# US 10,864,458 B2 · Methods of purifying cannabinoids, compositions and kits thereof

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- Number: US 10,864,458 B2
- Document ID: US10864458B2
- Status: Granted
- Kind: B2
- Application number: 16/239,002
- Filed: 2019-01-03
- Published: 2019-05-09
- Granted: 2020-12-15
- Earliest claimed: 2015-01-22
- Assignees: Phytoplant Research S.L.
- Applicants: Phytoplant Research S.L.
- Inventors: Xavier Nadal Roura
- Web page: https://patentgrep.com/patent/US10864458B2

## CPC

- B01D 11/0288: {Applications, solvents}
- B01D 11/0203: {with a supercritical fluid}
- B01D 11/0492: {Applications, solvents used}
- B01D 15/1807: {using counter-currents, e.g. fluidised beds}
- B01D 15/1892: {the sorbent material moving as a whole, e.g. continuous annular chromatography, true moving beds or centrifugal chromatography}
- C07C 37/004: {by obtaining phenols from plant material or from animal material}
- C07C 37/72: by liquid-liquid treatment
- C07C 37/84: by crystallisation
- C07C 51/43: by change of the physical state, e.g. crystallisation
- C07C 51/48: by liquid-liquid treatment
- C07D 311/80: Dibenzopyrans; Hydrogenated dibenzopyrans
- B01D 11/0476: {Moving receptacles, e.g. rotating receptacles}
- C07C 2601/16: the ring being unsaturated
- G01N 30/88: Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## 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

### Claim 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, hexane and heptane 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, and
f) washing the crystallized one or more cannabinoids by dissolving in ethanol, methanol, isopropyl alcohol or acetone, filtering, evaporating to dryness and recrystallizing using the same non-polar solvent as in step a), thereby resulting in the purification of one or more cannabinoids.

### Claim 2 (depends on 1)

The method according to claim 1, wherein recovery of one or more crystalized cannabinoids of step (c) is performed prior to step (d), wherein the recovery is performed using filtration that results in collection of a crystalline product and a mother liquor.

### Claim 3 (depends on 2)

The method according to claim 2, 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.

### Claim 4 (depends on 3)

The method according to claim 3, further comprising after step e) and before step f), the steps of:
e1) recovering the one or more crystalized cannabinoids using filtration that results in a collection of a crystalline product and a mother liquor; and
e2) incubating the mother liquor at a temperature range of between about −70° C. to about 40° C. to crystalize the one or more cannabinoids.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 1)

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

### Claim 8 (depends on 1)

The method of claim 1, wherein after step c) or e) the crystallized one or more cannabinoids are washed by being dissolved in ethanol, methanol, isopropyl alcohol or acetone, filtered, evaporated to dryness and recrystallized using the same non-polar solvent as in step a).

### Claim 9

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, dichloromethane, trichloromethane, tethrahydrofuran, 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, hexane and heptane 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 (f) using filtration that results in a collection of a crystalline product and a mother liquor;
h) incubating the one or more crystalized cannabinoids of step (g) 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 crystalize the one or more cannabinoids, and then washing the crystallized one or more cannabinoids by dissolving in ethanol, methanol, isopropyl alcohol or acetone, filtering, evaporating to dryness and recrystallizing using the same non-polar solvent as in step d); 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.

### Claim 10 (depends on 9)

The method according to claim 9, 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.

### Claim 11 (depends on 9)

The method according to claim 9, wherein the first solvent mixture of step (a) is purified prior to step (b).

### Claim 12 (depends on 9)

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

### Claim 13 (depends on 9)

The method according to claim 9 further comprising performing liquid:liquid chromatography after one or more of steps (c), (g) or (j).

### Claim 14 (depends on 9)

The method of claim 9, wherein after step c) and before step d) the one or more cannabinoids in a first extract are washed by being dissolved in ethanol, methanol, isopropyl alcohol or acetone, filtered, evaporated to dryness and/or after step f) the crystallized one or more cannabinoids are washed by being dissolved in ethanol, methanol, isopropyl alcohol or acetone, filtered, evaporated to dryness and recrystallized using the same non-polar solvent as in step a).

### Claim 15 (depends on 1)

The method of claim 1, wherein the cannabinoid is CBDA or CBD.

### Claim 16 (depends on 9)

The method of claim 9, wherein the cannabinoid is CBDA or CBD.

### Claim 17 (depends on 1)

The method of claim 1, wherein the cannabinoid is CBGA or CBG.

### Claim 18 (depends on 9)

The method of claim 9, wherein the cannabinoid is CBGA or CBG.

### Claim 19 (depends on 1)

The method of claim 1, wherein in step f) the crystallized one or more cannabinoids are washed by being dissolved in ethanol.

### Claim 20 (depends on 9)

The method of claim 9, wherein in step i) the crystallized one or more cannabinoids are washed by being dissolved in ethanol.