CA2751741C - 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
CA2751741C
CA2751741C CA2751741A CA2751741A CA2751741C CA 2751741 C CA2751741 C CA 2751741C CA 2751741 A CA2751741 A CA 2751741A CA 2751741 A CA2751741 A CA 2751741A CA 2751741 C CA2751741 C CA 2751741C
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Canada
Prior art keywords
aryl
alkyl
reaction mixture
group
general formula
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CA2751741A
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English (en)
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CA2751741A1 (fr
Inventor
Bobby N. Trawick
Mark H. Owens
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.)
Aurora Cannabis Enterprises Inc
Original Assignee
Prairie Plant Systems Inc
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Publication date
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Publication of CA2751741A1 publication Critical patent/CA2751741A1/fr
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Publication of CA2751741C publication Critical patent/CA2751741C/fr
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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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 CA2751741A1 (fr) 2009-08-14
CA2751741C true 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)

Families Citing this family (11)

* 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
US20170008869A1 (en) * 2015-07-10 2017-01-12 Noramco, Inc. Process for the production of cannabidiol and delta-9-tetrahydrocannabinol
US10239808B1 (en) 2016-12-07 2019-03-26 Canopy Holdings, LLC Cannabis extracts
CA3089994A1 (fr) 2018-01-31 2019-08-08 Canopy Holdings, LLC Poudre de chanvre
WO2020041326A1 (fr) * 2018-08-20 2020-02-27 Berkowitz Barry A Applications de cannabinoïdes connus et nouveaux
CA3119729A1 (fr) 2018-10-10 2020-04-16 Treehouse Biotech, Inc. Synthese du cannabigerol
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
JP2006508132A (ja) * 2002-11-12 2006-03-09 マリンクロッド・インコーポレイテッド カンナビノイド結晶性誘導体およびカンナビノイド精製方法
TWI369203B (en) * 2004-11-22 2012-08-01 Euro Celtique Sa Methods for purifying trans-(-)-△9-tetrahydrocannabinol and trans-(+)-△9-tetrahydrocannabinol
ZA200802767B (en) * 2005-09-29 2009-09-30 Amr Technology Inc Process for production of delta-9-tetrahydrocannabinol
GB0702895D0 (en) * 2007-02-14 2007-03-28 Resolution Chemicals Ltd Delta 9 tetrahydrocannabinol derivatives

Also Published As

Publication number Publication date
CA2751741A1 (fr) 2009-08-14
WO2009099868A1 (fr) 2009-08-13

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