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Claims for Patent: 4,820,738

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Claims for Patent: 4,820,738

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 inducing regression and/or palliation of cancer diseases in mammals.
Inventor(s): Murdock; Keith C. (Pearl River, NY), Durr; Frederick E. (Ridgewood, NJ)
Assignee: American Cyanamid Company (Stamford, CT)
Application Number:06/823,265
Patent Claims: 1. The method of inhibiting growth of solid tumors in a mammal which comprises administering to said mammal an amount effective to inhibit growth of solid tumors of a compound capable of inhibiting growth of solid tumors, said compound selected from the group consisting of those of the formulae: ##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; the leuco bases and tautomers thereof; and the pharmacologically acceptable acid-addition salts thereof; said solid tumors being those that are susceptible to growth inhibition in said mammal by administration of said compound.

2. The method of claim 1 wherein Q is --CH.sub.2 CH.sub.2 --.

3. The method of claim 2 wherein said compound is selected from the group:

a. Leuco-1,4-bis[(2-dimethylaminoethyl)amino]-5,8-dihydroxyanthraquinone;

b. 1,4-Bis[(2-dimethylaminoethyl)amino]-5,8-dihydroxyanthraquinone;

c. Leuco-1,4-bis[(2-diethylaminoethyl)amino]-5,8-dihydroxyanthraquinone;

d. 1,4-Bis[(2-diethylaminoethyl)amino]-5,8-dihydroxyanthraquinone;

e. the dihydrochloride salt of 1,4-bis[2-(2-hydroxyethylamino)ethylamino]-5,8-dihydroxyanthraquininone; and

f. 1,4-Bis(2-aminoethylamino)-5,8-dihydroxyanthraquinone or its dihydrochloride salt.

4. The method of inducing regression of leukemia cell growth in a mammal which comprises administering to said mammal an amount effective to induce regression of leukemia cell growth of a compound capable of inducing regression of leukemia cell growth, said compound selected from the group consisting of those of the formulae: ##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; the leuco bases and tautomers thereof; and the pharmacologically acceptable acid-addition salts thereof.

5. The method of claim 4 wherein Q is --CH.sub.2 CH.sub.2 --.

6. The method of claim 5 wherein said compound is 1,4-bis(2-aminoethylamino)-5,8-dihydroxyanthraquinone or its dihydrochloride salt.

7. The method of claim 4 wherein said compound is selected from the group consisting of:

a. Leuco-1,4-bis[(2-dimethylaminoethyl)amino]-5,8-dihydroxyanthraquinone;

b. 1,4-Bis[(2-dimethylaminoethyl)amino]-5,8-dihydroxyanthraquinone;

c. Leuco-1,4-bis[(2-diethylaminoethyl)amino]-5,8-dihyroxyanthraquinone;

d. 1,4-Bis[(2-diethylaminoethyl)amino]-5,8-dihydroxyanthraquinone;

e. the dihydrochloride salt of 1,4-Bis[2-(2-hydroxyethylamino)ethylamino]-5,8-dihydroxyanthraquinone.

8. The method of claim 7 wherein said compound is Leuco-1,4-bis[(2-dimethylaminoethyl)amino]-5,8-dihydroxyanthraquinone.

9. The method of claim 7 wherein said compound is 1,4-bis[(2-dimethylaminoethyl)amino]-5,8-dihydroxyanthraquinone.

10. The method of claim 7 wherein said compound is Leuco-1,4-bis[(2-diethylaminoethyl)amino]-5,8-dihyroxyanthraquinone.

11. The method of claim 7 wherein said compound is 1,4-bis[(2-diethylaminoethyl)amino]-5,8-dihydroxyanthraquinone.

12. The method of claim 7 wherein said mammal is a mouse.
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