The present invention relates to monoterpenoid and phenylpropanoid containing derivative compounds, methods of making the compounds, compositions comprising the compounds, and methods of repelling pests using the compounds and/or compositions.

Compound of formula 4 or formula 5 ##STR00001##
wherein
L is a neutral ligand, preferably a nitrogen-containing heterocyclic carbene (NHC) such as carbene containing at least two nitrogen atoms, a cyclic aminoalkyl carbene (CAAC) or a bicyclic aminoalkyl carbene (BICAAC);
R.sup.1, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are, independently, H, unbranched or branched C.sub.1-20 alkyl, C.sub.5-9 cycloalkyl, unbranched or branched C.sub.1-20 alkoxy, optionally bearing one or more halogen atoms, respectively; or aryl, optionally substituted with one or more of unbranched or branched C.sub.1-20 alkyl, C.sub.5-9 cycloalkyl, unbranched or branched C.sub.1-20 alkoxy, aryl, aryloxy, unbranched or branched C.sub.1-20 alkylcarbonyl, arylcarbonyl, unbranched or branched C.sub.1-20 alkoxycarbonyl, aryloxycarbonyl, heteroaryl, carboxyl, cyano, nitro, amido, aminosulfonyl, N-heteroarylsulfonyl, unbranched or branched C.sub.1-20 alkylsulfonyl, arylsulfonyl, unbranched or branched C.sub.1-20 alkylsulfinyl, arylsulfinyl, unbranched or branched C.sub.1-20 alkylthio, arylthio, sulfonamide, halogen or N(R.sup.y)(R.sup.z), wherein R.sup.y and R.sup.z are independently selected from H and C.sub.1-20 alkyl:
R.sup.2 is H, unbranched or branched C.sub.1-20 alkyl.

The present invention provides improved solvents, methods, and systems for isolating purified cannabinoids from various sources. It has been found that C.sub.9 to C.sub.11 non-aromatic hydrocarbon solvents, and especially n-decane, work surprisingly well for crystallization of cannabinoids such as cannabidiol. Some variations provide a method of isolating cannabinoids from a cannabinoid-containing solution, comprising contacting the solution with a C.sub.9-C.sub.11 non-aromatic hydrocarbon solvent (e.g., n-decane) at a first temperature, to generate a mixture; cooling the mixture to precipitate cannabinoids; and isolating the precipitated cannabinoids. Other variations provide a method of isolating cannabinoids from a cannabinoid-containing solution, comprising contacting the solution with a C.sub.9-C.sub.11 non-aromatic hydrocarbon solvent (e.g., n-decane) at a first temperature below the solvent boiling point, to generate a mixture; subjecting the mixture to a second temperature that causes vaporization of the solvent, to precipitate at least some of the cannabinoids; and isolating the precipitated cannabinoids.

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).

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.

This disclosure relates to cannabinoid derivatives of Formula (I), wherein R4 or R7 is a carboxamide group, pharmaceutical compositions comprising these compounds and methods of using the cannabinoid derivatives. These compounds are potential cannabinoid receptor inhibitors, including CB1 and CB2 receptors.

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.

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.

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.

##STR00001##

This invention is for improving the manufacturing pharmaceutical grade CBD and other cannabinoids following current Good Manufacturing Practices (cGMP) of the US FDA for use in clinical trials for CNS and other indications by the NIH and other researchers. The major cannabinoids in marijuana (Cannabis) and hemp originate from Cannabigerolic Acid (CBGA) present in the biomass of the plant. Plant enzymes that are specific to different strains of biomass converts CBGA to different carboxylic acids of cannabinoids including Cannabidiolic Acid (CBDA) and Δ9-Tetrahydrocannabinolic Acid (Δ9-THCA). These are relatively stable in the growing and fresh-cut plants. These are converted by thermal decarboxylation to Cannabidiol (CBD) and Δ9-Tetrahydrocannabinol (Δ9-THC), carbon dioxide and water. Cannabinoids can be manufactured by first heating the Cannabis biomass to convert carboxylic acids prior to extraction and purification. Alternatively, and preferably because of manufacturing cost and product stability, the carboxylic acids can be first extracted and purified. They can be utilized in the carboxylic acid form or stored in a stable manner until converted to cannabinoids for use in medicine. This invention provides an efficient method for their conversion utilizing a high-pressure reactor under inert conditions.