JP7654642B2 - 触媒によるカンナビノイドプロセスおよび前駆体 - Google Patents

触媒によるカンナビノイドプロセスおよび前駆体 Download PDF

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JP7654642B2
JP7654642B2 JP2022516247A JP2022516247A JP7654642B2 JP 7654642 B2 JP7654642 B2 JP 7654642B2 JP 2022516247 A JP2022516247 A JP 2022516247A JP 2022516247 A JP2022516247 A JP 2022516247A JP 7654642 B2 JP7654642 B2 JP 7654642B2
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アブドゥール－ラシド，カマルディン
ジア，ウェンリ
アブドゥール－ラシド，カリーム
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カレ ケミカル テクノロジーズ インコーポレイテッド
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    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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)
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  • 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)
JP2022516247A 2019-05-23 2020-05-20 触媒によるカンナビノイドプロセスおよび前駆体 Active JP7654642B2 (ja)

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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
PCT/CA2020/050674 WO2020232545A1 (en) 2019-05-23 2020-05-20 Catalytic cannabinoid processes and precursors

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JP2022533484A JP2022533484A (ja) 2022-07-22
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US (1) US20220220089A1 (https=)
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KR (1) KR20220012298A (https=)
CN (1) CN114269717A (https=)
AU (1) AU2020280231A1 (https=)
CA (3) CA3179248C (https=)
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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
CA3174197A1 (en) * 2020-03-31 2021-10-07 Kamaluddin Abdur-Rashid Catalytic cannabigerol processes and precursors
US20230192588A1 (en) * 2020-06-03 2023-06-22 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Cannabidiolic acid (cbda) derivatives and uses thereof
EP4253390A4 (en) * 2020-11-25 2024-12-04 Chengdu Baiyu Pharmaceutical Co., Ltd. PROCESS FOR PURIFYING CANNABINOID COMPOUNDS
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
WO2023004414A1 (en) * 2021-07-23 2023-01-26 Colorado Chromatography, Llc A method for preparing hexahydrocannabinol
AU2022324615A1 (en) 2021-08-04 2024-02-15 Demeetra Agbio, Inc. Cannabinoid derivatives and their use
AU2022403631A1 (en) * 2021-12-09 2024-07-25 Kare Chemical Technologies Inc. Catalytic tetrahydrocannabinol synthesis and precursors
US20260097049A1 (en) * 2022-09-29 2026-04-09 Blackstone Therapeutics, Llc Cannabinoid analogs and methods of use for treatment and prevention of cancer
AU2023404746A1 (en) * 2022-12-02 2025-07-17 Benethera (Shaoxing) Biotechnology Co., Ltd. Compound and use thereof in treatment of treg-related diseases
WO2025006693A1 (en) * 2023-06-30 2025-01-02 University Of Mississippi Cannabidiol-like compounds and methods for the selective preparation of the same

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011006099A1 (en) 2009-07-10 2011-01-13 Northeastern University Angiogenic resorcinol derivatives
JP2011511075A (ja) 2008-02-08 2011-04-07 ネクター セラピューティックス オリゴマー−カンナビノイドコンジュゲート
WO2016138383A1 (en) 2015-02-27 2016-09-01 The Feinstein Institute For Medical Research Treatment method, compounds, and method of increasing trpv2 activity
JP2018522944A (ja) 2015-07-10 2018-08-16 ノラムコ， インコーポレイテッド カンナビジオール及びδ−９−テトラヒドロカンナビノールの生成のためのプロセス
CN112062697A (zh) 2019-05-22 2020-12-11 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

Family Cites Families (6)

* 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
CN102766128A (zh) * 2005-09-29 2012-11-07 阿尔巴尼分子研究公司 δ-9-四氢大麻酚的生成方法
DK3455213T3 (da) * 2016-05-13 2022-03-07 Symrise Ag Fremgangsmåde til at oprense cannabinoid-forbindelser via simulated moving bed-kromatografi
WO2020069214A2 (en) * 2018-09-26 2020-04-02 Demetrix, Inc. Optimized expression systems for producing cannabinoid synthase polypeptides, cannabinoids, and cannabinoid derivatives
CN114981235A (zh) * 2019-09-09 2022-08-30 卡瑞化学技术公司 大麻素衍生物、前体和用途
BR112022019616A2 (pt) * 2020-03-31 2022-12-06 Phytotherapeutix Ltd Compostos terpenofenólicos e seu uso

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011511075A (ja) 2008-02-08 2011-04-07 ネクター セラピューティックス オリゴマー−カンナビノイドコンジュゲート
WO2011006099A1 (en) 2009-07-10 2011-01-13 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
JP2018522944A (ja) 2015-07-10 2018-08-16 ノラムコ， インコーポレイテッド カンナビジオール及びδ−９−テトラヒドロカンナビノールの生成のためのプロセス
CN112062697A (zh) 2019-05-22 2020-12-11 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

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CROMBIE,L.W. et al.，Synthesis of bibenzyl cannabinoids. Hybrids of two biogenetic series found in Cannabis sativa，Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry(1972-1999)，1988年，No.5，p.1263-70
GONG,X. et al.，Synthesis of CBD and Its Derivatives Bearing Various C4'-Side Chains with a Late-Stage Diversification Method，Journal of Organic Chemistry，2019年12月30日，Vol.85, No.4，p.2704-2715
Yuichi KOBAYASHI et al.，Synthesis of Cannabidiols via Alkenylation of Cyclohexenyl Monoacetate，ORGANIC LETTERS，2006年，vol.8, no.13，p.2699-2702

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IL288196B1 (en) 2025-04-01
IL288196B2 (en) 2025-08-01
CN114269717A (zh) 2022-04-01
AU2020280231A1 (en) 2021-12-02
CA3179235A1 (en) 2020-11-26
CA3141590C (en) 2023-01-03
BR112021023512A2 (pt) 2022-02-01
SG11202112677WA (en) 2021-12-30
CA3141590A1 (en) 2020-11-26
CA3179248A1 (en) 2020-11-26
WO2020232545A1 (en) 2020-11-26
IL288196A (en) 2022-01-01
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CA3179248C (en) 2024-02-06
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