IP Library Granted Patent US 11,911,466
Granted Patent B2
US 11,911,466 · App. 17/583,933 · Granted Feb 27, 2024

Substituted pyrimidines as vaccine adjuvants

Inventors: Hidenori Kimura (Tokyo, JP); Hitoshi Ban (Osaka, JP); Yoshiaki Isobe (Osaka, JP); Hitoshi Watanabe (Osaka, JP)
Assignee: Sumitomo Pharma Co., Ltd.
A61K39/39A61K39/00A61P37/04C07D239/49A61K2039/505
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,911,466
App. No.
17/583,933
Granted
Feb 27, 2024
Kind
B2
Abstract

The present invention provides a compound of the formula (1): wherein X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Y 1 , Y 2 , L, and m are as defined in the description, and a pharmaceutically acceptable salt thereof, which are useful as a vaccine adjuvant.

Claims (45)

1. A method of inducing or enhancing an antigen-specific immune reaction in a mammal, wherein the method comprises administering to the mammal in need thereof an effective amount of a compound selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

2. The method of claim 1 , wherein the antigen is a pathogen-derived antigen or a tumor antigen.

3. The method of claim 1 , wherein the antigen is a peptide or a protein.

4. The method of claim 1 , wherein the compound activates a toll-like receptor in the mammal.

5. The method of claim 1 , wherein:

(i) the compound activates toll-like receptor (TLR7) in the mammal; or

(ii) the compound activates toll-like receptor 8 (TLR8) in the mammal; or

(iii) the compound activates toll-like receptor 7 (TLR7) and toll-like receptor 8 (TLR8) in the mammal.

6. The method of claim 1 , wherein:

(a) the antigen-specific immune reaction in the mammal comprises an increase in CD4+ T lymphocytes in the mammal relative to a control; or

(b) the antigen-specific immune reaction in the mammal comprises an increase in CD8+ T lymphocytes in the mammal relative to a control.

7. The method of claim 6 , wherein the CD8+ T lymphocytes are effector memory CD8+ T lymphocytes.

8. The method of claim 1 , wherein the mammal has cancer.

9. The method of claim 1 , wherein the mammal has an infectious disease.

10. A method of inducing or enhancing an antigen-specific immune reaction in a mammal, wherein the method comprises administering to the mammal in need thereof an effective amount of a compound which is:

or a pharmaceutically acceptable salt thereof.

11. The method of claim 10 , wherein the antigen is a pathogen-derived antigen or a tumor antigen.

12. The method of claim 10 , wherein the antigen is a peptide or a protein.

13. The method of claim 10 , wherein the compound activates a toll-like receptor in the mammal.

14. The method of claim 10 , wherein:

(i) the compound activates toll-like receptor 7 (TLR7) in the mammal; or

(ii) the compound activates toll-like receptor 8 (TLR8) in the mammal; or

(iii) the compound activates toll-like receptor 7 (TLR7) and toll-like receptor 8 (TLR8) in the mammal.

15. The method of claim 10 , wherein:

(a) the antigen-specific immune reaction in the mammal comprises an increase in CD4+ T lymphocytes in the mammal relative to a control; or

(b) the antigen-specific immune reaction in the mammal comprises an increase in CD8+ T lymphocytes in the mammal relative to a control.

16. The method of claim 15 , wherein the CD8+ T lymphocytes are effector memory CD8+ T lymphocytes.

17. The method of claim 10 , wherein the mammal has cancer.

18. The method of claim 10 , wherein the mammal has an infectious disease.

19. A method of inducing or enhancing an antigen-specific immune reaction in a mammal, wherein the method comprises administering to the mammal in need thereof an effective amount of a compound which is:

or a pharmaceutically acceptable salt thereof.

20. The method of claim 19 , wherein the antigen is a pathogen-derived antigen or a tumor antigen.

21. The method of claim 19 , wherein the antigen is a peptide or a protein.

22. The method of claim 19 , wherein the compound activates a toll-like receptor in the mammal.

23. The method of claim 19 , wherein:

(i) the compound activates toll-like receptor 7 (TLR 7 ) in the mammal; or

(ii) the compound activates toll-like receptor 8 (TLR 8 ) in the mammal; or

(iii) the compound activates toll-like receptor 7 (TLR 7 ) and toll-like receptor 8 (TLR8) in the mammal.

24. The method of claim 19 , wherein:

(a) the antigen-specific immune reaction in the mammal comprises an increase in CD4+ T lymphocytes in the mammal relative to a control; or

(b) the antigen-specific immune reaction in the mammal comprises an increase in CD8+ T lymphocytes in the mammal relative to a control.

25. The method of claim 24 , wherein the CD8+ T lymphocytes are effector memory CD8+ T lymphocytes.

26. The method of claim 19 , wherein the mammal has cancer.

27. The method of claim 19 , wherein the mammal has an infectious disease.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2023
From: KIMURA, HIDENORI; BAN, HITOSHI; ISOBE, YOSHIAKI; WATANABE, HITOSHI
To: SUMITOMO DAINIPPON PHARMA CO., LTD.
Reel/Frame 065404/0043 →
CHANGE OF NAME Recorded Oct 31, 2023
From: SUMITOMO DAINIPPON PHARMA CO., LTD.
To: SUMITOMO PHARMA CO., LTD.
Reel/Frame 065404/0183 →
Priority Claims (1)
JP 2015-199750 · Oct 7, 2015 · national
Continuity (3)
Division 16822894 · Mar 18, 2020
Continuation 15766560
Related Publication 20220226468A1 · Jul 21, 2022