IP Library Granted Patent US 11,510,875
Granted Patent B2
US 11,510,875 · App. 14/377,488 · Granted Nov 29, 2022

Adjuvant formulations comprising TLR4 agonists and methods of using the same

Inventors: Christopher Fox (Sumner, WA); Steven G. Reed (Bellevue, WA); Susan Baldwin (Seattle, WA); Thomas Vedvick (Federal Way, WA)
Assignee: ACCESS TO ADVANCED HEALTH INSTITUTE
A61K9/113A61K9/107A61K39/00A61K39/015A61K39/12A61K39/39A61K47/06A61K47/24A61K47/26A61K2039/55566A61K2039/55572C12N2760/16134C12N2760/16234
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Quick Facts
Patent No.
US 11,510,875
App. No.
14/377,488
Granted
Nov 29, 2022
Kind
B2
Abstract

Formulations and methods, including vaccines and pharmaceutical compositions for inducing or enhancing an immune response are disclosed. The formulations generally comprise a TLR4 agonist and a metabolizable oil at a concentration of about 0.01%-1% v/v, wherein the hydrophobic:lipophilic balance (HLB) of the emulsion is greater than about 9.

Claims (79)

1. An oil-in-water emulsion comprising a TLR4 agonist, 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC), and a metabolizable oil, wherein the TLR4 agonist comprises synthetic GLA, wherein the metabolizable oil is present in the oil-in-water emulsion at a concentration of 0.01%-1% v/v, wherein the DMPC is present in the oil-and-water emulsion at a concentration of 0.002% to 2% w/v, and wherein the hydrophobic:lipophilic balance (HLB) of the oil-in-water emulsion is greater than about 9.

2. The oil-in-water emulsion of claim 1 , wherein the metabolizable oil is present in the oil-in-water emulsion at a concentration of 0.01%- 0.5% v/v.

3. The oil-in-water emulsion of claim 1 , wherein the emulsion does not comprise egg phosphatidyl choline (PC).

4. The oil-in-water emulsion of claim 3 , wherein the emulsion does not comprise an antioxidant.

5. The oil-in-water emulsion of claim 1 , wherein the HLB of the emulsion is greater than about 10.

6. The oil-in-water emulsion of claim 1 , wherein the HLB of the emulsion is between about 9-12.

7. The oil-in-water emulsion of claim 1 , wherein the synthetic GLA has the following structure:

where: R 1 , R 3 , R 5 , and R 6 are C 11 -C 20 alkyl; and R 2 and R 4 are C 12 -C 20 alkyl.

8. The oil-in-water emulsion of claim 7 , wherein R 1 , R 3 , R 5 , and R 6 are C 11 alkyl; and R 2 and R 4 are C 13 alkyl.

9. The oil-in-water emulsion of claim 1 , wherein the synthetic GLA has the following structure:

wherein R 1 , R 3 , R 5 , and R 6 are C 10 alkyl; and R 2 and R 4 are C 8 alkyl.

10. The oil-in-water emulsion of claim 1 , wherein the emulsion further comprises a surfactant.

11. The oil-in-water emulsion of claim 10 , wherein the surfactant is pluronic F68.

12. The oil-in-water emulsion of claim 1 , wherein the metabolizable oil is squalene.

13. The oil-in-water emulsion of claim 1 , wherein the emulsion further comprises an antioxidant.

14. The oil-in-water emulsion of claim 13 , wherein the antioxidant is vitamin E.

15. The oil-in-water emulsion of claim 1 , wherein the emulsion further comprises at least one antigen.

16. An oil-in-water emulsion comprising a synthetic GLA, a metabolizable oil at a concentration of 0.01%-1% v/v, and DMPC at a concentration of 0.002%-2% w/v, wherein the HLB of the emulsion is greater than about 10.

17. The oil-in-water emulsion of claim 16 , wherein the synthetic GLA has the following structure:

where: R 1 , R 3 , R 5 , and R 6 are C 11 -C 20 alkyl; and R 2 and R 4 are C 12 -C 20 alkyl.

18. The oil-in-water emulsion of claim 17 , wherein R 1 , R 3 , R 5 , and R 6 are C 11 alkyl; and R 2 and R 4 are C 13 alkyl.

19. The oil-in-water emulsion of claim 16 , wherein the synthetic GLA has the following structure:

or a pharmaceutically acceptable salt thereof, wherein:

L 1 , L 2 , L 3 , L 4 , L 5 , and L 6 are the same or different and independently -O-, -NH- or -(CH 2 )-L 7 ,

L 8 , L 9 , and L 10 are the same or different and independently absent or -C(═O)—; Y 1 is an acid functional group;

Y 2 and Y 3 are the same or different and independently —OH, —SH, or an acid functional group;

Y 4 is —OH or —SH;

R 1 , R 3 , R 5 , and R 6 are the same or different and independently C 8-13 alkyl; and

R 2 and R 4 are the same or different and independently C 6-11 alkyl.

20. The oil-in-water emulsion of claim 19 , wherein R 1 , R 3 , R 5 , and R 6 are C 11 alkyl; and R 2 and R 4 are C 8 alkyl.

21. A method of stimulating an immune response in a subject comprising administering an oil-in-water emulsion of claim 1 to the subject and thereby stimulating an immune response in the subject.

22. The method of claim 21 , wherein the immune response is a non- specific immune response.

23. The method of claim 21 , wherein the immune response is an antigen-specific immune response.

24. The method of claim 21 , wherein the oil-in-water emulsion is administered intradermally.

25. The oil-in-water emulsion of claim 1 , wherein the synthetic GLA has the following structure:

or a pharmaceutically acceptable salt thereof, wherein: R 1 , R 3 , R 5 , and R 6 are C 11-20 alkyl; and R 2 and R 4 are C 9-20 alkyl.

26. The oil-in-water emulsion of claim 1 , wherein the synthetic GLA has the following structure:

or a pharmaceutically acceptable salt thereof, wherein: R 1 , R 3 , R 5 , and R 6 are C 11 -C 20 alkyl; and R 2 and R 4 are C 9 -C 20 alkyl.

27. The oil-in-water emulsion of claim 1 , wherein the synthetic GLA has the following structure:

or a pharmaceutically acceptable salt thereof.

28. The oil-in-water emulsion of claim 16 , wherein the synthetic GLA has the following structure:

or a pharmaceutically acceptable salt thereof, wherein: R 1 , R 3 , R 5 , and R 6 are C 11-20 alkyl; and R 2 and R 4 are C 9-20 alkyl.

29. The oil-in-water emulsion of claim 16 , wherein the synthetic GLA has the following structure:

or a pharmaceutically acceptable salt thereof, wherein: R 1 , R 3 , R 5 , and R 6 are C 11 -C 20 alkyl; and R 2 and R 4 are C 9 -C 20 alkyl.

30. The oil-in-water emulsion of claim 16 , wherein the synthetic GLA has the following structure:

or a pharmaceutically acceptable salt thereof.

31. An oil-in-water emulsion comprising a metabolizable oil and DMPC (1,2-dimyristoyl-sn-glycero-3-phosphocholine), wherein the DMPC is present in the oil-and-water emulsion at a concentration of 0.002% to 2% w/v and wherein the emulsion does not comprise egg phosphatidyl choline (PC).

32. The oil-in-water emulsion of claim 31 , wherein the metabolizable oil is present in the oil-in-water emulsion at a concentration of 0.01%-4% v/v.

33. The oil-in-water emulsion of claim 31 , wherein the emulsion does not comprise an antioxidant.

34. The oil-in-water emulsion of claim 31 , wherein a hydrophobic:lipophilic balance (HLB) of the emulsion is greater than about 10.

35. The oil-in-water emulsion of claim 31 , wherein a hydrophobic:lipophilic balance (HLB) of the emulsion is between about 9-12.

36. The oil-in-water emulsion of claim 31 , further comprising a TLR4 agonist.

37. The oil-in-water emulsion of claim 36 , wherein the TLR4 agonist comprises MPL, 3D-MPL, or synthetic GLA.

38. The oil-in-water emulsion of claim 37 , wherein the synthetic GLA has the following structure:

where: R 1 , R 3 , R 5 , and R 6 are C 11 -C 20 alkyl; and R 2 and R 4 are C 12 -C 20 alkyl.

39. The oil-in-water emulsion of claim 38 , wherein R 1 , R 3 , R 5 , and R 6 are C 11 alkyl; and R 2 and R 4 are C 13 alkyl.

40. The oil-in-water emulsion of claim 37 , wherein the synthetic GLA has the following structure:

or a pharmaceutically acceptable salt thereof, wherein: R 1 , R 3 , R 5 , and R 6 are C 11-20 alkyl; and R 2 and R 4 are C 12-20 alkyl.

41. The oil-in-water emulsion of claim 31 , wherein the emulsion further comprises a surfactant.

42. The oil-in-water emulsion of claim 41 , wherein the surfactant is pluronic F68.

43. The oil-in-water emulsion of claim 31 , wherein the metabolizable oil is squalene.

44. The oil-in-water emulsion of claim 31 , wherein the emulsion further comprises an antioxidant.

45. The oil-in-water emulsion of claim 44 , wherein the antioxidant is vitamin E.

46. The oil-in-water emulsion of claim 31 , wherein the emulsion further comprises at least one antigen.

47. A method of stimulating an immune response in a subject comprising administering an oil-in-water emulsion of claim 31 to the subject and thereby stimulating an immune response in the subject.

48. The method of claim 47 , wherein the immune response is a non- specific immune response.

49. The method of claim 47 , wherein the immune response is an antigen-specific immune response.

50. The method of claim 47 , wherein the oil-in-water emulsion is administered intradermally.

51. The oil-in-water emulsion of claim 31 , wherein the DMPC is present in the oil-in-water emulsion at a concentration of 0.015% to 0.25% w/v.

52. The oil-in-water emulsion of claim 32 , wherein the metabolizable oil is squalene.

53. The oil-in-water emulsion of claim 36 , wherein the metabolizable oil is squalene.

54. The oil-in-water emulsion of claim 51 , wherein the metabolizable oil is squalene.

55. The oil-in-water emulsion of claim 16 , wherein the metabolizable oil is squalene.

56. A method of stimulating an immune response in a subject comprising administering an oil-in-water emulsion of claim 16 to the subject and thereby stimulating an immune response in the subject.

57. The method of claim 56 , wherein the immune response is a non-specific immune response.

58. The method of claim 56 , wherein the immune response is an antigen-specific immune response.

59. The method of claim 56 , wherein the oil-in-water emulsion is administered intradermally.

60. The oil-in-water emulsion of claim 37 , wherein the TLR4 agonist comprises synthetic GLA.

61. The oil-in-water emulsion of claim 31 , wherein a hydrophobic:lipophilic balance (HLB) of the emulsion is greater than about 9.

Assignments (2)
CHANGE OF NAME Recorded Aug 15, 2022
From: INFECTIOUS DISEASE RESEARCH INSTITUTE
To: ACCESS TO ADVANCED HEALTH INSTITUTE
Reel/Frame 061177/0823 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2022
From: FOX, CHRISTOPHER; REED, STEVEN G.; BALDWIN, SUSAN; VEDVICK, THOMAS
To: INFECTIOUS DISEASE RESEARCH INSTITUTE
Reel/Frame 059096/0780 →
Continuity (2)
Provisional Application 61596066 · Feb 7, 2012
Related Publication 20150017191A1 · Jan 15, 2015