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Claims for Patent: 4,452,745

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Claims for Patent: 4,452,745

Title: 9-Aminoalkylfluorenes
Abstract:Fluorenes bearing a 9-aminoalkyl substituent are useful antiarrhythmic agents. Pharmaceutical formulations containing such compounds are provided, as well as a method of treatment.
Inventor(s): Lacefield; William B. (Indianapolis, IN), Simon; Richard L. (Greenwood, IN)
Assignee: Eli Lilly and Company (Indianapolis, IN)
Application Number:06/426,491
Patent Claims: 1. A compound of the formula ##STR12## wherein: R.sup.1 is hydroxy, cyano, or CONR.sup.4 R.sup.5 in which R.sup.4 and R.sup.5 independently are hydrogen or C.sub.1 -C.sub.6 alkyl;

R.sup.2 and R.sup.3 independently are hydrogen, C.sub.1 -C.sub.6 alkyl, CH.sub.2 C.sub.2 -C.sub.5 alkenyl, phenyl-C.sub.1 -C.sub.3 alkyl, or taken together with the nitrogen to which they are attached are a cyclic group of the formula ##STR13## in which R.sup.8 is hydrogen or C.sub.1 -C.sub.4 alkyl; A is CH.sub.2, O or NH; and y is zero or one; provided that R.sup.2 is hydrogen when R.sup.1 is hydroxy;

n is 3, 4 or 5;

R.sup.6 and R.sup.7 independently are hydrogen, C.sub.1 -C.sub.4 alkyl or halogen,

and the pharmaceutically acceptable salts thereof.

2. The compound of claim 1 wherein:

R.sup.1 is hydroxy, cyano, or CONR.sup.4 R.sup.5 in which R.sup.4 and R.sup.5 independently are hydrogen or C.sub.1 -C.sub.6 alkyl;

n is 3 or 4;

R.sup.2 and R.sup.3 independently are hydrogen, C.sub.1 -C.sub.6 alkyl, CH.sub.2 C.sub.2 -C.sub.5 alkenyl, phenyl-C.sub.1 -C.sub.3 alkyl, or taken together are C.sub.4 -C.sub.5 alkylene or --CH.sub.2 CH.sub.2 --O--CH.sub.2 CH.sub.2 --;

R.sup.6 and R.sup.7 are hydrogen;

and the pharmaceutically acceptable acid addition salts and lower alkyl quaternary ammonium salts thereof.

3. The compound of claim 2 wherein R.sup.1 is hydroxy, R.sup.2 is hydrogen and R.sup.3 is C.sub.1 -C.sub.6 alkyl.

4. The compound of claim 3 wherein R.sup.3 is C.sub.1 -C.sub.3 alkyl.

5. The compound of claim 4 wherein R.sup.3 is methyl.

6. The compound of claim 4 wherein R.sup.3 is ethyl.

7. The compound of claim 4 wherein R.sup.3 is n-propyl.

8. The compound of claim 4 wherein R.sup.3 is iso-propyl.

9. The compound of claim 1 wherein R.sup.1 is cyano.

10. The compound of claim 9 wherein R.sup.3 is C.sub.1 -C.sub.6 alkyl.

11. The compound of claim 10 wherein R.sup.3 is C.sub.1 -C.sub.3 alkyl.

12. The compound of claim 11 wherein R.sup.3 is iso-propyl.

13. The compound of claim 1 wherein R.sup.1 is CONR.sup.4 R.sup.5.

14. The compound of claim 13 wherein R.sup.4 and R.sup.5 both are hydrogen.

15. The compound of claim 14 wherein R.sup.6 and R.sup.7 both are hydrogen.

16. The compound of claim 15 wherein R.sup.3 is C.sub.1 -C.sub.6 alkyl.

17. The compound of claim 16 wherein R.sup.2 is hydrogen.

18. The compound of claim 17 wherein R.sup.3 is C.sub.1 -C.sub.3 alkyl.

19. The compound of claim 18 wherein n is 3.

20. The compound of claim 19 wherein R.sup.3 is methyl or ethyl.

21. The compound of claim 19 wherein R.sup.3 is n-propyl.

22. The compound of claim 18 wherein R.sup.3 is iso-propyl.

23. The compound of claim 22, said compound being 9-(3-isopropylaminopropyl)-9-aminocarbonylfluorene.

24. The compound of claim 1 as a pharmaceutically acceptable acid addition salt.

25. The compound of claim 24, said compound being 9-(3-isopropylaminopropyl)-9-aminocarbonylfluorene hydrochloride.

26. The compound of claim 24, said compound being 9-(3-isopropylaminopropyl)-9-aminocarbonylfluorene hydrobromide.

27. The compound of claim 1 as a C.sub.1 -C.sub.6 alkyl quaternary ammonium salt.

28. The compound of claim 1 wheren n is 4.

29. The compound of claim 1 wheren n is 5.
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