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WO2020150685A1 - Formulation d'aspirine micronisée - Google Patents

Formulation d'aspirine micronisée Download PDF

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Publication number
WO2020150685A1
WO2020150685A1 PCT/US2020/014218 US2020014218W WO2020150685A1 WO 2020150685 A1 WO2020150685 A1 WO 2020150685A1 US 2020014218 W US2020014218 W US 2020014218W WO 2020150685 A1 WO2020150685 A1 WO 2020150685A1
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WO
WIPO (PCT)
Prior art keywords
aspirin
amount
pharmaceutical composition
citrate salt
composition
Prior art date
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Ceased
Application number
PCT/US2020/014218
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English (en)
Inventor
Donald A. MILNE III
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Individual
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Individual
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Publication of WO2020150685A1 publication Critical patent/WO2020150685A1/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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1611—Inorganic compounds
    • 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
    • A61K31/60—Salicylic acid; Derivatives thereof
    • A61K31/612—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid
    • A61K31/616—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid by carboxylic acids, e.g. acetylsalicylic acid
    • 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
    • A61K47/02—Inorganic compounds
    • 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
    • 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
    • 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
    • A61K9/08—Solutions

Definitions

  • the present invention generally relates to rapid pain relief formulations of aspirin, and more particularly, micronized aspirin formulations with an ability for rapid uptake and relief.
  • the present application is directed to an aspirin formulation (i.e., pharmaceutical composition) that provides rapid therapeutic effects, such as pain relief or heart attack prevention or stabilization.
  • the aspirin formulation contains at least or solely the following components: (i) aspirin in an amount of 10-40 wt%; (ii) citrate salt (e.g., potassium citrate) in an amount of 60-90 wt%; and (iii) a sweetening agent in an amount of 1-10 wt%; wherein the wt% is by weight of the pharmaceutical composition, and the components (i)-(iii) are in a solid powdered
  • the pharmaceutical composition further includes up to 0.1 wt% of a pharmaceutically acceptable surfactant, such as sodium lauryl sulfate.
  • a pharmaceutically acceptable surfactant such as sodium lauryl sulfate.
  • the present application is directed to a method of preparing the pharmaceutical formulation described above.
  • the method generally includes: (i) micronization milling of a particulate mixture comprising aspirin and a citrate salt, and (ii) spray fluid bed granulation and drying of the micronized particulate mixture to result in a granulated (co-micronized) mixture comprising aspirin and citrate salt; wherein the aspirin is in an amount of 10-40 wt% (or 20-30 wt%) of the pharmaceutical composition and the citrate salt is in an amount of 60-90 wt% (or 60-80 wt%) of the pharmaceutical composition.
  • the method generally includes: (i) micronization milling of a particulate mixture comprising aspirin, citrate salt, and a sweetening agent to result in a micronized particulate mixture; and (ii) spray fluid bed granulation and drying of the micronized particulate mixture to result in a granulated mixture comprising aspirin, citrate salt, and sweetening agent; wherein the aspirin is in an amount of 10-40 wt% (or 20-30 wt%) of the pharmaceutical composition, the citrate salt is in an amount of 60-90 wt% (or 60-80 wt%) of the pharmaceutical composition, and the sweetening agent is in an amount of 1-10 wt% of the pharmaceutical composition.
  • the micronization milling is jet milling.
  • the spray fluid in step (ii) comprises a solution of a pharmaceutically acceptable surfactant.
  • the very rapid delivery of the aspirin formulation described herein is due at least in part to the highly micronized state of the aspirin and citrate salt, which results in very intimate contact (i.e., with enhanced surface area contact) between the aspirin and citrate salt.
  • the presence of both the aspirin and citrate salt in a micronized state enhances the bioavailability of the aspirin to result in a very rapid absorption, and in particular, a very rapid absorption from oral administration.
  • the term“rapid” or“very rapid,” as used herein, generally refers to a period of time of no more than or less than 1, 2, 5, or 10 minutes for the aspirin formulation to provide a therapeutic effect from the time of administration.
  • the invention is directed to a pharmaceutical composition containing at least: (i) aspirin in an amount of 10-40 wt%; (ii) citrate salt in an amount of 60-90 wt%; and (iii) a sweetening agent in an amount of 1-10 wt%; wherein the wt% is by weight of the pharmaceutical composition.
  • the components (i)-(iii) are in solid powdered (particulate) form, and more specifically, in a micronized state.
  • micronized generally refers to a particle size of no more than or less than 100 microns.
  • the micronized components e.g., micronized aspirin, citrate salt, and/or sweetening agent
  • the micronized components independently have a particle size of about 1, 2, 5, 7, 10, 12, 15, 18, 20, 30, 40, 50, 60, 70, 80, 90, or 100 microns, or a particle size independently within a range bounded by any two of the foregoing values.
  • the micronized components e.g., micronized aspirin, citrate salt, and/or sweetening agent
  • the micronized components independently have a particle size distribution characterized by a D 50 or D 90 of any of the foregoing values or ranges therein.
  • the aspirin may be included in the pharmaceutical composition in an amount of, for example, 10, 15, 20, 22, 25, 28, 30, 35, or 40 wt% or within a range bounded by any two of the foregoing values.
  • the citrate salt may be included in the pharmaceutical composition in an amount of, for example, 60, 62, 65, 68, 70, 72, 75, 78, 80, 85, or 90 wt% or within a range bounded by any two of the foregoing values.
  • the sweetening agent may be included in the pharmaceutical composition in an amount of, for example,
  • the citrate salt may be, for example, sodium citrate, potassium citrate, magnesium citrate, or calcium citrate.
  • the citrate salt may be a hydrate, such as sodium citrate (tri) dihydrate and potassium citrate (tri) monohydrate.
  • the sweetening agent can be any of the sweetening agents known in the art.
  • the sweetening agent is caloric, such as sucrose, glucose, or fructose.
  • the sweetening agent is reduced-caloric or non-caloric, such as aspartame, saccharin, sucralose, stevia, monk fruit extract, acesulfame K, sugar alcohol, or cyclamate.
  • the pharmaceutical composition is within a dosage form.
  • the dosage form can be selected from, for example, tablets, capsules, and liquid solutions and suspensions.
  • the dosage form includes the pharmaceutical composition, as described above, in granulated form.
  • the granules are agglomerated versions of the starting (micronized) powder; thus, the granules are significantly larger in size than particles of the starting powder.
  • the invention is directed to a method of preparing the pharmaceutical composition described above.
  • the method generally includes: (i) micronization milling of a particulate mixture containing aspirin, citrate salt, and optionally, sweetening agent, to result in a micronized particulate mixture containing at least the aspirin and citrate salt; and (ii) spray fluid bed granulations and drying of the micronized particulate mixture to result in a granulated mixture comprising at least the aspirin and citrate salt.
  • the aspirin, citrate salt, and optionally, sweetening agent are included in the wt% amounts provided above.
  • At least two of the components are separately micronized and then combined and integrally mixed to provide a micronized mixture of at least aspirin and citrate salt.
  • the integral mixing may or may not also involve micronization.
  • at least two of the components e.g., at least aspirin and citrate salt, and optionally, a sweetening agent
  • co-micronized i.e., micronized together
  • the latter embodiment co-micronization process
  • micronization milling Methods for micronization milling are well known in the art.
  • the micronization milling may be, for example, jet milling, bead milling, or mechanical milling.
  • Micronization milling methods are described in detail in, for example, J. Markarian, “Using Micronization to Reduce API Particle Size,” Pharmaceutical Technology,
  • Granulation is commonly employed in the production of solid dosage forms, and methods for granulating powders are well known in the art.
  • the granulation process results in agglomeration of the primary particles into granules that possess an improved flow, uniformity, and hardness properties.
  • the process of granulation is described for example, in C. Challener,“Granulation Method and Process Monitoring Matter,”
  • the pharmaceutical composition may include one or more additional pharmaceutically acceptable carriers and/or diluents well known in the art of pharmaceutical compositions.
  • the pharmaceutical compositions of the present invention are specially formulated for administration in solid or liquid form, for oral administration.
  • pharmaceutically acceptable is used herein to refer to those compounds, materials, compositions, and/or dosage forms that are, within the scope of sound medical judgment, suitable for entering a living organism, preferably without significant toxicity, irritation, or allergic response.
  • the carrier should also be compatible with other ingredients of the formulation.
  • the pharmaceutically acceptable carrier may be a liquid or solid filler, diluent, excipient, manufacturing aid (e.g., lubricant, talc magnesium, calcium or zinc stearate, or steric acid), or solvent encapsulating material, useful for introducing the active agent into the body.
  • suitable aqueous and non- aqueous carriers include, for example, water, ethanol, polyols (such as glycerol, propylene glycol, polyethylene glycol, and the like), vegetable oils (such as olive oil), and organic esters (such as ethyl oleate), and suitable mixtures thereof.
  • Proper fluidity can be maintained, for example, by the use of coating materials, such as lecithin, by the maintenance of the required particle size in the case of dispersions, and by the use of surfactants.
  • materials that can serve as pharmaceutically acceptable carriers include: (1) sugars, such as lactose, glucose and sucrose; (2) starches, such as com starch and potato starch; (3) cellulose, and its derivatives, such as sodium carboxymethyl cellulose, ethyl cellulose and cellulose acetate; (4) powdered tragacanth; (5) malt; (6) gelatin; (7) talc; (8) excipients, such as cocoa butter and waxes; (9) oils, such as peanut oil, cottonseed oil, safflower oil, sesame oil, olive oil, corn oil and soybean oil; (10) glycols, such as propylene glycol; (11) polyols, such as glycerin, sorbitol, mannitol and polyethylene glycol; (12) esters, such as ethyl oleate and ethyl laurate; (13) agar; (14) buffering agents, such as magnesium hydroxide and aluminum hydroxide
  • auxiliary agents such as wetting agents, emulsifiers, surfactants, lubricants (e.g., magnesium stearate), coloring agents, release agents, coating agents, sweetening agents, flavoring agents, preservative agents, and antioxidants can also be included in the pharmaceutical composition.
  • the pharmaceutical formulation includes an excipient selected from, for example, celluloses, liposomes, micelle-forming agents (e.g., bile acids), and polymeric carriers, e.g., polyesters and polyanhydrides.
  • Suspensions in addition to the active compounds, may contain suspending agents, such as, for example, ethoxylated isostearyl alcohols,
  • polyoxyethylene sorbitol and sorbitan esters polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar-agar and tragacanth, and mixtures thereof.
  • antibacterial and antifungal agents such as, for example, paraben,
  • antioxidants include: (1) water soluble antioxidants, such as ascorbic acid, cysteine hydrochloride, sodium bisulfate, sodium metabisulfite, sodium sulfite, and the like; (2) oil-soluble antioxidants, such as ascorbyl palmitate, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), lecithin, propyl gallate, alpha-tocopherol, and the like; and (3) metal chelating agents, such as citric acid, ethylenediamine tetraacetic acid (EDTA), sorbitol, tartaric acid, phosphoric acid, and the like.
  • water soluble antioxidants such as ascorbic acid, cysteine hydrochloride, sodium bisulfate, sodium metabisulfite, sodium sulfite, and the like
  • oil-soluble antioxidants such as ascorbyl palmitate, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT),
  • the surfactant which may be ionic or non-ionic, is typically included in an amount of up to 0.1 wt% of the pharmaceutical composition.
  • Pharmaceutically acceptable surfactants are described in detail in, for example, M. Mishra et ah,
  • pharmaceutically acceptable surfactants include e.g., sodium lauryl sulfate, the poloxamers, sorbitan monolaurate, sodium dioctylsulfosuccinate, gelatin, and lecithin.
  • Tablets may be produced by compression or molding, optionally with one or more auxiliary ingredients.
  • Compressed tablets may be prepared using binder (for example, gelatin or hydroxypropylmethyl cellulose), lubricant, inert diluent, preservative, disintegrant (for example, sodium starch glycolate or cross-linked sodium carboxymethyl cellulose), surface-active or dispersing agent.
  • the tablets, and other solid dosage forms of the active agent such as capsules, pills and granules, may optionally be scored or prepared with coatings and shells, such as enteric coatings and other coatings well known in the pharmaceutical arts.
  • the dosage form may include any of the features known in the art that aid in rapid release. In some embodiments, coatings and shells (or particularly, enteric coatings and shells) are excluded, since these may impede the desired rapid absorption.
  • the dosage form is required to be sterile.
  • the components and/or final dosage form may be sterilized by, for example, radiation exposure, filtration through a bacteria-retaining filter (for solutions), or by incorporating sterilizing agents in the form of sterile solid compositions.
  • the pharmaceutical compositions may also contain opacifying agents and may be of a composition that they release the active ingredient(s) only, or preferentially, in a certain portion of the gastrointestinal tract, optionally, in a delayed manner. Examples of embedding compositions that can be used include polymeric substances and waxes.
  • the active ingredient can also be in micro-encapsulated form, if appropriate, with one or more of the above-described excipients.
  • Liquid dosage forms are typically a pharmaceutically acceptable solution, emulsion, microemulsion, suspension, syrup, or elixir of the active agent.
  • the liquid dosage form may contain inert diluents, such as, for example, water or other solvents, solubilizing agents and emulsifiers, such as ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3 -butylene glycol, oils (in particular, cottonseed, groundnut, corn, germ, olive, castor and sesame oils), glycerol, tetrahydrofuryl alcohol, polyethylene glycols and fatty acid esters of sorbitan, and mixtures thereof.
  • inert diluents such as, for example, water or other solvents, solubilizing agents and emulsifiers, such as ethyl alcohol,
  • the pharmaceutical composition includes a biocompatible polymer, such as, for example, a polyamide, polycarbonate, polyalkylene, polymer of acrylic and methacrylic esters, polyvinyl polymer, polyglycolide, polysiloxane, polyurethane or and co-polymer thereof, cellulose, polypropylene, polyethylene, polystyrene, polymer of lactic acid and glycolic acid, polyanhydride, poly(ortho)ester, poly(butyric acid), poly(valeric acid), poly(lactide-co-caprolactone), polysaccharide, protein, polyhyaluronic acid, polycyanoacrylate, and blends, mixtures, and copolymers thereof.
  • a biocompatible polymer such as, for example, a polyamide, polycarbonate, polyalkylene, polymer of acrylic and methacrylic esters, polyvinyl polymer, polyglycolide, polysiloxane, polyurethane or and co-polymer thereof
  • the release characteristics of a formulation of the present invention depend on several factors, including, for example, the type and thickness of the encapsulating material, the concentration of encapsulated drug, and the presence of release modifiers.
  • the release can be manipulated to be pH dependent, such as by using a pH-sensitive coating that releases only at a low pH, as in the stomach, or releases at a higher pH, as in the intestine.
  • Release can also be manipulated by inclusion of salts or pore forming agents, which can increase water uptake or release of drug by diffusion from the capsule. Excipients that modify the solubility of the drug can also be used to control the release rate. Agents that enhance degradation of the matrix or release from the matrix can also be incorporated.
  • the agents can be added to the drug, added as a separate phase (i.e., as particulates), or can be co-dissolved in the polymer phase depending on the compound. Generally, the amount used is between 0.1 and thirty percent (w/w polymer).
  • Some types of degradation enhancers include inorganic salts, such as ammonium sulfate and ammonium chloride; organic acids, such as citric acid, benzoic acid, and ascorbic acid; inorganic bases, such as sodium carbonate, potassium carbonate, calcium carbonate, zinc carbonate, and zinc hydroxide; organic bases, such as protamine sulfate, spermine, choline, ethanolamine, diethanolamine, and triethanolamine; and surfactants.
  • inorganic salts such as ammonium sulfate and ammonium chloride
  • organic acids such as citric acid, benzoic acid, and ascorbic acid
  • inorganic bases such as sodium carbonate, potassium carbonate, calcium carbonate, zinc carbonate, and zinc hydroxide
  • organic bases such as protamine sulfate, spermine, choline, ethanolamine, diethanolamine, and triethanolamine
  • surfactants such as sodium carbonate, potassium carbonate, calcium carbonate, zinc carbonate, and zinc hydrox
  • the pharmaceutical composition includes solely
  • composition includes one, two, or more other components, such as any of the components described above.
  • pharmaceutical composition excludes one or more of any of the additional components described above.
  • the invention is directed to methods of using the aspirin formulation described above.
  • the aspirin formulation is designed to be administered orally, nasally (e.g., via a spray), or transdermally (i.e., via a patch placed on the skin) in a manner that provides rapid systemic absorption of the formulation (via the
  • a pharmaceutically effective amount of the aspirin formulation is administered to a person experiencing or at risk of an urgent condition (e.g., heart attack, migraine, or bodily pain) that can be ameliorated or prevented by rapid absorption of aspirin, as provided by the aspirin formulation described above.
  • the dosage may be, for example, 25, 50, 80, 100, 150, 200, 250, 300, 325, 350, 400, 450, 500, 600, 700, 800,
  • SPEED OF ABSORPTION evaluate if any Instaprin/aspirin is detectable in the blood stream in 3 minutes or less
  • MAXIMUM ABSORPTION Can the maximum absorption of Instaprin exceed 14 Mg/dl blood in less than one hour.
  • the purpose of this test is to demonstrate the speed of absorption and the saturation level of aspirin in the blood.
  • the clinical outcome (CO) is considered an unexpected success if there is any measurable absorption in less than 3 minutes.
  • the clinical outcome would also be considered a success if the maximum saturation exceeds 14 mg/dl blood at any time during the testing.
  • the test will be conducted using a FDA approved assay test that will be completed by BioTrial, LLC. an FDA certified testing facility. This is an in- house anecdotal study and not approved by the FDA, but the test procedures however are the same or similar as outlined by the planned FDA clinical study to be conducted by BioTrial once the IND (Investigational New Drug Application index) number is issued.
  • test design and procedure is simple and straight forward. Using a certified licensed Phlebotomist to witness the administration of the powdered aspirin and to properly and accurately retrieve a blood sample following the ingestion of the Instaprin powdered aspirin at preset intervals. The phlebotomist will then label the samples and mail the samples by express courier to the testing facility which will then test for aspirin levels in each sample.
  • the proper test protocol set by the FDA is a salicylate assay test and reported as salicylate levels measured in Mg/Dl blood.
  • the testing was conducted at the company headquarters in Merrick, NY.
  • the chain of custody of the product was simple: a GMP batch of the pharmaceutical formulation of the present disclosure was in storage at Glatt Air Techniques, an FDA certified
  • the product of the present disclosure was removed from its sealed packaging and a single dose of 4.2 grams was weighed using a standard medical scale. Two (2) ounces of water were put into a standard drinking glass. The 4.2 grams of the claimed formulation was placed in a medical cup next to the water glass.
  • the first blood sample would be a baseline to make sure the test subject was free and clear of any aspirin in his system.

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Abstract

La présente invention concerne une composition pharmaceutique comprenant: (I) de l'aspirine suivant une quantité de 10 à 40 % en poids; (ii) un sel de citrate suivant une quantité de 60 à 90 % en poids; (iii) un agent édulcorant suivant une quantité de 1 à 10 % en poids, et éventuellement, (iv) jusqu'à 0,1 % en poids d'un tensioactif pharmaceutiquement acceptable, les % en poids étant en poids de la composition pharmaceutique, et les composants (i)- (iii) étant dans un état micronisé. L'invention concerne également un procédé de préparation d'une composition pharmaceutique selon la revendication 1, le procédé comprenant: (I) le broyage par micronisation d'un mélange particulaire comprenant de l'aspirine, un sel de citrate, et facultativement, un agent édulcorant, pour produire un mélange particulaire micronisé; et (ii) la granulation en lit fluidisé et le séchage dudit mélange particulaire micronisé pour obtenir un mélange granulé comprenant de l'aspirine, un sel de citrate et, éventuellement, un agent édulcorant, dans les quantités fournies ci-dessus.
PCT/US2020/014218 2019-01-18 2020-01-18 Formulation d'aspirine micronisée Ceased WO2020150685A1 (fr)

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WO2024206885A1 (fr) * 2023-03-31 2024-10-03 Aspire Biopharma, Inc. Formulations mucosales orales d'aspirine

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US20240167531A1 (en) * 2019-11-14 2024-05-23 Siemens Gamesa Renewable Energy A/S Damper for a wind turbine
WO2024206885A1 (fr) * 2023-03-31 2024-10-03 Aspire Biopharma, Inc. Formulations mucosales orales d'aspirine

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