IP Library › Granted Patent US 10,143,744
Granted Patent B2
US 10,143,744 · App. 15/006,938 · Granted Dec 4, 2018

Disaccharide synthetic lipid compounds and uses thereof

Inventors: Walter A Shaw (Birmingham, AL); Stephen W Burgess (Chelsea, AL); Shengrong Li (Birmingham, AL); David T Hickman (Saint-Sulpice, CH); Maria Pilar Lopez-Deber (Lausanne, CH)
Assignees: Avanti Polar Lipids, Inc; AC Immune SA
A61K39/39A61K39/0007C07H13/06A61K2039/55555A61K2039/55572A61K2039/57
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Quick Facts
Patent No.
US 10,143,744
App. No.
15/006,938
Granted
Dec 4, 2018
Kind
B2
Abstract

Essentially pure compounds of the formulas (I) to (XX) are provided. Compositions and methods for enhancing or stimulating an immune response are also provided. The compounds, provided are advantageous in that the compounds are essentially pure and free from contaminants encountered when such compounds are purified from natural sources.

Claims (143)

1. An essentially pure compound having the structure:

or a pharmaceutically acceptable salt thereof, wherein:

A 1 A 2 , and A 4 are each C 6 and A 3 and A 5 are each C 8 ;

A 1 A 2 , and A 4 are each C 7 and A 3 and A 5 are each C 9 ;

A 1 A 2 , and A 4 are each C 8 and A 3 and A 5 are each C 10 ;

A 1 A 2 , and A 4 are each C 9 and A 3 and A 5 are each C 11 ;

A 1 A 2 , and A 4 are each C 10 and A 3 and A 5 are each C 12 ;

A 1 A 2 , and A 4 are each C 12 and A 3 and A 5 are each C 14

A 1 A 2 , and A 4 are each C 13 and A 3 and A 5 are each C 15 ;

A 1 A 2 , and A 4 are each C 14 and A 3 and A 5 are each C 16 ;

A 1 A 2 , and A 4 are each C 15 and A 3 and A 5 are each C 17 ;

A 1 A 2 , and A 4 are each C 16 and A 3 and A 5 are each C 18 ;

A 1 A 2 , and A 4 are each C 17 and A 3 and A 5 are each C 19

A 1 A 2 , and A 4 are each C 6 and A 3 and A 5 are each C 7 ;

A 1 A 2 , and A 4 are each C 7 and A 3 and A 5 are each C 8 ;

A 1 A 2 , and A 4 are each C 8 and A 3 and A 5 are each C 9 ;

A 1 A 2 , and A 4 are each C 9 and A 3 and A 5 are each C 10 ;

A 1 A 2 , and A 4 are each C 10 and A 3 and A 5 are each C 11 ;

A 1 A 2 , and A 4 are each C 11 and A 3 and A 5 are each C 12 ;

A 1 A 2 , and A 4 are each C 12 and A 3 and A 5 are each C 13

A 1 A 2 , and A 4 are each C 13 and A 3 and A 5 are each C 14 ;

A 1 A 2 , and A 4 are each C 14 and A 3 and A 5 are each C 15 ;

A 1 A 2 , and A 4 are each C 15 and A 3 and A 5 are each C 16 ;

A 1 A 2 , and A 4 are each C 16 and A 3 and A 5 are each C 17 ;

A 1 A 2 , and A 4 are each C 17 and A 3 and A 5 are each C 18 ; or

A 1 A 2 , and A 4 are each C 18 and A 3 and A 5 are each C 19 .

2. The essentially pure compound of claim 1 , wherein

A 1 A 2 , and A 4 are each C 6 and A 3 and A 5 are each C 7 ;

A 1 A 2 , and A 4 are each C 7 and A 3 and A 5 are each C 8 ;

A 1 A 2 , and A 4 are each C 8 and A 3 and A 5 are each C 9 ;

A 1 A 2 , and A 4 are each C 9 and A 3 and A 5 are each C 10 ;

A 1 A 2 , and A 4 are each C 10 and A 3 and A 5 are each C 11 ;

A 1 A 2 , and A 4 are each C 11 and A 3 and A 5 are each C 12 ;

A 1 A 2 , and A 4 are each C 12 and A 3 and A 5 are each C 13

A 1 A 2 , and A 4 are each C 13 and A 3 and A 5 are each C 14 ;

A 1 A 2 , and A 4 are each C 14 and A 3 and A 5 are each C 15 ;

A 1 A 2 , and A 4 are each C 15 and A 3 and A 5 are each C 16 ;

A 1 A 2 , and A 4 are each C 16 and A 3 and A 5 are each C 17 ;

A 1 A 2 , and A 4 are each C 17 and A 3 and A 5 are each C 18 ; or

A 1 A 2 , and A 4 are each C 18 and A 3 and A 5 are each C 19 .

3. The essentially pure compound of claim 1 , wherein

A 1 A 2 , and A 4 are each C 6 and A 3 and A 5 are each C 8 ;

A 1 A 2 , and A 4 are each C 7 and A 3 and A 5 are each C 9 ;

A 1 A 2 , and A 4 are each C 8 and A 3 and A 5 are each C 10 ;

A 1 A 2 , and A 4 are each C 9 and A 3 and A 5 are each C 11 ;

A 1 A 2 , and A 4 are each C 10 and A 3 and A 5 are each C 12 ;

A 1 A 2 , and A 4 are each C 12 and A 3 and A 5 are each C 14

A 1 A 2 , and A 4 are each C 13 and A 3 and A 5 are each C 15 ;

A 1 A 2 , and A 4 are each C 14 and A 3 and A 5 are each C 16 ;

A 1 A 2 , and A 4 are each C 15 and A 3 and A 5 are each C 17 ;

A 1 A 2 , and A 4 are each C 16 and A 3 and A 5 are each C 18 ; or

A 1 A 2 , and A 4 are each C 17 and A 3 and A 5 are each C 19 .

4. The essentially pure compound of claim 1 , wherein the compounds is at least 95% pure with respect to the synthetic disaccharide lipid compounds as measured on a weight basis.

5. A pharmaceutical composition comprising:

a. a pharmaceutically acceptable carrier;

b. an optional antigen; and

c. an essentially pure compound of the formula

or a pharmaceutically acceptable salt thereof, wherein:

A 1 A 2 , and A 4 are each C 6 and A 3 and A 5 are each C 8 ;

A 1 A 2 , and A 4 are each C 7 and A 3 and A 5 are each C 9 ;

A 1 A 2 , and A 4 are each C 8 and A 3 and A 5 are each C 10 ;

A 1 A 2 , and A 4 are each C 9 and A 3 and A 5 are each C 11 ;

A 1 A 2 , and A 4 are each C 10 and A 3 and A S are each C 12 ;

A 1 A 2 , and A 4 are each C 12 and A 3 and A 5 are each C 14

A 1 A 2 , and A 4 are each C 13 and A 3 and A 5 are each C 15 ;

A 1 A 2 , and A 4 are each C 14 and A 3 and A 5 are each C 16 ;

A 1 A 2 , and A 4 are each C 15 and A 3 and A 5 are each C 17 ;

A 1 A 2 , and A 4 are each C 16 and A 3 and A 5 are each C 18 ;

A 1 A 2 , and A 4 are each C 17 and A 3 and A 5 are each C 19

A 1 A 2 , and A 4 are each C 6 and A 3 and A 5 are each C 7 ;

A 1 A 2 , and A 4 are each C 7 and A 3 and A 5 are each C 5 ;

A 1 A 2 , and A 4 are each C 8 and A 3 and A 5 are each C 9 ;

A 1 A 2 , and A 4 are each C 9 and A 3 and A 5 are each C 10 ;

A 1 A 2 , and A 4 are each C 10 and A 3 and A 5 are each C 11 ;

A 1 A 2 , and A 4 are each C 11 and A 3 and A 5 are each C 12 ;

A 1 A 2 , and A 4 are each C 12 and A 3 and A 5 are each C 13

A 1 A 2 , and A 4 are each C 13 and A 3 and A 5 are each C 14 ;

A 1 A 2 , and A 4 are each C 14 and A 3 and A 5 are each C 15 ;

A 1 A 2 , and A 4 are each C 15 and A 3 and A 5 are each C 16 ;

A 1 A 2 , and A 4 are each C 16 and A 3 and A 5 are each C 17 ;

A 1 A 2 , and A 4 are each C 17 and A 3 and A 5 are each C 18 ; or

A 1 A 2 , and A 4 are each C 18 and A 3 and A 5 are each C 19 .

6. The pharmaceutical composition of claim 5 , wherein

A 1 A 2 , and A 4 are each C 6 and A 3 and A 5 are each C 7 ;

A 1 A 2 , and A 4 are each C 7 and A 3 and A 5 are each C 8 ;

A 1 A 2 , and A 4 are each C 8 and A 3 and A 5 are each C 9 ;

A 1 A 2 , and A 4 are each C 9 and A 3 and A 5 are each C 10 ;

A 1 A 2 , and A 4 are each C 10 and A 3 and A 5 are each C 11 ;

A 1 A 2 , and A 4 are each C 11 and A 3 and A 5 are each C 12 ;

A 1 A 2 , and A 4 are each C 12 and A 3 and A 5 are each C 13

A 1 A 2 , and A 4 are each C 13 and A 3 and A 5 are each C 14 ;

A 1 A 2 , and A 4 are each C 14 and A 3 and A 5 are each C 15 ;

A 1 A 2 , and A 4 are each C 15 and A 3 and A 5 are each C 16 ;

A 1 A 2 , and A 4 are each C 16 and A 3 and A 5 are each C 17 ;

A 1 A 2 , and A 4 are each C 17 and A 3 and A 5 are each C 18 ; or

A 1 A 2 , and A 4 are each C 18 and A 3 and A 5 are each.

7. The pharmaceutical composition of claim 5 , wherein

A 1 A 2 , and A 4 are each C 6 and A 3 and A 5 are each C 8 ;

A 1 A 2 , and A 4 are each C 7 and A 3 and A 5 are each C 9 ;

A 1 A 2 , and A 4 are each C 8 and A 3 and A 5 are each C 10 ;

A 1 A 2 , and A 4 are each C 9 and A 3 and A 5 are each C 11 ;

A 1 A 2 , and A 4 are each C 10 and A 3 and A 5 are each C 12 ;

A 1 A 2 , and A 4 are each C 12 and A 3 and A 5 are each C 14

A 1 A 2 , and A 4 are each C 13 and A 3 and A 5 are each C 15 ;

A 1 A 2 , and A 4 are each C 14 and A 3 and A 5 are each C 16 ;

A 1 A 2 , and A 4 are each C 15 and A 3 and A 5 are each C 17 ;

A 1 A 2 , and A 4 are each C 16 and A 3 and A 5 are each C 18 ; or

A 1 A 2 , and A 4 are each C 17 and A 3 and A 5 are each C 19 .

8. The pharmaceutical composition of claim 5 , wherein the compounds is at least 95% pure with respect to the synthetic disaccharide lipid compounds as measured on a weight basis.

9. The pharmaceutical composition of claim 5 , wherein the composition comprises an antigen.

10. The pharmaceutical composition of claim 9 , wherein the pharmaceutically acceptable carrier is a liposome.

11. The pharmaceutical composition of claim 9 , wherein

A 1 A 2 , and A 4 are each C 6 and A 3 and A 5 are each C 8 ;

A 1 A 2 , and A 4 are each C 7 and A 3 and A 5 are each C 9 ;

A 1 A 2 , and A 4 are each C 8 and A 3 and A 5 are each C 10 ;

A 1 A 2 , and A 4 are each C 9 and A 3 and A 5 are each C 11 ;

A 1 A 2 , and A 4 are each C 10 and A 3 and A 5 are each C 12 ;

A 1 A 2 , and A 4 are each C 12 and A 3 and A 5 are each C 14

A 1 A 2 , and A 4 are each C 13 and A 3 and A 5 are each C 15 ;

A 1 A 2 , and A 4 are each C 14 and A 3 and A 5 are each C 16 ;

A 1 A 2 , and A 4 are each C 15 and A 3 and A 5 are each C 17 ;

A 1 A 2 , and A 4 are each C 16 and A 3 and A 5 are each C 18 ; or

A 1 A 2 , and A 4 are each C 17 and A 3 and A 5 are each C 19 .

12. The pharmaceutical composition of claim 5 , wherein the composition further comprises a second adjuvant.

13. The pharmaceutical composition of claim 12 , wherein the second adjuvant is a mono-phosphorylated hexaacyl disaccharide.

14. The pharmaceutical composition of claim 5 , wherein the composition is a vaccine composition.

15. The pharmaceutical composition of claim 5 , wherein the composition is useful in stimulating or enhancing an immune response in a subject.

16. The pharmaceutical composition of claim 5 , wherein the pharmaceutically acceptable carrier is a liposome.

17. The pharmaceutical composition of claim 5 , wherein the composition further comprises an antigen and a second adjuvant.

18. The pharmaceutical composition of claim 17 , wherein the second adjuvant is a mono-phosphorylated hexaacyl disaccharide.

19. The pharmaceutical composition of claim 17 , wherein the pharmaceutically acceptable carrier is a liposome.

20. The pharmaceutical composition of claim 17 , wherein

A 1 A 2 , and A 4 are each C 6 and A 3 and A 5 are each C 8 ;

A 1 A 2 , and A 4 are each C 7 and A 3 and A 5 are each C 9 ;

A 1 A 2 , and A 4 are each C 8 and A 3 and A 5 are each C 10 ;

A 1 A 2 , and A 4 are each C 9 and A 3 and A 5 are each C 11 ;

A 1 A 2 , and A 4 are each C 10 and A 3 and A 5 are each C 12 ;

A 1 A 2 , and A 4 are each C 12 and A 3 and A 5 are each C 14

A 1 A 2 , and A 4 are each C 13 and A 3 and A 5 are each C 15 ;

A 1 A 2 , and A 4 are each C 14 and A 3 and A 5 are each C 16 ;

A 1 A 2 , and A 4 are each C 15 and A 3 and A 5 are each C 17 ;

A 1 A 2 , and A 4 are each C 16 and A 3 and A 5 are each C 18 ; or

A 1 A 2 , and A 4 are each C 17 and A 3 and A 5 are each C 19 .

Assignments (2)
CHANGE OF NAME Recorded Aug 31, 2022
From: AVANTI POLAR LIPIDS, INC.
To: AVANTI POLAR LIPIDS, LLC
Reel/Frame 061364/0407 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 28, 2018
From: SHAW, WALTER A.; BURGESS, STEPHEN W.; LI, SHENGRONG; HICKMAN, DAVID T.; LOPEZ-DEBER, MARIA PILAR
To: AVANTI POLAR LIPIDS, INC.; AC IMMUNE SA
Reel/Frame 046726/0511 →
Continuity (3)
Continuation 13842424 · Mar 15, 2013
Provisional Application 61623393 · Apr 12, 2012
Related Publication 20160136271A1 · May 19, 2016