IP Library Granted Patent US 9,186,386
Granted Patent B2
US 9,186,386 · App. 14/723,980 · Granted Nov 17, 2015

Pharmaceutical composition and method of manufacturing

Inventor: Gary J. Speier (Eden Prairie, MN)
A61K36/185A61K36/00
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Quick Facts
Patent No.
US 9,186,386
App. No.
14/723,980
Granted
Nov 17, 2015
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 (38)

1. A process for obtaining a first concentrate of Cannabis sativa, Cannabis indica , or combination thereof, enriched with tetrahydrocannabinols (THCs) and a second concentrate of Cannabis sativa, Cannabis indica , or combination thereof, enriched with cannabidiols (CBDs), the process comprising:

(a) contacting plant material comprising Cannabis sativa, Cannabis indica , or a combination thereof, with a supercritical fluid solvent system, at a pressure of about 750-3,000 psi, and at a temperature of about 35-60° C., to provide an extract of Cannabis sativa, Cannabis indica , or combination thereof; and

(b) removing the supercritical fluid solvent system from the extract;

wherein the (a) contacting of the plant material comprising Cannabis sativa, Cannabis indica , or a combination thereof, with the supercritical fluid solvent system and the (b) removing the supercritical fluid solvent system, is carried out two or more times, such that the process is a fractional supercritical fluid extraction;

wherein a first fractional supercritical fluid extraction is carried out such that (a) contacting of the plant material comprising Cannabis sativa, Cannabis indica , or a combination thereof, with the supercritical fluid solvent system is carried out at a pressure of about 900 psi to about 1,100 psi and a temperature of about 35° C. to about 60° C. for a period of time of about 1-8 hours, to provide a first concentrate enriched with tetrahydrocannabinols (THCs);

wherein a second fractional supercritical fluid extraction is carried out such that (a) contacting of the plant material comprising Cannabis sativa, Cannabis indica , or a combination thereof, with the supercritical fluid solvent system is carried out at a pressure of about 1,900 psi to about 2,100 psi and a temperature of about 35° C. to about 60° C., for a period of time of about 1-8 hours, to provide a second concentrate enriched with cannabidiols (CBDs).

2. The process of claim 1 , wherein the first fractional supercritical fluid extraction is carried out at a temperature of about 55° C. to about 65° C.

3. The process of claim 1 , wherein the first fractional supercritical fluid extraction is carried out with carbon dioxide (CO 2 ) as the sole solvent.

4. The process of claim 1 , wherein the second fractional supercritical fluid extraction is carried out at a temperature of about 55° C. to about 65° C.

5. The process of claim 1 , wherein the second fractional supercritical fluid extraction is carried out with carbon dioxide (CO 2 ) as the sole solvent.

6. The process of claim 1 , wherein the (a) contacting of the plant material comprising Cannabis sativa, Cannabis indica , or a combination thereof, with the supercritical fluid solvent system and the (b) removing the supercritical fluid solvent system, is carried out two times.

7. The process of claim 1 , wherein the first concentrate of Cannabis sativa, Cannabis indica , or combination thereof, relative to the plant material comprising Cannabis sativa, Cannabis indica , or a combination thereof, is at least partially purified from at least one of terpenes, alkaloids, hemp oil, and cannabinoid acids.

8. The process of claim 1 , wherein the second concentrate of Cannabis sativa, Cannabis indica , or combination thereof, relative to the plant material comprising Cannabis sativa, Cannabis indica , or a combination thereof, is at least partially purified from at least one of terpenes, alkaloids, hemp oil, and cannabinoid acids.

9. The process of claim 1 , further comprising purifying the concentrate of Cannabis sativa, Cannabis indica , or combination thereof, employing at least one of chromatography, adsorption, crystallization, distillation, liquid-liquid extraction, filtration, fractional distillation, precipitation, recrystallization, and sublimation.

10. The process of claim 1 , wherein the first concentrate is enriched with tetrahydrocannabinols (THCs) comprising at least one of:

Δ(9)-tetrahydrocannabinol (Δ(9)-THC), which is 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol; and

Δ(8)-tetrahydrocannabinol (Δ(8)-THC), which is 6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol.

11. The process of claim 1 , wherein the second concentrate is enriched with cannabidiols (CBDs) comprising:

Δ(2)-cannabidiol (Δ(2)-CBD), which is 2-(6-isopropenyl-3-methyl-2-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.

12. The process of claim 1 , wherein the first concentrate is enriched with tetrahydrocannabinols (THCs), such that the first concentrate comprises at least about 90 wt. % tetrahydrocannabinols (THCs).

13. The process of claim 1 , wherein the first concentrate is enriched with tetrahydrocannabinols (THCs), such that the first concentrate comprises less than about 10 wt. %, in the aggregate, of terpenes, alkaloids, hemp oil, and cannabinoid acids.

14. The process of claim 1 , wherein the second concentrate is enriched with cannabidiols (CBDs), such that the second concentrate comprises at least about 90 wt. % tetrahydrocannabinols (THCs).

15. The process of claim 1 , wherein the second concentrate is enriched with cannabidiols (CBDs), such that the second concentrate comprises less than about 10 wt. %, in the aggregate, of terpenes, alkaloids, hemp oil, and cannabinoid acids.

16. A process for obtaining a first concentrate of Cannabis sativa, Cannabis indica , or combination thereof, enriched with tetrahydrocannabinols (THCs) and a second concentrate of Cannabis sativa, Cannabis indica , or combination thereof, enriched with cannabidiols (CBDs), the process comprising:

(a) contacting plant material comprising Cannabis sativa, Cannabis indica , or a combination thereof, with a supercritical fluid solvent system, at a pressure of about 750-3,000 psi, and at a temperature of about 35-65° C., to provide an extract of Cannabis sativa, Cannabis indica, or combination thereof; and

(b) removing the supercritical fluid solvent system from the extract;

wherein the (a) contacting of the plant material comprising Cannabis sativa, Cannabis indica, or a combination thereof, with the supercritical fluid solvent system and the (b) removing the supercritical fluid solvent system, is carried out two times, such that the process is a fractional supercritical fluid extraction;

wherein a first fractional supercritical fluid extraction is carried out such that (a) contacting of the plant material comprising Cannabis sativa, Cannabis indica , or a combination thereof, with the supercritical fluid solvent system is carried out at a pressure of about 900 psi to about 1,100 psi and a temperature of about 35-65° C. for a period of time of about 1-8 hours, to provide a first concentrate enriched with tetrahydrocannabinols (THCs);

wherein a second fractional supercritical fluid extraction is carried out such that (a) contacting of the plant material comprising Cannabis sativa, Cannabis indica , or a combination thereof, with the supercritical fluid solvent system is carried out at a pressure of about 1,900 psi to about 2,100 psi and a temperature of about 35-65° C., for a period of time of about 1-8 hours, to provide a second concentrate enriched with cannabidiols (CBDs).

17. The process of claim 16 , wherein the first concentrate is enriched with tetrahydrocannabinols (THCs) comprising at least one of:

Δ(9)-tetrahydrocannabinol (Δ(9)-THC), which is 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol;

(−)-trans-Δ(9)-tetrahydrocannabinol, which is (6aR,10aR)-Δ9-tetrahydrocannabinol;

(−)-cis-Δ9-tetrahydrocannabinol, which is (6aS,10aR)-Δ9-tetrahydrocannabinol; and

Δ(8)-tetrahydrocannabinol (Δ(8)-THC), which is 6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol.

18. The process of claim 16 , wherein the second concentrate is enriched with cannabidiols (CBDs) comprising:

Δ(2)-cannabidiol (Δ(2)-CBD), which is 2-(6-isopropenyl-3-methyl-2-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.

19. The process of claim 16 , wherein the first fractional supercritical fluid extraction is carried out at a temperature of about 55° C. to about 65° C.

20. The process of claim 16 , wherein the second fractional supercritical fluid extraction is carried out at a temperature of about 55° C. to about 65° C.

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 Jul 31, 2018
From: SPEIER, GARY J.
To: CURE PHARMACEUTICAL HOLDING CORP.
Reel/Frame 046512/0474 →
Continuity (3)
Continuation In Part 14255296 · Apr 17, 2014
Continuation In Part 14694303 · Apr 23, 2015
Related Publication 20150297654A1 · Oct 22, 2015