CA2668689C - Substituted 3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2h-pyrido[2,1-a]isoquinolin-2-ol compounds and methods relating thereto - Google Patents
Substituted 3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2h-pyrido[2,1-a]isoquinolin-2-ol compounds and methods relating thereto Download PDFInfo
- Publication number
- CA2668689C CA2668689C CA2668689A CA2668689A CA2668689C CA 2668689 C CA2668689 C CA 2668689C CA 2668689 A CA2668689 A CA 2668689A CA 2668689 A CA2668689 A CA 2668689A CA 2668689 C CA2668689 C CA 2668689C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- dimethoxy
- hexahydro
- pyrido
- isoquinolin
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86494406P | 2006-11-08 | 2006-11-08 | |
| US60/864,944 | 2006-11-08 | ||
| PCT/US2007/084176 WO2008058261A1 (en) | 2006-11-08 | 2007-11-08 | Substituted 3-isobutyl-9, 10-dimethoxy-1,3,4,6,7,11b-hexahydro-2h-pyrido[2,1-a] isoquinolin-2-ol compounds and methods relating thereto |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2668689A1 CA2668689A1 (en) | 2008-05-15 |
| CA2668689C true CA2668689C (en) | 2015-12-29 |
Family
ID=39110526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2668689A Active CA2668689C (en) | 2006-11-08 | 2007-11-08 | Substituted 3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2h-pyrido[2,1-a]isoquinolin-2-ol compounds and methods relating thereto |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US8039627B2 (index.php) |
| EP (1) | EP2081929B1 (index.php) |
| JP (1) | JP5290185B2 (index.php) |
| KR (1) | KR101500766B1 (index.php) |
| CN (1) | CN101553487B (index.php) |
| AU (1) | AU2007317242B2 (index.php) |
| BR (1) | BRPI0718247B1 (index.php) |
| CA (1) | CA2668689C (index.php) |
| DK (1) | DK2081929T3 (index.php) |
| EA (1) | EA018378B1 (index.php) |
| ES (1) | ES2402220T3 (index.php) |
| IL (1) | IL198250A0 (index.php) |
| MX (1) | MX2009004910A (index.php) |
| PL (1) | PL2081929T3 (index.php) |
| PT (1) | PT2081929E (index.php) |
| WO (1) | WO2008058261A1 (index.php) |
Families Citing this family (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101500766B1 (ko) | 2006-11-08 | 2015-03-16 | 뉴로크린 바이오사이언시즈 인코퍼레이티드 | 치환된 3-이소부틸-9,10-디메톡시-1,3,4,6,7,11ｂ-헥사히드로-2Ｈ-피리도[2,1-ａ]이소퀴놀린-2-올 화합물 및 그와 관련된 방법 |
| CN102186848B (zh) | 2008-09-18 | 2014-11-12 | 奥斯拜客斯制药有限公司 | 囊泡单胺转运体2的苯并喹啉抑制剂 |
| CN103003275A (zh) * | 2010-06-01 | 2013-03-27 | 奥斯拜客斯制药有限公司 | Vmat2的苯并喹啉酮抑制剂 |
| WO2012000308A1 (zh) * | 2010-06-29 | 2012-01-05 | 中国药科大学 | 丁苯那嗪的拆分方法 |
| US8351329B2 (en) * | 2010-09-14 | 2013-01-08 | Cisco Technology, Inc. | Universal load-balancing tunnel encapsulation |
| CN102285984B (zh) * | 2010-11-25 | 2012-10-10 | 江苏威凯尔医药科技有限公司 | (2R,3R,11bR)-二氢丁苯那嗪及相关化合物的制备方法 |
| WO2012081031A1 (en) | 2010-12-15 | 2012-06-21 | Enaltec Labs Pvt. Ltd. | Process for preparing tetrabenazine |
| US9550780B2 (en) | 2012-09-18 | 2017-01-24 | Auspex Pharmaceuticals, Inc. | Formulations pharmacokinetics of deuterated benzoquinoline inhibitors of vesicular monoamine transporter 2 |
| EP2897615A4 (en) | 2012-09-18 | 2016-04-27 | Auspex Pharmaceuticals Inc | PHARMACOKINETIC FORMULATIONS OF DEUTERATED BENZOCHINOL INHIBITORS OF THE VESICLE MONOAMINE TRANSPORTER 2 |
| EP2951178A4 (en) | 2013-01-31 | 2016-07-06 | Auspex Pharmaceuticals Inc | VMAT2 INHIBITORS OF BENZOQUINOLONE TYPE |
| HK1221645A1 (zh) * | 2013-09-27 | 2017-06-09 | Auspex Pharmaceuticals, Inc. | Vmat2的苯并喹啉抑制剂 |
| CA2930744A1 (en) * | 2013-12-03 | 2015-06-11 | Auspex Pharmaceuticals, Inc. | Methods of manufacturing benzoquinoline compounds |
| AU2015209330A1 (en) * | 2014-01-27 | 2016-07-28 | Auspex Pharmaceuticals, Inc. | Benzoquinoline inhibitors of vesicular monoamine transporter 2 |
| EP4049681B1 (en) * | 2014-02-07 | 2026-01-07 | Neurocrine Biosciences, Inc. | Pharmaceutical compositions comprising an antipsychotic drug and a vmat2 inhibitor and uses thereof |
| US10166183B2 (en) | 2014-02-07 | 2019-01-01 | Auspex Pharmaceuticals, Inc. | Pharmaceutical formulations |
| CN111454188A (zh) | 2014-02-13 | 2020-07-28 | 因赛特公司 | 作为lsd1抑制剂的环丙胺 |
| LT3139925T (lt) * | 2014-05-06 | 2022-01-25 | Neurocrine Biosciences, Inc. | Valbenazino dozavimo režimas, skirtas gydyti hiperkinetinio judėjimo sutrikimus |
| AU2016215033B2 (en) * | 2015-02-06 | 2020-06-25 | Neurocrine Biosciences, Inc. | (9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido-[2,1-a]isoquinolin-2-yl]methanol and compounds, compositions and methods relating thereto |
| HK1249860A1 (zh) | 2015-03-06 | 2018-11-16 | 奥斯拜客斯制药有限公司 | 用於治疗异常不自主运动障碍的方法 |
| KR102659373B1 (ko) | 2015-04-03 | 2024-04-23 | 인사이트 홀딩스 코포레이션 | Lsd1 저해제로서 헤테로사이클릭 화합물 |
| CA2990194A1 (en) | 2015-06-23 | 2016-12-29 | Neurocrine Biosciences, Inc. | Vmat2 inhibitors for treating neurological diseases or disorders |
| MX389824B (es) | 2015-08-12 | 2025-03-20 | Incyte Holdings Corp | Sales de un inhibidor de dimetilasa 1 especifica para lisina (lsd1). |
| MX383906B (es) | 2015-10-09 | 2025-03-14 | Teva Pharmaceuticals Int Gmbh | Combinación de levodopa deuterado con carbidopa y opicapona para el tratamiento del mal de parkinson |
| LT3875459T (lt) | 2015-10-30 | 2024-02-26 | Neurocrine Biosciences, Inc. | Valbenazino dihidrochlorido druskos ir jų polimorfai |
| MA44127A (fr) | 2015-12-23 | 2018-10-31 | Neurocrine Biosciences Inc | Procédés de synthèse pour la préparation de di(4-méthylbenzènesulfonate) de 2-amino-3-méthylbutanoate de (s)-(2r,3r,11br)-3-isobutyl-9,10-diméthoxy-2,3,4,6,7,11b-hexahydro-1h-pyrido[2,1,-a]isoquinoléin-2-yl |
| US10479787B2 (en) | 2016-04-22 | 2019-11-19 | Lupin Limited | Process for preparation of tetrabenazine and deutetrabenazine |
| ES2811048T3 (es) | 2016-06-29 | 2021-03-10 | Crystal Pharmaceutical Suzhou Co Ltd | Formas cristalinas de NBI-98854, método de preparación para las mismas y uso de las mismas |
| US11242341B2 (en) | 2016-10-06 | 2022-02-08 | Assia Chemical Industries Ltd. | Solid state forms of valbenazine |
| JP2020500875A (ja) | 2016-12-02 | 2020-01-16 | ニューロクライン バイオサイエンシーズ，インコーポレイテッド | 統合失調症または統合失調感情障害を処置するためのバルベナジンの使用 |
| EP3568394A1 (en) | 2017-01-10 | 2019-11-20 | Sandoz AG | Crystalline valbenazine free base |
| JP7199359B2 (ja) * | 2017-01-27 | 2023-01-05 | ニューロクライン バイオサイエンシーズ，インコーポレイテッド | 特定のｖｍａｔ２インヒビターを投与するための方法 |
| EP3585787A1 (en) | 2017-02-27 | 2020-01-01 | Sandoz AG | Crystalline forms of valbenazine salts |
| WO2018164996A1 (en) | 2017-03-06 | 2018-09-13 | Neurocrine Biosciences, Inc. | Dosing regimen for valbenazine |
| EP3596077A1 (en) | 2017-03-15 | 2020-01-22 | Auspex Pharmaceuticals, Inc. | Analogs of deutetrabenazine, their preparation and use |
| EP3606530A2 (en) * | 2017-04-01 | 2020-02-12 | Adeptio Pharmaceuticals Limited | Dihydrotetrabenazine for use in the treatment a movement disorder |
| GB201705306D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705305D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705304D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705303D0 (en) * | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705302D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| JOP20190239A1 (ar) | 2017-04-19 | 2019-10-09 | Neurocrine Biosciences Inc | مركبات مثبطة لـ vmat2 وتركيبات منها |
| US20200179352A1 (en) | 2017-04-26 | 2020-06-11 | Neurocrine Biosciences, Inc. | Use of valbenazine for treating levodopa-induced dyskinesia |
| IL273300B2 (en) | 2017-09-21 | 2024-06-01 | Neurocrine Biosciences Inc | High dose valbenazine formulation and related preparations, methods and kits |
| KR20200066661A (ko) * | 2017-10-10 | 2020-06-10 | 뉴로크린 바이오사이언시즈 인코퍼레이티드 | 특정 vmat2 억제제의 투여 방법 |
| KR20250070134A (ko) | 2017-10-10 | 2025-05-20 | 뉴로크린 바이오사이언시즈 인코퍼레이티드 | 특정 vmat2 억제제의 투여 방법 |
| KR20210004939A (ko) * | 2017-11-08 | 2021-01-13 | 포시 파마슈티컬스 컴퍼니 리미티드 | 다이하이드로테트라베나진의 에스터 |
| US11384077B2 (en) | 2017-11-22 | 2022-07-12 | Assia Chemical Industries Ltd. | Solid state form of Valbenazine |
| JP7212958B2 (ja) | 2017-12-26 | 2023-01-26 | ▲蘇▼州科睿思制▲葯▼有限公司 | バルベナジントシル酸塩の結晶形及びその製造方法並びに用途 |
| CN110092785A (zh) * | 2018-01-31 | 2019-08-06 | 广东东阳光药业有限公司 | 一种丁苯那嗪的动态拆分方法 |
| GB201808464D0 (en) | 2018-05-23 | 2018-07-11 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compounds for use in treating huntington's disease |
| KR20210021006A (ko) | 2018-06-14 | 2021-02-24 | 뉴로크린 바이오사이언시즈 인코퍼레이티드 | Vmat2 억제제 화합물, 조성물 및 그와 관련된 방법 |
| CA3104693A1 (en) | 2018-08-15 | 2020-02-20 | Neurocrine Biosciences, Inc. | Methods for the administration of certain vmat2 inhibitors |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
| EP3860599B1 (en) | 2018-10-04 | 2024-05-15 | Adeptio Pharmaceuticals Limited | (+)-alpha-dihydrotetrabenazine dosage regimen for treating movement disorders |
| CA3065236A1 (en) | 2018-12-27 | 2020-06-27 | Apotex Inc. | Novel crystalline form of valbenazine dibesylate |
| WO2020213014A1 (en) | 2019-04-19 | 2020-10-22 | Mylan Laboratories Limited | An improved process for the preparation of valbenazine and its salts |
| US10689380B1 (en) | 2019-07-30 | 2020-06-23 | Farmhispania S.A. | Crystalline forms of valbenazine ditosylate |
| AU2020327501B2 (en) * | 2019-08-12 | 2026-02-05 | Geneora Pharma (Shijiazhuang) Co., Ltd. | VMAT2 inhibitor and preparation method therefor and application thereof |
| US10940141B1 (en) | 2019-08-23 | 2021-03-09 | Neurocrine Biosciences, Inc. | Methods for the administration of certain VMAT2 inhibitors |
| US20220363680A1 (en) | 2019-09-13 | 2022-11-17 | Neurocrine Biosciences, Inc. | Processes for the synthesis of valbenazine |
| CN110698397A (zh) * | 2019-10-28 | 2020-01-17 | 南京红杉生物科技有限公司 | 丁苯那嗪中间体及其合成方法、应用和合成用中间产物 |
| CR20230448A (es) | 2021-03-22 | 2023-10-27 | Neurocrine Biosciences Inc | Inhibidores de vmat2 y métodos de uso |
| WO2022232060A1 (en) | 2021-04-26 | 2022-11-03 | Neurocrine Biosciences, Inc. | Processes for the synthesis of valbenazine |
| BR112023026160A2 (pt) | 2021-06-30 | 2024-03-05 | Neurocrine Biosciences Inc | Valbenazina para uso no tratamento de discinesia devido à paralisia cerebral |
| WO2023278987A1 (en) | 2021-06-30 | 2023-01-05 | Neurocrine Biosciences, Inc. | Valbenazine for use in the add-on treatment of schizophrenia |
| WO2023172849A1 (en) | 2022-03-07 | 2023-09-14 | Neurocrine Biosciences, Inc. | Valbenazine, a vmat2 inhibitor, as a free base a tosylate or ditosylate salt, for use in the treatment of chorea associated with huntington's disease |
| CA3267926A1 (en) | 2022-09-21 | 2024-03-28 | Neurocrine Biosciences, Inc. | HEXAHYDRO-2H-PYRIDO[2,1-A]ISOQUINOLINE VMAT2 INHIBITORS AND METHODS OF USE |
| WO2025038959A1 (en) | 2023-08-17 | 2025-02-20 | Neurocrine Biosciences, Inc. | Methods for the administration of certain vmat2 inhibitors |
| TW202521119A (zh) | 2023-08-17 | 2025-06-01 | 美商紐羅克里生物科學有限公司 | 用於投與特定vmat2抑制劑之方法 |
| WO2025096823A1 (en) | 2023-11-01 | 2025-05-08 | Neurocrine Biosciences, Inc. | Improvement, maintenance or reduction of decline of motor function associated with huntington disease using valbenazine |
| WO2025188830A1 (en) | 2024-03-06 | 2025-09-12 | Neurocrine Biosciences, Inc. | Methods for the administration of certain vmat2 inhibitors |
| WO2025199234A1 (en) | 2024-03-20 | 2025-09-25 | Neurocrine Biosciences, Inc. | Vmat2 inhibitors and methods of use |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2843591A (en) | 1958-07-15 | Method for preparing same | ||
| US3209005A (en) | 1965-09-28 | Hexahydro-llbh-benzo[a] quinolizines and processes therefor | ||
| US2852518A (en) | 1957-05-23 | 1958-09-16 | Parke Davis & Co | Di-substituted quinoline compounds |
| WO1991016920A1 (en) | 1990-05-07 | 1991-11-14 | Vical, Inc. | Lipid prodrugs of salicylate and nonsteroidal anti-inflammatory drugs |
| US6610841B1 (en) | 1997-12-18 | 2003-08-26 | Gilead Sciences, Inc. | Nucleotide-based prodrugs |
| US7045543B2 (en) | 2001-11-05 | 2006-05-16 | Enzrel Inc. | Covalent conjugates of biologically-active compounds with amino acids and amino acid derivatives for targeting to physiologically-protected sites |
| GB2410947B (en) | 2004-02-11 | 2008-09-17 | Cambridge Lab Ltd | Pharmaceutical compounds |
| WO2006053067A2 (en) | 2004-11-09 | 2006-05-18 | Prestwick Pharmaceuticals, Inc. | Combination of amantadine and a tetrabenazine compound for treating hyperkinetic disorders |
| AU2006266229B2 (en) | 2005-06-29 | 2013-02-21 | The Trustees Of Columbia University In The City Of New York | Use of DTBZ for imaging endocrine pancreas and beta cell mass in type 1 diabetes |
| GB0514501D0 (en) | 2005-07-14 | 2005-08-24 | Cambridge Lab Ireland Ltd | Pharmaceutical compounds |
| GB0516168D0 (en) | 2005-08-05 | 2005-09-14 | Cambridge Lab Ireland Ltd | Pharmaceutical compounds |
| RS50807B (sr) | 2005-08-06 | 2010-08-31 | Biovail Laboratories International (Barbados) Srl. | 3,11 b-cis-dihidrotetrabenazin za lečenje šizofrenije i drugih psihoza |
| KR101500766B1 (ko) | 2006-11-08 | 2015-03-16 | 뉴로크린 바이오사이언시즈 인코퍼레이티드 | 치환된 3-이소부틸-9,10-디메톡시-1,3,4,6,7,11ｂ-헥사히드로-2Ｈ-피리도[2,1-ａ]이소퀴놀린-2-올 화합물 및 그와 관련된 방법 |
-
2007
- 2007-11-08 KR KR1020097011731A patent/KR101500766B1/ko active Active
- 2007-11-08 MX MX2009004910A patent/MX2009004910A/es active IP Right Grant
- 2007-11-08 BR BRPI0718247-3A patent/BRPI0718247B1/pt active IP Right Grant
- 2007-11-08 CN CN2007800395790A patent/CN101553487B/zh active Active
- 2007-11-08 PT PT78641602T patent/PT2081929E/pt unknown
- 2007-11-08 ES ES07864160T patent/ES2402220T3/es active Active
- 2007-11-08 EA EA200970461A patent/EA018378B1/ru unknown
- 2007-11-08 WO PCT/US2007/084176 patent/WO2008058261A1/en not_active Ceased
- 2007-11-08 CA CA2668689A patent/CA2668689C/en active Active
- 2007-11-08 JP JP2009536493A patent/JP5290185B2/ja active Active
- 2007-11-08 DK DK07864160.2T patent/DK2081929T3/da active
- 2007-11-08 PL PL07864160T patent/PL2081929T3/pl unknown
- 2007-11-08 US US11/937,445 patent/US8039627B2/en active Active
- 2007-11-08 EP EP07864160A patent/EP2081929B1/en active Active
- 2007-11-08 AU AU2007317242A patent/AU2007317242B2/en active Active
-
2009
- 2009-04-21 IL IL198250A patent/IL198250A0/en active IP Right Grant
-
2011
- 2011-09-20 US US13/237,709 patent/US8357697B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20120077839A1 (en) | 2012-03-29 |
| BRPI0718247B1 (pt) | 2021-09-21 |
| DK2081929T3 (da) | 2013-04-15 |
| IL198250A0 (en) | 2009-12-24 |
| EA200970461A1 (ru) | 2009-12-30 |
| ES2402220T8 (es) | 2021-12-23 |
| AU2007317242A1 (en) | 2008-05-15 |
| WO2008058261A1 (en) | 2008-05-15 |
| EP2081929A1 (en) | 2009-07-29 |
| US8039627B2 (en) | 2011-10-18 |
| US8357697B2 (en) | 2013-01-22 |
| MX2009004910A (es) | 2009-07-24 |
| BRPI0718247A2 (pt) | 2014-01-07 |
| EP2081929B1 (en) | 2013-01-09 |
| ES2402220T3 (es) | 2013-04-29 |
| CA2668689A1 (en) | 2008-05-15 |
| PL2081929T3 (pl) | 2013-06-28 |
| KR101500766B9 (ko) | 2024-09-25 |
| KR20090079257A (ko) | 2009-07-21 |
| AU2007317242B2 (en) | 2013-08-01 |
| CN101553487A (zh) | 2009-10-07 |
| EA018378B1 (ru) | 2013-07-30 |
| CN101553487B (zh) | 2012-06-13 |
| PT2081929E (pt) | 2013-04-15 |
| KR101500766B1 (ko) | 2015-03-16 |
| JP5290185B2 (ja) | 2013-09-18 |
| JP2010509366A (ja) | 2010-03-25 |
| US20080167337A1 (en) | 2008-07-10 |
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