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Claims for Patent: 5,583,131

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Claims for Patent: 5,583,131

Title: Aromatic-linked polyamine macrocyclic compounds with anti-HIV activity
Abstract:Polyamine macrocyclic compounds, e.g. of 10 to 15 ring members and 3 to 6 ring amine nitrogens, linked through methylene groups to an aromatic moiety, show high selective activity against HIV.
Inventor(s): Bridger; Gary J. (West Chester, PA), Padmanbhan; Sreenivasan (Exton, PA), Skerlj; Renato T. (West Chester, PA), Thornton; David M. (Reading, PA)
Assignee: Johnson Matthey Public Limited Company (London, GB)
Application Number:08/244,863
Patent Claims: 1. A pharmaceutical composition active against HIV comprising as an active ingredient a linked cyclic compound of formula I,

in which Z and Y are identical cyclic polyamine moieties having from 10 to 15 ring members and from 3 to 6 amine nitrogens in the ring spaced by 2 or more carbon atoms from each other, said amine nitrogens being the only ring heteroatoms,

A is an aromatic or heteroaromatic moiety other than quinoline,

R and R' are each methylene linked to nitrogen atoms in Z and Y,

the amine nitrogen atoms being otherwise unsubstituted.

2. A composition according to claim 1, wherein in the compound of formula I, each moiety Z and Y has 14 ring members and 4 amine nitrogens in the ring.

3. A composition according to claim 1, wherein the active ingredient is 1,1'-[1,3-phenylenebis(methylene)]-bis-1,4,8,11-tetra-azacyclotetradecane in acid addition salt form.

4. A composition according to claim 1, wherein the active ingredient is 1,1'-[1,4-phenylenebis(methylene)]-bis-1,4,8,11-tetra-azacyclotetradecane in acid addition salt form.

5. A composition according to claim 1, wherein the active ingredient is a bis-zinc complex of 1,1'-[1,4-phenylene-bis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane

6. A composition according to claim 1, wherein the active ingredient is a bis-copper complex of 1,1'-[1,4-phenylene-bis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane .

7. A composition according to claim 1, wherein the active ingredient is 1,1'-[3,3'-biphenylene-bis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradec ane in acid addition salt form.

8. A composition according to claim 1, wherein the active ingredient is 11,11'-[1,4-phenylene-bis-(methylene)]-bis-1,4,7,1 1-tetraazacyclotetradecane in acid addition salt form.

9. A composition according to claim 1, wherein the active ingredient is 1,11'-[1,4-phenylene-bis-(methylene)]-1,4,8,11-tetraazacyclotetradecane-1, 4,7,11-tetraazacyclotetradecane in acid addition salt form.

10. A composition according to claim 1, wherein the active ingredient is 1,1'-[2,6-pyridine-bis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane in acid addition salt form.

11. A composition according to claim 1, wherein the active ingredient is 1,1-[3,5-pyridine-bis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane in acid addition salt form.

12. A composition according to claim 1, wherein the active ingredient is 1,1'-[2,5-thiophene-bis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane in acid addition salt form.

13. A composition according to claim 1, wherein the active ingredient is 1,1'-[4,4'-(2,2'-bipyridine)-bis-(methylene)]-bis-1,4,8,11-tetraazacyclote tradecane in acid addition salt form.

14. A composition according to claim 1, wherein the active ingredient is 1,1'-[2,9-(1,10-phenanthroline)-bis-(methylene)]-bis-1,4,8,11-tetraazacycl otetradecane in acid addition salt form.

15. A composition according to claim 1, wherein the active ingredient is 1,1'-[1,3-phenylene-bis-(methylene)]-bis-1,4,7,10-tetraazacyclotetradecane in acid addition salt form.

16. A composition according to claim 1, wherein the active ingredient is 1,1'-[1,4-phenylene-bis-(methylene)]-bis-1,4,7,10-tetraazacyclotetradecane in acid addition salt form.

17. The compound of claim 1, which is 1,1'-[5-nitro-1,3-phenylenebis(methylene)]bis-1,4,8,11-tetraazacyclotetrad ecane in acid addition salt form.

18. The compound of claim 1, which is 1'1'-[2,4,5,6-tetrachloro-1,3-phenyleneis(methylene)]bis-1,4,8,11-tetraaza cyclotetradecane in acid addition salt form.

19. The compound of claim 1, which is 1,1'-[2,3,5,6-tetra-fluoro-1,4-phenylenebis(methylene)]bis-1,4,8,11-tetraa zacyclotetradecane in acid addition salt form.

20. The compound of claim 1, which is 1,1'-[1,4-naphthylene-bis-(methylene)]bis-1,4,8,11-tetraazacyclotetradecan e in acid addition salt form.

21. The compound of claim 1, which is 1,1'-[1,3-phenylenebis-(methylene)]bis-1,5,9-triazacyclododecane in acid addition salt form.

22. The compound of claim 1, which is 1,1'-[1,4-phenylene-bis-(methylene)]-1,5,9-trlazacyclododecane in acid addition salt form.

23. The compound of claim 1, which is a bis-zinc complex of 1,1'[1,4-phenylene-bis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane.

24. The compound of claim 1, which is 1,1'-[3,3'-biphenylene-bis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradec ane in acid addition salt form.

25. The compound of claim 1, which is 1,1'-[2,6-pyridine-bis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane in acid addition salt form.

26. The compound of claim 1, which is 1,1'-[3,5-pyridine-bis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane in acid addition salt form.

27. The compound of claim 1, which is 1,1'-[2,5-thiophene-bis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane in acid addition salt form.

28. The compound of claim 1, which is 1,1'-[4,4'-(2,2'-bipyridine)-bis-(methylene)]-bis-1,4,8,11-tetraazacyclote tradecane in acid addition salt form.

29. The compound of claim 1, which is 1,1'-[2,9-(1,10-phenanthroline)-bis-(methylene)]-bis-1,4,8,11-tetraazacycl otetradecane in acid addition salt form.

30. The compound of claim 1, which is 1,1'-[1,3-phenylene-bis-(methylene)]-bis-1,4,7,10-tetraazacyclotetradecane in acid addition salt form.

31. The compound of claim 1, which is 1,1'-[1,4-phenylene-bis-(methylene)]-bis-1,4,7,10-tetraazacyclotetradecane in acid addition salt form.

32. The compound of claim 1, which is 1,1'-[2,5-dimethyl-1,4-phenylenebis-(methylene)]-bis-1,4,8,11-tetraazacycl otetradecane.

33. The compound of claim 1, which is 1,1'-[2,5-dichloro-1,4-phenylenebis-(methylene)]-bis-1,4,8,11-tetraazacycl otetradecane.

34. The compound of claim 1, which is 1,1'-[2-bromo-1,4-phenylenebis-(methylene)]-bis-1,4,8,11-tetraazacyclotetr adecane.

35. The compound of claim 1, which is 1,1'-[6-phenyl-2,4-pyridinebis-(methylene)]-bis-1,4,8,11-tetraazacyclotetr adecane.
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