AU2023213750A1 - Methods of synthesizing cannabidiol, derivatives thereof, and other phytocannabinoids - Google Patents

Methods of synthesizing cannabidiol, derivatives thereof, and other phytocannabinoids Download PDF

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Publication number
AU2023213750A1
AU2023213750A1 AU2023213750A AU2023213750A AU2023213750A1 AU 2023213750 A1 AU2023213750 A1 AU 2023213750A1 AU 2023213750 A AU2023213750 A AU 2023213750A AU 2023213750 A AU2023213750 A AU 2023213750A AU 2023213750 A1 AU2023213750 A1 AU 2023213750A1
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Australia
Prior art keywords
compound
formula
suitable solvent
acid
conditions sufficient
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Pending
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AU2023213750A
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English (en)
Inventor
Jason S. Kingsbury
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Citrachem Inc
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Citrachem Inc
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Publication of AU2023213750A1 publication Critical patent/AU2023213750A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/658—Medicinal preparations containing organic active ingredients o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
AU2023213750A 2022-01-27 2023-01-27 Methods of synthesizing cannabidiol, derivatives thereof, and other phytocannabinoids Pending AU2023213750A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US202263303614P 2022-01-27 2022-01-27
US63/303,614 2022-01-27
PCT/US2023/011743 WO2023147057A2 (en) 2022-01-27 2023-01-27 Methods of synthesizing cannabidiol, derivatives thereof, and other phytocannabinoids

Publications (1)

Publication Number Publication Date
AU2023213750A1 true AU2023213750A1 (en) 2024-07-18

Family

ID=87472576

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2023213750A Pending AU2023213750A1 (en) 2022-01-27 2023-01-27 Methods of synthesizing cannabidiol, derivatives thereof, and other phytocannabinoids

Country Status (7)

Country Link
US (1) US20250282743A1 (https=)
EP (1) EP4469426A4 (https=)
JP (1) JP2025504670A (https=)
AU (1) AU2023213750A1 (https=)
CA (1) CA3246935A1 (https=)
IL (1) IL314325A (https=)
WO (1) WO2023147057A2 (https=)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8163944B2 (en) * 2007-10-08 2012-04-24 University Of Maryland College Park Allylic oxidations catalyzed by dirhodium catalysts under aqueous conditions
DE102009019322A1 (de) * 2009-04-30 2010-11-11 The Health Concept Gmbh Verfahren zur Herstellung von Synthetischen Cannabinoiden
WO2019088854A1 (en) * 2017-11-02 2019-05-09 Victoria Link Ltd Brartemicin analogues
JP2022507668A (ja) * 2018-11-14 2022-01-18 エンバイオ リミテッド カンナビノイドを調製するための方法および化合物

Also Published As

Publication number Publication date
US20250282743A1 (en) 2025-09-11
IL314325A (en) 2024-09-01
EP4469426A4 (en) 2026-04-29
CA3246935A1 (en) 2023-08-03
EP4469426A2 (en) 2024-12-04
WO2023147057A2 (en) 2023-08-03
WO2023147057A3 (en) 2023-09-07
JP2025504670A (ja) 2025-02-14

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