WO2018167038A1 - Procédé d'extraction de cannabinoïdes à partir d'une matière végétale de cannabis - Google Patents

Procédé d'extraction de cannabinoïdes à partir d'une matière végétale de cannabis Download PDF

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Publication number
WO2018167038A1
WO2018167038A1 PCT/EP2018/056201 EP2018056201W WO2018167038A1 WO 2018167038 A1 WO2018167038 A1 WO 2018167038A1 EP 2018056201 W EP2018056201 W EP 2018056201W WO 2018167038 A1 WO2018167038 A1 WO 2018167038A1
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Prior art keywords
pressure tank
liquid extract
cannabinoids
cannabis plant
solvent
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PCT/EP2018/056201
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English (en)
Inventor
Filip VOROBJOV
Erik Gydesen SØGAARD
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Aalborg Universitet
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Publication of WO2018167038A1 publication Critical patent/WO2018167038A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • 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
    • B01D11/028—Flow sheets
    • B01D11/0284—Multistage extraction
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/37—Extraction at elevated pressure or temperature, e.g. pressurized solvent extraction [PSE], supercritical carbon dioxide extraction or subcritical water extraction

Definitions

  • the present invention relates to a method for extracting cannabinoids from cannabis plant material using an extractor with super critical carbon dioxide.
  • Biodynamic growth of Cannabis Sativa is of increased interest. Parts of the plant are already being used commercially. The seeds are used for dietary
  • the stems that consist of fibers are used for paper or ropes.
  • Cannabinoids are unique molecules that can only be found in subspecies of hemp (cannabis). Cannabis (hemp), together with the genus Humulus (hops), belongs to the family of Cannabinaceae, with hops, for instance, not containing any cannabinoids.
  • the cannabinoids are divided into three groups:
  • phytocannabinoids that are found in cannabis, and synthetic cannabinoids.
  • cannabinoids for purposes such as antibiotics, anti-inflammatory drugs, analgesics, and antispasticity drugs.
  • the leaves of cannabis furthermore comprise a unique composition of proteins, which contain all the essential amino acids for humans as well as for e.g. pigs.
  • the cannabis leaves are also known to stimulate appetite. Hence, there is a possibility of utilizing hemp leaves for dietary supplements and/or animal feed. However, the presence of the cannabinoids in the leaves is blocking this possibility. Summary of the invention
  • This invention provides a method for extracting cannabinoids from cannabis plant material.
  • the present invention allows for complete extraction of
  • cannabinoids from cannabis plant material, thereby making it possible to utilize e.g. hemp leaves for dietary supplements and/or animal feed.
  • a first aspect relates to a process for extracting cannabinoids from cannabis plant material comprising the steps of:
  • a pressure tank subjecting the cannabis plant material to a first extraction step with a one-phase solvent system comprising supercritical carbon dioxide and optionally a non-polar co-solvent, and performed at a temperature of about 10-70 degrees Celsius;
  • a second aspect relates to a cannabis plant fiber material with a reduced content of cannabinoids produced by the process according to the present invention, wherein the cannabinoid content, such as the tetrahydrocannabinol content, is 0.05% at the most, and wherein the pressure within the pressure tank during the extraction steps are at least 400 bar.
  • a third aspect relates to a cannabis plant fiber material with a reduced content of cannabinoids produced by the process according to the present invention, wherein the cannabinoid content, such as the tetrahydrocannabinol content, is
  • a fourth aspect relates to a process for extracting cannabinoids from cannabis plant material comprising the steps of:
  • Hemp is the commonly used name for plants of the cannabis genus.
  • the two commonly known subspecies are Cannabis Sativa subsp. Sativa and Cannabis Sativa subsp. Indica.
  • the subspecies Sativa has an origin north of latitude 30° N and is primarily a fiber type and Indica has the origin south of 30° N and is primarily a drug type.
  • Cannabis Sativa The chemical and morphological properties of the subspecies of Cannabis Sativa are environmentally modifiable and can vary depending on the conditions and location, which is why Cannabis Sativa normally refers to all subspecies. So far, 70 different cannabinoids have been identified. The cannabinoids can be divided into the following subclasses:
  • CBD Cannabidiol type
  • THC Tetrahydrocannabinol type
  • Cannabis Sativa can be categorized as either a fiber type/industrial or a drug type.
  • the content of CBD is in inverse proportions to the content of THC, and depending on the content of these, the type of Cannabis Sativa can be determined.
  • the industrial type is defined as having a content of THC at maximum 0.2 % in Europe and 0.3 % in Canada.
  • Cannabis Sativa makes it impossible to get high from eating or smoking it and it is therefore considered safe. However, pigs may still respond to such
  • a first aspect relates to a process for extracting cannabinoids from cannabis plant material comprising the steps of:
  • a pressure tank subjecting the cannabis plant material to a first extraction step with a one-phase solvent system comprising supercritical carbon dioxide and optionally a non-polar co-solvent, and performed at a temperature of about 10-70 degrees Celsius;
  • a fourth aspect relates to a process for extracting cannabinoids from cannabis plant material comprising the steps of:
  • the term "winterization” as used herein refers to a process which involves the chilling of the first liquid extract from the pressure tank in ethanol at temperatures below 0 degrees Celsius, such as -1 12 to -5 degrees Celsius, for removal of amongst others fats and waxes, optionally combined with filtration and/or centrifugation.
  • the first liquid extract is subjected to an ethanolic precipitation to remove a substantial proportion of non-cannabinoid materials, e.g. waxes, wax esters and glycerides, unsaturated fatty acid residues, terpenes, carotenes, and flavonoids.
  • the precipitation is preferably performed at low temperatures of -20 degrees Celsius or lower, such as within the range of -1 12 to -20 degrees
  • the solution is then filtrated to remove precipitated matter, and ethanol is subsequently removed to collect a second liquid extract.
  • the inventors have found that impurities are still present after cold filtration.
  • the latter one can be potentially dangerous for humans if consumed in large quantities.
  • the second liquid extract is optionally heat treated (1 -2 hours at 1 15-125 degrees Celsius, or at 135-145 degrees Celsius, depending on the cannabis origin/species) to secure that all the cannabinoids are decarboxylated.
  • the second liquid extract is then solubilized in a non-polar solvent; and extracted with an aqueous basic solution.
  • the impurities are degraded into water soluble components and will thus be removed from the non-polar solvent phase.
  • the neutral form of the cannabinoids is not susceptible to degradation by this method.
  • the non-polar solvent phase is then collected, and the non-polar solvent is removed (e.g. by evaporation under reduced pressure) to collect the purified neutral form of the cannabinoids.
  • non-polar represents a solvent, which is relatively inert to proton activity, i.e., not acting as a proton donor.
  • the non- polar solvent is selected from the group of saturated hydrocarbons.
  • saturated hydrocarbon refers to any hydrocarbon, which does not contain any carbon-to-carbon double bonds or carbon-to-carbon triple bonds.
  • saturated hydrocarbons include, but are not limited to pentanes (isopentane, n-pentane, cyclopentane), hexanes (n-hexane, cyclohexane), heptanes (n-heptane, cycloheptane), octanes (n-octane, isooctane), nonanes (n-nonane), decanes, and mixtures thereof.
  • the saturated hydrocarbons have a boiling point within the range of 30-180 degrees Celsius, and even more preferably within the range of 30-120 degrees Celsius.
  • the non-polar solvent is selected from the group consisting of isopentane, n-pentane, cyclopentane, n-hexane, cyclohexane, n- heptane, cycloheptane, n-octane, isooctane, and mixtures thereof.
  • Living cannabis leaves contain about 80% w/w water. To perform an efficient extraction, the leaves should be dried, e.g. at 90-105 degrees Celsius, to reduce their water content, since the cannabinoids are not soluble in water. Hence, any water present in the leaves will complicate the extraction process.
  • the cannabis plant material for use in the present invention should have a water content of at most 60% w/w, such as within the range of 0-55% w/w, e.g. within the range of 1 -50% w/w, such as within the range of 2-45% w/w, e.g. within the range of 3-40% w/w, such as within the range of 4-35% w/w, e.g. within the range of 5-30% w/w, such as within the range of 10-25% w/w, e.g. within the range of 10-20% w/w, preferably at most 10% w/w.
  • the drying process may to some extend result in decarboxylation of the acid form of the cannabinoids to the neutral form of the cannabinoids.
  • the cannabis plant material for use in the present invention are subjected to a decarboxylation process prior to the extraction process.
  • a decarboxylation process may comprise the step of heating the cannabis plant material for about 30 minutes at 1 15-125 degrees Celsius, or for about 15 minutes at 135-145 degrees Celsius, depending on the cannabis origin/species. It is crucial that the heating temperature and time is controlled, since the cannabinoids may risk degradation.
  • the cannabis plant material may be triturated/shred/grinded prior to the extraction process to increase the penetration rate of the one-phase solvent system.
  • the density of the system can be altered.
  • the solvent can therefore have its abilities designed and changed for a given purpose.
  • Supercritical carbon dioxide is mixable with compounds having up to 10 carbon atoms. Compounds with polar groups complicates the process, and it might not be possible at all to extract these compounds with pure carbon dioxide. Often the extraction will take a lot of time, and not all the compounds will be removed. SCF's can be divided into low Tc fluids and high Tc fluids.
  • the first three in the table are considered as low Tc fluids and the last four are high Tc fluids. There are strong differences in solvent power and selectivity between the two groups. To decide which SCF to use for extraction of cannabinoids from plant material, such as leaf or flowers, of Cannabis Sativa, the nature of the cannabinoids needed to be evaluated.
  • Cannabis Sativa of the type Fedora 17 has been used for extraction, which is a type that contains a maximum of 0.2 % w/w HTC and then the inverse proportion of CBD (5% w/w).
  • Other cannabinoids are only present in trace amounts.
  • Both THC and CBD are aromatic compounds that consist of carbon, hydrogen and oxygen. Both have the empiric formula C21 H30O2. They are capable of making hydrogen bonds.
  • Carbon dioxide is one of the most used SCF's for extraction. It can be used for non-polar components alone or for polar components with a co-solvent. Carbon dioxide is stabile even at high pressures and temperatures and is rarely reacting with the component that is being extracted. Furthermore, it is easy to recover carbon dioxide at ambient conditions, since it will be in its gas state. Most other solvents will need some kind of unit operation to be recovered, which makes the process much costlier.
  • Carbon dioxide in supercritical fluid form is used in the present invention, optionally together with a co-solvent, for the extraction of cannabinoids from the cannabis plant material.
  • the co-solvent must be miscible with the supercritical fluid to form a one-phase solvent system.
  • the density of the one-phase solvent system is dependent on the temperature and the pressure within the pressure tank.
  • the correct pressure may be solely obtained by pressurized carbon dioxide, or may partly be adjusted by inert pressurized gasses, such as nitrogen, helium, and argon.
  • the optimal density of the one-phase solvent system is at least 750 kg per cubic meter.
  • the temperature should be within the range of 30-60 degrees Celsius to avoid degradation of the cannabinoids during the extraction process.
  • the extraction step is performed at a temperature of about 10-70 degrees Celsius, such as within the range of 15-65 degrees Celsius, e.g. within the range of 20-60 degrees Celsius, such as within the range of 25-55 degrees Celsius, e.g. within the range of 30-50 degrees Celsius, such as within the range of 35-45 degrees Celsius, e.g. within the range of 40-45 degrees Celsius.
  • the extraction step is performed at a temperature of about 30-60 degrees Celsius, such as within the range of 32-58 degrees Celsius, e.g. within the range of 34-56 degrees Celsius, such as within the range of 36-54 degrees Celsius, e.g. within the range of 38-52 degrees Celsius, such as within the range of 40-50 degrees Celsius, e.g. within the range of 42-48 degrees Celsius, such as within the range of 44-46 degrees Celsius.
  • the pressure within the pressure tank during the extraction steps are at least 74 bar, such as within the range of 75-1000 bar, e.g with n the range of 80-995 bar, such as within the range of 90-990 bar, e.g.
  • n the range of 100-985 bar such as within the range of 1 10-980 bar, e g- with n the range of 120-975 bar, such as within the range of 130-970 bar, e g- with n the range of 140-965 bar, such as within the range of 150-960 bar, e g- with n the range of 160-955 bar, such as within the range of 170-950 bar, e g- with n the range of 180-925 bar, such as within the range of 190-900 bar, e g- with n the range of 200-875 bar, such as within the range of 225-850 bar, e g- with n the range of 250-825 bar, such as within the range of 275-800 bar, e g- with n the range of 300-750 bar, such as within the range of 325-700 bar, e g- with n the range of 350-650 bar, such as within the range of 375-600 bar, e g- with n the range of 400
  • the pressure within the pressure tank during the extraction steps are at least 400 bar. Such pressure will result in denaturation of the proteins within the plant material, such as the leaves.
  • the pressure within the pressure tank during the extraction steps are at most 400 bar. Such pressure will avoid denaturation of the proteins within the plant material, such as the leaves.
  • the density of the one-phase solvent system is within the range of 750-1000 kg per cubic meter, e.g. within the range of 765-985 kg per cubic meter, such as within the range of 790-970 kg per cubic meter, e.g. within the range of 805-955 kg per cubic meter, such as within the range of 820- 940 kg per cubic meter, e.g. within the range of 835-905 kg per cubic meter, such as within the range of 850-890 kg per cubic meter, e.g. within the range of 865-875 kg per cubic meter.
  • the process further comprises the steps of:
  • the first and/or second and/or further extraction step is performed for at least 30 minutes before collecting/removing a liquid extract from the pressure tank.
  • the injection of the carbon dioxide and optionally the co-solvent into the pressure tank is performed simultaneously with collecting/removing a liquid extract from the pressure tank.
  • the injection of the carbon dioxide and optionally the co-solvent is performed into the bottom of the pressure tank, while the collection/removal of a liquid extract is performed in the top of the pressure tank.
  • the co-solvent is present in an amount of from about 0 to 20 weight % of the total weight of the one-phase solvent system being used, such as within the range of 1 -18 wt.%, e.g. within the range of 2-16 wt.%, such as within the range of 3-14 wt.%, e.g. within the range of 4-12 wt.%, such as within the range of 5-10 wt.%, e.g. within the range of 6-9 wt.%, such as within the range of 7-8 wt.% of the total weight of the one-phase solvent system being used.
  • the one-phase solvent system further comprises a co-solvent selected from the group consisting of pentane, cyclopentane, hexane, cyclohexane, heptane, octane, benzene, toluene, and mixtures thereof.
  • a co-solvent selected from the group consisting of pentane, cyclopentane, hexane, cyclohexane, heptane, octane, benzene, toluene, and mixtures thereof.
  • a second aspect relates to a cannabis plant material fiber material with a reduced content of cannabinoids produced by the process according to the present invention, wherein the tetrahydrocannabinol content is 0.05% w/w at the most.
  • a second aspect relates to a cannabis plant fiber material with a reduced content of cannabinoids produced by the process according to the present invention, wherein the cannabinoid content, such as the tetrahydrocannabinol content, is 0.05% at the most, and wherein the pressure within the pressure tank during the extraction steps are at least 400 bar.
  • the pressure within the pressure tank during the extraction steps are at least 400 bar.
  • a third aspect relates to a cannabis plant fiber material with a reduced content of cannabinoids produced by the process according to the present invention, wherein the cannabinoid content, such as the tetrahydrocannabinol content, is
  • the tetrahydrocannabinol content is within the range of 0-0.05% w/w, e.g. within the range of 0.001 -0.045% w/w, such as within the range of 0.002-0.040% w/w, e.g. within the range of 0.003-0.035% w/w, such as within the range of 0.004-0.030% w/w, e.g. within the range of 0.005-0.025% w/w, such as within the range of 0.010-0.020% w/w, preferably within the range of 0-0.010 % w/w.
  • the cannabinoid content is within the range of 0- 0.05% w/w, e.g. within the range of 0.001 -0.045% w/w, such as within the range of 0.002-0.040% w/w, e.g. within the range of 0.003-0.035% w/w, such as within the range of 0.004-0.030% w/w, e.g. within the range of 0.005-0.025% w/w, such as within the range of 0.010-0.020% w/w, preferably within the range of 0-0.010 % w/w.
  • the process starts from the CO2 bottle 1 ( Figure 1 ) with a dip tube, ensuring that the CO2 drawn will be in liquid state.
  • the liquid CO2 flows into a pump 3, which pressurizes the liquid CO2 to the desired pressure.
  • a pressure sensor 10 is installed in the pump to indicate to which pressure the liquid has been pressurized to.
  • the fluid then flows through a valve 4, which can be used to isolate the extraction unit 5 from the pump.
  • the extraction unit 5 is a steel vessel of known volume, which is filled with ground cannabis plant material.
  • a heating jacket 6 is positioned around the extraction unit 5 to turn the liquid CO2 into a supercritical fluid (SC-CO2), and use its unique properties in order to extract the cannabinoids from the cannabis plant material.
  • a thermocouple 1 1 is inserted into the wall of the extraction unit 5 in order to monitor the temperature inside of the steel vessel.
  • a pressure relieve valve 7 is connected to the extraction unit 5 to be able to degas the unit. No extract collection is carried out with this valve.
  • the saturated SC-CO2 flows out of the extraction unit 5 into a heater 8 and through a glove valve 9 into a collection vessel (not shown).
  • the heater 8 is used to counter the Joule-Thompson expansion effect, which would turn the SC-CO2 solid upon expansion to atmospheric pressure.
  • a thermocouple 12 monitors the temperature of the heater 8.
  • a volumetric flowmeter 13 monitors the CO2 flow, from which it's possible to determine the flow rate of CO2.
  • the steel vessel is emptied, and the cannabis plant fiber material with a reduced content of cannabinoids is removed.
  • the ethanol is removed from the extract by evaporation.
  • the cannabinoid concentration in the extract is about
  • the extract is heat treated (e.g. oil bath) to 1 10-140 degrees Celsius, preferably in an inert atmosphere, in order for the cannabinoids to decarboxylate.
  • the extract is then cooled, and subsequently mixed with a short- chain saturated hydrocarbon, i.e. pentane.
  • the final mixture is arranged to contain about 6-10% w/w of extract in pentane.
  • An aqueous solution of NaOH is prepared.
  • the concentration shall be
  • the extract solution and the aqueous NaOH solutions are mixed together in a 50:50 proportion together, and shaken rigorously for 2 minutes. The mixture is then centrifuged in order to separate the polar from non-polar phases.
  • the non-polar solution might have some of the saponified fatty acids in the non-polar phase.
  • This problem can be solved by using a solution of NaCI in water.
  • the non-polar and polar phases are mixed and separated. The separation process is quite efficient and can be done via a separation funnel, however for complete separation of phases centrifugation is still recommended.
  • the non-polar phase can be heated up to remove the solvent.
  • the resulting product should have a concentration of cannabinoid of about 85-90%, with the remaining lipids constituting no more than 10% of the product.

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Abstract

La présente invention concerne un procédé d'extraction de cannabinoïdes à partir d'une matière végétale de cannabis à l'aide d'un extracteur à dioxyde de carbone supercritique. Le procédé comprend les étapes consistant à : a) utiliser une matière végétale de cannabis ayant une teneur en eau inférieure ou égale à 60 % p/p, de préférence inférieure ou égale à 10 % p/p ; b1) dans un réservoir sous pression, soumettre la matière végétale de cannabis à une première étape d'extraction au moyen d'un système de solvant à une phase comprenant du dioxyde de carbone supercritique et éventuellement un co-solvant non polaire, et mise en œuvre à une empérature comprise dans la plage allant d'environ 30 à 60 degrés Celsius ; c1) collecter un premier extrait liquide dans le réservoir sous pression ; d) collecter/retirer un produit solide du réservoir sous pression comprenant une matière de fibre végétale de cannabis ayant une teneur réduite en cannabinoïdes ; e) dissoudre le premier extrait liquide en provenance du réservoir sous pression dans de l'éthanol, soumettre la solution à une ou plusieurs étapes de frigélisation, filtrer la solution pour éliminer la matière précipitée, et retirer l'éthanol de sorte à collecter un deuxième extrait liquide ; f) éventuellement, soumettre à un traitement thermique le deuxième extrait liquide à une température comprise dans la plage allant de 100 à 150 degrés Celsius pour décarboxyler toute forme acide des cannabinoïdes en forme neutre des cannabinoïdes ; g) dissoudre le deuxième extrait liquide, éventuellement traité thermiquement, dans un solvant non polaire ; h) extraire le deuxième extrait liquide solubilisé au moyen d'une solution basique aqueuse ; et collecter la phase de solvant non polaire en tant que troisième extrait liquide ; et i) éventuellement, retirer le solvant non polaire de sorte à collecter la forme neutre des cannabinoïdes.
PCT/EP2018/056201 2017-03-15 2018-03-13 Procédé d'extraction de cannabinoïdes à partir d'une matière végétale de cannabis WO2018167038A1 (fr)

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CN110404291A (zh) * 2019-06-11 2019-11-05 健民药业集团股份有限公司 用于制备小儿宣肺止咳糖浆的渗漉罐、渗漉提取系统及其制备方法
FR3091993A1 (fr) * 2019-01-29 2020-07-31 Isp Investments Llc Procede d’obtention d’un extrait de feuilles de patchouli et ses utilisations cosmetiques
WO2020252593A1 (fr) * 2019-06-21 2020-12-24 Hexo Operations Inc. Traitement à l'échelle industrielle de substance de cannabis
CN112279752A (zh) * 2020-10-30 2021-01-29 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
US11021675B2 (en) * 2019-09-13 2021-06-01 Thar Process, Inc. Process for producing refined oils from botanical plant matter using a supercritical fluid
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
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WO2022166301A1 (fr) * 2021-02-07 2022-08-11 浙江双子智能装备有限公司 Procédé d'élimination d'impuretés de cannabis
US11654171B2 (en) 2021-10-26 2023-05-23 Ecofibre Limited Methods of treating ovarian cancer with hemp extract
US11654172B2 (en) 2021-10-26 2023-05-23 Ecofibre Limited Methods of treating endometriosis and other non-cancer gynecological disorders with hemp extract
WO2023076931A3 (fr) * 2021-10-26 2023-07-06 Ecofibre Limited Systèmes et procédés pour produire des compositions et des extraits de chanvre
US12011451B2 (en) 2023-10-25 2024-06-18 Ecofibre USA Inc. Stabilized compositions comprising cannabidiol

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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
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US11654172B2 (en) 2021-10-26 2023-05-23 Ecofibre Limited Methods of treating endometriosis and other non-cancer gynecological disorders with hemp extract
WO2023076931A3 (fr) * 2021-10-26 2023-07-06 Ecofibre Limited Systèmes et procédés pour produire des compositions et des extraits de chanvre
US11793847B2 (en) 2021-10-26 2023-10-24 Ecofibre USA Inc. Methods of treating endometrial cancer using hemp extract
US11857590B2 (en) 2021-10-26 2024-01-02 Ecofibre Limited Systems and methods for producing hemp extracts and compositions
US11975036B2 (en) 2021-10-26 2024-05-07 Ecofibre USA Inc. Methods of treating ovarian cancer with hemp extract
US11986505B2 (en) 2021-10-26 2024-05-21 Ecofibre USA Inc. Methods of treating endometriosis and other noncancer gynecological disorders with hemp extract
US12011451B2 (en) 2023-10-25 2024-06-18 Ecofibre USA Inc. Stabilized compositions comprising cannabidiol

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