IP Library Granted Patent US 9,765,000
Granted Patent B2
US 9,765,000 · App. 15/004,848 · Granted Sep 19, 2017

Methods of purifying cannabinoids, compositions and kits thereof

Inventor: Xavier Nadal Roura (Córdoba, ES)
Assignee: Phytoplant Research S.L.
C07C37/685A61K36/185B01D15/26C07C37/84C07C39/19C07C39/23C07C51/43C07C65/19A61K2236/00
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Quick Facts
Patent No.
US 9,765,000
App. No.
15/004,848
Granted
Sep 19, 2017
Kind
B2
Abstract

The present specification discloses methods of purifying one or more cannabinoids from a plant material, purified cannabinoids and pharmaceutical compositions comprising one or more cannabinoids produced by the disclosed method, methods and uses for treating a disease or condition employing such purified cannabinoids and pharmaceutical compositions.

Claims (38)

1. A method of purifying one or more cannabinoids from a plant material, the method consisting essentially of the following steps:

a) incubating the plant material with a non-polar solvent selected from the group consisting of petroleum ether, pentane and hexane to form a first solvent mixture which extracts the one or more cannabinoids from a plant material;

b) reducing the volume of the first solvent mixture to about 50% or less of the original volume of the first solvent mixture in step (a) thereby concentrating the one or more cannabinoids;

c) incubating the reduced first solvent mixture at a temperature range of between about −70° C. to about 40° C. to crystalize the one or more cannabinoids;

d) incubating the one or more crystalized cannabinoids with the non-polar solvent, wherein the non-polar solvent is the same non-polar solvent as in step (a) to form a second solvent mixture, thereby dissolving at least 50% of the one or more crystalized cannabinoids; and

e) incubating the second solvent mixture at a temperature range of between about −70° C. to about 40° C. to crystalize the one or more cannabinoids, thereby resulting in the purification of one or more cannabinoids.

2. The method according to claim 1 , wherein recovery of one or more crystalized cannabinoids of step (c) is performed prior to step (d).

3. The method according to claim 2 , wherein the recovery is performed using filtration that results in collection of a crystalline product and a mother liquor.

4. The method according to claim 3 , further comprising incubating the mother liquor at a temperature range of between about −70° C. to about 40° C. to crystalize the one or more cannabinoids.

5. The method according to claim 4 , further comprising

f) recovering the one or more crystalized cannabinoids using filtration that results in collection of a crystalline product and a mother liquor; and

g) incubating the mother liquor at a temperature range of between about −70° C. to about 40° C. to crystalize the one or more cannabinoids.

6. The method according to claim 5 , wherein steps (f) and (g) are repeated at least once.

7. The method according to claim 1 , wherein steps (d) and (e) or steps (b) and (c) are repeated at least once.

8. The method according to claim 1 , wherein the first solvent mixture of step (a) is purified prior to step(b) or (c).

9. The method according to claim 1 , wherein prior to step (a), the one or more cannabinoids present in the plant material are decarboxylated by heating the plant material.

10. The method according to claim 1 , further comprising performing liquid:liquid chromatography after one or more of steps (b) or (d).

11. A method of purifying a cannabinoid from a plant material, the method consisting essentially of the following steps:

a) incubating the plant material with a solvent selected from the group consisting of pentane, hexane, heptane, cyclohexane, petroleum ethers, dicloromethane, tricloromethane, tethrahydrofurane, diethyl ether, ethanol, methanol, isopropanol, acetone, acetonitrile, ethyl acetate, butane, propane, refrigerant gas 1,1,1,2-Tetrafluoroethane (R134a), liquid CO2, subcritical CO2 or supercritical CO2 or mixes of these solvents to form a first solvent mixture which extracts the one or more cannabinoids from a plant material;

b) filtering, decanting or centrifuging the first solvent mixture;

c) reducing the volume of the first solvent mixture to dryness thereby concentrating the one or more cannabinoids in a first extract;

d) incubating the first extract with a non-polar solvent selected from the group consisting of petroleum ether, pentane and hexane to form a second solvent mixture which extracts the one or more cannabinoids from the first extract;

e) filtering, decanting or centrifuging the second solvent mixture;

f) incubating the second solvent mixture at a temperature range of between about −70° C. to about 40° C. to crystalize the one or more cannabinoids;

g) collecting the one or more crystalized cannabinoids in step (d) using filtration that results in a collection of a crystalline product and a mother liquor;

h) incubating the one or more crystalized cannabinoids with the non-polar solvent wherein the non-polar solvent is the same non-polar solvent as in step (d) to form a third solvent mixture, wherein the third solvent mixture dissolves at least 50% of the one or more crystalized cannabinoids;

i) incubating the third solvent mixture at a temperature range of between about −70° C. to about 40° C. to crystallize the one or more cannabinoids; and

j) collecting the one or more crystalized cannabinoids of step (i) using filtration that results in a collection of a crystalline product and a mother liquor, thereby resulting in the purification of one or more cannabinoids.

12. The method according to claim 11 , wherein the mother liquor of step (g) and/or step (j) is incubated at a temperature range of between about −70° C. to about 40° C. to crystalize the one or more cannabinoids.

13. The method according to claim 12 , further comprising

k) collecting the one or more crystalized cannabinoids using filtration that results in collection of crystals and a mother liquor; and

l) incubating the mother liquor at a temperature range of between about −70° C. to about −40° C. to crystalize the one or more cannabinoids.

14. The method according to claim 13 , wherein steps (k) and (l) are repeated at least once.

15. The method according to claim 11 , wherein steps (h) and (i) are repeated at least once.

16. The method according to claim 11 , wherein steps (h) (i) and (j) are repeated at least once.

17. The method according to claim 11 , wherein the first solvent mixture of step (a) is purified prior to step (b).

18. The method according to claim 11 , wherein prior to step (a), the one or more cannabinoids present in the plant material are decarboxylated by heating.

19. The method according to claim 11 , further comprising performing liquid:liquid chromatography after one or more of steps (c) (g) or (j).

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 6, 2017
From: NADAL ROURA, XAVIER
To: PHYTOPLANT RESEARCH S.L.
Reel/Frame 043510/0902 →
Continuity (2)
Provisional Application 62106644 · Jan 22, 2015
Related Publication 20160214920A1 · Jul 28, 2016