CA2757418C - Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making the same - Google Patents
Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making the same Download PDFInfo
- Publication number
- CA2757418C CA2757418C CA2757418A CA2757418A CA2757418C CA 2757418 C CA2757418 C CA 2757418C CA 2757418 A CA2757418 A CA 2757418A CA 2757418 A CA2757418 A CA 2757418A CA 2757418 C CA2757418 C CA 2757418C
- Authority
- CA
- Canada
- Prior art keywords
- making
- methods
- same
- pharmaceutical formulations
- derivatives
- 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.)
- Active
Links
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
- A61K31/435—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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
-
- 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
- A61K31/4415—Pyridoxine, i.e. Vitamin B6
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
-
- 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
- A61K9/20—Pills, tablets, discs, rods
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychology (AREA)
- Inorganic Chemistry (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16579409P | 2009-04-01 | 2009-04-01 | |
| US61/165,794 | 2009-04-01 | ||
| PCT/PT2010/000015 WO2010114405A2 (en) | 2009-04-01 | 2010-03-31 | Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2757418A1 CA2757418A1 (en) | 2010-10-07 |
| CA2757418C true CA2757418C (en) | 2021-06-15 |
Family
ID=42229943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2757418A Active CA2757418C (en) | 2009-04-01 | 2010-03-31 | Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making the same |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US20100256194A1 (https=) |
| EP (1) | EP2413913B1 (https=) |
| JP (2) | JP5864410B2 (https=) |
| KR (1) | KR101824257B1 (https=) |
| CN (2) | CN102438595B (https=) |
| AU (1) | AU2010231962B2 (https=) |
| BR (1) | BRPI1016132B8 (https=) |
| CA (1) | CA2757418C (https=) |
| DK (1) | DK2413913T3 (https=) |
| ES (1) | ES2915698T3 (https=) |
| MX (1) | MX361618B (https=) |
| PL (1) | PL2413913T3 (https=) |
| PT (1) | PT2413913T (https=) |
| RU (1) | RU2550133C2 (https=) |
| WO (1) | WO2010114405A2 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL1907382T3 (pl) | 2005-07-26 | 2016-01-29 | Bial Portela & Ca Sa | Pochodne nitrokatecholowe jako inhibitory COMT |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| BRPI0721213B1 (pt) | 2007-01-31 | 2021-11-09 | Bial - Portela & Ca, S.A. | Uso de nitrocatecóis substituídos, e embalagem |
| WO2009116882A1 (en) | 2008-03-17 | 2009-09-24 | Portela & Ca., S.A. | Crystal forms of 5- [3- (2, 5-dichloro-4, 6-dimethyl-1-oxy-pyridine-3-yl) [1,2,3] oxadiazol-5-yl] -3-nit robenzene-1, 2-diol |
| PT2413912T (pt) | 2009-04-01 | 2019-06-11 | Bial Portela & Ca Sa | Formulações farmacêuticas compreendendo derivados de nitrocatecol e métodos para as produzir |
| US20140045900A1 (en) * | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| JP6456143B2 (ja) | 2011-12-13 | 2019-01-23 | ノヴィファーマ,エス.アー. | カテコール−o−メチル転移酵素阻害剤を調製するための中間体として有用な化学的化合物 |
| NO2699580T3 (https=) | 2014-01-24 | 2018-02-24 | ||
| RU2017120184A (ru) | 2014-11-28 | 2018-12-28 | БИАЛ - ПОРТЕЛА ЭНД Ка, С.А. | Лекарства для замедления течения болезни паркинсона |
| US20210087183A1 (en) * | 2017-12-18 | 2021-03-25 | Unichem Laboratories Ltd | Process for the preparation of opicapone and intermediates thereof |
| HUE070049T2 (hu) | 2018-03-01 | 2025-05-28 | Astrazeneca Ab | (2S)-{(1S)-1-ciano-2-[4-(3-metil-2-oxo-2,3-dihidro-1,3-benzoxazol-5-il)fenil]etil} -1,4-oxazepán-2-karboxamidot tartalmazó gyógyászati készítmények |
| WO2020018547A1 (en) | 2018-07-17 | 2020-01-23 | Insmed Incorporated | Certain (2s)-n-[(1s)-1-cyano-2-phenylethyl]-1,4-oxazepane-2-carboxamides for treating lupus nephritis |
| EP3860602A1 (en) | 2018-10-05 | 2021-08-11 | Neurocrine Biosciences, Inc. | Methods for the administration of comt inhibitors |
| WO2020072886A1 (en) | 2018-10-05 | 2020-04-09 | Neurocrine Biosciences, Inc. | Methods for the administration of comt inhibitors |
| WO2021182981A1 (en) | 2020-03-13 | 2021-09-16 | BIAL - PORTELA & Cª, S.A. | Micronised opicapone |
| GB202011709D0 (en) | 2020-07-28 | 2020-09-09 | Bial Portela & Ca Sa | Solid dispersion of opicapone |
| GB202016425D0 (en) | 2020-10-16 | 2020-12-02 | Bial Portela & Ca Sa | Treatment regimens for parkinson's disease |
| EP4262798A1 (en) | 2020-12-17 | 2023-10-25 | Bial-Portela & CA, S.A. | Treatment regimens for early idiopathic parkinson's disease |
| US20240300930A1 (en) * | 2021-02-26 | 2024-09-12 | Msn Laboratories Private Limited, R&D Center | Novel process for the preparation of 2,5-dichloro-3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-4,6-dimethylpyridine-1-oxide |
| GB202212082D0 (en) | 2022-08-18 | 2022-10-05 | Bial Portela & Ca Sa | Treatment regimens for parkinson's disease |
| JP2026503035A (ja) | 2023-01-06 | 2026-01-27 | インスメッド インコーポレイテッド | 新規な可逆性dpp1阻害剤及びその用途 |
| EP4719374A1 (en) | 2023-05-25 | 2026-04-08 | Bial-Portela & CA, S.A. | Treatment regimens for early idiopathic parkinson's disease |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1532178A (en) * | 1921-07-25 | 1925-04-07 | Louis A Godbold | Lubricator |
| US3647809A (en) * | 1968-04-26 | 1972-03-07 | Chinoin Gyogyszer Es Vegyeszet | Certain pyridyl-1 2 4-oxadiazole derivatives |
| US4085563A (en) * | 1977-01-31 | 1978-04-25 | Campbell Soup Company | Cookie dispensing apparatus |
| US4264573A (en) * | 1979-05-21 | 1981-04-28 | Rowell Laboratories, Inc. | Pharmaceutical formulation for slow release via controlled surface erosion |
| US4368668A (en) * | 1981-05-15 | 1983-01-18 | Veb Kombinat Polygraph "Werner Lamberz" Leipzig | Printing plate mounting arrangement |
| US5236952A (en) * | 1986-03-11 | 1993-08-17 | Hoffmann-La Roche Inc. | Catechol derivatives |
| YU213587A (en) * | 1986-11-28 | 1989-06-30 | Orion Yhtymae Oy | Process for obtaining new pharmacologic active cateholic derivatives |
| US6361794B1 (en) * | 1996-06-12 | 2002-03-26 | Basf Corporation | Method of making ibuprofen and narcotic analgesic composition |
| US6206110B1 (en) * | 1996-09-09 | 2001-03-27 | Smith International, Inc. | Protected lubricant reservoir with pressure control for sealed bearing earth boring drill bit |
| JP2002526482A (ja) * | 1998-09-18 | 2002-08-20 | バーテックス ファーマシューティカルズ インコーポレイテッド | p38のインヒビター |
| GB2344819A (en) * | 1998-12-18 | 2000-06-21 | Portela & Ca Sa | 2-Phenyl-1-(3,4-dihydroxy-5-nitrophenyl)-1-ethanones |
| US6660753B2 (en) * | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| JP2004532611A (ja) * | 2000-11-28 | 2004-10-28 | ザイモジェネティクス,インコーポレイティド | サイトカイン受容体zcytor19 |
| US20040097555A1 (en) * | 2000-12-26 | 2004-05-20 | Shinegori Ohkawa | Concomitant drugs |
| WO2002060446A1 (fr) * | 2001-01-29 | 2002-08-08 | Shionogi & Co., Ltd. | Preparation medicamenteuse contenant du 5-methyle-1-phenyle-2-(1h)-pyridone en tant que principe actif |
| JP2005504014A (ja) * | 2001-06-08 | 2005-02-10 | サイトビア インコーポレイテッド | カスパーゼの活性化因子およびアポトーシスの誘導因子としての置換された3−アリール−5−アリール−[1,2,4]−オキサジアゾール類および類似体、並びにその使用法 |
| CN100364531C (zh) * | 2002-12-18 | 2008-01-30 | 西托维亚公司 | 3,5-二取代-[1,2,4]-二唑及类似物和其用途 |
| WO2005006945A2 (en) * | 2003-07-03 | 2005-01-27 | The Salk Institute For Biological Studies | Methods for treating neural disorders and compounds useful therefor |
| WO2005030176A1 (en) * | 2003-09-29 | 2005-04-07 | Novo Nordisk Femcare Ag | Improved stability of progestogen formulations |
| US7300406B2 (en) * | 2003-09-30 | 2007-11-27 | Carter Vandette B | Medical examination apparatus |
| GB0325956D0 (en) * | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
| WO2005105780A2 (en) * | 2004-04-28 | 2005-11-10 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of rock and other protein kinases |
| EP1625849A1 (en) * | 2004-08-09 | 2006-02-15 | Liconsa, Liberacion Controlada de Sustancias Activas, S.A. | Pharmaceutical composition comprising drospirenone and ethynylestradiol |
| GB0510143D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds A1 |
| US20080051441A1 (en) * | 2004-12-28 | 2008-02-28 | Astrazeneca Ab | Aryl Sulphonamide Modulators |
| US20060257473A1 (en) * | 2005-05-11 | 2006-11-16 | Porranee Puranajoti | Extended release tablet |
| US7553964B2 (en) * | 2005-06-03 | 2009-06-30 | Abbott Laboratories | Cyclobutyl amine derivatives |
| JP2007024970A (ja) * | 2005-07-12 | 2007-02-01 | Miyakawa:Kk | 液晶表示装置の開口効率を上昇させるための樹脂レンズ製造法及びその製造装置 |
| PL1907382T3 (pl) * | 2005-07-26 | 2016-01-29 | Bial Portela & Ca Sa | Pochodne nitrokatecholowe jako inhibitory COMT |
| US20070048384A1 (en) * | 2005-08-26 | 2007-03-01 | Joerg Rosenberg | Pharmaceutical compositions |
| EP1845097A1 (en) * | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| JP2008162955A (ja) * | 2006-12-28 | 2008-07-17 | Chugai Pharmaceut Co Ltd | バリン含有高密度顆粒剤 |
| BRPI0721213B1 (pt) * | 2007-01-31 | 2021-11-09 | Bial - Portela & Ca, S.A. | Uso de nitrocatecóis substituídos, e embalagem |
| AR065802A1 (es) * | 2007-03-22 | 2009-07-01 | Schering Corp | Formulaciones de comprimidos que contienen sales de 8- [( 1- ( 3,5- bis- (trifluorometil) fenil) -etoxi ) - metil) -8- fenil -1, 7- diaza- spiro [ 4,5] decan -2- ona y comprimidos elaborados a partir de estas |
| WO2009116882A1 (en) * | 2008-03-17 | 2009-09-24 | Portela & Ca., S.A. | Crystal forms of 5- [3- (2, 5-dichloro-4, 6-dimethyl-1-oxy-pyridine-3-yl) [1,2,3] oxadiazol-5-yl] -3-nit robenzene-1, 2-diol |
-
2010
- 2010-03-31 BR BRPI1016132A patent/BRPI1016132B8/pt active IP Right Grant
- 2010-03-31 MX MX2011010311A patent/MX361618B/es active IP Right Grant
- 2010-03-31 JP JP2012503351A patent/JP5864410B2/ja active Active
- 2010-03-31 PT PT107143869T patent/PT2413913T/pt unknown
- 2010-03-31 CN CN201080022455.3A patent/CN102438595B/zh active Active
- 2010-03-31 RU RU2011143619/15A patent/RU2550133C2/ru active IP Right Revival
- 2010-03-31 ES ES10714386T patent/ES2915698T3/es active Active
- 2010-03-31 AU AU2010231962A patent/AU2010231962B2/en active Active
- 2010-03-31 WO PCT/PT2010/000015 patent/WO2010114405A2/en not_active Ceased
- 2010-03-31 PL PL10714386.9T patent/PL2413913T3/pl unknown
- 2010-03-31 DK DK10714386.9T patent/DK2413913T3/da active
- 2010-03-31 KR KR1020117025867A patent/KR101824257B1/ko active Active
- 2010-03-31 CN CN201610184873.1A patent/CN105816456A/zh active Pending
- 2010-03-31 CA CA2757418A patent/CA2757418C/en active Active
- 2010-03-31 EP EP10714386.9A patent/EP2413913B1/en active Active
- 2010-03-31 US US12/750,957 patent/US20100256194A1/en not_active Abandoned
-
2015
- 2015-08-27 JP JP2015168153A patent/JP6336420B2/ja active Active
-
2018
- 2018-09-05 US US16/122,643 patent/US20190008774A1/en not_active Abandoned
-
2020
- 2020-12-15 US US17/122,013 patent/US20210315824A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| MX361618B (es) | 2018-12-13 |
| PL2413913T3 (pl) | 2022-09-26 |
| US20100256194A1 (en) | 2010-10-07 |
| BRPI1016132B8 (pt) | 2021-05-25 |
| CN105816456A (zh) | 2016-08-03 |
| EP2413913A2 (en) | 2012-02-08 |
| RU2011143619A (ru) | 2013-05-10 |
| KR101824257B1 (ko) | 2018-01-31 |
| AU2010231962A1 (en) | 2011-11-17 |
| JP5864410B2 (ja) | 2016-02-17 |
| US20190008774A1 (en) | 2019-01-10 |
| WO2010114405A2 (en) | 2010-10-07 |
| CA2757418A1 (en) | 2010-10-07 |
| BRPI1016132A2 (pt) | 2016-04-19 |
| MX2011010311A (es) | 2012-03-07 |
| EP2413913B1 (en) | 2022-05-18 |
| KR20120008040A (ko) | 2012-01-25 |
| CN102438595A (zh) | 2012-05-02 |
| JP6336420B2 (ja) | 2018-06-06 |
| DK2413913T3 (da) | 2022-06-13 |
| JP2012522764A (ja) | 2012-09-27 |
| WO2010114405A3 (en) | 2011-01-06 |
| PT2413913T (pt) | 2022-06-09 |
| JP2016020369A (ja) | 2016-02-04 |
| CN102438595B (zh) | 2016-04-27 |
| RU2550133C2 (ru) | 2015-05-10 |
| ES2915698T3 (es) | 2022-06-24 |
| BRPI1016132B1 (pt) | 2020-11-24 |
| AU2010231962B2 (en) | 2015-05-21 |
| US20210315824A1 (en) | 2021-10-14 |
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