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WO2019100007A1 - Compositions de cannabinoïdes - Google Patents

Compositions de cannabinoïdes Download PDF

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Publication number
WO2019100007A1
WO2019100007A1 PCT/US2018/061833 US2018061833W WO2019100007A1 WO 2019100007 A1 WO2019100007 A1 WO 2019100007A1 US 2018061833 W US2018061833 W US 2018061833W WO 2019100007 A1 WO2019100007 A1 WO 2019100007A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
formulation
phospholipids
approximately
weight
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.)
Ceased
Application number
PCT/US2018/061833
Other languages
English (en)
Inventor
Caleb Joshua Eades
Orion LEKOS
Giri CHEEKATI
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.)
Tilray Brands Inc
Original Assignee
Tilray Inc
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
Application filed by Tilray Inc filed Critical Tilray Inc
Priority to CA3119786A priority Critical patent/CA3119786A1/fr
Publication of WO2019100007A1 publication Critical patent/WO2019100007A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61K31/33—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
    • 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
    • A61K31/045—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
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays

Definitions

  • the active ingredients of cannabis in the form of cannabinoids— a diverse chemical family of compounds that act on cannabinoid receptors in cells and alter neurotransmitter release in the brain— can be useful in the practice of medicine.
  • cannabinoids a diverse chemical family of compounds that act on cannabinoid receptors in cells and alter neurotransmitter release in the brain— can be useful in the practice of medicine.
  • consumption of delta-9-tetrahydrocannabinol A9-THC, also referred to herein as“THC”
  • THC delta-9-tetrahydrocannabinol
  • Cannabis may be administered in a number of ways, including by smoking, vaporizing, by application of transdermal patches, and by consuming edible foods or products containing cannabis.
  • Edible forms of cannabis are considered discreet and effective options for receiving the medicinal effects of cannabis without exposure to the potentially harmful risks of cannabis smoke.
  • the onset timing of the drug effects of cannabis may be markedly different depending on how it is administered. For example, there is a delayed onset of the drug effects when cannabis is ingested as compared to when cannabis extract is smoked.
  • consumers do not appreciate the longer time needed to experience drug effects when consuming cannabis in edible form, they may consume more than an intended amount of the drug, which can result in adverse effects.
  • the time of onset of the drug may be controlled.
  • the present inventions describe methods of preparation and chemistry compositions that allow greater control over drug effect onset time.
  • compositions for administering cannabinoid It is an object of the present invention to provide improved compositions for administering cannabinoid. It is also an object of the present invention to control the onset timing of cannabis drug effects by including in the compositions, for example, phospholipids and waxes.
  • FIG. 1 depicts the chemical structure of cannabidiol
  • FIG. 2 depicts the chemical structure of delta-9-tetrahydrocannabinol
  • FIG. 3 depicts the chemical structure of phosphatidylcholine.
  • edible forms of cannabinoids are introduced through the gastrointestinal tract. Once in the gastrointestinal tract, the gut breaks down the edible form. The process of breaking down the edible form influences the time it takes for D9- THC to be absorbed into the bloodstream. Depending on the chemistry of the edible form, the drug can either quickly absorb into the bloodstream or take a long time to be digested and absorbed into the bloodstream.
  • the A9-THC travels via the portal vein to the liver, where it undergoes first-pass metabolism.
  • Liver enzymes primarily the cytochrome P450 system
  • l l-hydroxytetrahydrocannabinol l l-OH- THC
  • l l-OH- THC l l-hydroxytetrahydrocannabinol
  • Ratio-specific phospholipids and waxes may be used to control the onset timing of cannabis drug effects.
  • Phospholipids such as Phosphatidylcholine (PC) and Phosphatidylethanolamine (PH) may encapsulate the cannabinoid in a liposomal structure and quickly pass across the cell wall of the gut into the bloodstream. Phospholipids may thereby help to advance the onset timing of drug effects.
  • PC Phosphatidylcholine
  • PH Phosphatidylethanolamine
  • Cannabinoids may be solubilized with phospholipids in a solvent, such as ethanol, or with a lipid or terpene solution.
  • a solvent such as ethanol
  • Phosphatidylethanolamines may be synthesized by the addition of cytidine diphosphate-ethanolamine to diglycerides, releasing cytidine monophosphate.
  • S- Adenosyl methionine can subsequently methylate the amine of
  • the ratio of PC to PH may also influences the time to onset of drug effects.
  • the ratio of PC to PH may be, for example, between the ranges of 60% PC to 40% PH and 100% PC to 0% PH.
  • a phospholipid that is 90% to 100% PC has been found to provide an onset of cannabinoid drug effects in approximately five to 20 minutes.
  • a ratio of 75% PC and 25% PH provides an onset of cannabinoid drug effects in approximately 30 to 40 minutes.
  • Waxes such as beeswax
  • Waxes delay onset timing by binding the cannabinoids. Waxes are broken down slowly in the gut and do not release the cannabinoids until the wax is digested.
  • a beeswax with medium chain triglyceride (MCT) oil can delay onset of drug effects by up to four hours.
  • MCT medium chain triglyceride
  • Various methods of assessing time of onset were used to determine the effects of phospholipids and waxes.
  • One method used to assess the impact on time of onset included measuring change in heart rate. On average, as onset of drug effects occurs, the heart rate increases by 20 beats per minute. Also, eye dilation and mood shifts were further used to detect onset of the drug effects.
  • the present invention is further illustrated, but not limited, with reference to the following examples.
  • the formulations may include the oil nutrient D-limonene, a natural compound found in lemon and orange peels.
  • the amount of D-Limonene included may be, for example, less than 10% by weight of the formulation.
  • a terpene or terpene blend can be used in place of D-Limonene.
  • Polyoxyl 40 hydrogenated castor oil is sometimes used as a non-ionic oil- in-water solubilizer and/or emulsifying agent. It is almost tasteless, particularly suitable for fat-soluble vitamins, and is widely used in self-emulsifying drug delivery systems or microemulsifying systems.
  • Polyethylene glycol 300 (PEG-300) is a clear, colorless liquid made from sugar cane waste is soluble in water.
  • Example Formulation 1 may take the form of an oral spray.
  • Phospholipids PC and PH may comprise 10% to 20% of the formulation by weight, with PC comprising greater than 75% of the mix between PC and PH.
  • D-limonene may comprise less than 5% of the formulation
  • Polyoxyl 40 Hydrogenated Castor Oil may comprise 10% to 20% of the formulation
  • MCT Oil may comprises 10% to 20% of the formulation
  • THC may comprise less than 3% of the formulation.
  • the balance of the formulation may comprise PEG-300.
  • An example embodiment of Example Formulation 1 is set forth below in Table 1.
  • THC When 5mg of THC is ingested as part of Formulation 1, it may take approximately 20 minutes before onset of the drug effects. The peak may be felt in one hour, and the duration may be approximately three hours.
  • Example Formulation 2 may be a solid at room temperature, and may have a consistency appropriate for a capsule.
  • Phospholipids PC and PH may comprise 15% to 25% of the formulation by weight, with PC comprising greater than 80% of the mix between PC and PH.
  • D-limonene may comprise 5% to 10% of the formulation, and THC may comprise less than 3% of the formulation.
  • the balance of the formulation may comprise Polyoxyl 40 Hydrogenated Castor Oil.
  • An example embodiment of Example Formulation 2 is set forth below in Table 2. Table 2
  • THC capsule When a 5 mg THC capsule is ingested as part of Formulation 2, it may take approximately 15 minutes before onset of the drug effects, with a peak effect at approximately 45 minutes. The duration may be approximately three hours.
  • Example Formulation 3 may be a solid at room temperature, and may have a consistency appropriate for a capsule.
  • Phospholipids PC and PH may comprise 15% to 25% of the formulation by weight, with PC comprising greater than 65% to 85% of the mix between PC and PH.
  • D-limonene may comprise 5% to 10% of the formulation, and THC may comprise less than 3% of the formulation.
  • the balance of the formulation may comprise Polyoxyl 40 Hydrogenated Castor Oil.
  • An example embodiment of Example Formulation 3 is set forth below in Table 3.
  • Example Formulation 4 may have the consistency of ground sugar. It can be added to any baked good, drink, or other edible product. Phospholipid PC may comprise 5% to 15% of the formulation by weight. Ethanol and THC may each comprise less than 3% of the formulation. Corn syrup may comprise 20% to 30% of the formulation. The balance of the formulation may comprise cane sugar.
  • An example embodiment of Example Formulation 4 is set forth below in Table 4.
  • Example Formulation 4 may take approximately five to ten minutes for the onset of drug effects, and may last approximately 2 hours.
  • Example Formulation 5 may be a solid at room temperature, and may have a consistency appropriate for a capsule. Beeswax may comprise 5% to 15% of the formulation by weight, and THC may comprise less than 3% of the formulation. The balance of the formulation may comprise MCT Oil.
  • An example embodiment of Example Formulation 5 is set forth below in Table 5.
  • THC 1.0% When a 5 mg THC capsule formed according to Example Formulation 5 is ingested, onset of the drug effects may not occur for approximately four hours, and no obvious peak may be felt. The duration may be approximately 6 hours. This timing would be suitable for a sustained release.
  • Example Formulation 6 may take the form of a hard chewy, fruit jelly or a peppermint patty.
  • a lecithin emulsifier enriched with PC and/or PH may comprise 5% to 10% of the formulation by weight.
  • An emulsifier is PhospholiponTM, manufactured by the American Lechtin Company.
  • Lecithins are fatty substances occurring in animal and plant tissues. Lecithins are both hydrophilic and lipophilic, and are used for smoothing food textures, emulsifying, homogenizing liquid mixtures, and repelling sticking materials.
  • the lecithin may be enriched with phospholipids comprising 50% PC and 50% PH.
  • the lecithin may be enriched with phospholipids comprising 85% PC and 15% PH.
  • Vitamin E may comprise 5% to 10% of the formulation by weight
  • Lemon Oil may comprise up to 1% of the formulation by weight
  • Ethanol may comprise 5% to 10% of the formulation by weight.
  • the balance of the formulation may comprise Glycerin.
  • Cannabidiol (CBD), a naturally occurring cannabinoid, may be added to the formulation.
  • CBD cannabidiol
  • FIG. 1 depicts the chemical structure of CBD
  • FIG. 2 depicts the chemical structure of THC.
  • one mole of lecithin emulsifier, and as high as 20 or 25 moles of lecithin emulsifier, may be included for each mole of included cannabinoids.
  • An example embodiment of Example Formulation 6 is set forth below in Table 6. Table 6
  • Example Formulation 7 may take the form of a gel- like formulation which may be used in a gel capsule or a gel-like edible.
  • a lecithin emulsifier enriched with PC and/or PH may comprise up to 50% of the formulation by weight.
  • the mix of phospholipids may be at least 50% PC and 50% PH.
  • the mix of phospholipids may be at least 85% PC and 15% PH.
  • Lemon Oil may comprise up to 3% of the formulation by weight.
  • the balance of the formulation may comprise Polyoxyl 40 Hydrogenated Castor Oil.
  • THC and/or CBD may be added to the formulation. For example, lOmg of THC may be included.
  • Example Formulation 7 is set forth below in Table 7.
  • Example Formulation 8 may take the form of a cannabis-infused sugar.
  • a lecithin emulsifier enriched with PC and/or PH may comprise 5% to 15% of the formulation by weight.
  • the mix of phospholipids may be at least 50% PC and the remainder PH.
  • the mix of phospholipids may be 85% PC and 15% PH.
  • Corn syrup may comprise up to 25% of the formulation by weight.
  • the balance of the formulation may comprise Sugar.
  • THC and/or CBD may be added to the formulation. For example, lOmg of THC may be included.
  • An example embodiment of Example Formulation 8 is set forth below in Table 8.
  • Example Formulation 9 may take the form of a powder.
  • the powder may be added to a liquid for consumption.
  • the formulation may comprise 15 to 25 grams or 1.7% to 3% by weight of lecithin emulsifier enriched with PC and/or PH.
  • the mix of phospholipids may be at least 50% PC and the remainder PH.
  • the mix of phospholipids may be 85% PC and 15% PH.
  • Formulation 9 may further comprise 15 to 25 grams or 1.7% to 3% by weight of Vitamin E TPGS, 75 to 150 grams or 8.7% to 17.4% by weight of Ethanol, 400 to 500 grams or 46% to 58.1% of cane sugar, 150 to 200 grams or 17% to 24% by weight of corn syrup, up to 100 grams or up to 12% by weight of water, and 15 to 25 grams or 1.7% to 3% by weight of THC.
  • An example embodiment of Example Formulation 9 is set forth below in Table 9.
  • Example Formulation 10 may take the form of a water-soluble mix.
  • a lecithin emulsifier enriched with PC and/or PH such as PhospholiponTM, may comprise 20% to 30% of the formulation by weight.
  • the lecithin may be enriched with phospholipids comprising 50% PC and 50% PH.
  • the lecithin may be enriched with phospholipids comprising 85% PC and 15% PH.
  • Vitamin E may comprise 20% to 30% of the formulation by weight
  • Polysorbate 80 may comprise up to 15% of the formulation by weight
  • a cannabinoid e.g., THC and/or Cannabidiol (CBD)
  • CBD Cannabidiol
  • the balance of the formulation may comprise Ethanol.
  • An example embodiment of Example Formulation 10 is set forth below in Table 10.

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Abstract

L'invention concerne des compositions pour l'administration de cannabinoïdes, y compris des formes comestibles de cannabinoïdes. Les phospholipides et les cires peuvent être utilisés pour contrôler le moment de l'apparition des effets de médicament de cannabis.
PCT/US2018/061833 2017-11-17 2018-11-19 Compositions de cannabinoïdes Ceased WO2019100007A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3119786A CA3119786A1 (fr) 2017-11-17 2018-11-19 Compositions de cannabinoides

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201762558059P 2017-11-17 2017-11-17
US62/558,059 2017-11-17
US201862654815P 2018-04-09 2018-04-09
US62/654,815 2018-09-04

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WO2019100007A1 true WO2019100007A1 (fr) 2019-05-23

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020077103A1 (fr) * 2018-10-10 2020-04-16 Tilray, Inc. Procédés et formulations pour traiter la nausée et les vomissements induits par la chimiothérapie
WO2021026456A1 (fr) * 2019-08-07 2021-02-11 Orochem Technologies, Inc. Cannabinoïdes solubles dans l'eau
US11274320B2 (en) 2019-02-25 2022-03-15 Ginkgo Bioworks, Inc. Biosynthesis of cannabinoids and cannabinoid precursors
US12029720B2 (en) 2021-04-29 2024-07-09 Tilray Brands, Inc. Cannabidiol-dominant formulations, methods of manufacturing, and uses thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160184258A1 (en) * 2005-11-07 2016-06-30 Murty Pharmaceuticals, Inc. Oral gastrointestinal dosage form delivery system of cannabinoids and/or standardized marijuana extracts
US20170000744A1 (en) * 2015-03-10 2017-01-05 Nanosphere Health Sciences, Llc Lipid nanoparticle compositions and methods as carriers of cannabinoids in standardized precision-metered dosage forms
CA2952335A1 (fr) * 2015-12-19 2017-06-19 Delta 9 Gardening B.V. Formulations d'administration therapeutique et systemes renfermant des cannabinoides et des terpenes

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
US20160184258A1 (en) * 2005-11-07 2016-06-30 Murty Pharmaceuticals, Inc. Oral gastrointestinal dosage form delivery system of cannabinoids and/or standardized marijuana extracts
US20170000744A1 (en) * 2015-03-10 2017-01-05 Nanosphere Health Sciences, Llc Lipid nanoparticle compositions and methods as carriers of cannabinoids in standardized precision-metered dosage forms
CA2952335A1 (fr) * 2015-12-19 2017-06-19 Delta 9 Gardening B.V. Formulations d'administration therapeutique et systemes renfermant des cannabinoides et des terpenes

Non-Patent Citations (1)

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Title
SHRIVASTAVA: "A Review on Peppermint Oil", ASIAN JOURNAL OF PHARMACEUTICAL AND CLINICAL RESEARCH, vol. 2, no. 2, May 2009 (2009-05-01), pages 27 - 33, XP055611445, Retrieved from the Internet <URL:https://www.researchgate.net/publication/237842903_A_REVIEW_ON_PEPPERMINT_OIL> [retrieved on 20190227] *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020077103A1 (fr) * 2018-10-10 2020-04-16 Tilray, Inc. Procédés et formulations pour traiter la nausée et les vomissements induits par la chimiothérapie
US11274320B2 (en) 2019-02-25 2022-03-15 Ginkgo Bioworks, Inc. Biosynthesis of cannabinoids and cannabinoid precursors
WO2021026456A1 (fr) * 2019-08-07 2021-02-11 Orochem Technologies, Inc. Cannabinoïdes solubles dans l'eau
US12029720B2 (en) 2021-04-29 2024-07-09 Tilray Brands, Inc. Cannabidiol-dominant formulations, methods of manufacturing, and uses thereof

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