenylpentanamide;
ethyl 6-({2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}amino)-4,6-dioxohexanoate;
4-fluorophenyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
octyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
allyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
isobutyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
4-chlorobutyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
n-butyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-bromophenyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-(trifluoromethoxy)phenyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[2-methoxyethyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-isopropylphenyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-methoxyphenyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[ethyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[allyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[2-methoxyphenyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-(3-pyridyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-(2-trifluoromethoxy4-bromophenyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-(2-furylmethyl]thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-trifluoromethylphenyl]thiourea;
1-(1,3-benzodioxol-4-yl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}thiourea;
1-(2,1,3-benzothiadiazol-5-yl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}thiourea;
1-(1,3-benzodioxol-4-ylmethyl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}thiourea;
1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[2-(trifluoromethoxy)phenyl]thiourea;
11-{[(1Z)-(2-methylbenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-methylbenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-methylbenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-methoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-methoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-methoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-propoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-phenoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3 (2H)-dione;
11-{[(1Z)-3-(3,4-dichlorophenoxy)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-3-(3,5-dichlorophenoxy)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-bromobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-bromobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-bromobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-chlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-chlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-chlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,3-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,4-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,6-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3,4-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3,5-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,3-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,4-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,5-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,6-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3,4-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3,5-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2,3,4-trifluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-(trifluoromethyl)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-(trifluoromethyl)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-(trifluoromethyl)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-(trifluoromethoxy)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-aminobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(2-nitrobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(3-nitrobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-nitrobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(Z)-(3-cyanobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(Z)-(4-cyanobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
1-{[(1Z)-(4-dimethylaminobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(4-diethylaminobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-methylbenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-methylbenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-methylbenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-methoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-methoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-methoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-propoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-phenoxybenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-3-(3,4-dichlorophenoxy)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-3-(3,5-dichlorophenoxy)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-bromobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-bromobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-bromobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-chlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-chlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-chlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,3-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,4-dichlorobenzylidene]amino}-2-[2-(dimethylamino)-ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,6-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3,4-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3,5-dichlorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,3-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,4-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,5-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,6-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3,4-difluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3,5-fluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2,3,4-trifluorobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-(trifluoromethyl)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-(trifluoromethyl)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-(trifluoromethyl)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-(trifluoromethoxy)benzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-aminobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(2-nitrobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-nitrobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-nitrobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(3-cyanobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-cyanobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-dimethylaminobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(4-diethylaminobenzylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(cyclohexylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(cyclooctylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(cyclohexylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(cyclooctylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(pyrrol-2-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(thien-2-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(thien-3-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(pyrrolidinylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(pyrid-4-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(pyrid-3-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(pyrrol-2-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(thien-2-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(thien-3-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
8-{[(1Z)-(pyrrolidinylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
11-{[(1Z)-(pyrid-4-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione;
and
11-{[(1Z)-(pyrid-3-ylmethylidene]amino}-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione,
and/or a pharmaceutically acceptable salt thereof.

140 more elements

Facts

Application

12/093,086Filed 9 Nov 2006 · us provisional application

Priority

EP 054472519 Nov 2005

Published

US 2008/0292585 A127 Nov 2008

Granted

22 Jun 2010

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07D 405/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61P 35/00
Antineoplastic agents
C07D 221/18
Ortho- or peri-condensed ring systems: ring systems of four or more rings
C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links