WO2019043259A1 – March 7, 2019 – RECOVERY OF ACIDIC CANNABINOIDS FROM PLANT MATERIAL

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Inventors :

POPP, Johannes Richard - Sonneberger Straße 11, 96253 Untersiemau; BONN, Günther - Bahnhof-Umgebung 3, 6170 Zirl; STUPPNER, Hermann - Steinangerl 7a, 6091 Götzens; SKALTSOUNIS, Alexios Leandros - c/o University of Athens, Faculty of Pharmacy, Panepistimiopolis of Zographou, 157 71 Zographou; PETRAKIS, Eleftherios A. - c/o University of Athens, Faculty of Pharmacy, Panepistimiopolis of Zographou, 157 71 Zographou; ANGELIS, Apostolis - c/o University of Athens, Faculty of Pharmacy, Panepistimiopolis of Zographou, 157 71 Zographou; HALABALAKI, Maria - c/o University of Athens, Faculty of Pharmacy, Panepistimiopolis of Zographou, 157 71 Zographou

Owner :

BIONORICA ETHICS GMBH

Application Number :

WOEP18073757

Document Number :

WO2019043259A1

Priority Date :

September 4, 2017

Filing Date :

September 4, 2018

Date of Grant/ Publication :

March 7, 2019

Class :

B01D15 / 18; A61K31 / 352; C07D311 / 80

Abstract

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

Claim(s)

1. A method for separating and/or purifying acidic cannabinoids from cannabis plant extract, comprising the step ( s ) of : a) preparing a biphasic liquid-liquid centrifugal partition chromatography (CPC) , characterized in that the liquid stationary upper phase is the lighter phase and is an acidified non-polar phase, comprising at least one organic non-polar solvent and at least one acidic component, the liquid mobile lower phase is the heavier phase and is a neutral or basic polar phase, comprising at least one polar solvent and at least one basic component; b) subjecting the extract to CPC and eluting fractions of the extract; and c) collecting acidic cannabinoids from one or more of the fractions .;
2. The method of claim 1, wherein the acidic upper phase has a pH from 1 to 3.;
3. The method of claim 1 or 2, wherein the lower phase has a pH from 7 to 11.;
4. The method of any one of the preceding claims, wherein the acidic upper phase comprises n-hexane/ethyl acetate and the lower phase comprises ethanol/water .;
5. The method of claim 4, wherein the volume ratio of n-hexane/ethyl acetate/ethanol/water at 7-9/1-3/4-6/4-6, specifically at 8/2/5/5 (v/v) .;
6. The method of any one of the preceding claims, step b) further comprising the step(s) : bl) injecting the extract diluted in the acidified upper phase into the CPC immediately followed by injecting neutral to basic lower phase to elute a first set of fractions of the extract in descending mode at a first flow rate of the lower phase.;
7. The method of claim 6, step b) further comprising the step ( s ) : b2) injecting the lower phase to elute a second set of fractions of the extract in descending mode at a second flow rate of the lower phase, which is 1.2 to 2.0-fold higher than the first flow rate.;
8. The method of claim 6 or 7, step b) further comprising the step ( s ) : b3) injecting the upper phase to obtain a third set of fractions of the extract in ascending mode at a third flow rate.;
9. The method of any one of the preceding claims, further comprising the step(s) : purifying the fractions obtained in step c) by biphasic liquid-liquid extraction (LLE) , wherein the polar water phase has a pH from 0.5 to 2, preferably pH 1.;
10. The method of claim 9, wherein in step d) the non-polar organic phase comprises n-hexane/ethyl acetate and the polar water phase comprises water and a strong inorganic acid.;
11. Acidic cannabioid composition, obtainable by the method of any one of claims 1 to 10, characterized in that the purity of CBDA is greater than 95%.;
12. Cannabidiolic acid (CBDA), obtainable by the method of any one of claims 1 to 10, wherein the purity is greater than 95%. 13. The use of the method of any one of claims 1 to 10 for the preparation of acidic cannabinoids from cannabis plant material at a recovery rate of pure CBDA (>95% purity) of greater than 40% or at a recovery rate of CBDA (>85% purity) of greater than 85%.

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