IP Library Granted Patent US 7,989,423
Granted Patent B2
US 7,989,423 · App. 12/625,048 · Granted Aug 2, 2011

6″-amino-6″-deoxygalactosylceramides

Assignees: The Scripps Research Institute; Brigham Young University; The University of Chicago
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Quick Facts
Patent No.
US 7,989,423
App. No.
12/625,048
Granted
Aug 2, 2011
Kind
B2
Abstract

This invention relates to galactosylceramide compounds.

Claims (34)

1. A method of stimulating the immune system of a subject in need of such stimulation, the method comprising administering a compound of Formula (I) to the subject wherein the compound of Formula (I) comprises:

wherein,

R 1 is —C(O)R 10 , wherein R 10 is C 1 -C 12 alkyl optionally substituted with carboxyl;

R 2 is hydrogen;

R 3 , R 4 , R 5 , R 6 and R 7 are each hydrogen;

R 8 is —(CH 2 ) x CH 3 ;

R 9 is a linear or branched C 3 -C 100 alkyl; and

x is 1-100.

2. A method of treating an autoimmune disease in a subject in need of such treatment, the method comprising administering an effective amount of a compound of Formula (I) to the subject wherein the compound of Formula (I) comprises:

wherein,

R 1 is —C(O)R 10 , wherein R 10 is C 1 -C 12 alkyl optionally substituted with carboxyl;

R 2 is hydrogen;

R 3 , R 4 , R 5 , R 6 and R 7 are each hydrogen;

R 8 is —(CH 2 ) x CH 3 ;

R 9 is a linear or branched C 3 -C 100 alkyl; and

x is 1-100; and

wherein the autoimmune disease is rheumatoid arthritis, systemic lupus erythematosus, Sjögren's syndrome, scleroderma, dermatomyositis, polymyositis, Reiter's syndrome, Behcet's disease, type I diabetes, type II diabetes, Hashimoto's thyroiditis, Graves' disease, multiple sclerosis, myasthenia gravis, encephalomyelitis, phemphigus, psoriasis, neurodermitis, or inflammatory bowel disease.

3. The method of claim 1 , wherein the subject is a mammal.

4. The method of claim 3 , wherein the subject is a human.

5. The method of claim 2 , wherein the subject is a mammal.

6. The method of claim 5 , wherein the subject is a human.

7. The method of claim 1 , wherein x is 24 and R 9 is n-tetradecyl.

8. The method of claim 1 , wherein R 10 is CH 3 .

9. The method of claim 8 , wherein R 9 is C 14 alkyl.

10. The method of claim 9 , wherein R 8 is —(CH 2 ) 24 —CH 3 .

11. The method of claim 9 , wherein R 8 is —(CH 2 ) 22 CH 3 .

12. The method of claim 1 , wherein R 10 is selected from —(CH 2 ) 2 COOH, —(CH 2 ) 3 COOH, and —(CH 2 ) 4 COOH.

13. The method of claim 2 , wherein x is 24 and R 9 is n-tetradecyl.

14. The method of claim 2 , wherein R 10 is CH 3 .

15. The method of claim 14 , wherein R 9 is C 14 alkyl.

16. The method of claim 14 , wherein R 8 is —(CH 2 ) 24 —CH 3 .

17. The method of claim 14 , wherein R 8 is —(CH 2 ) 22 CH 3 .

18. The method of claim 2 , wherein R 10 is selected from —(CH 2 ) 2 COOH, —(CH 2 ) 3 COOH, and —(CH 2 ) 4 COOH.

19. The method of claim 2 , wherein the autoimmune disease is type 1 diabetes, multiple sclerosis, rheumatoid arthritis, scleroderma, or inflammatory bowl disease.

Assignments (1)
CONFIRMATORY LICENSE Recorded Apr 18, 2017
From: BRIGHAM YOUNG UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 042276/0225 →
Continuity (2)
Division 10550165
Related Publication 20100137231A1 · Jun 3, 2010