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

Patent metadata

Field	Value
Publication number	US-10562839-B2
Application number	US-201916525437-A
Country	US
Kind code	B2
Filing date	Jul 29, 2019
Priority date	Jun 7, 2016
Publication date	Feb 18, 2020
Grant date	Feb 18, 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:

or a compound of Formula II:

Formula II, and salts, solvates or hydrates thereof, wherein:
R 4 is H or C(1-6) alkyl or substituted alkyl; and
R 5 and R 6 are independently unsubstituted or substituted C(4-30) alkyl.

2. The compound of claim 1 , wherein said compound comprises a compound of Formula II.

3. The compound of claim 2 , wherein R 4 is an unsubstituted C(1-6) alkyl.

4. The compound of claim 3 , wherein R 4 is methyl.

5. The compound of claim 2 , wherein R 5 and R 6 are independently unsubstituted C(6-18) alkyl.

6. The compound of claim 2 , wherein R 5 and R 6 are independently unsubstituted C6 alkyl or independently unsubstituted C8 alkyl.

7. The compound of claim 2 , wherein the compound is a compound of Formula IIa:

Formula IIa.

8. The compound of claim 2 , wherein the compound is a compound of Formula

Formula IIb.

9. The compound of claim 1 , wherein said compound is a compound having the formula:

10. The compound of claim 1 , wherein said compound is a compound having the formula:

11. The compound of claim 1 , wherein said compound is a compound having the formula:

12. The compound of claim 1 , wherein said compound is a compound having the formula:

13. The compound of claim 1 , wherein said compound is a compound having the formula:

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

15. The oral preparation of claim 14 , wherein said preparation comprises water.

16. The oral preparation of claim 15 , wherein said preparation comprises a syrup or an elixir.

17. The oral preparation of claim 15 , wherein said preparation comprises a suspension.

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

19. The oral preparation of claim 18 , 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.

20. The oral preparation of claim 14 , wherein said preparation comprises a flavoring agent.

21. The oral preparation of claim 20 , wherein said preparation comprises a flavoring agent selected from the group consisting of citric acid, menthol, glycine, and orange powder.

22. The oral preparation of claim 14 , wherein said preparation comprises a preservative.

23. The oral preparation of claim 22 , wherein said preparation comprises a preservative selected from the group consisting of sodium benzoate, sodium bisulflte, methylparaben, and propylparaben.

24. The oral preparation of claim 14 , wherein said compound comprises one or more compounds selected from the group consisting of

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

26. The ingestible composition of claim 25 , wherein said composition comprises a food supplemented with one or more of said compounds.

27. The ingestible composition of claim 25 , wherein said one or more compounds comprises one or more compounds selected from the group consisting of

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

29. The food supplement of claim 28 , wherein said food supplement comprises one or more additional components of a ketogenic diet.

30. The food supplement of claim 28 , wherein said compound comprises a compound selected from the group consisting of

Assignees

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

Inventors

• Verdin Eric
• Ulrich Scott Michael
• Newman John C

Classifications

• G02B1/04

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

• A61P25/28

  for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A23L33/12 Primary

  Fatty acids or derivatives thereof · CPC title

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title