# US 2018/0000850 A1 · Phospholipid compositions

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- Number: US 2018/0000850 A1
- Document ID: US20180000850A1
- Status: Published application
- Kind: A1
- Application number: 15/637,126
- Filed: 2017-06-29
- Published: 2018-01-04
- Earliest claimed: 2016-06-29
- Assignees: Machavert Pharmaceuticals LLC
- Applicants: Machavert Pharmaceuticals LLC
- Inventors: Jakub STASZAK-JIRKOVSKY; Lukas KOBR; Gregory F. MIKNIS; Colleen HUDSON; Luca MONFREGOLA,; Pavel JIRKOVSKY; Zboncåkovå MILADA; Jason DUEX; Pitchaimani KANDASAMY
- Web page: https://patentgrep.com/patent/US20180000850A1

## CPC

- A61K 31/688: both hydroxy compounds having nitrogen atoms, e.g. sphingomyelins
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 9/48: Preparations in capsules, e.g. of gelatin, of chocolate {(A61K9/0004 takes precedence; bite capsules A61K9/0056)}
- A61K 31/685: one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
- A61K 35/57: Birds; Materials from birds, e.g. eggs, feathers, egg white, egg yolk or endothelium corneum gigeriae galli
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61K 2236/00: Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compositions involving a modified egg yolk extract for use as an effective anti-cancer agent are described. The modified egg yolk extract involves specific fractions of phosphatidylcholines and sphingomyelins modified and produced from a chemical synthesis applied to the extract that produce a beneficial effect on the inhibition of cancerous cell growth. Methods of administering these compositions are also described.

## Claims

### Claim 1

A pharmaceutical composition comprising a plurality of bioactive phospholipids derived from hen egg yolk and one or more pharmaceutically acceptable diluents, excipients and/or carriers, wherein said plurality of bioactive phospholipids is substantially free of N-acyl ether phosphatidylethanolamines (NAEPE).

### Claim at position 2

2-5. (canceled)

### Claim 6 (depends on 1)

The pharmaceutical composition of claim 1, wherein said plurality of bioactive phospholipids further comprises compounds having the structure of formula (IIIa) and/or formula (IIIb):
wherein R10 is selected from hydrogen, methyl, or a C2-C18 acyl group;
R11 and R12 are independently selected from the group consisting of hydrogen or methyl, wherein if R10 is an acyl group, R11 or R12 is absent and the nitrogen bonded to R10 is uncharged;
R13 is independently hydrogen or a C2-C20 acyl group; and
pharmaceutically acceptable salts thereof.

### Claim at position 4

7-9. (canceled)

### Claim 10

A pharmaceutical composition comprising a plurality of bioactive phospholipids derived from egg yolk and one or more pharmaceutically acceptable diluents, excipients, and/or carriers, wherein said plurality of phospholipids is enriched in one or more lipids selected from the group consisting of:
(i) one or more phosphatidylethanolamine (PE) and/or phosphatidylcholine (PC) derivatives having the structure:
where R1 or R2 are independently selected from the group consisting of hydrogen, palmitoyl (C16:0), hexadecenoyl (C16:1), palmitoleoyl (C16:1), stearoyl (C18:0), octadecenoyl (C18:1), oleoyl (C18:1), octadecadienoyl (C18:2), linoleoyl (C18:2), α-linolenoyl (C18:3), octadecatrienoyl (C18:3), arachidonoyl (C20:4), eicosatetraenoyl (C20:4), docosapentaenoyl (C22:5), and docosahexaenoyl (C22:6) radicals;
R3 is selected from hydrogen, methyl, or a C2-C18 acyl group; wherein if R3 is an acyl group then the R4 or R5 is absent and the nitrogen bonded to R3 is uncharged;
R4 and R5 are independently selected from the group consisting of hydrogen or methyl, or pharmaceutically acceptable salts thereof; and/or
(ii) one or more sphingomyelin (SPH) derivatives having the structure
wherein R6 is palmitoyl (C16:0), stearoyl (C18:0), oleoyl (C18:1), tetradecanoyl (C14:0), heptadecanoyl (C17:0), nonadecanoyl (C19:0), eicosanoyl (C20:0), docosanoyl (C22:0), docosenoyl (C22:1), henicosanoyl (C23:0), tetracosadienoic (C24:2), or tetracosanoyl (C14:0); and pharmaceutically acceptable salts thereof.

### Claim 11

(canceled)

### Claim 12 (depends on 10)

The pharmaceutical composition according to claim 10, wherein R1 is selected from hydrogen, C16 or C18 fatty acid acyl radicals.

### Claim 13 (depends on 10)

The pharmaceutical composition according to claim 10, wherein R1 is selected from hydrogen, palmitoyl (C16:0), palmitoleoyl (C16:1), stearoyl (C18:0), and oleoyl (C18:1).

### Claim 14 (depends on 10)

The pharmaceutical composition according to claim 10, wherein R2 is selected from C18 fatty acid acyl radicals.

### Claim 15 (depends on 10)

The pharmaceutical composition according to claim 10, wherein R2 is selected from linoleoyl (C18:2) and oleoyl (C18:1).

### Claim 16 (depends on 10)

The pharmaceutical composition according to claim 10, wherein R3, R4, R5 are each methyl.

### Claim 17 (depends on 10)

The pharmaceutical composition according to claim 10, wherein said one or more phosphatidylcholine (PC) derivatives collectively comprise at least about 30% (w/w) of said plurality of phospholipids.

### Claim at position 13

18-20. (canceled)

### Claim 21 (depends on 10)

The pharmaceutical composition according claim 10, wherein said one or more sphingomyelin (SPH) derivatives collectively comprise between about 0.1% and 50% (w/w) of said plurality of phospholipids.

### Claim 22 (depends on 10)

The pharmaceutical composition according to claim 10, wherein R6 is palmitoyl (C16:0).

### Claim 23 (depends on 10)

The pharmaceutical composition according to claim 10, wherein said plurality of phospholipids is enriched in one or more phosphatidylcholine (PC) compounds and one or more sphingomyelin (SPH) compounds.

### Claim 24 (depends on 10)

The pharmaceutical composition according to claim 10, wherein said plurality of bioactive phospholipids is substantially free of N-acyl ether phosphatidylethanolamines (NAEPE).

### Claim at position 18

25-37. (canceled)

### Claim 38 (depends on 10)

The pharmaceutical composition according to claim 10, wherein R3-R5 are methyl, such that said plurality of bioactive phospholipids comprises a phosphatidylcholine (PC) component; wherein at least 50% (w/w) of said phosphatidylcholine (PC) component comprises one or more compounds selected from the group consisting of:
1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine,
1-palmitoyl-2-α-linolenoyl-sn-glycero-3-phosphocholine,
1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine,
1-linoleoyl-2-linoleoyl-sn-glycero-3-phosphocholine,
1-palmitoyl-2-docosahexaenoyl-sn-glycero-3-phosphocholine,
1-α-linolenoyl-2-docosahexaenoyl-sn-glycero-3-phosphocholine,
1-palmitoleoyl-2-oleoyl-sn-glycero-3-phosphocholine,
1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine,
1-palmitoyl-2-clupanodonoyl-sn-glycero-3-phosphocholine,
1-palmitoleoyl-2-docosahexaenoyl-sn-glycero-3-phosphocholine,
1-palmitoyl-2-osbondoyl-sn-glycero-3-phosphocholine,
1-oleoyl-2-arachidonoyl-sn-glycero-3-phosphocholine,
1-oleoyl-2-linoleoyl-sn-glycero-3-phosphocholine,
1,2-dioleoyl-sn-glycero-3-phosphocholine,
1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphocholine,
1-stearoyl-2-linoleoyl-sn-glycero-3-phosphocholine,
1-hydroxy-oleoyl-sn-glycero-3-phosphocholine
1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine, and
1-oleoyl-2-docosahexaenoyl-sn-glycero-3-phosphocholine;
and pharmaceutically acceptable salts thereof.

### Claim at position 20

39-86. (canceled)

### Claim 87 (depends on 1)

A method of treating a proliferative disease in a human patient in need thereof comprising administering to said patient a therapeutically effective amount of the pharmaceutical composition of claim 1.

### Claim 88 (depends on 87)

The method according to claim 87, wherein said proliferative disease is cancer.

### Claim 89 (depends on 87)

The method according to claim 87, wherein said proliferative disease is bladder, brain breast, cervical, colorectal, esophageal, kidney, liver, lung, ovarian, pancreatic, thyroid or uterine cancer.

### Claim 90 (depends on 87)

The method according to claim 87, wherein said therapeutically effective amount comprises from about 100 mg to about 10 g daily.

### Claim 91 (depends on 87)

The method according to claim 87, wherein said pharmaceutical composition is administered orally.

### Claim 92 (depends on 91)

The method according to claim 91, wherein said pharmaceutical composition is in the form of a capsule.

### Claim at position 27

93-103. (canceled)