IP Library Granted Patent US 8,476,222
Granted Patent B2
US 8,476,222 · App. 12/417,307 · Granted Jul 2, 2013

Isolated peptides from

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Quick Facts
Patent No.
US 8,476,222
App. No.
12/417,307
Granted
Jul 2, 2013
Kind
B2
Abstract

The disclosure relates to a compound of the formula (I) wherein R1 is H, C(O)—(C 1 -C 6 )alkyl or C(O)—O—(C 1 -C 6 )alkyl; R2 is OH, NH 2 , NH—(C 1 -C 6 )alkyl, NH—(C 1 -C 4 )alkylene-phenyl or NH—(C 1 -C 4 )alkylene-pyridyl; R3 and R4 are independently of each other H or OH, or R3 and R4 together are ═O; and m and n are independently of one another 0, 1 or 2; in any stereochemical form, or a mixture of any stereochemical forms in any ratio, or a physiologically acceptable salt thereof, obtainable from Actinomadura namibiensis (DSM 6313), and its use for the treatment of bacterial infections, viral infections and/or pain, and pharmaceutical composition comprising it.

Claims (40)

1. An isolated compound of the formula (I):

wherein

R1 is H, C(O)—(C 1 -C 6 )alkyl or C(O)—O—(C 1 -C 6 )alkyl;

R2 is OH, NH 2 , NH—(C 1 -C 6 )alkyl, NH—(C 1 -C 4 )alkylene-phenyl or NH—(C 1 -C 4 )alkylene-pyridyl;

R3 and R4 are independently of each other H or OH, or R3 and R4 together are ═O; and

m and n are independently of one another 0, 1 or 2; and

said compound being in any stereochemical form, or a mixture of any stereochemical forms in any ratio;

or a physiologically acceptable salt thereof.

2. The isolated compound according to claim 1 having the formula (II):

or a physiologically acceptable salt thereof.

3. The isolated compound according to claim 1 wherein R1 is H; or a physiologically acceptable salt thereof.

4. The isolated compound according to claim 2 wherein R1 is H; or a physiologically acceptable salt thereof.

5. The isolated compound according to claim 1 wherein R2 is OH; or a physiologically acceptable salt thereof.

6. The isolated compound according to claim 2 wherein R2 is OH; or a physiologically acceptable salt thereof.

7. The isolated compound according to claim 1 wherein R3 and R4 are H or OH and wherein if R3 is OH then R4 is H, or if R3 is H then R4 is OH, or R3 and R4 together are ═O; or a physiologically acceptable salt thereof.

8. The isolated compound according to claim 2 wherein R3 and R4 are H or OH and wherein if R3 is OH then R4 is H, or if R3 is H then R4 is OH, or R3 and R4 together are ═O; or a physiologically acceptable salt thereof.

9. The isolated compound according to claim 1 wherein R3 is OH and R4 is H, or R3 is H and R4 is OH; or a physiologically acceptable salt thereof.

10. The isolated compound according to claim 2 wherein R3 is OH and R4 is H, or R3 is H and R4 is OH; or a physiologically acceptable salt thereof.

11. The isolated compound according to claim 1 wherein m and n are both 0, or m and n are both 2, or m is 0 and n is 2, or m is 2 and n is 0; or a physiologically acceptable salt thereof.

12. The isolated compound according to claim 2 wherein m and n are both 0, or m and n are both 2, or m is 0 and n is 2, or m is 2 and n is 0; or a physiologically acceptable salt thereof.

13. The isolated compound according to claim 1 wherein m and n are both 0; or a physiologically acceptable salt thereof.

14. The isolated compound according to claim 2 wherein m and n are both 0; or a physiologically acceptable salt thereof.

15. The isolated compound according to claim 1 wherein R1 is H; R2 is OH; R3 and R4 are independently of each other H or OH wherein if R3 is OH then R4 is H, and if R3 is H then R4 is OH; and m and n are independently of one another 0, 1 or 2; or a physiologically acceptable salt thereof.

16. The isolated compound according to claim 2 wherein R1 is H; R2 is OH; R3 and R4 are independently of each other H or OH wherein if R3 is OH then R4 is H, and if R3 is H then R4 is OH; and m and n are independently of one another 0, 1 or 2; or a physiologically acceptable salt thereof.

17. The isolated compound according to claim 1 wherein R1 is H; R2 is OH; R3 and R4 are independently of each other H or OH wherein if R3 is OH then R4 is H, and if R3 is H then R4 is OH; and m and n are both 0, or m and n are both 2, or m is 0 and n is 2, or m is 2 and n is 0; or a physiologically acceptable salt thereof.

18. The isolated compound according to claim 2 wherein R1 is H; R2 is OH; R3 and R4 are independently of each other H or OH wherein if R3 is OH then R4 is H, and if R3 is H then R4 is OH; and m and n are both 0, or m and n are both 2, or m is 0 and n is 2, or m is 2 and n is 0; or a physiologically acceptable salt thereof.

19. The isolated compound according to claim 1 wherein R1 is H; R2 is OH; R3 and R4 are independently of each other H or OH and wherein if R3 is OH then R4 is H, and if R3 is H then R4 is OH; and m and n are both 0; or a physiologically acceptable salt thereof.

20. The isolated compound according to claim 2 wherein R1 is H; R2 is OH; R3 and R4 are independently of each other H or OH and wherein if R3 is OH then R4 is H, and if R3 is H then R4 is OH; and m and n are both 0; or a physiologically acceptable salt thereof.

21. The isolated compound according to claim 1 having the formula (III):

or a physiologically acceptable salt thereof.

22. The isolated compound according to claim 21 , which is isolated from Actinomadura namibiensis (DSM 6313).

23. A method for treating a bacterial infection or pain comprising administering to a patient in need of said treatment a therapeutically effective amount of an isolated compound according to claim 1 , or a physiologically acceptable salt thereof.

24. A pharmaceutical composition comprising at least one isolated compound according to claim 1 , or a physiologically acceptable salt thereof, and at least one pharmaceutically acceptable ingredient.

25. A process for preparing an isolated compound of formula (I) according to claim 1 which comprises

a) fermenting the strain Actinomadura namibiensis (DSM 6313) under suitable conditions in a culture medium until one or more of the compounds according to claim 1 of the formula (I) accrue(s) in the culture medium,

b) isolating the compound according to claim 1 from the culture medium, and

c) formulating the compound according to claim 1 of formula (I) into a physiologically acceptable salt where appropriate.

26. The process according to claim 25 wherein the isolated compound is of the formula (II):

27. The process according to claim 25 wherein the isolated compound is of the formula (Ill):

28. The process according to claim 25 wherein for the isolated compound according to claim 1 , m and n are both 0, or m and n are both 2, or m is 0 and n is 2, or m is 2 and n is 0.

Assignments (1)
CHANGE OF NAME Recorded Jun 20, 2012
From: SANOFI-AVENTIS
To: SANOFI
Reel/Frame 028413/0927 →