IP Library Granted Patent US 11,344,591
Granted Patent B2
US 11,344,591 · App. 16/856,492 · Granted May 31, 2022

Pharmaceutical composition and method of manufacturing

Inventor: Gary J. Speier (Eden Prairie, MN)
A61K36/185A61K9/006A61K9/7023A61K31/05A61K31/352A61K36/00B01D11/0407A61K2236/00
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Quick Facts
Patent No.
US 11,344,591
App. No.
16/856,492
Granted
May 31, 2022
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 (26)

1. A process for obtaining a first extract of Cannabis sativa, Cannabis indica , or combination thereof, enriched with terpenes and a second extract of Cannabis sativa, Cannabis indica , or combination thereof, enriched with cannabinoids, 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 800 psi-2800 psi, at a temperature of 25° C.-54° C., for a period of time of 0.5 hours-14 hours, to provide an enriched extract of Cannabis sativa, Cannabis indica , or combination thereof; and

(c) 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 800 psi-1,200 psi, at a temperature of 25° C.-35° C., for a period of time of 0.5 hours-2.5 hours, to provide a first extract enriched with terpenes;

wherein a second supercritical carbon dioxide fluid extraction is carried out such that (ii) the contacting of the Cannabis sativa, Cannabis indica , or a combination thereof, with the supercritical carbon dioxide, is carried out at a pressure of 2,000 psi-2,800 psi, at a temperature of 44° C.-54° C., for a period of time of 6 hours-14 hours, to provide an enriched extract of Cannabis sativa, Cannabis indica , or combination thereof, to provide a second extract enriched with cannabinoids; and

wherein the cannabinoids are selected from the group consisting of: cannabinol; cannabinolic acid; Δ9-tetrahydrocannabinol; Δ (9)-tetrahydrocannabinolic acid; Δ (9)-cannabidiol; Δ (9)-tetrahydrocannabidiolic acid; Δ (8)-tetrahydrocannabinol; 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.

2. The process of claim 1 , wherein the first supercritical fluid extraction is carried out at a pressure of 1,000 psi-1,200 psi.

3. The process of claim 1 , wherein the first supercritical fluid extraction is carried out at a temperature of 37° C.-39° C.

4. The process of claim 1 , wherein the first supercritical fluid extraction is carried out for a period of time of 1 hour-2 hours.

5. The process of claim 1 , wherein the first extract enriched with terpenes 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 enriched with terpenes 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 enriched with terpenes after the purification comprises at least 85 wt. % terpenes.

7. The process of claim 1 , wherein the first extract enriched with terpenes 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 enriched with terpenes after the purification comprises at least 98 wt. % terpenes.

8. The process of claim 1 , wherein relative to the cannabis in step (a), the first extract enriched with terpenes includes a lower concentration of cannabinoids.

9. The process of claim 1 , wherein the terpenes are selected from the group consisting of: β-caryophyllene epoxide; mentha-1,8(9)-dien-5-ol; pulegone; limonene; limonene oxide; α-terpinene; terpinen-4-ol; carvacrol; carvone; 1,8-cineole; p-cymene; fenchone; pulegone-1,2 epoxide; 13-myrcene; and combinations thereof.

10. The process of claim 1 , wherein the second supercritical fluid extraction is carried out at a pressure of 2,300 psi-2,500 psi.

11. The process of claim 1 , wherein the second supercritical fluid extraction is carried out at a temperature of 48° C.-50° C.

12. The process of claim 1 , wherein the second supercritical fluid extraction is carried out for a period of time of 8 hours-12 hours.

13. The process of claim 1 , wherein the second extract enriched with cannabinoids 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.

14. The process of claim 1 , wherein the second extract enriched with cannabinoids 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 cannabinoids after the purification comprises at least 85 wt. % cannabinoids.

15. The process of claim 1 , wherein the second extract enriched with cannabinoids 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 cannabinoids after the purification comprises at least 95 wt. % cannabinoids.

16. The process of claim 1 , further comprising removing the supercritical fluid solvent from the second extract enriched with cannabinoids.

17. The process of claim 1 , wherein the second extract enriched with cannabinoids comprises at least about 65 wt. % cannabinoids.

18. The process of claim 1 , wherein relative to the cannabis in step (a), the second extract enriched with cannabinoids includes a lower concentration of terpenes.

19. The process of claim 1 , wherein the cannabinoids are selected from the group consisting of: Δ9-tetrahydrocannabinol; Δ(9)-cannabidiol; Δ(8)-tetrahydrocannabinol; Δ(8)-tetrahydrocannabidiol; cannabigerol; and combinations thereof.

20. The process of claim 1 , wherein the terpenes are selected from the group consisting of: β-caryophyllene epoxide; mentha-1,8(9)-dien-5-ol; pulegone; limonene; limonene oxide; α-terpinene; terpinen-4-ol; carvacrol; carvone; 1,8-cineole; p-cymene; fenchone; pulegone-1,2 epoxide; 13-myrcene; and combinations thereof; and wherein cannabinoids are selected from the group consisting of: Δ9-tetrahydrocannabinol; Δ(9)-cannabidiol; Δ(8)-tetrahydrocannabinol; Δ(8)-tetrahydrocannabidiol; cannabigerol; and combinations thereof.

Assignments (3)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2020
From: SPEIER, GARY J
To: CURE PHARMACEUTICAL HOLDING CORP.
Reel/Frame 052939/0168 →
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 20200246405A1 · Aug 6, 2020
Cited By (1)
US 12,458,620