Cannabidiol compositions having modified cannabinoid profiles
AssigneePurisys LLC
InventorsDaniel M. HALLOW, Jun HE, Mark C. DOBISH, Denis PETROVIC, Gnel MKRTCHYAN
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Abstract
The present disclosure relates to the preparation of a highly pure cannabidiol compound by a novel synthesis route. The cannabidiol compound can be prepared by an acid-catalyzed reaction of a di-halo olivetol with menthadienol, followed by two crystallization steps. The highly pure cannabidiol compound is produced in high yield, stereospecificity, or both, and shows exceedingly low levels of Δ-9-tetrahydrocannabinol at the time of preparation and after storage.
Claims55
A composition comprising cannabidiol and delta-9-tetrahydrocannabinol, wherein said delta-9-tetrahydrocannabinol is present in an amount less than 10 ppm.
A stable composition comprising cannabidiol and delta-9-tetrahydrocannabinol, wherein said delta-9-tetrahydrocannabinol is present in an amount less than 10 ppm upon storage for 2 years or less.
A composition comprising cannabidiol and less than 10 ppm delta-9-tetrahydrocannabinol, wherein the ratio of cannabidiol to delta-9-tetrahydrocannabinol is less than 1:0.0001 as measured by UPLC.
A formulation comprising,
- cannabidiol,
- delta-9-tetrahydrocannabinol, wherein said delta-9-tetrahydrocannabinol is present in an amount less than 10 ppm, and
- a pharmaceutically acceptable excipient.
A method of preparing crystalline cannabidiol characterized by an X-ray powder diffraction pattern substantially as depicted in FIG. 11A and having less than 10 ppm delta-9-tetrahydrocannabinol, comprising crystalizing the cannabidiol from isooctane.
A method of preparing a cannabidiol composition, comprising
- contacting di-halo olivetol with menthadienol in the presence of a protic acid
- catalyst to prepare di-halo cannabidiol;
- contacting the di-halo cannabidiol with a reducing agent to prepare a first cannabidiol composition;
- contacting the first cannabidiol composition with a first solvent;
- crystallizing a second cannabidiol composition from said solvent;
- and
- recrystallizing crystalline cannabidiol composition having less than 10 ppm delta-9-tetrahydrocannabinol from a second solvent.
A method of recrystallizing cannabidiol from a mixture of cannabinoids to prepare a composition comprising cannabidiol and less than 10 ppm delta-9-tetrahydrocannabinol, said method comprising,
- contacting said mixture of cannabinoids with isooctane to form a solution;
- heating said solution to about 40° C.;
- cooling the solution to about 32° C.;
- seeding said solution at about 32° C. with (−)-Cannabidiol to prepare a suspension;
- allowing said suspension to warm to about 32° C. with stirring;
- cooling the suspension to −20° C.;
- separating a solid material from said suspension;
- washing solid material with isooctane at about −20° C.;
- and
- drying the solid material to obtain a crystalline composition comprising cannabidiol and less than 10 ppm delta-9-tetrahydrocannabinol.
A method of treating a disease in a subject comprising,
- administering to said subject a composition comprising a therapeutic amount of cannabidiol and an amount of delta-9-tetrahydrocannabinol, wherein said amount of delta-9-tetrahydrocannabinol is less than about 20 μg per day.
A composition comprising:
- cannabidiol, halogenated cannabidiol and delta-9-tetrahydrocannabinol, wherein said cannabidiol is present in an amount of at least about 99.999% w/w of the composition, said delta-9-tetrahydrocannabinol is present in an amount less than 10 ppm and said halogenated cannabidiol is present in an amount less than 10 ppm.
An enriched composition comprising:
- at least 99.999% cannabidiol, and total impurities less than 10 ppm, wherein said impurities comprise a halogenated cannabidiol.
A recrystallized composition comprising:
- cannabidiol, halogenated cannabidiol and delta-9-tetrahydrocannabinol, wherein said cannabidiol is present in an amount at least about 99.999% w/w of the composition, said delta-9-tetrahydrocannabinol is present in an amount less than 5 ppm, and said halogenated cannabidiol is present in an amount less than about 10 ppm, wherein said composition is a solid.
A crystalline cannabidiol composition comprising:
- cannabidiol and halogenated cannabidiol, wherein said composition is free of delta-9-tetrahydrocannabinol.
A suspension comprising:
- a composition comprising, at least 99.999% cannabidiol, and total impurities less than 10 ppm, wherein said impurities comprise a halogenated cannabidiol;
- and
- a solvent, wherein said composition is insoluble or slightly insoluble in said solvent at 20° C. or below.
Dependencies are inferred from the claim text.