IP Library › Granted Patent US 11,938,160
Granted Patent B2
US 11,938,160 · App. 18/048,954 · Granted Mar 26, 2024

Pharmaceutical composition and method of manufacturing

Inventor: Gary J. Speier (Eden Prairi, MN)
A61K36/185A61K9/006A61K9/7023A61K31/05A61K31/352A61K36/00B01D11/0407A61K2236/00
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Quick Facts
Patent No.
US 11,938,160
App. No.
18/048,954
Granted
Mar 26, 2024
Kind
B2
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 (33)

1. A process for obtaining a first extract of Cannabis sativa, Cannabis indica , or combination thereof, enriched with at least one of: cannabinol; cannabinolic acid; Δ(9)-tetrahydrocannabinolic acid; Δ(9)-cannabidiol; Δ(9)-tetrahydrocannabidiolic acid; Δ(8)-tetrahydrocannabinolic acid; Δ(8)-tetrahydrocannabidiol; Δ(8)-tetrahydrocannabidiolic acid; Δ(9)-tetrahydrocannabivarin; cannabigerol; cannabigerolic acid; cannabichromene; cannabichromenic acid; cannabicyclol; and cannabicyclolic acid, and

a second extract of Cannabis sativa, Cannabis indica , or combination thereof, enriched with at least one of Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol, the process comprising:

(a) contacting Cannabis sativa, Cannabis indica , or a combination thereof, with carbon dioxide as the sole supercritical fluid solvent, at a pressure of 1,600 psi to 3,800 psi, at a temperature of 44° C. to 54° C., for a period of time of 2 hours to 8 hours, to provide an enriched extract of Cannabis sativa, Cannabis indica , or combination thereof; and

(b) removing the supercritical carbon dioxide from the extract; wherein the (a) contacting of the Cannabis sativa, Cannabis indica , or a combination thereof, with the supercritical carbon dioxide and then the (b) removing the supercritical carbon dioxide, is carried out two or more times, such that the process is a supercritical carbon dioxide fluid extraction;

wherein a first supercritical carbon dioxide fluid extraction is carried out such that:

(i) the contacting of the Cannabis sativa, Cannabis indica , or a combination thereof, with the supercritical carbon dioxide, is carried out at a pressure of 1,600 psi to 2,000 psi, at a temperature of 44° C. to 54° C., for a period of time of 2 hours to 4 hours, to provide the first extract;

wherein a second supercritical carbon dioxide fluid extraction is carried out such that:

(i) the contacting of the Cannabis sativa, Cannabis indica , or a combination thereof, with the supercritical carbon dioxide, is carried out at a pressure of 2,250 psi to 3,800 psi, at a temperature of 44° C. to 54° C., for a period of time of 4 hours to 8 hours, to provide the second extract.

2. The process of claim 1 , wherein the first extract comprises no more than 10 wt. % in the aggregate Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol.

3. The process of claim 1 , wherein the first extract comprises no more than 5 wt. % in the aggregate Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol.

4. The process of claim 1 , wherein the first extract comprises no more than 1 wt. % in the aggregate Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol.

5. The process of claim 1 , wherein the first extract is purified employing a technique selected from the group consisting of chromatography, adsorption, crystallization, distillation, liquid-liquid extraction, filtration, fractional distillation, precipitation, recrystallization, lyophilization, sublimation, and combinations thereof.

6. The process of claim 1 , wherein the first extract is purified employing a technique selected from the group consisting of chromatography, adsorption, crystallization, distillation, liquid-liquid extraction, filtration, fractional distillation, precipitation, recrystallization, lyophilization, sublimation, and combinations thereof; such that the first extract after the purification comprises at least 85 wt. % cannabinoids comprising at least one of cannabinolic acid; Δ(9)-tetrahydrocannabinolic acid; Δ(9)-cannabidiol; Δ(9)-tetrahydrocannabidiolic acid; Δ(8)-tetrahydrocannabinolic acid; Δ(8)-tetrahydrocannabidiol; Δ(8)-tetrahydrocannabidiolic acid; Δ(9)-tetrahydrocannabivarin; cannabigerol; cannabigerolic acid; cannabichromene; cannabichromenic acid; cannabicyclol; and cannabicyclolic acid.

7. The process of claim 1 , wherein the first extract is purified employing a technique selected from the group consisting of chromatography, adsorption, crystallization, distillation, liquid-liquid extraction, filtration, fractional distillation, precipitation, recrystallization, lyophilization, sublimation, and combinations thereof; such that the first extract after the purification comprises at least 98 wt. % cannabinoids comprising at least one of cannabinol; cannabinolic acid; Δ(9)-tetrahydrocannabinolic acid; Δ(9)-cannabidiol; Δ(9)-tetrahydrocannabidiolic acid; Δ(8)-tetrahydrocannabinolic acid; Δ(8)-tetrahydrocannabidiol; Δ(8)-tetrahydrocannabidiolic acid; Δ(9)-tetrahydrocannabivarin; cannabigerol; cannabigerolic acid; cannabichromene; cannabichromenic acid; cannabicyclol; and cannabicyclolic acid.

8. The process of claim 1 , wherein relative to the Cannabis in step (a), the first extract includes a lower concentration of Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol.

9. The process of claim 1 , wherein the first extract comprises no more than 10 wt. % in the aggregate of Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol.

10. The process of claim 1 , wherein the first extract comprises no more than 5 wt. % in the aggregate of Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol.

11. The process of claim 1 , wherein the first extract comprises no more than 1 wt. % in the aggregate of Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol.

12. The process of claim 1 , wherein the second extract is purified employing a technique selected from the group consisting of chromatography, adsorption, crystallization, distillation, liquid-liquid extraction, filtration, fractional distillation, precipitation, recrystallization, lyophilization, sublimation, and combinations thereof.

13. The process of claim 2 , wherein the second extract is purified employing a technique selected from the group consisting of chromatography, adsorption, crystallization, distillation, liquid-liquid extraction, filtration, fractional distillation, precipitation, recrystallization, lyophilization, sublimation, and combinations thereof; such that the second extract enriched with Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol after the purification comprises at least 85 wt. % in the aggregate of Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol.

14. The process of claim 1 , wherein the second extract is purified employing a technique selected from the group consisting of chromatography, adsorption, crystallization, distillation, liquid-liquid extraction, filtration, fractional distillation, precipitation, recrystallization, lyophilization, sublimation, and combinations thereof; such that the second extract enriched with Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol after the purification comprises at least 95 wt. % in the aggregate of Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol.

15. The process of claim 1 , further comprising removing the supercritical fluid solvent from the second extract.

16. The process of claim 1 , wherein the second extract comprises at least about 65 wt. % in the aggregate of Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol.

17. The process of claim 1 , wherein relative to the Cannabis in step (a), the second extract includes a lower concentration of cannabinoids comprising cannabinol; cannabinolic acid; Δ(9)-tetrahydrocannabinolic acid; Δ(9)-cannabidiol; Δ(9)-tetrahydrocannabidiolic acid; Δ(8)-tetrahydrocannabinolic acid; Δ(8)-tetrahydrocannabidiol; Δ(8)-tetrahydrocannabidiolic acid; Δ(9)-tetrahydrocannabivarin; cannabigerol; cannabigerolic acid; cannabichromene; cannabichromenic acid; cannabicyclol; cannabicyclolic acid; and combinations thereof.

18. The process of claim 1 , wherein relative to the Cannabis in step (a), the second extract includes a lower concentration of cannabigerolic acid.

19. The process of claim 1 , wherein relative to the Cannabis in step (a), the second extract includes a lower concentration of cannabinol.

20. The process of claim 1 , wherein relative to the Cannabis in step (a), the second extract includes a lower concentration of Δ(9)-tetrahydrocannabinolic acid.

21. The process of claim 1 , wherein relative to the Cannabis in step (a), the second extract includes a lower concentration of Δ(9)-cannabidiol.

22. The process of claim 1 , wherein relative to the Cannabis in step (a), the second extract includes a lower concentration of Δ(9)-tetrahydrocannabidiolic acid.

23. The process of claim 1 , wherein the relative to the Cannabis in step (a), the second extract includes a higher concentration of Δ(8)-tetrahydrocannabinol.

24. The process of claim 1 , wherein relative to the Cannabis in step (a), the second extract includes a lower concentration of Δ(8)-tetrahydrocannabinolic acid.

25. The process of claim 1 , wherein relative to the Cannabis in step (a), the second extract includes a higher concentration of Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol.

26. The process of claim 1 , wherein first extract comprises less than 10 wt. % in the aggregate of Δ(8)-tetrahydrocannabinol and Δ(9)-tetrahydrocannabinol.

Assignments (2)
SECURITY INTEREST Recorded Oct 18, 2024
From: AVENIR WELLNESS SOLUTIONS, INC.
To: SINDERBRAND LAW GROUP, PC
Reel/Frame 068937/0949 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 17, 2023
From: AVENIR WELLNESS SOLUTIONS, INC. F/K/A CURE PHARMACEUTICAL HOLDING CORPORATION
To: AVENIR WELLNESS SOLUTIONS, INC.
Reel/Frame 063663/0831 →
Continuity (7)
Continuation 16809700 · Mar 5, 2020
Continuation 16359579 · Mar 20, 2019
Continuation 14934940 · Nov 6, 2015
Continuation 14723980 · May 28, 2015
Continuation In Part 14694303 · Apr 23, 2015
Continuation 14255296 · Apr 17, 2014
Related Publication 20230085079A1 · Mar 16, 2023