WO2013109219A1 - Formulations en poudre sèche comprenant du tiotropium et du carmotérol - Google Patents

Formulations en poudre sèche comprenant du tiotropium et du carmotérol Download PDF

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Publication number
WO2013109219A1
WO2013109219A1 PCT/TR2013/000031 TR2013000031W WO2013109219A1 WO 2013109219 A1 WO2013109219 A1 WO 2013109219A1 TR 2013000031 W TR2013000031 W TR 2013000031W WO 2013109219 A1 WO2013109219 A1 WO 2013109219A1
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WO
WIPO (PCT)
Prior art keywords
range
excipient
pharmaceutical formulation
formulation according
particle size
Prior art date
Application number
PCT/TR2013/000031
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English (en)
Inventor
Mahmut Bilgic
Original Assignee
Mahmut Bilgic
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 Mahmut Bilgic filed Critical Mahmut Bilgic
Priority to EP13720141.4A priority Critical patent/EP2804590A1/fr
Publication of WO2013109219A1 publication Critical patent/WO2013109219A1/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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4816—Wall or shell material
    • A61K9/4825—Proteins, e.g. gelatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4704—2-Quinolinones, e.g. carbostyril
    • 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
    • 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
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds

Definitions

  • the present invention relates to pharmaceutical formulations in dry powder form comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof in order to be used in symptomatic and/or prophylactic treatment of respiratory tract diseases, particularly asthma and COPD.
  • P2-adrenergic agonists used in the treatment of respiratory tract diseases such as asthma and COPD activate 2-adrenergic receptors and affect the muscles around the airways; alleviate or remove bronchospasm.
  • Carmoterol belongs to this group.
  • Another group of active agents used in the treatment of respiratory tract diseases is anticholinergics. Anticholinergics affect the muscles on bronchi including large airways. Like p2-adrenergic agonists, these drugs divide into two as short-acting and long-acting too. Short-acting anticholinergics are generally used to alleviate symptoms while long-acting anticholinergics are used to prevent inhalation problems.
  • Ipratropium bromide and oxitropium bromide can be listed among short-acting anticholinergics.
  • Tiotropium is a long- acting anticholinergic agent. Tiotropium starts to act in 20 minutes following its intake and its effects can be observed in 24 hours thus it suffices to take tiotropium once a day.
  • combination drugs in the treatment of respiratory tract diseases such as asthma and COPD is quite effective, particularly in reducing the number of asthma attacks. Since activity of the active agents used in combination drugs can be enabled in smaller doses compared to their use alone, severity of potential side effects and/or their possibility of occurrence can decrease.
  • the dry powder formulation comprising active agent combination has good flow characteristics is an important criterion in terms of inhalation of said formulation effectively and therefore in terms of providing an effective treatment.
  • a dry powder formulation which does not have good flow characteristics is obtained, it is seen that the formulation has low homogeneity and consequently dosing accuracy cannot be ensured during filling the dry powder formulation prepared into reservoirs of multi dose inhalators comprising more than one dose or into blister cavities of a blister package, each of them comprising one dose, or into capsules comprising one dose.
  • the fact that the dry powder formulation does not have good flow characteristics affects emptying capacity and emptying attribute negatively during inhalation of the formulation from capsule, blister or reservoir. As a result, due to the reasons listed above, the active agents cannot reach to the lungs in sufficient amounts.
  • the active agents are diluted by various non-functional excipients.
  • the physical characteristics of these excipients, used in quite high amounts as compared to the active agent amount in the formulations, such as average particle size have an important role in providing good flow in the dry powder formulation. Since the active agents used are delivered to the lungs in sufficient amounts and in a controlled manner in the dry powder formulation having good flow characteristics, desired therapeutic effect is obtained.
  • the inventors have developed dry powder formulations which comprise tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof and have high homogeneity and good flow characteristics wherein dosing accuracy is ensured and sufficient amount of active agent can be delivered to the lungs.
  • the present invention relates to pharmaceutical formulations in dry powder form comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof.
  • dry powder formulations which comprise tiotropium and carmoterol having a ratio in the range of 30:1 to 1 :1, preferably in the range of 25:1 to 2:1 to each other by weight and also at least one pharmaceutically acceptable fine grained and coarse grained excipient having an average particle size ratio to each other in the range of 1 :30 to 1 :2, preferably in the range of 1 :20 to 1 :5, more preferably in the range of 1 : 15 to 1 : 10 have good flow characteristics and high homogeneous dispersion, therefore dose accuracy is obtained in the formulations and sufficient amount of active agent can be delivered to the lungs.
  • the fine grained excipient used in the text refers to an excipient having an average particle size less than 10 ⁇ ⁇ ⁇ , preferably in the range of 0.1 to 9.9 ⁇ , more preferably in the range of 2 to 8 ⁇ ⁇ , for instance in the range of 0.3, 0.5, 0.7, 0.9, 1.1, 1.3, 1.5, 1.7, 1.9, 2.3, 2.5, 3.0, 3.5, 4.0, 4.5 to 5.0, 5.5, 6.0, 6.5, 7.0, 7.5, 8.0, 8.5, 9.0, 9.5 ⁇ ; the coarse grained excipient used in the text refers to an excipient having an average particle size in the range of 10 to 90 ⁇ , preferably in the range of 12 to 85 ⁇ , more preferably in the range of 15 to 80 ⁇ , for instance in the range of 15, 20, 25, 30, 35, 40, 45 to 50, 55, 60, 65, 70, 75, 80, 85 ⁇ .
  • the subject of the present invention is the pharmaceutical formulation in dry
  • the ratio of tiotropium and carmoterol to each other respectively is in the range of 30:1 to 1 : 1 , preferably in the range of 25: 1 to 2: 1 by weight,
  • the excipient comprised in said formulation is composed of at least one pharmaceutically acceptable excipient mixture comprising fine grained excipient and coarse grained excipient and
  • the average particle size ratio of the fine grained excipient to the coarse grained excipient is in the range of 1 :30 to 1 :2, preferably in the range of 1 :20 to 1 :5, more preferably in the range of 1 : 15 to 1 : 10.
  • tiotropium and/or pharmaceutically acceptable derivatives thereof which is one of the active agents comprised in the dry powder drug formulation comprising the active agent combination refers to tiotropium' s free base, pharmaceutically acceptable solvates, hydrates, enantiomers or diastereomers, racemates, organic salts, inorganic salts, esters, polymorphs, crystalline forms and amorphous forms and/or combinations thereof.
  • carmoterol and/or pharmaceutically acceptable derivatives thereof which is one of the active agents comprised in the dry powder drug formulation comprising the active agent combination refers to carmoterol' s free base, pharmaceutically acceptable solvates, hydrates, enantiomers or diastereomers, racemates, organic salts, inorganic salts, esters, polymorphs, crystalline forms and amorphous forms and/or a combination thereof.
  • the inhalation formulation comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof can be delivered to the patient in dry powder form.
  • Said dry powder formulations further comprise at least one physiologically and pharmaceutically acceptable excipient along with the active agent.
  • This excipient is composed of fine grained excipient, coarse grained excipient or a combination thereof, preferably a combination of fine grained excipient and coarse grained excipient.
  • This excipient can be selected from monosaccharides (glucose etc.), disaccharides (lactose, saccharose, maltose or pharmaceutically acceptable hydrates, anhydrates or a combination thereof etc.), oligosaccharides and polysaccharides (dextrant etc.), polyalcohols (sorbitol, mannitol, xylitol etc.), salts (sodium chloride, calcium carbonate etc.) or a combination thereof. Same or different substances are used as fine grained excipient and coarse grained excipient, though preferably the same substance is used. Fine grained and coarse grained excipients are preferably lactose, more preferably lactose anhydrate. According to the present invention, the amount of the pharmaceutically acceptable excipient is preferably in the range of 1 -50 mg, preferably in the range of 2-40 mg, more preferably in the range of 3-30 mg.
  • the average particle size of the active agent used is quite important in order that the formulation to be obtained has good flow characteristics and therefore an effective inhalation is performed.
  • the inventors have seen that use of active agents having an average particle size in the range of 1 ⁇ to 10 ⁇ , preferably in the range of 1.5 ⁇ to 7.5 ⁇ , more preferably in the range of 1.5 ⁇ to 5 ⁇ has a significant contribution to the formulation obtained for having proper flow characteristics and for having dose uniformity and to delivery of the active agent to the lungs in sufficient amount.
  • the subject of the present invention is pharmaceutical formulations in dry powder form comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof, characterized in that
  • the ratio of tiotropium and carmoterol to each other respectively is in the range of 30:1 to 1:1, preferably in the range of 25 : 1 to 2: 1 by weight,
  • the average particle size ratio of fine grained excipient: coarse grained excipient is in the range of 1:30 to 1:2, preferably in the range of 1:20 to 1 :5, more preferably in the range of 1:15 to 1:10 and
  • the average particle size of the active agents used is in the range of 1 ⁇ to 10 ⁇ , preferably in the range of 1.5 ⁇ to 7.5 ⁇ , more preferably in the range of 1.5 ⁇ to 5 ⁇ .
  • the amounts of said fine grained and coarse grained excipients constituting the excipient combination having two different average particle sizes as fine grained and coarse grained comprised in the dry powder formulation of the present invention is an important criterion in obtaining the characteristics that can provide an effective treatment.
  • the inventors have seen that characteristics such as proper flow, particularly homogenous particle dispersion and dose uniformity of the formulation are ensured and therefore the sufficient amount of the active agent reaches to the lungs more easily in the case that the ratio of fine grained excipient to coarse grained excipient constituting the excipient combination is in the range of 1 :1 to 1 :25 by weight, preferably in the range of 1 :1 to 1 :10 by weight, more preferably in the range of 1 :1.5 to 1 :5 by weight.
  • the subject of the present invention is the pharmaceutical formulations in dry powder form comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof, characterized in that the ratio of tiotropium and carmoterol to each other respectively is in the range of 30:1 to 1 : 1 , preferably in the range of 25: 1 to 2: 1 by weight,
  • the average particle size ratio of fine grained excipient: coarse grained excipient is in the range of 1 :30 to 1 :2, preferably in the range of 1 :20 to 1 :5, more preferably in the range of 1 :15 to 1 :10 and
  • the ratio of fine grained excipient to coarse grained excipient is in the range of 1 :1 to 1 :25 by weight, preferably in the range of 1 : 1 to 1 : 10 by weight, more preferably in the range of 1 : 1.5 to 1 :5 by weight.
  • the process for preparation of the pharmaceutical formulations of the present invention in dry powder form comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof is composed of the following steps: I. micronizing tiotropium and carmoterol so as to bring them to the desired particle size,
  • the present invention relates to inhalation of the dry powder formulations comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof by using inhalation devices comprising capsule, blister or reservoir.
  • the inventors have found that the inhalation is performed most productively when capsule volume comprising the drug in dry powder form of the present invention comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof is in the range of 0.1 to 0.5 ml, preferably in the range of 0.15- 0.45 ml, more preferably in the range of 0.2-0.4 ml.
  • the present invention is characterized in that volume of the capsule used for storage and delivery of the drug in dry powder form comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof is in the range of 0.1 to 0.5 ml, preferably in the range of 0.15-0.45 ml, more preferably in the range of 0.2-0.4 ml.
  • the inventors have seen that the active agent combination comprised in the capsule is protected from external factors as well as the possibility of moistening that can arise from the nature of the capsule itself is removed in the case that moisture ratio of the package in capsule form having high protection property against moisture and other negative external factors is in the range of 5-20%, preferably in the range of 7-15%.
  • moisture ratio of the package in capsule form having high protection property against moisture and other negative external factors is in the range of 5-20%, preferably in the range of 7-15%.
  • the present invention is characterized in that moisture ratio of the package in capsule form used for storage and delivery of the drug in dry powder form comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof is in the range of 5-20%, preferably in the range of 7-15%.
  • the capsule preferred to be used in the scope of the present invention can be made of a substance selected from a group comprising gelatine, chitosan, starch and/or starch derivatives, cellulose and/or cellulose derivatives or synthetic polymers, and it is composed of telescoping body and cap parts.
  • capsule material in the case that the dry powder formulation of the present invention is inhaled from capsule, capsule material can be selected from a group comprising hydroxypropyl cellulose, hydroxypropylmethyl cellulose, methyl cellulose, hydroxymethyl cellulose, hydroxyethyl cellulose if the capsule to be used is made of cellulose and its derivatives.
  • capsule material can be selected from a group comprising polyethylene, polyester, polyethyleneterephthalate, polycarbonate or polypropylene if the capsule to be used is made of synthetic polymer.
  • various molecular weighted polyethylene glycol, sorbitol, glycerol, propylene glycol, polyethylene oxide-propylene oxide block copolymers and/or other polyalcohols and polyethers can be added as adjuvant if the capsule material to be used is made of gelatine.
  • the inventors have found that in the case that fullness ratio of the capsule cavity used is in the range of 0.05 to 25%, preferably in the range of 0.1 to 20%, more preferably in the range of 0.5-15%, an effective inhalation of the drug is ensured in the case that said dry powder formulation is inhaled from capsule.
  • the present invention is characterized in that fullness ratio of capsule cavity is in the range of 0.05 to 25%, preferably in the range of 0.1 to 20%, more preferably in the range of 0.5 to 15%.
  • the dry powder formulation of the present invention is inhaled from blister, which is one of the inhalation methods
  • the inventors have found that an effective inhalation is performed in the case that cavity volume of the blister comprising the drug in dry powder form comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof is in the range of 18-30 mm 3 , preferably in the range of 20 - 25 mm 3 , more preferably in the range of 21-24 mm 3 .
  • the present invention is characterized in that cavity volume of the blister used for storage and delivery of the drug in dry powder form comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof is 18-30 mm 3 , preferably in the range of 20 to 25 mm , more preferably in the range of 21-24 mm in the case that said dry powder formulation is inhaled from blister.
  • fullness ratio of the blister cavity used should be in the range of 15-95%, preferably in the range of 20-85% and more preferably in the range of 50-80% in order to inhale the formulation of the present invention from blister without any problem and in order to perform an effective inhalation.
  • the present invention is characterized in that fullness ratio of the blister used for storage and delivery of the drug in dry powder form comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof is in the range of 15-95%, preferably in the range of 20-85% and more preferably in the range of 50-80%.
  • the base and the lid sheets constituting the peelable blister strip pack, wherein the blisters comprising the dry powder formulation of the present invention are collocated are sealed tightly by any suitable method in order to provide impermeability.
  • the base and lid sheets constituting the peelable blister strip package comprising the dry powder formulation of the present invention are composed of many layers. Polymeric layers, aluminium foil and preferably Aclar® fluoropolymer film are among the layers constituting the base and the lid sheets.
  • the inventors have seen that, in the case that the formulation of the present invention is inhaled from blister, adding desiccant to the polymeric layers in order to reduce moisture and gas permeability of base and lid sheets constituting the blister package is effective in protecting stability of said dry powder formulation.
  • Desiccant agents added to the layers constituting blister strip package comprising dry powder formulation of the present invention are selected from silica gel, zeolite, alumina, bauxite, anhydrous calcium sulphate, activated carbon, hydrophilic chyles.
  • polymeric layers in the base and lid sheets of peelable blister strip package comprising said dry powder formulation are made of the same or different polymers. Thickness of these polymeric layers varies depending on the type and characteristics of the polymeric material used. Therefore, thickness of the polymeric layer varies in the range of 15-55 ⁇ , preferably in the range of 20-30 ⁇ according to the type of the polymeric material used.
  • the layer covering the inner surface of the cavity is a polymeric layer because of the fact that when the layer in contact with the dry powder formulation in the blister cavity is aluminium foil, some part of dry powder formulation adheres to the inner surface of the blister cavity due to porous structure of the aluminium foil and electrostatic forces and this causes uncontrolled dose inhalation.
  • Polymers constituting the polymeric layer can preferably be selected from thermoplastic polymers such as polyethylene, polypropylene, polystyrene, polyolefin, polyamide, polyvinyl chloride, polyurethane or synthetic polymers.
  • the drug composition in dry powder form described in the present invention comprising tiotropium and carmoterol and/or pharmaceutically acceptable derivatives thereof can be used in the treatment of many respiratory diseases particularly asthma, Chronic Obstructive Pulmonary Disease (COPD) and allergic rhinitis.
  • COPD Chronic Obstructive Pulmonary Disease
  • the drug composition of the present invention is used in the treatment of respiratory tract diseases comprising, but not limited to, allergic or non allergic asthma in every stage, acute lung injury (ALI), acute respiratory distress syndrome (ARDS), exacerbation of airways hyperactivity, chronic obstructive pulmonary disease including bronchiectasis, emphysema and chronic bronchitis; airways or lung diseases (COPD, COAD or COLD) pneumoconiosis, aluminosis, anthracosis, asbestosis, chalicosis, ptilosis, siderosis, silicosis, tabacosis and byssinosis.
  • This treatment may be prophylactic or symptomatic.
  • the composition of the present invention is particularly used in symptomatic treatment of asthma, allergic rhinitis and COPD.
  • EXAMPLE 1 Dry powder formulation suitable for a gelatin capsule used in capsule inhaler comprises 22 parts of tiotropium, 1 part of carmoterol; and 135 parts of fine grained lactose and 45 parts of coarse grained lactose as carrier, all of which are micronized in an air jet mill.
  • fine grained lactose and coarse grained lactose are stirred in a mixer after sieved separately. Tiotropium is added to this pre-mixture and mixed. Carmoterol is added into this new mixture and stirred again. The powder mixture obtained at the end of the process is sieved again and filled into capsules.
  • composition of the present invention can be explained with, but not limited to, these examples.
  • the example can be repeated by replacing the amounts used in example 1 with the amounts given in the table below.

Abstract

La présente invention concerne des formulations pharmaceutiques en poudre sèche comprenant du tiotropium et du carmotérol, utilisables dans des maladies des voies respiratoires.
PCT/TR2013/000031 2012-01-16 2013-01-16 Formulations en poudre sèche comprenant du tiotropium et du carmotérol WO2013109219A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP13720141.4A EP2804590A1 (fr) 2012-01-16 2013-01-16 Formulations en poudre sèche comprenant du tiotropium et du carmotérol

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR2012/00483 2012-01-16
TR201200483 2012-01-16

Publications (1)

Publication Number Publication Date
WO2013109219A1 true WO2013109219A1 (fr) 2013-07-25

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PCT/TR2013/000031 WO2013109219A1 (fr) 2012-01-16 2013-01-16 Formulations en poudre sèche comprenant du tiotropium et du carmotérol

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EP (1) EP2804590A1 (fr)
WO (1) WO2013109219A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017033032A1 (fr) * 2015-08-27 2017-03-02 Jagotec Ag Composition pharmaceutique à inhaler
EP3159278A1 (fr) * 2015-10-23 2017-04-26 Arven Ilac Sanayi Ve Ticaret A.S. Blister pour formulation pour inhalation à base de bromure de tiotropium
EP3159277A1 (fr) * 2015-10-23 2017-04-26 Arven Ilac Sanayi Ve Ticaret A.S. Blister pour formulation inhalable de bromure de tiotropium

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011093817A1 (fr) * 2010-01-29 2011-08-04 Mahmut Bilgic Compositions pharmaceutiques comprenant du tiotropium, du formotérol et du budésonide
WO2011093819A2 (fr) * 2010-01-28 2011-08-04 Mahmut Bilgic Nouvelle composition pharmaceutique combinée comprenant du tiotropium
WO2011093820A2 (fr) * 2010-01-28 2011-08-04 Mahmut Bilgic Composition pharmaceutique combinée comprenant du tiotropium
WO2011152804A2 (fr) * 2010-06-03 2011-12-08 Mahmut Bilgic Procédé pour formulations pulvérulentes sèches
WO2013009271A1 (fr) * 2011-06-02 2013-01-17 Mahmut Bilgic Nouvelle formulation améliorée de poudre sèche

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011093819A2 (fr) * 2010-01-28 2011-08-04 Mahmut Bilgic Nouvelle composition pharmaceutique combinée comprenant du tiotropium
WO2011093820A2 (fr) * 2010-01-28 2011-08-04 Mahmut Bilgic Composition pharmaceutique combinée comprenant du tiotropium
WO2011093817A1 (fr) * 2010-01-29 2011-08-04 Mahmut Bilgic Compositions pharmaceutiques comprenant du tiotropium, du formotérol et du budésonide
WO2011152804A2 (fr) * 2010-06-03 2011-12-08 Mahmut Bilgic Procédé pour formulations pulvérulentes sèches
WO2013009271A1 (fr) * 2011-06-02 2013-01-17 Mahmut Bilgic Nouvelle formulation améliorée de poudre sèche

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017033032A1 (fr) * 2015-08-27 2017-03-02 Jagotec Ag Composition pharmaceutique à inhaler
EP3159278A1 (fr) * 2015-10-23 2017-04-26 Arven Ilac Sanayi Ve Ticaret A.S. Blister pour formulation pour inhalation à base de bromure de tiotropium
EP3159277A1 (fr) * 2015-10-23 2017-04-26 Arven Ilac Sanayi Ve Ticaret A.S. Blister pour formulation inhalable de bromure de tiotropium
WO2017068108A1 (fr) * 2015-10-23 2017-04-27 Arven Ilac Sanayi Ve Ticaret A.S. Emballage-coque pour formulation inhalable de bromure de tiotropium
WO2017068119A1 (fr) * 2015-10-23 2017-04-27 Arven Ilac Sanayi Ve Ticaret A.S. Emballage-coque pour formulation inhalable de bromure de tiotropium
CN108137205A (zh) * 2015-10-23 2018-06-08 阿尔文伊莱克工贸有限公司 用于噻托溴铵的可吸入制剂的泡罩
EA034467B1 (ru) * 2015-10-23 2020-02-11 Арвен Иладж Санайи Ве Тиджарет А.Ш. Блистер для ингаляционного состава тиотропия бромида

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