WO2019021005A1 - Composition pharmaceutique contenant un cannabinoïde - Google Patents

Composition pharmaceutique contenant un cannabinoïde Download PDF

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Publication number
WO2019021005A1
WO2019021005A1 PCT/GB2018/052109 GB2018052109W WO2019021005A1 WO 2019021005 A1 WO2019021005 A1 WO 2019021005A1 GB 2018052109 W GB2018052109 W GB 2018052109W WO 2019021005 A1 WO2019021005 A1 WO 2019021005A1
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Prior art keywords
pharmaceutical composition
weight
ppm
cannabinoid
component
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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/GB2018/052109
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English (en)
Inventor
Stuart Corr
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.)
Mexichem UK Ltd
Mexichem Fluor SA de CV
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Mexichem UK Ltd
Mexichem Fluor SA de CV
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Publication of WO2019021005A1 publication Critical patent/WO2019021005A1/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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/007—Pulmonary tract; Aromatherapy
    • A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
    • 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
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/12—Aerosols; Foams
    • A61K9/124—Aerosols; Foams characterised by the propellant

Definitions

  • the present invention relates to the administration of pharmaceutical formulations comprising one or more cannabinoids. More particularly, the present invention relates to inhalable pharmaceutical formulations comprising one or more cannabinoids and a propellant comprising 1,1-difluoroethane (HFA-152a) and lo the delivery of such formulations from a medication delivery device, such as an inhaler.
  • Cannabinoids are psychoactive compounds and are the main psychoactive component of cannabis.
  • the medicinal properties of cannabinoids have been known for many years including their use for treating or alleviating chronic pain, seizures, arthritis, nausea, neurodegenerative diseases, such as multiple sclerosis, cancer and HIV. They may also be effective as bronchodilators in the treatment of asthma and COPD.
  • Cannabinoids may be derived from natural sources or be synthetic or semi-synthetic in origin.
  • a typical source of cannabinoids is the plant cannabis sativa or hemp and extracts derived therefrom such as hemp oil.
  • Two particular cannabinoids of interest are delta-9- tetrahydrocannabinol (THC) and cannabidiol (CBD). It Is understood that the ratio of THC to CBD in any particular composition may be varied to minimise the psychotropic effects and optimise the therapeutic efficacy of the composition.
  • cannabinoids it is known to deliver cannabinoids to the lung by smoking cannabis, by vaporisation techniques involving heating the cannabis to vaporise the cannabinoids which can then be inhaled and by spraying. It is also known to deliver cannabinoids using inhaler devices, including metered dose inhalers ⁇ MDIs), in which the cannabinoids are delivered using a propellant.
  • the cannabinoid is combined with the liquefied propellant and stored in a pressurised container.
  • the container Is then coupled to a suitable delivery device that typically includes a mouthpiece, a nozzle and a valve assembly.
  • MDIs are a particularly well known type of inhalation drug delivery system and are well known to those skilled in the art. They are designed to deliver, on demand, a discrete and accurate amount of a drug to the respiratory tract of a patient using a liquefied propellant in which the drug is dissolved, suspended or dispersed. The design and operation of MDIs is described in many standard textbooks and in the patent literature.
  • nozzle and valve assembly that is capable of dispensing a controlled quantity of the drug through the nozzle when it is activated.
  • the nozzle and valve assembly are typically located in a housing that is equipped with a mouth piece.
  • a propellant If a propellant is to function satisfactorily in an inhaler device, it needs to have a number of properties. These include an appropriate boiling point and vapour pressure so that it can be liquefied in a closed container at room temperature but develop a high enough pressure when the inhaler is activated to deliver the drug as an atomised formulation even at low ambient temperatures. Further, the propellant should be of low acute and chronic toxicity and have a high cardiac sensitisation threshold. It should have a high degree of chemical stability in contact with the drug, the container and the metallic and non-metallic components of the inhaler device, and have a low propensity to extract low molecular weight substances from any etastomeric materials in the inhaler device.
  • the propellant should also be capable of maintaining the drug in a homogeneous solution, in a stable suspension or in a stable dispersion for a sufficient time to permit reproducible delivery of the drug in use.
  • the density of the iiquid propellant is desirably similar to that of the solid drug In order to avoid rapid sinking or floating of the drug particles in the Iiquid.
  • the propellant should not present a significant flammability risk to the patient in use. In particular, it should form a non-flammable or low flammability mixture when mixed with air in the respiratory tract.
  • Dichlorodifluoromethane (R-12) possesses a suitable combination of properties and was for many years the most widely used MDI propellant, often blended with trichlorofluoromethane (R-11 ). Due to international concern that fully and partially halogenated chlorofluorocarbons (CFCs), such as dichlorodifluoromethane and trichlorofluoromethane, were damaging the earth's protective ozone layer, many countries entered into an agreement, the Montreal Protocol, stipulating that their manufacture and use should be severely restricted and eventually phased out completely. Dichlorodifluoromethane and trichlorofluoromethane were phased out for refrigeration use in the 1990's, but are still used in small quantities in the MDI sector as a result of an essential use exemption in the Montreal Protocol.
  • CFCs chlorofluorocarbons
  • HFA-134a 1,1,1 ,2-tetrafluoroethane
  • R-12 1,1,1,2,3,3,3-heptafluoropropane
  • R-114 dfchlorotetrafluoroethane
  • HFA-134a and HFA-227ea have low ozone depletion potentials (ODPs), they have global warming potentials (GWPs), 1430 and 3220 respectively, which are now considered to be too high by some regulatory bodies, especially for dispersive uses when they are released into the atmosphere.
  • ODPs ozone depletion potentials
  • GWPs global warming potentials
  • HFA-134a One industrial area that has received particular attention recently has been the automotive air-conditioning sector where the use of HFA-134a has come under regulatory control as a result of the European Mobile Air Conditioning Directive (2006/40/EC).
  • GWP greenhouse warming potential
  • ODP low ozone depletion potential
  • Many of these alternatives include hydrofluoropropenes, especially the tetrafiuoropropenes, such as 2,3,3,3-tetrafluoropropene (HFO-1234yf) and 1,3,3,3- tetrafluoropropene (HFO-1234ze).
  • HFA-134a Although the proposed alternatives to HFA-134a have a low GWP, the toxtcological status of many of the components, such as certain of the fluoropropenes, is unclear and they are unlikely to be acceptable for use in the medical sector for many years, if at ail.
  • an inhalable pharmaceutical composition comprising a cannabinoid which can be delivered with an inhaler device such as MDI using a propeliant having a reduced GWP in comparison with HFA-134a and HFA-227ea.
  • a pharmaceutical composition e.g. a pharmaceutical suspension or a pharmaceutical solution, said composition comprising:
  • a drug component comprising at least one cannabinoid or a pharmaceutically acceptable derivative or salt thereof;
  • a propellant component comprising 1 , 1 -difluoroethane (HFA-152a).
  • the pharmaceutical composition of the first aspect of the invention may be delivered sublingualis but is preferably adapted for delivery to the respiratory tract and especially to the lungs.
  • the pharmaceutical composition is suitable for delivery to the respiratory tract using an inhaler device, such as a metered dose inhaler (MDI).
  • MDI metered dose inhaler
  • the pharmaceutical composition typically contains less than 500 ppm of water based on the total weight of the pharmaceutical composition.
  • the pharmaceutical composition contains less than 200 ppm, preferably less than 150 ppm, more preferably less than 50 ppm and particularly less than 20 ppm of water based on the total weight of the pharmaceutical composition.
  • the water content of the pharmaceutical composition we are referring to the content of free water in the composition and not any water that happens to be present in any hydrated drug compounds that may be used as part of the drug component.
  • the pharmaceutical composition is water-free.
  • the pharmaceutical composition of the first aspect may contain greater than 0.5 ppm of water, e.g. greater than 1 ppm, but less than the amounts discussed above, as it can in practice be difficult to remove all the water from the composition and then retain it in such a water-free state.
  • a pharmaceutical composition e.g. a pharmaceutical suspension or a pharmaceutical solution, said composition comprising:
  • a drug component comprising at least one cannabinoid or a pharmaceutically acceptable derivative or salt thereof;
  • a propellant component comprising 1 ,1 -difluoroethane (HFA-152a), wherein the composition contains less than 200 ppm, preferably less than 150 ppm, more preferably less than 50 ppm and especially less than 20 ppm of water based on the total weight of the pharmaceutical composition.
  • the pharmaceutical composition of the first aspect of the invention contains less than 1000 ppm, preferably less than 500 ppm, more preferably less than 100 ppm and particularly less than 50 ppm of dissolved oxygen based on the total weight of the pharmaceutical composition, in an especially preferred embodiment, the pharmaceutical composition is oxygen-free.
  • the pharmaceutical composition of the first aspect may contain greater than 0.5 ppm of oxygen, e.g.
  • a pharmaceutical composition e.g. a pharmaceutical suspension or a pharmaceutical solution, said composition comprising:
  • a drug component comprising at least one cannabinoid or a pharmaceutically acceptable derivative or salt thereof;
  • composition contains less than 1000 ppm, preferably less than 500 ppm, more preferably less than 100 ppm and especially less than 50 ppm of oxygen based on the total weight of the pharmaceutical composition.
  • cannabinoid as used herein encompasses naturally occurring as well as synthetic and semi-synthetic cannabinoids. Suitable naturally occurring cannabinoids Include those found in cannabis, such as the phytocannabinoids, e.g. the tetrahydrocannabinols (THC), cannabidiol (CBD) and cannabinol (CBN).
  • THC tetrahydrocannabinols
  • CBD cannabidiol
  • CBN cannabinol
  • Suitable synthetic cannabinoids include cannabinoids structurally related to tetrahydrocannabinol (THC), cannabimimetics and eicosanoids. More particular examples of synthetic cannabinoids for use in the present invention include nabilone, rimonabant, cannabicyclohexanol, JWB-018, JWH-073 and HU-210.
  • the drug component comprises at least one cannabinoid selected from the tetrahydrocannabinols (THC), preferably delta-9- tetrahydrocannabinol and delta-8-tetrahydrocannabinol, and cannabidiol (CBD).
  • THC tetrahydrocannabinol
  • CBD cannabidiol
  • the drug component consists essentially of at least one cannabinoid selected from the tetrahydrocannabinols (THC), preferably delta-9- tetrahydrocannabinol and delta-8 ⁇ tetrahydrocannabinol, and cannabidiol (CBD).
  • the drug component comprises or consists essentially of at least one tetrahydrocannabinol (THC).
  • the drug component comprises or consists essentially of cannabidiol (CBD).
  • CBD cannabidiol
  • the drug component comprises or consists essentially of at least one tetrahydrocannabinol (THC) and cannabidiol (CBD) in a THC: CBD weight ratio of between 0.4:0.6 to 0.6:0.4.
  • the drug component comprises or consists essentially of CBD containing less than 1% by weight of THC.
  • consists essentially of we mean that at least 98 weight %, more preferably at least ⁇ 9 weight % and especially at least 99.9 weight % of the drug component consists of the specified cannabinoid compound or compounds.
  • the pharmaceutical composition may be a solution, a suspension or a partial solution in which a proportion of the cannabinoid(s) is dissolved in the propellent, perhaps with the help of a co-solvent, with the remainder being undissolved and in suspension or at least capable of being placed in suspension after suitable agitation.
  • the amount of the drug component in the pharmaceutical composition of the first aspect of the present invention will typically be in the range of from 0.01 to 15.0 weight % based on the total weight of trie pharmaceutical composition.
  • the drug component will comprise from 0.01 to 10.0 weight %, more preferably from 0.05 to 5.0 weight % and especially from 0.05 to 3.0 weight % of the total weight of the pharmaceutical composition.
  • the drug component may consist essentially of or consist entirely of the at least one cannabinoid compound, derivative or salt. By the term "consists essentially of, we mean that at least 98 weight %, more preferably at least 99 weight % and especially at least 99.9 weight % of the drug component consists of the at least one cannabinoid compound.
  • the drug component may contain other drugs.
  • Suitable drugs for combining with the cannabinoid include corticosteroids, such as budesonide, mometasone, beclomethasone, fluticasone and the pharmaceutically acceptable derivatives thereof, such as the pharmaceutically acceptable salts and esters thereof; long acting muscarinic antagonists (LAMA), such as umeclldinlum, ipratropium, tiotropium, aclidinium as well as their pharmaceutically acceptable derivatives, such as their pharmaceutically acceptable salts, and the pharmaceutically acceptable salts of glycopyrrolate; short acting muscarinic antagonists (SAMA); long acting beta-2-agonists (LABA), such as formoterol, arformotero), bambuterol, clenbuterol, salmeterol, indacaterol, olodaterol, vilanterol and the pharmaceutically acceptable derivatives thereof, such as the pharmaceutically acceptable salts and esters thereof; and opioids, such as morphine or methadone.
  • corticosteroids
  • the propellent component in the pharmaceutical composition of the first aspect of the present invention comprises 1,1-difluoroethane (HFA-152a).
  • HFA-152a 1,1-difluoroethane
  • the propellant component' may additionally comprise one or more additional hydrofluorocarbon or hydrocarbon propellant compounds, e.g. selected from HFA-227ea, HFA-134a, difluoromethane (HFA-32), propane, butane, isobutane and dimethyl ether.
  • the preferred additional propellents are HFA-227ea and HFA-134a.
  • an additional propellant compound such as HFA-134a or HFA-227ea
  • at least 5 % by weight, preferably at least 10 % by weight and more preferably at least 50 % by weight of the propellant component should be HFA-152a.
  • the HFA-152a will constitute at least 90 weight %, e.g. from 90 to 99 weight %, of the propellant component.
  • the HFA-152a will constitute at least 95 weight %, e.g. from 95 to 99 weight %, and more preferably at least 99 weight % of the propellant component.
  • the propellant component consists entirely of HFA-152a so that the pharmaceutical composition of the invention comprises HFA-152a as the sole propellant.
  • the HFA-152a propellant will contain no more than 10 ppm, e.g. from 0.5 to 10 ppm, more preferably no more than 5 ppm, e,g. from 1 to 5 ppm, of unsaturated impurities, such as v!nyl fluoride, vinyl chloride, vinylidene fluoride and chloro-fluoro ethylene compounds.
  • the amount of propeilant component in the pharmaceutical composition of the Invention will vary depending on the amounts of the drugs and other components In the pharmaceutical composition.
  • the propeilant component will comprise from 65.0 to 99.9 weight % of the total weight of the pharmaceutical composition.
  • the propeilant component wilt comprise from 75.0 to 99.9 weight %, more preferably from 85.0 to 99.9 weight % and especially from 95.0 to 99.9 weight % of the total weight of the pharmaceutical composition.
  • the pharmaceutical composition of the first aspect of the present invention consists essentially of the two components (i) and (ii) listed above.
  • consists essentially of we mean that at least. 98 weight %, more preferably at least 99 weight % and especially at least 99.9 weight % of the pharmaceutical composition consists of the two listed components.
  • the pharmaceutical composition consists entirely of the two components (i) and (il).
  • the pharmaceutical composition of the first aspect of the present invention additionally includes a co-solvent or carrier solvent, such as a monohydric or polyhydric alcohol. Suitable polyhydric alcohols include the glycols, glycol ethers and glycerol.
  • C1.4 alkanols are preferred co-solvents, with ethanoi being especially preferred.
  • the inclusion of a co-solvent can serve to solubilise the drug in the propeilant and/or inhibit deposition of drug particles on the surfaces of the inhaler device that are contacted by the pharmaceutical composition as It passes from the container in which it is stored to the nozzle outlet.
  • Co-solvents can also be used to solubilise a surfactant, in the propeilant where one is used.
  • a co-solvent it will typically be present in an amount of from 0.5 to 30 % by weight, preferably in an amount of from 0.5 to 20 % by weight, and more preferably in an amount of from 1 to 10 % by weight based on the total weight of the pharmaceutical composition. Mixtures of co-solvents may also be used.
  • the pharmaceutical composition of the first aspect of the present invention may also include a surfactant component comprising at least one surfactant compound.
  • a surfactant component comprising at least one surfactant compound.
  • Surfactant compounds of the type that have been in use hitherto in pharmaceutical formulations for MDIs may be used in the pharmaceutical compositions of the present invention.
  • Preferred surfactants are selected from polyvinylpyrrolidone, polyethylene glycol surfactants, oleic acid and lecithin.
  • oleic acid we are not necessarily referring to pure (9Z)-octadec-9-enoic acid.
  • oleic acid When sold for surfactant use in medical applications, oleic acid is typically a mixture of several fatty acids, with (9Z)-octadec-9-enoic acid being the predominant fatty acid, e.g. present in an amount of at least 65 weight % based on the total weight of the surfactant. If a surfactant component is used, it will typically be present in an amount of from 0.1 to 2.5 % by weight, preferably in an amount of from 0.2 to 1.5 % by weight based on the total weight of the pharmaceutical composition.
  • the pharmaceutical composition further comprises a TAS2R taste receptor agonist, which may be naturally occurring or synthetic.
  • a TAS2R taste receptor agonist induces bronchodilation resulting in a reduction in the amount of coughing as the composition is administered. Accordingly, a composition with such an agonist can be more readily tolerated by the patient.
  • a TAS2R taste receptor agonist is included, it may be present in an amount of from 0.001 to 0.1 weight %, preferably in an amount of from 0.005 to 0.01 weight % based on the total weight of the pharmaceutical composition.
  • a particularly suitable TAS2R taste receptor agonist is saccharin. Mixtures of TAS2R taste receptor agonists may be used if desired.
  • the pharmaceutical composition further comprises a flavour component to mask the taste of the cannabinoid(s).
  • Suitable flavour compounds may be selected from peppermint oil, aniseed, chocolate, coco, menthol and vanillin.
  • the flavour component may be present in an amount of from 0.01 to 0.1 weight %, preferably in an amount of from 0.03 to 0.1 weight % based on the total weight of the pharmaceutical composition.
  • the flavour component may comprise a mixture of flavour compounds if desired.
  • compositions of the invention may also comprise one or more other additives of the type that are conventionally used in drug formulations for medication delivery devices, such as valve lubricants. Where other additives are included in the pharmaceutical compositions, they are normally used in amounts that are conventional In the art.
  • the pharmaceutical compositions of the invention find particular utility in the delivery of the drug component from a pressurised aerosol container, e.g. using a metered dose inhaler (MDI).
  • MDI metered dose inhaler
  • the pharmaceutical compositions are contained in the pressurised aerosol container and the HFA-152a propellant functions to deliver the drug component as a fine aerosol spray.
  • the pharmaceutical compositions of the invention are normally stored in a pressurised container or canister which is to be used in association with a medication delivery device. When so stored, the propellant component is normally in a liquid state.
  • the pressurised container is designed for use in a metered dose inhaler (MDI).
  • the pressurised container is a coated aluminium can or an uncoated aluminium can, especially the latter.
  • a second aspect of the present invention provides a pressurised container holding the pharmaceutical composition of the first aspect of the present invention.
  • the present invention provides a medication delivery device, especially a metered dose inhaler, having a pressurised container holding the pharmaceutical composition of the first aspect of the present invention.
  • the metered dose inhaler typically comprises a nozzle and valve assembly that is crimped to a container holding the pharmaceutical composition to be dispensed.
  • An elastomeric gasket is used to provide a seal between the container and the nozzle/valve assembly.
  • Preferred elastomeric gasket materials are EPDM, chlorobutyl, bromobutyl and cyclootefin copolymer rubbers as these can exhibit good compatibility with HFA-152a and also provide a good barrier to prevent or limit HFA-152a permeating from the container.
  • the pharmaceutical compositions of the present invention are for use in medicine for treating a patient suffering or likely to suffer from a medical condition. Accordingly, the present invention also provides a method for treating a patient suffering or likely to suffer from a medical disorder which comprises administering to the patient a therapeutically or prophyiactically effective amount of a pharmaceutical composition as discussed above.
  • the pharmaceutical composition is preferably delivered to the patient using a MDI.
  • the pharmaceutical compositions of the invention can be prepared and the MDI devices filled using techniques that are standard in the art, such as pressure filling and cold filling.
  • the pharmaceutical compositions can be prepared by a simple blending operation in which the at least one cannabinoid, the HFA-152a- containing propellent and any optional ingredients are mixed together in the required proportions in a suitable mixing vessel. Mixing can be promoted by stirring as is common in the art, Conveniently, the HFA-152a-contalning propellent is liquefied to aid mixing. If the pharmaceutical composition is made in a separate mixing vessel, it can then be transferred to pressurised containers for storage, such as pressurised containers that are used as part of medication delivery devices and especially MDIs.
  • compositions of the invention can also be prepared within the confines of a pressurised container, such as an aerosol canister or vial, from which the compositions are ultimately released as an aerosol spray using a medication delivery device, such as a MDI.
  • a weighed amount of the at least one cannabinoid, optionally dissolved or suspended in a co-solvent is introduced into the open container, A valve is then crimped onto the container and the HFA- 152a-containing propeliant component, in liquid form, introduced through the valve into the container under pressure, optionally after first evacuating the container through the valve.
  • Suitable containers may be made of plastics, metal, e.g. aluminium, or glass. Preferred containers are made of metal, especially aluminium which may be coated or uncoated. Uncoated aluminium containers are especially preferred.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dispersion Chemistry (AREA)
  • Otolaryngology (AREA)
  • Pulmonology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne une composition pharmaceutique. La composition comprend; (i) un composant de médicament comprenant au moins un cannabioïde ou un dérivé ou un sel pharmaceutiquement acceptable de celui-ci; et (li) un composant d'agent propulseur comprenant du 1,1-difiuoroethana (HFA -152 a).
PCT/GB2018/052109 2017-07-28 2018-07-26 Composition pharmaceutique contenant un cannabinoïde Ceased WO2019021005A1 (fr)

Applications Claiming Priority (2)

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GB1712159.1 2017-07-28
GBGB1712159.1A GB201712159D0 (en) 2017-07-28 2017-07-28 Pharmaceutical composition

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Cited By (8)

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WO2020249934A1 (fr) * 2019-06-11 2020-12-17 Mexichem Fluor S.A. De C.V. Procédé de chargement d'un récipient destiné à être utilisé avec un appareil d'administration de médicament, récipient pour un tel appareil et procédé de traitement d'un patient
GB2586477A (en) * 2019-08-20 2021-02-24 Mexichem Fluor Sa De Cv Composition and method
GB2588087A (en) * 2019-09-27 2021-04-21 Senzer Ltd Inhalable cannabinoid compositions and uses
CN114515280A (zh) * 2020-11-18 2022-05-20 云南汉盟制药有限公司 一种药物组合物及其应用
WO2023283592A1 (fr) * 2021-07-08 2023-01-12 484 Science Corp. Formulations pour le traitement de troubles respiratoires
WO2023172210A1 (fr) * 2022-03-08 2023-09-14 Prince Of Songkla University Inhalateurs de dose mesurée de cannabidiol pour la protection contre un antigène covid et d'autres allergènes
US11977085B1 (en) 2023-09-05 2024-05-07 Elan Ehrlich Date rape drug detection device and method of using same
WO2024182686A1 (fr) * 2023-03-02 2024-09-06 Kindeva Drug Delivery L.P. Inhalateurs doseurs et solutions comprenant des cannabinoïdes dans hfa-152a

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WO2012156711A1 (fr) * 2011-05-13 2012-11-22 Mexichem Amanco Holding S.A. De C.V. Compositions pharmaceutiques
WO2015121673A1 (fr) * 2014-02-14 2015-08-20 Kind Consumer Limited Compositions de cannabinoïdes et utilisations

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WO2006091922A1 (fr) * 2005-02-25 2006-08-31 Unimed Pharmaceuticals, Inc. Compositions de dronabinol et procedes d'utilisation de celles-ci
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WO2015121673A1 (fr) * 2014-02-14 2015-08-20 Kind Consumer Limited Compositions de cannabinoïdes et utilisations

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020249934A1 (fr) * 2019-06-11 2020-12-17 Mexichem Fluor S.A. De C.V. Procédé de chargement d'un récipient destiné à être utilisé avec un appareil d'administration de médicament, récipient pour un tel appareil et procédé de traitement d'un patient
CN113905720A (zh) * 2019-06-11 2022-01-07 墨西哥氟石股份公司 为与药物递送设备一起使用的容器装料的方法、用于这类设备的容器和用于治疗患者的方法
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CN114515280B (zh) * 2020-11-18 2023-08-11 云南汉盟制药有限公司 一种药物组合物及其应用
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WO2023172210A1 (fr) * 2022-03-08 2023-09-14 Prince Of Songkla University Inhalateurs de dose mesurée de cannabidiol pour la protection contre un antigène covid et d'autres allergènes
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