Last Updated: May 31, 2026

Claims for Patent: 4,452,745


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Summary 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):William B. Lacefield, Richard L. Simon
Assignee: Eli Lilly and Co
Application Number:US06/426,491
Patent Claims: 1. A compound of the formula ##STR12## wherein: R1 is hydroxy, cyano, or CONR4 R5 in which R4 and R5 independently are hydrogen or C1 -C6 alkyl;R2 and R3 independently are hydrogen, C1 -C6 alkyl, CH2 C2 -C5 alkenyl, phenyl-C1 -C3 alkyl, or taken together with the nitrogen to which they are attached are a cyclic group of the formula ##STR13## in which R8 is hydrogen or C1 -C4 alkyl; A is CH2, O or NH; and y is zero or one; provided that R2 is hydrogen when R1 is hydroxy; n is 3, 4 or 5; R6 and R7 independently are hydrogen, C1 -C4 alkyl or halogen, and the pharmaceutically acceptable salts thereof.

2. The compound of claim 1 wherein:R1 is hydroxy, cyano, or CONR4 R5 in which R4 and R5 independently are hydrogen or C1 -C6 alkyl; n is 3 or 4; R2 and R3 independently are hydrogen, C1 -C6 alkyl, CH2 C2 -C5 alkenyl, phenyl-C1 -C3 alkyl, or taken together are C4 -C5 alkylene or --CH2 CH2 --O--CH2 CH2 --; R6 and R7 are hydrogen; and the pharmaceutically acceptable acid addition salts and lower alkyl quaternary ammonium salts thereof.

3. The compound of claim 2 wherein R1 is hydroxy, R2 is hydrogen and R3 is C1 -C6 alkyl.

4. The compound of claim 3 wherein R3 is C1 -C3 alkyl.

5. The compound of claim 4 wherein R3 is methyl.

6. The compound of claim 4 wherein R3 is ethyl.

7. The compound of claim 4 wherein R3 is n-propyl.

8. The compound of claim 4 wherein R3 is iso-propyl.

9. The compound of claim 1 wherein R1 is cyano.

10. The compound of claim 9 wherein R3 is C1 -C6 alkyl.

11. The compound of claim 10 wherein R3 is C1 -C3 alkyl.

12. The compound of claim 11 wherein R3 is iso-propyl.

13. The compound of claim 1 wherein R1 is CONR4 R5.

14. The compound of claim 13 wherein R4 and R5 both are hydrogen.

15. The compound of claim 14 wherein R6 and R7 both are hydrogen.

16. The compound of claim 15 wherein R3 is C1 -C6 alkyl.

17. The compound of claim 16 wherein R2 is hydrogen.

18. The compound of claim 17 wherein R3 is C1 -C3 alkyl.

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

20. The compound of claim 19 wherein R3 is methyl or ethyl.

21. The compound of claim 19 wherein R3 is n-propyl.

22. The compound of claim 18 wherein R3 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 C1 -C6 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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