Medium chain fatty acid esters of beta-hydroxybutyrate and butanediol and compositions and methods for using same

Patent metadata

Field	Value
Publication number	US-10647658-B2
Application number	US-201916528524-A
Country	US
Kind code	B2
Filing date	Jul 31, 2019
Priority date	Jun 7, 2016
Publication date	May 12, 2020
Grant date	May 12, 2020

Abstract

Aspects of the present disclosure include fatty acid β-hydroxyester compounds (e.g., fatty acid esters of β-hydroxybutyrate), fatty acid esters of butanediol, and pharmaceutically acceptable salts thereof. Also provided are pharmaceutical compositions having one or more fatty acid β-hydroxyester compounds and/or one or more fatty acid esters of butanediol. Methods for treating a subject by administering one or more esters to the subject are also provided. Kits containing one or more of the subject esters are also described.

First claim

What is claimed is:

1. A compound of the formula:

and salts, solvates or hydrates thereof, wherein:
R 1 is C(1-6) alkyl or substituted alkyl; and
R 2 and R 3 are independently unsubstituted or substituted C(4-30) alkyl.

2. The compound of claim 1 , wherein R 1 is an unsubstituted C(1-6) alkyl.

3. The compound of claim 2 , wherein R 1 is methyl.

4. The compound of claim 1 , wherein R 2 and R 3 are independently unsubstituted C(6-18) alkyl.

5. The compound of claim 4 , wherein R 2 and R 3 are independently unsubstituted C6 alkyl or independently unsubstituted C8 alkyl.

6. The compound of claim 1 , wherein the compound is a compound of Formula Ia:

7. The compound of claim 1 , wherein the compound is a compound of Formula Ib:

8. The compound of claim 6 , wherein said compound has the formula:

9. The compound of claim 6 , wherein said compound has the formula:

10. An oral preparation comprising one or more compounds of claim 1 and a preservative and/or a flavoring agent.

11. The oral preparation of claim 10 , wherein said preparation comprises water.

12. The oral preparation of claim 11 , wherein said preparation comprises a syrup or an elixir.

13. The oral preparation of claim 11 , wherein said preparation comprises a suspension.

14. The oral preparation of claim 10 , wherein said preparation comprises a binder.

15. The oral preparation of claim 14 , wherein said preparation comprises a binder selected from the group consisting of cellulose, methylcellulose, hydroxymethylcellulose, polypropylpyrrolidone, polyvinylpyrrolidone, gelatin, gum arabic, poly(ethylene glycol), sucrose, and starch.

16. The oral preparation of claim 10 , wherein said preparation comprises a flavoring agent.

17. The oral preparation of claim 16 , wherein said preparation comprises a flavoring agent selected from the group consisting of citric acid, menthol, glycine, and orange powder.

18. The oral preparation of claim 10 , wherein said preparation comprises a preservative.

19. The oral preparation of claim 18 , wherein said preparation comprises a preservative selected from the group consisting of sodium benzoate, sodium bisulflte, methylparaben, and propylparaben.

20. The oral preparation of claim 10 , wherein said compound comprises a compound having the formula:

21. The oral preparation of claim 10 , wherein said compound comprises a compound having the formula:

22. An ingestible composition comprising one or more compounds of claim 1 .

23. The ingestible composition of claim 22 , wherein said composition comprises a food supplemented with one or more of said.

24. The ingestible composition of claim 22 , wherein said one or more compounds comprises a compound having the formula:

25. The ingestible composition of claim 22 , wherein said one or more compounds comprises a compound having the formula:

26. A food supplement comprising one or more compounds of claim 1 .

27. The food supplement of claim 26 , wherein said food supplement comprises one or more additional components of a ketogenic diet.

28. The compound of claim 27 , wherein:
the compound is present in the composition in an amount of from about 1% w/w to about 25% w/w; and/or
the ketogenic diet comprises a ratio by mass of fat to protein and carbohydrates of from about 2:1 to about 10:1.

29. The food supplement of claim 26 , wherein said compound a compound having the formula:

30. The food supplement of claim 26 , wherein said compound a compound having the formula:

Assignees

• The J David Gladstone Inst
• Univ California
• Ithaca College

Inventors

• Verdin Eric
• Ulrich Scott Michael
• Newman John C

Classifications

• A61P13/12

  of the kidneys · CPC title

• A23V2200/322

  having an effect on the health of the nervous system or on mental function · CPC title

• A61P9/10

  for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• A23L33/12 Primary

  Fatty acids or derivatives thereof · CPC title