IP Library › Granted Patent US 10,537,590
Granted Patent B2
US 10,537,590 · App. 15/716,720 · Granted Jan 21, 2020

Cyclic dinucleotide compounds

Inventors: Thorsten Oost (Biberach an der Riss, DE); Sebastian Carotta (Vienna, AT); Martin Fleck (Warthausen, DE)
Assignee: Boehringer Ingelheim International GmbH
A61K31/7084A61K31/7076A61K39/39A61K2039/55561
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Quick Facts
Patent No.
US 10,537,590
App. No.
15/716,720
Granted
Jan 21, 2020
Kind
B2
Abstract

The present invention relates to compounds of general formula I, wherein the groups R 1 , R 2 and R 3 are defined as in claim 1 , which have valuable pharmacological properties, particularly are modulators of STING.

Claims (71)

1. A compound of formula I

wherein

R 1 is selected from the group consisting of H, F, —O—C 1-3 alkyl and OH, and

R 2 is H, or

R 2 is —CH 2 — and R 1 is —O—, forming together a —CH 2 —O— bridge, and

R 3 is a purine nucleobase selected from the group consisting of purine, adenine, guanine, xanthine and hypoxanthine, connected through its N 9 nitrogen,

or a salt thereof.

2. The compound of claim 1 , wherein the compound is a substantially pure (Sp,Sp), (Rp,Rp), (Sp,Rp), or (Rp,Sp) stereoisomer, or a salt thereof.

3. The compound of claim 1 , wherein the compound is a substantially pure (Rp,Rp) stereoisomer, or a salt thereof.

4. The compound of claim 1 , wherein the the salt is a pharmaceutically acceptable salt.

5. A pharmaceutical composition comprising one or more compounds according to claim 1 , or one or more pharmaceutically acceptable salts thereof, optionally together with one or more inert carriers and/or diluents.

6. A method for treating diseases or conditions selected from the group consisting of inflammation, allergic diseases, autoimmune diseases, infectious diseases and cancer, in a patient in need thereof, comprising administering to the patient a compound according to claim 1 .

7. A vaccine comprising a compound according claim 1 .

8. A pharmaceutical composition comprising one or more compounds according to claim 1 and one or more additional therapeutic agents, optionally together with one or more inert carriers and/or diluents.

9. A pharmaceutical composition comprising one compound according to claim 1 and one or more additional therapeutic agents.

10. A compound according to claim 1 of formula Ia:

or a salt thereof.

11. The compound of claim 10 , wherein the compound is a substantially pure (Sp,Sp), (Rp,Rp), (Sp,Rp), or (Rp,Sp) stereoisomer, or a salt thereof.

12. The compound of claim 10 , wherein the compound is a substantially pure (Rp,Rp) stereoisomer, or a salt thereof.

13. The compound of claim 10 , wherein the salt is a pharmaceutically acceptable salt.

14. A pharmaceutical composition comprising one or more compounds according to claim 10 , or one or more pharmaceutically acceptable salts thereof, optionally together with one or more inert carriers and/or diluents.

15. A method for treating diseases or conditions selected from the group consisting of inflammation, allergic diseases, autoimmune diseases, infectious diseases and cancer, in a patient in need thereof, comprising administering to the patient a compound according to claim 10 .

16. A vaccine comprising a compound according to claim 10 .

17. A pharmaceutical composition comprising one or more compounds according to claim 10 and one or more additional therapeutic agents, optionally together with one or more inert carriers and/or diluents.

18. A pharmaceutical composition according to claim 17 comprising one compound according to claim 10 and one or more additional therapeutic agents.

19. A compound according to claim 1 of formula Ib

or a salt thereof.

20. The compound of claim 19 , wherein the compound is a substantially pure (Sp,Sp), (Rp,Rp), (Sp,Rp), or (Rp,Sp) stereoisomer, or a salt thereof.

21. The compound of claim 19 , wherein the compound is a substantially pure (Rp,Rp) stereoisomer, or a salt thereof.

22. The compound of claim 19 , wherein the salt is a pharmaceutically acceptable salt.

23. A pharmaceutical composition comprising one or more compounds according to claim 19 , or one or more pharmaceutically acceptable salts thereof, optionally together with one or more inert carriers and/or diluents.

24. A method for treating diseases or conditions selected from the group consisting of inflammation, allergic diseases, autoimmune diseases, infectious diseases and cancer, in a patient in need thereof, comprising administering to the patient a compound according to claim 19 .

25. A vaccine comprising a compound according to claim 19 .

26. A pharmaceutical composition comprising one or more compounds according to claim 19 and one or more additional therapeutic agents, optionally together with one or more inert carriers and/or diluents.

27. A pharmaceutical composition according to claim 26 comprising one compound according to claim 19 and one or more additional therapeutic agents.

28. A compound of formula Ia.1:

wherein the compound is a substantially pure (Rp,Rp), (Rp,Sp), (Sp,Rp) or (Sp,Sp) stereoisomer, or any mixtures thereof, or a salt thereof.

29. The compound of claim 28 wherein the compound is a substantially pure (Rp,Rp) stereoisomer, or a salt thereof.

30. The compound of claim 28 , wherein the salt is a pharmaceutically acceptable salt.

31. The compound of claim 28 , wherein the salt is a sodium salt.

32. The compound of claim 29 , wherein the salt is a sodium salt.

33. A compound of formula Ia.2

wherein the compound is a substantially pure (Rp,Rp), (Rp,Sp), (Sp,Rp) or (Sp,Sp) stereoisomer, or any mixtures thereof, or a salt thereof.

34. The compound of claim 33 , wherein the compound is a substantially pure (Rp,Rp) stereoisomer, or a salt thereof.

35. The compound of claim 33 , wherein the salt is a pharmaceutically acceptable salt.

36. The compound of claim 33 , wherein the salt is a sodium salt.

37. The compound of claim 34 , wherein the salt is a sodium salt.

38. A compound of formula Ia.3

wherein the compound is a substantially pure (Rp,Rp), (Rp,Sp), (Sp,Rp) or (Sp,Sp) stereoisomer, or any mixtures thereof, or a salt thereof.

39. The compound of claim 38 , wherein the compound is a substantially pure (Rp,Rp) stereoisomer or a salt thereof.

40. The compound of claim 38 , wherein the salt is a pharmaceutically acceptable salt.

41. The compound of claim 38 , wherein the salt is a sodium salt.

42. The compound of claim 39 , wherein the salt is a sodium salt.

43. A compound of formula lb.1

wherein the compound is a substantially pure (Rp,Rp), (Rp,Sp), (Sp,Rp) or (Sp,Sp) stereoisomer, or any mixtures thereof, a salt thereof.

44. The compound of claim 43 , wherein the compound is a substantially pure (Rp,Rp) stereoisomer or a salt thereof.

45. The compound of claim 43 , wherein the salt is a pharmaceutically acceptable salt.

46. The compound of claim 43 , wherein the salt is a sodium salt.

47. The compound of claim 44 , wherein the salt is a sodium salt.

48. A compound of formula Ia.1:

wherein the compound is a substantially pure (Rp,Rp), (Rp,Sp), (Sp,Rp) or (Sp,Sp) stereoisomer, or any mixtures thereof.

49. The compound of claim 48 , wherein the compound is a substantially pure (Rp,Rp) stereoisomer.

50. A compound of formula Ia.2

wherein the compound is a substantially pure (Rp,Rp), (Rp,Sp), (Sp,Rp) or (Sp,Sp) stereoisomer, or any mixtures thereof.

51. The compound of claim 50 , wherein the compound is a substantially pure (Rp,Rp) stereoisomer.

52. A compound of formula Ia.3

wherein the compound is a substantially pure (Rp,Rp), (Rp,Sp), (Sp,Rp) or (Sp,Sp) stereoisomer, or any mixtures thereof.

53. The compound of claim 52 , wherein the compound is a substantially pure (Rp,Rp) stereoisomer.

54. A compound of formula Ib.1

wherein the compound is a substantially pure (Rp,Rp), (Rp,Sp), (Sp,Rp) or (Sp,Sp) stereoisomer, or any mixtures thereof.

55. The compound of claim 54 , wherein the compound is a substantially pure (Rp,Rp) stereoisomer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 20, 2017
From: OOST, THORSTEN; CAROTTA, SEBASTIAN; FLECK, MARTIN
To: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
Reel/Frame 044445/0328 →
Priority Claims (1)
EP 16191919 · Sep 30, 2016 · regional
Continuity (1)
Related Publication 20180092937A1 · Apr 5, 2018
Cited By (1)
US 12,247,071