IP Library Granted Patent US 10,568,863
Granted Patent B2
US 10,568,863 · App. 15/552,331 · Granted Feb 25, 2020

CPC distribution chromatography of cannabinoids

Inventor: Andreas Rutz (Dornhausen, DE)
Assignee: BIONORICA ETHICS GMBH
A61K31/352B01D15/1892B01D15/30C07D311/80G01N30/38G01N2030/381
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,568,863
App. No.
15/552,331
Granted
Feb 25, 2020
Kind
B2
Abstract

The invention relates to cannabinoids and their isolation and purification and to obtaining them by means of centrifugal partition chromatography.

Claims (22)

1. A method for separating and/or purifying cannabinoids from a cannabis extract, the method including at least one liquid-liquid centrifugal partition chromatography step comprising a first solvent phase and a second non-miscible liquid phase, wherein the first solvent phase is cyclohexane, heptane, or octane and is kept stationary by centrifugal force, and wherein 1% to 15% (v/v) t-butyl methyl ether is added to the first solvent phase and/or the second non-miscible liquid phase.

2. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 1 , wherein the first solvent phase is heptane.

3. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 1 , wherein the second non-miscible liquid phase comprises acetonitrile, methanol, ethylacetate, water, or a combination thereof.

4. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 3 , wherein the second non-miscible liquid phase further comprises acetone, benzotrifluoride, n-butanol, chloroform, dichloromethane, ethanol, 2-propanol, n-propanol, or tetrahydrofuran.

5. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 1 , wherein the second non-miscible liquid phase is acetonitrile.

6. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 1 , wherein the first solvent phase is heptane and the second non-miscible liquid phase is acetonitrile.

7. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 1 , wherein 9% to 13% (v/v) t-butyl methyl ether is added to the first solvent phase and/or the second non-miscible liquid phase.

8. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 1 , having a flow of 50 mL to 600 mL per minute and/or a speed of 50 rpm to 1,500 rpm.

9. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 1 , wherein the first solvent phase and the second non-miscible liquid phase are conducted in the counter current and continuous separation occurs.

10. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 1 , wherein at least one preparative column is upstream or downstream.

11. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 1 , wherein a centrifugal partition chromatograph for separating and/or purifying cannabinoids is used.

12. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 6 , wherein 9% to 13% (v/v) t-butyl methyl ether is added to the first solvent phase and the second non-miscible liquid phase.

13. A cannabis extract obtainable according to a method from claim 12 , wherein the dronabinol purity is greater than 95%.

14. A cannabis extract obtainable according to a method from claim 12 , wherein the dronabinol purity is 99.6%.

15. A method for separating and/or purifying cannabinoids from a cannabis extract, the method including at least one liquid-liquid centrifugal partition chromatography step comprising a first solvent phase and a second non-miscible liquid phase, followed by at least one preparative column chromatography step, wherein the first solvent phase is cyclohexane, heptane, or octane and is kept stationary by centrifugal force, and the second non-miscible liquid phase comprises acetonitrile, methanol, ethylacetate, or water, and wherein the at least one preparative column chromatography step comprises a mobile phase of heptane and 3% (v/v) t-butyl methyl ether.

16. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 15 , wherein the first solvent phase is heptane.

17. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 15 , wherein the second non-miscible liquid phase is acetonitrile.

18. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 15 , wherein the first solvent phase and the second non-miscible liquid phase are conducted in the counter current and continuous separation occurs.

19. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 15 , wherein the first solvent phase is heptane and the second non-miscible liquid phase is acetonitrile.

20. A cannabis extract obtainable according to a method from claim 19 , wherein the dronabinol purity is greater than 95%.

21. A cannabis extract obtainable according to a method from claim 19 , wherein the cannabidiol purity is greater than 95%.

22. A cannabis extract obtainable according to a method from claim 19 , wherein the cannabidiol purity is 99.3%.

Assignments (2)
CHANGE OF NAME Recorded Dec 4, 2020
From: BIONORICA ETHICS GMBH
To: SPECTRUM THERAPEUTICS GMBH
Reel/Frame 054600/0136 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 17, 2017
From: RUTZ, ANDREAS
To: BIONORICA ETHICS GMBH
Reel/Frame 043881/0771 →
Priority Claims (1)
EP 15156901 · Feb 27, 2015 · regional
Continuity (1)
Related Publication 20180036278A1 · Feb 8, 2018