7-phenyl-substituted tetracycline compounds

Title: 7-phenyl-substituted tetracycline compounds

Brief Patent Description - Full Patent Description - Patent Claims

The Patent Description & Claims data below is from USPTO Patent Application 20080306032, 7-phenyl-substituted tetracycline compounds.

1. A 7-substituted tetracycline compound which is substantially free of positional isomers, said compound having the formula: wherein: R4 and R4′ are each alkyl; R5 is hydrogen, hydroxyl, or a prodrug moiety; R6 and R6′ are each independently hydrogen, hydroxyl, alkyl, or taken together, alkenyl; R7 is halo substituted, N-substituted or unsubstituted phenyl, and pharmaceutically acceptable salts thereof, wherein said tetracycline compound is substantially free of positional isomers.

2. The compound of claim 1, wherein R5, R6 and R6′ are each hydrogen and R4 and R4′ are each methyl.

3. The compound of claim 1, wherein R7 is unsubstituted phenyl.

4. The compound of claim 1, wherein R7 is 2-substituted phenyl.

5. The compound of claim 4, wherein said compound is selected from the group consisting of 7-(2-fluorophenyl) sancycline, 7-(2-chlorophenyl) sancycline, 7-(2-bromophenyl) sancycline, and 7-(2-iodophenyl) sancycline.

6. The compound of claim 1, wherein R7 is 3-substituted phenyl.

7. The compound of claim 6, wherein said compound is selected from the group consisting of 7-(3-fluorophenyl) sancycline, 7-(3-chlorophenyl) sancycline, 7-(3-bromophenyl) sancycline, and 7-(3-iodophenyl) sancycline.

8. The compound of claim 1, wherein R7 is 4-substituted phenyl.

9. The compound of claim 8, wherein said compound is selected from the group consisting of 7-(4-fluorophenyl) sancycline, 7-(4-chlorophenyl) sancycline, 7-(4-bromophenyl) sancycline, 7-(4-iodophenyl) sancycline, 7-(4-trichloromethylphenyl) sancycline, 7-(4-trifluoromethylphenyl) sancycline, 7-(4-tribromomethylphenyl) sancycline, and 7-(4-triiodomethylphenyl) sancycline.

10. The compound of claim 1, wherein R7 is 2-N-substituted phenyl.

11. The compound of claim 10, wherein said 2-N-substituted phenyl is substituted with a nitro group.

12. The compound of claim 11, wherein said compound is 7-(2-nitrophenyl) sancycline.

13. The compound of claim 10, wherein said 2-N-substituted phenyl is 2-amino substituted.

14. The compound of claim 13, wherein said 2-amino substituent is dialkylamino.

15. The compound of claim 14, wherein said dialkyl amino group is dimethylamino.

16. The compound of claim 13, wherein said compound is selected from the group consisting of 7-(2-aminophenyl) sancycline, 7-(2-N,N,-dimethylaminophenyl) sancycline, 7-(2-N,N,-diethylaminophenyl) sancycline, 7-(2-N,N,-dipropylaminophenyl) sancycline, and 7-(2-N,N,-dibutylaminophenyl) sancycline.

17. The compound of claim 1, wherein R7 is 3-N-substituted phenyl.

18. The compound of claim 17, wherein said 3-N-substituted phenyl is substituted with a nitro group.

19. The compound of claim 18, wherein said compound is 7-(3-nitrophenyl) sancycline.

20. The compound of claim 17, wherein said 3-N-substituted phenyl is 3-amino substituted.

21. The compound of claim 20, wherein said 3-amino substituent is dialkylamino.

22. The compound of claim 21, wherein said dialkyl amino group is dimethylamino.

23. The compound of claim 20, wherein said compound is selected from the group consisting of 7-(3-aminophenyl) sancycline, 7-(3-N,N,-dimethylaminophenyl) sancycline, 7-(3-N,N,-diethylaminophenyl) sancycline, 7-(3-N,N,-dipropylaminophenyl) sancycline, and 7-(3-N,N,-dibutylaminophenyl) sancycline.

24. The compound of claim 1, wherein R7 is 4-N-substituted phenyl.

25. The compound of claim 24, wherein said 4-N-substituted phenyl is substituted with a nitro group.

26. The compound of claim 25, wherein said compound is 7-(4-nitrophenyl) sancycline.

27. The compound of claim 24, wherein said 4-substituted phenyl is 4-amino substituted.

28. The compound of claim 27, wherein said 4-amino substituent is dialkyl.

29. The compound of claim 28, wherein said dialkyl amino group is dimethyl.

30. The compound of claim 29, wherein said compound is 7-(4-aminophenyl) sancycline, 7-(4-N,N,-dimethylaminophenyl) sancycline, 7-(4-N,N,-diethylaminophenyl) sancycline, 7-(4-N,N,-dipropylaminophenyl) sancycline, or 7-(4-N,N,-dibutylaminophenyl) sancycline.

31. A tetracycline compound which is substantially free of positional isomers, wherein said tetracycline compound is 7,9-diphenyl sancycline, and pharmaceutically acceptable salts thereof, wherein said tetracycline compound is substantially free of positional isomers.

32. The compound of any one of claims 1 or 31, wherein said compound is at least 75% free of positional isomers.

33. The compounds of claim 32, wherein said compound is at least 80% free of positional isomers.

34. The compounds of claim 33, wherein said compound is at least 85% free of positional isomers.

35. The compound of claim 34, wherein said compound is at least 90% free of positional isomers.

36. The compound of claim 35, wherein said compound is at least 95% free of positional isomers.

37. A method for treating a tetracycline responsive state in a mammal, comprising administering to said mammal a 7-substituted tetracycline compound, which is substantially free of positional isomers, of formula (I): wherein: R4 and R4′ are each alkyl; R5 is hydrogen, hydroxyl, or a prodrug moiety; R6 and R6′ are each independently hydrogen, hydroxyl, alkyl, or taken together, alkenyl; R7 is halo substituted, N-substituted or unsubstituted phenyl; and pharmaceutically acceptable salts thereof, such that the tetracycline responsive state is treated, wherein said tetracycline compound is substantially free of positional isomers.

38. The method of claim 37, wherein R5, R6 and R6′ are each hydrogen and R4 and R4′ are each methyl.

39. The method of claim 38, wherein R7 is unsubstituted phenyl.

40. The method of claim 38, wherein R7 is 2-substituted phenyl.

41. The method of claim 40, wherein said compound is selected from the group consisting of 7-(2-fluorophenyl) sancycline, 7-(2-chlorophenyl) sancycline, 7-(2-bromophenyl) sancycline, 7-(2-iodophenyl) sancycline, 7-(2-nitrophenyl) sancycline, 7-(2-aminophenyl) sancycline, 7-(2-N,N,-dimethylaminophenyl) sancycline, 7-(2-N,N,-diethylaminophenyl) sancycline, 7-(2-N,N,-dipropylaminophenyl) sancycline, and 7-(2-N,N,-dibutylaminophenyl) sancycline.

42. The method of claim 38, wherein R7 is 3-substituted phenyl.

43. The method of claim 42, wherein said compound is selected from the group consisting of 7-(3-fluorophenyl) sancycline, 7-(3-chlorophenyl) sancycline, 7-(3-bromophenyl) sancycline, 7-(3-iodophenyl) sancycline, 7-(3-nitrophenyl) sancycline, 7-(3-aminophenyl) sancycline, 7-(3-N,N,-dimethylaminophenyl) sancycline, 7-(3-N,N,-diethylaminophenyl) sancycline, 7-(3-N,N,-dipropylaminophenyl) sancycline, and 7-(3-N,N,-dibutylaminophenyl) sancycline.

44. The method of claim 38, wherein R7 is 4-substituted phenyl.

45. The method of claim 44, wherein said compound is selected from the group consisting of 7-(4-fluorophenyl) sancycline, 7-(4-chlorophenyl) sancycline, 7-(4-bromophenyl) sancycline, 7-(4-iodophenyl) sancycline, 7-(4-trichloromethylphenyl) sancycline, 7-(4-trifluoromethylphenyl) sancycline, 7-(4-tribromomethylphenyl) sancycline, 7-(4-triiodomethylphenyl) sancycline, 7-(4-nitrophenyl) sancycline, 7-(4-aminophenyl) sancycline, 7-(4-N,N,-dimethylaminophenyl) sancycline, 7-(4-N,N,-diethylaminophenyl) sancycline, 7-(4-N,N,-dipropylaminophenyl) sancycline, and 7-(4-N,N,-dibutylaminophenyl) sancycline.

46. A method for treating a tetracycline responsive state in a mammal, comprising administering to said mammal 7,9-diphenyl sancycline and pharmaceutically acceptable salts thereof, which is substantially free of positional isomers, such that the tetracycline responsive state is treated, wherein said 7,9-diphenyl sancycline is substantially free of positional isomers.

47. The method of claim 37 or 46, wherein said tetracycline responsive state is a bacterial infection.

48. The method of claim 47, wherein said bacterial infection is associated with E. coli.

49. The method of claim 47, wherein said bacterial infection is associated with S. aureus.

50. The method of claim 47, wherein said bacterial infection is associated with E. faecalis.

51. The method of claim 47, wherein said bacterial infection is resistant to other tetracycline antibiotics.

52. The method of claim 37 or 46, wherein said compound is administered with a pharmaceutically acceptable carrier.

53. The method of any one of claims 37 or 46, wherein said compound is at least 75% free of positional isomers.

54. The method of claim 53, wherein said compound is at least 80% free of positional isomers.

55. The method of claim 54, wherein said compound is at least 85% free of positional isomers.

56. The method of claim 55, wherein said compound is at least 90% free of positional isomers.

57. The method of claim 56, wherein said compound is at least 95% free of positional isomers.

58. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 or 31, and a pharmaceutically acceptable carrier.

59. The pharmaceutical composition of claim 58, wherein said compound is selected from the group consisting of 7-phenyl sancycline, 7,9 diphenylsancycline, 7-(2-fluorophenyl) sancycline, 7-(2-chlorophenyl) sancycline, 7-(2-bromophenyl) sancycline, 7-(2-iodophenyl) sancycline, 7-(3-fluorophenyl) sancycline, 7-(3-chlorophenyl) sancycline, 7-(3-bromophenyl) sancycline, 7-(3-iodophenyl) sancycline, 7-(4-fluorophenyl) sancycline, 7-(4-chlorophenyl) sancycline, 7-(4-bromophenyl) sancycline, 7-(4-iodophenyl) sancycline, 7-(4-trichloromethylphenyl) sancycline, 7-(4-trifluoromethylphenyl) sancycline, 7-(4-tribromomethylphenyl) sancycline, 7-(4-triiodomethylphenyl) sancycline, 7-(2-nitrophenyl) sancycline, 7-(2-aminophenyl) sancycline, 7-(2-N,N,-dimethylaminophenyl) sancycline, 7-(2-N,N,-diethylaminophenyl) sancycline, 7-(2-N,N,-dipropylaminophenyl) sancycline, 7-(2-N,N,-dibutylaminophenyl) sancycline, 7-(3-nitrophenyl) sancycline, 7-(3-aminophenyl) sancycline, 7-(3-N,N,-dimethylaminophenyl) sancycline, 7-(3-N,N,-diethylaminophenyl) sancycline, 7-(3-N,N,-dipropylaminophenyl) sancycline, 7-(3-N,N,-dibutylaminophenyl) sancycline, 7-(4-nitrophenyl) sancycline, 7-(4-aminophenyl) sancycline, 7-(4-N,N,-dimethylaminophenyl) sancycline, 7-(4-N,N,-diethylaminophenyl) sancycline, 7-(4-N,N,-dipropylaminophenyl) sancycline, and 7-(4-N,N,-dibutylaminophenyl) sancycline.

60. The pharmaceutical composition of claim 58 wherein said compound is at least 75% free of positional isomers.

61. The pharmaceutical composition of claim 60, wherein said compound is at least 80% free of positional isomers.

62. The pharmaceutical composition of claim 61, wherein said compound is at least 85% free of positional isomers.

63. The pharmaceutical composition of claim 62, wherein said compound is at least 90% free of positional isomers.

64. The pharmaceutical composition of claim 63, wherein said compound is at least 95% free of positional isomers.

Brief Patent Description - Full Patent Description - Patent Claims

Click on the above for other options relating to this 7-phenyl-substituted tetracycline compounds patent application.

Patent Applications in related categories:

20090291925 - Bioactive polymeric liquid formulations of absorbable, segmented aliphatic polyurethane compositions - Bioactive liquid formulations are formed of combinations of absorbable, segmented aliphatic polyurethane compositions and liquid polyether for use as vehicles for the controlled release of at least one active agent for the conventional and unconventional treatment of different forms of cancer and the management of at least one type of ...

###

How KEYWORD MONITOR works... a FREE service from FreshPatents
1. Sign up (takes 30 seconds). 2. Fill in the keywords to be monitored.
3. Each week you receive an email with patent applications related to your keywords.
Start now! - Receive info on patent apps like 7-phenyl-substituted tetracycline compounds or other areas of interest.
###

Previous Patent Application:
Use of a trpm5 inhibitor to regulate insulin and glp-1 release
Next Patent Application:
Use of non-steroidal anti-inflammatory drugs by inhalation in the treatment of acute and chronic bronchitis
Industry Class:
Drug, bio-affecting and body treating compositions

###

Design/code © 2009 FreshContext LLC/Freshpatents.com. Website Terms and Conditions - Also read: About this Page
Patent data source: patents published by the United States Patent and Trademark Office (USPTO)
Information published here is for research/educational purposes only (and in conjunction with our Keyword Monitor) and is not meant to be used in place of the full USPTO patent document/images or a comprehensive patent archive search. Complete official applications are on file at the USPTO and often contain additional data/images (Freshpatents is currently text-only). FreshPatents.com is not affiliated with or endorsed by the USPTO or firms/individuals or products/designs/ideas related to listed patents.

FreshPatents.com Support
Thank you for viewing the 7-phenyl-substituted tetracycline compounds patent info.
IP-related news and info

Results in 0.07652 seconds

Other interesting Feshpatents.com categories:
Electronics: Semiconductor , Audio , Illumination , Connectors , Crypto , 174

* Protect your Inventions
* US Patent Office filing

Provisional Patent
Utility Patent

PATENT INFO