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Claims for Patent: 4,197,249

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Claims for Patent: 4,197,249

Title: 1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones 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:05/923,602
Patent Claims: 1. 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.

2. 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 atoms 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; the tautomers thereof; and the pharmacologically acceptable acid-addition salts thereof.

3. An acid-addition salt according to claim 1 wherein the acid is sulfuric acid.

4. An acid-addition salt according to claim 2 wherein the acid is phosphoric acid.

5. An acid-addition salt according to claim 1 wherein the acid is hydrochloric acid.

6. An acid-addition salt according to claim 2 wherein the acid is hydrobromic acid.

7. An acid-addition salt according to claim 1 wherein the acid is sulfamic acid.

8. An acid-addition salt according to claim 2 wherein the acid is citric acid.

9. An acid-addition salt according to claim 1 wherein the acid is lactic acid.

10. An acid-addition salt according to claim 2 wherein the acid is malic acid.

11. An acid-addition salt according to claim 1 wherein the acid is succinic acid.

12. An acid-addition salt according to claim 2 wherein the acid is tartaric acid.

13. An acid-addition salt according to claim 1 wherein the acid is acetic acid.

14. An acid-addition salt according to claim 2 wherein the acid is benzoic acid.

15. An acid-addition salt according to claim 1 wherein the acid is gluconic acid.

16. An acid-addition salt according to claim 2 wherein the acid is ascorbic acid.

17. The compound 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.

18. The compound 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.

19. The compound 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.

20. The compound 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.

21. The compound 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.

22. The compound 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.

23. The compound 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.

24. The compound 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.

25. A compound according to claim 24 in its pharmacologically acceptable acid-addition salt form.

26. The compound 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.

27. The compound 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.

28. The compound according to claim 2 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 compound according to claim 2 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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