Claims
- 1. A compound according to the formula (I): ##STR13## wherein R is hydrogen or hydroxy;
- Y is carbon and X is nitrogen;
- A and B are the same or different and are selected from the group consisting of:
- C.sub.1 -C.sub.10 alkyl or phenylalkyl;
- C.sub.2 -C.sub.10 alkyl having one or two substituents selected from the group consisting of OR.sub.1 and NR.sub.2 R.sub.3 ; and
- C.sub.2 -C.sub.10 alkyl interrupted by one or two oxygen atoms or by one --NR.sub.4 -- group, said C.sub.2 -C.sub.10 alkyl optionally substituted by one or two hydroxy or NR.sub.2 R.sub.3 groups;
- R.sub.1 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl, phenylalkyl, --S(O.sub.2)R.sub.5, C.sub.2 -C.sub.6 alkyl optionally substituted by NR.sub.2 R.sub.3 ;
- R.sub.2 and R.sub.3 may be the same or different and are selected from the group consisting of hydrogen, C.sub.1 -C.sub.10 alkyl, phenylalkyl, phenyl, C.sub.2 -C.sub.10 alkyl substituted with one or two hydroxy (OH) groups, or R.sub.2 and R.sub.3 taken together with the nitrogen atom to which they are attached form an ethyleneimine ring or a 5- or 6-member aromatic or non-aromatic heterocyclic ring which optionally contains another heteroatom such as sulfur, oxygen or nitrogen;
- R.sub.4 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 hydroxyalkyl, C.sub.2 -C.sub.10 alkyl substituted by NR.sub.2 R.sub.3, phenylalkyl, phenyl;
- R.sub.5 is selected from the group consisting of C.sub.1 -C.sub.10 alkyl, phenylalkyl;
- as free bases and their salts with pharmaceutically acceptable acids.
- 2. A compound according to claim 1 wherein said heterocyclic ring is selected from the group consisting of 1-imidazolyl, 1-pyrrolyl, 1-tetrahydropyrrolyl, 1-pyrazolyl, 4-morpholinyl, 1-piperidinyl, 1-piperazinyl, 1-(4-methyl)-piperazinyl, and 1-(4-benzyl)-piperazinyl.
- 3. A compound according to claim 1 wherein R is hydrogen.
- 4. A compound according to claim 1 wherein R is hydrogen and A and B are independently are selected from the group consisting of: --(CH.sub.2).sub.p --NH.sub.2 wherein p is the integer 2 or 3; --(CH.sub.2).sub.p --NR.sub.2 R.sub.3 wherein p is as above defined and R.sub.2 and R.sub.3 are methyl; --(CH.sub.2).sub.p --NR.sub.2 R.sub.3 wherein p is as above defined and R.sub.2 is hydrogen and R.sub.3 is methyl; --(CH.sub.2).sub.p --OH wherein p is as above defined; --(CH.sub.2).sub.p --NH--(CH.sub.2).sub.q --OH wherein p and q are independently an integer selected from group consisting of 2 or 3.
- 5. A compound of claim 1 selected from the group consisting of 2-[2-[(2-hydroxyethyl)amino]ethyl]-5-[[2-[(2-hydroxyethyl)amino]ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one;
- 2-[2-[(2-hydroxyethyl)amino]ethyl]-5-[(3-aminopropyl) amino]isoquino[8,7,6-cd]indazole-6(2H)-one;
- 2-[2-[(2-hydroxyethyl)amino]ethyl]-5-[(2-aminoethyl) amino]isoquino[8,7,6-cd]indazole-6(2H)-one;
- 2-[2-[(2-hydroxyethyl)amino]ethyl]-5-[[2-(methylamino) ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one;
- 2-[2-[(2-hydroxyethyl)amino]ethyl]-5-[[2-(dimethylamino) ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one;
- 2-[2-[(2-hydroxyethyl)amino]ethyl]-5-[[2-[(2-hydroxyethyl) amino]ethyl]amino]isoquino[5,6,7-cd)indazole-6(2H)-one;
- 2-[2-[(2-hydroxyethyl)amino]ethyl]-5-[(3-aminopropyl) amino]isoquino[5,6,7-cd)indazole-6(2H)-one;
- 2-[2-[(2-hydroxyethyl)amino]ethyl]-5-[(2-aminoethyl) amino]isoquino[5,6,7-cd]indazole-6(2H)-one;
- 2-[2-[(2-hydroxyethyl)amino]ethyl]-5-[[2-(methylamino) ethyl]amino]isoquino [5,6,7-cd]indazole-6(2H)-one;
- 2-[2-[(2-hydroxyethyl)amino]ethyl]-5-[[2-(dimethylamino) ethyl]amino]isoquino [5,6,7-cd]indazole-6(2H)-one;
- 5-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-2-[2-(dimethylamino)ethyl]isoquino [8,7,6-cd]indazole-6(2H)-one;
- 5-[(3-aminopropyl)amino]-2-[2-(dimethylamino)ethyl]isoquino[8,7,6-cd]indazole-6(2H)-one;
- 5-[(2-aminoethyl)amino]-[2-[2-(dimethylamino)ethyl]isoquino [8,7,6-cd]indazole-6(2H)-one;
- 5-[[2-(methylamino)ethyl]amino]-2-[2-(dimethylamino) ethyl]isoquino [8,7,6-cd]indazole-6(2H)-one;
- 5-[[2-(dimethylamino)ethyl]amino]-2-[2-(dimethylamino) ethyl]isoquino [8,7,6-cd]indazole-6(2H)-one;
- 5-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-2-[2-(dimethylamino)ethyl]isoquino[5,6,7-cd]indazole-6(2H)-one;
- 5-[(3-aminopropyl)amino]-2-[2-(dimethylamino)ethyl]isoquino [5,6,7-cd]indazole-6(2H)-one;
- 5-[(2-aminoethyl)amino]-[2-(dimethylamino)ethyl]isoquino [5,6,7-cd]indazole-6(2H)-one;
- 5-[[2-(methylamino)ethyl]amino]-2-[2-(dimethylamino) ethyl]isoquino [5,6,7-cd]indazole-6(2H)-one;
- 5-[[2-(dimethylamino)ethyl]amino]-2-[2-(dimethylamino) ethyl]isoquino [5,6,7-cd]indazole-6(2H)-one;
- 2-[2-aminoethyl]-5-[[2-[(2-hydroxyethyl)amino]ethyl]amino]isoquino [8,7,6-cd]indazole-6(2H)-one;
- 2-[2-aminoethyl]-5-[(3-aminopropyl)amino]isoquino [8,7,6-cd] indazole-6(2H)-one;
- 2-[2-aminoethyl)-5-[(2-aminoethyl)amino]isoquino [8,7,6-cd] indazole-6(2H)-one;
- 2-[2-aminoethyl]-5-[[2-(methylamino)ethyl]amino]isoquino [8,7,6-cd]indazole-6(2H)-one;
- 2-[2-aminoethyl]-5-[[2-(dimethylamino)ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one;
- 2-[3-aminopropyl)-5-[[2-[(2-hydroxyethyl)amino]ethyl]amino]isoquino [8,7,6-cd]indazole-6(2H)-one;
- 2-[3-aminopropyl]-5-[(3-aminopropyl)amino]isoquino [8,7,6-cd]indazole-6(2H)-one;
- 2-[3-aminopropyl]-5-[(2-amino)ethyl)amino]isoquino [8,7,6-cd]indazole-6(2H )-one;
- 2-[3-aminopropyl]-5-[[2-(methylamino)ethyl]amino]isoquino [8,7,6-cd]indazole-6(2H )-one;
- 2-[3-aminopropyl]-5-[[2-(dimethylamino)ethyl]amino]isoquino [8,7,6-cd]indazole-6(2H)-one;
- 5-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-2-[3-aminopropyl] isoquino [5,6,7-cd]indazole-6(2H)-one;
- 5-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-2-[2-aminoethyl]isoquino [5,6,7-cd) indazole-6(2H)-one;
- 2-[(2-methylamino)ethyl]-5-[[2-[(2-hydroxyethyl)amino]ethyl]amino]isoquino [8,7,6-cd]indazole-6(2H)-one;
- 2-[(2-methylamino)ethyl]-5-[(3-aminopropyl)amino]isoquino [8,7,6-cd]indazole-6(2H)-one;
- 2-[(2-methylamino)ethyl]-5-[(2-aminoethyl)amino]isoquino [8,7,6-cd]indazole-6(2H )-one;
- 2-[(2-methylamino)ethyl]-5-[[2-(methylamino)ethyl]amino]]isoquino [8,7,6-cd]indazole-6(2H)-one;
- 2-[(2-methylamino)]ethyl]-5-[[2-(dimethylamino)ethyl]amino]isoquino [8,7,6-cd]indazole-6(2H)-one;
- 2-[(2-methylamino)ethyl]-5-[[2-[(2-hydroxyethyl)amino]ethyl]amino]isoquino [5,6,7-cd]indazole-6(2H)-one;
- 2-[(2-methylamino)ethyl]-5-[(3-aminopropyl)amino]isoquino [5,6,7-cd]indazole-6(2H)-one;
- 2-[(2-methylamino)ethyl]-5-[(2-aminoethyl)amino]isoquino [5,6,7-cd)indazole-6(2H)-one;
- 2-[(2-methylamino)ethyl]-5-[[2-(methylamino)ethyl]amino]isoquino [5,6,7-cd]indazole-6(2H)-one;
- 2-[(2-methylamino)ethyl]-5-[[2-(dimethylamino)ethyl]amino]isoquino [5,6,7-cd]indazole-6(2H)-one;
- 2-methyl-5-[[2-(dimethylamino)ethyl]amino]isoquino [8,7,6-cd]indazole-6(2H)-one; and
- 2-methyl-5-[[2-(dimethylamino)ethyl]amino]isoquino[5,6,7-cd]indazole-6(2H)-one, as their free bases and their salts with pharmaceutically acceptable salts.
- 6. A pharmaceutical composition suitable for the treatment of tumors in a patient comprising a compound according to claim 1 and a pharmaceutically acceptable diluent or excipient.
- 7. A method of treatment of tumors susceptible to azaanthrapyrazole treatment in a mammal requiring such treatment comprising administering to the mammal an effective anti-tumor amount of a compound according to claim 1.
Parent Case Info
This application is a cip of Ser. No. 07/941,607 filed Sep. 8, 1992, now abandoned.
Foreign Referenced Citations (1)
Number |
Date |
Country |
WO9215300 |
Sep 1992 |
WOX |
Continuations (1)
|
Number |
Date |
Country |
Parent |
941607 |
Sep 1992 |
|