US 7,094,798 B1Granted

Inhibitors of checkpoint kinases (Wee1 and Chk1)

AssigneePfizer Inc.

InventorsRichard John Booth, Ellen Myra Dobrusin, Alan Kraker, Lorna Helen Mitchell, William Alexander Denny, Jeffrey Bruce Smaill, Andrew Mark Thompson, Florence Oliver Joseph McCarthy, Ho Huat Lee, Brian Desmond Palmer

Life of this patent

Estimating the term…

Abstract

This invention relates to pyrrolocarbazole derivatives according formula I wherein R1, R2, R7, R8, R9, X and Y are as defined in the specification wherein said derivatives specifically inhibit one or both of the checkpoint kinases Wee1 and Chk1

Claims9

Dependent claims

A compound of Formula I

wherein
each dashed line represents an optional bond;
R1 is
an aryl optionally substituted with up to five substituents selected from halogen, alkyl, haloalkyl, hydroxyl, nitro, cyano, C(O)R3, OR3, S(O)mR3, NR3R4, OC(O)R3, NR3(CO)OR4, CH2NR3R4, CH2OR3, COOR3, CONR3R4, NR3COR4, SO2NR3R4, CONHSO2R3, NR3S(O)mR4 NHCONR3R4, NR3CONHR4;
m is 0–2;
X is hydrogen or halogen;
Y1 is NR10;
R9 is hydroxyl;
r is 0–6;
R2, R7, R8 and R10 are in each instance independently selected from ((CR5R6)nT)a(CR11R12)b)-Z wherein the sum n, a and b is in each instance less than 10;
T may be absent, or, when present, is in each instance independently selected from O, CONR3, CONHSO2, S(O)m, NR3, NR3—O, O—S(O)m, S(O)m—O, NR3—S(O)2, or S(O)2—NR3;
n is in each instance independently 0–6;
a is in each instance independently 0–6;
b is in each instance independently 0–6;
Z is selected from hydrogen, halogen, alkyl, haloalkyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, cyano, nitro, hydroxy, C(O)R3, CONHSO2R3, OR3, S(O)mR3, OSO2R3, NR3R4, CO2R3, CONR3R4, NR3COR4, SO2NR3R4, OPO(OR3)(OR4), CH═CR3R4, CCR3, (C═NR3)NHR4, NH(C═NR3)NHR4, NH(C═NH)NR3R4, wherein the alkyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl group may be substituted with up to four groups independently selected from halogen, alkyl, hydroxyl, nitro, cyano, OR3, S(O)mR3, NR3R4, OC(O)R3, NR3(CO)OR4, C(O)R3, COOR3, CONR3R4, NR3COR4, SO2NR3R4, CONHSO2R3, NR3S(O)mR4, CH2NR3R4, CH2OR3, NHCONR3R4, NR3CONHR4;
R5, R6, R11 and R12 are in each instance independently selected from hydrogen, hydroxyl, alkyl, haloalkyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, heterocyclyl, halogen, cyano, nitro, CH2NR3R4, CH2OR3, C(O)R3, OR3, S(O)mR3, NR3R4, COOR3, CONR3R4, SO2NR3R4, NHCONR3R4, NR3CONHR4;
wherein the alkyl, haloalkyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl group may be substituted with up to four groups independently selected from halogen, alkyl, hydroxyl, nitro, cyano, OR3, S(O)mR3, NR3R4, OC(O)R3, NR3(CO)OR4, C(O)R3, COOR3, CONR3R4, NR3COR4, SO2NR3R4, CONHSO2R3, NR3S(O)mR4, NHCONR3R4, NR3CONHR4;
R5 and R6 or R11 and R12 together with the carbon atom to which they are attached may form a carbonyl group;
or together with the carbon or heteratom to which they are attached may form a cycloalkyl or heterocyclyl group, said carbonyl, cycloalkyl or heterocyclyl group may be substituted with up to four groups independently selected from halogen, hydroxyl, nitro, cyano, alkyl, haloalkyl, alkyl, nitro, cyano, OR3, S(O)mR3, NR3R4, OC(O)R3, NR3(CO)OR4, C(O)R3, COOR3, CONR3R4, NR3COR4, S(O)2NR3R4, CONHSO2R3, NR3S(O)mR4, NHCONR3R4, NR3CONHR4;
R3, R4 are independently selected from hydrogen, alkyl, haloalkyl or a substituted or unsubstituted carbocyclic group selected from cycloalkyl, cycloalkenyl, heterocyclyl, aryl, and heteroaryl, wherein the said alkyl, or a substituted group may be substituted with up to 4 groups selected from halogen, hydroxyl, nitro, cyano, alkyl, haloalkyl, alkyloxy, carboxy, COOH, CONH2, NHCOCH3, N(CH3)2, NHCH3, thiomethyl, thioethyl, SOCH3, SO2CH3;
R3 and R4 together with the carbon atom or heteroatom to which they are attached may form a cycloalkyl or heterocyclyl group substituted with up to four groups independently selected from halogen, hydroxyl, nitro, cyano, alkyl, haloalkyl, alkyloxy, formyl, carboxy, acetyl, CH2NH2, CH2OH, COOH, CONH2, NHCOCH3, N(CH3)2, thiomethyl, thioethyl, SOCH3, SO2CH3, alkoxycarbonyl, alkylcarbonyl, alkynylamino, aminoalkyl, aminoalkylcarbonyl, amino, mono- or dialkylamino, or
R3 and R4 together with the nitrogen to which they are attached may form a heterocyclic ring containing 3–8 members, up to four of which members are optionally carbonyl groups or heteroatoms independently selected from oxygen, sulfur, S(O), S(O)2, and nitrogen, wherein the carbocyclic group is unsubstituted or substituted with up to four groups independently selected from halogen, hydroxy, hydroxyalkyl, alkyl, haloalkyl, alkoxy, alkoxycarbonyl, alkylcarbonyl, alkynylamino, aminoalkyl, aminoalkylcarbonyl, amino, mono- or dialkylamino.

19 more elements

The compounds:

2-(4-(2,6-Dichlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)ethyl methanesulfonate;
2-94-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)ethyl methanesulfonate;
3-(4-(2,6-Dichlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-[2-(dimethylamino)ethyl]propanamide;
3-(4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-[2-(dimethylamino)ethyl]propanamide;
3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-(1H-tetraazol-5-yl) propanamide;
3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-[2-(1H-imidazol-5-yl)ethyl] propanamide;
3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-[2-(4-morpholinyl) ethyl] propanamide;
3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-[2-(dimethylamino)ethyl]propanamide;
3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl) propanenitrile;
3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl) propanoic acid;
3-(9-Hydroxy-1,3-dioxo-4-phenyl-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl) propanamide;
3-(9-Hydroxy-1,3-dioxo-4-phenyl-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl) propanoic acid;
4-(2,3-Dichlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-5-hydroxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-Dibromophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-Dichloro-3-hydroxyphenyl)-9-hydroxypyrrolo[3,4-c] carbazole-1,3(2H, 6H)-dione;
4-(2,6-Dichloro-4-hydroxyphenyl)-9-hydroxypyrrolo[3,4-c] carbazole-1,3(2H, 6H)-dione;
4-(2,6-Dichlorophenyl)-9-hydroxy-6-(2-hydroxyethyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-Dichlorophenyl)-9-hydroxy-6-(3-hydroxypropyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-Dichlorophenyl)-9-hydroxy-6-[3-(1H-imidazol-1-yl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-Dichlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-Dimethoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Bromophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-3-hydroxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-4-hydroxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-6-hydroxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-(2-hydroxyethyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (112);
4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-(3-hydroxypropyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-[3-(4-morpholinyl) propyl] pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-6-methoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-6-(2,3-dihydroxypropyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-6-(2-hydroxyethyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3 (2H,6H)-dione;
4-(2-Chlorophenyl)-6-(3,4-dihydroxybutyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-6-ethyl-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-(2-hydroxypropyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)dione;
4-(2-Chlorophenyl)-9-hydroxy-6-(3-methoxypropyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[(2R)-3-hydroxy-2-methylpropyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-[(2S)-3-hydroxy-2-methylpropyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[2-(1H-1,2,4-triazol-5-ylsulfinyl)ethyl]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[2-(1H-1,2,4-triazol-5-ylsulfonyl)ethyl]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[2-(1H-imidazol-2-ylsulfanyl) ethyl]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[2-(1H-imidazol-2-ylsulfinyl)ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[2-(1H-imidazol-2-ylsulfonyl)ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[2-(1H-tetraazol-5-yl)ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[2-(4H-1,2,4-triazol-3-ylsulfanyl)ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[2-hydroxy-3-(4-morpholinyl)propyl]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[2-hydroxy-3-(methylamino)propyl]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[3-(1H-imidazol-1-yl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[3-(1H-tetraazol-5-yl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[3-(methylsulfanyl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-isopropylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-methylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(3-Amino-2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(3-Aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(3-Chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)butanenitrile;
4-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)butanoic acid;
4-(4-Amino-2-bromophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione);
4-(4-Amino-2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-(2-Chloroethyl)-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-(3-Bromopropyl)-4-(2,6-dichlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (233);
6-(3-Bromopropyl)-4-(2-chloro-6-methoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-(3-Bromopropyl)-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-Acetyl-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-Butyl-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(2-hydroxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;9-Hydroxy-4-(2-iodophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;9-Hydroxy-4-(2-nitrophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(3-thienyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(4-hydroxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-[2-(methylsulfanyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-6-(2-hydroxyethyl)-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-6-(2-hydroxyethyl)-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-6-(3-hydroxypropyl)-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
Methyl 3-(4-(2-chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)propanoate;
N-[3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanoyl]-2-(dimethylamino)ethanesulfonamide;
N-[3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl) propanoyl]benzenesulfonamide;
N-[3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl) propanoyl]methanesulfonamide;
N-[4-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)butanoyl]benzenesulfonamide;
N-[4-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)butanoyl]methanesulfonamide;
2-(9-Hydroxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl) benzonitrile;
3-(9-Hydroxy-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazol-4-yl)-benzonitrile;4-(2,3-Dichlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-5-hydroxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-Dibromophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-Dichloro-3-hydroxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-Dichloro-4-hydroxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H, 6H)-dione;4-(2,6-Dichlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-Dimethoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;4-(2,6-Dimethylphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;4-(2-Acetyl-phenyl)-9-hydroxy-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Bromo-4-nitrophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Bromophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-3-hydroxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-4-hydroxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-4-nitrophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-6-hydroxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-6-methoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Ethoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Ethylphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(3-Amino-2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(3-Aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(3-Chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(4-Amino-2-bromophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione);
4-(4-Amino-2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(4-Aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(4-Chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(5-Amino-2-methoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-[1,1-Bipbenyl]-2-yl-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-Furan-2-yl-9-hydroxy-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
9-Hydroxy-4-(2-hydroxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(2-iodophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(2-methylsulfanyl-phenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
9-Hydroxy-4-(2-nitrophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(2-thienyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(2-trifluoromethylphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(3-hydroxy-4-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(3-hydroxymethyl-phenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
9-Hydroxy-4-(3-hydroxy-phenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
9-Hydroxy-4-(3-hydroxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(3-nitrophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(3-thienyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(3-trifluoromethoxy-phenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
9-Hydroxy-4-(4-hydroxymethylphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(4-hydroxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(4-trifluoromethoxy-phenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
9-Hydroxy-4-[2-(hydroxymethyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-[2-(methylsulfanyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-[2-(methylsulfinyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-m-tolyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
9-Hydroxy-4-o-tolyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-chlorophenyl)-9-hydroxy-6-propylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
2-(4-(2-chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)acetamide;
2-{[3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl) propyl]amino}benzoic acid;
3-(4-(2,6-Dichlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl) propanoic acid;
3-(4-(2-chlorophenyl)-9-(formylamino)-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)-N-[2-(dimethylamino)ethyl]propanamide;
3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)-N-(2,2,6,6-tetramethyl-4-piperidinyl);
3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H0-yl)-N-[2-(1H-imidazol-5-yl)ethyl]propanamide;
3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)-N-[2-(dimethylamino)ethyl]-N-methylpropanamide;
3,9-dihydroxy-4-phenyl-3,6-dihydropyrrolo[3,4-c]carbazol-1(2H)-one;
3-{[3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl) propyl]amino}benzoic acid;
4-(2,6-dichlorophenyl)-6-[3-(dimethylamino) propyl]-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-Dichlorophenyl)-6-{3-[(cis)-3,5-dimethylpiperazinyl]propyl}-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-dichlorophenyl)-8-[3-(dimethylamino)propoxy]-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-dichlorophenyl)-8-[4-(dimethylamino)butyl]-9-hydroxy-6-methylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-dichlorophenyl)-9-hydroxy-6-[2-(4-methyl-1-piperazinyl) ethyl]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-dichlorophenyl)-9-hydroxy-6-[2-(4-morpholinyl) ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-dichlorophenyl)-9-hydroxy-6-[3-(1H-imidazol-1-yl) propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-dichlorophenyl)-9-hydroxy-6-[3-(4-methyl-1-piperazinyl) propyl]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-dichlorophenyl)-9-hydroxy-6-[3-(4-morpholinyl) propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-dichlorophenyl)-9-hydroxy-6-[3-(dimethylamino)ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-dichlorophenyl)-9-hydroxy-6-[3-(methylamino)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-dichlorophenyl)-9-hydroxy-6-methyl-8-[3-(methylamino)propoxy]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2,6-dichlorophenyl)-9-hydroxy-8-[4-(methylamino)butyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-bromophenyl)-8-[3-(dimethylamino)propoxy]-9-hydroxy-6-methylpyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-bromophenyl)-8-[3-(dimethylamino)propoxy]-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-bromophenyl)-8-[4-(dimethylamino)butyl]-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-bromophenyl)-9-hydroxy-6-methyl-8-[3-(methylamino)propoxy]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-bromophenyl)-9-hydroxy-8-[3-(methylamino)propoxy]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-bromophenyl)-9-hydroxy-8-[4-(methylamino)butyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-6-methoxyphenyl)-6-{3-[cis-3,5-dimethylpiperazinyl]propyl}-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chloro-6-methoxyphenyl)-8-[3-(dimethylamino)propoxy]-9-hydroxy-6-methylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chloro-6-methoxyphenyl)-8-[3-(dimethylamino)propoxy]-9-hydroxypyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chloro-6-methoxyphenyl)-8-[4-(dimethylamino)butyl]-9-hydroxy-6-methylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chloro-6-methoxyphenyl)-8-[4-(dimethylamino)butyl]-9-hydroxypyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-[2-(4-morpholinyl)ethyl]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chloro-6-methoxyphenyl)-9-hydroxy-6-methyl-8-[3-(methylamino) propoxy]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chloro-6-methoxyphenyl)-9-hydroxy-8-[3-(methylamino)propoxy]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chloro-6-methoxyphenyl)-9-hydroxy-8-[4-(methylamino)butyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-1,9-dihydroxy-6-(3-hydroxypropyl)-1,6-dihydropyrrolo[3,4-c]carbazol-3(2H)-one;
4-(2-chlorophenyl)-3,9-dihydroxy-6-(3-hydroxypropyl)-3,6-dihydropyrrolo[3,4-c]carbazol-1(2H)-one;
4-(2-Chlorophenyl)-6-[3-(dimethylamino)-2-hydroxypropyl]-9-hydroxypyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-6-[3-(dimethylamino)propyl]-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-6-{3-[(cis)-3,5-dimethylpiperazinyl]propyl}-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-6-cyclopentyl-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-phenyl)-8-(3-diethylamino-propoxy)-9-hydroxy-6-(2-hydroxy-ethyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-(3-dimethylamino-propoxy)-9-hydroxy-6-(3-hydroxy-propyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-chlorophenyl)-8-[3-(dimethylamino)propoxy]-9-hydroxy-6-(2-hydroxyethyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-8-[3-(dimethylamino)propoxy]-9-hydroxy-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-8-[3-(dimethylamino)propoxy]-9-hydroxy-6-methylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-8-[3-(dimethylamino)propoxy]-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-8-[4-(dimethylamino)butanoyl]-9-hydroxy-6-methylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-8-[4-(dimethylamino)butyl]-9-hydroxy-6-(2-hydroxyethyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-8-[4-(dimethylamino)butyl]-9-hydroxy-6-(3-hydroxypropyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-8-[4-(dimethylamino)butyl]-9-hydroxy-6-(3-hydroxypropyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-8-[4-(dimethylamino)butyl]-9-hydroxy-6-methylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-8-[4-(dimethylamino) butyl]-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-8-{[3-(dimethylamino)propyl]sulfinyl}-9-hydroxy-6-methylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-8-{3-[(3,5-dimethylpiperazinyl]propxy}-9-hydroxy-6-methylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-8-ethyl-9-hydroxy-6-methylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-(hydroxymethyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-(2,2,2-trifluoroethyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-[3-(4-methyl-piperazin-1-yl)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-(2-hydroxyethyl)-8-[3-(4-morpholinyl) propoxy]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-(2-hydroxyethyl)-8-[3-(methylamino) propoxy]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-(2-hydroxyethyl)-8-[4-(methylamino) butyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-(2-phenylethyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-(2-propynyl)pyrrolo[3,4-c]carbazole-1,3(2H, 6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-(3-hydroxypropyl)-4,5,6,10c-tetrahydropyrrolo [3,4-c]carbazole-1,3(2H,3aH)-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(3-hydroxy-propyl)-8-(3-pyrrolidin-1-yl-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-chlorophenyl)-9-hydroxy-6-(3-hydroxypropyl)-8-[3-(1-pyrrolidinyl) propoxy]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(3-hydroxy-propyl)-8-[3-(4-methyl-piperazin-1-yl)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-chlorophenyl)-9-hydroxy-6-(3-hydroxypropyl)-8-[3-(methylamino) propoxy]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(3-hydroxy-propyl)-8-piperidin-4-yl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-chlorophenyl)-9-hydroxy-6-(4,4,4-trifluorobutyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-(4-pentenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6,8-bis (2-hydroxyethyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-[2-(1H-imidazol-1-yl) ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-[2-(4-methyl-1-piperazinyl) ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-[2-(4-morpholinyl)ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-[2-(phenylsulfanyl)ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-[3-(4-methyl-1-piperazinyl) propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-[3-(4-morpholinyl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-[3-(dimethylamino)ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-[3-(methylamino)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-isobutylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-isopentylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(4-morpholin-4-yl-butyl)-6H-pyrrolo [3,4-c]carbazole-1,3-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-methyl-8-[3-(1-pyrrolidinyl) propoxy]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-6-methyl-8-[3-(4-morpholinyl)propoxy]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-methyl-8-[3-(methylamino)propoxy]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-methyl-8-[4-(methylamino)butanoyl]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-methyl-8-[4-(methylamino)butyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-methyl-8-{[3-(methylamino)propyl]sulfonyl}pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-chlorophenyl)-9-hydroxy-6-pentylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-8-(2-hydroxyethyl)-6-methylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-(4-hydroxy-butoxy)-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-(4-hydroxy-butyl)-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chlorophenyl)-9-hydroxy-8-[3-(methylamino)propoxy]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-8-[4-(1-pyrrolidinyl)butyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy=8-[4-(methylamino) butyl]-6-propylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(2-Chlorophenyl)-9-hydroxy-8-[4-(methylamino) butyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(5-Amino-2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-(5-Amino-2-methoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
4-{[3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl) propyl]amino}benzoic acid;
6-(2-aminoethyl)-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3 (2H,6H)-dione;
6-(2-anilinoethyl)-4-(2,6-dichlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-(2-anilinoethyl)-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-(3-aminopropyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-(3-anilinopropyl)-4-(2,6-dichlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-(3-anilinopropyl)-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-(3-Anilinopropyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)—dione;
6-(3-Bromo-propyl)-4-(2-chloro-phenyl)-8-(3-dimethylamino-propoxy)-9-hydroxy-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
6-(3-butenyl)-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-[3-(Benzylamino)propyl]-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-[3-(diethylamino) propyl]-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-[6-(dimethylamino)hexyl]-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-allyl-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-Benzyl-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-butyl-4-(2,6-dichlorophenyl)-8-[3-(dimethylamino) propoxy]-9-hydroxypyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
6-butyl-4-(2,6-dichlorophenyl)-8-[4-(dimethylamino) butyl]-9-hydroxypyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
6-butyl-4-(2,6-dichlorophenyl)-9-hydroxy-8-[3-(methylamino) propoxy]pyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
6-butyl-4-(2,6-dichlorophenyl)-9-hydroxy-8-[4-(methylamino) butyl]pyrrolo[3,4-c] carbazole-1,3(2H,6H)-dione;
6-butyl-4-6-methoxyphenyl-)-8-[3-(dimethylamino) propoxy]-9-hydroxypyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
6-butyl-4-(2-chloro-6-methoxyphenyl)-8-[4-(dimethylamino) butyl]-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-butyl-4-(2-chloro-6-methoxyphenyl)-9-hydroxy-8-[3-(methylamino) propoxy]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-butyl-4-(2-chlorophenyl)-8-[3-(dimethylamino) propoxy]-9-hydroxypyrrolo [3,4-c]carbazole-1,3(2H,6H)-dione;
6-butyl-4-(2-chlorophenyl)-8-[4-(dimethylamino) butyl]-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-butyl-4-(2-chlorophenyl)-9-hydroxy-8-[3-(methylamino) propoxy]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-butyl-4-(2-chlorophenyl)-9-hydroxy-8-[4-(1-pyrrolidinyl) butyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
6-sec-butyl-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
7-(2-Amino-1-hydroxy-ethyl)-4-(2-chlorophenyl)-9-hydroxy-6-oxa-2-aza-[c]fluorene-1,3-dione;
8-(2,3-Dihydroxypropyl)-9-hydroxy-6-methyl-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
8-(4-aminobutyl)-4-(2-chlorophenyl)-9-hydroxy-6-methylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
8-(4-aminobutyl)-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
8-[2-(Dimethylamino)ethyl]-9-hydroxy-6-methyl-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
8-[3-(Dimethylamino)propoxy]-9-hydroxy-6-methyl-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
8-[3-(Dimethylamino)propyl]-9-hydroxy-6-methyl-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
8-{3-[Bis-(2-hydroxy-ethyl)-amino]-propoxy}-4-(2-chlorophenyl)-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
8-Ethyl-9-hydroxy-6-methyl-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(2-hydroxyphenyl)-6-(3-hydroxypropyl) pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-(2-methoxyphenyl)-6-[2-(4-morpholinyl)ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4,5-diphenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-4-phenyl-6-[3-(1-piperazinyl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-hydroxy-4-phenyl-6-[3-(1-piperidinyl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-hydroxy-4-phenyl-6-[3-(1-pyrrolidinyl) propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-5-methyl-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-6-(3-hydroxypropyl)-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-6-(6-hydroxyhexyl)-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-6-[2-(1H-imidazol-1-yl)ethyl]-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-6-[2-(4-morpholinyl) ethyl]-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-hydroxy-6-[2-(methylamino)ethyl]-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-6-[3-(1H-imidazol-1-yl) propyl]-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-hydroxy-6-[3-(4-methyl-1-piperazinyl)propyl]-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-6-[3-(4-morpholinyl) propyl]-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-6-[3-(niethylamino) propyl]-4-phenylpyrrolo[3,4-c]carbazole-1,3 (2H,6H)-dione;
9-hydroxy-6-[6-(4-methyl-1-piperazinyl)hexyl]-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-6-methyl-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-8-(2-hydroxyethyl)-6-methyl-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
9-Hydroxy-8-(3-hydroxypropyl)-6-methyl-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione;
N-[2-(Dimethylamino) ethyl]-3-(9-hydroxy-1,3-dioxo-4-phenyl-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl) propanamide;
and
N-[2-(Dimethylamino)ethyl]-3-(9-hydroxy-4-(2-methoxyphenyl)-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl) propanamide.

288 more elements

The compounds:

4-(4-Amino-2-methoxy-phenyl)-9-hydroxy-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-(4-morpholin-4-yl-butyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
hydrochloride salt;
4-(2-Chloro-phenyl)-8-[3-(3,5-dimethyl-piperazin-1-yl)-propoxy]-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-(3-hydroxy-propoxy)-6-methyl-6H-pyrrolo [3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-(4-methylamino-butyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
2-(9-Hydroxy-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazol-4-yl)-benzamide;
4-(2-Chloro-phenyl)-8-(3-dimethylamino-propoxy)-9-hydroxy-6-(2-hydroxy-ethyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-(3-pyrrolidin-1-yl-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(3-methylamino-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-(3-dimethylamino-propoxy)-9-hydroxy-6-(3-hydroxy-propyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
6-(3-Bromo-propyl)-4-(2-chloro-phenyl)-8-(3-dimethylamino-propoxy)-9-hydroxy-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(3-hydroxy-propyl)-8-(3-pyrrolidin-1-yl-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-[3-(3,5-dimethyl-piperazin-1-yl)-propoxy]-9-hydroxy-6-(3-hydroxy-propyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-(4-hydroxy-butyl)-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
8-{3-[Bis-(2-hydroxy-ethyl)-amino]-propoxy}-4-(2-chloro-phenyl)-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(3-hydroxy-propyl)-8-[3-(4-methyl-piperazin-1-yl)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-(4-hydroxy-butoxy)-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(4-morpholin-4-yl-butyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-[3-(4-methyl-piperazin-1-yl)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-(3-diethylamino-propoxy)-9-hydroxy-6-(2-hydroxy-ethyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(3-hydroxy-propyl)-8-piperidin-4-yl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-(4-dimethylamino butyl)-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(4-pyrrolidin-1-yl-butyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(4-methylamino-butyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-(3-hydroxy-2-methyl-propoxy)-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-(4-dimethylamino-butoxy)-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-[4-(4-methyl-piperazin-1-yl)-butyl]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(4-pyrrolidin-1-yl-butoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-[4-(3,5-dimethyl-piperazin-1-yl)-butoxy]-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-[3-(4-methyl-piperazin-1-yl)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
3-[4-(2-Chloro-phenyl)-9-hydroxy-1,3-dioxo-8-(3-pyrrolidin-1-yl-propoxy)-2,3-dihydro-1H-pyrrolo[3,4-c]carbazol-6-yl]-propionamide;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-[2-(1-methyl-pyrrolidin-2-yl)-ethoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-[4-(4-methyl-piperazin-1-yl)-butoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(4-morpholin-4-yl-butoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Fluoro-6-methoxy-phenyl)-9-hydroxy-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(2-methyl-3-pyrrolidin-1-yl-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-(3-hydroxy-2,2-dimethyl-propoxy)-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazole-8-carboxylic acid;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazole-8-carboxylic acid amide;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazole-8-carboxylic acid (2-pyrrolidin-1-yl-ethyl)-amide;
3-[4-(2-Chloro-phenyl)-8-(3-dimethylamino-propoxy)-9-hydroxy-1,3-dioxo-2,3-dihydro-1H-pyrrolo[3,4-c]carbazol-6-yl]-propionamide;
4-(2-Chloro-phenyl)-8-[3-(ethyl-propyl-amino)-propylsulfanyl]-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
9-Hydroxy-6-methyl-4-phenyl-8-(3-pyrrolidin-1-yl-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
N-[4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazole-8-carbonyl]-methanesulfonamide;
2-Dimethylamino-ethanesulfonic acid[4-(2-chloro-phenyl)-9-hydroxy-6-methyl-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazole-8-carbonyl]-amide;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazole-8-carboxylic acid dimethylamide;
4-(2-Chloro-phenyl)-9-hydroxy-8-(3-morpholin-4-yl-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(2-pyrrolidin-1-yl-ethoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
8-(3-Amino-propoxy)-4-(2-chloro-phenyl)-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione hydrochloride salt;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(2-methyl-3-pyrrolidin-1-yl-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-[3-(4-methyl-piperazin-1-yl)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-(3-pyrrolidin-1-yl-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(2-morpholin-4-yl-ethoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-[2-(4-methyl-piperazin-1-yl)-ethoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-(3-hydroxy-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazole-8-carboxylic acid (2-dimethylamino-ethyl)-methyl-amide;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazole-8-carboxylic acid (1-ethyl-pyrrolidin-2-ylmethyl)-amide;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazole-8-carboxylic acid (3-diethylamino-propyl)-amide;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(1H-tetrazol-5-yl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazole-8-carboxylic acid[2-(1-methyl-pyrrolidin-2-yl)-ethyl]-amide;
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-{3-[(2-hydroxy-ethyl)-methyl-amino]-propoxy}-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-{3-[(2-hydroxy-ethyl)-methyl-amino]-propoxy}-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-(3-piperidin-1-yl-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(3-piperidin-1-yl-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
8-[3-(Benzyl-methyl-amino)-propoxy]-4-(2-chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
8-[3-(Benzyl-methyl-amino)-propoxy]-4-(2-chloro-phenyl)-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-[3-(4-pyridin-2-yl-piperazin-1-yl)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-[3-(4-pyridin-2-yl-piperazin-1-yl)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-(3-dipentylamino-propoxy)-9-hydroxy-6-(2-hydroxy-ethyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-(3-dipentylamino-propoxy)-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-{3-[(2-dimethylamino-ethyl)-methyl-amino]-propoxy}-9-hydroxy-6-(2-hydroxy-ethyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-{3-[(2-dimethyl amino-ethyl)-methyl-amino]-propoxy}-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-[3-(3-hydroxy-pyrrolidin-1-yl)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-[3-(3-hydroxy-pyrrolidin-1-yl)-propoxy]-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-[3-(cyclohexyl-methyl-amino)-propoxy]-9-hydroxy-6-(2-hydroxy-ethyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-[3-(cyclohexyl-methyl-amino)-propoxy]-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-[3-(2-methyl-piperidin-1-yl)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-[3-(2-methyl-piperidin-1-yl)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-[3-(2-hydroxymethyl-piperidin-1-yl)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-[3-(2-hydroxymethyl-piperidin-1-yl)-propoxy]-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-[3-(methyl-pyridin-3-ylmethyl-amino)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-[3-(methyl-pyridin-3-ylmethyl-amino)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-[3-(2-hydroxymethyl-pyrrolidin-1-yl)-propoxy]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-8-[3-(2-hydroxymethyl-pyrrolidin-1-yl)-propoxy]-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-[3-(ethyl-methyl-amino)-propoxy]-9-hydroxy-6-(2-hydroxy-ethyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-[3-(ethyl-methyl-amino)-propoxy]-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-(3-dipropylamino-propoxy)-9-hydroxy-6-(2-hydroxy-ethyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-(3-dipropylamino-propoxy)-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-(3-diethylamino-propoxy)-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
8-{3-[Bis-(3-methyl-butyl)-amino]-propoxy}-4-(2-chloro-phenyl)-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-[3-(2,6-dimethyl-piperidin-1-yl)-propoxy]-9-hydroxy-6-(2-hydroxy-ethyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-[3-(2,6-dimethyl-piperidin-1-yl)-propoxy]-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
9-Hydroxy-6-(2-hydroxy-ethyl)-4-phenyl-8-(3-pyrrolidin-1-yl-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-(3-dicyclohexylamino-propoxy)-9-hydroxy-6-(2-hydroxy-ethyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
trifluoro-acetic acid salt;
4-(2-Chloro-phenyl)-8-(3-diisopropylamino-propoxy)-9-hydroxy-6-(2-hydroxy-ethyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
trifluoro-acetic acid salt;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazole-8-sulfonic acid (2-pyrrolidin-1-yl-ethyl)-amide;
4-(2-Chloro-phenyl)-8-(3-cyclohexylamino-propoxy)-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(3-pyrrolidin-1-yl-propane-1-sulfinyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(3-pyrrolidin-1-yl-propane-1-sulfonyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-(4-pyrrolidin-1-yl-butyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-(4-morpholin-4-yl-butyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-9-hydroxy-6-(2-hydroxy-ethyl)-8-[4-(4-methyl-piperazin-1-yl)-butyl]-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
4-(2-Chloro-phenyl)-8-[3-(ethyl-propyl-amino)-butoxy]-9-hydroxy-6-methyl-6H-pyrrolo[3,4-c]carbazole-1,3-dione;
and
4-(2-Chloro-phenyl)-9-hydroxy-6-methyl-8-(1-methyl-3-pyrrolidin-1-yl-propoxy)-6H-pyrrolo[3,4-c]carbazole-1,3-dione.

105 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/424,228Filed 25 Apr 2003 · us provisional application
Priority: 26 Apr 2002
Granted: 22 Aug 2006
Term ends: Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D 209/88
Carbazoles; Hydrogenated carbazoles: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to…
C07D 491/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D
Heterocyclic compounds

Family

Application60/375,806Us provisional application · filed 26 Apr 2002
US 7,094,798 B1This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound of Formula I

wherein
each dashed line represents an optional bond;
R1 is
an aryl optionally substituted with up to five substituents selected from halogen, alkyl, haloalkyl, hydroxyl, nitro, cyano, C(O)R3, OR3, S(O)mR3, NR3R4, OC(O)R3, NR3(CO)OR4, CH2NR3R4, CH2OR3, COOR3, CONR3R4, NR3COR4, SO2NR3R4, CONHSO2R3, NR3S(O)mR4 NHCONR3R4, NR3CONHR4;
m is 0–2;
X is hydrogen or halogen;
Y1 is NR10;
R9 is hydroxyl;
r is 0–6;
R2, R7, R8 and R10 are in each instance independently selected from ((CR5R6)nT)a(CR11R12)b)-Z wherein the sum n, a and b is in each instance less than 10;
T may be absent, or, when present, is in each instance independently selected from O, CONR3, CONHSO2, S(O)m, NR3, NR3—O, O—S(O)m, S(O)m—O, NR3—S(O)2, or S(O)2—NR3;
n is in each instance independently 0–6;
a is in each instance independently 0–6;
b is in each instance independently 0–6;
Z is selected from hydrogen, halogen, alkyl, haloalkyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, cyano, nitro, hydroxy, C(O)R3, CONHSO2R3, OR3, S(O)mR3, OSO2R3, NR3R4, CO2R3, CONR3R4, NR3COR4, SO2NR3R4, OPO(OR3)(OR4), CH═CR3R4, CCR3, (C═NR3)NHR4, NH(C═NR3)NHR4, NH(C═NH)NR3R4, wherein the alkyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl group may be substituted with up to four groups independently selected from halogen, alkyl, hydroxyl, nitro, cyano, OR3, S(O)mR3, NR3R4, OC(O)R3, NR3(CO)OR4, C(O)R3, COOR3, CONR3R4, NR3COR4, SO2NR3R4, CONHSO2R3, NR3S(O)mR4, CH2NR3R4, CH2OR3, NHCONR3R4, NR3CONHR4;
R5, R6, R11 and R12 are in each instance independently selected from hydrogen, hydroxyl, alkyl, haloalkyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, heterocyclyl, halogen, cyano, nitro, CH2NR3R4, CH2OR3, C(O)R3, OR3, S(O)mR3, NR3R4, COOR3, CONR3R4, SO2NR3R4, NHCONR3R4, NR3CONHR4;
wherein the alkyl, haloalkyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl group may be substituted with up to four groups independently selected from halogen, alkyl, hydroxyl, nitro, cyano, OR3, S(O)mR3, NR3R4, OC(O)R3, NR3(CO)OR4, C(O)R3, COOR3, CONR3R4, NR3COR4, SO2NR3R4, CONHSO2R3, NR3S(O)mR4, NHCONR3R4, NR3CONHR4;
R5 and R6 or R11 and R12 together with the carbon atom to which they are attached may form a carbonyl group;
or together with the carbon or heteratom to which they are attached may form a cycloalkyl or heterocyclyl group, said carbonyl, cycloalkyl or heterocyclyl group may be substituted with up to four groups independently selected from halogen, hydroxyl, nitro, cyano, alkyl, haloalkyl, alkyl, nitro, cyano, OR3, S(O)mR3, NR3R4, OC(O)R3, NR3(CO)OR4, C(O)R3, COOR3, CONR3R4, NR3COR4, S(O)2NR3R4, CONHSO2R3, NR3S(O)mR4, NHCONR3R4, NR3CONHR4;
R3, R4 are independently selected from hydrogen, alkyl, haloalkyl or a substituted or unsubstituted carbocyclic group selected from cycloalkyl, cycloalkenyl, heterocyclyl, aryl, and heteroaryl, wherein the said alkyl, or a substituted group may be substituted with up to 4 groups selected from halogen, hydroxyl, nitro, cyano, alkyl, haloalkyl, alkyloxy, carboxy, COOH, CONH2, NHCOCH3, N(CH3)2, NHCH3, thiomethyl, thioethyl, SOCH3, SO2CH3;
R3 and R4 together with the carbon atom or heteroatom to which they are attached may form a cycloalkyl or heterocyclyl group substituted with up to four groups independently selected from halogen, hydroxyl, nitro, cyano, alkyl, haloalkyl, alkyloxy, formyl, carboxy, acetyl, CH2NH2, CH2OH, COOH, CONH2, NHCOCH3, N(CH3)2, thiomethyl, thioethyl, SOCH3, SO2CH3, alkoxycarbonyl, alkylcarbonyl, alkynylamino, aminoalkyl, aminoalkylcarbonyl, amino, mono- or dialkylamino, or
R3 and R4 together with the nitrogen to which they are attached may form a heterocyclic ring containing 3–8 members, up to four of which members are optionally carbonyl groups or heteroatoms independently selected from oxygen, sulfur, S(O), S(O)2, and nitrogen, wherein the carbocyclic group is unsubstituted or substituted with up to four groups independently selected from halogen, hydroxy, hydroxyalkyl, alkyl, haloalkyl, alkoxy, alkoxycarbonyl, alkylcarbonyl, alkynylamino, aminoalkyl, aminoalkylcarbonyl, amino, mono- or dialkylamino.

19 more elements

Facts

Application

10/424,228Filed 25 Apr 2003 · us provisional application

Priority

26 Apr 2002

Granted

22 Aug 2006

Term ends

Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D 209/88
Carbazoles; Hydrogenated carbazoles: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to…
C07D 491/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D
Heterocyclic compounds