CA2751741A1 - Procede pour la preparation du (-)-delta 9-tetrahydrocannabinol - Google Patents

Procede pour la preparation du (-)-delta 9-tetrahydrocannabinol Download PDF

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Publication number
CA2751741A1
CA2751741A1 CA2751741A CA2751741A CA2751741A1 CA 2751741 A1 CA2751741 A1 CA 2751741A1 CA 2751741 A CA2751741 A CA 2751741A CA 2751741 A CA2751741 A CA 2751741A CA 2751741 A1 CA2751741 A1 CA 2751741A1
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Prior art keywords
aryl
alkyl
reaction mixture
group
substituted
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CA2751741A
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English (en)
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CA2751741C (fr
Inventor
Bobby N. Trawick
Mark H. Owens
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Aurora Cannabis Enterprises Inc
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Mallinckrodt Inc
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Publication date
Application filed by Mallinckrodt Inc filed Critical Mallinckrodt Inc
Publication of CA2751741A1 publication Critical patent/CA2751741A1/fr
Application granted granted Critical
Publication of CA2751741C publication Critical patent/CA2751741C/fr
Active legal-status Critical Current
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Classifications

    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne un procédé de synthèse chimique du (-)-?9- tétrahydrocannabinol (?9-THC) et autres composés apparentés de formule (I). En particulier, le procédé comprend une séquence de réaction monotope de condensation et de sulfonylation qui produit un arylsulfonate de ?9-THC brut ou autres composés apparentés. Immédiatement lors de leur formation, la sulfonylation du ?9-THC ou autres composés apparentés confère la stabilité aux cannabinoïdes, et empêche la formation de l'isomère ?8 correspondant. Les arylsulfonates de ?9THC peuvent être facilement séparés des arylsulfonates de ?6THC par chromatographie en phases inversées. L'hydrolyse des arylsulphonates de ?9-THC ou autres composés apparentés donne un ?9-THC ou autres composés apparentés contenant des quantités relativement basses de l'isomère ?8 correspondant. (Formule I).
CA2751741A 2008-02-06 2009-01-29 Procede pour la preparation du (-)-delta 9-tetrahydrocannabinol Active CA2751741C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US2647908P 2008-02-06 2008-02-06
US61/026,479 2008-02-06
PCT/US2009/032361 WO2009099868A1 (fr) 2008-02-06 2009-01-29 Procédé pour la préparation du (-)-delta 9-tétrahydrocannabinol

Publications (2)

Publication Number Publication Date
CA2751741A1 true CA2751741A1 (fr) 2009-08-14
CA2751741C CA2751741C (fr) 2018-07-10

Family

ID=40510442

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2751741A Active CA2751741C (fr) 2008-02-06 2009-01-29 Procede pour la preparation du (-)-delta 9-tetrahydrocannabinol

Country Status (2)

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CA (1) CA2751741C (fr)
WO (1) WO2009099868A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11040932B2 (en) 2018-10-10 2021-06-22 Treehouse Biotech, Inc. Synthesis of cannabigerol
US11084770B2 (en) 2016-12-07 2021-08-10 Treehouse Biotech, Inc. Cannabis extracts
US11202771B2 (en) 2018-01-31 2021-12-21 Treehouse Biotech, Inc. Hemp powder

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3061450A1 (fr) * 2015-02-26 2016-08-31 Symrise AG Mélanges de composés cannabinoïdes, leur fabrication et leur utilisation
US10059683B2 (en) * 2015-07-10 2018-08-28 Noramco, Inc. Process for the production of cannabidiol and delta-9-tetrahydrocannabinol
KR20210090609A (ko) * 2018-08-20 2021-07-20 베서, 파마 엘엘씨 공지된 신규 칸나비노이드의 응용
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
CN109970516A (zh) * 2019-03-20 2019-07-05 栾云鹏 一种工业化制备高纯度高收率的大麻酚类物质的合成方法
US11542243B1 (en) 2019-09-26 2023-01-03 FusionFarms, LLC Method of converting delta9-THC to delta10-THC and the purification of the delta10-THC by crystallization
CN112094257B (zh) * 2020-08-19 2023-08-22 公安部禁毒情报技术中心 一种△-9四氢大麻酚的制备方法
CN115583933B (zh) * 2022-10-31 2024-02-06 暨明医药科技（苏州）有限公司 一种高纯度四氢大麻素同系物的制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4025516A (en) * 1975-06-23 1977-05-24 The John C. Sheehan Institute For Research, Inc. Process for the preparation of (-)-6a,10a-trans-6a,7,8,10a-tetrahydrodibenzo[b,d]-pyrans
AU2003287585B2 (en) * 2002-11-12 2009-05-07 Mallinckrodt Inc. Cannabinoid crystalline derivatives and process of cannabinoid purification
TWI369203B (en) * 2004-11-22 2012-08-01 Euro Celtique Sa Methods for purifying trans-(-)-△9-tetrahydrocannabinol and trans-(+)-△9-tetrahydrocannabinol
EP2578577A1 (fr) * 2005-09-29 2013-04-10 Albany Molecular Research, Inc. Esters sulfonyles de tétrahydrocannabinol et ses dérivés
GB0702895D0 (en) * 2007-02-14 2007-03-28 Resolution Chemicals Ltd Delta 9 tetrahydrocannabinol derivatives

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11084770B2 (en) 2016-12-07 2021-08-10 Treehouse Biotech, Inc. Cannabis extracts
US11202771B2 (en) 2018-01-31 2021-12-21 Treehouse Biotech, Inc. Hemp powder
US11040932B2 (en) 2018-10-10 2021-06-22 Treehouse Biotech, Inc. Synthesis of cannabigerol

Also Published As

Publication number Publication date
CA2751741C (fr) 2018-07-10
WO2009099868A1 (fr) 2009-08-13

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