CA2477885A1 - Pressurised metered dose inhalers containing solutions of beta-2 agonists - Google Patents
Pressurised metered dose inhalers containing solutions of beta-2 agonists Download PDFInfo
- Publication number
- CA2477885A1 CA2477885A1 CA002477885A CA2477885A CA2477885A1 CA 2477885 A1 CA2477885 A1 CA 2477885A1 CA 002477885 A CA002477885 A CA 002477885A CA 2477885 A CA2477885 A CA 2477885A CA 2477885 A1 CA2477885 A1 CA 2477885A1
- Authority
- CA
- Canada
- Prior art keywords
- pharmaceutical formulation
- formulation according
- hydroxy
- active ingredient
- hfa
- 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.)
- Granted
Links
- 229940124748 beta 2 agonist Drugs 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 18
- 238000009472 formulation Methods 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims abstract 5
- 238000000034 method Methods 0.000 claims abstract 4
- 239000000556 agonist Substances 0.000 claims abstract 2
- SYCWERNQGSKYAG-QVRIGTRMSA-N hydron;8-hydroxy-5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]-1h-quinolin-2-one;chloride Chemical compound Cl.C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 SYCWERNQGSKYAG-QVRIGTRMSA-N 0.000 claims abstract 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000004480 active ingredient Substances 0.000 claims 7
- 150000005828 hydrofluoroalkanes Chemical class 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- 239000011248 coating agent Substances 0.000 claims 3
- 238000000576 coating method Methods 0.000 claims 3
- 239000006184 cosolvent Substances 0.000 claims 3
- 239000003380 propellant Substances 0.000 claims 3
- 239000004812 Fluorinated ethylene propylene Substances 0.000 claims 2
- 239000004695 Polyether sulfone Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 229920009441 perflouroethylene propylene Polymers 0.000 claims 2
- 229920006393 polyether sulfone Polymers 0.000 claims 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 claims 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims 1
- IHOXNOQMRZISPV-YJYMSZOUSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-methoxyphenyl)propan-2-yl]azaniumyl]ethyl]-2-oxo-1h-quinolin-8-olate Chemical group C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 IHOXNOQMRZISPV-YJYMSZOUSA-N 0.000 claims 1
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 claims 1
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims 1
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 claims 1
- LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 claims 1
- 239000004813 Perfluoroalkoxy alkane Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 230000001078 anti-cholinergic effect Effects 0.000 claims 1
- 229950000210 beclometasone dipropionate Drugs 0.000 claims 1
- 229960004436 budesonide Drugs 0.000 claims 1
- 229960003728 ciclesonide Drugs 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 238000002788 crimping Methods 0.000 claims 1
- 229960000289 fluticasone propionate Drugs 0.000 claims 1
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229960001361 ipratropium bromide Drugs 0.000 claims 1
- KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229960001609 oxitropium bromide Drugs 0.000 claims 1
- LCELQERNWLBPSY-KHSTUMNDSA-M oxitropium bromide Chemical compound [Br-].C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)CC)=CC=CC=C1 LCELQERNWLBPSY-KHSTUMNDSA-M 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 229920011301 perfluoro alkoxyl alkane Polymers 0.000 claims 1
- 239000008249 pharmaceutical aerosol Substances 0.000 claims 1
- 239000005011 phenolic resin Substances 0.000 claims 1
- 229920001515 polyalkylene glycol Polymers 0.000 claims 1
- 229920005862 polyol Polymers 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- -1 polytetrafluoroethylene Polymers 0.000 claims 1
- 239000004810 polytetrafluoroethylene Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 229960000257 tiotropium bromide Drugs 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 210000004072 lung Anatomy 0.000 abstract 1
- 230000035515 penetration Effects 0.000 abstract 1
- 208000023504 respiratory system disease Diseases 0.000 abstract 1
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
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
-
- 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
-
- 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
- A61K31/47—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
- 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
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Dispersion Chemistry (AREA)
- Otolaryngology (AREA)
- Pain & Pain Management (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
Abstract
The present invention relates to a pharmaceutical formulation for use in the administration of 2(1H)-quinolinone derivatives long-acting .beta.2-agonists by inhalation. In particular this invention relates to a chemically stable highly efficient TA 2005 HFA solution formulation to be administered by pressurised metered dose inhalers (pMDIs) characterized by a deep lung penetration. The invention also relates to methods for the preparation of said formulation and to its use in respiratory diseases such as asthma and chronic obstructive pulmonary disease (COPD).
Claims (19)
1. A pharmaceutical aerosol formulation to be administered by pressurized metered dose inhalers which comprises an active ingredient selected from a
2(1H)-quinolinone derivative long acting .beta.2- agonist of formula:
where R1 is methyl and R2 is hydrogen or R1 and R2 form a methylene bridge (CH2)n n is 1 or 2 R3, R4, R5 and R6 are each independently hydrogen, hydroxy, C1-C4 straight chain or branched alkyl, C1-C4 straight chain or branched alkyl substituted by one or more halogen and/or hydroxy, halogen, C1-C4 straight chain or branched alkoxy, a stereoisomer, physiologically acceptable salt and solvate thereof, in a solution of a liquefied HFA propellant, a co-solvent, and optionally an amount of water up to 5% on the total weight of the formulation.
2. A pharmaceutical formulation according to claim 1 wherein the fraction of particles equal or less than 1.1 µm delivered on actuation of the inhaler is higher or equal than 30% as defined by the content of the stages S6-AF of an Andersen Cascade Impactor, relatively to the content of the stages S3-AF, according to the method referred to in the description on page 16 lines 10 to 18.
where R1 is methyl and R2 is hydrogen or R1 and R2 form a methylene bridge (CH2)n n is 1 or 2 R3, R4, R5 and R6 are each independently hydrogen, hydroxy, C1-C4 straight chain or branched alkyl, C1-C4 straight chain or branched alkyl substituted by one or more halogen and/or hydroxy, halogen, C1-C4 straight chain or branched alkoxy, a stereoisomer, physiologically acceptable salt and solvate thereof, in a solution of a liquefied HFA propellant, a co-solvent, and optionally an amount of water up to 5% on the total weight of the formulation.
2. A pharmaceutical formulation according to claim 1 wherein the fraction of particles equal or less than 1.1 µm delivered on actuation of the inhaler is higher or equal than 30% as defined by the content of the stages S6-AF of an Andersen Cascade Impactor, relatively to the content of the stages S3-AF, according to the method referred to in the description on page 16 lines 10 to 18.
3. A pharmaceutical formulation according to claims 1-2 wherein the superfine fraction is higher than 50%.
4. A pharmaceutical formulation according to claims 1-3 wherein the active ingredient is 8-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxy-phenyl)-1-methylethyl]amino]ethyl]-2(1H)-quinolinone, a physiologically acceptable salt or a solvate thereof.
5. A pharmaceutical formulation according to claims 1-3 wherein the active ingredient is 8-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxy-phenyl)-1-methylethyl]amino]ethyl]-2(1H)-quinolinone hydrochloride.
6. A pharmaceutical formulation according to claim 5 wherein the active ingredient is in a concentration comprised between 0.0005 and 0.024% w/v.
7. A pharmaceutical formulation according to claim 5 wherein the active ingredient is in a concentration comprised between 0.001 and 0.008% w/v.
8. A pharmaceutical formulation according to any preceding claim wherein the pH is comprised between 2.5 and 5Ø
9. A pharmaceutical formulation according to any preceding claim wherein the pH is comprised between 2.8 and 4Ø
10. A pharmaceutical formulation according to claims 8 and 9 wherein the pH is adjusted by adding hydrochloric acid.
11. A pharmaceutical formulation according to any preceding claim, wherein the propellant includes one or more hydrofluoroalkanes [HFAs]
selected from the group comprising HFA 134a and HFA 227.
selected from the group comprising HFA 134a and HFA 227.
12. A pharmaceutical formulation according to any preceding claim, wherein the co-solvent is selected from the group of lower alkyl (C1-C4) alcohols, polyols, polyalkylene glycols, (poly)alkoxy derivatives and their combinations.
13. A pharmaceutical formulation according to claim 12 wherein the co-solvent is ethanol.
14. A pharmaceutical formulation according to claim 6 further comprising
15% w/w ethanol, from 0.01% to 0.05% w/w HCl 0.1 M and HFA 134 a.
15. A pharmaceutical formulation according to any preceding claim filled in a canister having part or all of its internal metallic surfaces lined with an inert organic coating.
15. A pharmaceutical formulation according to any preceding claim filled in a canister having part or all of its internal metallic surfaces lined with an inert organic coating.
16. A pharmaceutical formulation according to claim 15, wherein the canister is lined with an inert organic coating selected from epoxy-phenol resins, perfluoroalkoxyalkane, perfluoroalkoxyalkylene, perfluoroalkylenes such as polytetrafluoroethylene, fluorinated-ethylene-propylene, polyether sulfone and a copolymer fluorinated-ethylene-propylene polyether sulfone.
17. A pharmaceutical formulation according to claim 16 wherein the inert organic coating is polytetrafluoroethylene (Teflon).
18. A pharmaceutical formulation according to any preceding claim further comprising a further active ingredient selected from the class of steroids such as beclomethasone dipropionate, fluticasone propionate, ciclesonide, budesonide and its 22R-epimer or anticholinergic atropine-like derivatives such as ipratropium bromide, oxitropium bromide and tiotropium bromide.
19. A method of preparing the formulations of claims 1-18, the method comprising:
(a) preparing of a solution of one or more active ingredients in one or more co-solvents;
(b) optionally adding a pre-determined amount of water and/or adjusting the pH of the solution;
(c) filling of the device with said solution;
(d) crimping with valves and gassing;
(e) adding a propellant containing a hydrofluoroalkane (HFA).
(a) preparing of a solution of one or more active ingredients in one or more co-solvents;
(b) optionally adding a pre-determined amount of water and/or adjusting the pH of the solution;
(c) filling of the device with said solution;
(d) crimping with valves and gassing;
(e) adding a propellant containing a hydrofluoroalkane (HFA).
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02004786.6 | 2002-03-01 | ||
| EP02004786A EP1340492A1 (en) | 2002-03-01 | 2002-03-01 | Aerosol formulations for pulmonary administration of medicaments having systemic effects |
| EP02023589A EP1415647A1 (en) | 2002-10-23 | 2002-10-23 | "Long-acting beta-2 agonists ultrafine formulations" |
| EP02023589.1 | 2002-10-23 | ||
| PCT/EP2003/002004 WO2003074025A2 (en) | 2002-03-01 | 2003-02-27 | Pressurised metered dose inhalers containing solutions of beta-2 agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2477885A1 true CA2477885A1 (en) | 2003-09-12 |
| CA2477885C CA2477885C (en) | 2010-12-21 |
Family
ID=27790093
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2477881A Expired - Lifetime CA2477881C (en) | 2002-03-01 | 2003-02-26 | Formoterol superfine formulation |
| CA2477885A Expired - Fee Related CA2477885C (en) | 2002-03-01 | 2003-02-27 | Pressurised metered dose inhalers containing solutions of beta-2 agonists |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2477881A Expired - Lifetime CA2477881C (en) | 2002-03-01 | 2003-02-26 | Formoterol superfine formulation |
Country Status (36)
| Country | Link |
|---|---|
| US (4) | US20050152846A1 (en) |
| EP (6) | EP1480615B1 (en) |
| JP (3) | JP2005523905A (en) |
| KR (2) | KR100947409B1 (en) |
| CN (2) | CN100398094C (en) |
| AR (2) | AR038641A1 (en) |
| AT (1) | ATE465712T1 (en) |
| AU (2) | AU2003222753B2 (en) |
| BR (2) | BRPI0308274B8 (en) |
| CA (2) | CA2477881C (en) |
| CO (2) | CO5611092A2 (en) |
| CY (4) | CY1111133T1 (en) |
| DE (1) | DE60332321D1 (en) |
| DK (4) | DK1480615T3 (en) |
| EA (2) | EA007735B1 (en) |
| ES (4) | ES2342463T3 (en) |
| GE (2) | GEP20063986B (en) |
| HK (1) | HK1079425A1 (en) |
| HR (2) | HRP20040752B1 (en) |
| HU (3) | HUE044926T2 (en) |
| IL (3) | IL163843A0 (en) |
| LT (3) | LT3384931T (en) |
| MA (1) | MA27175A1 (en) |
| ME (3) | ME00077B (en) |
| MX (2) | MXPA04008372A (en) |
| MY (2) | MY143517A (en) |
| NO (2) | NO20043625L (en) |
| NZ (2) | NZ535018A (en) |
| PE (2) | PE20030824A1 (en) |
| PL (2) | PL209212B1 (en) |
| PT (4) | PT3494995T (en) |
| RS (2) | RS52387B (en) |
| SI (4) | SI3536344T1 (en) |
| TN (2) | TNSN04147A1 (en) |
| TW (2) | TW200303752A (en) |
| WO (2) | WO2003074024A1 (en) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20010031244A1 (en) * | 1997-06-13 | 2001-10-18 | Chiesi Farmaceutici S.P.A. | Pharmaceutical aerosol composition |
| DZ2947A1 (en) * | 1998-11-25 | 2004-03-15 | Chiesi Farma Spa | Pressure metered dose inhaler. |
| IT1303788B1 (en) * | 1998-11-25 | 2001-02-23 | Chiesi Farma Spa | MEDICINAL AEROSOL FORMULATIONS. |
| US6315985B1 (en) * | 1999-06-18 | 2001-11-13 | 3M Innovative Properties Company | C-17/21 OH 20-ketosteroid solution aerosol products with enhanced chemical stability |
| ES2165768B1 (en) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | NEW DERIVATIVES OF QUINUCLIDINE AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM. |
| IT1317720B1 (en) * | 2000-01-07 | 2003-07-15 | Chiesi Farma Spa | DEVICE FOR THE ADMINISTRATION OF AEROSOL DOSED PRESSURIZED INPROPELLENT HYDROFLUOROALKANS. |
| IT1318514B1 (en) * | 2000-05-12 | 2003-08-27 | Chiesi Farma Spa | FORMULATIONS CONTAINING A GLUCOCORTICOSTEROID DRUG FOR THE TREATMENT OF BRONCOPOLMONARY DISEASES. |
| US20060257324A1 (en) * | 2000-05-22 | 2006-11-16 | Chiesi Farmaceutici S.P.A. | Pharmaceutical solution formulations for pressurised metered dose inhalers |
| ME00220B (en) * | 2000-05-22 | 2010-10-10 | Chiesi Farm Spa | Stable pharmaceutical solution formulations for pressurised metered dose inhalers |
| CZ301676B6 (en) * | 2001-03-30 | 2010-05-19 | Jagotec Ag | Pharmaceutical suspension aerosol formulation for inhalation and use of carboxylic acid salt |
| TR200401980T4 (en) * | 2001-07-02 | 2004-09-21 | Chiesi Farmaceutici S.P.A. | Tobramycin formulation optimized for aerosol administration |
| EP1340492A1 (en) * | 2002-03-01 | 2003-09-03 | CHIESI FARMACEUTICI S.p.A. | Aerosol formulations for pulmonary administration of medicaments having systemic effects |
| PT3494995T (en) * | 2002-03-01 | 2020-03-30 | Chiesi Farm Spa | Formoterol superfine formulation |
| EP1415647A1 (en) * | 2002-10-23 | 2004-05-06 | CHIESI FARMACEUTICI S.p.A. | "Long-acting beta-2 agonists ultrafine formulations" |
| EP1452179A1 (en) * | 2003-02-27 | 2004-09-01 | CHIESI FARMACEUTICI S.p.A. | Novel medicament combination of a highly potent long-lasting beta2-agonist and a corticosteroid |
| CA2534120C (en) * | 2003-07-31 | 2012-09-11 | Boehringer Ingelheim International Gmbh | Medicaments for inhalation comprising anticholinergics and a betamimetic |
| GB0323684D0 (en) * | 2003-10-09 | 2003-11-12 | Jagotec Ag | Improvements in or relating to organic compounds |
| GB0323685D0 (en) * | 2003-10-09 | 2003-11-12 | Jagotec Ag | Improvements in or relating to organic compounds |
| EP1595531A1 (en) * | 2004-05-13 | 2005-11-16 | CHIESI FARMACEUTICI S.p.A. | Stable pharmaceutical solution formulations for pressurized metered dose inhalers |
| KR20070000476A (en) * | 2004-02-27 | 2007-01-02 | 키에시 파르마슈티시 엣스. 피. 에이. | Stable pharmaceutical solution formulations for pressurized metered dose inhalers |
| UA88894C2 (en) * | 2004-02-27 | 2009-12-10 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Stable pharmaceutical solution formulation for pressurized metered dose inhalers |
| MXPA06013189A (en) * | 2004-05-13 | 2007-02-14 | Chiesi Farma Spa | Medicinal aerosol formulation products with improved chemical stability. |
| JP5209963B2 (en) * | 2004-07-02 | 2013-06-12 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Aerosol suspension formulation containing TG227EA or TG134A as propellant |
| GB0420722D0 (en) * | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| GEP20105040B (en) * | 2005-02-25 | 2010-07-12 | Chiesi Farm Spa | Pharmaceutical aerosol formulations for pressurized metered dose inhalers comprising a sequestering agent |
| DE102006017320A1 (en) * | 2006-04-11 | 2007-10-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Aerosol suspension formulations with TG 227 ea or TG 134 a as propellant |
| EP1982709A1 (en) | 2007-04-19 | 2008-10-22 | CHIESI FARMACEUTICI S.p.A. | Use of a composition comprising formoterol and beclomethasone dipropionate for the prevention or treatment of an acute condition of asthma |
| EP2100599A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2100598A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| GB2461752B (en) * | 2008-07-14 | 2013-04-17 | Neo Inhalation Products Ltd | Metered dose inhaler |
| CA2741078A1 (en) * | 2008-10-23 | 2010-04-29 | Sunovion Pharmaceuticals Inc. | Arformoterol and tiotropium compositions and methods for use |
| GB0918149D0 (en) | 2009-10-16 | 2009-12-02 | Jagotec Ag | Improved medicinal aerosol formulation |
| GEP20156311B (en) | 2009-12-23 | 2015-07-10 | Chiesi Farma Spa | Combination therapy for copd |
| UA106098C2 (en) | 2009-12-23 | 2014-07-25 | К'Єзі Фармачеутічі С.П.А. | Normal;heading 1;heading 2;heading 3;AEROSOL FORMULATION FOR COPD |
| EP2360147A1 (en) * | 2010-02-22 | 2011-08-24 | CHIESI FARMACEUTICI S.p.A. | Process for preparing crystalline particles of a salt of 8-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino] ethyl]-2(1H)-quinolinone (carmoterol) |
| WO2012007729A2 (en) * | 2010-07-16 | 2012-01-19 | Cipla Limited | Pharmaceutical compositions |
| TWI399202B (en) | 2011-03-17 | 2013-06-21 | Intech Biopharm Ltd | The preparation for formulation composition and manufacturing processes of metered dose inhalers treated respiratory diseases |
| EP2510928A1 (en) | 2011-04-15 | 2012-10-17 | Almirall, S.A. | Aclidinium for use in improving the quality of sleep in respiratory patients |
| EP2919649B1 (en) * | 2012-11-15 | 2021-12-22 | JP Respiratory Technology AB | Device and method for pulmonary function measurement |
| RU2504402C1 (en) * | 2012-11-20 | 2014-01-20 | Шолекс Девелопмент Гмбх | Inhalation formulation in form of aerosol for treating bronchial asthma and chronic obstructive pulmonary disease |
| CN106667973A (en) * | 2017-01-22 | 2017-05-17 | 西咸新区世云工研坊生物科技有限公司 | Composition for preventing haze damage and preparation method and spray of composition |
| WO2021151857A1 (en) | 2020-01-28 | 2021-08-05 | Chiesi Farmaceutici S.P.A. | Pressurised metered dose inhalers comprising a buffered pharmaceutical formulation |
| KR20220144361A (en) | 2020-02-20 | 2022-10-26 | 키에시 파르마슈티시 엣스. 피. 에이. | A pressurized metered dose inhaler containing a buffered pharmaceutical formulation |
| WO2023227783A1 (en) | 2022-05-27 | 2023-11-30 | Chiesi Farmaceutici S.P.A. | A pharmaceutical formulation for pressurised metered dose inhaler |
Family Cites Families (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3361306A (en) * | 1966-03-31 | 1968-01-02 | Merck & Co Inc | Aerosol unit dispensing uniform amounts of a medically active ingredient |
| US3622053A (en) * | 1969-12-10 | 1971-11-23 | Schering Corp | Aerosol inhaler with flip-up nozzle |
| US4185100A (en) * | 1976-05-13 | 1980-01-22 | Johnson & Johnson | Topical anti-inflammatory drug therapy |
| US4499108A (en) * | 1983-06-08 | 1985-02-12 | Schering Corporation | Stable pleasant-tasting albuterol sulfate pharmaceutical formulations |
| GB8334494D0 (en) * | 1983-12-24 | 1984-02-01 | Tanabe Seiyaku Co | Carbostyril derivatives |
| IT1196142B (en) * | 1984-06-11 | 1988-11-10 | Sicor Spa | PROCEDURE FOR THE PREPARATION OF 16.17-ACETALS OF PREGNANIC DERIVATIVES AND NEW COMPOUNDS OBTAINED |
| US4584320A (en) * | 1985-01-03 | 1986-04-22 | David Rubin | Anti-asthmatic composition and method using 8,11,14,17-eicosatetraenoic acid |
| US5192528A (en) * | 1985-05-22 | 1993-03-09 | Liposome Technology, Inc. | Corticosteroid inhalation treatment method |
| US5225183A (en) * | 1988-12-06 | 1993-07-06 | Riker Laboratories, Inc. | Medicinal aerosol formulations |
| IT1244441B (en) * | 1990-09-13 | 1994-07-15 | Chiesi Farma Spa | MOUTH INHALATION DEVICE FOR AEROSOL DRUGS |
| US6006745A (en) * | 1990-12-21 | 1999-12-28 | Minnesota Mining And Manufacturing Company | Device for delivering an aerosol |
| US5190029A (en) * | 1991-02-14 | 1993-03-02 | Virginia Commonwealth University | Formulation for delivery of drugs by metered dose inhalers with reduced or no chlorofluorocarbon content |
| US6299863B1 (en) * | 1992-04-03 | 2001-10-09 | Sepracor Inc. | Aerosol formulations containing micronized optically pure (R,R) formoterol for bronchodilating therapy |
| EP0601036B1 (en) * | 1991-08-29 | 1999-04-28 | Broncho-Air Medizintechnik AG | Medical device for inhalating doses of spray |
| DE4230876A1 (en) * | 1992-03-17 | 1993-09-23 | Asta Medica Ag | COMPRESSED GAS PACKS USING POLYOXYETHYLENE GLYCERYL OLEATES |
| AU6048694A (en) * | 1992-12-09 | 1994-07-04 | Paul D. Jager | Stabilized medicinal aerosol solution formulations |
| ZA939195B (en) * | 1992-12-09 | 1995-06-08 | Boehringer Ingelheim Pharma | Stabilized medicinal aerosol solution formulations |
| SE9203743D0 (en) * | 1992-12-11 | 1992-12-11 | Astra Ab | EFFICIENT USE |
| US5899201A (en) * | 1993-05-26 | 1999-05-04 | Minnesota Mining And Manufacturing Company | Aerosol actuator |
| EP0735884B1 (en) * | 1993-12-20 | 2000-04-26 | Minnesota Mining And Manufacturing Company | Flunisolide aerosol formulations |
| US5508269A (en) * | 1994-10-19 | 1996-04-16 | Pathogenesis Corporation | Aminoglycoside formulation for aerosolization |
| US5653961A (en) * | 1995-03-31 | 1997-08-05 | Minnesota Mining And Manufacturing Company | Butixocort aerosol formulations in hydrofluorocarbon propellant |
| EP1166811B1 (en) * | 1995-04-14 | 2006-12-06 | SmithKline Beecham Corporation | Metered dose inhaler for fluticasone propionate |
| DK0820279T3 (en) * | 1995-04-14 | 2002-10-07 | Smithkline Beecham Corp | Dosing metered inhaler for Albuterol |
| US5637505A (en) * | 1995-05-19 | 1997-06-10 | Chiron Diagnostics Corporation | Method to prepare dye-based reference material |
| CN1232389A (en) * | 1996-10-04 | 1999-10-20 | 崎玉第一制药株式会社 | Patch |
| US6040344A (en) * | 1996-11-11 | 2000-03-21 | Sepracor Inc. | Formoterol process |
| US6413496B1 (en) * | 1996-12-04 | 2002-07-02 | Biogland Ireland (R&D) Limited | Pharmaceutical compositions and devices for their administration |
| DK1014943T3 (en) | 1997-02-05 | 2002-10-14 | Jago Res Ag | Medical aerosol formulations |
| US6126919A (en) | 1997-02-07 | 2000-10-03 | 3M Innovative Properties Company | Biocompatible compounds for pharmaceutical drug delivery systems |
| US5891419A (en) * | 1997-04-21 | 1999-04-06 | Aeropharm Technology Limited | Environmentally safe flunisolide aerosol formulations for oral inhalation |
| US6188933B1 (en) * | 1997-05-12 | 2001-02-13 | Light & Sound Design Ltd. | Electronically controlled stage lighting system |
| GB2326334A (en) | 1997-06-13 | 1998-12-23 | Chiesi Farma Spa | Pharmaceutical aerosol compositions |
| US20010031244A1 (en) * | 1997-06-13 | 2001-10-18 | Chiesi Farmaceutici S.P.A. | Pharmaceutical aerosol composition |
| US5954047A (en) * | 1997-10-17 | 1999-09-21 | Systemic Pulmonary Development, Ltd. | Methods and apparatus for delivering aerosolized medication |
| US6086376A (en) * | 1998-01-30 | 2000-07-11 | Rtp Pharma Inc. | Dry aerosol suspension of phospholipid-stabilized drug microparticles in a hydrofluoroalkane propellant |
| US6045784A (en) * | 1998-05-07 | 2000-04-04 | The Procter & Gamble Company | Aerosol package compositions containing fluorinated hydrocarbon propellants |
| US6451285B2 (en) * | 1998-06-19 | 2002-09-17 | Baker Norton Pharmaceuticals, Inc. | Suspension aerosol formulations containing formoterol fumarate and a fluoroalkane propellant |
| NZ509328A (en) | 1998-07-24 | 2002-11-26 | Jago Res A | Medicinal aerosol formulations |
| ES2193726T3 (en) * | 1998-08-04 | 2003-11-01 | Jago Res Ag | MEDICINAL AEROSOL FORMULATIONS. |
| DE19847969A1 (en) * | 1998-10-17 | 2000-04-20 | Boehringer Ingelheim Pharma | Stable liquid formulation of formoterol in solution or suspension medium, used after dilution for treatment of asthma by inhalation |
| US7521068B2 (en) | 1998-11-12 | 2009-04-21 | Elan Pharma International Ltd. | Dry powder aerosols of nanoparticulate drugs |
| DK1283036T3 (en) * | 1998-11-13 | 2008-03-25 | Jagotec Ag | Dry powder for inhalation |
| IT1303788B1 (en) * | 1998-11-25 | 2001-02-23 | Chiesi Farma Spa | MEDICINAL AEROSOL FORMULATIONS. |
| DZ2947A1 (en) * | 1998-11-25 | 2004-03-15 | Chiesi Farma Spa | Pressure metered dose inhaler. |
| US6004537A (en) * | 1998-12-18 | 1999-12-21 | Baker Norton Pharmaceuticals, Inc. | Pharmaceutical solution aerosol formulations containing fluoroalkanes, budesonide and formoterol |
| US6290930B1 (en) * | 1998-12-18 | 2001-09-18 | Baker Norton Pharmaceuticals, Inc. | Pharmaceutical solution aerosol formulations containing fluoroalkanes and budesonide |
| US6352152B1 (en) * | 1998-12-18 | 2002-03-05 | Smithkline Beecham Corporation | Method and package for storing a pressurized container containing a drug |
| GB9904919D0 (en) * | 1999-03-03 | 1999-04-28 | Novartis Ag | Organic compounds |
| US6315985B1 (en) * | 1999-06-18 | 2001-11-13 | 3M Innovative Properties Company | C-17/21 OH 20-ketosteroid solution aerosol products with enhanced chemical stability |
| DE60031504T2 (en) * | 1999-09-11 | 2007-04-05 | Glaxo Group Ltd., Greenford | FLUTICASONPROPIONATE DRUG PREPARATION |
| GB9928311D0 (en) * | 1999-11-30 | 2000-01-26 | Novartis Ag | Organic compounds |
| US6578125B2 (en) | 2000-02-14 | 2003-06-10 | Sanyo Electric Co., Ltd. | Memory access circuit and memory access control circuit |
| IT1317846B1 (en) * | 2000-02-22 | 2003-07-15 | Chiesi Farma Spa | FORMULATIONS CONTAINING AN ANTICOLINERGIC DRUG FOR THE TREATMENT OF CHRONIC OBSTRUCTIVE BRONCOPNEUMOPATHY. |
| GB0008660D0 (en) * | 2000-04-07 | 2000-05-31 | Arakis Ltd | The treatment of respiratory diseases |
| GB0009773D0 (en) | 2000-04-19 | 2000-06-07 | Univ Cardiff | Particulate composition |
| IT1318514B1 (en) * | 2000-05-12 | 2003-08-27 | Chiesi Farma Spa | FORMULATIONS CONTAINING A GLUCOCORTICOSTEROID DRUG FOR THE TREATMENT OF BRONCOPOLMONARY DISEASES. |
| ME00220B (en) * | 2000-05-22 | 2010-10-10 | Chiesi Farm Spa | Stable pharmaceutical solution formulations for pressurised metered dose inhalers |
| EP1241113A1 (en) | 2001-03-12 | 2002-09-18 | CHIESI FARMACEUTICI S.p.A. | Inhaler with means for improving chemical stability of medicinal aerosol solution contained therein |
| TR200401980T4 (en) * | 2001-07-02 | 2004-09-21 | Chiesi Farmaceutici S.P.A. | Tobramycin formulation optimized for aerosol administration |
| PT3494995T (en) * | 2002-03-01 | 2020-03-30 | Chiesi Farm Spa | Formoterol superfine formulation |
| EP1340492A1 (en) * | 2002-03-01 | 2003-09-03 | CHIESI FARMACEUTICI S.p.A. | Aerosol formulations for pulmonary administration of medicaments having systemic effects |
| EP1595531A1 (en) * | 2004-05-13 | 2005-11-16 | CHIESI FARMACEUTICI S.p.A. | Stable pharmaceutical solution formulations for pressurized metered dose inhalers |
-
2003
- 2003-02-26 PT PT191663244T patent/PT3494995T/en unknown
- 2003-02-26 SI SI200332607T patent/SI3536344T1/en unknown
- 2003-02-26 DK DK03718677.2T patent/DK1480615T3/en active
- 2003-02-26 KR KR1020047013491A patent/KR100947409B1/en active IP Right Grant
- 2003-02-26 EP EP03718677A patent/EP1480615B1/en not_active Expired - Lifetime
- 2003-02-26 PT PT03718677T patent/PT1480615E/en unknown
- 2003-02-26 HU HUE18173392 patent/HUE044926T2/en unknown
- 2003-02-26 CA CA2477881A patent/CA2477881C/en not_active Expired - Lifetime
- 2003-02-26 EP EP19166324.4A patent/EP3494995B1/en not_active Expired - Lifetime
- 2003-02-26 MX MXPA04008372A patent/MXPA04008372A/en active IP Right Grant
- 2003-02-26 DK DK19166324.4T patent/DK3494995T3/en active
- 2003-02-26 IL IL16384303A patent/IL163843A0/en unknown
- 2003-02-26 LT LTEP18173392.4T patent/LT3384931T/en unknown
- 2003-02-26 DK DK19171326.2T patent/DK3536344T3/en active
- 2003-02-26 BR BRPI0308274A patent/BRPI0308274B8/en active IP Right Grant
- 2003-02-26 ES ES03718677T patent/ES2342463T3/en not_active Expired - Lifetime
- 2003-02-26 LT LTEP19171326.2T patent/LT3536344T/en unknown
- 2003-02-26 HU HUE19166324A patent/HUE049426T2/en unknown
- 2003-02-26 GE GEAP8391A patent/GEP20063986B/en unknown
- 2003-02-26 SI SI200331813T patent/SI1480615T1/en unknown
- 2003-02-26 ES ES19166324T patent/ES2780127T3/en not_active Expired - Lifetime
- 2003-02-26 HU HUE19171326A patent/HUE048310T2/en unknown
- 2003-02-26 ME MEP-2008-301A patent/ME00077B/en unknown
- 2003-02-26 WO PCT/EP2003/001964 patent/WO2003074024A1/en active Application Filing
- 2003-02-26 EP EP10156461.5A patent/EP2201964B1/en not_active Expired - Lifetime
- 2003-02-26 ES ES19171326T patent/ES2779273T3/en not_active Expired - Lifetime
- 2003-02-26 AU AU2003222753A patent/AU2003222753B2/en not_active Expired
- 2003-02-26 DE DE60332321T patent/DE60332321D1/en not_active Expired - Lifetime
- 2003-02-26 ES ES18173392T patent/ES2745064T3/en not_active Expired - Lifetime
- 2003-02-26 NZ NZ535018A patent/NZ535018A/en not_active IP Right Cessation
- 2003-02-26 PT PT18173392T patent/PT3384931T/en unknown
- 2003-02-26 CN CNB038049767A patent/CN100398094C/en not_active Expired - Lifetime
- 2003-02-26 RS YU76704A patent/RS52387B/en unknown
- 2003-02-26 LT LTEP19166324.4T patent/LT3494995T/en unknown
- 2003-02-26 PT PT191713262T patent/PT3536344T/en unknown
- 2003-02-26 EP EP18173392.4A patent/EP3384931B1/en not_active Expired - Lifetime
- 2003-02-26 EA EA200401007A patent/EA007735B1/en not_active IP Right Cessation
- 2003-02-26 SI SI200332600T patent/SI3384931T1/en unknown
- 2003-02-26 JP JP2003572544A patent/JP2005523905A/en active Pending
- 2003-02-26 PL PL372173A patent/PL209212B1/en unknown
- 2003-02-26 EP EP19171326.2A patent/EP3536344B1/en not_active Expired - Lifetime
- 2003-02-26 DK DK18173392.4T patent/DK3384931T3/en active
- 2003-02-26 US US10/504,151 patent/US20050152846A1/en not_active Abandoned
- 2003-02-26 ME MEP-301/08A patent/MEP30108A/en unknown
- 2003-02-26 AT AT03718677T patent/ATE465712T1/en active
- 2003-02-26 SI SI200332611T patent/SI3494995T1/en unknown
- 2003-02-27 EA EA200401005A patent/EA008592B1/en not_active IP Right Cessation
- 2003-02-27 CN CNA038049724A patent/CN1638729A/en active Pending
- 2003-02-27 TW TW092104191A patent/TW200303752A/en unknown
- 2003-02-27 GE GEAP8392A patent/GEP20063876B/en unknown
- 2003-02-27 US US10/505,861 patent/US20050154013A1/en not_active Abandoned
- 2003-02-27 CA CA2477885A patent/CA2477885C/en not_active Expired - Fee Related
- 2003-02-27 PL PL03372292A patent/PL372292A1/en not_active Application Discontinuation
- 2003-02-27 BR BR0308275-0A patent/BR0308275A/en not_active IP Right Cessation
- 2003-02-27 ME MEP-302/08A patent/MEP30208A/en unknown
- 2003-02-27 KR KR1020047013502A patent/KR100961603B1/en not_active IP Right Cessation
- 2003-02-27 IL IL16384403A patent/IL163844A0/en unknown
- 2003-02-27 TW TW092104192A patent/TWI347197B/en not_active IP Right Cessation
- 2003-02-27 JP JP2003572545A patent/JP2005524664A/en not_active Withdrawn
- 2003-02-27 AU AU2003210370A patent/AU2003210370C1/en not_active Ceased
- 2003-02-27 RS YU76604A patent/RS76604A/en unknown
- 2003-02-27 NZ NZ535017A patent/NZ535017A/en not_active IP Right Cessation
- 2003-02-27 WO PCT/EP2003/002004 patent/WO2003074025A2/en active Application Filing
- 2003-02-27 EP EP03743343A patent/EP1480617A2/en not_active Withdrawn
- 2003-02-27 MX MXPA04008369A patent/MXPA04008369A/en not_active Application Discontinuation
- 2003-02-28 PE PE2003000199A patent/PE20030824A1/en active IP Right Grant
- 2003-02-28 AR ARP030100684A patent/AR038641A1/en not_active Application Discontinuation
- 2003-02-28 MY MYPI20030710A patent/MY143517A/en unknown
- 2003-02-28 AR ARP030100687A patent/AR038644A1/en unknown
- 2003-02-28 MY MYPI20030711A patent/MY137603A/en unknown
- 2003-02-28 PE PE2003000202A patent/PE20030827A1/en not_active Application Discontinuation
-
2004
- 2004-08-06 TN TNP2004000147A patent/TNSN04147A1/en unknown
- 2004-08-06 TN TNP2004000149A patent/TNSN04149A1/en unknown
- 2004-08-09 MA MA27817A patent/MA27175A1/en unknown
- 2004-08-20 HR HRP20040752AA patent/HRP20040752B1/en not_active IP Right Cessation
- 2004-08-20 HR HRP20040753 patent/HRP20040753A2/en not_active Application Discontinuation
- 2004-08-27 CO CO04084191A patent/CO5611092A2/en not_active Application Discontinuation
- 2004-08-27 CO CO04084184A patent/CO5611091A2/en not_active Application Discontinuation
- 2004-08-31 NO NO20043625A patent/NO20043625L/en not_active Application Discontinuation
- 2004-08-31 IL IL163843A patent/IL163843A/en active IP Right Grant
- 2004-08-31 NO NO20043626A patent/NO342575B1/en not_active IP Right Cessation
-
2005
- 2005-12-12 HK HK05111376.6A patent/HK1079425A1/en not_active IP Right Cessation
-
2009
- 2009-06-19 US US12/487,988 patent/US20090263488A1/en not_active Abandoned
-
2010
- 2010-05-06 JP JP2010106449A patent/JP2010215637A/en not_active Withdrawn
- 2010-06-18 CY CY20101100567T patent/CY1111133T1/en unknown
- 2010-09-01 US US12/873,690 patent/US8313732B2/en not_active Expired - Lifetime
-
2019
- 2019-09-10 CY CY20191100946T patent/CY1122027T1/en unknown
-
2020
- 2020-03-16 CY CY20201100231T patent/CY1122851T1/en unknown
- 2020-03-16 CY CY20201100230T patent/CY1122875T1/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2477885A1 (en) | Pressurised metered dose inhalers containing solutions of beta-2 agonists | |
| EP2600829B1 (en) | Pharmaceutical formulation comprising a phosphodiesterase inhibitor | |
| ZA200406919B (en) | Formoterol superfine formulation | |
| JP2006519204A (en) | A drug comprising a long-acting long-acting beta2-agonist in combination with other active ingredients | |
| CA2503183A1 (en) | Salmeterol superfine formulation | |
| US20050004228A1 (en) | Long-acting drug combinations for the treatment of respiratory complaints | |
| WO2009090009A1 (en) | Pharmaceutical formulation comprising an anticholinergic drug | |
| US20230270754A1 (en) | Combination therapy for inhalation administration |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |