EP2804585A1 - Formulations en poudre sèche comprenant du tiotropium, du formotérol et du budésonide - Google Patents

Formulations en poudre sèche comprenant du tiotropium, du formotérol et du budésonide

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Publication number
EP2804585A1
EP2804585A1 EP13720142.2A EP13720142A EP2804585A1 EP 2804585 A1 EP2804585 A1 EP 2804585A1 EP 13720142 A EP13720142 A EP 13720142A EP 2804585 A1 EP2804585 A1 EP 2804585A1
Authority
EP
European Patent Office
Prior art keywords
range
pharmaceutical formulation
formulation according
excipient
particle size
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP13720142.2A
Other languages
German (de)
English (en)
Inventor
Mahmut Bilgic
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of EP2804585A1 publication Critical patent/EP2804585A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/007—Pulmonary tract; Aromatherapy
    • A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/0075—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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin

Definitions

  • the present invention relates to pharmaceutical formulations in dry powder form comprising tiotropium, formoterol and budesonide 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 P2-adrenergic receptors and affect the muscles around the airways; alleviate or remove bronchospasm.
  • Salbutamol, levosalbutamol, procaterol, fenoterol, terbutaline, pirbuterol, metaproterenol ve bitolterol mesylate can be listed among short-acting ⁇ 2 agonists.
  • Long- acting ⁇ 2 agonists can be used more frequently in the treatment of patients suffering symptoms of asthma at nights and exercise-induced asthma.
  • Formoterol, salmeterol, bambuterol and clenbuterol are examples of long-acting ⁇ 2 agonists.
  • Corticostereoids which is another group of active agents used in the treatment of asthma and COPD, are synthetic and potent anti-inflammatory drugs similar to natural corticosteroid hormones secreted by adrenal glands. It is known that corticosteroids are quite effective drugs in asthma treatment. Budesonide, beclomethasone, flunisolide and fluticasone are among molecules belonging to this group.
  • Anticholinergics affect the muscles on bronchi including large airways. Like 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.
  • 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, formoterol and budesonide 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, formoterol and budesonide and/or pharmaceutically acceptable derivatives thereof.
  • dry powder formulations which comprise tiotropium, formoterol and budesonide having a ratio in the range of 0,5: 0.05:3 to 1 :3:45, preferably in the range of 1 :0.1 :2 to 1 :2:40 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 powder form comprising tiotropium, formoterol and budesonide and/or pharmaceutically acceptable derivatives thereof, characterized in that the ratio of tiotropium, formoterol and budesonide to each other respectively is in the range of 0,5: 0.05:3 to 1 :3:45, preferably in the range of 1 :0.1 :2 to 1 :2:40 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
  • 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.
  • formoterol 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 formoterol'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.
  • formoterol fumarate is used.
  • budesonide 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 budesonide' 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.
  • the inhalation formulation comprising tiotropium, formoterol and budesonide 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.
  • 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 subject of the present invention is pharmaceutical formulations in dry powder form comprising tiotropium, formoterol and budesonide and/or pharmaceutically acceptable derivatives thereof, characterized in that
  • the ratio of tiotropium, formoterol and budesonide to each other respectively is in the range of 0,5 : 0.05 :3 to 1 :3 :45, preferably in the range of 1 :0.1 :2 to 1 :2:40 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, formoterol and budesonide and/or pharmaceutically acceptable derivatives thereof, characterized in that the ratio of tiotropium, formoterol and budesonide to each other respectively is in the range of 0,5: 0.05:3 to 1 :3:45, preferably in the range of 1 :0.1 :2 to 1 :2:40 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, formoterol and budesonide and/or pharmaceutically acceptable derivatives thereof is composed of the following steps: I. micronizing tiotropium, formoterol and budesonide so as to bring them to the desired particle size,
  • the present invention relates to inhalation of the dry powder formulations comprising tiotropium, formoterol and budesonide 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, formoterol and budesonide 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, formoterol and budesonide 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, formoterol and budesonide 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 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, formoterol and budesonide and/or pharmaceutically acceptable derivatives thereof is in the range of 18-30 mm , preferably in the range of 20 - 25 mm , more, preferably in the range of 21 -24 mm .
  • 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, formoterol and budesonide and/or pharmaceutically acceptable derivatives thereof is 18-30 mm , 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, formoterol and budesonide 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.
  • 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, foraioterol and budesonide 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.
  • Dry powder formulation suitable for a gelatin capsule used in capsule inhaler comprises 1 part of tiotropium, 0.2 part of foraioterol fumarate, 20 parts of budesonide; and 275 parts of fine grained lactose and 9.5 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, foraioterol and budesonide are added to this mixture one by one, sieved again and mixed.
  • the powder mixture obtained at the end of the process is filled into capsules.
  • composition of the present invention can be explained with, but not limited to, these examples.

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

Abstract

La présente invention concerne des formulations pharmaceutiques en poudre sèche comprenant du tiotropium, du formotérol et du budésonide, utilisables dans des maladies des voies respiratoires.
EP13720142.2A 2012-01-16 2013-01-16 Formulations en poudre sèche comprenant du tiotropium, du formotérol et du budésonide Withdrawn EP2804585A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR201200482 2012-01-16
PCT/TR2013/000032 WO2013109220A1 (fr) 2012-01-16 2013-01-16 Formulations en poudre sèche comprenant du tiotropium, du formotérol et du budésonide

Publications (1)

Publication Number Publication Date
EP2804585A1 true EP2804585A1 (fr) 2014-11-26

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Application Number Title Priority Date Filing Date
EP13720142.2A Withdrawn EP2804585A1 (fr) 2012-01-16 2013-01-16 Formulations en poudre sèche comprenant du tiotropium, du formotérol et du budésonide

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EP (1) EP2804585A1 (fr)
WO (1) WO2013109220A1 (fr)

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JP6684275B2 (ja) 2014-10-08 2020-04-22 ザンボン ソシエタ ペル アチオニ ブデソニド及びホルモテロールを含有する医薬組成物
WO2016055544A1 (fr) * 2014-10-08 2016-04-14 Eratech S.R.L. Composition comprenant au moins une poudre sèche obtenue par séchage par pulvérisation pour augmenter la stabilité de la formulation
GB201515310D0 (en) * 2015-08-27 2015-10-14 Jagotec Ag Pharmaceutical composition

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Publication number Priority date Publication date Assignee Title
WO2004019985A1 (fr) * 2002-08-29 2004-03-11 Cipla Ltd Produits et compositions pharmaceutiques comprenant des agents anticholinergiques specifiques, des agonistes beta-2 et des corticosteroides
EP2124915A2 (fr) * 2007-02-19 2009-12-02 Cipla Limited Combinaisons pharmaceutiques
TR201000680A2 (tr) * 2010-01-29 2011-08-22 B�Lg�� Mahmut Tiotropyum, formoterol ve budesonid içeren farmasötik bileşimler
WO2011093812A2 (fr) * 2010-01-28 2011-08-04 Mahmut Bilgic Formulation pharmaceutique comprenant du tiotropium et du budésonide sous forme de poudre sèche

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Title
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Also Published As

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