WO2019217800A1 - Réduction en poudre d'extrait de cannabis à usage médical par l'intermédiaire d'une procédure de granulation par voie humide - Google Patents

Réduction en poudre d'extrait de cannabis à usage médical par l'intermédiaire d'une procédure de granulation par voie humide Download PDF

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Publication number
WO2019217800A1
WO2019217800A1 PCT/US2019/031693 US2019031693W WO2019217800A1 WO 2019217800 A1 WO2019217800 A1 WO 2019217800A1 US 2019031693 W US2019031693 W US 2019031693W WO 2019217800 A1 WO2019217800 A1 WO 2019217800A1
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WO
WIPO (PCT)
Prior art keywords
solvent
oil
carrier
cannabis
peg
Prior art date
Application number
PCT/US2019/031693
Other languages
English (en)
Inventor
Emilio QUARTA
Benjamin LILLIBRIDGE
Original Assignee
La'au Pono
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 La'au Pono filed Critical La'au Pono
Publication of WO2019217800A1 publication Critical patent/WO2019217800A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/40—Effervescence-generating compositions
    • 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
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • 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

Definitions

  • the granulation method provided herein is a wet granulation process.
  • Means for granulating that are suitable for use in the process described herein may be manual or automatic.
  • Means for manually granulating include simple tools, such as a mortar and pestle.
  • the process may also be scaled, automated, and thereby optimized for commercial production by using available equipment.
  • Suitable mechanized and/or automated means for granulating include, but are not limited to, motorized mortar & pestles, high shear granulators, low shear mixers, high shear mixers, fluid bed granulators, extruders/sphreonizers, continuous fluid bed granulators, spray driers, and the like.
  • cannabis oil may be decarboxylated.
  • the decarboxylation process converts THC-A (which is non-psychoactive and acidic) to delta-9 THC. It is important to take care in the decarboxylation process, as too short or too long
  • decarboxylation may result in undesired effects. Specifically, insufficient decarboxylation will not fully activate the psychoactive component in the oil. On the other hand, excessive decarboxylation can result in increased sedative effects, which can be undesirable.
  • next steps in the process depend on the intended final product.
  • the process will vary depending on whether the final product is an orally dissolving tablet, an effervescent tablet; or a capsule (standard, enteric, or otherwise).
  • a method for creating a completely decarboxylated cannabis product so the most amount of delta-9 THC is available for the patient.
  • Complete decarboxylation can be achieved by heating the plant material to about 125 °C for about 30 minutes.
  • cannabis oil can be obtained from plant material using any viable extraction method/solvent, such as supercritical C0 2 , ethanol, etc..
  • Food-grade solvents may be used when producing a product for oral consumption. If desired, traces of solvent may be removed by evaporation or other means. A common means of removing solvent via evaporation employs a vacuum oven. The final product can be tested to determine residual solvent percentage.
  • compositions produced by the process described herein may also comprise a binder.
  • Binders suitable for use in the compositions and dosage forms disclosed herein include, but are not limited to, corn starch, potato starch, or other starches, gelatin, natural and synthetic gums such as acacia, sodium alginate, alginic acid, other alginates, powdered tragacanth, guar gum, cellulose and its derivatives ( e.g ., ethyl cellulose, cellulose acetate, carboxymethyl cellulose calcium, sodium carboxymethyl cellulose), polyvinyl pyrrolidone, methyl cellulose, pre gelatinized starch, hydroxypropyl methyl cellulose, microcrystalline cellulose, and mixtures thereof.
  • compositions produced by the process described herein may also comprise a filler.
  • suitable fillers for use in the compositions and dosage forms disclosed herein include, but are not limited to, talc, calcium carbonate (e.g ., granules or powder),
  • microcrystalline cellulose powdered cellulose, dextrates, kaolin, mannitol, silicic acid, sorbitol, starch, pre-gelatinized starch, and mixtures thereof.
  • compositions described herein may comprise a disintegrant.
  • Disintegrants may be used in the compositions disclosed herein to provide tablets that disintegrate when exposed to an aqueous environment. Too much of a disintegrant may produce tablets which may disintegrate in the bottle. Too little may be insufficient for disintegration to occur and may thus alter the rate and extent of release of the active ingredient(s) from the dosage form. Thus, a sufficient amount of disintegrant that is neither too little nor too much to detrimentally alter the release of the active ingredient(s) may be used to form the dosage forms of the compounds disclosed herein. The amount of disintegrant used may vary based upon the type of formulation and mode of administration, and may be readily discernible to those of ordinary skill in the art.
  • Disintegrants that can be used to form pharmaceutical compositions and dosage forms of the invention include, but are not limited to, agar-agar, alginic acid, calcium carbonate, microcrystalline cellulose, croscarmellose sodium, crospovidone, polacrilin potassium, sodium starch glycolate, potato or tapioca starch, other starches, pre-gelatinized starch, other starches, clays, other algins, other celluloses, gums or mixtures thereof.
  • compositions disclosed herein may comprise a surfactant.
  • surfactants which can be used to form the compositions and dosage forms described herein include, but are not limited to, hydrophilic surfactants, lipophilic surfactants, and mixtures thereof. That is, a mixture of hydrophilic surfactants may be employed, a mixture of lipophilic surfactants may be employed, or a mixture of at least one hydrophilic surfactant and at least one lipophilic surfactant may be employed.
  • a suitable hydrophilic surfactant may generally have an HLB value of at least 10, while suitable lipophilic surfactants may generally have an HLB value of or less than about 10.
  • An empirical parameter used to characterize the relative hydrophilicity and hydrophobicity of non ionic amphiphilic compounds is the hydrophilic-lipophilic balance ("HLB" value).
  • HLB hydrophilic-lipophilic balance
  • Surfactants with lower HLB values are more lipophilic or hydrophobic, and have greater solubility in oils, while surfactants with higher HLB values are more hydrophilic, and have greater solubility in aqueous solutions.
  • Hydrophilic surfactants are generally considered to be those compounds having an HLB value greater than about 10, as well as anionic, cationic, or zwitterionic compounds for which the HLB scale is not generally applicable.
  • lipophilic (i.e., hydrophobic) surfactants are compounds having an HLB value equal to or less than about 10.
  • HLB value of a surfactant is merely a rough guide generally used to enable
  • Hydrophilic surfactants may be either ionic or non-ionic. Suitable ionic surfactants include, but are not limited to, alkylammonium salts; fusidic acid salts; fatty acid derivatives of amino acids, oligopeptides, and polypeptides; glyceride derivatives of amino acids,
  • oligopeptides, and polypeptides lecithins and hydrogenated lecithins; lysolecithins and hydrogenated lysolecithins; phospholipids and derivatives thereof; lysophospholipids and derivatives thereof; carnitine fatty acid ester salts; salts of alkylsulfates; fatty acid salts; sodium docusate; acylactylates; mono- and di-acetylated tartaric acid esters of mono- and di-glycerides; succinylated mono- and di-glycerides; citric acid esters of mono- and di-glycerides; and mixtures thereof.
  • ionic surfactants include, by way of example:
  • lecithins lysolecithin, phospholipids, lysophospholipids and derivatives thereof; carnitine fatty acid ester salts; salts of alkylsulfates; fatty acid salts; sodium docusate; acylactylates; mono- and di-acetylated tartaric acid esters of mono- and di-glycerides; succinylated mono- and di glycerides; citric acid esters of mono- and di-glycerides; and mixtures thereof.
  • Ionic surfactants may be the ionized forms of lecithin, lysolecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylglycerol, phosphatidic acid, phosphatidylserine, lysophosphatidylcholine, lysophosphatidylethanolamine, lysophosphatidylglycerol,
  • lysophosphatidic acid lysophosphatidylserine, PEG-phosphatidylethanolamine, PVP- phosphatidylethanolamine, lactylic esters of fatty acids, stearoyl-2-lactylate, stearoyl lactylate, succinylated monoglycerides, mono/diacetylated tartaric acid esters of mono/diglycerides, citric acid esters of mono/diglycerides, cholylsarcosine, caproate, caprylate, caprate, laurate, myristate, palmitate, oleate, ricinoleate, linoleate, linolenate, stearate, lauryl sulfate, teracecyl sulfate, docusate, lauroyl carnitines, palmitoyl carnitines, myristoyl carnitines, and salts and mixtures thereof.
  • Hydrophilic non-ionic surfactants may include, but not limited to, alkylglucosides
  • hydrophilic-non-ionic surfactants include, without limitation, PEG-10 laurate, PEG- 12 laurate, PEG-20 laurate, PEG-32 laurate, PEG-32 dilaurate, PEG-12 oleate, PEG-15 oleate, PEG-20 oleate, PEG-20 dioleate, PEG-32 oleate, PEG-200 oleate, PEG-400 oleate, PEG-15 stearate, PEG-32 distearate, PEG-40 stearate, PEG-100 stearate, PEG-20 dilaurate, PEG-25 glyceryl trioleate, PEG-32 dioleate, PEG-20 glyceryl laurate, PEG-30 glyceryl laurate, PEG-20 glyceryl stearate, PEG-20 glyceryl oleate, PEG-30 glyceryl oleate, PEG-30 glyceryl ole
  • Suitable lipophilic surfactants include, by way of example only: fatty alcohols; glycerol fatty acid esters; acetylated glycerol fatty acid esters; lower alcohol fatty acids esters;
  • propylene glycol fatty acid esters sorbitan fatty acid esters; polyethylene glycol sorbitan fatty acid esters; sterols and sterol derivatives; polyoxyethylated sterols and sterol derivatives;
  • polyethylene glycol alkyl ethers polyethylene glycol alkyl ethers; sugar esters; sugar ethers; lactic acid derivatives of mono- and di-glycerides; hydrophobic transesterification products of a polyol with at least one member of the group consisting of glycerides, vegetable oils, hydrogenated vegetable oils, fatty acids and sterols; oil-soluble vitamins/vitamin derivatives; and mixtures thereof.
  • preferred lipophilic surfactants include glycerol fatty acid esters, propylene glycol fatty acid esters, and mixtures thereof, or are hydrophobic transesterification products of a polyol with at least one member of the group consisting of vegetable oils, hydrogenated vegetable oils, and triglycerides.
  • the composition can further comprise one or more pharmaceutically acceptable additives and excipients.
  • additives and excipients include, without limitation, detackifiers, anti-foaming agents, buffering agents, polymers, antioxidants, preservatives, chelating agents, viscomodulators, tonicifiers, flavorants, colorants, odorants, opacifiers, suspending agents, binders, fillers, plasticizers, lubricants, and mixtures thereof. Examples of specific additives and excipients are well known in the art.
  • Examples of natural coloring agents suitable for use in the compositions described herein include, but are not limited to, turmeric for yellow, purple sweet potato powder/red fruit juice powder for pink, and dehydrated grape powder for purple.
  • cannabis oil is heated to begin decarboxylation.
  • cannabis oil is heated at about 125 °C for about 30 minutes.
  • cannabis oil may be heated to about 90 °C for about 70 minutes;
  • heating at this lower temperature preserves volatile terpenes which may be found in the cannabis oil, if a product containing those compounds is desired.
  • a solvent such as ethanol, warmed to about 80 °C, is added to the oil in an amount equal to approximately 3X the amount of the oil (w/v).
  • the resulting oil/solvent mixture is mixed with a carrier.
  • the amount of the carrier is approximately equal to the amount of the solvent (w/v) and approximately 3X the amount of the oil (w/v).
  • the carrier/oil/solvent mixture is then subject to granulation. Once the granulation is complete, the mixture may be treated to remove the solvent. This treatment may include using heated drying means, such as a food dehydrator, vacuum oven, or the like; or non-heated means such as a freeze dryer or other lyophilizing means.
  • Example 1 Exemplary Process for preparing decarboxylated cannabis base
  • Main carrier powder mannitol, lactose, cyclodextrin, etc.
  • the final ratio of carriercannabis oikEtOH is about 1:0.3:1 (w/w/v) (g/g/mL), although all of the EtOH need not be used.
  • the weight of the powder may be assessed from time to time during the drying process to track the loss of water from the powder.
  • Weight loss of around 2 mg/hour indicates that the powder Is sufficiently dry.
  • Example 2 Orally Disintegrating Tablet (ODT) Comprising Decarboxyl ated Cannabis Base
  • the ODT requires several additional ingredients & excipients to make it a suitable delivery mechanism. Some of these are for manufacturing ease, some are for flavor, some are for functional benefit to increase dissolve time and enhance bio-availability, and some, such as other botanicals, are to create a synergistic effect with the cannabis medicine.
  • the percentages of each of the ingredients in the final weight of the powder mixture are as follows.
  • Carrier powder e.g ., mannitol, erythitol, cyclodextrin, lactose, etc.
  • Carrier powder e.g ., mannitol, erythitol, cyclodextrin, lactose, etc.
  • Binder ⁇ e.g., microcrystalline cellulose
  • Effervescent formula for increasing bioavailability. Effervescence has been shown to increase oral absorption of compounds, thus we have included it as part of the ODT formula. A 5:50 ratio of potassium bicarbonate to citric acid provides excellent results; however, there are many combinations of acids and bicarbonates to make this reaction occur. It is important to keep the total amount of effervescent formula below about 4%, as exceeding 4% may burn the user's tongue.
  • Gliding agent/Super disintegrant typically starches, these serve both as a glidant for the manufacturing of the product, as well as increasing disintegration time ⁇ e.g., corn, potato, or tapioca starch
  • anti-caking agent e.g., diatomaceous earth
  • lubricant e,g., magnesium stearate, l-leucine, etc.
  • Example 3 Effervescent Tablet Comprising Decarboxylated Cannabis Base
  • the effervescent tablet is the most complicated in terms of formula & manufacturing.
  • Sugar alcohol binder e.g. mannitol, lactose, erythitol
  • Cannabis-containing base powder 0-20%
  • Example 4 Capsule (standard, enteric, or otherwise) Comprising Decarboxylated Cannabis Base
  • Capsules require least amount of excipients as they are intended to target the Gl tract.
  • the amounts of excipients depend on the encapsulating technology.
  • Binders or flowability agents may be added as needed.
  • One exemplary formulation includes 0-5% binder and 0-2% flowability agent.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Nutrition Science (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
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Abstract

L'invention concerne des procédés de fabrication d'un produit à base de poudre d'extrait de cannabis décarboxylé par l'intermédiaire d'un nouveau procédé de granulation par voie humide. Lorsqu'ils sont décarboxylés, les ingrédients actifs sont plus facilement absorbés par voie sublinguale, buccale et/ou transmucosale, ce qui permet d'obtenir un produit supérieur présentant une biodisponibilité supérieure. Lorsqu'il est en poudre, l'extrait peut être administré de manière plus efficace et fiable qu'avec une forme d'extrait classique. Lorsqu'il est produit dans des comprimés à dissolution orale, l'extrait est absorbé par l'intermédiaire de récepteurs sublinguaux et évite le tractus gastro-intestinal, ce qui entraîne un début d'effet plus rapide et plus prévisible.
PCT/US2019/031693 2018-05-10 2019-05-10 Réduction en poudre d'extrait de cannabis à usage médical par l'intermédiaire d'une procédure de granulation par voie humide WO2019217800A1 (fr)

Applications Claiming Priority (2)

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US201862669497P 2018-05-10 2018-05-10
US62/669,497 2018-05-10

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WO2019217800A1 true WO2019217800A1 (fr) 2019-11-14

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060210694A1 (en) * 2005-03-18 2006-09-21 Chappell Rulon A Anti-caking agents and methods
US20080299190A1 (en) * 2005-01-18 2008-12-04 Novartis Ag Direct Compression Formulation and Process
WO2015065179A1 (fr) * 2013-10-29 2015-05-07 Echo Pharmaceuticals B.V. Pastille comprimée comprenant du cannabidiol, son procédé de fabrication, et utilisation d'une telle pastille pour le traitement oral de troubles de psychose ou d'anxiété
WO2016084075A1 (fr) * 2014-11-26 2016-06-02 One World Cannabis Ltd Utilisation synergique de cannabis pour le traitement d'un myélome multiple
US20160243177A1 (en) * 2015-02-24 2016-08-25 Ross M. Franklin Method For Conducing Concentrated Cannabis Oil To Be Stable, Emulsifiable And Flavorless For Use In Hot Beverages and Resulting Powderized Cannabis Oil
WO2018041686A1 (fr) * 2016-09-01 2018-03-08 Henkel Ag & Co. Kgaa Détergents contenant de la saponine

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080299190A1 (en) * 2005-01-18 2008-12-04 Novartis Ag Direct Compression Formulation and Process
US20060210694A1 (en) * 2005-03-18 2006-09-21 Chappell Rulon A Anti-caking agents and methods
WO2015065179A1 (fr) * 2013-10-29 2015-05-07 Echo Pharmaceuticals B.V. Pastille comprimée comprenant du cannabidiol, son procédé de fabrication, et utilisation d'une telle pastille pour le traitement oral de troubles de psychose ou d'anxiété
WO2016084075A1 (fr) * 2014-11-26 2016-06-02 One World Cannabis Ltd Utilisation synergique de cannabis pour le traitement d'un myélome multiple
US20160243177A1 (en) * 2015-02-24 2016-08-25 Ross M. Franklin Method For Conducing Concentrated Cannabis Oil To Be Stable, Emulsifiable And Flavorless For Use In Hot Beverages and Resulting Powderized Cannabis Oil
WO2018041686A1 (fr) * 2016-09-01 2018-03-08 Henkel Ag & Co. Kgaa Détergents contenant de la saponine

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"Decarboxylation", SKUNK PHARM RESEARCH, 7 March 2012 (2012-03-07), pages 1 - 6, XP055652657, Retrieved from the Internet <URL:https://skunkpharmresearch.com/decarboxylation> [retrieved on 20190616] *
GOLD, D: "Cannabis Alchemy", CANNABIS ALCHEMY, 5 July 2016 (2016-07-05), pages 1 - 99, XP055652653 *
NATTAPULWAT, N ET AL.: "Evaluation of Native and Carboxymethyl Yam (Dioscorea esculenta) Starches as Tablet Disintegrants", SILPAKORN UNIVERSITY SCIENCE & TECH JOURNAL, vol. 2, no. 2, 2008, pages 18 - 25, XP055652646 *

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