# US 11,298,336 B2 · Water soluble formulation

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- Number: US 11,298,336 B2
- Document ID: US11298336B2
- Status: Granted
- Kind: B2
- Application number: 16/426,649
- Filed: 2019-05-30
- Published: 2020-12-03
- Granted: 2022-04-12
- Earliest claimed: 2019-05-30
- Assignees: Soluble Technologies LLC
- Applicants: Pankaj Modi
- Inventors: Pankaj Modi
- Web page: https://patentgrep.com/patent/US11298336B2

## CPC

- A61K 31/658: {o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol}
- A23L 2/52: Adding ingredients (adding preservatives A23B70/10)
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 9/0095: {Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches (A61K9/0007 takes precedence; eatable gels or foams A61K9/0056; oral mucosa adhesive forms A61K9/006)}
- A61K 9/107: Emulsions {; Emulsion preconcentrates; Micelles (composition of emulsions A61K47/00)}
- A61K 38/465: {acting on ester bonds (3.1), e.g. lipases, ribonucleases}
- A61K 47/12: Carboxylic acids; Salts or anhydrides thereof
- A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- A61K 47/20: containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
- A61K 47/22: Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- A61K 47/26: Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- A61K 47/36: Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K 47/44: Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin (synthetic glycerides, e.g. medium-chain triglycerides, A61K47/14)
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- 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)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

A formulation for solubilizing a water insoluble pharmaceutical agent is provided. The formulation comprises: a water-insoluble pharmaceutical agent, a detergent, an enzyme that breaks down lipids, proteins, and/or starches, a plasticizing agent, an emulsifying agent and an aqueous solvent. A method of making the formulation is also provided.

## Claims

### Claim 1

A formulation comprising: a water-insoluble pharmaceutical agent in an amount of 1%-50% by weight of the formulation, a detergent in an amount of 0.01% to 10% by weight, lipase in an amount of 0.01 to 10 wt %, a plasticizing agent in an amount of 0.01% to about 20% by weight, an emulsifying agent in an amount of 0.01% to about 20% by weight and an aqueous solvent as the balance of the formulation, wherein the pharmaceutical agent is solubilized or dissolved in the formulation.

### Claim 2 (depends on 1)

The formulation of claim 1, wherein the water-insoluble pharmaceutical agent is a cannabinoid or an analogue or salt thereof.

### Claim 3 (depends on 2)

The formulation of claim 2, wherein the cannabinoid is selected from the group consisting of cannabidiol (CBD), cannabinol (CBN), cannabichromene (CBC), cannabichromenic acid (CBCA), cannabidiolic acid (CBDA), cannabidivarin (CBDV), cannabigerol (CBG), cannabigerolic acid (CBGA), cannabigerivarin (CBGV), cannabidivarin acid (CBDVA), cannabinovarin (CBNV), cannabinodiol (CBDL), cannabicyclol (CBL), cannabielsoin (CBE), cannabitriol (CBT), cannabivarin (CBV), cannabichromevarin (CBCV), cannabigerol monoethyl ether (CBGM), tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), naphthoylindoles; phenylacetylindoles; benzoylindoles; cyclohexylphenoles; and pharmaceutically acceptable salts thereof.

### Claim 4 (depends on 1)

The formulation of claim 1, wherein the detergent comprises an ionic, non-ionic or zwitterionic detergent.

### Claim 5 (depends on 1)

The formulation of claim 1, wherein the lipase is selected from the group consisting of pancreatic lipase (PL), pancreatic lipase-related protein 1 (PLRP1), pancreatic lipase-related protein 2 (/PLRP2), hepatic lipase, endothelial lipase, lipoprotein lipase, lysosomal lipase, gastric lipase, lingual lipase and lipolase.

### Claim 6 (depends on 4)

The formulation of claim 4, wherein the detergent is selected from the group consisting of a bile acid or a salt thereof, and an aliphatic sulphate ester.

### Claim 7 (depends on 1)

The formulation of claim 1, comprising 0.01 to about 12 wt % of a saliva stimulating agent selected from citric acid, lactic acid, malic acid, succinic acid, ascorbic acid, adipic acid, fumaric acid, tartaric acid, and mixtures thereof.

### Claim 8 (depends on 1)

The formulation of claim 1, wherein the plasticizing agent is selected from triacetin, monoacetin, diacetin and mixtures thereof.

### Claim 9 (depends on 1)

The formulation of claim 1, comprising 0.01 to about 10 wt % of a stabilizing agent selected from xanthan gum, locust bean gum, guar gum, carrageenan and mixtures thereof.

### Claim 10 (depends on 1)

The formulation of claim 1, wherein the emulsifying agent is selected from triethanolamine stearate, a quaternary ammonium compound, acacia, gelatin, lecithin, bentonite, veegum, and mixtures thereof.

### Claim 11 (depends on 1)

The formulation of claim 1, which is an oral formulation.

### Claim 12 (depends on 11)

The formulation of claim 11, which is a beverage.

### Claim 13 (depends on 1)

The formulation of claim 1, wherein said formulation is an injectable formulation.

### Claim 14 (depends on 1)

The formulation of claim 1, additionally comprising a saliva stimulating agent.

### Claim 15 (depends on 1)

A method of making a formulation as defined in claim 1, comprising:
i) combining the pharmaceutical agent and the detergent with heat to form a clear emulsion in which the pharmaceutical agent is solubilized or dissolved;
ii) adding heated aqueous solvent to the clear emulsion to form a clear solution;
iii) adding to the clear solution an emulsion comprising the lipase, plasticizer and emulsifying agent; and
iv) stirring the emulsion of step iii) with the clear solution and allowing the solution to cool.

### Claim 16 (depends on 15)

The method of claim 15, wherein the pharmaceutical agent is a cannabinoid.

### Claim 17 (depends on 16)

The method of claim 16, wherein an aqueous solution of water-soluble ingredients is added to the clear solution in step ii).

### Claim 18 (depends on 17)

The method of claim 17, wherein the water-soluble ingredient is selected from the group consisting of sweeteners, flavouring agents, colouring agents and mixtures thereof.

### Claim 19 (depends on 16)

The method of claim 16, wherein the detergent comprises sodium lauryl sulfate and a polyoxyethylene detergent and the plasticizing agent is glycerin.

### Claim 20 (depends on 1)

The formulation of claim 1, wherein the detergent comprises sodium lauryl sulfate and a polyoxyethylene detergent and the plasticizing agent is glycerin.