IP Library Granted Patent US 10,039,734
Granted Patent B2
US 10,039,734 · App. 15/493,148 · Granted Aug 7, 2018

Eicosapentaenoic acid (EPA) formulations

Inventors: Brian J. Waibel (Kennett Square, PA); Hans Schonemann (Newburyport, MA); Val Krukonis (Lexington, MA); Michael Kagan (Jerusalem, IL)
Assignee: Qualitas Health, Ltd.
A61K31/202A23L33/12C07H15/06C11B3/006C12P7/6427
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Quick Facts
Patent No.
US 10,039,734
App. No.
15/493,148
Granted
Aug 7, 2018
Kind
B2
Abstract

Provided herein are compositions comprising eicosapentaenoic acid (EPA) and polar lipids (e.g., glycolipids and phospholipids), and which do not contain any docosahexaenoic acid (DHA) or esterified fatty acids.

Claims (105)

1. An EPA composition comprising from about 15 wt. % to about 90 wt. % eicosapentaenoic acid (EPA) and about 10 wt. % to about 70 wt. % polar lipids, wherein:

the polar lipids comprise phospholipid conjugates and glycolipid conjugates;

about 3 wt. % to about 50 wt. % of the EPA in the composition is a phospholipid conjugate;

about 5 wt. % to about 50 wt. % of the EPA in the composition is a glycolipid conjugate;

about 0 wt. % to about 10 wt. % of the EPA is a triglyceride conjugate or a diglyceride conjugate; the composition comprises between about 0.1 wt. % and about 3.0 wt. % mannitol and

the composition does not comprise docosahexaenoic acid (DHA), fatty acid methyl esters or fatty acid ethyl esters, and the composition is suitable for human consumption.

2. The composition of claim 1 , wherein about 15 wt. % to about 85 wt. % of the EPA in the composition is in free fatty acid form.

3. An EPA composition comprising following distribution of EPA by lipid class:

about 3 wt. % to about 50 wt. % of the EPA is a phospholipid conjugate;

about 5 wt. % to about 50 wt. % of the EPA is a glycolipid conjugate;

about 0 wt. % to about 10 wt. % of the EPA is a triglyceride conjugate or a diglyceride conjugate; and

about 15 wt. % to about 85 wt. % of the EPA is in free fatty acid form, wherein the composition does not comprise fatty acid methyl esters or fatty acid ethyl esters, and wherein the composition comprises between about 0.1 wt. % and about 3.0 wt. % mannitol and is suitable for human consumption.

4. The composition of claim 1 , wherein the EPA to total omega-3 fatty acids ratio is greater than 90%.

5. The composition of claim 1 , wherein the composition comprises about 15 wt. % to about 75 wt. % EPA.

6. The composition of claim 1 , wherein the composition comprises about 20 wt. % to about 50 wt. % EPA.

7. The composition of claim 1 , wherein the composition comprises at least about 13 wt. % polar lipids.

8. The composition of claim 1 , wherein the composition comprises at least about 13 wt. % polar lipids, less than 0.2 wt. % glyceride conjugates and at least about 30 wt. % free fatty acids.

9. The composition of claim 1 , wherein the polar lipids are comprised of phospholipid conjugates and glycolipid conjugates at a wt. % ratio in the range of about 3:1 to about 1:3.

10. The composition of claim 9 , wherein the glycolipid conjugates comprise one or more of digalactosyldiacylglycerol and monogalactosyldiacylglycerol.

11. The composition of claim 9 , wherein the phospholipid conjugates comprise one or more of phosphatidylcholine, lyso-phosphatidylcholine, phosphatidylinositol, phosphatidylethanolamine and phosphatidylglycerol.

12. The composition of claim 11 , wherein the phospholipid conjugates comprise one or more of phosphatidylcholine and phosphatidylglycerol.

13. The composition of claim 1 , wherein the composition comprises:

i) 0 to 5 wt. % C:18 fatty acids;

ii) 0 to 20 wt. % C:16 fatty acids;

iii) 0 to 5 wt. % C:14 fatty acids;

iv) 0 to 0.5 wt. % C:12 fatty acids; and/or

v) 0 to 0.5 wt. % C:10 fatty acids.

14. The composition of claim 1 , wherein the composition comprises chlorophyll a.

15. The composition of claim 1 , wherein the composition comprises less than about 10.0 wt. % arachidonic acid.

16. The composition of claim 1 , wherein the composition is substantially free of intact cells, cellular components, polynucleotides, and polypeptides.

17. The composition of claim 1 , wherein the composition comprises less than about 1 wt. % phytosterols.

18. The composition of claim 1 , wherein the composition comprises less than about 2 wt. % carotenoids.

19. The composition of claim 1 , wherein the composition does not comprise fatty acids selected from the group consisting of octadecatetraenoic acid or stearidonic acid (SDA=C18:4ω3), eicosatrienoic acid (ETE=C20:3ω3), eicosatetraenoic acid (ETA=C20:4ω3), heneicosapentaenoic acid or uncosapentaenoic acid (HPA=C21:5ω3), and docapentaenoic acid (DPA=C22:5ω3).

20. The composition of claim 1 , wherein the composition does not comprise one or more carotenoids selected from the group consisting of astaxanthin, cis-lutein, trans-lutein, cis-zeaxanthin, trans-alpha-crytoxanthin, trans-alpha-carotene, cis-alpha-carotene, cis-lycopene, and trans-lycopene.

21. The composition of claim 1 , wherein the composition does not comprise chlorophyll c.

22. The composition of claim 1 , wherein the composition does not comprise one or more phospholipids selected from the group consisting of N-acyl-phosphatidylethanolamine, lyso-phosphatidylcholine, phosphatidylinositol and phosphatidylethanolamine.

23. The composition of claim 1 , wherein the composition comprises about 20-50 wt. % EPA, about 10-25 wt. % glycolipids, and about 5-25 wt. % phospholipids.

24. The composition of claim 1 , wherein the composition comprises:

Component

wt. %

Fatty Acids

Capric (10:0)

0.1-0.2

Lauric (12:0)

0.1-0.2

Myristic (14:0)

1.0

Palmitic (16:0)

5.3-6.5

Palmitoleic (16:1)

7.0-8.0

Hexadecadienoic (16:2)

0.2-0.3

Stearic (18:0)

0.2-0.3

Oleic (18:1ω9)

2.0

Oleic (18:1ω7)

0.3-0.4

Linoleic (18:2ω6)

1.2-2.0

Alpha-Linolenic (ALA) (18:3ω3)

0.2

Arachidonic (20:4ω6)

1.0-8.0

Eicosapentaenoic (EPA) (20:5ω3)

19-30

Total Fatty Acid

40-55

Total Omega-3

20-30

EPA/Omega-3

>93   

Total Omega-6

 2-10

Phospholipids

Phosphatidylcholine

4.7-7.4

Lyso-Phosphatidylcholine

0.3-0.4

Phosphatidylinositol

0.8-1.3

Phosphatidylethanolamine

0.5-0.8

Phosphatidylglycerol

1.8-2.8

Glycolipids

Digalactosyldiacylglycerol

10-17

Monogalactosyldiacylglycerol

3-5

Phytonutrients

Phytosterols

1.5

Chlorophyll

4-5

Total Phospholipids (PL) (wt %)

 9-14

Total Glycolipids (GL) (wt %)

13-21

Total PoL (PL + GL) (wt %)

 22-35.

25. A capsule, tablet, solution, syrup, or suspension suitable for human consumption comprising a composition of claim 1 .

26. The capsule of claim 25 , wherein the capsule is a soft capsule.

27. A food, beverage, energy bar, or nutritional supplement comprising a composition of claim 1 .

Assignments (6)
RELEASE OF SECURITY INTEREST Recorded Mar 29, 2023
From: GP CAPITAL PARTNERS, LP
To: QUALITAS HEALTH INC.
Reel/Frame 063140/0981 →
RELEASE OF SECURITY INTEREST Recorded Dec 21, 2021
From: VIOLA CREDIT FIVE FUND, LIMITED PARTNERSHIP
To: QUALITAS HEALTH INC.
Reel/Frame 058448/0463 →
SECURITY INTEREST Recorded Dec 17, 2021
From: QUALITAS HEALTH INC.
To: GP CAPITAL PARTNERS, LP, AS AGENT
Reel/Frame 058415/0418 →
SECURITY INTEREST Recorded Feb 26, 2020
From: QUALITAS HEALTH INC.
To: VIOLA CREDIT FIVE FUND, LIMITED PARTNERSHIP
Reel/Frame 051937/0768 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2019
From: WAIBEL, BRIAN J.; SCHONEMANN, HANS; KRUKONIS, VAL; KAGAN, MICHAEL
To: QUALITAS HEALTH, LTD.
Reel/Frame 048792/0430 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2019
From: QUALITAS HEALTH, LTD.
To: QUALITAS HEALTH, INC.
Reel/Frame 048792/0545 →
Continuity (3)
Continuation 13797802 · Mar 12, 2013
Provisional Application 61745740 · Dec 24, 2012
Related Publication 20170304247A1 · Oct 26, 2017