WO2020219829A1 - Compositions comprenant des formes non cristallines de cannabidiol - Google Patents

Compositions comprenant des formes non cristallines de cannabidiol Download PDF

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Publication number
WO2020219829A1
WO2020219829A1 PCT/US2020/029745 US2020029745W WO2020219829A1 WO 2020219829 A1 WO2020219829 A1 WO 2020219829A1 US 2020029745 W US2020029745 W US 2020029745W WO 2020219829 A1 WO2020219829 A1 WO 2020219829A1
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WO
WIPO (PCT)
Prior art keywords
composition
cannabidiol
mass
percent
terpene
Prior art date
Application number
PCT/US2020/029745
Other languages
English (en)
Inventor
Nixon MALCOLM
Original Assignee
Natural Extraction Systems, LLC
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 US16/408,428 external-priority patent/US10993928B2/en
Application filed by Natural Extraction Systems, LLC filed Critical Natural Extraction Systems, LLC
Priority to CA3137559A priority Critical patent/CA3137559A1/fr
Publication of WO2020219829A1 publication Critical patent/WO2020219829A1/fr

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Classifications

    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • 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
    • 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)

Definitions

  • Cannabidiol exists as a crystalline solid at room temperature, which has a melting point of 151 degrees Fahrenheit (66 degrees Celsius). Crystalline cannabidiol lacks robust bioavailability, for example, because the human body is incapable of melting it.
  • the pharmaceutical EPIDIOLEX® contains cannabidiol dissolved in sesame seed oil to increase bioavailability.
  • Cannabidiol crystallization confounds vaporization in electronic cigarettes and vaporizers because
  • crystallization inhibits the flow of cannabidiol toward a heating element.
  • Prior art methods to inhibit the crystallization of cannabidiol for use in electronic cigarettes and vaporizers include the dissolution of cannabidiol in organic solvents such as propylene glycol and triglycerides. Organic solvents dilute the cannabidiol, however, and present unknown health risks. Improved cannabidiol formulations are therefore desirable.
  • compositions comprising liquid cannabidiol, which have either a freezing point or a glass-liquid transition temperature of less than the melting point of pure cannabidiol.
  • the freezing point or the glass-liquid transition temperature is less than either 70 degrees Fahrenheit or 21 degrees Celsius.
  • This patent document discloses that the melting point of cannabidiol can be lowered— or eliminated— by dissolving small amounts of specific solutes in liquid cannabidiol.
  • the melting point of cannabidiol can be reduced to less than 70 degrees Fahrenheit (or less than 21 degrees Celsius), for example, to provide concentrated cannabidiol compositions that are liquids at room temperature. This discovery allows novel products including concentrated cannabidiol vape oil.
  • compositions comprising (i) cannabidiol at a concentration of at least 70 percent and no greater than 99.5 percent by mass, and (ii) one or more solutes selected from terpenes, terpene alcohols, terpenoids, and terpene oxidation products at a combined concentration of at least 0.5 percent and no greater than 30 percent by mass, in which: the one or more solutes comprise a terpene and a terpene oxidation product; the terpene is humulene; the terpene oxidation product is either bicyclohumuladiol, tricyclohumuladiol, tricyclohumuladiol II, humulenol II, humulene epoxide I, humulene epoxide II, or humulene epoxide III; the composition comprises the humulene and the terpene oxidation product at a concentration of at least 70 percent and no greater
  • the terpene oxidation product is bicyclohumuladiol.
  • the terpene oxidation product is tricyclohumuladiol.
  • the terpene oxidation product is tricyclohumuladiol II.
  • the terpene oxidation product is humulenol II.
  • the terpene oxidation product is humulene epoxide I.
  • the terpene oxidation product is humulene epoxide II.
  • the terpene oxidation product is humulene epoxide III.
  • compositions comprising (i) cannabidiol at a concentration of at least 70 percent and no greater than 99.5 percent by mass, and (ii) one or more solutes selected from terpenes, terpene alcohols, terpenoids, and terpene oxidation products at a combined concentration of at least 0.5 percent and no greater than 30 percent by mass, wherein: the one or more solutes comprise a terpene and a terpene oxidation product; the terpene is beta- caryophyllene; the terpene oxidation product is caryophyllene oxide; the composition comprises the beta-caryophyllene and the caryophyllene oxide at a ratio of at least 1 : 10 and no greater than 10,000: 1 by mass; the cannabidiol is a liquid; the one or more solutes are dissolved in the cannabidiol; and either (i) the composition has a freezing point of less than 21 degrees
  • compositions comprising (i) cannabidiol at a concentration of at least 70 percent and no greater than 99.5 percent by mass, and (ii) one or more solutes selected from terpenes, terpene alcohols, terpenoids, and terpene oxidation products at a combined concentration of at least 0.5 percent and no greater than 30 percent by mass, wherein: the one or more solutes comprise a terpene and a terpene oxidation product; the terpene is alpha- bisabolol; the terpene oxidation product is either caryophyllene oxide or humulene epoxide II; the composition comprises the alpha-bisabolol and the terpene oxidation product at a ratio of at least 1 : 10 and no greater than 10,000: 1 by mass; the cannabidiol is a liquid; the one or more solutes are dissolved in the cannabidiol; and either (
  • compositions comprising (i) cannabidiol at a concentration of at least 50 percent and no greater than 99.5 percent by mass and (ii) one or more solutes selected from terpenes, terpene alcohols, and terpenoids at a combined concentration of at least 0.5 percent and no greater than 40 percent by mass, in which: the one or more solutes are dissolved in the cannabidiol; the composition has either a freezing point or a glass-liquid transition temperature; and the freezing point or the glass-liquid transition temperature is either (i) at least 50 degrees Fahrenheit less than the freezing point of pure cannabidiol or (ii) at least 27 degrees Celsius less than the freezing point of pure cannabidiol.
  • the composition comprises the cannabidiol at a concentration of at least 65 percent and no greater than 99.5 percent by mass, and the composition comprises the one or more solutes at a combined concentration of at least 0.5 percent and no greater than 35 percent by mass.
  • the composition comprises the cannabidiol at a concentration of at least 70 percent and no greater than 99.5 percent by mass, and the composition comprises the one or more solutes at a combined concentration of at least 0.5 percent and no greater than 30 percent by mass.
  • the composition comprises the cannabidiol at a concentration of at least 75 percent and no greater than 99.5 percent by mass, and the composition comprises the one or more solutes at a combined concentration of at least 0.5 percent and no greater than 25 percent by mass.
  • Formula XV does not depict stereochemistry, and“cannabichromene” encompasses both stereoisomers of Formula XV.
  • the composition has a freezing point; the composition lacks a glass- liquid transition temperature; and the freezing point is less than either 70 degrees Fahrenheit or 21 degrees Celsius.
  • the composition has a glass-liquid transition temperature; the composition lacks a freezing point; and the glass-liquid transition temperature is less than either 70 degrees Fahrenheit or 21 degrees Celsius.
  • the composition lacks crystals of cannabidiol.
  • the composition comprises cannabidiol at a concentration of at least 75 percent and no greater than 99 percent by mass.
  • the composition lacks tetrahydrocannabinol at a concentration greater than 0.3 percent by mass.
  • the composition comprises tetrahydrocannabinol at a concentration greater than 0.3 percent by mass; the tetrahydrocannabinol is dissolved in the cannabidiol; and the composition comprises the cannabidiol and the tetrahydrocannabinol at a ratio of at least 3: 1 and no greater than 200: 1 by mass.
  • the composition comprises (6a,S , ,10ai?)-6,6,9-trimethyl-3-pentyl- 6a, 7, 8, 10a-tetrahydro-6H -benzo[c]chromen- l -ol at a concentration of at least 0.05 percent and no greater than 5 percent by mass, in which the (6aV, 10aR )-6,6,9-trimethyl-3-pentyl-6a,7,8, 10a- tetrahydro-6H -benzo[c]chromen- l -ol is dissolved in the cannabidiol.
  • the composition comprises molecules having a boiling point of less than either 360 degrees Fahrenheit or 182 degrees Celsius at a combined concentration of at least 95 percent by mass.
  • the composition lacks propylene glycol, glycerol, triglycerides, phospholipids, fatty acids, and waxes at a combined concentration greater than 5 percent by mass.
  • the composition lacks propylene glycol.
  • the composition lacks triglycerides.
  • the composition lacks phospholipids.
  • the composition lacks waxes.
  • the composition is a liquid.
  • the composition has a viscosity, and the viscosity is less than 100 pascal-seconds at a temperature of either 70 degrees Fahrenheit or 21 degrees Celsius. In some specific embodiments, the viscosity is at least 50 millipascal-seconds and no greater than 50 pascal-seconds at a temperature of either 70 degrees Fahrenheit or 21 degrees Celsius.
  • the one or more solutes comprise one or more of alpha-bisabolol, alpha- phellandrene, alpha-pinene, alpha-terpinene, alpha-terpineol, beta-caryophyllene, beta-pinene, borneol, cadinene, camphene, camphor, caryophyllene oxide, citral, citron ellol, delta-3 -carene, eucalyptol, eugenol, gamma-terpinene, geraniol, guaiol, humulene, isopulegol, limonene, linalool, myrcene, nerol, nerolidol, ocimene, para-cymene, phytol, pulegone, terpineol, terpinolene, and valencene at a combined concentration of at least 0.5 percent and no greater than
  • the one or more solutes comprise one or more of alpha- bisabolol, beta-caryophyllene, guaiol, humulene, limonene, myrcene, and terpinolene at a combined concentration of at least 0.5 percent and no greater than 40 percent by mass.
  • the one or more solutes comprise alpha-bisabolol.
  • the one or more solutes comprise beta-caryophyllene.
  • the one or more solutes comprise caryophyllene oxide.
  • the one or more solutes comprise humulene.
  • the composition comprises cannabidiol at a concentration of at least 65 percent and no greater than 99 percent by mass; the composition lacks crystals of cannabidiol; the composition lacks tetrahydrocannabinol at a concentration greater than 0.3 percent by mass; the one or more solutes comprise one or more of alpha-bisabolol, beta-caryophyllene, guaiol, humulene, limonene, myrcene, and terpinolene at a combined concentration of at least 0.5 percent and no greater than 35 percent by mass; the composition comprises molecules having a boiling point lower than either 360 degrees Fahrenheit or 182 degrees Celsius at a combined concentration of at least 95 percent by mass; the composition lacks propylene glycol, glycerol, triglycerides, phospholipids, fatty acids, and waxes at a combined concentration of greater than
  • the composition comprises cannabidiol at a concentration of at least 65 percent and no greater than 99 percent by mass; the composition lacks crystals of cannabidiol; the composition comprises tetrahydrocannabinol at a concentration of greater than 0.3 percent by mass; the tetrahydrocannabinol is dissolved in the cannabidiol; the composition comprises cannabidiol and tetrahydrocannabinol at a ratio of at least 3 : 1 and no greater than 200: 1 by mass; the one or more solutes comprise one or more of alpha-bisabolol, beta-caryophyllene, guaiol, humulene, limonene, myrcene, and terpinolene at a combined concentration of at least 0.5 percent and no greater than 35 percent by mass; the composition comprises molecules having a boiling point lower than either 360 degrees Fahrenheit or 182 degrees Celsius at a combined concentration of at least 95 percent by
  • the composition comprises cannabichromene at a concentration of at least 0.1 percent and no greater than 10 percent by mass. In some specific embodiments, the composition comprises cannabichromene at a concentration of at least 0.81 percent and no greater than 8.1 percent by mass. In some very specific embodiments, the composition comprises cannabichromene at a concentration of at least 1.94 percent and no greater than 6.92 percent by mass.
  • the combination of cannabichromene and one or more solutes selected from terpenes, terpene alcohols, terpenoids, and terpene oxidation products is more effective at reducing the freezing point of liquid cannabidiol than the one or more solutes alone.
  • the composition comprises cannabigerol at a concentration of at least 0.1 percent and no greater than 10 percent by mass. In some specific embodiments, the
  • composition comprises cannabigerol at a concentration of at least 0.81 percent and no greater than 8.1 percent by mass. In some very specific embodiments, the composition comprises cannabigerol at a concentration of at least 1.94 percent and no greater than 6.92 percent by mass.
  • a method to manufacture a cannabidiol product comprising (i) providing a starting composition comprising liquid cannabidiol; and (ii) dissolving one or more terpenes, terpene alcohols, terpenoids, or terpene oxidation products in the liquid cannabidiol to produce a composition described anywhere in this patent document.
  • a container comprising (i) a heating element and (ii) a chamber that contains at least 2 milligrams and no greater than 2 grams of a composition described anywhere in this patent document, wherein the heating element is in thermal
  • the container is configured to be connected to a battery such that the battery and the heating element are in electrical communication that allows the transfer of electrical energy from the battery to the heating element; the heating element is operable to convert the electrical energy into sufficient heat energy; and the sufficient heat energy is sufficient to heat the composition to a temperature greater than the boiling point of the cannabidiol.
  • the container is connected to the battery such that the battery and the heating element are in electrical communication.
  • a method to manufacture a cannabidiol product comprising (i) providing a composition comprising cannabidiol and one or more solutes, wherein the cannabidiol is a liquid, and the one or more solutes are dissolved in the cannabidiol; (ii) providing a starting container comprising a heating element; and (iii) inserting at least 2 milligrams and no greater than 2 grams of the composition into the starting container to produce a container described anywhere in this patent document.
  • a method to manufacture a cannabidiol product comprising (i) providing a starting composition comprising liquid cannabidiol; (ii) dissolving one or more terpenes, terpene alcohols, terpenoids, or terpene oxidation products in the liquid cannabidiol to produce a composition described anywhere in this patent document; (iii) providing a starting container comprising a heating element; and (iv) inserting at least 2 milligrams and no greater than 2 grams of the composition into the starting container to produce a container described anywhere in this patent document.
  • Cannabinoids were extracted from organic industrial hemp using the system described in PCT Patent Application Publication No. 2016/161420 A1 to produce crude industrial hemp extract comprising 65-70% cannabidiol; 5-10% terpenes, terpene alcohols, and terpenoids; 2-3% tetrahydrocannabinol; and other volatile molecules including waxes and phospholipids.
  • the crude industrial hemp extract formed crystals of cannabidiol when stored at room temperature for 24 hours.
  • the cannabinoids of the crude industrial hemp extract were separated from other molecules by distillation in a VTA Short Path Distillation Plant VKL 70 (Verfahrenstechnische Anlagen GmbH & Co. KG, Germany) to produce a cannabinoid distillate comprising approximately 90% cannabidiol and 5% tetrahydrocannabinol. 10 grams of the cannabinoid distillate was combined with 0.1 grams of a terpene, terpene alcohol, and terpenoid blend obtained from True Terpenes (Oregon, USA) with heating to produce a liquid composition.
  • the blend contained beta- caryophyllene (41%), humulene (18%), linalool (13%), limonene, alpha-bisabolol, nerolidol, beta- pinene, citronellol, fenchol, and other molecules at lower concentrations.
  • the liquid composition was stored at room temperature for 1 year with intermittent exposure to light and air, and the composition produced no detectable crystals. Cooling the liquid below room temperature vitrified the composition into a glass without any detectable crystal formation.

Abstract

Divers aspects de l'invention concernent des compositions (i) qui comprennent du cannabidiol, qui ont soit un point de congélation soit une température de transition vitreuse-liquide inférieure au point de fusion de cannabidiol pur, (ii) des contenants qui contiennent de telles compositions, et (iii) des procédés de fabrication de produits de cannabidiol.
PCT/US2020/029745 2019-04-26 2020-04-24 Compositions comprenant des formes non cristallines de cannabidiol WO2020219829A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3137559A CA3137559A1 (fr) 2019-04-26 2020-04-24 Compositions comprenant des formes non cristallines de cannabidiol

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
US201962839564P 2019-04-26 2019-04-26
US62/839,564 2019-04-26
US201962845231P 2019-05-08 2019-05-08
US62/845,231 2019-05-08
US16/408,428 2019-05-09
US16/408,428 US10993928B2 (en) 2019-04-26 2019-05-09 Compositions comprising non-crystalline forms of cannabidiol
US201962860224P 2019-06-11 2019-06-11
US62/860,224 2019-06-11
US201962942442P 2019-12-02 2019-12-02
US62/942,442 2019-12-02

Publications (1)

Publication Number Publication Date
WO2020219829A1 true WO2020219829A1 (fr) 2020-10-29

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PCT/US2020/029745 WO2020219829A1 (fr) 2019-04-26 2020-04-24 Compositions comprenant des formes non cristallines de cannabidiol

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WO (1) WO2020219829A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9085724B2 (en) * 2010-09-17 2015-07-21 Lubri3ol Oilfield Chemistry LLC Environmentally friendly base fluids and methods for making and using same
WO2016030369A1 (fr) * 2014-08-25 2016-03-03 Janing Holding Aps Dispositif avec des compositions pour administration aux poumons, à la muqueuse buccale et au cerveau
WO2017158539A1 (fr) * 2016-03-16 2017-09-21 Buzzelet Development And Technologies Ltd Composition de cannabinoïdes enrichie en terpène
US20180362741A1 (en) * 2015-07-30 2018-12-20 Sumitomo Rubber Industries, Ltd. Rubber composition
US20190091198A1 (en) * 2016-03-28 2019-03-28 Lihi BAR-LEV SCHLEIDER Cannabionid and cannabis-based compositions and methods for the treatment of inflammatory conditions of the gastrointestinal tract

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9085724B2 (en) * 2010-09-17 2015-07-21 Lubri3ol Oilfield Chemistry LLC Environmentally friendly base fluids and methods for making and using same
WO2016030369A1 (fr) * 2014-08-25 2016-03-03 Janing Holding Aps Dispositif avec des compositions pour administration aux poumons, à la muqueuse buccale et au cerveau
US20180362741A1 (en) * 2015-07-30 2018-12-20 Sumitomo Rubber Industries, Ltd. Rubber composition
WO2017158539A1 (fr) * 2016-03-16 2017-09-21 Buzzelet Development And Technologies Ltd Composition de cannabinoïdes enrichie en terpène
US20190091198A1 (en) * 2016-03-28 2019-03-28 Lihi BAR-LEV SCHLEIDER Cannabionid and cannabis-based compositions and methods for the treatment of inflammatory conditions of the gastrointestinal tract

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Publication number Publication date
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