C07C39/23

Synthesis of (+)-cannabinoids and their therapeutic effects

The present invention relates to a method of producing a compound of formula (I) or a salt of a compound of formula (I). The invention also relates to a compound of formula (I) or a salt of a compound of formula (I) for use in a therapeutic method to achieve one or more therapeutic effects as well as for use in the treatment and/or prevention of certain diseases. Furthermore, the invention provides a pharmaceutical composition comprising one or more compound(s) of formula (I) or salt(s) of compound(s) of formula (I).

Synthesis of (+)-cannabinoids and their therapeutic effects

The present invention relates to a method of producing a compound of formula (I) or a salt of a compound of formula (I). The invention also relates to a compound of formula (I) or a salt of a compound of formula (I) for use in a therapeutic method to achieve one or more therapeutic effects as well as for use in the treatment and/or prevention of certain diseases. Furthermore, the invention provides a pharmaceutical composition comprising one or more compound(s) of formula (I) or salt(s) of compound(s) of formula (I).

METHODS FOR EXTRACTION, PROCESSING, AND PURIFICATION OF A SELECTED FAMILY OF TARGET COMPOUNDS FROM CANNABIS

Disclosed are methods for separating, recovering, and purifying cannabidiolic acid (CBDA) salts from an organic solvent solution comprising a mixture of cannabinoids. The methods comprise solubilizing the mixture of cannabinoids in C5-C7 hydrocarbon solvents, adding thereto a selected amine to thereby precipitate a CBDA-amine salt therefrom, dissolving the recovered CBDA-amine salt in a selected solvent and then adding thereto a selected antisolvent to thereby recrystallize a purified CBDA-amine salt therefrom. The recrystallized CBDA-amine salt may be decarboxylated to form a mixture of cannabidiol (CBD) and amine. The CBD amine mixture may be acidified to separate the amine from CBD. Also disclosed are CBDA-amine salts produced with certain amines selected from groups of secondary amines, tertiary amines, diamines, amino alcohols, amino ethers, and highly basic amines.

METHODS FOR EXTRACTION, PROCESSING, AND PURIFICATION OF A SELECTED FAMILY OF TARGET COMPOUNDS FROM CANNABIS

Disclosed are methods for separating, recovering, and purifying cannabidiolic acid (CBDA) salts from an organic solvent solution comprising a mixture of cannabinoids. The methods comprise solubilizing the mixture of cannabinoids in C5-C7 hydrocarbon solvents, adding thereto a selected amine to thereby precipitate a CBDA-amine salt therefrom, dissolving the recovered CBDA-amine salt in a selected solvent and then adding thereto a selected antisolvent to thereby recrystallize a purified CBDA-amine salt therefrom. The recrystallized CBDA-amine salt may be decarboxylated to form a mixture of cannabidiol (CBD) and amine. The CBD amine mixture may be acidified to separate the amine from CBD. Also disclosed are CBDA-amine salts produced with certain amines selected from groups of secondary amines, tertiary amines, diamines, amino alcohols, amino ethers, and highly basic amines.

LIQUID CARBON DIOXIDE AND COSOLVENT BIOMASS EXTRACTION METHOD AND SYSTEM

Method and system for the extraction of oils from a biomass with a liquid carbon dioxide using cosolvent. The system and method can be used to extract cannabinoids from Cannabis biomass by cryogenically freezing the biomass and exposing the Cannabis biomass to sub-cooled liquid carbon dioxide and capturing a first high-terpene extract fraction, and then exposing the Cannabis biomass with a mixture of superfluid carbon dioxide and a cosolvent to capture a high cannabinoid second fraction.

LIQUID CARBON DIOXIDE AND COSOLVENT BIOMASS EXTRACTION METHOD AND SYSTEM

Method and system for the extraction of oils from a biomass with a liquid carbon dioxide using cosolvent. The system and method can be used to extract cannabinoids from Cannabis biomass by cryogenically freezing the biomass and exposing the Cannabis biomass to sub-cooled liquid carbon dioxide and capturing a first high-terpene extract fraction, and then exposing the Cannabis biomass with a mixture of superfluid carbon dioxide and a cosolvent to capture a high cannabinoid second fraction.

CANNABINOID DERIVATIVES AND PRECURSORS, AND ASYMMETRIC SYNTHESIS FOR SAME

The present disclosure relates to new cannabinoid derivatives and precursors and catalytic asymmetric processes for their preparation. The disclosure also relates to pharmaceutical compositions and pharmaceutical and analytical uses of the new cannabinoid derivatives. For instance, the disclosure relates to the preparation of new precursors, and the use of such precursor compounds for the preparation of isotope labelled cannabinoid products using chiral and achiral catalysts and catalytic processes. The deuterium, carbon-13 and carbon-14 containing compounds can be prepared and purified prior to transformation to the desired individual deuterated cannabinoid products.

PROCESS FOR THE SYNTHESIS OF CANNABIDIOL AND INTERMEDIATES THEREOF

The present invention relates to process for the preparation of cannabidiol (A) from the coupling of (D) and (E) through the intermediates (C) and (D) starting from compound (B). The invention further relates to the novel compounds (B), (C), (D) and (E) and reagents used in this process. More specifically, this invention provides the manufacturing of Cannabidiol (A) in milligram to gram or kilogram scale.

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PROCESS FOR THE SYNTHESIS OF CANNABIDIOL AND INTERMEDIATES THEREOF

The present invention relates to process for the preparation of cannabidiol (A) from the coupling of (D) and (E) through the intermediates (C) and (D) starting from compound (B). The invention further relates to the novel compounds (B), (C), (D) and (E) and reagents used in this process. More specifically, this invention provides the manufacturing of Cannabidiol (A) in milligram to gram or kilogram scale.

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Dynamic interface system and its application in supercritical fluid extraction and chromatography

The present invention provides a dynamic interface system between an extraction device and a chromatographic purification device for separating and purifying substance(s) from a mixture or matrix. One embodiment is the Supercritical Fluid Interface (“SFI”) between Supercritical Fluid Extraction (“SFE”), and Supercritical Fluid Chromatography (“SFC”). The SFI is capable of interfacing; gas, subcritical and supercritical fluid extraction methods and pair with gas, subcritical and supercritical fluid chromatography technologies that operate within the pressure and temperature parameters of the SFI. The SFI can operate up to 200 degrees celsius and 5000 psi. This interface technology allows for an inline oil extraction and chromatographic separation, the SFI can pair extraction and chromatography with the same solvent in different mobile phases, whereas the extraction can be performed using CO.sub.2 as a solvent in sub-critical phase and the SFI can receive the subcritical solution and then increase pressure and/or temperature to achieve supercritical state as required for injection into supercritical fluid chromatography technologies. The SFI coupling between SFE and SFC can to extract and refine cannabinoids from the cannabis industrious, hemp, plant and can also be applied to improve efficiency in an industry that extracts and refines oils, through chromatography, from organic materials using a gas, or sub/supercritical fluid as a solvent and mobile phase.