# US 5,346,917 A · Thioxanthenone antitumor agents

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,346,917 A
- Document ID: US5346917A
- Status: Granted
- Kind: A
- Application number: 08/044,843
- Filed: 1993-04-08
- Granted: 1994-09-13
- Earliest claimed: 1991-06-10
- Assignees: Sterling Winthrop Inc.
- Inventors: Theodore C. Miller; Joseph C. Collins; Kenneth C. Mattes; Mark P. Wentland; Robert B. Perni; Thomas H. Corbett; Joseph W. Guiles
- Web page: https://patentgrep.com/patent/US5346917A

## CPC

- C07F 9/655372: {condensed with carbocyclic rings or carbocyclic ring systems}
- A61P 35/00: Antineoplastic agents
- C07D 335/16: Oxygen atoms, e.g. thioxanthones
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

1-[[(Dialkylamino)alkyl]amino]-4-substituted-thioxanthen-9-ones are disclosed as antitumor agents. Compositions containing the thioxanthenones and methods of treating tumors and cancer in mammals with the thioxanthenones are also disclosed.

## Claims

### Claim 1

A compound of formula ##STR11## wherein n is 2 or 3; R.sup.1 and R.sup.2 are independently lower-alkyl;
Q is CH.sub.2 N(R.sup.4)SO.sub.2 R.sup.7 ;
R.sup.4 is hydrogen, lower-alkyl or Ar;
R.sup.7 is lower-alkyl, or Ar;
R.sup.8 is hydrogen, lower-alkyl, lower-alkoxy, or hydroxy;
and
Ar is phenyl or phenyl substituted with methyl, methoxyl, hydroxy, halogen or nitro, with the proviso that when n is 2, R.sup.1 and R.sup.2 are ethyl, R.sup.8 is hydrogen and Q is CH.sub.2 NHSO.sub.2 Ar, the Ar group cannot be 4-monosubstituted by methyl or halogen;
or a pharmaceutically acceptable acid-addition salt or solvate thereof.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein:
and R.sup.4 is hydrogen or lower-alkyl.

### Claim 3 (depends on 2)

A compound according to claim 2 wherein:
R.sup.8 is hydrogen, lower-alkyl, lower-alkoxy or hydroxy; and Ar is phenyl or phenyl substituted with methyl, methoxyl, halogen or nitro.

### Claim 4 (depends on 3)

A compound according to claim 3 wherein R.sup.8 is hydrogen, lower-alkyl, or lower-alkoxy.

### Claim 5 (depends on 4)

A compound according to claim 4 wherein:
R.sup.7 is lower-alkyl.

### Claim 6 (depends on 5)

A compound according to claim 5 wherein both of R.sup.1 and R.sup.2 are methyl or ethyl, and R.sup.8 is hydrogen or methoxyl.

### Claim 7 (depends on 6)

A compound according to claim 6 wherein n is 2 and both of R.sup.1 and R.sup.2 are ethyl, and R.sup.8 is hydrogen.

### Claim 8 (depends on 4)

A compound according to claim 4 wherein both of R.sup.1 and R.sup.2 are methyl or ethyl, and R.sup.8 is hydrogen or methoxyl.

### Claim 9 (depends on 8)

A compound according to claim 8 wherein n is 2 and both of R.sup.1 and R.sup.2 are ethyl, and R.sup.8 is hydrogen.

### Claim 10 (depends on 9)

N-[[1-[[2-(Diethylamino)ethyl)amino]-9-o xothioxanthen-4-yl]methyl]N-methylmethanesulfonamide according to claim 9.

### Claim 11 (depends on 9)

N-[[1-[[2-(Diethylamino)ethyl)amino]-9-oxothioxanthen-4-yl]methyl]N-met hylmethanesulfonamide according to claim 9.

### Claim 12 (depends on 9)

N-[[1-[[2-(Diethylamino)ethyl]amino]-9- oxothioxanthen-4-yl]methyl]phenylsulfonamide according to claim 9.

### Claim 13

N-[[1-[[2-(Diethylamino)ethyl]amino]-7-bromo-9-oxothioxanthen- 4-yl]methyl]methanesulfonamide.

### Claim 14 (depends on 1)

A pharmaceutical composition which comprises a compound of claim 1 and a pharmaceutically acceptable carrier or diluent.

### Claim 15 (depends on 4)

A pharmaceutical composition which comprises a compound of claim 4 and a pharmaceutically acceptable carrier or diluent.

### Claim 16 (depends on 10)

A pharmaceutical composition which comprises a compound of claim 10 and a pharmaceutically acceptable carrier or diluent.

### Claim 17 (depends on 13)

A pharmaceutical composition which comprises a compound of claim 13 and a pharmaceutically acceptable carrier or diluent.

### Claim 18 (depends on 1)

A method for treating a susceptible tumor in a mammal which comprises administering to said mammal an amount of a compound of claim 1 effective to reduce the size of said tumor.

### Claim 19 (depends on 4)

A method for treating a susceptible tumor in a mammal which comprises administering to said mammal an amount of a compound of claim 4 effective to reduce the size of said tumor.

### Claim 20 (depends on 10)

A method for treating a susceptible tumor in a mammal which comprises administering to said mammal an amount of a compound of claim 10 effective to reduce the size of said tumor.

### Claim 21 (depends on 13)

A method for treating a susceptible tumor in a mammal which comprises administering to said mammal an amount of a compound of claim 13 effective to reduce the size of said tumor.

### Claim 22 (depends on 14)

A method for treating a susceptible cancer in a mammal which comprises administering to a mammal suffering from said cancer a susceptible tumor size-reducing amount of a composition according to claim 14.

### Claim 23 (depends on 15)

A method for treating a susceptible cancer in a mammal which comprises administering to a mammal suffering from said cancer a susceptible tumor size-reducing amount of a composition according to claim 15.

### Claim 24 (depends on 16)

A method for treating a susceptible cancer in a mammal which comprises administering to a mammal suffering from said cancer a tumor size-reducing amount of a composition according to claim 16.

### Claim 25 (depends on 17)

A method for treating a susceptible cancer in a mammal which comprises administering to a mammal suffering from said cancer a tumor size-reducing amount of a composition according to claim 17.