WO2004017914A2 - Compositions a inhaler - Google Patents

Compositions a inhaler Download PDF

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Publication number
WO2004017914A2
WO2004017914A2 PCT/US2003/026385 US0326385W WO2004017914A2 WO 2004017914 A2 WO2004017914 A2 WO 2004017914A2 US 0326385 W US0326385 W US 0326385W WO 2004017914 A2 WO2004017914 A2 WO 2004017914A2
Authority
WO
WIPO (PCT)
Prior art keywords
dry powder
microns
lactose
diameter
less
Prior art date
Application number
PCT/US2003/026385
Other languages
English (en)
Other versions
WO2004017914A8 (fr
WO2004017914A3 (fr
Inventor
Xian-Ming Zeng
Original Assignee
Ivax Corporation
Norton Healthcare Ltd.
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
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=9942746&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2004017914(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to AU2003269989A priority Critical patent/AU2003269989B8/en
Priority to EA200500389A priority patent/EA007377B1/ru
Priority to NZ538965A priority patent/NZ538965A/en
Priority to MXPA05001903A priority patent/MXPA05001903A/es
Priority to CA2499273A priority patent/CA2499273C/fr
Priority to BRPI0313647A priority patent/BRPI0313647A2/pt
Priority to AT03751884T priority patent/ATE520405T1/de
Priority to KR1020057002937A priority patent/KR101369631B1/ko
Priority to JP2004529873A priority patent/JP2006516531A/ja
Priority to EP03751884A priority patent/EP1599209B1/fr
Application filed by Ivax Corporation, Norton Healthcare Ltd. filed Critical Ivax Corporation
Publication of WO2004017914A2 publication Critical patent/WO2004017914A2/fr
Publication of WO2004017914A3 publication Critical patent/WO2004017914A3/fr
Priority to TNP2005000047A priority patent/TNSN05047A1/en
Priority to IL167009A priority patent/IL167009A/en
Priority to NO20051461A priority patent/NO20051461L/no
Publication of WO2004017914A8 publication Critical patent/WO2004017914A8/fr

Links

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
    • A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles

Definitions

  • This invention relates to dry powder inhalation compositions, their preparation and use.
  • it is concerned with formulations of the medicament formoterol and pharmaceutically acceptable derivatives thereof mixed with particulate lactose.
  • inhalation drugs are typically provided in micronized form with average particle sizes of up to 10 microns.
  • DPI dry powdered inhaler
  • the device may be a single dose device (e.g., wherein drug is dispensed from a pre-metered dosage means such as a capsule) or multidose (where the drug is stored in a reservoir and then metered prior to dispersal in the air stream or where the drug is pre-metered and then stored in multiple dosage packs such as blisters).
  • a single dose device e.g., wherein drug is dispensed from a pre-metered dosage means such as a capsule
  • multidose where the drug is stored in a reservoir and then metered prior to dispersal in the air stream or where the drug is pre-metered and then stored in multiple dosage packs such as blisters.
  • the particulate drug is mixed with an excipient powder of larger average particle size and the drug particles are blended with the excipient to create a generally homogenous mixture.
  • the larger particle size of the excipient results in the powder mixture being flowable, and the homogeneity of the mixture enable it to be metered into accurately measurable doses. This is of particular
  • U.S. Patent 6, 199,607 to Trofast describes a multi-step process for preparing a dry powder formoterol composition.
  • the process as described includes the mixing of the components followed by micronization of the blend.
  • the micronized particles were subsequently treated to remove amorphous areas in their crystal structure.
  • the particles are then agglomerated, sieved, and spheronized, followed by a second sieving, spheronization and sieving.
  • the invention provides compositions for the dry powder inhalation of medicament comprising particulate medicament and a lactose carrier of defined particulate sizes and proportions.
  • the compositions provide for an accurate, uniform and consistent dispersion when used with, for example, a multidose dry powder inhaler. Also disclosed are methods for use of the compositions of the invention.
  • dry powder inhalation compositions of a particulate medicament e.g., formoterol
  • lactose of defined particulate size and proportions are described which are easier to handle, and can be readily filled into the reservoir of a multidose dry powder inhaler (MDPI), (see, for example, WO 92/10229).
  • MDPI multidose dry powder inhaler
  • these compositions are more accurately metered and provide more uniform and consistent dispersions when dispensed by MDPI devices.
  • Certain compositions may also be more stable.
  • One aspect of the invention provides a dry powder inhalation composition
  • a dry powder inhalation composition comprising medicament particles and a mixture of lactose particles with a NMD of between about 70 and about 120 microns and a diameter of less than 250 microns, the mixture being characterized in that up to 96% by weight of the lactose particles are less than 150 microns in diameter and wherein up to 25% by weight of the lactose particles are less than 5 microns in diameter.
  • Another aspect of the invention provides for a multidose dry powder inhaler comprising the composition according to the invention.
  • An aspect of the invention provides methods for the administration of a particulate medicament, comprising inhalation of a composition of the invention from a multidose dry powder inhaler, are provided.
  • the invention provides a method for the administration of a therapeutically effective amount of compositions prepared by the processes of the invention, for the treatment of conditions responsive to the medicaments of choice.
  • Figure 1 Graphical representation of particle size distribution for lactose particles.
  • Figure 2 Graphical representation of drug per actuation from a representative commercial product with a label claim of 6 ⁇ g formoterol (OXIS TURBUHALERTM, Batch ZE226).
  • Figure 3 Graphical representation of drug delivery per actuation from an IVAXTM MDPI with a label claim of 6 ⁇ g.
  • the invention provides compositions for the dry powder inhalation of medicament comprising particulate medicament and a lactose carrier of defined particulate sizes and proportions.
  • the compositions provide for a more accurate, uniform and consistent dispersion when used with, for example, a multidose dry powder inhaler. Also disclosed are methods for use of the compositions of the invention.
  • the terms “comprise(s)” and “comprising” are to be interpreted as having an open- ended meaning. That is, the terms are to be interpreted synonymously with the phrases “having at least” or “including at least”.
  • the term “comprising” means that the process includes at least the recited steps, but may include additional steps.
  • the term “comprising” means that the compound or composition includes at least the recited features or components, but may also include additional features or components.
  • One aspect of the invention provides a dry powder inhalation composition
  • a dry powder inhalation composition comprising medicament particles and a mixture of lactose particles with a volume mean diameter (NMD) of between about 70 and about 120 microns and a diameter of less than 250 microns, the mixture being characterized in that up to 96% by weight of the lactose particles are less than 150 microns in diameter and wherein up to 25% by weight of the lactose particles are less than 5 microns in diameter.
  • NMD volume mean diameter
  • up to 85% by weight of the lactose particles are less than 90 microns in diameter, whereas in another embodiment up to 37% by weight of the lactose particles are less than 60 microns in diameter.
  • up to 35% by weight of the lactose particles are less than 30 microns in diameter, while in still other embodiments up to 31.5% by weight of the lactose particles are less than 15 microns in diameter.
  • up to 30% by weight of the lactose particles are less than 10 microns in diameter, and in some embodiments between 6.5 and 24.5% by weight of the lactose are less than 5 microns in diameter.
  • the composition comprises up to 10% by weight of medicament.
  • the medicament is formoterol or a pharmaceutically derivative or salt thereof.
  • the medicament is formoterol fumarate dihydrate.
  • variable can be equal to any integer value of the numerical range, including the end-points of the range.
  • variable can be equal to any real value of the numerical range, including the end-points of the range.
  • a variable which is described as having values between 0 and 2 can be 0, 1 or 2 for variables which are inherently discrete, and can be 0.0, 0.1, 0.01, 0.001, or any other real value for variables which are inherently continuous.
  • Another aspect of the invention provides for a multidose dry powder inhaler comprising a composition according to the invention.
  • Another aspect of the invention provides a method for the administration of a particulate medicament, comprising inhalation from and MDI of a dry powder inhalation composition of the invention.
  • compositions according to the invention are optionally formulated in a pharmaceutically acceptable vehicle with any of the well-known pharmaceutically acceptable medically inert moiety such as carriers, including diluents, excipients, surfactants, and flavourings (see Remington's Pharmaceutical Sciences, 18 th Ed., Gennaro, Mack Publishing Co., Easton, PA 1990 and Remington: The Science and Practice of Pharmacy, Lippincott, Williams & Wilkins, 1995). While the type of pharmaceutically acceptable carrier/vehicle employed in generating the compositions of the invention will vary depending upon the mode of administration of the composition to a mammal, generally pharmaceutically acceptable carriers are physiologically inert and non-toxic. See also Zeng, et al. Particulate Interactions in Dry Powder Formulations of Inhalation, Taylor & Francis, London, 2001.
  • bronchodilators e.g., epinephrine, metaproterenol, terbutaline, albuterol, and the like
  • anticholinergic agents e.g., ipratropium bromide
  • xanthines e.g., dyphylline, aminophylline
  • corticosteroids e.g., flunisolide, beclomethasone, budesonide, and the like
  • ⁇ -2 adrenergic receptor agonists e.g., salmeterol and formoterol.
  • the medicament may be in any isomeric form or mixture of isomeric forms, for example a pure enantiomer, particularly the R, R-enantiomer, a mixture of enantiomers, a racemate or a mixture thereof (e.g., formoterol).
  • Pharmaceutically acceptable derivatives of formoterol include pharmaceutically acceptable salts, in particular acid addition salts with inorganic acids such as hydrochloric acid, hydrobromic acid, sulphuric or phosphoric acid.
  • the salt may also be with an organic acid such as acetic, succinic, maleic, furmaric, citric, tartaric, lactic or benzoic.
  • the active ingredient and pharmaceutically acceptable derivatives thereof may exist in the form of a solvate, in particular a hydrate.
  • a form of active ingredient for use in the invention is formoterol fumarate, especially formoterol fumarate dihydrate, conveniently in its racemic form.
  • Formoterol, salts and hydrates thereof and salt hydrates thereof as described above may be prepared by known methods, for example as described in U.S. Patent 3,994,974 or U.S. Patent 5,684,199.
  • the medicament is present in the dry powder composition at an amount which is less than 10 %, preferably less than 2 % and most preferably less than 1 % by weight of the composition.
  • the actual amount of medicament in the composition will depend to a large extent on the nature of the dry powder inhaler and the quantity of composition that is metered for each individual dose. Where a large dose of composition is metered, the proportion of the medicament in the dose will be reduced.
  • Particularly dilute compositions are disclosed in WO 01/39745, for example, 0.02 % by weight.
  • the mean particle diameter of the medicament is up to 10 microns in diameter, while in other embodiments, the mean particle size is up to 5 microns in diameter. In yet other embodiments, the mean particle size ranges from about 1 to about 5 microns in diameter.
  • the particle size of the medicament can be reduced to the desired level by conventional means, for example by grinding in a mill, for example, an air jet, ball or vibrator mill, by sieving, by crystallization, by spray-drying or by lyophilization. Particle size may be determined using laser light scattering (Sympatec GmbH, Claasthal-Zellerfeld, Germany).
  • the desired particle size distribution of the lactose may be prepared in a similar way. However, it is preferable to prepare the lactose by blending two or more portions of previously prepared and classified lactose, for example a fine blend of lactose, in which the mean particle diameter is less than 10 microns in diameter and a portion in which the mean particle diameter is relatively coarse. A characteristic coarse lactose is supplied as classified lactose, which is collected on a mesh with mesh size of 63 microns, after passing through a mesh with mesh size of 90 microns. [0041] The formulations of the compositions of the invention may conveniently be presented in unit dosage form and may be prepared by conventional pharmaceutical techniques.
  • Such techniques include the step of bringing into association the compound of the invention and the pharmaceutically acceptable carrier(s), or an excipient.
  • the formulations are prepared by uniformly and intimately bringing into association the active ingredient with finely divided solid carriers, and then, if necessary, preparing discrete dosage units of the product.
  • the dry powder composition may be metered and filled into capsules, e.g., gelatin or hydroxypropyl methylcellulose capsules, such that the capsule contains a unit dose of medicament.
  • capsules e.g., gelatin or hydroxypropyl methylcellulose capsules
  • Doses of medicament to be used in accordance with the invention may range in general from 1 to 60 micrograms.
  • the dose may range, for example, from 6 to 54 micrograms.
  • Preferred doses are from 6 to 24 micrograms, especially the unit doses of 6 micrograms, 12 micrograms and 24 micrograms. These doses may be administered once or twice daily.
  • the total amount of composition will depend on the size of the capsules and the characteristics of the inhalation device with which the capsules are being used. However, representative characteristic total fill weights of dry powder to per capsule are between 1 and 25 mg, e.g., 5, 10, 15 or 20 mg.
  • the dry powder composition according to the invention may be filled into the reservoir of a multidose dry powder inhaler (MDPI), for example of the kind illustrated in WO 92/10229 (hereinafter referred to as the INAXTM MDPI).
  • MDPI multidose dry powder inhaler
  • compositions according to the invention may be readily prepared by blending the required amount of active ingredient with the required amount of particulate lactose of the desired particle size distribution.
  • the lactose is alpha lactose monohydrate.
  • the invention provides a method for the administration of a therapeutically effective amount of compositions prepared by the processes described herein, for the treatment of conditions responsive to the medicaments of choice.
  • conditions include chronic obstructive pulmonary disease, asthma, late phase allergic responses, or pulmonary inflammations.
  • therapeutically effective amount is used to denote treatments at dosages effective to achieve the therapeutic result sought.
  • therapeutically effective amount of the compositions of the invention may be lowered or increased by fine tuning and/or by administering more than one composition of the invention, or by administering a composition of the invention with another compound or composition.
  • the invention therefore provides a method to tailor the administration/treatment to the particular exigencies specific to a given mammal.
  • Example 1 Particle size distribution, dose delivery, and fine particle fractions for a formoterol lactose blend
  • Particle size distributions for carrier lactose must be in the range of 70 - 120 ⁇ m.
  • the inhalers that contained the formulation were then tested for pharmaceutical performance under conditions specified in European Pharmacopoeia (2001) including uniformity of delivered dose and fine particle dose.
  • the drug per actuation (DP A) was measured using a dose unit sampling unit in conjunction with a critical flow controller model TPK, high capacity pump and fiowmeter (Copley Scientific, Nottingham, U.K.) while fine particle dose (FPD) and fine particle fraction (FPF) were measured using a 5 -stage liquid impinger MSL also from Copley Scientific.
  • compositions gave excellent dose uniformity with relative standard deviation (RSD) of delivered doses ranging from 4-13% (Table 2) when used in association with the INAX TM MDPI device, with a good proportion of fine particles of the drug (Table 3).
  • RSD relative standard deviation
  • Relative standard deviation often doses (3 at beginning, 4 at middle and 3 at end of device life) from each inhaler device containing a formulation using the said lactose as the excipient before and after storage unprotected at 25°C/60% RH for a month.
  • Example 2 Particle size distribution for a formoterol lactose blend
  • Example 4 0.265 grams of formoterol (as the fumarate dihydrate salt) was blended according to the methods of Example 1, with 99.735 grams of lactose that has a particle size distribution within the range as shown in Table 4.
  • the lactose was prepared by blending a mixture of 90 to 150 micron lactose (95%) with microfine lactose having a NMD of 7.5 microns (5%).
  • the formoterol lactose blend was filled into the reservoir of an INAX MDPI dry powder inlialer. A typical particle size distribution for a lactose blend thus prepared is shown in Fig. 1. Table 4:
  • the commercial product (Fig. 2) showed a larger variation in DPA than the compositions as used with an INAX T MDPI (Fig. 3).
  • the mean DPA from three commercial products (with label claim of 6 ⁇ g) was 3.9 ⁇ g, suggesting that a large portion (over 30%) of the drug was not released from the device.
  • the mean DPA from three INAXTM MDPIs was 5.3 ⁇ g, (within 80-120% of the label claim of 6 ⁇ g).
  • the three commercial devices showed an RSD of 27.8% for the DPA values which was more than twice the value (11.9%) of the INAX TM MDPI, indicating a more consistent delivery of drug.
  • RD is the total recovered dose from the impinger; LC is label claim and IND. Port stands for Induction Port.
  • a blend composed of 0.26% w/w micronized formoterol in the lactose was prepared as previously described. The final products were found to produce a mean drug per actuation within 80-120% label claim, mean fine particle dose expressed as percentage of label claim > 37%. All parameters met Pharmacopoeial specifications set up for dry powder inhalers, previously cited. The fine particle dose for the composition when used in conjunction with an INAXTM MDPI, which relates directly to the therapeutic equivalence of these inhalers, was comparable to the representative commercial product. Delivery of the composition of the invention with an INAX MDPI was shown to be more consistent in the delivery of formoterol than the commercial product. (Data not shown)
  • bronchodilators e.g., epinephrine, metaproterenol, terbutaline, albuterol, and the like
  • anticholinergic agents e.g., ipratropium bromide
  • the resulting blend is introduced into an INAX MDPI and then tested for pharmaceutical performance under the conditions specified in European Pharmacopoeia.
  • the drug per actuation (DPA) is measured using a dose unit sampling unit while fine particle dose (FPD) and fine particle fraction (FPF) are measured using a 5-stage liquid impinger as previously described.
  • DPA drug per actuation
  • FPD fine particle dose
  • FPF fine particle fraction

Abstract

L'invention porte sur une composition à inhaler de poudre sèche contenant des particules de médicament et un mélange de particules de lactose avec diamètre volumétrique moyen compris entre environ 70 et 120 microns et un diamètre inférieur à 250 microns. Le mélange se caractérise par le fait que jusqu'à 96 % en poids des particules de lactose possèdent un diamètre inférieur à 150 microns, 25 % en poids des particules de lactose ont un diamètre inférieur à 5 microns. Ces compositions fournissent une dispersion plus précise, uniforme et régulière lorsqu'elles sont utilisées par exemple avec un inhalateur de poudre sèche. L'invention concerne aussi des procédés d'utilisation des compositions susmentionnées.
PCT/US2003/026385 2002-08-21 2003-08-21 Compositions a inhaler WO2004017914A2 (fr)

Priority Applications (13)

Application Number Priority Date Filing Date Title
KR1020057002937A KR101369631B1 (ko) 2002-08-21 2003-08-21 흡입용 조성물
EP03751884A EP1599209B1 (fr) 2002-08-21 2003-08-21 Compositions a inhaler
JP2004529873A JP2006516531A (ja) 2002-08-21 2003-08-21 吸入組成物
MXPA05001903A MXPA05001903A (es) 2002-08-21 2003-08-21 Composicion para inhalacion.
EA200500389A EA007377B1 (ru) 2002-08-21 2003-08-21 Композиции для ингаляции
BRPI0313647A BRPI0313647A2 (pt) 2002-08-21 2003-08-21 composições de inalação
AT03751884T ATE520405T1 (de) 2002-08-21 2003-08-21 Inhalationszusammensetzung
AU2003269989A AU2003269989B8 (en) 2002-08-21 2003-08-21 Inhalation composition
NZ538965A NZ538965A (en) 2002-08-21 2003-08-21 Dry powder inhalation compositions
CA2499273A CA2499273C (fr) 2002-08-21 2003-08-21 Compositions a inhaler
TNP2005000047A TNSN05047A1 (en) 2002-08-21 2005-02-18 Inhalation composition
IL167009A IL167009A (en) 2002-08-21 2005-02-21 Dry powder formoterol or its derivatives for inhalation
NO20051461A NO20051461L (no) 2002-08-21 2005-03-18 lnhaleringssammensetning

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB02119513.9 2002-08-21
GB0219513A GB0219513D0 (en) 2002-08-21 2002-08-21 Inhalation compositions including coarse carrier
GB02119513.7 2002-08-21

Publications (3)

Publication Number Publication Date
WO2004017914A2 true WO2004017914A2 (fr) 2004-03-04
WO2004017914A3 WO2004017914A3 (fr) 2004-04-29
WO2004017914A8 WO2004017914A8 (fr) 2005-07-07

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/026385 WO2004017914A2 (fr) 2002-08-21 2003-08-21 Compositions a inhaler

Country Status (8)

Country Link
BR (1) BRPI0313647A2 (fr)
CA (1) CA2499273C (fr)
ES (1) ES2371601T3 (fr)
GB (1) GB0219513D0 (fr)
NO (1) NO20051461L (fr)
TN (1) TNSN05047A1 (fr)
WO (1) WO2004017914A2 (fr)
ZA (1) ZA200502177B (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007112267A3 (fr) * 2006-03-23 2008-03-13 3M Innovative Properties Co Processus de remplissage de poudre
WO2008134817A1 (fr) * 2007-05-03 2008-11-13 The University Of Sydney Vecteurs composites pour thérapie par inhalation de poudre sèche
US8114438B2 (en) 2004-04-23 2012-02-14 Cydex Pharmaceuticals, Inc. DPI formulation containing sulfoalkyl ether cyclodextrin
WO2012166070A1 (fr) * 2011-06-02 2012-12-06 Mahmut Bilgic Formulation de poudre sèche ayant des caractéristiques d'écoulement améliorées
WO2013009271A1 (fr) * 2011-06-02 2013-01-17 Mahmut Bilgic Nouvelle formulation améliorée de poudre sèche
US8511302B2 (en) 2004-04-24 2013-08-20 Innovata Biomed Limited Dose counter mechanisms for medicament delivery devices
US8846901B2 (en) 2005-10-26 2014-09-30 Cydex Pharmaceuticals, Inc. Sulfoalkyl ether cyclodextrin compositions and methods of preparation thereof
US8851069B2 (en) 2004-04-21 2014-10-07 Innovata Biomed Limited Inhaler
EP1848444B1 (fr) 2005-02-10 2016-11-09 Glaxo Group Limited Procedes de fabrication du lactose au moyen de techniques de pre-classification et preparations pharmaceutiques ainsi obtenues
US9675666B2 (en) 2014-06-03 2017-06-13 Asahi Calpis Wellness Co., Ltd. Immediate-release tablet formulation, composition for tablets and method for manufacturing immediate-release tablet formulation
US10370183B2 (en) 2012-07-19 2019-08-06 Adamis Pharmaceuticals Corporation Powder feeding apparatus
EP2682099B1 (fr) 2012-07-05 2020-09-02 Arven Ilac Sanayi Ve Ticaret A.S. Compositions d'inhalateur de poudre sèche comprenant des antagonistes muscariniques à action prolongée

Citations (2)

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US20020106332A1 (en) 2000-10-12 2002-08-08 Michael Walz Process for preparing powder formulations
US20020110529A1 (en) 2000-10-12 2002-08-15 Karoline Bechtold-Peters Inhalable powder containing tiotropium

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EP1862164A3 (fr) * 1998-11-13 2012-12-26 Jagotec AG Poudre sèche pour inhalation
DE69818872T2 (de) * 1998-12-11 2004-05-19 Pharmachemie B.V. Pharmazeutische zubereitungen zur inhalation eines opioids

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US20020106332A1 (en) 2000-10-12 2002-08-08 Michael Walz Process for preparing powder formulations
US20020110529A1 (en) 2000-10-12 2002-08-15 Karoline Bechtold-Peters Inhalable powder containing tiotropium

Non-Patent Citations (1)

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Title
See also references of EP1599209A2

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8851069B2 (en) 2004-04-21 2014-10-07 Innovata Biomed Limited Inhaler
US11464862B2 (en) 2004-04-23 2022-10-11 Cydex Pharmaceuticals, Inc. DPI formulation containing sulfoalkyl ether cyclodextrin
US8114438B2 (en) 2004-04-23 2012-02-14 Cydex Pharmaceuticals, Inc. DPI formulation containing sulfoalkyl ether cyclodextrin
US10668160B2 (en) 2004-04-23 2020-06-02 Cydex Pharmaceuticals, Inc. DPI formulation containing sulfoalkyl ether cyclodextrin
US10117940B2 (en) 2004-04-23 2018-11-06 Cydex Pharmaceuticals, Inc. DPI formulation containing sulfoalkyl ether cyclodextrin
US8511302B2 (en) 2004-04-24 2013-08-20 Innovata Biomed Limited Dose counter mechanisms for medicament delivery devices
EP1848444B1 (fr) 2005-02-10 2016-11-09 Glaxo Group Limited Procedes de fabrication du lactose au moyen de techniques de pre-classification et preparations pharmaceutiques ainsi obtenues
EP3199164B1 (fr) * 2005-02-10 2020-03-18 Glaxo Group Limited Procedes de fabrication du lactose au moyen de techniques de pre-classification et preparations pharmaceutiques ainsi obtenues
US9617352B2 (en) 2005-10-26 2017-04-11 Cydex Pharmaceuticals, Inc. Sulfoalkyl ether cyclodextrin compositions and methods of preparation thereof
US8846901B2 (en) 2005-10-26 2014-09-30 Cydex Pharmaceuticals, Inc. Sulfoalkyl ether cyclodextrin compositions and methods of preparation thereof
US10202468B2 (en) 2005-10-26 2019-02-12 Cydex Pharmaceuticals, Inc. Sulfoalkyl ether cyclodextrin compositions and methods of preparation thereof
US10703826B2 (en) 2005-10-26 2020-07-07 Cydex Pharmaceuticals, Inc. Sulfoalkyl ether cyclodextrin compositions and methods of preparation thereof
US8997799B2 (en) 2006-03-23 2015-04-07 Adamis Pharmaceuticals Corporation Powder filling processes
WO2007112267A3 (fr) * 2006-03-23 2008-03-13 3M Innovative Properties Co Processus de remplissage de poudre
US10022508B2 (en) 2006-03-23 2018-07-17 Adamis Pharmaceuticals Corporation Powder filling processes
WO2008134817A1 (fr) * 2007-05-03 2008-11-13 The University Of Sydney Vecteurs composites pour thérapie par inhalation de poudre sèche
WO2013009271A1 (fr) * 2011-06-02 2013-01-17 Mahmut Bilgic Nouvelle formulation améliorée de poudre sèche
WO2012166070A1 (fr) * 2011-06-02 2012-12-06 Mahmut Bilgic Formulation de poudre sèche ayant des caractéristiques d'écoulement améliorées
EP2682099B1 (fr) 2012-07-05 2020-09-02 Arven Ilac Sanayi Ve Ticaret A.S. Compositions d'inhalateur de poudre sèche comprenant des antagonistes muscariniques à action prolongée
US10370183B2 (en) 2012-07-19 2019-08-06 Adamis Pharmaceuticals Corporation Powder feeding apparatus
US9675666B2 (en) 2014-06-03 2017-06-13 Asahi Calpis Wellness Co., Ltd. Immediate-release tablet formulation, composition for tablets and method for manufacturing immediate-release tablet formulation

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TNSN05047A1 (en) 2007-05-14
ES2371601T3 (es) 2012-01-05
BRPI0313647A2 (pt) 2019-02-19
WO2004017914A8 (fr) 2005-07-07
ZA200502177B (en) 2006-05-31
CA2499273A1 (fr) 2004-03-04
CA2499273C (fr) 2011-06-21
GB0219513D0 (en) 2002-10-02
NO20051461L (no) 2005-05-20
WO2004017914A3 (fr) 2004-04-29

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