IP Library Granted Patent US 7,449,589
Granted Patent B2
US 7,449,589 · App. 10/584,122 · Granted Nov 11, 2008

Process for purifying (-)-Δ

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Quick Facts
Patent No.
US 7,449,589
App. No.
10/584,122
Granted
Nov 11, 2008
Kind
B2
Abstract

A process for separating (−)-Δ 9 -trans-tetrahydrocannabinol from a mixture of cannabinoids is disclosed. The process comprises at least one chromatographic step wherein a mobile phase passes trough a stationary phase. The stationary phase comprises a derivatised polysaccharide and the mobile phase comprises carbon dioxide.

Claims (13)

1. A process for separating (−)-Δ 9 -trans-tetrahydrocannabinol from a mixture comprising it and other cannabinoids, wherein the process is a preparative separation process that comprises performing on the mixture at least one chromatographic step comprising passing a mobile phase comprising carbon dioxide through a stationary phase comprising a derivatised polysaccharide, and wherein the process is capable of providing at least 0.1 gram of the separated (−)-Δ 9 -trans-tetrahydrocannabinol in less than a day.

2. A process according to claim 1 , wherein the mobile phase is a mixture of carbon dioxide and one or more modifiers.

3. A process according to claim 2 , wherein the mobile phase is a mixture of carbon dioxide and ethanol.

4. A process according to claim 3 , wherein the ratio of carbon dioxide to liquid modifier is in the range 95:5 to 75:25.

5. A process according to claim 1 , wherein the derivatised polysaccharide is immobilised on a substrate selected from the group consisting of silica gel, zirconium, alumina, ceramics and other silicas.

6. A process according to claim 1 , wherein the stationary phase comprises an amylosic polysaccharide.

7. A process according to claim 6 , wherein the stationary phase is amylose tris(3,5-dimethylphenylcarbamate) supported on macroporous silica gel.

8. A process according to claim 1 , wherein the process comprises a further chromatographic step comprising passing a mobile phase through an achiral stationary phase.

9. A process according to claim 8 , wherein the achiral stationary phase is 2-ethylpyridine siloxane immobilised on a silica support.

10. A process according to claim 8 , wherein the chromatographic step using the achiral stationary phase is performed before the chromatographic step using the stationary phase comprising a derivatised polysaccharide.

11. A process according to claim 8 , wherein the chromatographic step using the stationary phase comprising a derivatised polysaccharide is performed before the chromatographic step using the achiral stationary phase.

12. A process for preparing a pharmaceutical product, comprising a first step of separating (−)-Δ 9 -trans-tetrahydrocannabinol from a mixture comprising it and other cannabinoids by a process according to claim 1 , and a further step comprising combining the separated (−)-Δ 9 -trans-tetrahydrocannabinol with one or more pharmaceutical carriers to form the pharmaceutical product.

13. The process of claim 1 , wherein the process is capable of providing at least 1 gram of the separated (−)-Δ 9 -trans-tetrahydrocannabinol in less than a day.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2022
From: JOHNSON MATTHEY PUBLIC LIMITED COMPANY
To: MACFARLAN SMITH LIMITED
Reel/Frame 061888/0166 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 20, 2007
From: GEISER, FIONA OBROCK; KEENAN, JOHN JAMES; ROSSI, RONALD; SANCHEZ, ALBERT; WHELAN, JOHN MICHAEL, II
To: JOHNSON MATTHEY PUBLIC LIMITED COMPANY
Reel/Frame 019584/0289 →