CA3246935A1 - METHODS OF SYNTHESIZING CANNABIDIOL, ITS DERIVATIVES AND OTHER PHYTOCANNABINOIDS - Google Patents

METHODS OF SYNTHESIZING CANNABIDIOL, ITS DERIVATIVES AND OTHER PHYTOCANNABINOIDS

Info

Publication number
CA3246935A1
CA3246935A1 CA3246935A CA3246935A CA3246935A1 CA 3246935 A1 CA3246935 A1 CA 3246935A1 CA 3246935 A CA3246935 A CA 3246935A CA 3246935 A CA3246935 A CA 3246935A CA 3246935 A1 CA3246935 A1 CA 3246935A1
Authority
CA
Canada
Prior art keywords
compound
formula
suitable solvent
acid
conditions sufficient
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CA3246935A
Other languages
English (en)
French (fr)
Inventor
Jason S. Kingsbury
Original Assignee
Citrachem Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Citrachem Inc filed Critical Citrachem Inc
Publication of CA3246935A1 publication Critical patent/CA3246935A1/en
Pending legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • 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
    • 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

Landscapes

  • 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)
CA3246935A 2022-01-27 2023-01-27 METHODS OF SYNTHESIZING CANNABIDIOL, ITS DERIVATIVES AND OTHER PHYTOCANNABINOIDS Pending CA3246935A1 (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
CA3246935A1 true CA3246935A1 (en) 2023-08-03

Family

ID=87472576

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3246935A Pending CA3246935A1 (en) 2022-01-27 2023-01-27 METHODS OF SYNTHESIZING CANNABIDIOL, ITS DERIVATIVES 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
AU2023213750A1 (en) 2024-07-18
US20250282743A1 (en) 2025-09-11
IL314325A (en) 2024-09-01
EP4469426A4 (en) 2026-04-29
EP4469426A2 (en) 2024-12-04
WO2023147057A2 (en) 2023-08-03
WO2023147057A3 (en) 2023-09-07
JP2025504670A (ja) 2025-02-14

Similar Documents

Publication Publication Date Title
JP2770081B2 (ja) シクロヘキサノール誘導体，これを含有する冷感剤および冷感性組成物，並びに該誘導体の製造方法およびその中間体
NZ567029A (en) Process for production of delta-9- tetrahydrocannabinol
CN101497593B (zh) 5-羟基香豆素和吡喃型香豆素类化合物及合成方法与应用
Pal et al. First application of fruit juice of Citrus limon for facile and green synthesis of bis-and tris (indolyl) methanes in water
MX2011011762A (es) Proceso para producir compuestos de p-mentano neo-enriquecidos.
CN101602656B (zh) 一种扁柏醇的合成方法
WO2021195751A1 (en) Catalytic cannabigerol processes and precursors
Siegel et al. Synthesis of racemic and optically active. DELTA. 9-tetrahydrocannabinol (THC) metabolites
CN111484525A (zh) 一种维生素a酯中间体c15及维生素a酯的制备方法
US20250282743A1 (en) Methods of synthesizing cannabidiol, derivatives thereof, and other phytocannabinoids
NZ204704A (en) Alpha-alkyl polyolefinic carboxylic acid derivatives and pharmaceutical compositions
CN106795093B (zh) 用于制备1-(3,5-二氯苯基)-2,2,2-三氟乙酮及其衍生物的方法
US4800233A (en) Cycloaliphatic aldehydes and process for the preparation thereof
Masuyama et al. Regioselective radical cyclization initiated by the reaction of allylic hydroperoxides with iron (II) sulfate
Maskens et al. Studies in the stereochemistry of 2-alkyl-3-hydroxy-and 2-alkyl-3-methoxy-butyric acids
CN106631703A (zh) 一种制备白藜芦醇的合成方法
JP2010065014A (ja) 抗アクネ菌化合物及びその製造方法
Taylor et al. Spiro γ-lactones via aluminum enolate-spiroepoxide openings
Bonacorso et al. Efficient entry to trifluoromethyl substituted chromanes from oxidative aromatization of tetrahydro-2H-chromen-5 (6H)-ones using iodine/alcohol with conventional and microwave methods
CN106946705A (zh) 一种合成(1r,2s)‑二氢茉莉酮酸甲酯的方法
Hirao et al. Fluoroalkylnorbornadienes and their corresponding valence isomer quadricyclanes—a light energy storage system
Langer et al. A new stereoselective synthesis of grandisol
CN102432433A (zh) 法呢醇的合成方法
CN103833665B (zh) 一种新的合成异噻唑的方法
US2369165A (en) Synthesis of vitamin a

Legal Events

Date Code Title Description
A00 Application filed

Free format text: ST27 STATUS EVENT CODE: A-0-1-A10-A00-A101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: APPLICATION RECEIVED - PCT

Effective date: 20240704

MFA Maintenance fee for application paid

Free format text: FEE DESCRIPTION TEXT: MF (APPLICATION, 2ND ANNIV.) - STANDARD

Year of fee payment: 2

A00 Application filed

Free format text: ST27 STATUS EVENT CODE: A-1-1-A10-A00-A102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: COMPLIANCE REQUIREMENTS DETERMINED MET

Effective date: 20241211

A15 Pct application entered into the national or regional phase

Free format text: ST27 STATUS EVENT CODE: A-1-1-A10-A15-X000 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: NATIONAL ENTRY REQUIREMENTS DETERMINED COMPLIANT

Effective date: 20241211

P18 Priority claim added or amended

Free format text: ST27 STATUS EVENT CODE: A-1-1-P10-P18-P105 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: PRIORITY CLAIM REQUIREMENTS DETERMINED COMPLIANT

Effective date: 20241211

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-1-1-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20241211

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-1-1-W10-W00-W101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: REQUEST TO REGISTER A DOCUMENT RECEIVED

Effective date: 20250207

Free format text: ST27 STATUS EVENT CODE: A-1-1-W10-W00-W111 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: CORRESPONDENT DETERMINED COMPLIANT

Effective date: 20250207

MFA Maintenance fee for application paid

Free format text: FEE DESCRIPTION TEXT: MF (APPLICATION, 3RD ANNIV.) - STANDARD

Year of fee payment: 3

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-1-1-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20251205

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-1-1-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20251205

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-1-1-W10-W00-W102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: REGISTER A DOCUMENT REQUIREMENTS DETERMINED COMPLIANT

Effective date: 20260416