ME02403B - POSTUPCI ZA PREČIŠĆAVANJE TRANS-(-)-Δ9-TETRAHIDROKANABINOLA l TRANS-(+) - Δ9 - TETRAHIDROKANABINOLA - Google Patents

POSTUPCI ZA PREČIŠĆAVANJE TRANS-(-)-Δ9-TETRAHIDROKANABINOLA l TRANS-(+) - Δ9 - TETRAHIDROKANABINOLA

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Publication number
ME02403B
ME02403B MEP-2016-55A MEP5516A ME02403B ME 02403 B ME02403 B ME 02403B ME P5516 A MEP5516 A ME P5516A ME 02403 B ME02403 B ME 02403B
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ME
Montenegro
Prior art keywords
tetrahydrocannabinol
trans
phase
composition
alcoholic
Prior art date
Application number
MEP-2016-55A
Other languages
English (en)
Inventor
Arie L Gutman
Gennady A Nisnevich
Igor Rukhman
Boris Tishin
Marina M Etinger
Irina M Fedotev
Boris M Pertsikov
Ram Khanolkar
Original Assignee
Euro Celtique Sa
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=35789123&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ME02403(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Euro Celtique Sa filed Critical Euro Celtique Sa
Publication of ME02403B publication Critical patent/ME02403B/me

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/658—Medicinal preparations containing organic active ingredients o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4875—Compounds of unknown constitution, e.g. material from plants or animals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/10—Laxatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • 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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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Botany (AREA)
  • Zoology (AREA)
  • Neurology (AREA)
  • Obesity (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Nutrition Science (AREA)
  • Hospice & Palliative Care (AREA)
  • Otolaryngology (AREA)
  • Diabetes (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicinal Preparation (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)

Claims (11)

1.Postupak za uklanjanje nečistoća iz kompozicije koja sadrži trans-(-) Δ9-tetrahidrokanabinol i trans-(+)-Δ9-tetrahidrokanabinol pre kristalizacije (±)-Δ9-tetrahidrokanabinola, a postupak obuhvata:(a) dovođenje u kontakt trans-(-)-Δ9-tetrahidrokanabinola i trans-(+)-Δ9 tetrahidrokanabinola sa prvim organskim rastvaračem koji se ne meša sa vodom, alkoholom koji se meša sa vodom, vodom, i hidroksidom alkalnog metala, na taj način obrazujući bifaznu kompoziciju koja sadrži (i) prvu organski fazu i (ii) alkoholnu-kaustičnu fazu koja sadrži trans-(-)- Δ9-tetrahidrokanabinol i trans-(+)-Δ9-tetrahidrokanabinol;(b) odvajanje alkoholno-kaustične faze koja sadrži trans-(-)-Δ9-tetrahidrokanabinol i trans-(+)-Δ9-tetrahidrokanabinol od prve organske faze;(c) dovođenje u kontakt alkoholno-kaustične faze sa kiselinom da bi se dobila alkoholna faza tretirana kiselinom.
2.Postupak za uklanjanje nečistoća iz kompozicije koja sadrži trans-(-)-Δ9-tetrahidrokanabinol ili trans-(+)-Δ9-tetrahidrokanabinol pre kristalizacije (±)-Δ9-tetrahidrokanabinola, a postupak obuhvata: (a) dovođenje u kontakt trans-(-)-Δ9-tetrahidrokanabinola ili trans-(+)-Δ9-tetrahidrokanabinola sa prvim organskim rastvaračem koji se ne meša sa vodom, aloholom koji se meša sa vodom, vodom, i hidroksidom alkalnog metala, tako obrazujući bifaznu kompoziciju koja sadrži (i) prvu ogransku fazu, i (ii) alkoholno-kaustičnu fazu koja sadrži trans-(-)-Δ9-tetrahidrokanabinol ili trans-(+)-Δ9-tetrahidrokanabinol; (b) odvajanje alkoholno-kaustične faze koja sadrži trans-(-)-Δ9-tetrahidrokanabinol ili trans-(+)-Δ9-tetrahidrokanabinol od prve organske faze; (c) dovođenje u kontakt alkoholno-kaustične faze sa kiselinom da bi se dobila alkoholna faza tretirana kiselinom.
3.Postupak prema zahtevu 1 ili 2, gde je kiselina limunska kiselina ili sirćetna kiselina.
4.Postupak prema bilo kom od zahteva 1 do 3, gde je kiselina dodata u količini dovoljnoj da se postigne pH od 5 do 9.
5.Postupak prema bilo kom od zahteva 1 do 4, koji obuhvata dodatni korak: (d) dovođenja u kontakt alkoholne faze tretirane sa drugim organskim rastvaračem koji se ne meša sa vodom da bi se obrazovala (i) druga organska faza koja sadrži Δ9-tetrahidrokanabinol i (ii) alkoholna faza tretirana kiselinom.
6.Postupak prema zahtevu 5, koji obuhvata dodatni korak (e) odvajanja druge organske faze od alkoholne faze koja je tretirana kiselinom.
7.Postupak dobijanja kristalnog (±)-Δ9-tetrahidrokanabinola koji obuhvata: omogućavanje kristalizacije trans-(-)-Δ9-tetrahidrokanabinola i trans-(+)-Δ9-tetrahidrokanabinola iz prve kompozicije koja sadrži trans-(-)-Δ9-tetrahidrokanabinol, trans-(+)-Δ9-tetrahidrokanabinol, i nepolarni organski rastvarač da bi se dobio kristalni (±)-Δ9-tetrahidrokanabinol, pri čemu je prva kompozicija dobijena (a) izvođenjem postupka prema bilo kom od zahteva 1 do 6, (b) odvajanjem Δ9-tetrahidrokanabinola iz dobijene faze koja sadrži Δ9-tetrahidrokanabinol; i (c) dovođenjem u kontakt Δ9-tetrahidrokanabinola iz koraka (b) sa nepolarnim organskim rastvaračem i opciono njegovim enantiomerom da bi se obrazovala prva kompozicija.
8.Postupak prema zahtevu 7, gde je nepolarni organski rastvarač ravnolančani ili razgranati (C4-C10)alifatični ugljovodonik, (C4-C10)cikloalifatični ugljovodonik, ili bilo koja njihova smeša, gde je ravnolančani ili razgranti ugljovodonik poželjno pentan, heksan, heptan, izooktan, ili bilo koja njihova smeša, a poželjnijo je n-heptan.
9.Postupak dobijanja kompozicije trans-(-)-Δ9-tetrahidrokanabinola, koji obuhvata: omogućavanje odvajanja kompozicije koja sadrži (±)-Δ9-tetrahidrokanabinol i eluacioni rastvarač na hiralnoj stacionarnoj fazi da se dobije kompozicija trans-(-)-Δ9-tetrahidrokanabinola, ili kompozicije trans-(+)-Δ9-tetrahidrokanabinola, koji obuhvata: omogućavanje odvajanja kompozicije koja sadrži (±)-Δ9-tetrahidrokanabinol i eluacioni rastvarač na hiralnoj stacionarnoj fazi da bi se dobila kompozicija trans-(+)-Δ9-tetrahidrokanabinola, gde je (±)-Δ9-tetrahidrokanabinol dobijen iz kristalnog (±)-Δ9-tetrahidrokanabinola, i gde je kristalni (±)-Δ9-tetrahidrokanabinol dobijen postupkom prema zahtevu 7 ili 8.
10.Postupak prema bilo kom od zahteva 7 do 9, gde trans-(-)-Δ9-tetrahidrokanabinol je prisutan u prvoj kompoziciji u količini od 0.75 do 1.25 molarnih ekvivalenata, poželjno od 0.9 do 1.1 molarnih ekvivalenata, poželjnije od 0.95 do 1.25 molarnih ekvivalenata i čak poželjnije 1 molarni ekvivalent po molarnom ekvivalentu trans-(+)-Δ9-tetrahidrokanabinola.
11.Postupak prema bilo kom od zahteva 7 do 10, gde (±)-Δ9-tetrahidrokanabinol obuhvata bar 95% u odnosnu na težinu, poželjno bar 98% u odnosu na težinu i poželjnije bar 99% u odnosu na težinu trans-(-)-Δ9-tetrahidrokanabinola i trans-(+)-Δ9-tetrahidrokanabinola u odnosu na ukupnu količinu kanabinoida.
MEP-2016-55A 2004-11-22 2005-11-18 POSTUPCI ZA PREČIŠĆAVANJE TRANS-(-)-Δ9-TETRAHIDROKANABINOLA l TRANS-(+) - Δ9 - TETRAHIDROKANABINOLA ME02403B (me)

Applications Claiming Priority (2)

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US63055604P 2004-11-22 2004-11-22
EP10179374.3A EP2356987B1 (en) 2004-11-22 2005-11-18 Methods for purifying trans-(-)-delta9-tetrahydrocannabinol and trans-(+)-delta9-tetrahydrocannabinol

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ME02403B true ME02403B (me) 2016-09-20

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MEP-2015-186A ME02306B (me) 2004-11-22 2005-11-18 Postupci za prečišćavanje trans-(-)-Δ⁹-tetrahidrokanabinola i trans-(+)- Δ⁹-tetrahidrokarabinola

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KR (1) KR100919719B1 (me)
CN (2) CN101076329B (me)
AR (1) AR054989A1 (me)
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CA (2) CA2921590C (me)
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PL (3) PL2356987T3 (me)
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TW (2) TWI369203B (me)
UA (1) UA88491C2 (me)
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Families Citing this family (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI369203B (en) 2004-11-22 2012-08-01 Euro Celtique Sa Methods for purifying trans-(-)-△9-tetrahydrocannabinol and trans-(+)-△9-tetrahydrocannabinol
TWI366460B (en) * 2005-06-16 2012-06-21 Euro Celtique Sa Cannabinoid active pharmaceutical ingredient for improved dosage forms
JP2009510078A (ja) 2005-09-29 2009-03-12 エーエムアール テクノロジー インコーポレイテッド Δ−９−テトラヒドロカンナビノールの生成法
US8980940B2 (en) 2006-11-10 2015-03-17 Johnson Matthey Public Limited Company Stable cannabinoid compositions and methods for making and storing them
US8039509B2 (en) 2006-11-10 2011-10-18 Johnson Matthey Public Limited Company Composition comprising (−)-Δ9-trans-tetrahydrocannabinol
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
CA2751741C (en) * 2008-02-06 2018-07-10 Mallinckrodt Inc. Process for the preparation of (-) -delta 9-tetrahydrocannabinol
US10624859B2 (en) 2012-08-20 2020-04-21 Rhodes Technologies Systems and methods for increasing stability of dronabinol compositions
US10610512B2 (en) 2014-06-26 2020-04-07 Island Breeze Systems Ca, Llc MDI related products and methods of use
US10207198B2 (en) 2015-01-22 2019-02-19 Phytoplant Research S.L. Methods of purifying cannabinoids using liquid:liquid chromatography
US10155708B2 (en) 2015-01-22 2018-12-18 Phytoplant Research S.L. Methods of purifying cannabinoids, compositions and kits thereof
US11034639B2 (en) 2015-01-22 2021-06-15 Phytoplant Research S.L. Methods of purifying cannabinoids using liquid:liquid chromatography
CN106268657A (zh) * 2015-05-14 2017-01-04 株式会社大赛璐 光学异构体用分离剂
US10059683B2 (en) 2015-07-10 2018-08-28 Noramco, Inc. Process for the production of cannabidiol and delta-9-tetrahydrocannabinol
EP3455213B1 (en) * 2016-05-13 2021-11-24 Symrise AG Method for purifying cannabinoid compounds via simulated moving bed chromatography
US10499584B2 (en) 2016-05-27 2019-12-10 New West Genetics Industrial hemp Cannabis cultivars and seeds with stable cannabinoid profiles
US10399920B2 (en) 2016-06-01 2019-09-03 S&B Pharma, Inc. Crystalline form of cannabidiol
US10239808B1 (en) 2016-12-07 2019-03-26 Canopy Holdings, LLC Cannabis extracts
CN106810426B (zh) * 2016-12-29 2020-05-08 暨明医药科技（苏州）有限公司 一种大麻二酚的合成方法
US11213558B2 (en) 2017-05-17 2022-01-04 Orochem Technologies, Inc. CBX extraction-isolation process
US10189762B1 (en) 2017-07-07 2019-01-29 Orochem Technologies, Inc. Process for purification and separation of cannabinoids, from dried hemp and cannabis leaves
CN111372907A (zh) * 2017-09-01 2020-07-03 普优峰全球股份有限公司 合成大麻二酚组合物和用于制备其的方法
EP3745884A1 (en) 2018-01-31 2020-12-09 Canopy Holdings, Llc Hemp powder
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
CR20200417A (es) * 2018-03-07 2021-03-31 Socati Tech Oregon Llc Aislamiento continuo de cannabidiol y conversión de cannabidinol a 8-tetrahidrocannabinol y 9-tetrahidrocannabinol
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
CN112292368B (zh) * 2018-06-28 2024-02-02 西姆莱斯有限公司 （+）-大麻素类的合成及其治疗作用
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
US11040932B2 (en) 2018-10-10 2021-06-22 Treehouse Biotech, Inc. Synthesis of cannabigerol
EP3873459A1 (en) 2018-10-31 2021-09-08 Enantia, S.L. Solid compositions of cocrystals of cannabinoids
EP3653596A1 (en) * 2018-11-14 2020-05-20 Indena S.p.A. Continuous flow synthesis of cannabidiol
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
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
WO2020248062A1 (en) * 2019-06-11 2020-12-17 Canopy Growth Corporation Improved methods for cannabinoid isomerization
CA3142957A1 (en) 2019-06-11 2020-12-17 Canopy Growth Corporation Improved methods for converting cannabidiol into delta8-tetrahydrocannabinol
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
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
JP7444995B2 (ja) * 2019-10-21 2024-03-06 エソレイト・リミテッド 超微粒化合物およびその製造
GB2588455B (en) * 2019-10-25 2022-12-21 Gw Res Ltd Cannabinoid compound
GB2588456B (en) * 2019-10-25 2023-02-01 Gw Res Ltd Cannabinoid compound
GB2588457B (en) * 2019-10-25 2022-12-21 Gw Res Ltd Cannabinoid compound
AU2021235467A1 (en) 2020-03-12 2021-10-07 Council Of Scientific And Industrial Research Process for the synthesis of cannabidiol and intermediates thereof
US12029718B2 (en) 2021-11-09 2024-07-09 Cct Sciences, Llc Process for production of essentially pure delta-9-tetrahydrocannabinol
US12195438B2 (en) 2020-12-10 2025-01-14 Kazmira Llc. Process for removing THC from cannabinoids
CN113336705B (zh) * 2021-08-09 2021-12-10 中国农业科学院农产品加工研究所 一种大麻二酚-2-咪唑-1-甲酸酯及其应用
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
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
CN115784836A (zh) * 2022-12-08 2023-03-14 南京康立瑞生物科技有限公司 一种高选择性的制备反式-薄荷基-2,8-二烯-1-醇的方法

Family Cites Families (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3507885A (en) 1966-03-25 1970-04-21 Hoffmann La Roche 3-alkyl-6h-dibenzo(b,d)pyrans
CH481911A (de) 1967-05-19 1969-11-30 Theodor Dr Petrzilka Verfahren zur Herstellung von tricyclischen Verbindungen
US3854480A (en) 1969-04-01 1974-12-17 Alza Corp Drug-delivery system
US3668224A (en) 1970-07-02 1972-06-06 Theodor Petrzilka PROCESS OF PRODUCING 6a, 10a-TRANS-6a,7,8,10a-TETRAHYDRODIBENZO (b,d)-PYRANS
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
US4381399A (en) 1981-12-21 1983-04-26 Aerojet-General Corporation Purification of tetrahydrodibenzo[b,d]pyrans from crude synthetic mixtures
US4970075A (en) 1986-07-18 1990-11-13 Euroceltique, S.A. Controlled release bases for pharmaceuticals
US4861598A (en) 1986-07-18 1989-08-29 Euroceltique, S.A. Controlled release bases for pharmaceuticals
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
US6703418B2 (en) 1991-02-26 2004-03-09 Unimed Pharmaceuticals, Inc. Appetite stimulation and induction of weight gain in patients suffering from symptomatic HIV infection
US5389375A (en) 1993-05-21 1995-02-14 University Of Mississippi Stable suppository formulations effecting bioavailability of Δ9 -thc
US5965161A (en) 1994-11-04 1999-10-12 Euro-Celtique, S.A. Extruded multi-particulates
WO1996041626A1 (en) 1995-06-12 1996-12-27 G.D. Searle & Co. Compositions comprising a cyclooxygenase-2 inhibitor and a 5-lipoxygenase inhibitor
US6017963A (en) 1995-11-14 2000-01-25 Euro-Celtique, S.A. Formulation for intranasal administration
US6328992B1 (en) 1997-03-03 2001-12-11 Lawrence L. Brooke Cannabinoid patch and method for cannabis transdermal delivery
GB9726916D0 (en) 1997-12-19 1998-02-18 Danbiosyst Uk Nasal formulation
US20020039795A1 (en) 1998-10-26 2002-04-04 Elsohly Et Al Method of preparing delta-9-tetrahydrocannabinol
US6730519B2 (en) 1998-10-26 2004-05-04 The University Of Mississippi Method of preparing delta-9-tetrahydrocannabinol
US6509005B1 (en) 1998-10-27 2003-01-21 Virginia Commonwealth University Δ9 Tetrahydrocannabinol (Δ9 THC) solution metered dose inhaler
FI990915A0 (fi) 1999-04-23 1999-04-23 Orion Yhtymae Oyj Jauheinhalaattori
US6403126B1 (en) 1999-05-26 2002-06-11 Websar Innovations Inc. Cannabinoid extraction method
US6555139B2 (en) 1999-06-28 2003-04-29 Wockhardt Europe Limited Preparation of micron-size pharmaceutical particles by microfluidization
US6747058B1 (en) 1999-08-20 2004-06-08 Unimed Pharmaceuticals, Inc. Stable composition for inhalation therapy comprising delta-9-tetrahydrocannabinol and semiaqueous solvent therefor
US6620351B2 (en) 2000-05-24 2003-09-16 Auburn University Method of forming nanoparticles and microparticles of controllable size using supercritical fluids with enhanced mass transfer
GB2368061B (en) 2000-10-20 2005-05-11 Gw Pharmaceuticals Ltd Dose dispensing apparatus
KR100968128B1 (ko) 2000-10-30 2010-07-06 유로-셀티크 소시에떼 아노뉨 서방성 하이드로코돈 제형
US6730330B2 (en) 2001-02-14 2004-05-04 Gw Pharma Limited Pharmaceutical formulations
CH695661A5 (de) * 2001-03-06 2006-07-31 Forsch Hiscia Ver Fuer Krebsfo Pharmazeutische Zusammensetzung.
US7399872B2 (en) 2001-03-07 2008-07-15 Webster G R Barrie Conversion of CBD to Δ8-THC and Δ9-THC
US20030050334A1 (en) 2001-04-30 2003-03-13 Murty Ram B. Process for extraction of Delta-9-Tetrahydrocannabinol and other related cannabinoids and preparation of specific strength marijuana cigarettes
GB0112752D0 (en) 2001-05-25 2001-07-18 Johnson Matthey Plc Synthesis of cannabinoids
US20030044458A1 (en) 2001-08-06 2003-03-06 Curtis Wright Oral dosage form comprising a therapeutic agent and an adverse-effect agent
DE60321318D1 (de) * 2002-02-01 2008-07-10 Resolution Chemicals Ltd Gewinnung von delta-9 tetrahydrocannabinol
AU2002242779A1 (en) 2002-02-21 2003-09-09 Timothee Biel Device for driving motor vehicles, in particular with hybrid propulsion
UA79281C2 (en) 2002-04-03 2007-06-11 Solvay Pharm Bv Stabilized composition comprising a natural cannabinoid compound and process for the preparation thereof
US6946150B2 (en) 2002-08-14 2005-09-20 Gw Pharma Limited Pharmaceutical formulation
GB0222077D0 (en) 2002-09-23 2002-10-30 Gw Pharma Ltd Methods of preparing cannabinoids from plant material
CN100455576C (zh) 2002-11-12 2009-01-28 马林克罗特公司 大麻素的结晶衍生物及大麻素的纯化方法
US20040229939A1 (en) 2003-02-14 2004-11-18 Chowdhury Dipak K. Tetrahydrocannabinol compositions and methods of manufacture and use thereof
MXPA06005015A (es) 2003-11-05 2007-11-22 Unimed Pharmaceuticals Inc Composiciones delta-9-thc y metodos para tratar sintomas asociados con esclerosis multiple.
GB0329635D0 (en) * 2003-12-23 2004-01-28 Johnson Matthey Plc Process for purifying trans-tetrahydrocannabinol
CA2573859A1 (en) 2004-07-19 2006-01-26 Cilag Ltd. Method for obtaining pure tetrahydrocannabinol
GB0425445D0 (en) 2004-11-18 2004-12-22 Smithkline Beecham Corp Novel compositions
TWI369203B (en) * 2004-11-22 2012-08-01 Euro Celtique Sa Methods for purifying trans-(-)-△9-tetrahydrocannabinol and trans-(+)-△9-tetrahydrocannabinol
TWI366460B (en) 2005-06-16 2012-06-21 Euro Celtique Sa Cannabinoid active pharmaceutical ingredient for improved dosage forms
CA2694325C (en) 2007-07-30 2015-09-22 Alltranz Inc. Prodrugs of cannabidiol, compositions comprising prodrugs of cannabidiol and methods of using the same
US8642645B2 (en) * 2011-05-20 2014-02-04 Brooks Kelly Research, LLC. Pharmaceutical composition comprising Cannabinoids

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