# US 5,348,946 A · Heteroanthracycline antitumor analogs

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- Number: US 5,348,946 A
- Document ID: US5348946A
- Status: Granted
- Kind: A
- Application number: 07/751,092
- Filed: 1991-08-28
- Granted: 1994-09-20
- Earliest claimed: 1991-02-28
- Assignees: Biochem Immunosystems, Inc.
- Inventors: Giorgio G. Attardo; Bernard Belleau, deceased
- Web page: https://patentgrep.com/patent/US5348946A

## CPC

- C07D 495/04: Ortho-condensed systems
- C07C 45/60: in six-membered rings
- C07C 47/575: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups
- C07C 313/08: Sulfenic acids; Derivatives thereof
- C07D 319/06: not condensed with other rings
- C07D 333/72: Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
- C07H 17/00: Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

Heterocyclic antitumor compounds are described, which are useful in the treatment of cancer and tumors in vitro, such as breast cancer, leukemia, lung cancer, colon cancer, ovarian cancer, renal cancer, CNS cancer and melanoma. Pharmaceutical compositions and method of preparing the compounds are also described.

## Claims

### Claim 1

A compound of the formula ##STR12## X.sub.1 is C.dbd.O; X.sub.2 is S;
X.sub.3 is selected from the group consisting of
S and
SO.sub.2
R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.8 are independently selected from group consisting of
hydrogen,
C.sub.1-16 alkyl, and
C.sub.1-16 alkoxy,
R.sub.7 is hydrogen;
R.sub.6 is a monosaccharide of the formula ##STR13## wherein R.sub.9 and R.sub.10 are each hydrogen R.sub.11 is selected from the group consisting of
amino, and
trifluoro C.sub.1-16 acylated amino; and
R.sub.12 is selected from the group consisting of
hydrogen,
hydroxyl or its tetrahydropranyl ether,
halogen, and
benzoate which may be unsubstituted or substituted by nitro,
inclusive of the 1S and 1R isomers and the pharmaceutically acceptable salts thereof.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein
R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.8 are independently selected from the group consisting of
hydrogen, and
C.sub.1-4 alkoxy,
R.sub.6 is a monosaccharide of the formula ##STR14## wherein R.sub.9 and R.sub.10 are as defined in claim 1;
R.sub.11 is selected from the group consisting of
amino, and
trifluoro C.sub.1-8 acylated amino, and
R.sub.12 is as defined in claim 1.

### Claim 3 (depends on 1)

A compound according to claim 1, wherein
R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.8 are independently selected from the group consisting of hydrogen methoxy.

### Claim 4 (depends on 1)

A compound according to claim 1, wherein
R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.8 are each hydrogen.

### Claim 5 (depends on 1)

The compound of claim 1 which is (1R) 1-(4'-O-p-nitrobenzoyl-N-trifluoroacyldaunosamine)-4,11-dimethoxy-5-oxo-5- H-1,3-dihydrothioxantheno [2,3-c] thiophene-2,2-dioxide (37) .

### Claim 6 (depends on 1)

The compound of claim 1 which is (1S) 1-(4'-O-p-nitrobenzoyl-N-trifluoroacyldaunosamine)-4,11-dimethoxy-5-oxo-5- H-1,3-dihydrothioxantheno [2,3-c] thiophene-2,2-dioxide (36).

### Claim 7 (depends on 1)

The compound of claim 1 which is (1R) 1-(N-trifluoroacyldaunosamine)-4,11-dimethoxy-5-oxo-5-H-1,3-dihydrothioxan theno [2.3-c] thiophene-2,2-dioxide (40) .

### Claim 8 (depends on 1)

The compound of claim 1 which is (1S) 1-(N-trifluoroacyldaunosamine)-4,11-dimethoxy-5-oxo-5-H-1,3-dihydrothioxan theno [2,3-c] thiophene-2,2-dioxide (38) .

### Claim 9 (depends on 1)

The compound of claim 1 which is (1R) 1-daunosamine-4-11-dimethoxy-5-oxo-5-H-1,3-dihydrothioxantheno [2,3-c] thiophene-2,2-dioxide (41) .

### Claim 10 (depends on 1)

The compound of claim 1 which is (1S) 1-daunosamine-4-11-dimethoxy-5-oxo-5-H-1,3-dihydrothioxantheno [2,3-c] thiophene-2,2-dioxide (39) .

### Claim 11 (depends on 1)

A compound of the formula ##STR15## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are as defined in claim 1.

### Claim 12 (depends on 1)

A pharmaceutical composition, comprising an effective amount of at least one compound according to claim 1 and a pharmaceutically acceptable carrier.

### Claim 13 (depends on 2)

A pharmaceutical composition, comprising an effective amount of at least one compound according to claim 2 and a pharmaceutically acceptable carrier.

### Claim 14 (depends on 3)

A pharmaceutical composition, comprising an effective amount of at least one compound according to claim 3 and a pharmaceutically acceptable carrier.

### Claim 15 (depends on 4)

A pharmaceutical composition, comprising an effective amount of at least one compound according to claim 4 and a pharmaceutically acceptable carrier.

### Claim 16 (depends on 5)

A pharmaceutical composition, comprising an effective amount of a compound according to claim 5, and a pharmaceutically acceptable carrier.

### Claim 17 (depends on 6)

A pharmaceutical composition, comprising an effective amount of a compound according to claim 6, and a pharmaceutically acceptable carrier.

### Claim 18 (depends on 7)

A pharmaceutical composition, comprising an effective amount of a compound according to claim 7, and a pharmaceutically acceptable carrier.

### Claim 19 (depends on 8)

A pharmaceutical composition, comprising an effective amount of at least one compound according to claim 8, and a pharmaceutically acceptable carrier.

### Claim 20 (depends on 9)

A pharmaceutical composition, comprising an effective amount of at least one compound according to claim 9, and a pharmaceutically acceptable carrier.

### Claim 21 (depends on 10)

A pharmaceutical composition, comprising an effective amount of at least one compound according to claim 10, and a pharmaceutically acceptable carrier.

### Claim 22 (depends on 11)

A pharmaceutical composition, comprising an effective amount at least one compound as claimed in claim 11, and a pharmaceutically acceptable carrier.