CANNABINOID FORMULATIONS

• US 20140302148A1
• Filed: 06/23/2014
• Published: 10/09/2014
• Est. Priority Date: 07/11/2011
• Status: Active Grant

• Current Assignee: Teewinot Technologies Limited (Teewinot Life Sciences Corp.)
• Original Assignee: Full Spectrum Laboratories Limited
• Inventors: WINNICKI, Robert
• Granted Patent: US 9,095,555 B2
• Time in Patent Office: Days
• US Class Current: 424/489
• CPC Class Codes: A23L 33/105 Plant extracts, their artificial duplicates or their derivatives
• CPC Class Codes: A23V 2002/00 Food compositions, function of food ingredients or processes for food or foodstuffs
• CPC Class Codes: A61K 31/05 Phenols cannabinoids A61K31/658
• CPC Class Codes: A61K 31/352 condensed with carbocyclic rings, e.g. methantheline cannabinoids A61K31/658
• CPC Class Codes: A61K 36/185 Magnoliopsida (dicotyledons)
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61K 47/10 Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
• CPC Class Codes: A61K 47/24 containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
• CPC Class Codes: A61K 47/36 Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
• CPC Class Codes: A61K 9/107 Emulsions ; Emulsion preconcentrates; Micelles composition of emulsions A61K47/00
• CPC Class Codes: A61K 9/1075 Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers A61K9/0026 takes precedence
• CPC Class Codes: A61K 9/127 Liposomes

Abstract

The present invention provides stable, fast-acting liposomal and micelle formulations of cannabinoids that are suitable for pharmaceutical and nutraceutical applications.

Claims

1. A stable, aqueous micelle suspension of one or more cannabinoids or cannabinoid analogues, wherein the stable aqueous micelle suspension of one or more cannabinoids or cannabinoid analogues does not comprise phospholipids and cholesterol.

2. The stable aqueous micelle suspension of of claim 1, wherein the average micelle diameter size in the aqueous micelle suspension of one or more cannabinoids or cannabinoid analogues is in a range between 50 and 1000 nm.

3. The stable aqueous micelle suspension of claim 1, wherein the concentration of cannabinoids or cannabinoid analogues in the aqueous micelle suspension from about 1.0 g/liter to about 10 g/liter.

4. The stable aqueous micelle suspension of claim 1, wherein the one or more cannabinoids or cannabinoid analogues are a natural compound, a synthetic compound, a semi-synthetic compound, or mixtures thereof.

5. The stable aqueous micelle suspension of claim 4, wherein the one or more cannabinoids or cannabinoid analogues are selected from the group consisting of cannabinol, cannabidiol, Δ

9-tetrahydrocannabinol, Δ

8-tetrahydrocannabinol, 11-hydroxy-tetrahydrocannabinol, 11-hydroxy-Δ

9-tetrahydrocannabinol, levonantradol, Δ

11-tetrahydrocannabinol, tetrahydrocannabivarin, dronabinol. amandamide, nabilone, a combination thereof, a natural or synthetic analogue thereof, and a natural or synthetic molecule with a basic cannabinoid structure.

6. The stable aqueous micelle suspension of claim 1, further comprising a stabilizer selected from the group consisting of guar gum, xyanthan gum cellulose hyaluronic acid, polyvinyl pyrrolidone (PVP), alginate, chondritin sulfate, poly gamma glutamic acid, gelatin, chitisin, corn starch and flour, in an amount from about 0.25% to about 2% (w/v).

30. The stable, aqueous micelle suspension of claim 1, wherein the suspension comprises unilamellar micelles that are thermostable at temperatures greater than 50°

C.

31. The stable, aqueous micelle suspension of claim 1, further comprising a pharmaceutically active compound or a drug selected from the group consisting of chemotherapeutic agents, immunosuppressive agents, immune-stimulatory agents, anti-inflammatory agents, anti-depressive agents, pro-drugs and antibiotics.

7. A method of producing a stable aqueous micelle suspension of one or more cannabinoids or cannabinoid analogues devoid of phospholipids and cholesterol comprising the steps of:

(a) dissolving one or more cannabinoids or cannabinoid analogues in ethanol to obtain an ethanol cannabinoid solution;

(b) injecting the ethanol cannabinoid solution into distilled water to obtain a micelle cannabinoid aqueous suspension; and

(c) removing the ethanol from the cannabinoid aqueous suspension thereby producing a stable aqueous micelle suspension of one or more cannabinoids or cannabinoid analogues;

wherein the aqueous micelle suspension of one or more cannabinoids or cannabinoid analogues does not contain phospholipids and cholesterol; and

wherein the aqueous micelle suspension of one or more cannabinoids or cannabinoid analogues shows no aqueous core under oil immersion microscopy.

8. The method of claim 7, wherein the average micelle diameter size in the aqueous micelle suspension is in a range between 50 and 1000 nm, and wherein the concentration of cannabinoids or cannabinoid analogues in the aqueous micelle suspension from about 1.0 g/liter to about 10 g/liter.

9. The method of claim 7, wherein the one or more cannabinoids or cannabinoid analogues are a natural compound, a synthetic compound, a semi-synthetic compound, or mixtures thereof.

10. The method of claim 9, wherein the one or more cannabinoids or cannabinoid analogues are selected from the group consisting of cannabinol, cannabidiol, Δ

9-tetrahydrocannabinol, Δ

8-tetrahydrocannabinol, 11-hydroxy-tetrahydrocannabinol, 11-hydroxy-Δ

9-tetrahydrocannabinol, levonantradol, Δ

11-tetrahydrocannabinol, tetrahydrocannabivarin, dronabinol, amandamide, nabilone, a combination thereof, a natural or synthetic analogue thereof, and a natural or synthetic molecule with a basic cannabinoid structure.

11-21. -21. (canceled)

22. An aqueous cannabinoid solution comprising one or more cannabinoids or cannabinoid analogues in an amount of 50 g/liter.

23. The aqueous cannabinoid solution of claim 22, wherein the cannabinoid solution is in form of a fast-acting pharmaceutical composition, a fast-acting nutraceutical composition, or a fast-acting food or beverage for administration to a subject.

24. The aqueous cannabinoid solution of claim 23, wherein the food is a soup, a baking good, a dairy product, a meat product, a fish product, a vegetable product or a fruit product.

25. The aqueous cannabinoid solution of claim 23, wherein the fast-acting compositions, food or beverage are formulated for oral, enteral, parenteral, intravenous, pulmonary, mucosal, sub-mucosal or topical administration.

26. A method of alleviating pain or reducing undesirable side effects associated with radiation therapy or chemotherapy in a subject in need thereof comprising administering to the subject the aqueous cannabinoid solution of claim 24.

27. The method of claim 26, wherein the subject has a compromised immune system, a cancer, a pulmonary disease or a condition that causes violent tremors.

28. The method of claim 26, wherein the aqueous cannabinoid solution is administered in a combination therapy prior to, simultaneously with or following administration of a pharmaceutically active compound or a drug.

29. The method of claim 28, wherein the pharmaceutically active compound or drug is selected from the group consisting of chemotherapeutic agents, immunosuppressive agents, immune-stimulatory agents, anti-inflammatory agents, anti-depressive agents, pro-drugs and antibiotics.

32. A method for producing the aqueous cannabinoid solution of claim 22 comprising rapidly dissolving a cannabinoid extract in water in the presence of a stabilizing agent, wherein the stabilizing agent is a polymer, cellulose hyaluronic acid, polyvinylpyrrolidone (PVP), alginate, chondroitin sulfate, poly gamma glutamic acid, gelatin, chitisin, corn starch or flour.