IP Library Granted Patent US 12,059,462
Granted Patent B2
US 12,059,462 · App. 17/262,021 · Granted Aug 13, 2024

Composition containing influenza vaccine

Inventors: Yoshimasa Takahashi (Tokyo, JP); Yu Adachi (Tokyo, JP); Manabu Ato (Tokyo, JP); Akihisa Fukushima (Osaka, JP)
Assignees: JAPAN as represented by DIRECTOR GENERAL of National Institute of Infectious Diseases; Sumitomo Pharma Co., Ltd.
A61K39/145A61K39/39A61K47/54A61P31/16A61K2039/55511
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Quick Facts
Patent No.
US 12,059,462
App. No.
17/262,021
Granted
Aug 13, 2024
Kind
B2
Abstract

The present invention provides a composition comprising a universal influenza vaccine antigen and a vaccine adjuvant.

Claims (40)

1. A composition comprising the following (1) and (2);

(1) a universal influenza vaccine antigen; and

(2) a vaccine adjuvant;

wherein the vaccine adjuvant is a substance which enhances the physiological activity of TLR7, which is selected from the group consisting of:

(4E,8E,12E,16E,20E)-N-{2-[{4-[(2-amino-4-{[(3S)-1-hydroxyhexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]benzyl}(methyl)amino]ethyl}-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenamide;

(4E,8E,12E,16E,20E)-1-(4-{4-[(2-amino-4-{[(2S)-1-hydroxypentan-2-yl]amino}-6-methylpyrimidin-5-yl)methyl]-3-methoxybenzyl}piperazin-1-yl)-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaen-1-one;

(4E,8E,12E,16E,20E)-1-(4-{4-[(2-amino-4-{[(2S)-1-hydroxypentan-2-yl]amino}-6-methylpyrimidin-5-yl)methyl]-3-methoxybenzoyl}piperazin-1-yl)-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaen-1-one;

4-[(2-amino-4-{[(2S)-1-hydroxypentan-2-yl]amino}-6-methylpyrimidin-5-yl)methyl]-N-(2-{[(4E,8E,12E,16E,20E)-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenoyl]amino}ethyl)-3-methoxybenzamide; and

4-[(2-amino-4-{[(2S)-1-hydroxypentan-2-yl]amino}-6-methylpyrimidin-5-yl)methyl]-N-(2-{[(4E,8E,12E,16E,20E)-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenoyl](methyl)amino}ethyl)-3-methoxybenzamide; or

a pharmaceutically acceptable salt thereof.

2. The composition according to claim 1 , wherein the universal influenza vaccine antigen is an influenza HA split vaccine antigen which produces an antibody that binds to a LAH of a HA stem region.

3. The composition according to claim 2 , wherein the influenza HA split vaccine antigen has a HA stem region exposed outside.

4. The composition according to claim 1 , wherein the universal influenza vaccine antigen is an influenza HA split vaccine antigen wherein the HA stem region, which is exposed outside, enhances the antigenicity of the LAH of the HA stem region, and the influenza HA split vaccine is capable of producing an antibody that binds to the LAH of the HA stem region.

5. The composition according to claim 1 , wherein the universal influenza vaccine antigen is produced by subjecting an influenza HA split vaccine to an acidic treatment.

6. The composition according to claim 1 , wherein the universal influenza vaccine antigen is produced by a production process including: subjecting an influenza HA split vaccine to an acidic treatment; and thereafter, subjecting the influenza HA split vaccine to a formalin treatment.

7. The composition according to claim 1 , wherein the substance which enhances the physiological activity of TLR7 is:

(4E,8E,12E,16E,20E)-N-{2-[{4-[(2-amino-4-{[(3S)-1-hydroxyhexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]benzyl}(methyl)amino]ethyl}-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenamide; or

4-[(2-amino-4-{[(2S)-1-hydroxypentan-2-yl]amino}-6-methylpyrimidin-5-yl)methyl]-N-(2-{[(4E,8E,12E,16E,20E)-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenoyl]amino}ethyl)-3-methoxybenzamide; or

a pharmaceutically acceptable salt thereof.

8. An influenza vaccine comprising the composition according to claim 1 .

9. A kit comprising a universal influenza vaccine antigen, and a vaccine adjuvant;

wherein the vaccine adjuvant is a substance which enhances the physiological activity of TLR7, which is selected from the group consisting of:

(4E,8E,12E,16E,20E)-N-{2-[{4-[(2-amino-4-{[(3S)-1-hydroxyhexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]benzyl}(methyl)amino]ethyl}-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenamide;

(4E,8E,12E,16E,20E)-1-(4-{4-[(2-amino-4-{[(2S)-1-hydroxypentan-2-yl]amino}-6-methylpyrimidin-5-yl)methyl]-3-methoxybenzyl}piperazin-1-yl)-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaen-1-one;

(4E,8E,12E,16E,20E)-1-(4-{4-[(2-amino-4-{[(2S)-1-hydroxypentan-2-yl]amino}-6-methylpyrimidin-5-yl)methyl]-3-methoxybenzoyl}piperazin-1-yl)-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaen-1-one;

4-[(2-amino-4-{[(2S)-1-hydroxypentan-2-yl]amino}-6-methylpyrimidin-5-yl)methyl]-N-(2-{[(4E,8E,12E,16E,20E)-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenoyl]amino}ethyl)-3-methoxybenzamide; and

4-[(2-amino-4-{[(2S)-1-hydroxypentan-2-yl]amino}-6-methylpyrimidin-5-yl)methyl]-N-(2-{[(4E,8E,12E,16E,20E)-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenoyl](methyl)amino}ethyl)-3-methoxybenzamide; or

a pharmaceutically acceptable salt thereof.

10. The composition according to claim 1 , wherein the universal influenza vaccine antigen is produced by subjecting an influenza HA split vaccine which has not undergone a formalin treatment to an acidic treatment.

11. The composition according to claim 1 , wherein the universal influenza vaccine antigen is produced by subjecting an influenza HA split vaccine of a single HA subtype to an acidic treatment.

12. The composition of according to claim 1 , wherein the universal influenza vaccine antigen is a vaccine antigen comprising two or more kinds of influenza HA split vaccine antigens each of which is produced by subjecting an influenza HA split vaccine of a single HA subtype to an acidic treatment.

13. The composition according to claim 1 , wherein the substance which enhances the physiological activity of TLR7 is:

(4E,8E,12E,16E,20E)-N-{2-[{4-[(2-amino-4-{[(3S)-1-hydroxyhexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]benzyl}(methyl)amino]ethyl}-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenamide; or

a pharmaceutically acceptable salt thereof.

14. The composition according to claim 1 , wherein the universal influenza vaccine antigen is an influenza HA split vaccine antigen which produces an antibody that binds to a LAH of a HA stem region, and the substance which enhances the physiological activity of TLR7 is (4E,8E,12E,16E,20E)-N-{2-[{4-[(2-amino-4-{[(3S)-1-hydroxyhexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]benzyl}(methyl)amino]ethyl}-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenamide or a pharmaceutically acceptable salt thereof.

15. The composition according to claim 1 , wherein the universal influenza vaccine antigen is produced by subjecting an influenza HA split vaccine to an acidic treatment, and the substance which enhances the physiological activity of TLR7 is (4E,8E,12E,16E,20E)-N-{2-[{4-[(2-amino-4-{[(3S)-1-hydroxyhexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]benzyl}(methyl)amino]ethyl}-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenamide or a pharmaceutically acceptable salt thereof.

16. The influenza vaccine according to claim 8 , wherein the universal influenza vaccine antigen is an influenza HA split vaccine antigen which produces an antibody that binds to a LAH of a HA stem region, and the substance which enhances the physiological activity of TLR7 is (4E,8E,12E,16E,20E)-N-{2-[{4-[(2-amino-4-{[(3S)-1-hydroxyhexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]benzyl}(methyl)amino]ethyl}-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenamide or a pharmaceutically acceptable salt thereof.

17. The influenza vaccine according to claim 8 , wherein the universal influenza vaccine antigen is produced by subjecting an influenza HA split vaccine to an acidic treatment, and the substance which enhances the physiological activity of TLR7 is (4E,8E,12E,16E,20E)-N-{2-[{4-[(2-amino-4-{[(3S)-1-hydroxyhexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]benzyl}(methyl)amino]ethyl}-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenamide or a pharmaceutically acceptable salt thereof.

18. The kit according to claim 9 , wherein the universal influenza vaccine antigen is an influenza HA split vaccine antigen which produces an antibody that binds to a LAH of a HA stem region, and the substance which enhances the physiological activity of TLR7 is (4E,8E,12E,16E,20E)-N-{2-[{4-[(2-amino-4-{[(3S)-1-hydroxyhexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]benzyl}(methyl)amino]ethyl}-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenamide or a pharmaceutically acceptable salt thereof.

19. The kit according to claim 9 , wherein the universal influenza vaccine antigen is produced by subjecting an influenza HA split vaccine to an acidic treatment, and the substance which enhances the physiological activity of TLR7 is (4E,8E,12E,16E,20E)-N-{2-[{4-[(2-amino-4-{[(3S)-1-hydroxyhexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]benzyl}(methyl)amino]ethyl}-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenamide or a pharmaceutically acceptable salt thereof.

Assignments (4)
CORRECTIVE ASSIGNMENT TO CORRECT THE CITY NAME SHOULD READ "OSAKA-SHI, OSAKA" PREVIOUSLY RECORDED AT REEL: 060457 FRAME: 0066. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Mar 14, 2023
From: SUMITOMO DAINIPPON PHARMA CO., LTD.
To: SUMITOMO PHARMA CO., LTD.
Reel/Frame 063083/0246 →
CHANGE OF NAME Recorded Jul 7, 2022
From: SUMITOMO DAINIPPON PHARMA CO., LTD.
To: SUMITOMO PHARMA CO., LTD.
Reel/Frame 060457/0066 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2021
From: TAKAHASHI, YOSHIMASA; ADACHI, YU; ATO, MANABU
To: JAPAN AS REPRESENTED BY DIRECTOR GENERAL OF NATIONAL INSTITUTE OF INFECTIOUS DISEASES
Reel/Frame 055975/0551 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2021
From: FUKUSHIMA, AKIHISA
To: SUMITOMO DAINIPPON PHARMA CO., LTD.
Reel/Frame 055975/0657 →
Priority Claims (2)
JP 2018-138001 · Jul 23, 2018 · national
JP 2019-038976 · Mar 4, 2019 · national
Continuity (1)
Related Publication 20210353737A1 · Nov 18, 2021
Cited By (1)
US 12,491,240