AU675633B2 - Suspension aerosol formulations - Google Patents
Suspension aerosol formulations Download PDFInfo
- Publication number
- AU675633B2 AU675633B2 AU32728/93A AU3272893A AU675633B2 AU 675633 B2 AU675633 B2 AU 675633B2 AU 32728/93 A AU32728/93 A AU 32728/93A AU 3272893 A AU3272893 A AU 3272893A AU 675633 B2 AU675633 B2 AU 675633B2
- Authority
- AU
- Australia
- Prior art keywords
- drug
- percent
- line
- formulation according
- international
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 204
- 238000009472 formulation Methods 0.000 title claims abstract description 177
- 239000000443 aerosol Substances 0.000 title claims abstract description 79
- 239000000725 suspension Substances 0.000 title description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 74
- 239000003380 propellant Substances 0.000 claims abstract description 72
- 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 abstract description 50
- BNPSSFBOAGDEEL-UHFFFAOYSA-N albuterol sulfate Chemical compound OS(O)(=O)=O.CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1.CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 BNPSSFBOAGDEEL-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000007971 pharmaceutical suspension Substances 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims description 99
- 229940079593 drug Drugs 0.000 claims description 92
- QSXMZJGGEWYVCN-UHFFFAOYSA-N Pirbuterol acetate Chemical compound CC(O)=O.CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 QSXMZJGGEWYVCN-UHFFFAOYSA-N 0.000 claims description 42
- 229960004994 pirbuterol acetate Drugs 0.000 claims description 42
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 35
- 229940057282 albuterol sulfate Drugs 0.000 claims description 31
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- OBRNDARFFFHCGE-PERKLWIXSA-N (S,S)-formoterol fumarate Chemical compound OC(=O)\C=C\C(O)=O.C1=CC(OC)=CC=C1C[C@H](C)NC[C@@H](O)C1=CC=C(O)C(NC=O)=C1.C1=CC(OC)=CC=C1C[C@H](C)NC[C@@H](O)C1=CC=C(O)C(NC=O)=C1 OBRNDARFFFHCGE-PERKLWIXSA-N 0.000 claims description 11
- 229960000193 formoterol fumarate Drugs 0.000 claims description 11
- 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 10
- 238000005189 flocculation Methods 0.000 claims description 10
- 230000016615 flocculation Effects 0.000 claims description 10
- 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 9
- 229960000265 cromoglicic acid Drugs 0.000 claims description 8
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 claims description 8
- 229960005414 pirbuterol Drugs 0.000 claims description 8
- 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 7
- 229950000210 beclometasone dipropionate Drugs 0.000 claims description 7
- 229960002052 salbutamol Drugs 0.000 claims description 7
- 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 6
- 229960002848 formoterol Drugs 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 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 5
- 229960004017 salmeterol Drugs 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 238000005065 mining Methods 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 239000011521 glass Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002245 particle Substances 0.000 description 12
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 9
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 8
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 8
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 8
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 8
- 239000005642 Oleic acid Substances 0.000 description 8
- 239000011324 bead Substances 0.000 description 8
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 8
- 229940071648 metered dose inhaler Drugs 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 229920000098 polyolefin Polymers 0.000 description 7
- 238000010998 test method Methods 0.000 description 7
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229920002725 thermoplastic elastomer Polymers 0.000 description 6
- 239000004147 Sorbitan trioleate Substances 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 5
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 238000010304 firing Methods 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 229960000391 sorbitan trioleate Drugs 0.000 description 5
- 235000019337 sorbitan trioleate Nutrition 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000011089 carbon dioxide Nutrition 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 3
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 238000004062 sedimentation Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 229940029284 trichlorofluoromethane Drugs 0.000 description 3
- 229940070384 ventolin Drugs 0.000 description 3
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000007883 bronchodilation Effects 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 238000002788 crimping Methods 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 239000008249 pharmaceutical aerosol Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229940124631 β2-adrenergic bronchodilator Drugs 0.000 description 2
- 229940051271 1,1-difluoroethane Drugs 0.000 description 1
- BHNZEZWIUMJCGF-UHFFFAOYSA-N 1-chloro-1,1-difluoroethane Chemical compound CC(F)(F)Cl BHNZEZWIUMJCGF-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 101710180366 CDP-L-myo-inositol myo-inositolphosphotransferase Proteins 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 102100032596 Fibrocystin Human genes 0.000 description 1
- 235000001018 Hibiscus sabdariffa Nutrition 0.000 description 1
- 101000730595 Homo sapiens Fibrocystin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 235000005291 Rumex acetosa Nutrition 0.000 description 1
- 240000007001 Rumex acetosella Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000013536 elastomeric material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000003921 particle size analysis Methods 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- -1 polyethylene terephthalate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K9/124—Aerosols; Foams characterised by the propellant
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dispersion Chemistry (AREA)
- Pulmonology (AREA)
- Emergency Medicine (AREA)
- Otolaryngology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Colloid Chemistry (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU12342/97A AU709052C (en) | 1991-12-18 | 1997-01-28 | Suspension aerosol formulations |
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81040191A | 1991-12-18 | 1991-12-18 | |
| US80979191A | 1991-12-18 | 1991-12-18 | |
| US810401 | 1991-12-18 | ||
| US809791 | 1991-12-18 | ||
| US87803992A | 1992-05-04 | 1992-05-04 | |
| US878039 | 1992-05-04 | ||
| PCT/US1992/010587 WO1993011747A1 (en) | 1991-12-18 | 1992-12-11 | Suspension aerosol formulations |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU12342/97A Division AU709052C (en) | 1991-12-18 | 1997-01-28 | Suspension aerosol formulations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3272893A AU3272893A (en) | 1993-07-19 |
| AU675633B2 true AU675633B2 (en) | 1997-02-13 |
Family
ID=27420051
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU32728/93A Expired AU675633B2 (en) | 1991-12-18 | 1992-12-11 | Suspension aerosol formulations |
| AU12342/97A Expired AU709052C (en) | 1991-12-18 | 1997-01-28 | Suspension aerosol formulations |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU12342/97A Expired AU709052C (en) | 1991-12-18 | 1997-01-28 | Suspension aerosol formulations |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6743413B1 (enExample) |
| EP (3) | EP0717987B1 (enExample) |
| JP (2) | JP3908269B2 (enExample) |
| AT (3) | ATE150296T1 (enExample) |
| AU (2) | AU675633B2 (enExample) |
| CA (2) | CA2126244C (enExample) |
| DE (3) | DE69218455T2 (enExample) |
| DK (3) | DK0617610T3 (enExample) |
| ES (3) | ES2099415T3 (enExample) |
| GR (2) | GR3022874T3 (enExample) |
| NZ (1) | NZ246421A (enExample) |
| PT (2) | PT1086688E (enExample) |
| WO (1) | WO1993011747A1 (enExample) |
Families Citing this family (121)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE339952T1 (de) | 1991-06-10 | 2006-10-15 | Schering Corp | Fluorchlorkohlenwasserstofffreie aerosolformulierungen |
| US5674471A (en) * | 1991-12-12 | 1997-10-07 | Glaxo Group Limited | Aerosol formulations containing P134a and salbutamol |
| US5653962A (en) * | 1991-12-12 | 1997-08-05 | Glaxo Group Limited | Aerosol formulations containing P134a and particulate medicaments |
| DE69205177T2 (de) * | 1991-12-12 | 1996-03-21 | Glaxo Group Ltd., Greenford, Middlesex | Pharmazeutische Aerosolformulierung. |
| US5736124A (en) * | 1991-12-12 | 1998-04-07 | Glaxo Group Limited | Aerosol formulations containing P134a and particulate medicament |
| US5744123A (en) * | 1991-12-12 | 1998-04-28 | Glaxo Group Limited | Aerosol formulations containing P134a and particulate medicaments |
| CA2125666C (en) | 1991-12-12 | 2002-07-16 | Rachel Ann Akehurst | Medicaments |
| IL104068A (en) | 1991-12-12 | 1998-10-30 | Glaxo Group Ltd | Surfactant-free pharmaceutical aerosol formulation comprising 1,1,1,2-tetrafluoroethane or 1,1,1,2,3,3,3-heptafluoro-n- propane as propellant |
| US5658549A (en) * | 1991-12-12 | 1997-08-19 | Glaxo Group Limited | Aerosol formulations containing propellant 134a and fluticasone propionate |
| US5916540A (en) | 1994-10-24 | 1999-06-29 | Glaxo Group Limited | Aerosol formulations containing P134A and/or P227 and particulate medicament |
| US7105152B1 (en) | 1991-12-18 | 2006-09-12 | 3M Innovative Properties Company | Suspension aerosol formulations |
| US7101534B1 (en) | 1991-12-18 | 2006-09-05 | 3M Innovative Properties Company | Suspension aerosol formulations |
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1992
- 1992-12-11 JP JP51102793A patent/JP3908269B2/ja not_active Expired - Lifetime
- 1992-12-11 DE DE69218455T patent/DE69218455T2/de not_active Revoked
- 1992-12-11 CA CA002126244A patent/CA2126244C/en not_active Expired - Lifetime
- 1992-12-11 DE DE69233319T patent/DE69233319T2/de not_active Expired - Lifetime
- 1992-12-11 DK DK93901414.8T patent/DK0617610T3/da active
- 1992-12-11 WO PCT/US1992/010587 patent/WO1993011747A1/en not_active Ceased
- 1992-12-11 ES ES93901414T patent/ES2099415T3/es not_active Expired - Lifetime
- 1992-12-11 ES ES96200109T patent/ES2159678T3/es not_active Expired - Lifetime
- 1992-12-11 AT AT93901414T patent/ATE150296T1/de not_active IP Right Cessation
- 1992-12-11 AU AU32728/93A patent/AU675633B2/en not_active Expired
- 1992-12-11 DK DK00123885T patent/DK1086688T3/da active
- 1992-12-11 AT AT96200109T patent/ATE204743T1/de not_active IP Right Cessation
- 1992-12-11 AT AT00123885T patent/ATE260641T1/de active
- 1992-12-11 EP EP96200109A patent/EP0717987B1/en not_active Revoked
- 1992-12-11 DK DK96200109T patent/DK0717987T3/da active
- 1992-12-11 EP EP00123885A patent/EP1086688B1/en not_active Expired - Lifetime
- 1992-12-11 NZ NZ246421A patent/NZ246421A/en unknown
- 1992-12-11 PT PT00123885T patent/PT1086688E/pt unknown
- 1992-12-11 ES ES00123885T patent/ES2216800T3/es not_active Expired - Lifetime
- 1992-12-11 PT PT96200109T patent/PT717987E/pt unknown
- 1992-12-11 EP EP93901414A patent/EP0617610B1/en not_active Revoked
- 1992-12-11 DE DE69232034T patent/DE69232034T2/de not_active Revoked
- 1992-12-11 CA CA002320129A patent/CA2320129C/en not_active Expired - Lifetime
-
1995
- 1995-05-31 US US08/455,280 patent/US6743413B1/en not_active Expired - Lifetime
-
1997
- 1997-01-28 AU AU12342/97A patent/AU709052C/en not_active Expired
- 1997-03-20 GR GR970400329T patent/GR3022874T3/el unknown
-
2001
- 2001-08-30 GR GR20010401322T patent/GR3036467T3/el not_active IP Right Cessation
-
2004
- 2004-01-08 JP JP2004003462A patent/JP2004143183A/ja active Pending
- 2004-04-09 US US10/820,817 patent/US20040197273A1/en not_active Abandoned
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| WO1991004011A1 (en) * | 1989-09-20 | 1991-04-04 | Riker Laboratories, Inc. | Medicinal aerosol formulations |
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