# US 11,306,116 B2 · Method for separating natural substance mixtures by means of SCPC

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- Number: US 11,306,116 B2
- Document ID: US11306116B2
- Status: Granted
- Kind: B2
- Application number: 16/613,546
- Filed: 2018-05-29
- Published: 2021-07-29
- Granted: 2022-04-19
- Earliest claimed: 2017-05-29
- Assignees: Spectrum Therapeutics GMBH
- Applicants: Spectrum Therapeutics GmbH
- Inventors: Michael Englert; Andreas Ruiz
- Web page: https://patentgrep.com/patent/US11306116B2

## CPC

- C07H 17/04: Heterocyclic radicals containing only oxygen as ring hetero atoms
- B01D 15/1892: {the sorbent material moving as a whole, e.g. continuous annular chromatography, true moving beds or centrifugal chromatography}
- B01D 15/1894: {Liquid-liquid chromatography, e.g. centrifugal partition chromatography or extraction chromatography}
- B01D 15/30: Partition chromatography
- C07C 7/10: by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
- C07C 37/72: by liquid-liquid treatment
- C07D 311/64: with oxygen atoms directly attached in position 8
- C07D 311/78: Ring systems having three or more relevant rings
- A61K 2236/30: Extraction of the material
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- 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)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

The invention relates to a method for separating natural substance mixtures, in particular those consisting of plant extracts, and for isolating and purifying and obtaining same, by means of sequential centrifugal partition chromatography (sCPC).

## Claims

### Claim 1

A method for separating and/or purifying one or more cannabinoids from a Cannabis plant extract, comprising a step of performing at least one liquid-liquid partition chromatography on the Cannabis plant extract to separate and/or purify the one or more cannabinoids, wherein in performing the at least one liquid-liquid partition chromatography a continuous change of the stationary phase to the mobile phase and vice versa takes place, and wherein one or more fractions are removed to separate and/or purify the one or more cannabinoids.

### Claim 2 (depends on 1)

The method according to claim 1, wherein at least one rotor is used.

### Claim 3 (depends on 2)

The method according to claim 2, wherein a rotation of more than 2,000 rpm takes place.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the Cannabis plant extract contains less than 40 wt % fat/lipids.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the Cannabis plant extract is obtained from a first solvent selected from the group consisting of alcohols, water, hydrocarbons, and mixtures thereof, and the soluble parts are used.

### Claim 6 (depends on 1)

The method according to claim 1, wherein the Cannabis plant extract is a Cannabis sativa extract.

### Claim 7 (depends on 1)

The method according to claim 1, wherein the stationary phase and mobile phase are independently selected from the group consisting of hydrocarbons having 5-8 carbon atoms, acetonitrile, ethyl acetate, t-butyl methyl ether, alcohols, and water, so that a two-phase system can be obtained.

### Claim 8 (depends on 7)

The method according to claim 7, wherein the solvents at least contain:
a.) n-heptane and/or acetonitrile, n-heptane/acetonitrile;
b.) n-heptane/ethyl acetate/acetonitrile;
c.) n-heptane/ethyl acetate/t-butyl methyl ether/acetonitrile;
d.) n-heptane/ethyl acetate/methanol/water;
e.) n-heptane/ethanol/water.

### Claim 9 (depends on 7)

The method according to claim 7, wherein the stationary phase and mobile phase are independently selected from n-heptane, acetonitrile, ethyl acetate, t-butyl methyl ether, water, ethanol, methanol, n-heptane and/or acetonitrile, so that a two-phase system can be obtained.

### Claim 10

A method for separating and/or purifying one or more cannabinoids from a Cannabis plant extract, comprising at least one liquid-liquid partition chromatography step, wherein a continuous change of the stationary phase to the mobile phase and vice versa takes place, wherein at least one cannabinoid is removed.

### Claim 11 (depends on 10)

The method according to claim 10, wherein at least one rotor is used.

### Claim 12 (depends on 11)

The method according to claim 11, wherein a rotation of more than 2,000 rpm takes place.

### Claim 13 (depends on 10)

The method according to claim 10, wherein the Cannabis plant extract contains less than 40 wt % fat/lipids.

### Claim 14 (depends on 10)

The method according to claim 10, wherein the Cannabis plant extract is obtained from a first solvent selected from the group consisting of alcohols, water, hydrocarbons, and mixtures thereof, and the soluble parts are used.

### Claim 15 (depends on 10)

The method according to claim 10, wherein the one or more cannabinoids is cannabidiol or tetrahydrocannabinol.

### Claim 16 (depends on 7)

The method according to claim 7, wherein the Cannabis plant extract is a Cannabis sativa extract.

### Claim 17 (depends on 10)

The method according to claim 10, wherein the stationary phase and mobile phase are independently selected from the group consisting of hydrocarbons having 5-8 carbon atoms, acetonitrile, ethyl acetate, t-butyl methyl ether, alcohols, and water, so that a two-phase system can be obtained.

### Claim 18 (depends on 10)

The method according to claim 10, wherein the solvents at least contain:
a.) n-heptane and/or acetonitrile, n-heptane/acetonitrile;
b.) n-heptane/ethyl acetate/acetonitrile;
c.) n-heptane/ethyl acetate/t-butyl methyl ether/acetonitrile;
d.) n-heptane/ethyl acetate/methanol/water;
e.) n-heptane/ethanol/water.

### Claim 19 (depends on 17)

The method according to claim 17, wherein the stationary phase and mobile phase are selected from n-heptane, acetonitrile, ethyl acetate, t-butyl methyl ether, water, ethanol, methanol, n-heptane and/or acetonitrile, so that a two-phase system can be obtained.
