WO2008152398A2 - Formulations pour inhalation - Google Patents

Formulations pour inhalation Download PDF

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Publication number
WO2008152398A2
WO2008152398A2 PCT/GB2008/002029 GB2008002029W WO2008152398A2 WO 2008152398 A2 WO2008152398 A2 WO 2008152398A2 GB 2008002029 W GB2008002029 W GB 2008002029W WO 2008152398 A2 WO2008152398 A2 WO 2008152398A2
Authority
WO
WIPO (PCT)
Prior art keywords
formulation
formulation according
polymer
propellant
pvp
Prior art date
Application number
PCT/GB2008/002029
Other languages
English (en)
Other versions
WO2008152398A3 (fr
Inventor
Arnar Lulla
Geena Malhotra
Original Assignee
Cipla Limited
Curtis, Philip, Anthony
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 Cipla Limited, Curtis, Philip, Anthony filed Critical Cipla Limited
Publication of WO2008152398A2 publication Critical patent/WO2008152398A2/fr
Publication of WO2008152398A3 publication Critical patent/WO2008152398A3/fr

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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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0043—Nose

Definitions

  • the present invention relates to aerosol formulations suitable for pulmonary, nasal, buccal or topical administration, which have good stability. It also relates to process for manufacturing the same.
  • Drugs for treating respiratory disorders are frequently administered in oral aerosol formulations.
  • One widely used method for dispensing such an aerosol drug formulation involves making a formulation of the drug in a liquefied gas known as a propellant.
  • the drug may be dissolved or suspended in the propellant, or in a combination slurry-solution.
  • Chlorofluorocarbons have been used extensively as propellants in drug formulations that are delivered to patients via an MDI.
  • CFCs Chlorofluorocarbons
  • CFCs damage the Earth's ozone layer. It is believed that ozone blocks harmful ultraviolet rays and that depletion of the ozone layer will result in the incidence of skin cancer. As a result, steps have been taken to reduce CFC production and usage, and recent recommendations have been made that CFC production be virtually discontinued and alternate ozone free propellants should be used.
  • MDI formulations containing HFA propellants do not have suspension characteristics as good as those formulations containing CFC Propellants.
  • an MDI formulation containing the beta-agonist albuterol sulfate and an anticholinergic agent, such as ipratropium bromide or tiotropium, with an HFA propellant is not a stable suspension and either quickly sediments, floats or forms an emulsion.
  • U.S. Pat. No. 5,182,097 to Byron et al. relates to aerosol formulations consisting of 1,1,1,2- tetrafluoroethane, a drug and oleic acid as a surfactant to aid in dispersing the drug in the propellant.
  • surfactants may not be feasible for all drugs because of considerable difficulties have been encountered in finding suspending agents which are soluble in hydrofluoroalkanes and capable of stabilizing medicament suspensions.
  • surfactants other excipients are required, in which all drugs may not be stable.
  • It is an object of the present invention is to provide a pharmaceutical aerosol formulation with good stability.
  • Another object of the present invention is to provide a pharmaceutical aerosol formulation that overcomes the problem of sedimentation and stability of suspension.
  • Still another object of the present invention is to provide a process to manufacture the pharmaceutical formulation according to the present invention.
  • a pharmaceutical aerosol formulation comprising the drug coated with a polymer, which is advantageously polyvinylpyrrolidone ("PVP”), in combination with a propellant, optionally with other suitable excipients.
  • PVP polyvinylpyrrolidone
  • a pharmaceutical aerosol formulation wherein the concentration of the polymer, which is advantageously PVP, used to coat the drug is in the range of 0.00001% to 10% of the formulation.
  • the concentration of the polymer used to coat the drug is in the range of 0.00001% to 0.1% w/w, typically 0.0001% to 0.001% w/w of the formulation.
  • the concentration of the polymer is in the range of 0.0005% to 0.0035% w/w of the formulation (which corresponds to 0.3% to 2% w/w of the active).
  • the pharmaceutical aerosol formulation comprises the drug coated with the polymer, which is advantageously PVP, and one or more surfactants.
  • the pharmaceutical aerosol formulation according to the present invention may further comprise either other suitable excipients or similarly coated or uncoated drug particles.
  • polymers include polymers like PVP which when used to coat the drugs, yields good quality suspensions.
  • the concentration of the polymer, especially PVP, used for the coating is greater than or equal to 0.0005% w/w of the formulation (which corresponds to 0.3% w/w of the active), suspension quality is increased compared to concentrations below 0.0005% w/w.
  • the concentration of the polymer is greater than 0.0035% w/w of the formulation (which corresponds to 2% w/w of the active)
  • the formulation has a lower FPD (fine particle dose) and also results in greater valve-sticking, compared to formulations with a concentration of polymer less than or equal to 0.0035% w/w.
  • the present invention provides a pharmaceutical aerosol formulation having good stability. More specifically, the pharmaceutical aerosol formulation comprises a pharmaceutically active agent coated with a polymer in combination with a propellant and optionally other suitable excipients.
  • the invention is especially suitable for use with hydrofluoroalkane (“HFA”) propellants.
  • HFA hydrofluoroalkane
  • the polymer used may be PVP (polyvinylpyrrolidone), such as PVP Kl 7, PVP K25 or PVP K30 may be used.
  • the PVP can be present in a range of about 0.00001% to about 10% of the formulation.
  • the concentration of the PVP used to coat the drug is in the range of about 0.00001% to about 0.1% w/w, typically about 0.0001% to about 0.001% w/w of the formulation.
  • the PVP is preferably present in a range of about 0.0005% to about 0.0035% w/w of the formulation (0.3%-2% w/w of the active). More preferably, the PVP is present in the range of about 0.0005% to about 0.001% w/w of the formulation.
  • the PVP is present in a range of about 0.0006% w/w to about 0.001% w/w of the formulation (0.35% to 0.6% w/w of the active) and most preferably about 0.0007% w/w to about 0.00095% w/w by weight of the formulation. (0.4%- 0.55% w/w of the active).
  • the present invention provides a pharmaceutical aerosol formulation, having good stability, comprising a pharmaceutically active agent coated with PVP in combination with a propellant and optionally other suitable excipients.
  • the invention is especially suitable for use with hydrofluoroalkane (“HFA”) propellants.
  • HFA hydrofluoroalkane
  • the drug may also be coated with a surfactant.
  • the present invention therefore also provides a pharmaceutical aerosol formulation comprising a pharmaceutically active agent coated with a polymer and surfactant in combination with a propellant, preferably a hydrofluoroalkane (“HFA”) propellant, and optionally other suitable excipients.
  • a pharmaceutically active agent coated with a polymer and surfactant in combination with a propellant, preferably a hydrofluoroalkane (“HFA”) propellant, and optionally other suitable excipients.
  • a propellant preferably a hydrofluoroalkane (“HFA”) propellant
  • Suitable surfactants may comprise sorbitan trioleate, tweens, e.g., tween 20, 40, 60, 80,120, Lipids, lecithin, oleic acid, citric acid, and polyoxyethylene(4)lauryl ether (Brij 30®).
  • tweens e.g., tween 20, 40, 60, 80,120
  • Lipids Lipids, lecithin, oleic acid, citric acid, and polyoxyethylene(4)lauryl ether (Brij 30®).
  • the surfactant is tween 80.
  • the surfactant can be present in a range of about 0.00001-0.01% by weight of the active.
  • the solvent used for dissolving the PVP or the surfactant should be such that the selected drug is either insoluble or has a suitably low solubility in the selected solvent.
  • the present invention relates to a method for coating drug particles with a polymer, especially PVP.
  • This method is a general method for coating the drug particles.
  • a solution of the polymer, such as PVP, may be prepared in a solvent in which the selected drug is either practically insoluble in the solvent or has a solubility less than 0.01 to 0.1%.
  • the concentration of the polymer solution may vary with the selected drug but is typically in the range 0.0005 to 0.0035% by weight of the formulation (0.3%-2% w/w of the active).
  • the micronized drug powder may be added to the solution of polymer and mixed with techniques known in the art, e.g. sonicating or stirring, for about 30 min to give a homogeneous suspension.
  • Micronized drug powder is defined as comprising particles having a mean size in the range of 1 to 5 ⁇ m.
  • the drug particles will be coated with a layer of the polymer solution.
  • the coated particles may be separated from the suspension by techniques known in the art, e.g. spraying through a suitable spray drier, and dried.
  • the powder may be collected and deaggregated to produce a free flowing powder.
  • the powder may be subjected to conventional milling techniques to give appropriate size to the drug particles.
  • the appropriate quantity of the coated drug and propellant may then be admixed in a suitable container to give final suspension.
  • the present invention relates to a method for coating drug particles with a polymer, especially PVP, and one or more surfactants.
  • This method is a general method for coating the drug particles.
  • a solution of the polymer, such as PVP, and the surfactant may be prepared separately in a solvent in which the selected drug is either insoluble or has a suitably low solubility.
  • the concentration of the polymer and surfactant solution varies with the selected drug.
  • An appropriate quantity of the surfactant solution may be mixed with the solution of PVP and to this resultant solution is added the micronized drug powder and mixed with techniques known in the art, e.g. sonicating or stirring, for about 30 min to give a homogeneous suspension.
  • Micronized drug powder is defined as comprising particles having a mean size in the range of 1 to 5 ⁇ m.
  • the drug particles will be coated with a layer of above polymer and surfactant solution.
  • the coated particles may be separated from the suspension by techniques known in the art, e.g., spraying through a suitable spray drier and dried.
  • the powder may be collected and deaggregated to produce a free flowing powder.
  • the powder may be subjected to conventional milling techniques to give appropriate size to the drug particles.
  • the appropriate quantity of the coated drug and propellant may then be admixed in a suitable container to give final suspension.
  • coated drug particles produced by either of the two methods may further be mixed with other similarly coated or uncoated drugs and/or one or more suitable excipients selected from the group consisting of cosolvents, bulking agents, antioxidants, lubricants.
  • coated drug may be mixed with other similarly coated or uncoated drugs and optionally with surfactants.
  • the formulation may further comprise one or more cosolvents, such as polyethylene glycol ("PEG"), propylene glycol, isopropyl myristate or glycerol.
  • PEG polyethylene glycol
  • the cosolvent is PEG, such as PEG 200 or PEG 400.
  • the cosolvent can be present in a range of about 0.05% to about 15% by weight of the formulation.
  • the cosolvent is present in a range of about 0.05% to about 1% or about 0.05% to about 0.3% by weight of the formulation.
  • the formulation may further comprise one or more bulking agents, preferably selected from the class of saccharides, including but not limited to monosaccharides, disaccharides, polysaccharides and sugar alcohols such as arabinose, glucose, fructose, ribose, mannose, sucrose, trehalose, lactose, maltose, starches, dextran or mannitol.
  • the bulking agent may be present in a concentration of 10-500% w/w active, more preferably in a range of 10-300% w/w active.
  • the preferred bulking agent is lactose.
  • the present invention may optionally comprise antioxidants like citric acid, benzalkonium chloride.
  • HFA propellants are now preferred over CFC propellants.
  • suitable HFA propellants for use in the present invention include, but are not limited to, 1,1,1,2-tetrafluoroethane (HFA-134a) and 1,1,1,2,3,3,3-heptafluoropropane (HFA-227).
  • HFA-134a 1,1,1,2-tetrafluoroethane
  • HFA-227 1,1,1,2,3,3,3-heptafluoropropane
  • mixtures of two or more such halogen-substituted hydrocarbons may also be used.
  • the invention is particularly useful in that it allows acceptably stable dispersions to be attained using HFA Propellant as the aerosol propellant.
  • the formulations of the invention may be prepared with HFA Propellant alone or a mixture of HFA Propellant and another miscible adjuvant having a polarity equal to or lower than the polarity of the HFA Propellant.
  • Suitable solid medicaments may include antiallergics, analgesics, bronchodilators, antihistamines, thereapeutic proteins and peptides, antitussives, anginal preparations, antibiotics, antiinflammatory preparations, hormones, or sulfonamides, such as, for example, a vasoconstrictive amine, an enzyme, alkaloid, or steroid, and synergistic combinations of these.
  • medicaments which may be employed are: Isoproterenol [alpha- (isopropylaminomethyl) protocatechuyl alcohol], phenylephrine, phenylpropanolamine, glucagon, adrenochrome, trypsin, epinephrine, ephedrine, narcotine, codeine, atropine, heparin, morphine, dihydromorphinone, ergotamine, scopolamine, adrenaline, metaproterenol, phenylephrine, phenylpropanolamine, reproterol, isoetharine, tulobuterol, orciprenaline, or(-)-4-amino-3,5 -dichloro- a-[[[6-[2-(2- pyridinyl)ethoxy]hexyl]amino]methyl]benzenemethanol; diuretics, e.g.amiloride methapyr
  • antibiotics such as neomycin, streptomycin, penicillin, procaine penicillin, sulphonamides, pentamidine, tetracycline, chlorotetracycline and hydroxytetracycline; adrenocorticotropic hormone and adrenocortical hormones, such as cortisone, hydrocortisone, hydrocortisone acetate and prednisolone; insulin, antiallergy compounds such as cromolyn sodium, ketotifen ornedocromil etc. xanthines e.g. aminophylline, choline theophyllinate, lysine theophyllinate or theophylline; and therapeutic proteins and peptides, e.g. insulin or glucagons.
  • antibiotics such as neomycin, streptomycin, penicillin, procaine penicillin, sulphonamides, pentamidine, tetracycline, chlorotetracycline and
  • therapeutic agents mentioned above as well as the drugs throughout the specification are used in a broad sense to include not only various therapeutic agents and drugs per se but also their pharmaceutically acceptable salts, pharmaceutically acceptable solvates and pharmaceutically acceptable hydrates, pharmaceutically acceptable enantiomers, pharmaceutically acceptable derivatives, pharmaceutically acceptable polymorphs or pharmaceutically acceptable prodrugs thereof.
  • salts of the drugs mentioned above may be used; acetate, benzenesulphonate, benzoate, bicarbonate, bitartrate, bromide, calcium edetate, camsylate, carbonate, chloride, citrate, dihydrochloride, edetate, edisylate, estolate, esylate, fumarate, fluceptate, gluconate, glutamate, glycollylarsanilate, hexylresorcinate, hydrobromide, hydrochloride, hydroxynaphthoate, iodide, isethionate, lactate, lactobionate, malate, maleate, mandelate, mesylate, methylbromide, methylnitrate, methylsulphate, mucate, napsylate, nitrate, 1 pamoate (embonate), pantothenate, phosphate diphosphate, polygalacturonate, salicylate, stearate, suba
  • Cationic salts may also be used.
  • Suitable cationic salts include the alkali metals, e.g. sodium and potassium, and ammonium salts and salts of amines known in the art to be pharmaceutically acceptable, e.g. glycine, ethylene diamine, choline, diethanolamine, triethanolamine, octadecylamine, diethylamine, triethylamine, l-amino-2-propanol-amino-2- (hydroxymethyl)propane-l,3-diol and l-(3,4-dihydroxyphenyl)-2 isopropylaminoethanol.
  • Preferred drugs for use with the invention are betamimetics and anticholinergics.
  • betamimetics or “anticholinergic agent” are used in a broad sense to include not only the betamimetics or anticholinergic agent per se but also their pharmaceutically acceptable salts, pharmaceutically acceptable solvates and pharmaceutically acceptable hydrates, pharmaceutically acceptable enantiomers, pharmaceutically acceptable derivatives, pharmaceutically acceptable polymorphs or pharmaceutically acceptable prodrugs thereof
  • Betamimetic agents useful in the formulations of the present invention include, but are not limited to, albuterol, formoterol, levalbuterol, carmoterol, pirbuterol and salmeterol.
  • the international name for albuterol is salbutamol.
  • Suitable pharmaceutically acceptable salts of the betamimetics include, but are not limited to the hydrochloride, sulfate, maleate, tartrate, and citrate salts.
  • the betamimetic is albuterol or albuterol sulfate.
  • Anticholinergic agents useful in the formulations of the present invention include, but are not limited to, oxitropium, ipratropium and tiotropium.
  • Suitable pharmaceutically acceptable salts of the anticholinergic agents include, but are not limited to, the halide salts such as bromide, chloride and iodide.
  • the anticholinergic agent is ipratropium or ipratropium bromide or ipratropium bromide monohydrate.
  • the invention also provides, in another aspect, a metered dose inhaler (MDI) comprising (i) a housing containing a pharmaceutical composition as described above; and (ii) means enabling the application of the composition from within the housing by oral administration directly to the lungs.
  • MDI metered dose inhaler
  • Suitable coatings include, but are not limited to, fluorocarbon copolymers such as FEP-PES (fluorinated ethylene propylene and polyethersulphone) and PFA-PES (perfluoroalkoxyalkane and polyethersulphone), epoxy and ethylene.
  • the metering valve is suitably comprised of a butyl elastomer.
  • Metered dose inhalers are designed to deliver a fixed unit dosage of medicament per actuation or "puff.
  • Administration of medicament may be indicated for the treatment of mild, moderate or severe acute or chronic symptoms or for prophylactic treatment. It will be appreciated that the precise dose administered will depend on the age arid condition of the patient, the particular particulate medicament used and the frequency of administration and will ultimately be at the discretion of the attendant physician.
  • the formulation of the present invention may be administered one, two, three or four times per day with one or more activations, e.g. two, three or four activations, of the metering valve per administration to treat broncho- constriction, asthma and related disorders thereof.
  • Tween 80 50 mg is added in 100ml of alcohol and sonicated. 0.5% w/w (of active) of PVP Kl 7 is dissolved in about 250 ml of dried acetone and sonicated. To this solution is added about 0.02 ml of above prepared tween 80 solution. To this solution salbutamol sulphate is added and sonicated for about 30 min. This is then further spray dried to obtain coated salbutamol.
  • the percentage of polymer is expressed as w/w of active and the percentage of surfactant is also expressed as w/w of active.
  • Lactose was added to (a) (c) The canister was crimped with the metered valve and was charged with the propellant.
  • Lactose was added to (a) (c) The canister was crimped with the metered valve and was charged with the solution of propellant and PEG.
  • Lactose was added to (a) (c) The canister was crimped with the metered valve and was charged with the solution of propellant and PEG.
  • Table 2 Effect of combinations of drug coated with varying concentrations of PVP on the Suspension quality , FPD and valve sticking of ipratropium bromide and albuterol sulfate HFA inhaler and also.

Abstract

L'invention porte sur une formulation d'aérosol pharmaceutique comprenant un matériau actif enrobé d'un polymère en combinaison avec un propulseur, facultativement avec d'autres excipients pharmaceutiquement acceptables.
PCT/GB2008/002029 2007-06-14 2008-06-12 Formulations pour inhalation WO2008152398A2 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
IN1123/MUM/2007 2007-06-14
IN1123MU2007 2007-06-14
IN1249/MUM/2007 2007-06-29
IN1249MU2007 2007-06-29
IN1253MU2007 2007-07-02
IN1253/MUM/2007 2007-07-02

Publications (2)

Publication Number Publication Date
WO2008152398A2 true WO2008152398A2 (fr) 2008-12-18
WO2008152398A3 WO2008152398A3 (fr) 2009-11-12

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PCT/GB2008/002029 WO2008152398A2 (fr) 2007-06-14 2008-06-12 Formulations pour inhalation

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009095681A2 (fr) * 2008-02-01 2009-08-06 Vectura Limited Formulations pour suspensions
WO2012030309A3 (fr) * 2010-09-01 2012-08-09 Mahmut Bilgic Formulation d'un inhibiteur des canaux calciques
WO2013053696A1 (fr) 2011-10-11 2013-04-18 Chiesi Farmaceutici S.P.A. Microparticules cristallines d'un bêta-agoniste enrobé d'un acide gras
WO2014016653A1 (fr) 2012-07-26 2014-01-30 Wockhardt Limited Composition pharmaceutique comprenant de la diamorphine destinée à une administration intranasale
WO2014064410A3 (fr) * 2012-10-23 2014-08-07 Cipla Limited Composition pharmaceutique
WO2016018892A1 (fr) * 2014-07-29 2016-02-04 3M Innovative Properties Company Procédé de préparation d'une composition pharmaceutique
CN106551909A (zh) * 2015-09-23 2017-04-05 苏州欧米尼医药有限公司 一种高分散微细粉体颗粒的制备方法
CN110840864A (zh) * 2019-12-20 2020-02-28 广州健康元呼吸药物工程技术有限公司 一种β2受体激动剂吸入气雾剂及包含该吸入气雾剂的产品

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WO1999038493A1 (fr) * 1998-01-30 1999-08-05 Rtp Pharma Inc. Formulations d'inhalation de microparticules
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WO2003063843A1 (fr) * 2002-02-01 2003-08-07 Astrazeneca Ab Composition pour inhalation
US6641800B1 (en) * 1991-09-25 2003-11-04 Fisons Ltd. Pressurized aerosol compositions comprising powdered medicament dispersed in hydrofluoroalkane
WO2005055985A1 (fr) * 2003-12-10 2005-06-23 Medpharm Limited Preparations pour inhalation dosee de medicaments therapeutiques
WO2005056037A1 (fr) * 2003-12-10 2005-06-23 Medpharm Limited Preparations pour inhalation dosees de proteines et de peptides

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US6641800B1 (en) * 1991-09-25 2003-11-04 Fisons Ltd. Pressurized aerosol compositions comprising powdered medicament dispersed in hydrofluoroalkane
WO1998034596A2 (fr) * 1997-02-07 1998-08-13 Minnesota Mining And Manufacturing Company Composes biocompatibles destines a des systemes d'apport de medicaments
WO1999038493A1 (fr) * 1998-01-30 1999-08-05 Rtp Pharma Inc. Formulations d'inhalation de microparticules
WO2002003958A1 (fr) * 2000-07-11 2002-01-17 Astrazeneca Ab Nouvelle preparation en aerosol contenant une molecule fluoree polaire
WO2003063843A1 (fr) * 2002-02-01 2003-08-07 Astrazeneca Ab Composition pour inhalation
WO2005055985A1 (fr) * 2003-12-10 2005-06-23 Medpharm Limited Preparations pour inhalation dosee de medicaments therapeutiques
WO2005056037A1 (fr) * 2003-12-10 2005-06-23 Medpharm Limited Preparations pour inhalation dosees de proteines et de peptides

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009095681A2 (fr) * 2008-02-01 2009-08-06 Vectura Limited Formulations pour suspensions
WO2009095681A3 (fr) * 2008-02-01 2010-05-14 Vectura Limited Formulations pour suspensions
US9011923B2 (en) 2008-02-01 2015-04-21 Innovata Biomed Limited Suspension formulations
WO2012030309A3 (fr) * 2010-09-01 2012-08-09 Mahmut Bilgic Formulation d'un inhibiteur des canaux calciques
WO2013053696A1 (fr) 2011-10-11 2013-04-18 Chiesi Farmaceutici S.P.A. Microparticules cristallines d'un bêta-agoniste enrobé d'un acide gras
WO2014016653A1 (fr) 2012-07-26 2014-01-30 Wockhardt Limited Composition pharmaceutique comprenant de la diamorphine destinée à une administration intranasale
WO2014064410A3 (fr) * 2012-10-23 2014-08-07 Cipla Limited Composition pharmaceutique
WO2016018892A1 (fr) * 2014-07-29 2016-02-04 3M Innovative Properties Company Procédé de préparation d'une composition pharmaceutique
US11497712B2 (en) 2014-07-29 2022-11-15 Kindeva Drug Delivery L.P. Method of preparing a pharmaceutical composition
CN106551909A (zh) * 2015-09-23 2017-04-05 苏州欧米尼医药有限公司 一种高分散微细粉体颗粒的制备方法
CN110840864A (zh) * 2019-12-20 2020-02-28 广州健康元呼吸药物工程技术有限公司 一种β2受体激动剂吸入气雾剂及包含该吸入气雾剂的产品
CN110840864B (zh) * 2019-12-20 2022-02-22 广州健康元呼吸药物工程技术有限公司 一种β2受体激动剂吸入气雾剂及包含该吸入气雾剂的产品

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