Pharmaceutical composition and method of manufacturing

• US 10,639,339 B2
• Filed: 10/04/2018
• Issued: 05/05/2020
• Est. Priority Date: 04/17/2014
• Status: Active Grant

• Current Assignee: Avenir Wellness Solutions Incorporated
• Original Assignee: CURE Pharmaceutical Holding Corp.
• Inventors: Speier, Gary J.
• Primary Examiner(s): Meller, Michael V
• Application Number:
  US16/151,436
• Publication Number:
  US 20190030103A1
• Time in Patent Office: 579 Days
• Field of Search: 424725
• CPC Class Codes: A61K 2236/37 Extraction at elevated pressure or temperature, e.g. pressurized solvent extraction [PSE], supercritical carbon dioxide extraction or subcritical water extraction
• CPC Class Codes: A61K 31/352 condensed with carbocyclic rings, e.g. methantheline cannabinoids A61K31/658
• CPC Class Codes: A61K 36/00 Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines antigens from pollen A61K39/36
• CPC Class Codes: A61K 36/185 Magnoliopsida (dicotyledons)
• CPC Class Codes: A61K 9/006 Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
• CPC Class Codes: A61K 9/7023 Transdermal patches and similar drug-containing composite devices, e.g. cataplasms galenical aspects of iontophoretic devices A61K9/0009; microneedle arrays A61K9/0021; buccal patches A61K9/006
• CPC Class Codes: B01D 11/0203 with a supercritical fluid

Abstract

The present invention provides for methods of obtaining an extract of Cannabis plant material as well as subsequent processing of the extract to provide a concentrate of Cannabis. The present invention also provides for pharmaceutical dosage forms (e.g., oral thin films and transdermal patches) that include the concentrate (or extract) of Cannabis, as well as methods of medical treatment that include administering the pharmaceutical dosage forms.

Claims

1. A process for obtaining a concentrate of Cannabis sativa, Cannabis indica, or combinations thereof enriched with cannabigerolic acid, the process consisting essentially of:

(a) contacting Cannabis sativa, Cannabis indica, or combinations thereof with a supercritical fluid solvent consisting essentially of carbon dioxide, at a pressure of about 750 to about 3,000 psi, at a temperature of about −

20°

C. to about 70°

C., and for a period of time of about 1 to about 8 hours, to provide an extract of Cannabis sativa, Cannabis indica, or combinations thereof;

(b) removing the supercritical fluid solvent consisting essentially of carbon dioxide from the extract of Cannabis sativa, Cannabis indica, or combinations thereof; and

(c) isolating cannabigerolic acid from the extract of Cannabis sativa, Cannabis indica, or combinations thereof, to yield a concentrate of Cannabis sativa, Cannabis indica, or combinations thereof, enriched with cannabigerolic acid.

2. The process of claim 1, wherein the supercritical fluid solvent consists essentially of carbon dioxide and a second solvent selected from the group consisting of hydrogen, neon, nitrogen, argon, methane, ethane, propane, ammonia, water, xenon, methanol, ethanol, 1-propanol, 2-propanol, 1-hexanol, 2-methoxy ethanol, tetrahydrofuran, 1,4-dioxane, acetonitrile, methylene chloride, dichloroethane, chloroform, ethyl acetate, propylene carbonate, N,N-dimethylaceamide, dimethyl sulfoxide, formic acid, carbon disulfide, acetone, toluene, hexanes, pentanes, trifluoromethane, nitrous oxide, sulfur hexafluroide, butane, isobutane, ethyl ether, benzotrifluoride, p-(chlorophenyl)trifluoromethane, chlorofluorocarbon, hydrofluorocarbon, and combinations thereof.

3. The process of claim 1, wherein relative to the Cannabis sativa, Cannabis indica, or a combination thereof in step (a), the concentrate enriched with cannabigerolic acid contains at least about a 10% higher concentration of cannabigerolic acid.

4. The process of claim 1, wherein relative to the Cannabis sativa, Cannabis indica, or a combination thereof in step (a), the concentrate enriched with cannabigerolic acid contains at least about a 90% higher concentration of cannabigerolic acid.

5. The process of claim 1, wherein in step (c), the isolating of the cannabigerolic acid from the extract of Cannabis sativa, Cannabis indica, or combinations thereof is carried out by employing a technique selected from the group consisting of chromatography, adsorption, crystallization, distillation, liquid-liquid extraction, filtration, fractional distillation, precipitation, recrystallization, and sublimation.

6. The process of claim 1, wherein relative to the Cannabis sativa, Cannabis indica, or a combination thereof in step (a), the concentrate enriched with cannabigerolic acid contains a lower concentration of a component selected from the group consisting of:

(i) cannabinol,

(ii) alkaloids,

(iii) terpenes,

(iv) terpenoids,

(v) cannabinoid acids,

(vi) hemp oil, and

(vii) combinations thereof.

7. The process of claim 1, wherein relative to the Cannabis sativa, Cannabis indica, or a combination thereof in step (a), the concentrate enriched with cannabigerolic acid contains at least a 10% lower concentration of a component selected from the group consisting of:

(i) cannabinol,

(ii) alkaloids,

(iii) terpenes,

(iv) terpenoids,

(v) cannabinoid acids,

(vi) hemp oil, and

(vii) combinations thereof.

8. The process of claim 1, wherein relative to the Cannabis sativa, Cannabis indica, or a combination thereof in step (a), the concentrate enriched with cannabigerolic acid contains at least a 90% lower concentration of a component selected from the group consisting of:

(i) cannabinol,

(ii) alkaloids,

(iii) terpenes,

(iv) terpenoids,

(v) cannabinoid acids,

(vi) hemp oil, and

(vii) combinations thereof.

9. The process of claim 1, wherein the supercritical fluid solvent consists essentially of carbon dioxide as the only solvent.

10. The process of claim 1, wherein the concentrate enriched with cannabigerolic acid consists essentially of at least about 90 wt. % cannabigerolic acid.

11. A process for obtaining a concentrate of Cannabis sativa, Cannabis indica, or combinations thereof enriched with cannabigerolic acid, the process consisting essentially of:

(a) contacting Cannabis sativa, Cannabis indica, or combinations thereof with a supercritical fluid solvent consisting essentially of carbon dioxide, at a pressure of about 750 to about 3,000 psi, at a temperature of about −

20°

C. to about 70°

C., and for a period of time of about 1 to about 8 hours, to provide an extract of Cannabis sativa, Cannabis indica, or combinations thereof;

(b) removing the supercritical fluid solvent consisting essentially of carbon dioxide from the extract of Cannabis sativa, Cannabis indica, or combinations thereof; and

(c) isolating cannabigerolic acid from the extract of Cannabis sativa, Cannabis indica, or combinations thereof, to yield a concentrate of Cannabis sativa, Cannabis indica, or combinations thereof, enriched with cannabigerolic acid;

wherein,

relative to the Cannabis sativa, Cannabis indica, or a combination thereof in step (a), the concentrate enriched with cannabigerolic acid contains at least about a 10% higher concentration of cannabigerolic acid; and

relative to the Cannabis sativa, Cannabis indica, or a combination thereof in step (a), the concentrate enriched with cannabigerolic acid contains a lower concentration of a component selected from the group consisting of;

(i) cannabinol, (ii) alkaloids, (iii) terpenes, (iv) terpenoids, (v) cannabinoid acids, (vi) hemp oil, and (vii) combinations thereof.

12. The process of claim 11, wherein relative to the Cannabis sativa, Cannabis indica, or a combination thereof in step (a), the concentrate enriched with cannabigerolic acid contains at least about a 90% higher concentration of cannabigerolic acid.

13. The process of claim 11, wherein the supercritical fluid solvent consists essentially of carbon dioxide and a second solvent selected from the group consisting of hydrogen, neon, nitrogen, argon, methane, ethane, propane, ammonia, water, xenon, methanol, ethanol, 1-propanol, 2-propanol, 1-hexanol, 2-methoxy ethanol, tetrahydrofuran, 1,4-dioxane, acetonitrile, methylene chloride, dichloroethane, chloroform, ethyl acetate, propylene carbonate, N,N-dimethylaceamide, dimethyl sulfoxide, formic acid, carbon disulfide, acetone, toluene, hexanes, pentanes, trifluoromethane, nitrous oxide, sulfur hexafluroide, butane, isobutane, ethyl ether, benzotrifluoride, p-(chlorophenyl)trifluoromethane, chlorofluorocarbon, hydrofluorocarbon, and combinations thereof.

14. The process of claim 11, wherein in step (c), the isolating of the cannabigerolic acid from the extract of Cannabis sativa, Cannabis indica, or combinations thereof is carried out by employing a technique selected from the group consisting of chromatography, adsorption, crystallization, distillation, liquid-liquid extraction, filtration, fractional distillation, precipitation, recrystallization, and sublimation.

15. The process of claim 11, wherein relative to the Cannabis sativa, Cannabis indica, or a combination thereof in step (a), the concentrate enriched with cannabigerolic acid contains at least a 10% lower concentration of a component selected from the group consisting of:

(i) cannabinol,

(ii) alkaloids,

(iii) terpenes,

(iv) terpenoids,

(v) cannabinoid acids,

(vi) hemp oil, and

(vii) combinations thereof.

16. The process of claim 11, wherein relative to the Cannabis sativa, Cannabis indica, or a combination thereof in step (a), the concentrate enriched with cannabigerolic acid contains at least a 90% lower concentration of a component selected from the group consisting of:

(i) cannabinol,

(ii) alkaloids,

(iii) terpenes,

(iv) terpenoids,

(v) cannabinoid acids,

(vi) hemp oil, and

(vii) combinations thereof.

17. The process of claim 11, wherein the supercritical fluid solvent consists essentially of carbon dioxide as the only solvent.

18. The process of claim 11, wherein the concentrate enriched with cannabigerolic acid consists essentially of at least about 90 wt. % cannabigerolic acid.