CN102766128A - δ-9-四氢大麻酚的生成方法 - Google Patents

δ-9-四氢大麻酚的生成方法 Download PDF

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Publication number
CN102766128A
CN102766128A CN2012102143814A CN201210214381A CN102766128A CN 102766128 A CN102766128 A CN 102766128A CN 2012102143814 A CN2012102143814 A CN 2012102143814A CN 201210214381 A CN201210214381 A CN 201210214381A CN 102766128 A CN102766128 A CN 102766128A
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CN
China
Prior art keywords
sulphonate
compound
alkyl
replacement
aryl
Prior art date
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Pending
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CN2012102143814A
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English (en)
Chinese (zh)
Inventor
D.C.伯迪克
S.J.科利尔
F.乔斯
B.比奥拉托
B.J.保罗
H.梅克勒
M.A.海勒
A.J.哈伯肖
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Curia Global Inc
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Albany Molecular Research Inc
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Publication of CN102766128A publication Critical patent/CN102766128A/zh
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    • 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
    • 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
    • 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
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyrane Compounds (AREA)
CN2012102143814A 2005-09-29 2006-09-28 δ-9-四氢大麻酚的生成方法 Pending CN102766128A (zh)

Applications Claiming Priority (2)

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US72203105P 2005-09-29 2005-09-29
US60/722,031 2005-09-29

Related Parent Applications (1)

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CNA2006800443431A Division CN101316832A (zh) 2005-09-29 2006-09-28 δ-9-四氢大麻酚的生成方法

Publications (1)

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CN102766128A true CN102766128A (zh) 2012-11-07

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CNA2006800443431A Pending CN101316832A (zh) 2005-09-29 2006-09-28 δ-9-四氢大麻酚的生成方法

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EP (3) EP2578561A1 (US07674922-20100309-C00001.png)
JP (1) JP2009510078A (US07674922-20100309-C00001.png)
KR (1) KR20080063800A (US07674922-20100309-C00001.png)
CN (2) CN102766128A (US07674922-20100309-C00001.png)
AU (1) AU2006297300B2 (US07674922-20100309-C00001.png)
CA (1) CA2623723A1 (US07674922-20100309-C00001.png)
IL (1) IL190388A0 (US07674922-20100309-C00001.png)
NZ (3) NZ601567A (US07674922-20100309-C00001.png)
WO (1) WO2007041167A2 (US07674922-20100309-C00001.png)
ZA (1) ZA200802767B (US07674922-20100309-C00001.png)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111183135A (zh) * 2017-08-16 2020-05-19 悉尼大学 包括脱羧步骤的植物大麻素的合成
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
CN115583933A (zh) * 2022-10-31 2023-01-10 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

Families Citing this family (68)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8039509B2 (en) 2006-11-10 2011-10-18 Johnson Matthey Public Limited Company Composition comprising (−)-Δ9-trans-tetrahydrocannabinol
US8980940B2 (en) 2006-11-10 2015-03-17 Johnson Matthey Public Limited Company Stable cannabinoid compositions and methods for making and storing them
GB0702895D0 (en) * 2007-02-14 2007-03-28 Resolution Chemicals Ltd Delta 9 tetrahydrocannabinol derivatives
GB0703284D0 (en) 2007-02-20 2007-03-28 Resolution Chemicals Ltd Delta 9 - tetrahydrocannabinol processing
LT2963031T (lt) * 2007-11-30 2019-04-10 Zynerba Pharmaceuticals, Inc. Tetrahidrokanabinolio provaistai, provaistus apimančios tetrahidrokanabinolio kompozicijos ir jų panaudojimo būdai
WO2009099868A1 (en) * 2008-02-06 2009-08-13 Mallinckrodt Inc. Process for the preparation of (-) -delta 9-tetrahydrocannabinol
GB0807915D0 (en) * 2008-05-01 2008-06-04 Resolution Chemicals Ltd Production of delta 9 tetrahydrocannabinol
US8445034B1 (en) 2010-11-02 2013-05-21 Albert L Coles, Jr. Systems and methods for producing organic cannabis tincture
ES2547354T3 (es) * 2013-09-03 2015-10-05 Symrise Ag Mezclas de compuestos cannabinoides, su preparación y uso
US9220294B2 (en) 2014-02-11 2015-12-29 Timothy McCullough Methods and devices using cannabis vapors
US9380813B2 (en) 2014-02-11 2016-07-05 Timothy McCullough Drug delivery system and method
US10821240B2 (en) 2014-02-11 2020-11-03 Vapor Cartridge Technology Llc Methods and drug delivery devices using cannabis
US10045540B2 (en) 2014-04-01 2018-08-14 Fayetteville State University Pest control composition
IL302782A (en) * 2014-05-29 2023-07-01 Radius Pharmaceuticals Inc Stable cannabinoid formulations
GB2530001B (en) 2014-06-17 2019-01-16 Gw Pharma Ltd Use of cannabidiol in the reduction of convulsive seizure frequency in treatment-resistant epilepsy
GB2531281A (en) 2014-10-14 2016-04-20 Gw Pharma Ltd Use of cannabidiol in the treatment of intractable epilepsy
EP3253727A4 (en) * 2015-02-05 2018-08-08 Colorado Can LLC Purified cbd and cbda, and methods, compositions and products employing cbd or cbda
EP3061450A1 (de) 2015-02-26 2016-08-31 Symrise AG Mischungen cannabinoider Verbindungen, deren Herstellung und Verwendung
US10059683B2 (en) * 2015-07-10 2018-08-28 Noramco, Inc. Process for the production of cannabidiol and delta-9-tetrahydrocannabinol
ES2907623T3 (es) * 2016-05-13 2022-04-25 Symrise Ag Método para purificar compuestos cannabinoides mediante cromatografía de lecho móvil simulado
US10399920B2 (en) 2016-06-01 2019-09-03 S&B Pharma, Inc. Crystalline form of cannabidiol
CN106632214B (zh) * 2016-12-28 2019-01-25 西北大学 一种大麻酚类化合物的合成方法
US10702495B2 (en) 2017-02-20 2020-07-07 Nexien Biopharma, Inc. Method and compositions for treating dystrophies and myotonia
JP2020524679A (ja) * 2017-06-20 2020-08-20 イッサム リサーチ デベロップメント カンパニー オブ ザ ヘブリュー ユニバーシティー オブ エルサレム エルティーディー． カンナビジオール酸エステル組成物およびその使用
US10640482B2 (en) 2017-07-21 2020-05-05 University Of South Florida Synthesis of cannabinoids
US10272360B2 (en) 2017-08-05 2019-04-30 Priya Naturals, Inc. Phytochemical extraction system and methods to extract phytochemicals from plants including plants of the family Cannabaceae sensu stricto
WO2019030158A1 (en) 2017-08-07 2019-02-14 Enantia, S.L. CO-CRYSTAL OF 2 - [(1R, 6R) -6-ISOPROPENYL-3-METHYLCYCLOHEX-2-EN-1-YL] -5-PENTYLBENZENE-1,3-DIOL
SG11202001725SA (en) * 2017-09-01 2020-03-30 Pureform Global Inc Synthetic cannabidiol compositions and methods of making the same
US11851415B2 (en) 2018-03-07 2023-12-26 Cleen Technology Inc. Continuous isolation of cannabidiol and cannabinoids and conversion of cannabidiol to delta 8-tetrahydrocannabinol and delta 9-tetrahydrocannabinol
US11192870B2 (en) 2018-03-07 2021-12-07 Socati Technologies—Oregon, Llc Continuous isolation of cannabidiol and conversion of cannabidiol to delta 8-tetrahydrocannabinol and delta 9-tetrahydrocannabinol
EP3539637A1 (en) * 2018-03-13 2019-09-18 CLS Labs, Inc. Cannabidiol extraction and conversion process
WO2020028198A1 (en) 2018-08-03 2020-02-06 Biomass Oil Separation Solutions, Llc Processes and apparatus for extraction of substances and enriched extracts from plant material
WO2020031179A1 (en) 2018-08-06 2020-02-13 Beetlebung Pharma Ltd. Methods for synthesis of cannabinoid compounds
US10822320B2 (en) * 2018-08-10 2020-11-03 Natural Extraction Systems, LLC Methods to purify cannabinoids
AU2019335372A1 (en) * 2018-09-05 2021-05-06 Purisys Llc Cannabidiol compositions having modified cannabinoid profiles
CN113905730A (zh) 2018-10-31 2022-01-07 南迪亚公司 大麻素共晶体的固体组合物
CN109734554B (zh) * 2019-02-25 2021-11-23 江苏暨明医药科技有限公司 一种反式-薄荷基-2,8-二烯-1-醇的合成工艺
EP3947357A4 (en) * 2019-04-05 2022-10-05 Rapid Dose Therapeutics Corp. DEVICE AND METHOD FOR CONVERTING CBD AND/OR CBD DERIVATIVES INTO AT LEAST ONE OTHER TYPE OF CANNABINOID AND/OR CANNABINOID DERIVATIVES SUCH AS THC
EP3958884A4 (en) 2019-04-23 2022-12-21 Soma Oil LLC SYSTEMS AND METHODS FOR CANNABIS PROCESSING
US10569189B1 (en) * 2019-05-17 2020-02-25 NextLeaf Solutions Ltd. Method for acetylation of cannabinoids
CN111943813B (zh) * 2019-05-17 2023-04-14 上海特化医药科技有限公司 大麻二酚类化合物的制备方法
SG11202112677WA (en) * 2019-05-23 2021-12-30 Kare Chemical Tech Inc Catalytic cannabinoid processes and precursors
CA3142976A1 (en) * 2019-06-11 2020-12-17 Canopy Growth Corporation Improved methods for converting cannabidiol into delta9-tetrahydrocannabinol under protic reaction conditions
EP3750528A1 (en) 2019-06-11 2020-12-16 Nexien Biopharma, Inc. Compositions for treating dystrophies and myotonia
US20220235023A1 (en) * 2019-06-11 2022-07-28 Canopy Growth Corporation Improved methods for converting cannabidiol into delta8-tetrahydrocannabinol
CA3142982A1 (en) * 2019-06-11 2020-12-17 Canopy Growth Corporation Improved methods for converting cannabidiol into delta9-tetrahydrocannabinol under neat or aprotic reaction conditions
CA3148236A1 (en) 2019-07-22 2021-01-28 Canopy Growth Corporation Continuous crystallization of cannabinoids in a stirred-tank reactor
US10799546B1 (en) 2019-07-26 2020-10-13 Biomass Oil Separation Solutions, Llc Modular, integrated process and apparatus for extracting, refining and remediating active substances from plant material
US10954209B1 (en) * 2019-09-15 2021-03-23 NextLeaf Solutions Ltd. Acetylation of cannabinoids using sulfuric acid catalyst
CA3154135A1 (en) 2019-09-16 2021-03-25 Vapor Cartridge Technology Llc Drug delivery system with stackable substrates
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
WO2021113083A1 (en) 2019-12-06 2021-06-10 JLABS Beauty LLC Topical compositions containing rose oil and cannabidiol and methods of making and using the same
US20230002425A1 (en) * 2020-01-08 2023-01-05 Chengdu Baiyu Pharmaceutical Co., Ltd. Cannabidiol derivatives, preparation method thereof and use thereof
WO2021139740A1 (zh) * 2020-01-08 2021-07-15 成都百裕制药股份有限公司 四氢大麻酚衍生物及其制备方法和在医药上的应用
US11767306B2 (en) * 2020-01-17 2023-09-26 Cannacraft, Inc Methods for converting CBD to tetrahydrocannabinols
US10981849B1 (en) * 2020-02-20 2021-04-20 Sci Pharmtech Inc. Method for preparing cannabinoids
EP3868736B1 (en) 2020-02-21 2022-11-30 SCI Pharmtech Inc Solvent-free method for preparing cannabinoids
GB202002754D0 (en) 2020-02-27 2020-04-15 Gw Res Ltd Methods of treating tuberous sclerosis complex with cannabidiol and everolimus
WO2021181420A1 (en) 2020-03-12 2021-09-16 Council Of Scientific And Industrial Research An Indian Registered Body Incorporated Under The Regn. Of Soc. Act (Act Xxi Of 1860) Process for the synthesis of cannabidiol and intermediates thereof
US11786838B2 (en) 2020-03-23 2023-10-17 Cannacraft, Inc. Methods for removing pesticides from Cannabis products
IL296861A (en) 2020-03-31 2022-11-01 Phytotherapeutix Ltd Terpenophenolic compounds and their use
AU2021276680A1 (en) 2020-05-22 2023-01-19 Ilera Derm LLC Compositions for treating acne and dermatological conditions
CN113896616A (zh) * 2020-07-06 2022-01-07 复旦大学 一种大麻二酚的制备方法
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
CN114644547A (zh) * 2020-12-21 2022-06-21 云南汉盟制药有限公司 一种大麻二酚和/或次大麻二酚的制备方法
CN115504864A (zh) * 2021-06-07 2022-12-23 南通新世元生物科技有限公司 从工业大麻中获取高纯度大麻二酚的方法
CN113979836B (zh) * 2021-10-13 2023-05-30 上海应用技术大学 一种4-异丙烯基-1-甲基-2-环己烯-1-醇的制备方法
WO2024028516A1 (en) 2022-08-05 2024-02-08 Salud & Semillas, S.L. CANNABINOID SYNTHESIS STARTING OUT FROM OLIVETOL AND TERPENE IN DICHLOROMETHANE WITH FeCl3 * 6H2O AS CATALYST

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5292899A (en) * 1991-11-27 1994-03-08 Synthetic Technology Corporation Synthesis of 11-nor-Δ-9-tetrahydrocannabinol-9-carboxylic acid glucuronide
CN1290275A (zh) * 1998-10-05 2001-04-04 B.F.谷德里奇公司 环烯烃聚合催化剂及聚合方法
WO2003061563A2 (en) * 2001-12-04 2003-07-31 University Of Mississippi Method of preparing delta-9 tetrahydrocannabinol
US20030187014A1 (en) * 2000-03-27 2003-10-02 Osamu Uchikawa Condensed pyrazole derivatives, process for producing the same and use thereof
WO2004043946A1 (en) * 2002-11-12 2004-05-27 Mallinckrodt Inc. Cannabinoid crystalline derivatives and process of cannabinoid purification

Family Cites Families (81)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2509387A (en) 1950-05-30 Dibenzopyran marihuana-like
GB558418A (en) 1940-08-16 1944-01-05 Roger Adams Process for securing pharmacologically useful products from cannabidiol
US2304669A (en) 1940-08-16 1942-12-08 Adams Roger Isolation of cannabidiol
US2419935A (en) 1941-07-09 1947-05-06 Adams Roger Marihuana active compounds
US2419934A (en) 1941-07-09 1947-05-06 Adams Roger Optically active tetrahydrodibenzopyrans having marihuana activity and process for making same
US2419936A (en) 1942-04-29 1947-05-06 Adams Roger Preparation of compounds with marihuana activity
US3636058A (en) 1966-03-25 1972-01-18 Hoffmann La Roche 7 10 - dihydro - 3 - alkyl - 6h - dibenzo(b d) pyran-6 9(8h)-diones and 5-hydroxy-7-alkyl-4-chromanones
US3507885A (en) 1966-03-25 1970-04-21 Hoffmann La Roche 3-alkyl-6h-dibenzo(b,d)pyrans
CH473075A (de) 1966-11-04 1969-05-31 Theodor Dr Petrzilka Verfahren zur Herstellung von in 2-Stellung substituierten Resorcinderivaten
US3920705A (en) 1967-05-19 1975-11-18 Theodore Petrzilka 6a,10a-trans-6a,10,10a-tetrahydrodibenzo(b,d)-pyrans
US3833616A (en) 1968-09-16 1974-09-03 T Petrzilka 6a,10a-trans-6a,7,8,10a-tetrahydrodibenzo(b,d)-pyrans
US3919322A (en) 1969-01-22 1975-11-11 Hoffmann La Roche 3-Substituted -5-alkyl-2-cyclohexen-1-ones
US3734930A (en) 1971-09-22 1973-05-22 R Razdan Direct synthesis of ({31 )-trans-{66 {11 tetrahydrocannabinol from olivetol and ({30 )-trans-{66 {11 -carene oxide
US4278603A (en) 1973-11-05 1981-07-14 Eli Lilly And Company Novel polymorphic crystalline form of dibenzopyranone
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
US4116979A (en) 1975-06-23 1978-09-26 Sheehan Institute For Research, Inc. Process for the preparation of (-)-6a,10a-trans-6a,7,8,10a-tetrahydrodibenzo[b,d]-pyrans
IL48824A (en) 1976-01-12 1980-05-30 Yissum Res Dev Co Pharmaceutical compositions containing (3s,js) tetrahydrocanabinol derivatives and some novel compounds of this type
PT66744B (en) 1976-07-06 1978-11-27 Lilly Co Eli Process for preparing cis-hexahydrodibenzopyranones
CA1096390A (en) 1976-07-06 1981-02-24 Edward R. Lavagnino PROCESS FOR PREPARING DL-CIS-1-HYDROXY-3-SUBSTITUTED- 6,6-DIMETHYL-6,6.alpha.,7,8,10,10.alpha.-HEXAHYDRO-9H- DIBENZO(B,D,)PYRAN-9-ONES
US4054582A (en) 1976-07-06 1977-10-18 Eli Lilly And Company Process for converting cis-hexahydrodibenzo[b,d]pyran-9-ones to trans-hexahydrodibenzo[b,d]-pyran-9-ones
US4075230A (en) 1976-11-10 1978-02-21 Eli Lilly And Company Preparation of optically active trans-hexahydrodibenzopyranones
US4102902A (en) 1976-11-10 1978-07-25 Eli Lilly And Company Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor
US4171315A (en) 1978-03-31 1979-10-16 Eli Lilly And Company Preparation of cis-hexahydrodibenzopyranones
US4202902A (en) * 1979-03-05 1980-05-13 Shell Oil Company Lipogenesis control by cyclopropane-carboxylic acids, esters and amides
CH646933A5 (fr) 1981-05-04 1984-12-28 Firmenich & Cie Procede pour la preparation de (+)-p-mentha-2,8-diene-1-ol.
US4381399A (en) 1981-12-21 1983-04-26 Aerojet-General Corporation Purification of tetrahydrodibenzo[b,d]pyrans from crude synthetic mixtures
IL80411A (en) 1986-10-24 1991-08-16 Raphael Mechoulam Preparation of dibenzopyranol derivatives and pharmaceutical compositions containing them
US4933363A (en) 1988-08-16 1990-06-12 Elsohly Mahmoud A Method for effecting systemic delivery of delta-9-tetrahydrocannabinol
US5521215A (en) 1989-11-07 1996-05-28 Ramot University Authority For Applied Research And Industrial Development Ltd. NMDA-blocking pharmaceuticals
IL92238A (en) 1989-11-07 1995-07-31 Yissum Res Dev Co ADMN blocking product containing tetrahydrocannabinol history, several new tetrahydrocannabinol histories and process for their preparation
DE4100441A1 (de) * 1991-01-09 1992-07-16 Mack Chem Pharm Verfahren zur herstellung von 6,12-dihydro-6-hydroxy-cannabidiol und dessen verwendung zur herstellung von trans-delta-9-tetrahydrocannabinol
US5635530A (en) 1991-09-12 1997-06-03 Yissum Research Development Company Of The Hebrew University Of Jerusalem (3S,4S)-delta-6-tetrahydrocannabinol-7-oic acids and derivatives thereof, processors for their preparation and pharmaceutical compositions containing them
US5538993A (en) 1991-09-12 1996-07-23 Yissum Research Development Company Certain tetrahydrocannabinol-7-oic acid derivatives
IL102082A (en) 1992-06-02 1997-07-13 Yissum Res Dev Co Antiemetic composition containing a cannabinol derivative
US5338753A (en) 1992-07-14 1994-08-16 Sumner H. Burstein (3R,4R)-Δ6 -tetrahydrocannabinol-7-oic acids useful as antiinflammatory agents and analgesics
US5342971A (en) 1992-12-29 1994-08-30 The Australian National University Process for the preparation of dibenzo[b,d]pyrans
US5389375A (en) 1993-05-21 1995-02-14 University Of Mississippi Stable suppository formulations effecting bioavailability of Δ9 -thc
US5440052A (en) 1993-08-06 1995-08-08 University Of Connecticut Compositions useful as a cannabinoid receptor probe
JPH07196565A (ja) * 1993-12-28 1995-08-01 Idemitsu Petrochem Co Ltd ４−アルキル−２−フルオロシクロヘキサノールとその製造方法及びその光学分割方法
IL115245A (en) 1995-09-11 2002-12-01 Yissum Res Dev Co Tumor necrosis factor inhibiting pharmaceuticals
US6328992B1 (en) 1997-03-03 2001-12-11 Lawrence L. Brooke Cannabinoid patch and method for cannabis transdermal delivery
US6148261A (en) * 1997-06-20 2000-11-14 American Calcar, Inc. Personal communication system to send and receive voice data positioning information
US6162829A (en) 1997-10-17 2000-12-19 Atlantic Pharmaceuticals, Inc. (3R,4R)-Δ8 -tetrahydrocannabinol-11-oic acids useful as antiinflammatory agents and analgesics
DE69936640D1 (de) 1998-04-21 2007-09-06 Us Health Cannabinoiden als antioxidantien und neuroschützende mittel
US6008383A (en) 1998-10-26 1999-12-28 University Of Mississippi Method of preparing delta-9-tetrahydrocannabinol esters
EP1189603A2 (en) 1999-03-22 2002-03-27 Immugen Pharmaceuticals, Inc. Treatment of immune diseases like hiv disease and neoplastic disorders
US6566560B2 (en) 1999-03-22 2003-05-20 Immugen Pharmaceuticals, Inc. Resorcinolic compounds
US6949582B1 (en) 1999-05-27 2005-09-27 Wallace Walter H Method of relieving analgesia and reducing inflamation using a cannabinoid delivery topical liniment
FR2795731B1 (fr) 1999-07-02 2001-09-07 Warner Lambert Co PROCEDE DE PREPARATION DE [1,4] DIAZEPINO [6,7,1-hi] INDOL-4-ONES SUBSTITUEES
WO2001003690A1 (en) 1999-07-12 2001-01-18 Virginia Commonwealth University Novel vasodilator cannabinoid analogs
DE60023720T2 (de) 1999-08-20 2006-07-20 Unimed Pharmaceuticals, Inc. Zusammensetzung für inhalierung enthaltend delta-9-tetrahydrocannabinol in einem semi-wässrigen lösungsmittel
US6448288B1 (en) 2000-05-17 2002-09-10 University Of Massachusetts Cannabinoid drugs
US6974835B2 (en) 2000-05-17 2005-12-13 Indevus Pharmaceuticals, Inc. Methods for decreasing cell proliferation based on (3r,4r)-Δ8-tetrahydrocannabinol-11-oic acids
IL136839A (en) 2000-06-16 2006-12-10 Yissum Res Dev Co Pharmaceutical compositions comprising cannabidiol derivatives, and processes for the preparation of same
NZ522349A (en) 2000-06-22 2004-06-25 Pharmos Corp Non-psychotropic cannabinoids that afford neuroprotection by exhibiting anti-inflammatory and/or antioxidative and glutamate-receptor blocking mechanisms of action
US7235584B2 (en) 2000-06-22 2007-06-26 Pharmos Corporation Non-psychotropic cannabinoids
DE10051427C1 (de) 2000-10-17 2002-06-13 Adam Mueller Verfahren zur Herstellung eines Tetrahydrocannabinol- und Cannabidiol-haltigen Extraktes aus Cannabis-Pflanzenmaterial sowie Cannabis-Extrakte
US20020111377A1 (en) 2000-12-22 2002-08-15 Albany College Of Pharmacy Transdermal delivery of cannabinoids
DE10106024B4 (de) 2001-02-09 2004-10-14 Thc Pharm Gmbh Verfahren zur Herstellung von Dronabinol
US7399872B2 (en) 2001-03-07 2008-07-15 Webster G R Barrie Conversion of CBD to Δ8-THC and Δ9-THC
GB2377218A (en) 2001-05-04 2003-01-08 Gw Pharmaceuticals Ltd Process and apparatus for extraction of active substances and enriched extracts from natural products
GB0112748D0 (en) 2001-05-25 2001-07-18 Johnson Matthey Plc Uncatalysed addition reactions
GB0112752D0 (en) 2001-05-25 2001-07-18 Johnson Matthey Plc Synthesis of cannabinoids
US20030017216A1 (en) 2001-07-23 2003-01-23 Schmidt Robert Gustav Isolation of herbal and cannabinoid medicinal extracts
GB2381450B (en) 2001-10-31 2006-05-31 Gw Pharma Ltd Compositions for administration of natural or synthetic cannabinoids by vaporisation
DE60332776D1 (de) 2002-02-01 2010-07-08 Resolution Chemicals Ltd Herstellung von Delta-9-Tetrahydrocannabinol
WO2003091189A1 (en) 2002-04-25 2003-11-06 Virginia Commonwealth University Cannabinoids
US6946150B2 (en) 2002-08-14 2005-09-20 Gw Pharma Limited Pharmaceutical formulation
US20040043946A1 (en) 2002-09-03 2004-03-04 Popp Karl F. Topical formulations for treatment of skin disorders
GB2393182B (en) 2002-09-23 2007-03-14 Gw Pharma Ltd Method of preparing cannabidiol from plant material
GB0222077D0 (en) 2002-09-23 2002-10-30 Gw Pharma Ltd Methods of preparing cannabinoids from plant material
IL153277A0 (en) 2002-12-04 2003-07-06 Pharmos Corp High enantiomeric purity dexanabinol for pharmaceutical compositions
US20040248970A1 (en) 2003-04-10 2004-12-09 Webster G.R. Barrie CBD-delta8-THC composition
MXPA05010755A (es) 2003-04-10 2005-12-12 Mallinckrodt Inc Proceso regio-selectivo de delta-9-tetrahidrocanabinol.
JP2007501279A (ja) 2003-05-20 2007-01-25 ユニバーシティ・オブ・テネシー・リサーチ・ファウンデイション カンナビノイド誘導体、その製造方法、および使用
US20070287843A1 (en) 2004-04-07 2007-12-13 Cabaj John E Methods and Intermediates for the Synthesis of Delta-9 Tetrahydrocannabinol
GB2414933B (en) 2004-06-08 2009-07-15 Gw Pharma Ltd Cannabinoid compositions for the treatment of disease and/or symptoms in arthritis
CA2573859A1 (en) 2004-07-19 2006-01-26 Cilag Ltd. Method for obtaining pure tetrahydrocannabinol
US7323576B2 (en) 2004-10-01 2008-01-29 Alphora Research Inc. Synthetic route to dronabinol
TWI369203B (en) 2004-11-22 2012-08-01 Euro Celtique Sa Methods for purifying trans-(-)-△9-tetrahydrocannabinol and trans-(+)-△9-tetrahydrocannabinol
MX2007007038A (es) 2004-12-09 2008-03-07 Insys Therapeutics Inc Formulacion de dronabinol en temperatura ambiente.

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5292899A (en) * 1991-11-27 1994-03-08 Synthetic Technology Corporation Synthesis of 11-nor-Δ-9-tetrahydrocannabinol-9-carboxylic acid glucuronide
CN1290275A (zh) * 1998-10-05 2001-04-04 B.F.谷德里奇公司 环烯烃聚合催化剂及聚合方法
US20030187014A1 (en) * 2000-03-27 2003-10-02 Osamu Uchikawa Condensed pyrazole derivatives, process for producing the same and use thereof
WO2003061563A2 (en) * 2001-12-04 2003-07-31 University Of Mississippi Method of preparing delta-9 tetrahydrocannabinol
WO2004043946A1 (en) * 2002-11-12 2004-05-27 Mallinckrodt Inc. Cannabinoid crystalline derivatives and process of cannabinoid purification

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
SEUNG-HWA BAEK，等: "BORON TRIFLUORIDE ETHERATE ON ALIMINA - A MODIFIEDLE WIS ACID REAGENT.AN IMPROVED SYNTHESIS OF CANNABIDIOL", 《TETRAHEDRON LETTERS》 *
T. PETRZILKA，等: "Synthese von Haschisch-Inhaltsstoffen", 《HELVETICA CHIMICA ACTA》 *

Cited By (6)

* 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
CN111183135A (zh) * 2017-08-16 2020-05-19 悉尼大学 包括脱羧步骤的植物大麻素的合成
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
CN115583933A (zh) * 2022-10-31 2023-01-10 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
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

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