CA2497171C - Water stabilized medicinal aerosol formulation - Google Patents
Water stabilized medicinal aerosol formulation Download PDFInfo
- Publication number
- CA2497171C CA2497171C CA002497171A CA2497171A CA2497171C CA 2497171 C CA2497171 C CA 2497171C CA 002497171 A CA002497171 A CA 002497171A CA 2497171 A CA2497171 A CA 2497171A CA 2497171 C CA2497171 C CA 2497171C
- Authority
- CA
- Canada
- Prior art keywords
- formulation
- parts
- weight
- combination
- propellant
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 127
- 238000009472 formulation Methods 0.000 title claims abstract description 121
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 239000000443 aerosol Substances 0.000 title claims abstract description 50
- 239000003814 drug Substances 0.000 claims abstract description 70
- 239000003380 propellant Substances 0.000 claims abstract description 39
- 239000003381 stabilizer Substances 0.000 claims abstract description 13
- 239000000725 suspension Substances 0.000 claims abstract description 9
- -1 beclomethasone compound Chemical class 0.000 claims description 20
- 239000012453 solvate Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000003246 corticosteroid Substances 0.000 claims description 9
- 239000006184 cosolvent Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000000048 adrenergic agonist Substances 0.000 claims description 8
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 7
- 229960002117 triamcinolone acetonide Drugs 0.000 claims description 7
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 claims description 7
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims description 6
- 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 description 6
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 6
- 229960004436 budesonide Drugs 0.000 claims description 6
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone 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)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 claims description 6
- 229960002052 salbutamol Drugs 0.000 claims description 6
- 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 description 5
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- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims description 5
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 claims description 5
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- 150000004677 hydrates Chemical class 0.000 claims description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 4
- 229960001361 ipratropium bromide Drugs 0.000 claims description 4
- 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 description 4
- 229960004618 prednisone Drugs 0.000 claims description 4
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 3
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 claims description 3
- 229930182837 (R)-adrenaline Natural products 0.000 claims description 3
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- 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 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 3
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 claims description 3
- VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 claims description 3
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims description 3
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 claims description 3
- 229960002576 amiloride Drugs 0.000 claims description 3
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims description 3
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 claims description 3
- 229960000396 atropine Drugs 0.000 claims description 3
- 229950000210 beclometasone dipropionate Drugs 0.000 claims description 3
- 229960004217 benzyl alcohol Drugs 0.000 claims description 3
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims description 3
- 229960002179 ephedrine Drugs 0.000 claims description 3
- 229960005139 epinephrine Drugs 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 229960002428 fentanyl Drugs 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229940039009 isoproterenol Drugs 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
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- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims description 2
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims description 2
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 2
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- 229960002537 betamethasone Drugs 0.000 claims description 2
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 claims description 2
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
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- DVIAHMIQFPOLSM-UHFFFAOYSA-N n-(2-methylphenyl)sulfonylbenzamide Chemical class CC1=CC=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1 DVIAHMIQFPOLSM-UHFFFAOYSA-N 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
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- 229920001084 poly(chloroprene) Polymers 0.000 description 1
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- HNDGEYCCZGRMTN-UHFFFAOYSA-N thieno[3,2-f:4,5-f]bis[1]benzothiophene Chemical compound S1C2=CC=3SC=CC=3C=C2C2=C1C=C(SC=C1)C1=C2 HNDGEYCCZGRMTN-UHFFFAOYSA-N 0.000 description 1
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- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
-
- 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/234,825 | 2002-09-03 | ||
| US10/234,825 US7074388B2 (en) | 1998-12-10 | 2002-09-03 | Water stabilized medicinal aerosol formulation |
| PCT/US2003/027245 WO2004022035A1 (en) | 2002-09-03 | 2003-09-03 | Water stabilized medicinal aerosol formulation related applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2497171A1 CA2497171A1 (en) | 2004-03-18 |
| CA2497171C true CA2497171C (en) | 2009-04-28 |
Family
ID=31977472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002497171A Expired - Fee Related CA2497171C (en) | 2002-09-03 | 2003-09-03 | Water stabilized medicinal aerosol formulation |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7074388B2 (https=) |
| EP (1) | EP1569617A4 (https=) |
| JP (1) | JP2006502160A (https=) |
| AU (1) | AU2003272251A1 (https=) |
| CA (1) | CA2497171C (https=) |
| DE (1) | DE03754425T1 (https=) |
| ES (1) | ES2247959T1 (https=) |
| MX (1) | MXPA05002337A (https=) |
| WO (1) | WO2004022035A1 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA006384B1 (ru) * | 2000-07-31 | 2005-12-29 | Нюкомед Данмарк А/С | Композиция фентанила для интраназального введения |
| EP1415647A1 (en) * | 2002-10-23 | 2004-05-06 | CHIESI FARMACEUTICI S.p.A. | "Long-acting beta-2 agonists ultrafine formulations" |
| DK1608336T3 (da) * | 2003-03-20 | 2008-06-02 | Boehringer Ingelheim Pharma | Formulering til en doseringsinhalator med hydrofluorakaner som drivmidler |
| CA2522231A1 (en) * | 2003-04-14 | 2004-10-21 | Vectura Ltd | Pharmaceutical compositions comprising apomorphine for pulmonary inhalation |
| US20040204439A1 (en) * | 2003-04-14 | 2004-10-14 | Staniforth John Nicholas | Composition, device, and method for treating sexual dysfunction via inhalation |
| AR041873A1 (es) * | 2003-10-30 | 2005-06-01 | Pablo Cassara Srl Lab | Una formulacion farmaceutica en aerosol adecuada para la inhalacion oral o nasal que contienen glucocorticoides en solucion estable al almacenamiento; un metodo para estabilzar formulaciones y uso de un agente estabilizante |
| GB0501956D0 (en) * | 2005-01-31 | 2005-03-09 | Arrow Internat | Nebulizer formulation |
| GB0604141D0 (en) * | 2006-03-01 | 2006-04-12 | Arrow Int Ltd | Nebulizer formulation |
| US8551534B2 (en) | 2007-10-10 | 2013-10-08 | Parion Sciences, Inc. | Inhaled hypertonic saline delivered by a heated nasal cannula |
| EP2477601B1 (en) * | 2009-09-15 | 2017-09-13 | Union Carbide Chemicals & Plastics Technology LLC | Personal care compositions with ethylene acrylic acid copolymer aqueous dispersions |
| GB0918149D0 (en) * | 2009-10-16 | 2009-12-02 | Jagotec Ag | Improved medicinal aerosol formulation |
| WO2012061195A2 (en) | 2010-11-04 | 2012-05-10 | Union Carbide Chemicals & Plastics Technology Llc | Skin care compositions |
| US8778383B2 (en) | 2011-06-07 | 2014-07-15 | Parion Sciences, Inc. | Methods of treatment |
| US8945605B2 (en) | 2011-06-07 | 2015-02-03 | Parion Sciences, Inc. | Aerosol delivery systems, compositions and methods |
| PL3104853T3 (pl) | 2014-02-10 | 2020-05-18 | Respivant Sciences Gmbh | Leczenie stabilizatorami komórek tucznych zaburzeń ogólnoustrojowych |
| ES2792682T3 (es) | 2014-02-10 | 2020-11-11 | Respivant Sciences Gmbh | Métodos para el tratamiento de enfermedades pulmonares con estabilizadores de mastocitos |
| WO2017027402A1 (en) | 2015-08-07 | 2017-02-16 | Patara Pharma, LLC | Methods for the treatment of systemic disorders treatable with mast cell stabilizers, including mast cell related disorders |
| US10238625B2 (en) | 2015-08-07 | 2019-03-26 | Respivant Sciences Gmbh | Methods for the treatment of mast cell related disorders with mast cell stabilizers |
| WO2018044942A1 (en) | 2016-08-31 | 2018-03-08 | Patara Pharma, LLC | Cromolyn compositions for treatment of chronic cough due to idiopathic pulmonary fibrosis |
| EP3522983A4 (en) | 2016-10-07 | 2020-06-03 | Respivant Sciences GmbH | CROMOLYN COMPOSITION FOR TREATING LUNG FIBROSIS |
| CA3100679A1 (en) | 2018-06-08 | 2019-12-12 | Toko Yakuhin Kogyo Co., Ltd. | Fluticasone furoate nasal preparation composition |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9202519D0 (en) * | 1992-02-06 | 1992-03-25 | Glaxo Group Ltd | Medicaments |
| DE4446891A1 (de) * | 1994-12-27 | 1996-07-04 | Falk Pharma Gmbh | Stabile wäßrige Budesonid-Lösung |
| US6458338B1 (en) * | 1998-09-22 | 2002-10-01 | Aeropharm Technology Incorporated | Amino acid stabilized medicinal aerosol formulations |
| DE19847969A1 (de) * | 1998-10-17 | 2000-04-20 | Boehringer Ingelheim Pharma | Lagerfähig flüssige Formulierung mit Formoterol |
| US6261539B1 (en) * | 1998-12-10 | 2001-07-17 | Akwete Adjei | Medicinal aerosol formulation |
| US6540983B1 (en) * | 2000-01-25 | 2003-04-01 | Aeropharm Technology Incorporated | Medical aerosol formulation |
| US6447750B1 (en) * | 2000-05-01 | 2002-09-10 | Aeropharm Technology Incorporated | Medicinal aerosol formulation |
| US6565833B1 (en) * | 2000-05-01 | 2003-05-20 | Aeropharm Technology Incorporated | Medicinal aerosol formulation |
| US6548049B1 (en) * | 2000-05-01 | 2003-04-15 | Aeropharm Technology Incorporated | Medicinal aerosol formulation |
-
2002
- 2002-09-03 US US10/234,825 patent/US7074388B2/en not_active Expired - Fee Related
-
2003
- 2003-09-03 ES ES03754425T patent/ES2247959T1/es active Pending
- 2003-09-03 JP JP2004534386A patent/JP2006502160A/ja active Pending
- 2003-09-03 DE DE03754425T patent/DE03754425T1/de active Pending
- 2003-09-03 WO PCT/US2003/027245 patent/WO2004022035A1/en not_active Ceased
- 2003-09-03 CA CA002497171A patent/CA2497171C/en not_active Expired - Fee Related
- 2003-09-03 MX MXPA05002337A patent/MXPA05002337A/es unknown
- 2003-09-03 AU AU2003272251A patent/AU2003272251A1/en not_active Abandoned
- 2003-09-03 EP EP03754425A patent/EP1569617A4/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US20030091512A1 (en) | 2003-05-15 |
| US7074388B2 (en) | 2006-07-11 |
| WO2004022035A1 (en) | 2004-03-18 |
| EP1569617A1 (en) | 2005-09-07 |
| DE03754425T1 (de) | 2006-03-09 |
| ES2247959T1 (es) | 2006-03-16 |
| CA2497171A1 (en) | 2004-03-18 |
| AU2003272251A1 (en) | 2004-03-29 |
| EP1569617A4 (en) | 2010-10-27 |
| MXPA05002337A (es) | 2005-12-05 |
| JP2006502160A (ja) | 2006-01-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130904 |