# US 2018/0098962 A1 · Formulations of water-soluble derivatives of vitamin e and soft gel compositions, concentrates and powders containing same

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- Number: US 2018/0098962 A1
- Document ID: US20180098962A1
- Status: Published application
- Kind: A1
- Application number: 15/838,930
- Filed: 2017-12-12
- Published: 2018-04-12
- Earliest claimed: 2014-09-18
- Assignees: Virun, Inc.
- Applicants: Virun, Inc.
- Inventors: Philip J. Bromley
- Web page: https://patentgrep.com/patent/US20180098962A1

## CPC

- A61K 31/355: Tocopherols, e.g. vitamin E
- A61K 31/05: Phenols {(cannabinoids A61K31/658)}
- A61K 31/09: having two or more such linkages
- A61K 31/12: Ketones
- A61K 31/122: having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
- A61K 31/201: having one or two double bonds, e.g. oleic, linoleic acids
- A61K 31/202: having three or more double bonds, e.g. linolenic (eicosanoids, e.g. leukotrienes A61K31/557)
- A61K 31/231: having one or two double bonds
- A61K 31/36: Compounds containing methylenedioxyphenyl groups, e.g. sesamin
- A61K 31/385: having two or more sulfur atoms in the same ring
- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A61K 31/4745: condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines (yohimbine derivatives, vinblastine A61K31/475; ergoline derivatives A61K31/48)
- A61K 31/475: having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine (vincamine A61K31/4375)
- A61K 31/658: {o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol}
- A61K 31/685: one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
- A61K 36/324: Boswellia, e.g. frankincense
- A61K 36/82: Theaceae (Tea family), e.g. camellia
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- 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)

## Abstract

Provided herein are compositions that contain water-soluble vitamin E derivative mixtures (compositions), such as tocopheryl polyethylene glycol succinate (TPGS), TPGS analogs, TPGS homologs and TPGS derivatives. The water-soluble vitamin E mixtures contain mixtures of dimers and monomers of the vitamin E derivative. Provided are products containing the water-soluble vitamin E derivative mixtures, including capsules, soft gel compositions, pre-gel compositions, emulsions and powders.

## Claims

### Claim 1

A non-aqueous pre-gel composition, comprising:
a water-soluble vitamin E derivative mixture present in an amount from 1% to 99%, inclusive, by weight, of the composition, wherein:
the water-soluble vitamin E derivative is a polyalkylene glycol derivative of vitamin E; and
the water-soluble vitamin E derivative mixture comprises at least 13 wt % water-soluble vitamin E derivative dimer and up to 87% water-soluble vitamin E derivative monomer;
a non-polar compound or mixtures thereof other than the water-soluble vitamin E derivative mixture; and
an ingestible non-aqueous solvent that is insoluble or partially soluble in water.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the water-soluble vitamin E derivative is a polyethylene glycol (PEG) derivative of vitamin E.

### Claim 3 (depends on 2)

The composition of claim 2, wherein the PEG derivative of vitamin E is tocopheryl polyethylene glycol succinate (TPGS).

### Claim 4 (depends on 3)

The composition of claim 3, wherein the TPGS is TPGS-1000.

### Claim 5 (depends on 3)

The composition of claim 3, wherein the water-soluble vitamin E derivative mixture contains 29%-69%, inclusive, of dimer; and contains less than 70% of the vitamin E derivative monomer.

### Claim 6 (depends on 4)

The composition of claim 4, wherein the monomer comprises between or between about 35% and 65%, inclusive, by weight, of the water-soluble vitamin E derivative mixture and the dimer comprises between or between about 25% and 65%, by weight, of the water-soluble vitamin E derivative mixture.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the non-aqueous solvent is selected from among aromatic compounds, haloalkanes, ethers, esters and ketones, organic solvents of natural origin, alkyl ketones, tetrahydrofuran, cyclic alkyl amides, decylmethylsulfoxide, oleic acid, aromatic amines, natural oils, and acyl glycerols.

### Claim 8 (depends on 7)

The composition of claim 7, wherein the non-aqueous solvent is selected from among d-limonene, benzyl alcohol, benzyl benzoate, terpenes, alpha-pinene, beta-pinene, myrcene, linalol, citronellol, geraniol, menthol, citral, citronellal, N-methyl pyrrolidone (NMP), alkylene glycols, dimethyl sulfoxide, dimethyl acetamide, 2-pyrrolidone, C2-C6 alkanols, 2-ethoxyethanol, 2-ethoxyethyl acetate, methyl acetate, ethyl acetate, ethylene glycol diethyl ether, ethylene glycol dimethyl ether, (S)-(−)-ethyl lactate, acetone, glycerol, methylethyl ketone, dimethyl sulfone, tetrahydrofuran, caprolactam, decylmethylsulfoxide, oleic acid, N,N-diethyl-m-toluamide, 1-dodecylazacycloheptan-2-one, olive oils and fatty acids.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the amount of the non-aqueous solvent is at least 7%, up to and including 30%, by weight, of the composition.

### Claim 10 (depends on 3)

The composition of claim 3, comprising:
a non-aqueous solvent in an amount between 2% and 40%, or greater than 5%, up to 50%, inclusive, by weight, of the composition;
the polyethylene glycol (PEG) derivative of vitamin E mixture in an amount between 5% and 50%, inclusive, by weight, of the composition; and
a non-polar ingredient, other than the PEG derivative of vitamin E, in an amount between 10% and 90%, inclusive, by weight, of the composition.

### Claim 11 (depends on 1)

The composition of claim 1, wherein the non-aqueous solvent is an alcohol, an alcohol derivative, a hydrocarbon, or mixtures thereof.

### Claim 12 (depends on 11)

The composition of claim 11, wherein the non-aqueous solvent is selected from among benzyl alcohol, benzyl benzoate, d-limonene and mixtures thereof.

### Claim 13 (depends on 1)

The composition of claim 1, wherein the non-polar ingredient is or contains a non-polar compound selected from among polyunsaturated fatty acids (PUFAs), non-essential fatty acids, phospholipids, coenzyme Q compounds, flavonoids, carotenoids, micronutrients, Boswellia extracts, alkaloids, hops-containing compounds, antioxidants, and mixtures thereof.

### Claim 14 (depends on 1)

The composition of claim 1, wherein the non-polar compound is present in an amount of from between 40% and 90%, by weight, of the composition.

### Claim 15 (depends on 1)

A capsule composition, comprising a non-aqueous pre-gel composition of claim 1 in a shell or coating.

### Claim 16 (depends on 5)

A capsule composition, comprising a non-aqueous pre-gel composition of claim 5 in a shell or coating.

### Claim 17 (depends on 16)

The capsule composition of claim 16, wherein the non-aqueous solvent is an alcohol, an alcohol derivative, a hydrocarbon, or mixtures thereof.

### Claim 18 (depends on 17)

The capsule composition of claim 17, wherein the non-aqueous solvent is selected from among benzyl alcohol, benzyl benzoate, d-limonene, and mixtures thereof.

### Claim 19 (depends on 15)

The capsule composition of claim 15, wherein the shell or coating is a gelatin or gelatin substitute shell or coating.

### Claim 20 (depends on 1)

A method of making the pre-gel composition of claim 1, comprising:
a) mixing and heating ingredients in a vessel;
b) homogenizing the ingredients; and
c) cooling the mixed ingredients, whereby the mixed ingredients become a pre-gel liquid composition.

### Claim 21 (depends on 20)

The method of claim 20, further comprising introducing the pre-gel concentrate into a soft gel shell or capsule.

### Claim 22 (depends on 15)

A method of providing a non-polar compound to a subject, comprising administering a capsule of claim 15 to the subject.