Cannabinoid sulfate esters, their salts and uses thereof
AssigneeLondon Pharmaceuticals and Research Corporation
InventorMahmoud Mohamed Abdrabo Moustafa
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Abstract
Cannabinoid sulfate esters, their soluble salts and stable formulations thereof, as well as their edible, beverage and medicinal applications. The cannabinoid sulfate ester salts may be used as drugs or prodrugs for treating various conditions related to the modulation or biased modulation of cannabinoid receptors, including but not limited to, pain and inflammation, cancer, glaucoma, neurodegenerative disorders, multiple sclerosis, renal fibrosis, fibrotic disorder, addiction, motor function disorders and gastrointestinal and metabolic disorders.
Claims40
A cannabinoid compound, comprising a sulfate or hemisulfate ester of a cannabinoid having at least one hydroxyl group or pharmaceutically acceptable salts thereof;
- wherein when the cannabinoid is delta-9-tetrahydrocannabinol (THC) or delta-8-tetrahydrocannabinol (THC), the salts are not with KOH or pyridinium;
- and
- wherein when the cannabinoid is cannabidiol (CBD) and when the salts are with NaOH, the cannabinoid compound is a mono-sulfate or hemisulfate ester.
A method of producing a cannabinoid compound, comprising the steps of:
- a. dissolving a cannabinoid having at least one hydroxyl group in a suitable aprotic organic solvent to produce a cannabinoid solution;
- b. reacting the cannabinoid solution with a sulfate transfer reagent in the presence of an alkali or an organic base;
- c. heating the reaction under conventional heating, microwave heating, or sonication to produce a product;
- and
- d. purifying the product using flash chromatography, extraction, distillation, sublimation, or crystallization.
A method of producing a cannabinoid compound, comprising reacting a cannabinoid having at least one hydroxyl group in the presence of N-hydroxysuccinimide sulfate and arylsulfotransferase at a pH of between 8.5 and 9 for a reaction time of at least 12 hours.
Dependencies are inferred from the claim text.