EP3658137A1 - Composition de cannabinoïdes présentant un profil d'acides gras de l'excipient optimisé - Google Patents

Composition de cannabinoïdes présentant un profil d'acides gras de l'excipient optimisé

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Publication number
EP3658137A1
EP3658137A1 EP18838855.7A EP18838855A EP3658137A1 EP 3658137 A1 EP3658137 A1 EP 3658137A1 EP 18838855 A EP18838855 A EP 18838855A EP 3658137 A1 EP3658137 A1 EP 3658137A1
Authority
EP
European Patent Office
Prior art keywords
acid
cannabinoid
composition
weight
oil
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.)
Withdrawn
Application number
EP18838855.7A
Other languages
German (de)
English (en)
Other versions
EP3658137A4 (fr
Inventor
Basil Adil SHAABAN
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.)
Individual
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Individual
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Publication date
Application filed by Individual filed Critical Individual
Priority claimed from PCT/US2018/044226 external-priority patent/WO2019023668A1/fr
Publication of EP3658137A1 publication Critical patent/EP3658137A1/fr
Publication of EP3658137A4 publication Critical patent/EP3658137A4/fr
Withdrawn legal-status Critical Current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
    • A61K31/045—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
    • 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)
    • 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
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • 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

Definitions

  • Oral medications are sometimes specially formulated to absorb directly through the oral mucosa and the oral dermal tissue.
  • Nasal sprays are also formulated to achieve rapid absorption and transmucosal delivery into the bloodstream.
  • Various other delivery modalities have been developed to improve delivery of bioactive compounds.
  • Human skin includes the epidermis, dermis and subcutis.
  • the epidermis includes the stratum corneum.
  • the stratum corneum is the outer layer of skin that protects the body. It is composed primarily of layers of dead, flattened keratinocytes surrounded by a phospholipid matrix. This can be visualized as brick and mortar wall and functions to provide a barrier to microbial parasites as well as environmental toxins.
  • the stratum corneum also presents a significant barrier to the delivery of transdermal drugs, vitamins, minerals, nutraceuticals and pharmaceuticals.
  • the stratum corneum varies in thickness in various parts of the body. In some regions a mucosal layer covers the skin, such as in the nasal, oral and other bodily cavities. It is commonly intended that bioactive compounds applied to the epidermis of the skin reach the blood vessels of the dermis, entering into general circulation.
  • Human mucosa includes outer epithelial layers, superficially keratinized or nonkeratinized, above a basal lamina that separates them from a deeper lamina intestinal whose papillary layer and capillary plexus contain the blood vessels bioactive compounds are often intended to diffuse into across the superficial mucosa, entering general circulation.
  • a formulation including bioactive compounds and a non-toxic excipient carrier that improves rate and efficiency of absorption, bioavailability and efficacy of the bioactive compounds.
  • a formulation having an extended shelf life.
  • the cannabinoid composition includes at least one essential oil selected from the group consisting of Anise, Basil, Bergamot, Cannabis, Cardamom, Chamomile, Cinnamon, Cocoa, Cypress, Eucalyptus, Fennel, Frankincense, Geranium, Ginger, Ginkgo Biloba, Gotu Kola, Grapefruit, Hemp, Jasmine, Lavender, Lavandin, Lemon, Lemon Verbena, Lemongrass, Lime, Marjoram, Neroli, Nutmeg, Orange, Oregano, Peppermint, Pepper, Pine, Ravintsara, Rose, Rosemary, Sage, Spearmint, Tea Tree, Thyme, Turmeric, Vanilla, Ylang Ylang, and any other therapeutic plant essential oils, and combinations thereof, including any of one or more of the monoterpenes, sequiterpenes and/or diterpenes, and/or their alcohols, and/or aldehydes and/or esters normally found in
  • the cannabinoid composition includes at least 0.1% by weight of at least one cannabinoid derived from Cannabis sativa L. It can be appreciated that the cannabinoid can be synthetic, derived from yeast, or other plant material.
  • the cannabinoid composition includes at least 5% by weight of palmitoleic acid.
  • the invention includes at least one additional fatty acid selected from the group consisting of oleic acid and palmitic acid.
  • the additional fatty acid is any omega-7 fatty acid having synergistic effects for cannabinoid delivery.
  • the additional fatty acid is palmitic acid, and the ratio of palmitic acid to the at least one cannabinoid is between 1: 100 to 1000: 1.
  • the delivery system includes Transdermal delivery administered in a manner selected from a dropper, spray, swab, patch, paste, cream, gel, lotion or ointment or other manner of transdermal delivery.
  • the cannabinoid composition in one embodiment, is whole plant cannabis sativa extract derived from hemp, marijuana, or combinations thereof.
  • Such extracts can be prepared using any of various extraction methods including methods that rely on CO 2 , ethanol, hydrocarbon, or combinations thereof. It can be appreciated that other method(s) or solvent(s) can be used for extraction with non-toxic methods preferable.
  • Cannabinoids include one or more of the following: Cannabidiol (CBD), Cannabidiolic Acid (CBDA), Cannabichromene (CBC), Tetrahydrocannabinol (THC), Tetrahydrocannabinolic Acid (THCA), Cannabigerol (CBG), Cannabidivarin (CBDV), Tetrahydrocannabivarin (THCV), or any other compound found exclusively or primarily in the Cannabis sativa L. plant, or any other compound that is a cannabinoid receptor (CB receptor) agonist, co- agonist, partial agonist, inverse agonist or antagonist in the human or animal organism.
  • CBD Cannabidiol
  • CBD Cannabidiolic Acid
  • CBC Cannabichromene
  • THC Tetrahydrocannabinol
  • THCA Tetrahydrocannabinolic Acid
  • CBD Cannabigerol
  • CBDV Cannabidivarin
  • THCV Tetra
  • Synthetic cannabinoids encompass a variety of distinct chemical classes: the classical cannabinoids structurally related to Tetrahydrocannabinol (THC), the non-classical cannabinoids (cannabimimetics) including the aminoalkylindoles, 1,5-diarylpyrazoles, quinolines, and arylsulfonamides, as well as eicosanoids related to endocannabinoids .
  • THC Tetrahydrocannabinol
  • cannabimimetics cannabimimetics
  • THC as used herein includes both acid and non-acid forms of this molecule, including isomers thereof.
  • Cannabidiol (CBD) is a major phytocannabinoid found in cannabis sativa and other plants.
  • compositions described herein can be infused with one or more additional bioactive compounds, other than cannabinoids, including botanical essential oil, preparations, and formulations thereof.
  • additional bioactive compounds other than cannabinoids, including botanical essential oil, preparations, and formulations thereof.
  • the compositions do not include cannabinoids, but instead rely on various non-cannabinoid bioactive compounds, such as essential oils for example.
  • Essential oils can be derived by steam-distillation, CO2 extraction or any other manner(s) from any one or more plants including, but not limited to, any species or subspecies of any of Anise, Basil, Bergamot, Cannabis, Cardamom, Chamomile, Cinnamon, Cocoa, Cypress, Eucalyptus, Fennel, Frankincense, Geranium, Ginger, Ginkgo Biloba, Gotu Kola, Grapefruit, Hemp, Jasmine, Lavender, Lavandin, Lemon, Lemon Verbena, Lemongrass, Lime, Marjoram, Neroli, Nutmeg, Orange, Oregano, Peppermint, Pepper, Pine, Ravintsara, Rose, Rosemary, Sage, Spearmint, Tea Tree, Thyme, Turmeric, Vanilla or Ylang Ylang.
  • the Bioactive compound(s) can be one or more of monoterpenes, sequiterpenes and/or diterpenes, and/or their alcohols, and/or aldehydes and/or esters which include, but are not limited to, any of alpha-Bisabolol, alpha-Caryophyllene (also known as Humulene), beta-Caryophyllene, Fenchone, Isobutyl Angelate, Guaiol, Limonene, Linalool, Myrcene, Neral, Nerolidol, Ocimene, alpha-Pinene, beta- Pinene, Terpineol, or Terpinolene, be they a) naturally-present in a botanical extract, or b) an isolate, or c) a synthetic version thereof, or d) a complex or mixture of two or more of any of (a), (b) and/or (c).
  • alpha-Bisabolol alpha-Caryo
  • the Bioactive compound includes at least one lipophilic pharmaceutical or nutraceutical compound, other than a cannabinoid.
  • various lipophilic nutraceutical compounds including cannabinoids are utilized.
  • THC, CBD and combinations thereof are utilized as the lipophilic nutraceutical compounds.
  • the bioactive compounds include one or more non-lipophilic pharmaceutical or nutraceutical compounds, other than cannabinoids. These non-lipophilic compounds are modified to become soluble in oil by chemical reactions, preferably non-toxic ones, by mixing with at least one lipophilic compound, by emulsification, or by any other process.
  • FIG. 1 is a THC molecule (tra «s-A 9 -tetrahydrocannabinol).
  • FIG. 2 is a CBD molecule (cannabidiol).
  • FIG. 3 is an Oleic acid molecule ((9 )-Octadec-9-enoic acid) having a chemical formula C 18 H 34 O 2 .
  • FIG. 4 is a Palmitic acid molecule (Hexadecanoic acid) having a chemical formula C 16 H 32 O 2 .
  • FIG. 5 is a Palmitoleic acid molecule ((9 )-Hexadec-9-enoic acid) having a chemical formula C 16 H 30 O 2 .
  • the present invention includes a composition of matter including a cannabinoid and excipient.
  • FIG. 1 and FIG. 2 show THC and CBD molecules, respectively.
  • cannabinoids derived from Cannabis sativa L. that can be substituted in accordance with the present invention.
  • FIG. 3 shows an Oleic acid molecule.
  • FIG. 4 shows a Palmitic acid molecule. Palmitic acid is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is ⁇ 3 ( ⁇ 2 ) 14 ⁇ , and its lipid numbers are C16:0. It is a major component of the oil from palm trees (palm oil).
  • the excipient, or carrier comprises between 5%-50% palmitoleic acid.
  • the concentration of palmitoleic acid is greater than 10%.
  • the palmitoleic acid content of the excipient or carrier is approximately 15%.
  • the cannabinoid content is preferably at least 1-15% of the composition.
  • the excipient is macadamia nut oil, in another embodiment, the excipient is sea buckthorn oil.
  • the excipient further includes oleic acid in a concentration of between 1% - 95% and palmitic acid content of l%-45% by weight. While the use of excipients composed of natural oils is expressed herein, similes and synthetic oils having similar fatty acid profiles can be employed in accordance with the present invention.
  • the excipient is Macadamia Nut Oil, or a simile thereof.
  • Table 1 Composition of tested Fatty Acids in three samples of Macadamia Nut Oil
  • the excipient is Sea Buckthorn Oil ⁇ Hippophaes rhamnoides).
  • An example of Sea Buckthorn Oil fatty acid composition is shown in Table 2. Table 2. Composition of fatty acids in a sample of sea-buckthorn oil
  • Palmitic acid is considered to be highly polar, which is believed to enhance its capability to effectuate transdermal and transmucosal delivery of bioactive compounds including lipophilic cannabinoids.
  • Macadamia Nut Oil is also a preferred excipient being a natural plant oil known for stability and longevity compared with many other plant oils, particularly oxidation resistance, and normally remains liquid at refrigerator temperatures, allowing it and the compounds it carries to be further preserved in the cold while remaining in a rapidly-administrable liquid state.
  • Palmitic Acid is the most abundant fatty acid in human tissues overall. Oleic Acid is the most abundant fatty acid in human adipose tissue and the second-most abundant in human tissues overall. Palmitoleic acid is another common constituent of human adipose tissue. Macadamia Nut Oil contains one of the closest natural approximations to the human lipid profile found in the plant kingdom and remarkably yields improved transdermal and transmucosal performance over other plant oils.
  • Macadamia Nut Oil as an excipient for the delivery of cannabis oil, plant oils and other essential oils, is a highly- effective, nontoxic, non-invasive, rapid Enteral, Oral, Transmucosal and Transdermal delivery modality for humans. Rapid delivery results when applied sublingually, sublabially or bucally, via the oral mucosal membrane, so the bioactive component begins to be effective within less than 10 minutes, and preferably within two minutes. Subjective data indicates that initial bioactivity resulting from entry of bioactive cannabinoids into the blood stream occurs within 2-10 minutes of administration.
  • the present invention is useful for improved delivery system for human and animal therapeutics alike, with its rapid absorbability and the consequent rapid-acting potential for various bioactive compounds delivered by the invention being of great interest for a wide variety of therapeutic modalities.
  • the present invention includes a bioactive compound such as a whole plant extract of cannabis sativa in an excipient.
  • the excipient includes a fatty acid selected from the group consisting of oleic acid, palmitic acid, palmitoleic acid, and combinations thereof. Particular ratios of these fatty acids to the bioactive compound are optimal. In one embodiment, the desired ratio of these fatty acids is naturally available through the use of Macadamia Nut Oil as a sole excipient.
  • Palmitic Acid C 16 H 32 O 2 (16:0) fatty acid can be derived from any source including naturally occurring, extracted, fractionated, isolated, or synthesized.
  • Bioactive compound a biologically-active compound that exerts a modifying and/or modulating effect upon the human and/or animal organism in any form or modality whatsoever including, but not limited to, the physiological, the psychological, the metabolic, the subjective, the observable, or any other effect whether a Therapeutic Effect or not.
  • This term includes, but is not limited to, botanical extracts, distillations and isolates, nutritional supplements, dietary supplements, and pharmaceutical compounds.
  • Macadamia Nut Oil any form of the oil extracted from the seed of any species or subspecies of the Macadamia Tree including, but not limited to, any of Macadamia integrifolia, Macadamia ternifolia and/or Macadamia tetraphylla. This includes the oil in any state or form including, but not limited to, any of natural, cold-pressed, expeller- pressed, virgin, filtered, refined, ethoxylated and/or processed in any form.
  • Macadamia-Nut-Oil-simile any oil or oil blend, whether of a) a single natural origin, b) two or more natural origins, c) one or more fractionated and/or isolated fatty acid(s) and/or glyceride(s), d) one or more synthetic fatty acid(s) and/or glyceride(s), or e) any combination of two or more of (a), (b), (c), or (d); that is comprised at least of the fatty acids within the ranges (inclusive of the limits) as follows in Table 3:
  • Oral delivery relating to entry by the mouth cavity into the gastrointestinal tract of the human and/or animal organism(s).
  • Rapid Absorption Delivery System any oil or oil blend, whether of a) a single natural origin, b) two or more natural origins, c) one or more fractionated and/or isolated fatty acid(s) and/or glyceride(s), d) one or more synthetic fatty acid(s) and/or glyceride(s), or e) any combination of two or more of (a), (b), (c), or (d); that A) consists of 10% by weight or more of either one, or any mixture of both together, of Macadamia Nut Oil and/or Macadamia-Nut-Oil-simile, both as defined in the Definitions, and/or B) consists of 10% by weight or more of either one, or any mixture of both together, of Sea Buckthorn Oil and/or Sea- Buckthorn-Oil- simile, both as defined in the Definitions, and/or C) consists of 5% by weight or more of Palmitoleic Acid; into which is mixed
  • Sea Buckthorn Oil any form of the oil extracted from the pulp of the berry, or from the whole berry, from any species or subspecies of Sea Buckthorn including, but not limited to, any of Hippophae rhamnoides L. subsp. rhamnoides and Hippophae rhamnoides L. subsp. sinensis. This includes any mixture of the oil extracted from the pulp of the berries and the oil extracted from the seed of the berries, or either on its own. This also includes the oil in any state or form including, but not limited to, any of natural, cold-pressed, expeller-pressed, virgin, filtered, refined, ethoxylated and/or processed in any form.
  • Sea-Buckthorn-Oil-simile any oil or oil blend, whether of a) a single natural origin, b) two or more natural origins, c) one or more fractionated and/or isolated fatty acid(s) and/or glyceride(s), d) one or more synthetic fatty acid(s) and/or glyceride(s), or e) any combination of two or more of (a), (b), (c), or (d); that is comprised at least of the following fatty acids within the ranges (inclusive of the limits) in Table 4: Table 4.
  • Sea-Buckthorn-Oil-simile any oil or oil blend, whether of a) a single natural origin, b) two or more natural origins, c) one or more fractionated and/or isolated fatty acid(s) and/or glyceride(s), d) one or more synthetic fatty acid(s) and/or glyceride(s), or e) any combination of two or more of (a
  • Sublabial relating to the tissues and mucosa behind the lips of the human and/or animal organism(s).
  • Sublingual relating to the tissues and mucosa below the tongue of the human and/or animal organism(s).
  • Transdermal relating to the transport across any part of the skin or dermal membranes of the human and/or animal organism(s).
  • a tincture including 18% whole plant cannabis extract and 82% macadamia nut oil.
  • the cannabis extract has 70% cannabinoid content prior to blending. After blending, the tincture has 12% cannabinoid concentration.
  • the hemp flower extract has a 30% cannabinoid concentration prior to blending.
  • the tincture has a 15% cannabinoid concentration.
  • a tincture including a blend of pure isolated CBD in a concentration of 15% and 85% macadamia nut oil.
  • a tincture including a blend of pure isolated THC in a concentration of 15% and 85% macadamia nut oil.
  • a tincture including a blend of pure isolated CBC in a concentration of 10% in 90% macadamia nut oil.
  • the whole plant cannabis extract expressed in the examples above is derived from substrate cannabis plant material, primarily the flowers and leaves.
  • the cannabinoids are directly extracted using conventional extraction methods. While many conventional extraction methods yield between 5-80% cannabinoid content, the present invention encompasses both extracts and concentrates having a cannabinoid content approaching up to 100% cannabinoid content.
  • Classical cannabinoids expressed herein include all classes derived from cannabigerol-type (CBG) compounds and differ mainly in the way this precursor is cyclized.
  • the classical cannabinoids are derived from their respective 2-carboxylic acids (2-COOH) by decarboxylation (catalyzed by heat, light, or alkaline conditions).
  • the classical cannabinoids include the following:
  • THCA Tetrahydrocannabinolic acid
  • CBD CBD (Cannabidiol)
  • CBDA CBDA (Cannabidiolic Acid)
  • CBDV (Cannabidivarin)
  • isolated means a pharmaceutically prepared cannabinoid in a concentration of above 90%, which can then be combined with other cannabinoids in desired ratios.
  • the present invention can utilize desirable isolated cannabinoids to engineer, replace, or supplement, a whole plant cannabinoid extract.
  • the cannabinoid profile (i.e. ratio of cannabinoids) in the whole plant cannabinoid extract reflects roughly the ratio of cannabinoids in the substrate plant material that is extracted.
  • Whole plant cannabinoid extract does not imply that all parts of the plant including roots and stems are used to create the cannabinoid extract.
  • the whole plant cannabinoid extract is manufactured primarily from flowers and leaves of the cannabis sativa plant.
  • the excipient can be a broad variety of synthetic and naturally occurring fatty acids, including omega-7 fatty acids.
  • the composition of the present invention is bioactive and can be formulated as a nutraceutical or pharmaceutical composition. Further, “simile” means “analogue” and the terms are interchangeable. Additionally the compositions and formulations of the present invention can be utilized for human consumption as well as administration and consumption by animals including felines and canines.

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Abstract

L'invention concerne une composition de substances visant à améliorer l'administration de composés bioactifs, en particulier de cannabinoïdes, dans un organisme humain ou animal. L'invention améliore l'administration orale, transmuqueuse et transdermique d'un composé bioactif comprenant des cannabinoïdes grâce à l'utilisation d'un excipient présentant des proportions souhaitées d'acides gras. L'invention concerne, en particulier, un phytocannabinoïde lipophile tel que le THC ou le CBD, et un profil d'acides gras de l'excipient comprenant de l'acide palmitoléique et des acides gras choisis dans le groupe constitué de l'acide oléique et de l'acide palmitique, et des combinaisons de ceux-ci dans lesquelles ils sont présents selon des proportions optimales. L'huile de noix de macadamia est un excipient préféré présentant le profil lipidique souhaité. L'huile de noix de macadamia est une huile végétale non toxique, qui assure aux acides gras et aux cannabinoïdes une bonne résistance à l'oxydation, afin d'améliorer la durée de conservation du produit, et qui présente une température de fusion suffisamment basse pour rester liquide même à l'état réfrigéré afin d'améliorer encore la durée de conservation du produit sans passage de celui-ci de la phase liquide à la phase solide.
EP18838855.7A 2017-07-27 2018-07-27 Composition de cannabinoïdes présentant un profil d'acides gras de l'excipient optimisé Withdrawn EP3658137A4 (fr)

Applications Claiming Priority (2)

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US201762537738P 2017-07-27 2017-07-27
PCT/US2018/044226 WO2019023668A1 (fr) 2017-07-27 2018-07-27 Composition de cannabinoïdes présentant un profil d'acides gras de l'excipient optimisé

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EP3658137A4 EP3658137A4 (fr) 2020-06-03

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US9526752B1 (en) * 2015-02-12 2016-12-27 Gary Allen Lowe Composition of cannabinoids, odorous volatile compounds, and emu oil for topical application, and a method for cannabinoid transdermal delivery
BR102015024165A2 (pt) * 2015-09-18 2017-03-28 Prati Donaduzzi & Cia Ltda composição farmacêutica oral compreendendo canabinóide, processo para sua preparação e seu uso

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