IP Library Granted Patent US 11,944,598
Granted Patent B2
US 11,944,598 · App. 18/218,519 · Granted Apr 2, 2024

Compositions containing s-beta-hydroxybutyrate or non-racemic mixtures enriched with the s-enatiomer

Inventor: Gary Millet (Salt Lake City, UT)
Assignee: AXCESS GLOBAL SCIENCES, LLC
A61K31/22A61K9/0053A61K31/047A61K31/19A23V2200/3322
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Quick Facts
Patent No.
US 11,944,598
App. No.
18/218,519
Granted
Apr 2, 2024
Kind
B2
Abstract

Beta-hydroxybutyrate compositions include a mixture of optically pure S-beta-hydroxybutyrate salts and acid(s) or non-racemic mixture of beta-hydroxybutyrate salts and acid(s) enriched with the S-enantiomer. The S-beta-hydroxybutyrate enantiomer modulates the effect of ketone bodies in the subject and controls the rate at which ketosis is achieved. Beta-hydroxybutyric acid is more rapidly absorbed and utilized by the body than salts or esters, enhances taste, and reduces the need to include citric acid or other edible acids. Beta-hydroxybutyrate salts are more slowly absorbed and utilized by the body and can provide one or more electrolytes. Compositions for controlling ketone body level in a subject may contain a dietetically or pharmaceutically acceptable carrier and optically pure S-beta-hydroxybutyrate or non-racemic mixture enriched with S-beta-hydroxybutyrate, wherein the compositions contain greater than 50% up to 100% by enantiomeric equivalents of S-beta-hydroxybutyrate and less than 50% down to 0% by enantiomeric equivalents of R-beta-hydroxybutyrate.

Claims (31)

1. A composition for administering S-beta-hydroxybutyrate to a subject, comprising:

greater than 50% by enantiomeric equivalents of S-beta-hydroxybutyrate and less than 50% by enantiomeric equivalents of R-beta-hydroxybutyrate,

wherein the S-beta-hydroxybutyrate includes S-beta-hydroxybutyric acid and at least one of S-beta-hydroxybutyrate salt or S-beta-hydroxybutyrate ester,

wherein the R-beta-hydroxybutyrate, when present, includes at least one of R-beta-hydroxybutyric acid, R-beta-hydroxybutyrate salt, or R-beta-hydroxybutyric ester.

2. The composition of claim 1 , wherein the S-beta-hydroxybutyrate comprises the S-beta-hydroxybutyric acid and at least one S-beta-hydroxybutyrate salt.

3. The composition of claim 2 , wherein the composition comprises at least 20% by molar equivalents of one or more S-beta-hydroxybutyrate salts and optionally one or more R-beta-hydroxybutyrate salts and less than 80% by molar equivalents of S-beta-hydroxybutyric acid and optionally R-beta-hydroxybutyric acid.

4. The composition of claim 2 , wherein the composition comprises at least 40% by molar equivalents of one or more S-beta-hydroxybutyrate salts and optionally one or more R-beta-hydroxybutyrate salts and less than 60% by molar equivalents of S-beta-hydroxybutyric acid and optionally R-beta-hydroxybutyric acid.

5. The composition of claim 1 , wherein the composition comprises a greater amount by molar equivalents of one or more S-beta-hydroxybutyrate salts and optionally one or more R-beta-hydroxybutyrate salts than molar equivalents of S-beta-hydroxybutyric acid and optionally R-beta-hydroxybutyric acid.

6. The composition of claim 1 , wherein the S-beta-hydroxybutyrate comprises the S-beta-hydroxybutyric acid and at least one S-beta-hydroxybutyrate ester.

7. The composition of claim 1 , wherein the composition is in a dosage form that provides about 0.5 g to about 25 g of beta-hydroxybutyrate.

8. The composition of claim 1 , wherein the composition comprises a non-racemic mixture containing 50.5% to 99.5% by enantiomeric equivalents of S-beta-hydroxybutyrate and 49.5% to 0.5% by enantiomeric equivalents of R-beta-hydroxybutyrate.

9. The composition of claim 1 , wherein the composition comprises at least one lithium, sodium, potassium, calcium, magnesium, or amino acid salt of S-beta-hydroxybutyrate.

10. The composition of claim 1 , further comprising at least one of a vitamin, mineral, nootropic, herbal supplement, short chain fatty acid, or short chain fatty acid ester.

11. A composition for administering S-beta-hydroxybutyrate to a subject, comprising:

greater than 50% by enantiomeric equivalents of S-beta-hydroxybutyrate and less than 50% by enantiomeric equivalents of R-beta-hydroxybutyrate, wherein the S-beta-hydroxybutyrate comprises at least one of S-beta-hydroxybutyric acid or S-beta-hydroxybutyrate salt,

wherein the composition is provided as or in a tablet, capsule, powder, food product, food additive, flavored beverage, vitamin fortified beverage, non-alcoholic beverage, flavored beverage additive, vitamin fortified beverage additive, non-alcoholic beverage additive, candy, sucker, pastille, food supplement, flavored mouth spray, or suppository.

12. The composition of claim 11 , wherein the S-beta-hydroxybutyrate comprises S-beta-hydroxybutyric acid and at least one S-beta-hydroxybutyrate salt.

13. The composition of claim 12 , wherein the composition comprises at least 20% by molar equivalents of one or more S-beta-hydroxybutyrate salts and optionally one or more R-beta-hydroxybutyrate salts and less than 80% by molar equivalents of S-beta-hydroxybutyric acid and optionally R-beta-hydroxybutyric acid.

14. The composition of claim 11 , wherein the composition contains from 50.5% to 99.5% by enantiomeric equivalents of S-beta-hydroxybutyrate and 49.5% to 0.5% by enantiomeric equivalents of R-beta-hydroxybutyrate.

15. The composition of claim 11 , wherein the composition is in a dosage form that provides about 0.5 g to about 25 g of beta-hydroxybutyrate.

16. A composition for administering S-beta-hydroxybutyrate to a subject, comprising:

a dietetically or pharmaceutically acceptable carrier selected from the group consisting of tablet, capsule, powder, food product, food additive, flavored beverage, vitamin fortified beverage, non-alcoholic beverage, flavored beverage additive, vitamin fortified beverage additive, non-alcoholic beverage additive, candy, sucker, pastille, food supplement, flavored mouth spray, and suppository; and

greater than 50% by enantiomeric equivalents of S-beta-hydroxybutyrate and less than 50% by enantiomeric equivalents of R-beta-hydroxybutyrate, wherein the S-beta-hydroxybutyrate comprises at least one of S-beta-hydroxybutyric acid or S-beta-hydroxybutyrate salt.

17. The composition of claim 16 , wherein the S-beta-hydroxybutyrate comprises S-beta-hydroxybutyric acid and optionally at least one S-beta-hydroxybutyrate salt.

18. The composition of claim 17 , wherein the composition comprises at least 20% by molar equivalents of one or more S-beta-hydroxybutyrate salts and optionally one or more R-beta-hydroxybutyrate salts and less than 80% by molar equivalents of S-beta-hydroxybutyric acid and optionally R-beta-hydroxybutyric acid.

19. The composition of claim 16 , wherein the composition contains from 50.5% to 99.5% by enantiomeric equivalents of S-beta-hydroxybutyrate and 49.5% to 0.5% by enantiomeric equivalents of R-beta-hydroxybutyrate.

20. The composition of claim 16 , wherein the composition is in a dosage form that provides about 0.5 g to about 25 g of beta-hydroxybutyrate.

21. A composition for administering S-beta-hydroxybutyrate to a subject, comprising:

greater than 50% by enantiomeric equivalents of S-beta-hydroxybutyrate and less than 50% by enantiomeric equivalents of R-beta-hydroxybutyrate,

wherein the composition is in a dosage form that provides about 0.5 g to about 25 g of beta-hydroxybutyrate.

22. The composition of claim 21 , wherein the S-beta-hydroxybutyrate comprises S-beta-hydroxybutyric acid and optionally at least one of a S-beta-hydroxybutyrate salt or S-beta-hydroxybutyrate ester.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 5, 2023
From: MILLET, GARY
To: AXCESS GLOBAL SCIENCES, LLC
Reel/Frame 064158/0102 →
Continuity (8)
Continuation In Part 17555724 · Dec 20, 2021
Continuation 17130498 · Dec 22, 2020
Continuation In Part 16783886 · Feb 6, 2020
Continuation In Part 16272192 · Feb 11, 2019
Continuation In Part 16224485 · Dec 18, 2018
Division 15936849 · Mar 27, 2018
Provisional Application 62607578 · Dec 19, 2017
Related Publication 20230338321A1 · Oct 26, 2023
Cited By (13)
US 12,186,297 US 12,251,362 US 12,329,734 US 12,350,243 US 12,433,912 US 12,496,283 US 12,514,841 US 12,521,378 US 12,533,331 US 12,533,346 US 12,551,455 US 12,599,579 US 12,622,889