Bessor Pharma, LLC

Eastman Chemical Company

Anthony Gerard Barrett

Barry A Berkowitz

Daniel Elliott

Steven Leroy Cook

Phillip Wayne Turner

The use of a medicament as a single agent, binary agent, or other combination comprising of substantially pure novel cannabinoids 1 and 2, optionally admixed with one or more known and novel cannabinoids and other known naturally occurring and synthetic tetracyclic 2A and tricyclic 1A cannabinoids for the prevention, treatment or cure of inflammatory mediated diseases or inflammatory mediated pathological conditions, anorexia, arthritis, cancer, pain, glaucoma, migraine, persistent muscle spasms, seizures (epileptic seizures), severe nausea, PTSD, autism spectrum disorder, drug abuse, insomnia, or any other chronic or persistent medical symptom.

Applications of known and novel cannabinoids

The present invention relates to intermediate compounds for the synthesis of novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable &#x394;-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. Novel compounds of the formulas 3 and 6, useful as intermediates for the synthesis of the cannabinoids of advanced intermediates 4 and 5 as well as cannabinoids of the formulas 1 and 2, are disclosed.

Synthetic intermediates for novel cannabinoids and cannabinoid acids and their derivatives

A process for the preparation of substantially pure diverse known and novel cannabinoids 1 and 2, which include &#x394;-tetrahydrocannabinol (7), tetrahydrocannabivarin (9), cannabidiol (11), cannabidivarin (12) and other naturally occurring tetracyclic and tricyclic cannabinoids and other synthetic tetracyclic and tricyclic analogues, via intermediates 3, 6, 4 and 5, using a cascade sequence of allylic rearrangement, aromatization and, for the tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2, including &#x394;-tetrahydrocannabinol (7), tetrahydrocannabivarin (9), are obtained containing very low levels of isomeric cannabinoids such as the undesirable &#x394;8-tetrahydrocannabinol. The known and novel analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components oforoil.

Process for the production of cannabinoids

The present invention relates to novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable &#x394;8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components ofoil. Novel compounds of the formulas 3, 4, 5 and 6, as intermediates for the synthesis of the cannabinoids of the formulas 1 and 2 are also disclosed.

Cannabinoids and cannabinoid acids and their derivatives

The invention is directed to a process for preparing a terephthalic acid di-ester. The process includes contacting terephthalic acid with a C-Calcohol in the presence of an organo-titanium catalyst and an alcohol-amine promoter under conditions effective to form a corresponding terephthalic acid di-ester. The promoter can improve the reaction time by as much as 50%.

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Rio de Janeiro, Brazil

Anthony Gerard Barrett