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Generated: August 19, 2017

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Title: Novel 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 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 (Wayne, NJ)
Filing Date:Apr 27, 1987
Application Number:07/042,779
Claims:1. A compound selected from the group consisting of those of the formula: ##STR3## wherein R is hydrogen, alkyl (C.sub.1 -C.sub.3), trifluoromethyl, acetyl, ethoxy or carbomethoxy; the leuco bases and tautomers thereof; and the pharmacologically acceptable acid-addition salts thereof.

2. The compound according to claim 1 wherein R is hydrogen; N,N'-[10-dihydro-5,8-dihydroxy-9, 10-dioxo-1,4-anthracenediyl)bis(imino-2, 1-ethanediyl)]bis-formamide.

3. The compound according to claim 1 wherein R is methyl; N,N'-[(9,10-dihydro-5,8-dihydroxy-9, 10-dioxo-1,4-anthracenediyl)bis(imino-2, 1-ethanediyl)]bis-acetamide.

4. The compound according to claim 1 wherein R is trifluoromethyl; N,N'-[(9,10-dihydro-5,8-dihydroxy-9,10-dioxo-1,4-anthracenediyl)bis-(imino -2,1-ethanediyl)]bis-trifluoroacetamide.

5. The compound according to claim 1 wherein R is acetyl; N,N'-[(9,10-dihydro-5,8-dihydroxy-9,10-dioxo-1,4-anthracenediyl)bis(imino- 2,1-ethanediyl)]bis-(2-oxopropanamide).

6. The compound according to claim 1 wherein R is ethoxy;[(9,10-dihydro-5,8-dihydroxy-9,10-dioxo-1,4-anthracenediyl)bis(imin o-2,1-ethanediyl)]-bis-(carbamic acid)diethyl ester.

7. The compound according to claim 1 wherein R is carbomethoxy; 2,2'-[(9,10-dihydro-5,8-dihydroxy-9,10-dioxo-1,4-anthracenediyl)bis(imino- 2,1-ethanediylimino)]bis(2-oxoacetic acid)dimethyl ester.

8. A compound selected from the group consisting of 1,4-bis[2-[N-(2-hydroxyethyl)trifluoroacetamido]ethylamino]-5,8-dihydroxya nthraquinone, the leuco base and tautomer thereof, and the pharmacologically acceptable acid-addition salts thereof.

9. A compound selected from the group consisting of N,N'-[5,8-dihydroxy-1,4-anthraquinonylene-bis(iminoethylene)]bis[N-2-hydro xyethylacetamide-2,2'-diacetate],the leuco base and tautomer thereof, and the pharmacologically acceptable acid-addition salts thereof.

10. A compound selected from the group consisting of N,N'-(5,8-dihydroxy-1,4-anthraquinonylene)bis[2,2,2-trifluoro-N-[2-(2,2,2- trifluoro-N-2-hydroxyethylacetamido)ethyl]acetamide]tetrakis(tri-fluoroacet ate)(tetraester), the leuco base and the tautomer thereof, and the pharmacologically acceptable acid-addition salts thereof.
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