CA2708083C - Organic compounds - Google Patents
Organic compounds Download PDFInfo
- Publication number
- CA2708083C CA2708083C CA2708083A CA2708083A CA2708083C CA 2708083 C CA2708083 C CA 2708083C CA 2708083 A CA2708083 A CA 2708083A CA 2708083 A CA2708083 A CA 2708083A CA 2708083 C CA2708083 C CA 2708083C
- Authority
- CA
- Canada
- Prior art keywords
- drug substance
- micronised
- glycopyrrolate
- particle size
- hours
- 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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- 150000002894 organic compounds Chemical class 0.000 title description 2
- 229940088679 drug related substance Drugs 0.000 claims abstract description 65
- 239000002245 particle Substances 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 40
- 230000008569 process Effects 0.000 claims abstract description 39
- 238000003860 storage Methods 0.000 claims abstract description 7
- VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical group [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 claims description 27
- 229940015042 glycopyrrolate Drugs 0.000 claims description 24
- ANGKOCUUWGHLCE-HKUYNNGSSA-N [(3s)-1,1-dimethylpyrrolidin-1-ium-3-yl] (2r)-2-cyclopentyl-2-hydroxy-2-phenylacetate Chemical class C1[N+](C)(C)CC[C@@H]1OC(=O)[C@](O)(C=1C=CC=CC=1)C1CCCC1 ANGKOCUUWGHLCE-HKUYNNGSSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 230000000181 anti-adherent effect Effects 0.000 claims description 8
- 239000003911 antiadherent Substances 0.000 claims description 8
- 239000008186 active pharmaceutical agent Substances 0.000 abstract description 51
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 18
- 239000000463 material Substances 0.000 description 14
- 230000002776 aggregation Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 235000019359 magnesium stearate Nutrition 0.000 description 9
- 238000004220 aggregation Methods 0.000 description 8
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- -1 Glycopyrronium salt Chemical class 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 229960002462 glycopyrronium bromide Drugs 0.000 description 6
- 230000008859 change Effects 0.000 description 5
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
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- 150000003839 salts Chemical group 0.000 description 3
- IFLKEBSJTZGCJG-UHFFFAOYSA-N 3-methylthiophene-2-carboxylic acid Chemical compound CC=1C=CSC=1C(O)=O IFLKEBSJTZGCJG-UHFFFAOYSA-N 0.000 description 2
- IHOXNOQMRZISPV-YJYMSZOUSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-methoxyphenyl)propan-2-yl]azaniumyl]ethyl]-2-oxo-1h-quinolin-8-olate Chemical compound 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 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- 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 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
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- 229910052751 metal Inorganic materials 0.000 description 2
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- BMKINZUHKYLSKI-DQEYMECFSA-N n-[2-hydroxy-5-[(1r)-1-hydroxy-2-[2-[4-[[(2r)-2-hydroxy-2-phenylethyl]amino]phenyl]ethylamino]ethyl]phenyl]formamide Chemical compound C1([C@@H](O)CNC2=CC=C(C=C2)CCNC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=CC=CC=C1 BMKINZUHKYLSKI-DQEYMECFSA-N 0.000 description 2
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- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- DCYGAPKNVCQNOE-UHFFFAOYSA-N 2,2,2-triphenylacetic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)O)C1=CC=CC=C1 DCYGAPKNVCQNOE-UHFFFAOYSA-N 0.000 description 1
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- BKLAJZNVMHLXAP-VKGMXUHCSA-N 3-[(1r,5s)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl]-2,2-diphenylpropanenitrile Chemical compound C([C@H]1CC[C@@H](C2)[N+]1(C)C)C2CC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 BKLAJZNVMHLXAP-VKGMXUHCSA-N 0.000 description 1
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- WDXXFDIEAANZRZ-CTTJPBLHSA-N [(3r)-1-[2-amino-1-(1,2-oxazol-3-yl)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-diphenylacetate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C(O)(C=3C=CC=CC=3)C=3C=CC=CC=3)CC[N+]12C(C(=O)N)C=1C=CON=1 WDXXFDIEAANZRZ-CTTJPBLHSA-N 0.000 description 1
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- 238000000386 microscopy Methods 0.000 description 1
- 229950001768 milveterol Drugs 0.000 description 1
- 229960002744 mometasone furoate Drugs 0.000 description 1
- WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- KCEHVJZZIGJAAW-FERBBOLQSA-N olodaterol hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(C)(C)NC[C@H](O)C1=CC(O)=CC2=C1OCC(=O)N2 KCEHVJZZIGJAAW-FERBBOLQSA-N 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960001609 oxitropium bromide Drugs 0.000 description 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 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960002288 procaterol Drugs 0.000 description 1
- FKNXQNWAXFXVNW-BLLLJJGKSA-N procaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)[C@@H](NC(C)C)CC FKNXQNWAXFXVNW-BLLLJJGKSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960004017 salmeterol Drugs 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000012903 solid bulk drug substance Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000004441 surface measurement Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical class O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 1
- 229960000257 tiotropium bromide Drugs 0.000 description 1
- MQLXPRBEAHBZTK-SEINRUQRSA-M tiotropium bromide hydrate Chemical compound O.[Br-].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 MQLXPRBEAHBZTK-SEINRUQRSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Otolaryngology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07123164 | 2007-12-13 | ||
| EP07123164.1 | 2007-12-13 | ||
| PCT/EP2008/067359 WO2009074662A2 (en) | 2007-12-13 | 2008-12-11 | Organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2708083A1 CA2708083A1 (en) | 2009-06-18 |
| CA2708083C true CA2708083C (en) | 2016-06-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2708083A Expired - Fee Related CA2708083C (en) | 2007-12-13 | 2008-12-11 | Organic compounds |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20100247658A1 (OSRAM) |
| EP (1) | EP2234595B1 (OSRAM) |
| JP (1) | JP2011506399A (OSRAM) |
| KR (1) | KR20100099281A (OSRAM) |
| CN (1) | CN101896162B (OSRAM) |
| AU (1) | AU2008334543B2 (OSRAM) |
| BR (1) | BRPI0821186A2 (OSRAM) |
| CA (1) | CA2708083C (OSRAM) |
| ES (1) | ES2396471T3 (OSRAM) |
| PL (1) | PL2234595T3 (OSRAM) |
| PT (1) | PT2234595E (OSRAM) |
| RU (1) | RU2482838C2 (OSRAM) |
| WO (1) | WO2009074662A2 (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2010253770B9 (en) * | 2009-05-29 | 2015-02-12 | Pearl Therapeutics, Inc. | Compositions for respiratory delivery of active agents and associated methods and systems |
| US9393202B2 (en) | 2013-04-26 | 2016-07-19 | Chiesi Farmaceutici S.P.A | Particle size reduction of an antimuscarinic compound |
| GB201307659D0 (en) | 2013-04-26 | 2013-06-12 | Korea Coast Guard Commissioner | Preparation of drug particles by micronisation |
| SG11201700536XA (en) | 2014-09-09 | 2017-02-27 | Vectura Ltd | Formulation comprising glycopyrrolate, method and apparatus |
| US9925168B2 (en) | 2016-01-22 | 2018-03-27 | Chiesi Farmaceutici S.P.A. | Preparation of micronized particles of an antimuscarinic compound by hydrodynamic cavitation |
| US10888500B2 (en) | 2016-07-29 | 2021-01-12 | Inke, S.A. | Particle size stabilization process |
| CN112137957B (zh) * | 2019-06-26 | 2022-07-29 | 长风药业股份有限公司 | 一种药用吸入气雾剂及其制备方法 |
| CN112972384B (zh) * | 2019-12-02 | 2022-03-18 | 长风药业股份有限公司 | 一种格隆溴铵和茚达特罗原料药微粉混合物的制备方法 |
| IT202300022716A1 (it) | 2023-10-30 | 2025-04-30 | Ind Chimica Srl | Processo di condizionamento di fluticasone furoato micronizzato |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9101090D0 (sv) * | 1991-04-11 | 1991-04-11 | Astra Ab | Process for conditioning of water-soluble substances |
| US5747002A (en) * | 1995-04-05 | 1998-05-05 | Genentech, Inc. | Preparation of sodium chloride aerosol formulations |
| US6613795B2 (en) * | 1996-11-11 | 2003-09-02 | Christian Noe | Enantiomerically pure basic arylcycloalkylhydroxycarboxylic esters, processes for their preparation and their use in medicaments |
| GB0008660D0 (en) * | 2000-04-07 | 2000-05-31 | Arakis Ltd | The treatment of respiratory diseases |
| PT2283817T (pt) * | 2000-11-30 | 2016-08-22 | Vectura Ltd | Método de fabrico de partículas para utilização numa composição farmacêutica |
| WO2005046655A1 (en) * | 2003-11-04 | 2005-05-26 | Shire Laboratories, Inc. | Sustained release of positively charged pharmacologically active molecules from a matrix containing polymers with polarized oxygen atoms |
| KR101179393B1 (ko) * | 2004-03-23 | 2012-09-07 | 노파르티스 아게 | 제약 조성물 |
| GB0409703D0 (en) * | 2004-04-30 | 2004-06-02 | Vectura Ltd | Pharmaceutical compositions |
| WO2006073154A1 (ja) * | 2005-01-07 | 2006-07-13 | Eisai R&D Management Co., Ltd. | 医薬組成物及びその製造方法 |
| GB0613161D0 (en) * | 2006-06-30 | 2006-08-09 | Novartis Ag | Organic Compounds |
-
2008
- 2008-12-11 EP EP08859423A patent/EP2234595B1/en active Active
- 2008-12-11 CN CN2008801205425A patent/CN101896162B/zh not_active Expired - Fee Related
- 2008-12-11 KR KR1020107015330A patent/KR20100099281A/ko not_active Ceased
- 2008-12-11 US US12/745,790 patent/US20100247658A1/en not_active Abandoned
- 2008-12-11 ES ES08859423T patent/ES2396471T3/es active Active
- 2008-12-11 RU RU2010128246/15A patent/RU2482838C2/ru not_active IP Right Cessation
- 2008-12-11 WO PCT/EP2008/067359 patent/WO2009074662A2/en not_active Ceased
- 2008-12-11 CA CA2708083A patent/CA2708083C/en not_active Expired - Fee Related
- 2008-12-11 AU AU2008334543A patent/AU2008334543B2/en not_active Ceased
- 2008-12-11 JP JP2010537455A patent/JP2011506399A/ja active Pending
- 2008-12-11 PL PL08859423T patent/PL2234595T3/pl unknown
- 2008-12-11 BR BRPI0821186-8A patent/BRPI0821186A2/pt not_active IP Right Cessation
- 2008-12-11 PT PT88594239T patent/PT2234595E/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009074662A3 (en) | 2009-09-24 |
| EP2234595A2 (en) | 2010-10-06 |
| ES2396471T3 (es) | 2013-02-21 |
| RU2482838C2 (ru) | 2013-05-27 |
| CN101896162B (zh) | 2013-06-05 |
| PT2234595E (pt) | 2013-01-24 |
| CN101896162A (zh) | 2010-11-24 |
| RU2010128246A (ru) | 2012-01-20 |
| CA2708083A1 (en) | 2009-06-18 |
| BRPI0821186A2 (pt) | 2015-06-16 |
| AU2008334543B2 (en) | 2011-07-28 |
| WO2009074662A2 (en) | 2009-06-18 |
| EP2234595B1 (en) | 2012-11-28 |
| AU2008334543A1 (en) | 2009-06-18 |
| JP2011506399A (ja) | 2011-03-03 |
| PL2234595T3 (pl) | 2013-04-30 |
| KR20100099281A (ko) | 2010-09-10 |
| US20100247658A1 (en) | 2010-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20131211 |
|
| MKLA | Lapsed |
Effective date: 20181211 |