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Claims for Patent: 4,278,689

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Claims for Patent: 4,278,689

Title: 1,4-Bis(substituted-amino)-5,8-dihydroxy-anthraquinones and leuco bases thereof
Abstract:This disclosure describes symmetrical 1,4-bis(substituted-amino)-5,8-dihydroxyanthraquinones useful as chelating agents and for inhibiting the growth of transplanted mouse tumors.
Inventor(s): Murdock; Keith C. (Pearl River, NY), Durr; Frederick E. (Ridgewood, NJ)
Assignee: American Cyanamid Company (Stamford, CT)
Application Number:06/063,285
Patent Claims: 1. A pharmaceutical composition in dosage unit form comprising from about one to about 30 mg. of a compound selected from the group consisting of those of the formula: ##STR11## wherein Q is a divalent moiety selected from the group consisting of those of the formulae: ##STR12## wherein n is an integer from 2 to 4, inclusive; R.sub.1 and R.sub.2 are each individually selected from the group consisting of hydrogen, alkyl having from 1 to 4 carbon atoms and monohydroxyalkyl having from 2 to 4 carbon atoms and wherein the carbon atom alpha to the nitrogen atom may not bear an hydroxy group with the proviso that R.sub.1 and R.sub.2 may not both be hydrogen or alkyl; and the pharmacologically acceptable acid-addition salts thereof; in association with a pharmaceutical carrier.

2. A composition according to claim 1 wherein the compound is a salt of sulfuric acid.

3. A composition according to claim 1 wherein the compound is a salt of hydrochloric acid.

4. A composition according to claim 1 wherein the compound is a salt of sulfamic acid.

5. A composition according to claim 1 wherein the compound is a salt of citric acid.

6. A composition according to claim 1 wherein the compound is a salt of lactic acid.

7. A composition according to claim 1 wherein the compound is a salt of succinic acid.

8. A composition according to claim 1 wherein the compound is a salt of acetic acid.

9. A composition according to claim 1 wherein the compound is a salt of gluconic acid.

10. The composition according to claim 1 wherein Q is ethylene and R.sub.1 and R.sub.2 are both .beta.-hydroxyethyl and in the aromatic free base form.

11. The composition according to claim 1 wherein Q is ethylene, R.sub.1 is hydrogen, and R.sub.2 is .beta.-hydroxyethyl and in the disuccinate salt form.

12. The composition according to claim 1 wherein Q is ethylene, R.sub.1 is hydrogen, and R.sub.2 is .beta.-hydroxyethyl and in the dihydrochloride salt form.

13. The composition according to claim 1 wherein Q is ethylene, R.sub.1 is hydrogen, and R.sub.2 is 3-hydroxypropyl and in the dihydrobromide salt form.

14. The composition according to claim 1 wherein Q is ethylene, R.sub.1 is hydrogen, and R.sub.2 is 2-hydroxypropyl and in the disuccinate salt form.

15. The composition according to claim 1 wherein Q is trimethylene, R.sub.1 is hydrogen, and R.sub.2 is .beta.-hydroxyethyl and in the diacetate salt form.

16. The composition according to claim 1 wherein Q is --CH.sub.2 CH(CH.sub.3)--, R.sub.1 is hydrogen, and R.sub.2 is .beta.-hydroxyethyl and in the dimalate salt form.

17. The composition according to claim 1 wherein Q is ethylene, R.sub.1 is hydrogen, and R.sub.2 is .beta.-hydroxyethyl and in the aromatic free base form.

18. A composition according to claim 17 in its pharmacologically acceptable acid-addition salt form.

19. The composition according to claim 1 wherein Q is ethylene, R.sub.1 is hydrogen, and R.sub.2 is .beta.-hydroxyethyl and in the digluconate salt form.

20. The composition according to claim 1 wherein Q is ethylene, R.sub.1 is hydrogen, and R.sub.2 is .beta.-hydroxyethyl and in the dibenzoate salt form.

21. A pharmaceutical composition in dosage unit form comprising from about one to about 30 mg. of a compound selected from the group consisting of those of the formula: ##STR13## wherein Q is a divalent moiety selected from the group consisting of those of the formulae: ##STR14## wherein n is an integer from 2 to 4, inclusive; R.sub.1 and R.sub.2 are each individually selected from the group consisting of hydrogen, alkyl having from 1 to 4 carbon atoms and monohydroxyalkyl having from 2 to 4 carbon atoms and wherein the carbon atom alpha to the nitrogen atom may not bear an hydroxy group with the proviso that R.sub.1 and R.sub.2 may not both be hydrogen or alkyl; and the pharmacologically acceptable acid-addition salts thereof; in association with a pharmaceutical carrier.

22. A composition according to claim 21 wherein the compound is a salt of phosphoric acid.

23. A composition according to claim 21 wherein the compound is a salt of hydrobromic acid.

24. A composition according to claim 21 wherein the compound is a salt of malic acid.

25. A composition according to claim 21 wherein the compound is a salt of tartaric acid.

26. A composition according to claim 21 wherein the compound is a salt of benzoic acid.

27. A composition according to claim 21 wherein the compound is a salt of ascorbic acid.

28. The composition according to claim 21 wherein Q is ethylene, R.sub.1 is hydrogen, and R.sub.2 is .beta.-hydroxyethyl and in the leuco free base form.

29. The composition according to claim 21 wherein Q is ethylene, R.sub.1 is hydrogen, and R.sub.2 is 2-hydroxypropyl and in the leuco free base form.
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