CN102137847B - 作为mek激酶抑制剂的二环杂环 - Google Patents
作为mek激酶抑制剂的二环杂环 Download PDFInfo
- Publication number
- CN102137847B CN102137847B CN200980133788.0A CN200980133788A CN102137847B CN 102137847 B CN102137847 B CN 102137847B CN 200980133788 A CN200980133788 A CN 200980133788A CN 102137847 B CN102137847 B CN 102137847B
- Authority
- CN
- China
- Prior art keywords
- fluoro
- alkyl
- carboxylic acid
- formula
- mmol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 0 C*(C)(c1ccc(C)cc1N)c1c(*=O)c(OC)cc(N)c1C=O Chemical compound C*(C)(c1ccc(C)cc1N)c1c(*=O)c(OC)cc(N)c1C=O 0.000 description 1
- NPOJFIBHGTYPCE-UHFFFAOYSA-N C=COCCONC(c(ccc1c2cn[nH]1)c2Nc(c(F)c1)ccc1Br)=O Chemical compound C=COCCONC(c(ccc1c2cn[nH]1)c2Nc(c(F)c1)ccc1Br)=O NPOJFIBHGTYPCE-UHFFFAOYSA-N 0.000 description 1
- WMKYKJNEVDLVBE-UHFFFAOYSA-N CC(C)(C)OC([n]1ncc2c1ccc(N)c2Nc(ccc(I)c1)c1F)=O Chemical compound CC(C)(C)OC([n]1ncc2c1ccc(N)c2Nc(ccc(I)c1)c1F)=O WMKYKJNEVDLVBE-UHFFFAOYSA-N 0.000 description 1
- JNIFIXFEMBMCGU-UHFFFAOYSA-N CC(C)(C)OC(c(c(Br)c1C=O)ccc1SCc1ccccc1)=O Chemical compound CC(C)(C)OC(c(c(Br)c1C=O)ccc1SCc1ccccc1)=O JNIFIXFEMBMCGU-UHFFFAOYSA-N 0.000 description 1
- JSMGPZWRXKAVJY-GFCCVEGCSA-N CC1(C)O[C@@H](CONC(c(ccc2c3cn[s]2)c3Nc(ccc(I)c2)c2F)=O)CO1 Chemical compound CC1(C)O[C@@H](CONC(c(ccc2c3cn[s]2)c3Nc(ccc(I)c2)c2F)=O)CO1 JSMGPZWRXKAVJY-GFCCVEGCSA-N 0.000 description 1
- HHCPUPVQSIDAJR-UHFFFAOYSA-N COC(c(c(F)c(c(OC)c1)[N+]([O-])=O)c1F)OC Chemical compound COC(c(c(F)c(c(OC)c1)[N+]([O-])=O)c1F)OC HHCPUPVQSIDAJR-UHFFFAOYSA-N 0.000 description 1
- YKYZGKLTCYRIBR-UHFFFAOYSA-N Cc(c(N)ccc1C(OC)=O)c1Cl Chemical compound Cc(c(N)ccc1C(OC)=O)c1Cl YKYZGKLTCYRIBR-UHFFFAOYSA-N 0.000 description 1
- WNYBDXDNWMFXPU-UHFFFAOYSA-N Cc(cc1)ccc1S([n]1ncc2c1ccc(C(OC)=O)c2Nc(c(F)c1)ccc1I)=O Chemical compound Cc(cc1)ccc1S([n]1ncc2c1ccc(C(OC)=O)c2Nc(c(F)c1)ccc1I)=O WNYBDXDNWMFXPU-UHFFFAOYSA-N 0.000 description 1
- DDHMFHZVMCWHNC-UHFFFAOYSA-N O=C(c(ccc1c2cn[nH]1)c2Nc(c(F)c1)ccc1I)NOCC1CC1 Chemical compound O=C(c(ccc1c2cn[nH]1)c2Nc(c(F)c1)ccc1I)NOCC1CC1 DDHMFHZVMCWHNC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7742608P | 2008-07-01 | 2008-07-01 | |
| US61/077,426 | 2008-07-01 | ||
| PCT/US2009/049453 WO2010003025A1 (en) | 2008-07-01 | 2009-07-01 | Bicyclic heterocycles as mek kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102137847A CN102137847A (zh) | 2011-07-27 |
| CN102137847B true CN102137847B (zh) | 2015-06-10 |
Family
ID=41038842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980133788.0A Expired - Fee Related CN102137847B (zh) | 2008-07-01 | 2009-07-01 | 作为mek激酶抑制剂的二环杂环 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8841462B2 (https=) |
| EP (1) | EP2310373A1 (https=) |
| JP (1) | JP5544358B2 (https=) |
| KR (1) | KR20110029161A (https=) |
| CN (1) | CN102137847B (https=) |
| AU (1) | AU2009266956B2 (https=) |
| BR (1) | BRPI0910175A2 (https=) |
| CA (1) | CA2727250A1 (https=) |
| CL (1) | CL2010001641A1 (https=) |
| IL (1) | IL209931A0 (https=) |
| MX (1) | MX2010014559A (https=) |
| PE (1) | PE20110570A1 (https=) |
| RU (1) | RU2509078C2 (https=) |
| WO (1) | WO2010003025A1 (https=) |
| ZA (1) | ZA201008963B (https=) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2010317167B2 (en) | 2009-11-04 | 2012-11-29 | Novartis Ag | Heterocyclic sulfonamide derivatives useful as MEK inhibitors |
| CN102020651B (zh) | 2010-11-02 | 2012-07-18 | 北京赛林泰医药技术有限公司 | 6-芳基氨基吡啶酮甲酰胺mek抑制剂 |
| EA201391820A1 (ru) * | 2011-06-09 | 2014-12-30 | Новартис Аг | Гетероциклические сульфонамидные производные |
| US20150265679A1 (en) | 2012-11-02 | 2015-09-24 | The United States Of America, As Represented By Secretary, Department Of Health And Human Services | Method of reducing adverse effects in a cancer patient undregoing treatment with a mek inhibitor |
| US9227969B2 (en) | 2013-08-14 | 2016-01-05 | Novartis Ag | Compounds and compositions as inhibitors of MEK |
| US9532987B2 (en) | 2013-09-05 | 2017-01-03 | Genentech, Inc. | Use of a combination of a MEK inhibitor and an ERK inhibitor for treatment of hyperproliferative diseases |
| NO2714752T3 (https=) | 2014-05-08 | 2018-04-21 | ||
| US20170114323A1 (en) | 2014-06-19 | 2017-04-27 | Whitehead Institute For Biomedical Research | Uses of kinase inhibitors for inducing and maintaining pluripotency |
| CN104119332B (zh) * | 2014-07-08 | 2019-03-29 | 上海科州药物研发有限公司 | 作为蛋白激酶抑制剂的苯并杂环化合物及其制备方法和用途 |
| CN104860869B (zh) * | 2015-04-03 | 2017-11-03 | 北京大学 | 具有mek激酶抑制功能的化合物及其制备方法与应用 |
| HUE050317T2 (hu) | 2015-05-20 | 2020-11-30 | Amgen Inc | APJ receptor triazol agonistái |
| WO2017033113A1 (en) | 2015-08-21 | 2017-03-02 | Acerta Pharma B.V. | Therapeutic combinations of a mek inhibitor and a btk inhibitor |
| GB201516504D0 (en) | 2015-09-17 | 2015-11-04 | Astrazeneca Ab | Imadazo(4,5-c)quinolin-2-one Compounds and their use in treating cancer |
| KR20180134347A (ko) | 2016-04-15 | 2018-12-18 | 제넨테크, 인크. | 암의 진단 및 치료 방법 |
| US9988369B2 (en) | 2016-05-03 | 2018-06-05 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the APJ receptor |
| ES2896943T3 (es) | 2016-10-28 | 2022-02-28 | Chia Tai Tianqing Pharmaceutical Group Co Ltd | Compuesto de amino pirazolopirimidina usado como inhibidor de receptores con actividad tirosina quinasa de factores neurotróficos |
| US10736883B2 (en) | 2016-11-16 | 2020-08-11 | Amgen Inc. | Triazole furan compounds as agonists of the APJ receptor |
| EP3541803B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole pyridyl compounds as agonists of the apj receptor |
| WO2018093579A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Triazole phenyl compounds as agonists of the apj receptor |
| US11046680B1 (en) | 2016-11-16 | 2021-06-29 | Amgen Inc. | Heteroaryl-substituted triazoles as APJ receptor agonists |
| WO2018093576A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Alkyl substituted triazole compounds as agonists of the apj receptor |
| WO2018093577A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Cycloalkyl substituted triazole compounds as agonists of the apj receptor |
| KR102811888B1 (ko) | 2017-09-08 | 2025-05-27 | 에프. 호프만-라 로슈 아게 | 암의 진단 및 치료 방법 |
| MA50509A (fr) | 2017-11-03 | 2021-06-02 | Amgen Inc | Agonistes de triazole fusionnés du récepteur apj |
| EP3752200A1 (en) | 2018-02-13 | 2020-12-23 | Vib Vzw | Targeting minimal residual disease in cancer with rxr antagonists |
| US11807624B2 (en) | 2018-05-01 | 2023-11-07 | Amgen Inc. | Substituted pyrimidinones as agonists of the APJ receptor |
| JP2023504623A (ja) * | 2019-12-04 | 2023-02-06 | アーカス バイオサイエンシーズ，インコーポレーテッド | Ｈｉｆ－２アルファの阻害剤 |
| CA3197685A1 (en) | 2020-10-29 | 2022-05-05 | Shenzhen Chipscreen Biosciences Co., Ltd. | Biphenyl compound as immunomodulator, preparation method therefor and application thereof |
| US12371667B2 (en) | 2021-05-13 | 2025-07-29 | Washington University | Enhanced methods for inducing and maintaining naive human pluripotent stem cells |
| US12280055B2 (en) | 2021-05-27 | 2025-04-22 | Mirati Therapeutics, Inc. | Combination therapies |
| CN113336786B (zh) * | 2021-05-31 | 2022-10-18 | 南京工业大学 | 一种非对映选择性的多取代环烷基化合物及其制备方法 |
| US20260048075A1 (en) | 2022-08-10 | 2026-02-19 | Vib Vzw | Inhibition of TCF4/ITF2 in the Treatment of Cancer |
| WO2026019990A1 (en) | 2024-07-18 | 2026-01-22 | Genentech, Inc. | Methods of treating cancer with anti-ccr8/anti-cd3 bispecific antibodies |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2017853C3 (de) | 1970-04-14 | 1975-12-11 | Standard Elektrik Lorenz Ag, 7000 Stuttgart | Steuerverfahren zur Sicherung der Informationsverarbeitung und -Übertragung |
| CA920592A (en) * | 1970-05-28 | 1973-02-06 | Denzel Theodor | Amino derivatives of pyrazolo-pyridine carboxylic acids and esters |
| US3736326A (en) * | 1971-03-29 | 1973-05-29 | Squibb & Sons Inc | Isoxazolopyridine carboxylic acids and esters |
| US3780047A (en) * | 1972-07-05 | 1973-12-18 | Squibb & Sons Inc | Derivatives of pyrazolo(3',4'-2,3)pyrido(4,5-e)b-benzo-1,5-diazepines |
| US4012373A (en) * | 1972-09-22 | 1977-03-15 | E. R. Squibb & Sons, Inc. | Pyrazolo[3',4'-2,3]pyrido[4,5-e]b-benzo-1,5-diazepinones |
| GB8404586D0 (en) * | 1984-02-22 | 1984-03-28 | Beecham Group Plc | Compounds |
| JP2002020386A (ja) * | 2000-07-07 | 2002-01-23 | Ono Pharmaceut Co Ltd | ピラゾロピリジン誘導体 |
| JP3811775B2 (ja) | 2000-07-19 | 2006-08-23 | ワーナー−ランバート カンパニー リミティド ライアビリティー カンパニー | ４−ヨードフェニルアミノベンズヒドロキサム酸の酸素化エステル |
| US20050009876A1 (en) * | 2000-07-31 | 2005-01-13 | Bhagwat Shripad S. | Indazole compounds, compositions thereof and methods of treatment therewith |
| KR100984595B1 (ko) | 2002-03-13 | 2010-09-30 | 어레이 바이오파마 인크. | Ｍｅｋ 억제제로서의 ｎ3 알킬화 벤즈이미다졸 유도체 |
| EP1482944A4 (en) | 2002-03-13 | 2006-04-19 | Array Biopharma Inc | NZ ALKYL BENZIMIDAZOLE DERIVATIVES AS MEK INHIBITORS |
| GB0220581D0 (en) | 2002-09-04 | 2002-10-09 | Novartis Ag | Organic Compound |
| CL2003002287A1 (es) * | 2002-11-25 | 2005-01-14 | Wyeth Corp | COMPUESTOS DERIVADOS DE TIENO[3,2-b]-PIRIDINA-6-CARBONITRILOS Y TIENEO[2,3-b]-PIRIDINA-5-CARBONITRILOS, COMPOSICION FARMACEUTICA, PROCEDIMIENTO DE PREPARACION Y COMPUESTOS INTERMEDIARIOS, Y SU USO EN EL TRATAMIENTO DEL CANCER, APOPLEJIA, OSTEOPOROSIS |
| GB0316237D0 (en) | 2003-07-11 | 2003-08-13 | Astrazeneca Ab | Therapeutic agents |
| GB0316232D0 (en) | 2003-07-11 | 2003-08-13 | Astrazeneca Ab | Therapeutic agents |
| US20050049276A1 (en) | 2003-07-23 | 2005-03-03 | Warner-Lambert Company, Llc | Imidazopyridines and triazolopyridines |
| ATE506953T1 (de) | 2003-08-07 | 2011-05-15 | Rigel Pharmaceuticals Inc | 2,4-pyrimidindiamin-verbindungen und verwendungen als antiproliferative mittel |
| US7538120B2 (en) | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| US7144907B2 (en) * | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| CN1905873A (zh) | 2003-11-19 | 2007-01-31 | 阵列生物制药公司 | Mek的杂环抑制剂及其使用方法 |
| ATE386715T1 (de) | 2003-11-25 | 2008-03-15 | Lilly Co Eli | Modulatoren des peroxisomproliferatoraktivierten rezeptors |
| AU2004299438A1 (en) | 2003-12-19 | 2005-06-30 | Biovitrum Ab | Novel benzofuran derivatives, which can be used in prophylaxis or treatment of 5-HT6 receptor-related disorder |
| JP4805166B2 (ja) | 2003-12-22 | 2011-11-02 | バジリア ファルマスーチカ アーゲー | アロイルフランおよびアロイルチオフェン |
| WO2005063296A2 (en) | 2003-12-23 | 2005-07-14 | Pfizer Products Inc. | Therapeutic combination for cognition enhancement and psychotic disorders |
| WO2007027855A2 (en) | 2005-09-01 | 2007-03-08 | Array Biopharma Inc. | Raf inhibitor compounds and methods of use thereof |
| SI1934174T1 (sl) * | 2005-10-07 | 2011-08-31 | Exelixis Inc | Inhibitorji MEK in postopki za njihovo uporabo |
| WO2008028141A2 (en) | 2006-08-31 | 2008-03-06 | Array Biopharma Inc. | Raf inhibitor compounds and methods of use thereof |
-
2009
- 2009-07-01 US US12/999,003 patent/US8841462B2/en not_active Expired - Fee Related
- 2009-07-01 JP JP2011516860A patent/JP5544358B2/ja not_active Expired - Fee Related
- 2009-07-01 MX MX2010014559A patent/MX2010014559A/es active IP Right Grant
- 2009-07-01 CN CN200980133788.0A patent/CN102137847B/zh not_active Expired - Fee Related
- 2009-07-01 WO PCT/US2009/049453 patent/WO2010003025A1/en not_active Ceased
- 2009-07-01 PE PE2010001198A patent/PE20110570A1/es not_active Application Discontinuation
- 2009-07-01 KR KR1020117002481A patent/KR20110029161A/ko not_active Ceased
- 2009-07-01 RU RU2011103454/04A patent/RU2509078C2/ru not_active IP Right Cessation
- 2009-07-01 BR BRPI0910175A patent/BRPI0910175A2/pt not_active IP Right Cessation
- 2009-07-01 AU AU2009266956A patent/AU2009266956B2/en not_active Ceased
- 2009-07-01 EP EP09774475A patent/EP2310373A1/en not_active Withdrawn
- 2009-07-01 CA CA2727250A patent/CA2727250A1/en not_active Abandoned
-
2010
- 2010-12-12 IL IL209931A patent/IL209931A0/en unknown
- 2010-12-13 ZA ZA2010/08963A patent/ZA201008963B/en unknown
- 2010-12-30 CL CL2010001641A patent/CL2010001641A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP5544358B2 (ja) | 2014-07-09 |
| MX2010014559A (es) | 2011-03-04 |
| AU2009266956A1 (en) | 2010-01-07 |
| RU2011103454A (ru) | 2012-08-10 |
| CL2010001641A1 (es) | 2011-07-15 |
| KR20110029161A (ko) | 2011-03-22 |
| AU2009266956B2 (en) | 2014-03-20 |
| US20110190257A1 (en) | 2011-08-04 |
| JP2011526926A (ja) | 2011-10-20 |
| AU2009266956A2 (en) | 2011-03-10 |
| CA2727250A1 (en) | 2010-01-07 |
| EP2310373A1 (en) | 2011-04-20 |
| CN102137847A (zh) | 2011-07-27 |
| BRPI0910175A2 (pt) | 2017-03-21 |
| ZA201008963B (en) | 2012-03-28 |
| US8841462B2 (en) | 2014-09-23 |
| IL209931A0 (en) | 2011-02-28 |
| WO2010003025A1 (en) | 2010-01-07 |
| PE20110570A1 (es) | 2011-08-26 |
| RU2509078C2 (ru) | 2014-03-10 |
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