CA3179235A1 - Catalytic cannabinoid processes and precursors - Google Patents

Catalytic cannabinoid processes and precursors

Info

Publication number
CA3179235A1
CA3179235A1 CA3179235A CA3179235A CA3179235A1 CA 3179235 A1 CA3179235 A1 CA 3179235A1 CA 3179235 A CA3179235 A CA 3179235A CA 3179235 A CA3179235 A CA 3179235A CA 3179235 A1 CA3179235 A1 CA 3179235A1
Authority
CA
Canada
Prior art keywords
group
mmol
cyclohex
prop
alkyl
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
CA3179235A
Other languages
English (en)
French (fr)
Inventor
Kamaluddin Abdur-Rashid
Wenli Jia
Kareem ABDUR-RASHID
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kare Chemical Technologies Inc
Original Assignee
Kare Chemical Technologies 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 Kare Chemical Technologies Inc filed Critical Kare Chemical Technologies Inc
Publication of CA3179235A1 publication Critical patent/CA3179235A1/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a non-condensed ring
    • 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
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of SO3H groups or a derivative thereof
    • 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
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • 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
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C07C37/0555—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group being esterified hydroxy groups
    • 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
    • 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
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/14—Acetic acid esters of monohydroxylic compounds
    • C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
    • C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
    • 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
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical 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)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA3179235A 2019-05-23 2020-05-20 Catalytic cannabinoid processes and precursors Pending CA3179235A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201962851837P 2019-05-23 2019-05-23
US62/851,837 2019-05-23
US201962890661P 2019-08-23 2019-08-23
US62/890,661 2019-08-23
CA3141590A CA3141590C (en) 2019-05-23 2020-05-20 Catalytic cannabinoid processes and precursors

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA3141590A Division CA3141590C (en) 2019-05-23 2020-05-20 Catalytic cannabinoid processes and precursors

Publications (1)

Publication Number Publication Date
CA3179235A1 true CA3179235A1 (en) 2020-11-26

Family

ID=73459164

Family Applications (3)

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CA3179235A Pending CA3179235A1 (en) 2019-05-23 2020-05-20 Catalytic cannabinoid processes and precursors
CA3179248A Active CA3179248C (en) 2019-05-23 2020-05-20 Catalytic cannabinoid processes and precursors
CA3141590A Active CA3141590C (en) 2019-05-23 2020-05-20 Catalytic cannabinoid processes and precursors

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CA3141590A Active CA3141590C (en) 2019-05-23 2020-05-20 Catalytic cannabinoid processes and precursors

Country Status (10)

Country Link
US (1) US20220220089A1 (cg-RX-API-DMAC7.html)
EP (1) EP3959193A4 (cg-RX-API-DMAC7.html)
JP (1) JP7654642B2 (cg-RX-API-DMAC7.html)
KR (1) KR20220012298A (cg-RX-API-DMAC7.html)
CN (1) CN114269717A (cg-RX-API-DMAC7.html)
CA (3) CA3179235A1 (cg-RX-API-DMAC7.html)
IL (1) IL288196B2 (cg-RX-API-DMAC7.html)
MX (1) MX2021014329A (cg-RX-API-DMAC7.html)
SG (1) SG11202112677WA (cg-RX-API-DMAC7.html)
WO (1) WO2020232545A1 (cg-RX-API-DMAC7.html)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201916849D0 (en) * 2019-11-19 2020-01-01 Gw Res Ltd Cannabidiol-type cannabinoid compound
BR112022019616A2 (pt) 2020-03-31 2022-12-06 Phytotherapeutix Ltd Compostos terpenofenólicos e seu uso
WO2021195751A1 (en) * 2020-03-31 2021-10-07 Kare Chemical Technologies Inc. Catalytic cannabigerol processes and precursors
EP4161900A4 (en) * 2020-06-03 2025-04-23 Yissum Research Development Company of the Hebrew University of Jerusalem Ltd. Cannabidiolic acid (cbda) derivatives and uses thereof
CN116368127B (zh) * 2020-11-25 2025-10-10 成都百裕制药股份有限公司 大麻素类化合物的纯化方法
GB2602019A (en) 2020-12-15 2022-06-22 Gw Res Ltd Cannabinoid derivative as a pharmaceutically active compound and method of preparation thereof
WO2022133544A1 (en) * 2020-12-23 2022-06-30 Botanix Pharmaceuticals Limited Cbd cannabinoids and cbd cannabinoid analogues
TW202304857A (zh) * 2021-04-07 2023-02-01 加拿大商美蒂普爾製藥公司 內生性大麻素系統靶向前驅藥及其治療用途
ES3058168T3 (en) * 2021-05-12 2026-03-09 Jazz Pharmaceuticals Research Uk Ltd Resorcinol derivative as a pharmaceutically active compound and method of preparation thereof
EP4373800A4 (en) * 2021-07-23 2025-10-15 Blackstone Therapeutics Llc PROCESS FOR THE PREPARATION OF HEXAHYDROCANNABINOL
CA3227884A1 (en) 2021-08-04 2023-02-09 John Crawford Cannabinoid derivatives and their use
WO2023102655A1 (en) * 2021-12-09 2023-06-15 Kare Chemical Technologies Inc. Catalytic tetrahydrocannabinol synthesis and precursors
WO2024069589A1 (en) * 2022-09-29 2024-04-04 Blackstone Therapeutics, Llc Cannabinoid analogs and methods of use for treatment and prevention of cancer
KR20250116719A (ko) * 2022-12-02 2025-08-01 베네테라 (샤오싱) 바이오테크놀로지 코., 엘티디. 화합물 및 Treg 관련 질환의 치료에서의 이의 응용
WO2025006693A1 (en) * 2023-06-30 2025-01-02 University Of Mississippi Cannabidiol-like compounds and methods for the selective preparation of the same

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI366460B (en) * 2005-06-16 2012-06-21 Euro Celtique Sa Cannabinoid active pharmaceutical ingredient for improved dosage forms
CA2623723A1 (en) * 2005-09-29 2007-04-12 Amr Technology, Inc. Process for production of delta-9-tetrahydrocannabinol
EP2254601B1 (en) * 2008-02-08 2019-05-29 Nektar Therapeutics Oligomer-cannabinoid conjugates
US20120172339A1 (en) * 2009-07-10 2012-07-05 Northeastern University Angiogenic resorcinol derivatives
WO2016138383A1 (en) * 2015-02-27 2016-09-01 The Feinstein Institute For Medical Research Treatment method, compounds, and method of increasing trpv2 activity
US10059683B2 (en) * 2015-07-10 2018-08-28 Noramco, Inc. Process for the production of cannabidiol and delta-9-tetrahydrocannabinol
PL3455213T3 (pl) * 2016-05-13 2022-04-04 Symrise Ag Sposób oczyszczania związków kannabinoidowych przez symulowaną chromatografię z ruchomym złożem
WO2020069214A2 (en) * 2018-09-26 2020-04-02 Demetrix, Inc. Optimized expression systems for producing cannabinoid synthase polypeptides, cannabinoids, and cannabinoid derivatives
CN112062697B (zh) * 2019-05-22 2023-09-01 上海特化医药科技有限公司 间苯多酚衍生物及其制备方法
AU2020345656A1 (en) * 2019-09-09 2022-04-21 Kare Chemical Technologies Inc. Cannabinoid derivatives, precursors and uses
BR112022019616A2 (pt) * 2020-03-31 2022-12-06 Phytotherapeutix Ltd Compostos terpenofenólicos e seu uso

Also Published As

Publication number Publication date
JP7654642B2 (ja) 2025-04-01
MX2021014329A (es) 2022-01-04
CA3141590A1 (en) 2020-11-26
CA3179248C (en) 2024-02-06
IL288196B2 (en) 2025-08-01
JP2022533484A (ja) 2022-07-22
AU2020280231A1 (en) 2021-12-02
EP3959193A1 (en) 2022-03-02
BR112021023512A2 (pt) 2022-02-01
IL288196A (en) 2022-01-01
EP3959193A4 (en) 2022-07-13
CA3141590C (en) 2023-01-03
IL288196B1 (en) 2025-04-01
SG11202112677WA (en) 2021-12-30
KR20220012298A (ko) 2022-02-03
WO2020232545A1 (en) 2020-11-26
CA3179248A1 (en) 2020-11-26
US20220220089A1 (en) 2022-07-14
CN114269717A (zh) 2022-04-01

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