CA3089490A1 - Procedes de purification de cannabinoides par chromatographie liquide : liquide - Google Patents

Procedes de purification de cannabinoides par chromatographie liquide : liquide Download PDF

Info

Publication number
CA3089490A1
CA3089490A1 CA3089490A CA3089490A CA3089490A1 CA 3089490 A1 CA3089490 A1 CA 3089490A1 CA 3089490 A CA3089490 A CA 3089490A CA 3089490 A CA3089490 A CA 3089490A CA 3089490 A1 CA3089490 A1 CA 3089490A1
Authority
CA
Canada
Prior art keywords
hours
cannabinoids
hexane
solvent mixture
thc
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CA3089490A
Other languages
English (en)
Inventor
Xavier NADAL ROURA
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.)
Phytoplant Research SL
Original Assignee
Phytoplant Research SL
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US15/882,516 external-priority patent/US10207198B2/en
Application filed by Phytoplant Research SL filed Critical Phytoplant Research SL
Publication of CA3089490A1 publication Critical patent/CA3089490A1/fr
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C07C37/004—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from plant material or from animal material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0203—Solvent extraction of solids with a supercritical fluid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0288—Applications, solvents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0492—Applications, solvents used
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
    • B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
    • B01D15/1892—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns the sorbent material moving as a whole, e.g. continuous annular chromatography, true moving beds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D9/00—Crystallisation
    • B01D9/0004—Crystallisation cooling by heat exchange
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring
    • C07C39/19—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring containing carbon-to-carbon double bonds but no carbon-to-carbon triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/19—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups having unsaturation outside the 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
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Analytical Chemistry (AREA)
  • Botany (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne des procédés de purification d'un ou de plusieurs cannabinoïdes à partir d'un matériau végétal à l'aide de systèmes de solvants biphasiques uniques et d'une chromatographie liquide-liquide comme la chromatographie de séparation par centrifugation (CPC) ou la chromatographie à contre-courant (CCC). La présente invention concerne également des cannabinoïdes purifiés tels que CBG, CBGA, CBGV, CBD, CBDA, CBDV, THC, THCA et THCV, des compositions comprenant un ou plusieurs de ces cannabinoïdes produits par le procédé selon l'invention, et des méthodes de traitement d'une maladie ou d'un état pathologique utilisant de tels cannabinoïdes purifiés et compositions.
CA3089490A 2018-01-29 2019-01-29 Procedes de purification de cannabinoides par chromatographie liquide : liquide Pending CA3089490A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US15/882,516 2018-01-29
US15/882,516 US10207198B2 (en) 2015-01-22 2018-01-29 Methods of purifying cannabinoids using liquid:liquid chromatography
PCT/EP2019/052069 WO2019145552A1 (fr) 2018-01-29 2019-01-29 Procédés de purification de cannabinoïdes par chromatographie liquide : liquide

Publications (1)

Publication Number Publication Date
CA3089490A1 true CA3089490A1 (fr) 2019-08-01

Family

ID=65276144

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3089490A Pending CA3089490A1 (fr) 2018-01-29 2019-01-29 Procedes de purification de cannabinoides par chromatographie liquide : liquide

Country Status (9)

Country Link
EP (1) EP3746419A1 (fr)
CN (1) CN111788171A (fr)
AU (1) AU2019211188A1 (fr)
CA (1) CA3089490A1 (fr)
CL (1) CL2020001964A1 (fr)
CO (1) CO2020009747A2 (fr)
IL (1) IL276010A (fr)
MX (1) MX2020007960A (fr)
WO (1) WO2019145552A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220242810A1 (en) * 2019-06-14 2022-08-04 Purisys Llc Crystalline cannabigerol
CN110590511B (zh) * 2019-09-11 2021-05-28 上海同田生物技术股份有限公司 一种同时分离次大麻二酚和大麻萜酚的方法
CN112279752B (zh) * 2020-10-30 2022-11-11 云南芙雅生物科技有限公司 用于工业大麻的大麻素二氧化碳超临界提取方法
CN113135885A (zh) * 2021-04-07 2021-07-20 上海同田生物技术有限公司 一种高速逆流色谱分离纯化四氢次大麻酚的方法
US11857590B2 (en) * 2021-10-26 2024-01-02 Ecofibre Limited Systems and methods for producing hemp extracts and compositions
IL312245A (en) 2021-10-26 2024-06-01 Ecofibre Usa Inc Methods of treating endometriosis and other non-cancerous gynecological disorders with hemp extract
CA3235078A1 (fr) 2021-10-26 2023-04-05 Ecofibre USA Inc. Methodes de traitement du cancer de l'endometre a l'aide d'extrait de chanvre
CN115385780B (zh) * 2022-08-26 2024-02-27 晨光生物科技集团股份有限公司 一种次大麻二酚结晶多晶型物及其制备方法和应用
WO2024091989A1 (fr) 2022-10-26 2024-05-02 Ecofibre USA Inc. Compositions stabilisées comprenant du cannabidiol

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR0166088B1 (ko) 1990-01-23 1999-01-15 . 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도
US5376645A (en) 1990-01-23 1994-12-27 University Of Kansas Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof
GB9518953D0 (en) 1995-09-15 1995-11-15 Pfizer Ltd Pharmaceutical formulations
WO2000035298A1 (fr) 1996-11-27 2000-06-22 Wm. Wrigley Jr. Company Chewing-gum contenant des agents medicamenteux actifs
GB9711643D0 (en) 1997-06-05 1997-07-30 Janssen Pharmaceutica Nv Glass thermoplastic systems
JP2005526715A (ja) * 2002-02-01 2005-09-08 レゾリューション ケミカルズ リミテッド Δ９−テトラヒドロカンナビノールの製造
US20080103193A1 (en) * 2006-10-26 2008-05-01 Trevor Percival Castor Methods for making compositions and compositions for treating pain and cachexia
US10155708B2 (en) * 2015-01-22 2018-12-18 Phytoplant Research S.L. Methods of purifying cannabinoids, compositions and kits thereof
PT3247371T (pt) * 2015-01-22 2020-07-02 Phytoplant Res S L Métodos de purificação de canabinóides, composições e kits associados
EP3061510A1 (fr) 2015-02-27 2016-08-31 Bionorica Ethics GmbH Chromatographie de partition cpc de cannabinoïdes
BG112018A (bg) * 2015-05-22 2016-11-30 "Побелч-Гле" Оод Метод за получаване на канабиноиден извлек от коноп

Also Published As

Publication number Publication date
AU2019211188A1 (en) 2020-07-30
IL276010A (en) 2020-08-31
EP3746419A1 (fr) 2020-12-09
CL2020001964A1 (es) 2020-12-18
CN111788171A (zh) 2020-10-16
CO2020009747A2 (es) 2020-08-21
MX2020007960A (es) 2020-09-24
WO2019145552A1 (fr) 2019-08-01

Similar Documents

Publication Publication Date Title
US10207199B2 (en) Methods of purifying cannabinoids using liquid:liquid chromatography
AU2021203749B2 (en) Methods of purifying cannabinoids, compositions and kits thereof
US11034639B2 (en) Methods of purifying cannabinoids using liquid:liquid chromatography
CA3089490A1 (fr) Procedes de purification de cannabinoides par chromatographie liquide : liquide
US10155708B2 (en) Methods of purifying cannabinoids, compositions and kits thereof
US10751380B2 (en) Compound and method for treating spasms, inflammation and pain
TW200940081A (en) A plant composition
CN108191616B (zh) 白及中具有选择性丁酰胆碱酯酶抑制作用的单体成分及其用途
CN110452110B (zh) 一种间苯三酚类天然药物及其制备方法和用途
WO2017006407A1 (fr) Inhibiteur de la mort des cellules nerveuses, agent anti-maladie d'alzheimer, inhibiteur de l'hypofonction cérébrale, médicament ou aliment présentant un effet anti-maladie d'alzheimer ou un effet d'inhibition de l'hypofonction cérébrale, et méthode de production d'inhibiteur de la mort des cellules nerveuses
CN104086559B (zh) 一种二萜类化合物的晶型
CA2909280C (fr) Alcaloide chromone dysoline pour le traitement du cancer et de troubles inflammatoires
CN106977560B (zh) 2S-cardiospermin-5-benzoate的制备及其在制备治疗类风湿关节炎药物中的应用
WO2006012779A1 (fr) Extraits de wikstroemia indeca, production de ceux-ci et utilisation de ceux-ci dans la production de produits pharmaceutiques anti-inflammatoires
CN107365316B (zh) 石松生物碱lycoplanineA及其药物组合物与其制备方法和应用
CN109776350A (zh) 一种含有多不饱和脂肪链的酰胺类化合物
JPH07149630A (ja) 血管拡張剤
WO2007101365A1 (fr) Nouveau composé de flavane et ses utilisations