AU777505B2 - Steroid solution aerosol products with enhanced chemical stability - Google Patents
Steroid solution aerosol products with enhanced chemical stability Download PDFInfo
- Publication number
- AU777505B2 AU777505B2 AU56142/00A AU5614200A AU777505B2 AU 777505 B2 AU777505 B2 AU 777505B2 AU 56142/00 A AU56142/00 A AU 56142/00A AU 5614200 A AU5614200 A AU 5614200A AU 777505 B2 AU777505 B2 AU 777505B2
- Authority
- AU
- Australia
- Prior art keywords
- product
- ketosteroid
- container
- coating
- metal
- 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.)
- Ceased
Links
- 239000000443 aerosol Substances 0.000 title claims abstract description 44
- 150000003431 steroids Chemical class 0.000 title claims abstract description 32
- 239000000126 substance Substances 0.000 title claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 82
- 238000009472 formulation Methods 0.000 claims abstract description 72
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 238000002144 chemical decomposition reaction Methods 0.000 claims abstract description 19
- 229910052755 nonmetal Inorganic materials 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 99
- 238000000576 coating method Methods 0.000 claims description 39
- 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 36
- 229960004436 budesonide Drugs 0.000 claims description 35
- 239000011248 coating agent Substances 0.000 claims description 35
- 229910052751 metal Inorganic materials 0.000 claims description 32
- 239000002184 metal Substances 0.000 claims description 32
- 239000003380 propellant Substances 0.000 claims description 22
- 229960002117 triamcinolone acetonide Drugs 0.000 claims description 17
- 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 17
- 229960003957 dexamethasone Drugs 0.000 claims description 16
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone 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-CXSFZGCWSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 229910052782 aluminium Inorganic materials 0.000 claims description 13
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
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- 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 9
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- SNHRLVCMMWUAJD-SUYDQAKGSA-N betamethasone valerate 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)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O SNHRLVCMMWUAJD-SUYDQAKGSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
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- OHYGPBKGZGRQKT-XGQKBEPLSA-N [(8s,9r,10s,11s,13s,14s,16s,17r)-9-chloro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate 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)CO)(OC(=O)CC)[C@@]1(C)C[C@@H]2O OHYGPBKGZGRQKT-XGQKBEPLSA-N 0.000 claims description 4
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- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 3
- 229940006003 beclomethasone 17-monopropionate Drugs 0.000 claims description 3
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- VHRSUDSXCMQTMA-PJHHCJLFSA-N 6alpha-methylprednisolone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)CO)CC[C@H]21 VHRSUDSXCMQTMA-PJHHCJLFSA-N 0.000 claims description 2
- BQTXJHAJMDGOFI-NJLPOHDGSA-N Dexamethasone 21-(4-Pyridinecarboxylate) Chemical compound O=C([C@]1(O)[C@@]2(C)C[C@H](O)[C@]3(F)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)COC(=O)C1=CC=NC=C1 BQTXJHAJMDGOFI-NJLPOHDGSA-N 0.000 claims description 2
- MKPDWECBUAZOHP-AFYJWTTESA-N Paramethasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O MKPDWECBUAZOHP-AFYJWTTESA-N 0.000 claims description 2
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- FJXOGVLKCZQRDN-PHCHRAKRSA-N alclometasone Chemical compound C([C@H]1Cl)C2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O FJXOGVLKCZQRDN-PHCHRAKRSA-N 0.000 claims description 2
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- 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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- CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate 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)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 claims description 2
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- YMTMADLUXIRMGX-RFPWEZLHSA-N clocortolone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(Cl)[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1O YMTMADLUXIRMGX-RFPWEZLHSA-N 0.000 claims description 2
- WBGKWQHBNHJJPZ-LECWWXJVSA-N desonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O WBGKWQHBNHJJPZ-LECWWXJVSA-N 0.000 claims description 2
- 229960002593 desoximetasone Drugs 0.000 claims description 2
- VWVSBHGCDBMOOT-IIEHVVJPSA-N desoximetasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@@H]2O VWVSBHGCDBMOOT-IIEHVVJPSA-N 0.000 claims description 2
- 229960002344 dexamethasone sodium phosphate Drugs 0.000 claims description 2
- PLCQGRYPOISRTQ-FCJDYXGNSA-L dexamethasone sodium phosphate Chemical compound [Na+].[Na+].C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COP([O-])([O-])=O)(O)[C@@]1(C)C[C@@H]2O PLCQGRYPOISRTQ-FCJDYXGNSA-L 0.000 claims description 2
- 229960004154 diflorasone Drugs 0.000 claims description 2
- WXURHACBFYSXBI-XHIJKXOTSA-N diflorasone 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)CO)(O)[C@@]2(C)C[C@@H]1O WXURHACBFYSXBI-XHIJKXOTSA-N 0.000 claims description 2
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- WXURHACBFYSXBI-GQKYHHCASA-N flumethasone 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)CO)(O)[C@@]2(C)C[C@@H]1O WXURHACBFYSXBI-GQKYHHCASA-N 0.000 claims description 2
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- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide 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]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 claims description 2
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- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[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 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 2
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- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims 2
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Classifications
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- 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
- 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
-
- 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
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D83/00—Containers or packages with special means for dispensing contents
- B65D83/14—Containers for dispensing liquid or semi-liquid contents by internal gaseous pressure, i.e. aerosol containers comprising propellant
- B65D83/38—Details of the container body
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D83/00—Containers or packages with special means for dispensing contents
- B65D83/14—Containers for dispensing liquid or semi-liquid contents by internal gaseous pressure, i.e. aerosol containers comprising propellant
- B65D83/44—Valves specially adapted for the discharge of contents; Regulating devices
- B65D83/52—Metering valves; Metering devices
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Mechanical Engineering (AREA)
- Pulmonology (AREA)
- General Chemical & Material Sciences (AREA)
- Otolaryngology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13996199P | 1999-06-18 | 1999-06-18 | |
| US60/139961 | 1999-06-18 | ||
| PCT/US2000/016462 WO2000078286A1 (en) | 1999-06-18 | 2000-06-15 | Steroid solution aerosol products with enhanced chemical stability |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5614200A AU5614200A (en) | 2001-01-09 |
| AU777505B2 true AU777505B2 (en) | 2004-10-21 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU56142/00A Ceased AU777505B2 (en) | 1999-06-18 | 2000-06-15 | Steroid solution aerosol products with enhanced chemical stability |
Country Status (8)
| Country | Link |
|---|---|
| US (4) | US6315985B1 (https=) |
| EP (2) | EP1693053B1 (https=) |
| JP (1) | JP4777560B2 (https=) |
| AT (2) | ATE523190T1 (https=) |
| AU (1) | AU777505B2 (https=) |
| CA (1) | CA2371931A1 (https=) |
| DE (1) | DE60026840T2 (https=) |
| WO (1) | WO2000078286A1 (https=) |
Families Citing this family (76)
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| US20010031244A1 (en) * | 1997-06-13 | 2001-10-18 | Chiesi Farmaceutici S.P.A. | Pharmaceutical aerosol composition |
| DZ2947A1 (fr) | 1998-11-25 | 2004-03-15 | Chiesi Farma Spa | Inhalateur à compteur de dose sous pression. |
| 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 |
| IT1313553B1 (it) | 1999-07-23 | 2002-09-09 | Chiesi Farma Spa | Formulazioni ottimizzate costituite da soluzioni di steroidi dasomministrare per inalazione. |
| EP1143930B8 (en) * | 1999-09-11 | 2008-03-19 | Glaxo Group Limited | Pharmaceutical formulation of fluticasone propionate |
| AU2206801A (en) * | 1999-12-24 | 2001-07-09 | Alan Leslie Cripps | Pharmaceutical aerosol formulation of salmeterol and fluticasone propionate |
| IT1317846B1 (it) | 2000-02-22 | 2003-07-15 | Chiesi Farma Spa | Formulazioni contenenti un farmaco anticolinergico per il trattamentodella broncopneumopatia cronica ostruttiva. |
| IT1318514B1 (it) * | 2000-05-12 | 2003-08-27 | Chiesi Farma Spa | Formulazioni contenenti un farmaco glucocorticosteroide per iltrattamento di patologie broncopolmonari. |
| AU2000250701B2 (en) | 2000-05-22 | 2004-07-01 | Chiesi Farmaceutici S.P.A. | Stable pharmaceutical solution formulations for pressurised metered dose inhalers |
| TW523409B (en) * | 2000-09-15 | 2003-03-11 | Baxter Int | Container for inhalation anesthetic |
| GB0025092D0 (en) * | 2000-10-13 | 2000-11-29 | Glaxo Group Ltd | Medicament dispenser |
| EP1324797A2 (en) * | 2000-10-13 | 2003-07-09 | Glaxo Group Limited | Medicament dispenser |
| US20020085978A1 (en) * | 2000-11-10 | 2002-07-04 | Mina Buenafe | Degradation-resistant glucocorticosteroid formulations |
| DE10062564A1 (de) * | 2000-12-15 | 2002-06-20 | Linde Ag | Schutzgas und Verfahren zum Lichtbogenschweißen |
| 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 |
| GB0106046D0 (en) | 2001-03-12 | 2001-05-02 | Glaxo Group Ltd | Canister |
| TR200401980T4 (tr) * | 2001-07-02 | 2004-09-21 | Chiesi Farmaceutici S.P.A. | Aerosol olarak uygulama için en uygun hale getirilmiş tobramisin formülasyonu |
| GB0122725D0 (en) * | 2001-09-21 | 2001-11-14 | Glaxo Group Ltd | Drug dispensing components |
| JP2005514437A (ja) * | 2001-12-21 | 2005-05-19 | スリーエム イノベイティブ プロパティズ カンパニー | イオン対複合体を含む医薬用エアロゾル製剤 |
| ES2342463T3 (es) * | 2002-03-01 | 2010-07-07 | Chiesi Farmaceutici S.P.A. | Formulacion superfina de formoterol. |
| US7344707B2 (en) * | 2002-05-15 | 2008-03-18 | The Procter & Gamble Company | Low combustion aerosol products in plastic packages having a reduced fire hazard classification that subsequently reduces storage costs |
| US20030215400A1 (en) * | 2002-05-15 | 2003-11-20 | The Procter & Gamble Company | Pressurized package made of a polyamide resin and containing dimethyl ether |
| JP3691459B2 (ja) * | 2002-06-14 | 2005-09-07 | 久光メディカル株式会社 | 粉末状吸入剤組成物 |
| ATE470468T1 (de) * | 2003-08-04 | 2010-06-15 | Alexza Pharmaceuticals Inc | Substrate für eine medikamentenverabreichungsvorrichtung und verfahren zur bereitung |
| BRPI0413558A (pt) | 2003-08-12 | 2006-10-17 | 3M Innovative Properties Co | compostos contendo imidazo substituìdo por hidroxilamina |
| AU2004268625B2 (en) | 2003-08-27 | 2011-03-31 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| AU2004270201A1 (en) | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for CD5+ B cell lymphoma |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| AR046046A1 (es) | 2003-10-03 | 2005-11-23 | 3M Innovative Properties Co | Imidazoquinolinas alcoxi sustituidas. composiciones farmaceuticas. |
| 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 |
| CA2545825A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| EP1685129A4 (en) | 2003-11-14 | 2008-10-22 | 3M Innovative Properties Co | OXIMSUBSTITUTED IMIDAZORING CONNECTIONS |
| CA2547020C (en) | 2003-11-25 | 2014-03-25 | 3M Innovative Properties Company | 1h-imidazo[4,5-c]pyridine-4-amine derivatives as immune response modifier |
| US20050121025A1 (en) | 2003-12-04 | 2005-06-09 | Gamard Stephan C.F. | Portable gas operating inhaler |
| JP2007517035A (ja) | 2003-12-29 | 2007-06-28 | スリーエム イノベイティブ プロパティズ カンパニー | アリールアルケニルおよびアリールアルキニル置換されたイミダゾキノリン |
| EP1699788A2 (en) | 2003-12-30 | 2006-09-13 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl and imidazonaphthyridinyl sulfonamides |
| EP1595531A1 (en) | 2004-05-13 | 2005-11-16 | CHIESI FARMACEUTICI S.p.A. | Stable pharmaceutical solution formulations for pressurized metered dose inhalers |
| WO2005094531A2 (en) | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| US8017779B2 (en) | 2004-06-15 | 2011-09-13 | 3M Innovative Properties Company | Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| US8026366B2 (en) | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| WO2006038923A2 (en) | 2004-06-18 | 2006-04-13 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| WO2006065280A2 (en) | 2004-06-18 | 2006-06-22 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods |
| JP5543068B2 (ja) | 2004-12-30 | 2014-07-09 | スリーエム イノベイティブ プロパティズ カンパニー | キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 |
| EP1831221B1 (en) | 2004-12-30 | 2012-08-08 | 3M Innovative Properties Company | Substituted chiral fused 1,2 imidazo 4,5-c ring compounds |
| AU2006210392A1 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune response modifiers |
| AU2006213746A1 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo(4,5-c) ring compounds and methods |
| EP1850831B1 (en) | 2005-02-25 | 2015-12-02 | CHIESI FARMACEUTICI S.p.A. | Pharmaceutical aerosol formulations for pressurized metered dose inhalers comprising a sequestering agent |
| EP1869043A2 (en) | 2005-04-01 | 2007-12-26 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| AU2006232375A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| WO2006130510A2 (en) * | 2005-05-27 | 2006-12-07 | Taro Pharmaceuticals U.S.A., Inc. | Stable liquid desoximethasone compositions with reduced oxidized impurity |
| EP1998833B1 (en) * | 2006-03-24 | 2012-12-26 | 3M Innovative Properties Company | Medicinal formulation container with a treated metal surface |
| US20070231396A1 (en) * | 2006-03-29 | 2007-10-04 | Ray Charles D | Medication spray formulation |
| US20070286814A1 (en) * | 2006-06-12 | 2007-12-13 | Medispray Laboratories Pvt. Ltd. | Stable aerosol pharmaceutical formulations |
| GB0613761D0 (en) * | 2006-07-11 | 2006-08-23 | Norton Healthcare Ltd | A pharmaceutical formulation and method for the preparation thereof |
| US7906506B2 (en) | 2006-07-12 | 2011-03-15 | 3M Innovative Properties Company | Substituted chiral fused [1,2] imidazo [4,5-c] ring compounds and methods |
| CA2669924A1 (en) * | 2006-11-20 | 2008-05-29 | Cipla Limited | An aerosol device |
| WO2008112661A2 (en) | 2007-03-09 | 2008-09-18 | Alexza Pharmaceuticals, Inc. | Heating unit for use in a drug delivery device |
| BRPI0819259A2 (pt) * | 2007-11-07 | 2019-10-01 | Astrazeneca Ab | formulações de pó seco compreendendo derivados do ácido ascórbico. |
| US8227027B2 (en) * | 2007-12-07 | 2012-07-24 | Presspart Gmbh & Co. Kg | Method for applying a polymer coating to an internal surface of a container |
| US20090208424A1 (en) * | 2008-02-19 | 2009-08-20 | Todd Maibach | Compositions and methods for delivery of solution to the skin |
| US9278048B2 (en) * | 2009-05-06 | 2016-03-08 | Baxter International, Inc. | Pharmaceutical product and method of use |
| EP3020393B1 (en) | 2009-12-16 | 2020-10-07 | 3M Innovative Properties Company | Formulations and methods for controlling mdi particle size delivery |
| PT2627386E (pt) * | 2010-10-12 | 2015-06-11 | Ivax Pharmaceuticals Ireland | Dispositivo de pulverização nasal |
| US20120204871A1 (en) * | 2011-02-10 | 2012-08-16 | Julio Cesar Vega | Stable, non-corrosive formulations for pressurized metered dose inhalers |
| DE102014112595A1 (de) * | 2014-09-02 | 2016-03-03 | Reinhard Caliebe | Dose für ein medizinisches, pharmazeutisches oder kosmetisches Fluid |
| US12214118B2 (en) | 2018-02-02 | 2025-02-04 | Alexza Pharmaceuticals, Inc. | Electrical condensation aerosol device |
| CN111939143A (zh) * | 2019-05-16 | 2020-11-17 | 鲁南制药集团股份有限公司 | 一种布地奈德溶液型气雾剂及其制备方法 |
| US11964121B2 (en) | 2021-10-13 | 2024-04-23 | Satio, Inc. | Mono dose dermal patch for pharmaceutical delivery |
| US12053284B2 (en) | 2021-11-08 | 2024-08-06 | Satio, Inc. | Dermal patch for collecting a physiological sample |
| US11452474B1 (en) | 2021-04-14 | 2022-09-27 | Satio, Inc. | Dual lever dermal patch system |
| US12023156B2 (en) | 2021-10-13 | 2024-07-02 | Satio, Inc. | Dermal patch for collecting a physiological sample |
| US12214346B2 (en) | 2021-10-13 | 2025-02-04 | Satio, Inc. | Dermal patch with a diagnostic test strip |
| US11877848B2 (en) | 2021-11-08 | 2024-01-23 | Satio, Inc. | Dermal patch for collecting a physiological sample |
| US12048543B2 (en) | 2021-11-08 | 2024-07-30 | Satio, Inc. | Dermal patch for collecting a physiological sample with removable vial |
| US12178979B2 (en) | 2021-10-13 | 2024-12-31 | Satio, Inc. | Dermal patch for delivering a pharmaceutical |
| WO2025128797A1 (en) | 2023-12-13 | 2025-06-19 | Blue Evolution, Inc | Ecofriendly, biodegradable biological polysaccharide composition for packaging materials |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996032345A1 (en) * | 1995-04-14 | 1996-10-17 | Glaxo Wellcome Inc. | Metered dose inhaler for beclomethasone dipropionate |
| WO1996032151A1 (en) * | 1995-04-14 | 1996-10-17 | Glaxo Wellcome Inc. | Metered dose inhaler for fluticasone propionate |
| US5776433A (en) * | 1993-12-20 | 1998-07-07 | Minnesota Mining And Manufacturing Company | Flunisolide aerosol formulations |
Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US577433A (en) * | 1897-02-23 | Door-alarm | ||
| BE555319A (https=) * | 1956-03-21 | 1900-01-01 | ||
| US3361306A (en) * | 1966-03-31 | 1968-01-02 | Merck & Co Inc | Aerosol unit dispensing uniform amounts of a medically active ingredient |
| IT1034011B (it) * | 1969-06-26 | 1979-09-10 | Vister Vismara Terapeutici S P | Processo per la prapratzione di 17 monoesteri di 17 a 21 diossisteroidi per idrolisi die corpispondenti 17 21 ortoesteri ciclici a ph control lato |
| US3622053A (en) * | 1969-12-10 | 1971-11-23 | Schering Corp | Aerosol inhaler with flip-up nozzle |
| US3923484A (en) * | 1974-01-11 | 1975-12-02 | Corning Glass Works | Flame method of producing glass |
| 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 (it) * | 1984-06-11 | 1988-11-10 | Sicor Spa | Procedimento per la preparazione di 16,17-acetali di derivati pregnanici e nuovi composti ottenuti |
| US5192528A (en) * | 1985-05-22 | 1993-03-09 | Liposome Technology, Inc. | Corticosteroid inhalation treatment method |
| DE68915203T2 (de) | 1988-03-22 | 1994-09-22 | Fisons Plc, Ipswich, Suffolk | Pharmazeutische Mischungen. |
| US5225183A (en) * | 1988-12-06 | 1993-07-06 | Riker Laboratories, Inc. | Medicinal aerosol formulations |
| US5776434A (en) | 1988-12-06 | 1998-07-07 | Riker Laboratories, Inc. | Medicinal aerosol formulations |
| MX9203481A (es) | 1990-10-18 | 1992-07-01 | Minnesota Mining & Mfg | Formulaciones. |
| US6006745A (en) * | 1990-12-21 | 1999-12-28 | Minnesota Mining And Manufacturing Company | Device for delivering an aerosol |
| CZ282972B6 (cs) * | 1991-08-29 | 1997-11-12 | Broncho-Air Medizintechnik Ag | Lékařský přístroj pro inhalování dávkovaných aerosolů |
| DE4230876A1 (de) * | 1992-03-17 | 1993-09-23 | Asta Medica Ag | Druckgaspackungen unter verwendung von polyoxyethylen-glyceryl-oleaten |
| ATE177941T1 (de) * | 1992-12-09 | 1999-04-15 | Boehringer Ingelheim Pharma | Stabilisierte medizinische aerosollösungen |
| SE9203743D0 (sv) * | 1992-12-11 | 1992-12-11 | Astra Ab | Efficient use |
| US6596260B1 (en) | 1993-08-27 | 2003-07-22 | Novartis Corporation | Aerosol container and a method for storage and administration of a predetermined amount of a pharmaceutically active aerosol |
| US5653961A (en) * | 1995-03-31 | 1997-08-05 | Minnesota Mining And Manufacturing Company | Butixocort aerosol formulations in hydrofluorocarbon propellant |
| TR199701169T1 (xx) * | 1995-04-14 | 1998-03-21 | Glaxo Wellcome Inc. | Salmeterol i�in �l��lm�� doz inhaleri. |
| HU219900B (hu) * | 1995-04-14 | 2001-09-28 | Glaxo Wellcome Inc. | Mért dózist adagoló inhalálóberendezés |
| CA2223385A1 (en) | 1995-06-07 | 1996-12-19 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Stabilized steroid compositions |
| US5776573A (en) | 1996-04-16 | 1998-07-07 | Cd Magic, Inc. | Compact disc revitalizer formulations and revitalizer |
| US5743251A (en) | 1996-05-15 | 1998-04-28 | Philip Morris Incorporated | Aerosol and a method and apparatus for generating an aerosol |
| US6039932A (en) * | 1996-09-27 | 2000-03-21 | 3M Innovative Properties Company | Medicinal inhalation aerosol formulations containing budesonide |
| GB9620187D0 (en) | 1996-09-27 | 1996-11-13 | Minnesota Mining & Mfg | Medicinal aerosol formulations |
| US6413496B1 (en) * | 1996-12-04 | 2002-07-02 | Biogland Ireland (R&D) Limited | Pharmaceutical compositions and devices for their administration |
| DE69734017T2 (de) | 1996-12-04 | 2006-06-14 | Link Products Ltd | Arzneimittelzusammensetzungen und vorrichtungen zu deren verabreichung |
| US6126919A (en) * | 1997-02-07 | 2000-10-03 | 3M Innovative Properties Company | Biocompatible compounds for pharmaceutical drug delivery systems |
| US5891420A (en) * | 1997-04-21 | 1999-04-06 | Aeropharm Technology Limited | Environmentally safe triancinolone acetonide aerosol formulations for oral inhalation |
| US5891419A (en) * | 1997-04-21 | 1999-04-06 | Aeropharm Technology Limited | Environmentally safe flunisolide aerosol formulations for oral inhalation |
| US6120752A (en) | 1997-05-21 | 2000-09-19 | 3M Innovative Properties Company | Medicinal aerosol products containing formulations of ciclesonide and related steroids |
| 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 |
| GB9805938D0 (en) | 1998-03-19 | 1998-05-13 | Glaxo Group Ltd | Valve for aerosol container |
| 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 |
| US6241969B1 (en) * | 1998-06-26 | 2001-06-05 | Elan Corporation Plc | Aqueous compositions containing corticosteroids for nasal and pulmonary delivery |
| DE19847969A1 (de) * | 1998-10-17 | 2000-04-20 | Boehringer Ingelheim Pharma | Lagerfähig flüssige Formulierung mit Formoterol |
| PL200941B1 (pl) * | 1998-11-13 | 2009-02-27 | Jagotec Ag | Suchy proszkowy preparat inhalacyjny |
| IT1303788B1 (it) * | 1998-11-25 | 2001-02-23 | Chiesi Farma Spa | Formulazioni di aerosol medicinali. |
| DZ2947A1 (fr) * | 1998-11-25 | 2004-03-15 | Chiesi Farma Spa | Inhalateur à compteur de dose sous pression. |
| US6261539B1 (en) * | 1998-12-10 | 2001-07-17 | Akwete Adjei | Medicinal aerosol formulation |
| US6290930B1 (en) * | 1998-12-18 | 2001-09-18 | Baker Norton Pharmaceuticals, Inc. | Pharmaceutical solution aerosol formulations containing fluoroalkanes and budesonide |
| US6004537A (en) * | 1998-12-18 | 1999-12-21 | Baker Norton Pharmaceuticals, Inc. | Pharmaceutical solution aerosol formulations containing fluoroalkanes, budesonide and formoterol |
| 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 |
| US6322053B1 (en) * | 2000-02-08 | 2001-11-27 | Valiant Machine & Tool Inc. | Balancing system with a force multiplying device |
| IT1317846B1 (it) * | 2000-02-22 | 2003-07-15 | Chiesi Farma Spa | Formulazioni contenenti un farmaco anticolinergico per il trattamentodella broncopneumopatia cronica ostruttiva. |
| IT1318514B1 (it) * | 2000-05-12 | 2003-08-27 | Chiesi Farma Spa | Formulazioni contenenti un farmaco glucocorticosteroide per iltrattamento di patologie broncopolmonari. |
| US20060257324A1 (en) * | 2000-05-22 | 2006-11-16 | Chiesi Farmaceutici S.P.A. | Pharmaceutical solution formulations for pressurised metered dose inhalers |
| AU2000250701B2 (en) * | 2000-05-22 | 2004-07-01 | Chiesi Farmaceutici S.P.A. | Stable pharmaceutical solution formulations for pressurised metered dose inhalers |
| EP1340492A1 (en) * | 2002-03-01 | 2003-09-03 | CHIESI FARMACEUTICI S.p.A. | Aerosol formulations for pulmonary administration of medicaments having systemic effects |
| EP1415647A1 (en) * | 2002-10-23 | 2004-05-06 | CHIESI FARMACEUTICI S.p.A. | "Long-acting beta-2 agonists ultrafine formulations" |
| ES2342463T3 (es) * | 2002-03-01 | 2010-07-07 | Chiesi Farmaceutici S.P.A. | Formulacion superfina de formoterol. |
| CA2388352A1 (en) * | 2002-05-31 | 2003-11-30 | Voiceage Corporation | A method and device for frequency-selective pitch enhancement of synthesized speed |
| EP1595531A1 (en) * | 2004-05-13 | 2005-11-16 | CHIESI FARMACEUTICI S.p.A. | Stable pharmaceutical solution formulations for pressurized metered dose inhalers |
-
2000
- 2000-06-13 US US09/592,885 patent/US6315985B1/en not_active Expired - Lifetime
- 2000-06-15 AT AT06005429T patent/ATE523190T1/de not_active IP Right Cessation
- 2000-06-15 EP EP06005429A patent/EP1693053B1/en not_active Expired - Lifetime
- 2000-06-15 CA CA002371931A patent/CA2371931A1/en not_active Abandoned
- 2000-06-15 AU AU56142/00A patent/AU777505B2/en not_active Ceased
- 2000-06-15 WO PCT/US2000/016462 patent/WO2000078286A1/en not_active Ceased
- 2000-06-15 DE DE60026840T patent/DE60026840T2/de not_active Expired - Lifetime
- 2000-06-15 AT AT00941435T patent/ATE320794T1/de not_active IP Right Cessation
- 2000-06-15 JP JP2001504351A patent/JP4777560B2/ja not_active Expired - Fee Related
- 2000-06-15 EP EP00941435A patent/EP1194121B1/en not_active Expired - Lifetime
-
2001
- 2001-10-04 US US09/970,746 patent/US6610273B2/en not_active Expired - Lifetime
-
2003
- 2003-07-30 US US10/630,414 patent/US20040033201A1/en not_active Abandoned
-
2005
- 2005-02-22 US US11/061,529 patent/US20050220717A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5776433A (en) * | 1993-12-20 | 1998-07-07 | Minnesota Mining And Manufacturing Company | Flunisolide aerosol formulations |
| WO1996032345A1 (en) * | 1995-04-14 | 1996-10-17 | Glaxo Wellcome Inc. | Metered dose inhaler for beclomethasone dipropionate |
| WO1996032151A1 (en) * | 1995-04-14 | 1996-10-17 | Glaxo Wellcome Inc. | Metered dose inhaler for fluticasone propionate |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE523190T1 (de) | 2011-09-15 |
| JP2003502357A (ja) | 2003-01-21 |
| AU5614200A (en) | 2001-01-09 |
| US20020071810A1 (en) | 2002-06-13 |
| US6610273B2 (en) | 2003-08-26 |
| CA2371931A1 (en) | 2000-12-28 |
| US20050220717A1 (en) | 2005-10-06 |
| DE60026840D1 (de) | 2006-05-11 |
| DE60026840T2 (de) | 2006-10-12 |
| EP1194121A1 (en) | 2002-04-10 |
| EP1194121B1 (en) | 2006-03-22 |
| JP4777560B2 (ja) | 2011-09-21 |
| EP1693053B1 (en) | 2011-09-07 |
| EP1693053A3 (en) | 2007-06-27 |
| US20040033201A1 (en) | 2004-02-19 |
| US6315985B1 (en) | 2001-11-13 |
| ATE320794T1 (de) | 2006-04-15 |
| WO2000078286A1 (en) | 2000-12-28 |
| EP1693053A2 (en) | 2006-08-23 |
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Legal Events
| Date | Code | Title | Description |
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| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |