AU2009289196A1 - Pyrido [5, 4-d] pyrimidines as cell proliferation inhibitors - Google Patents
Pyrido [5, 4-d] pyrimidines as cell proliferation inhibitors Download PDFInfo
- Publication number
- AU2009289196A1 AU2009289196A1 AU2009289196A AU2009289196A AU2009289196A1 AU 2009289196 A1 AU2009289196 A1 AU 2009289196A1 AU 2009289196 A AU2009289196 A AU 2009289196A AU 2009289196 A AU2009289196 A AU 2009289196A AU 2009289196 A1 AU2009289196 A1 AU 2009289196A1
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- Prior art keywords
- alkyl
- pct
- hydrogen
- denotes
- membered
- 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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- 230000004663 cell proliferation Effects 0.000 title description 7
- 239000003112 inhibitor Substances 0.000 title description 6
- PAQYIEZTLSDLQO-UHFFFAOYSA-N pyrido[3,4-d]pyrimidine Chemical class N1=CN=C2C=NC=CC2=C1 PAQYIEZTLSDLQO-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 186
- -1 tert.-butoxy Chemical group 0.000 claims description 157
- 125000000217 alkyl group Chemical group 0.000 claims description 114
- 125000001424 substituent group Chemical group 0.000 claims description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 59
- 125000001072 heteroaryl group Chemical group 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 125000001188 haloalkyl group Chemical group 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 206010028980 Neoplasm Diseases 0.000 claims description 25
- 239000013543 active substance Substances 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 108010011222 cyclo(Arg-Pro) Proteins 0.000 claims description 19
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 12
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical group N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
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- XRMDCWJNPDVAFI-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[N+]1=O XRMDCWJNPDVAFI-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-OUBTZVSYSA-N Ammonia-15N Chemical compound [15NH3] QGZKDVFQNNGYKY-OUBTZVSYSA-N 0.000 claims 1
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Classifications
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A—HUMAN NECESSITIES
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
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- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| PCT/EP2009/061656 WO2010026262A1 (en) | 2008-09-08 | 2009-09-08 | Pyrido [5, 4-d] pyrimidines as cell proliferation inhibitors |
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| CL2008001943A1 (es) | 2007-07-02 | 2009-09-11 | Boehringer Ingelheim Int | Compuestos derivados de fenil-triazol, inhibidores de enzimas de señales especificas que participan del control de la proliferacion celular; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar cancer, infecciones, enfermedades inflamatorias y autoinmunes. |
| AR073501A1 (es) | 2008-09-08 | 2010-11-10 | Boehringer Ingelheim Int | Derivados de pirimido[5,4-d]pirimidina inhibidores de la tirosinoquinasa |
| US8778929B2 (en) | 2008-09-29 | 2014-07-15 | Boehringer Ingelheim International Gmbh | Substituted heteroaryl inhibitors of B-RAF |
| JP5603883B2 (ja) * | 2009-02-17 | 2014-10-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｂ−Ｒａｆキナーゼを阻害するためのピリミドピリミジン誘導体 |
| PE20121118A1 (es) | 2009-05-12 | 2012-09-05 | Romark Lab Lc | Compuestos de haloalquil heteroaril benzamida |
| US9023877B2 (en) | 2009-06-26 | 2015-05-05 | Romark Laboratories L.C. | Compounds and methods for treating influenza |
| JP5871896B2 (ja) | 2010-03-26 | 2016-03-01 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｂ−ｒａｆキナーゼインヒビター |
| WO2011117382A1 (en) | 2010-03-26 | 2011-09-29 | Boehringer Ingelheim International Gmbh | Pyridyltriazoles |
| US8710055B2 (en) | 2010-12-21 | 2014-04-29 | Boehringer Ingelheim International Gmbh | Triazolylphenyl sulfonamides as serine/threonine kinase inhibitors |
| ES2882807T3 (es) | 2011-09-16 | 2021-12-02 | Novartis Ag | Heterociclil carboxamidas N-sustituidas |
| US9462809B2 (en) | 2012-03-13 | 2016-10-11 | Basf Se | Fungicidal pyrimidine compounds |
| WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
| CA2923101A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
| EP3609882B1 (en) | 2017-03-17 | 2022-07-13 | Cardio Therapeutics Pty Ltd | Heterocyclic inhibitors of pcsk9 |
| BR112023021111A2 (pt) | 2021-04-13 | 2023-12-19 | Nuvalent Inc | Composto, composição farmacêutica, método de tratamento de câncer, método para inibir seletivamente her2, método de regulação de um nível de her2, método para aumentar um nível de her2, método de diminuição da fosforilação de her2 |
| CN117177975A (zh) * | 2021-04-19 | 2023-12-05 | 蒙特利尔大学 | 嘧啶并[5,4,d]嘧啶化合物、包含其的组合物及其用途 |
| JP2024514227A (ja) * | 2021-04-19 | 2024-03-28 | ユニヴェルシテ ド モントリオール | ピリド［３，２－ｄ］ピリミジン化合物、該化合物を含む組成物、及びそれらの使用方法 |
| CA3268209A1 (en) * | 2022-10-13 | 2024-04-18 | Universite De Montreal | Thiazolo[5,4-D]pyrimidine compounds, compositions containing them and their uses |
| AU2023410324A1 (en) | 2022-12-22 | 2025-05-15 | Boehringer Ingelheim International Gmbh | Crystalline forms of a her2 inhibitor |
| TW202521538A (zh) | 2023-07-28 | 2025-06-01 | 德商百靈佳殷格翰國際股份有限公司 | 製備her2抑制劑之方法 |
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| TW414798B (en) * | 1994-09-07 | 2000-12-11 | Thomae Gmbh Dr K | Pyrimido (5,4-d) pyrimidines, medicaments comprising these compounds, their use and processes for their preparation |
| ATE247469T1 (de) | 1995-06-07 | 2003-09-15 | Pfizer | Heterocyclische kondensierte pyrimidin-derivate |
| DE19608653A1 (de) | 1996-03-06 | 1997-09-11 | Thomae Gmbh Dr K | Pyrimido[5,4-d]pyrimidine, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
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| AR007857A1 (es) | 1996-07-13 | 1999-11-24 | Glaxo Group Ltd | Compuestos heterociclicos fusionados como inhibidores de proteina tirosina quinasa, sus metodos de preparacion, intermediarios uso en medicina ycomposiciones farmaceuticas que los contienen. |
| EP0837063A1 (en) * | 1996-10-17 | 1998-04-22 | Pfizer Inc. | 4-Aminoquinazoline derivatives |
| UA71945C2 (en) | 1999-01-27 | 2005-01-17 | Pfizer Prod Inc | Substituted bicyclic derivatives being used as anticancer agents |
| JP3270834B2 (ja) * | 1999-01-27 | 2002-04-02 | ファイザー・プロダクツ・インク | 抗がん剤として有用なヘテロ芳香族二環式誘導体 |
| DE19911510A1 (de) * | 1999-03-15 | 2000-09-21 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| DE60306193T2 (de) | 2002-11-27 | 2006-10-12 | Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield | 1,2,3-triazolamid-derivate als cytokininhibitoren |
| CN102060806A (zh) | 2003-09-11 | 2011-05-18 | iTherX药品公司 | 细胞因子抑制剂 |
| EP1692116B1 (en) | 2003-12-03 | 2011-03-09 | Boehringer Ingelheim Pharmaceuticals Inc. | 1,2,3-triazole amide derivatives as inhibitors of cytokine production |
| DE102004002557A1 (de) * | 2004-01-17 | 2005-08-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verwendung von substituierten Pyrimido(5,4-d)pyrimidinen zur Behandlung von Atemwegserkrankungen |
| CA2557856C (en) | 2004-03-09 | 2010-06-29 | Boehringer Ingelheim Pharmaceuticals, Inc. | 3-'4-heterocyclyl-1,2,3,-triazol-1-yl!-n-aryl-benzamides as inhibitors of the cytokines production for the treatment of chronic inflammatory diseases |
| US7485657B2 (en) | 2004-05-12 | 2009-02-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
| US7531560B2 (en) | 2004-11-10 | 2009-05-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
| JP2007076376A (ja) | 2005-09-09 | 2007-03-29 | Yanmar Co Ltd | トラクタ |
| WO2007056016A2 (en) | 2005-11-02 | 2007-05-18 | Kemia, Inc. | Bisamide cytokine inhibitors |
| WO2007075896A2 (en) | 2005-12-22 | 2007-07-05 | Kemia, Inc. | Heterocyclic cytokine inhibitors |
| US7858804B2 (en) | 2006-04-18 | 2010-12-28 | Boehringer Ingelheim International Gmbh | Process for making cytokine inhibiting compounds containing 4- and 5-imidazolyl rings and the intermediates thereof |
| BRPI0711628A2 (pt) * | 2006-05-15 | 2011-12-06 | Irm Llc | composto, composição farmacêutica, uso e processo para preparação do composto |
| UA95298C2 (ru) | 2006-07-07 | 2011-07-25 | Бьёрингер Ингельхайм Интернациональ Гмбх | Фенилзамещенные гетероарильные производные и их применение в качестве противоопухолевых средств |
| PE20080906A1 (es) | 2006-08-17 | 2008-07-05 | Kemia Inc | Derivados heteroarilo como inhibidores de citocina |
| WO2008089034A2 (en) | 2007-01-11 | 2008-07-24 | Kemia, Inc. | Cytokine inhibitors |
| MX2009011062A (es) | 2007-04-13 | 2009-10-29 | Schering Corp | Derivados de pirimidindiona y sus metodos de uso. |
| CA2692379A1 (en) | 2007-07-02 | 2009-01-08 | Boehringer Ingelheim International Gmbh | Antiproliferative compounds based on 5-membered heterocycles |
| CL2008001943A1 (es) | 2007-07-02 | 2009-09-11 | Boehringer Ingelheim Int | Compuestos derivados de fenil-triazol, inhibidores de enzimas de señales especificas que participan del control de la proliferacion celular; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar cancer, infecciones, enfermedades inflamatorias y autoinmunes. |
| BRPI0814423B1 (pt) | 2007-07-17 | 2022-04-19 | Plexxikon, Inc | Compostos que modulam quinase e composição farmacêutica compreendendo os mesmos |
| AR073501A1 (es) | 2008-09-08 | 2010-11-10 | Boehringer Ingelheim Int | Derivados de pirimido[5,4-d]pirimidina inhibidores de la tirosinoquinasa |
| US8778929B2 (en) | 2008-09-29 | 2014-07-15 | Boehringer Ingelheim International Gmbh | Substituted heteroaryl inhibitors of B-RAF |
| WO2010042337A1 (en) | 2008-10-07 | 2010-04-15 | Merck Sharp & Dohme Corp. | Novel 6-azaindole aminopyrimidine derivatives having nik inhibitory activity |
| JP5603883B2 (ja) | 2009-02-17 | 2014-10-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｂ−Ｒａｆキナーゼを阻害するためのピリミドピリミジン誘導体 |
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| US8710055B2 (en) | 2010-12-21 | 2014-04-29 | Boehringer Ingelheim International Gmbh | Triazolylphenyl sulfonamides as serine/threonine kinase inhibitors |
| US20130023531A1 (en) | 2011-01-27 | 2013-01-24 | Boehringer Ingelheim International Gmbh | Pyrimido[5,4-d]pyrimidylamino phenyl sulfonamides as serine/threonine kinase inhibitors |
| US8889684B2 (en) | 2011-02-02 | 2014-11-18 | Boehringer Ingelheim International Gmbh | Azaindolylphenyl sulfonamides as serine/threonine kinase inhibitors |
-
2009
- 2009-09-07 AR ARP090103435A patent/AR073501A1/es unknown
- 2009-09-07 TW TW098130118A patent/TW201014860A/zh unknown
- 2009-09-08 CN CN2009801439757A patent/CN102203098A/zh active Pending
- 2009-09-08 WO PCT/EP2009/061656 patent/WO2010026262A1/en not_active Ceased
- 2009-09-08 EP EP09782789.3A patent/EP2350083B1/en active Active
- 2009-09-08 RU RU2011113402/04A patent/RU2011113402A/ru not_active Application Discontinuation
- 2009-09-08 JP JP2011525573A patent/JP5576379B2/ja active Active
- 2009-09-08 CA CA2736306A patent/CA2736306A1/en not_active Abandoned
- 2009-09-08 MX MX2011002431A patent/MX2011002431A/es unknown
- 2009-09-08 NZ NZ591493A patent/NZ591493A/en not_active IP Right Cessation
- 2009-09-08 AU AU2009289196A patent/AU2009289196A1/en not_active Abandoned
- 2009-09-08 KR KR1020117008042A patent/KR20110063528A/ko not_active Withdrawn
- 2009-09-08 US US13/062,058 patent/US8653087B2/en active Active
-
2011
- 2011-02-09 IL IL211136A patent/IL211136A0/en unknown
- 2011-02-10 ZA ZA2011/01090A patent/ZA201101090B/en unknown
- 2011-03-07 CL CL2011000489A patent/CL2011000489A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA201101090B (en) | 2012-10-31 |
| AR073501A1 (es) | 2010-11-10 |
| US8653087B2 (en) | 2014-02-18 |
| WO2010026262A1 (en) | 2010-03-11 |
| IL211136A0 (en) | 2011-04-28 |
| CA2736306A1 (en) | 2010-03-11 |
| EP2350083B1 (en) | 2017-05-17 |
| NZ591493A (en) | 2012-07-27 |
| TW201014860A (en) | 2010-04-16 |
| EP2350083A1 (en) | 2011-08-03 |
| JP2012502010A (ja) | 2012-01-26 |
| JP5576379B2 (ja) | 2014-08-20 |
| CL2011000489A1 (es) | 2011-07-15 |
| KR20110063528A (ko) | 2011-06-10 |
| RU2011113402A (ru) | 2012-10-20 |
| US20120094975A1 (en) | 2012-04-19 |
| MX2011002431A (es) | 2011-04-05 |
| CN102203098A (zh) | 2011-09-28 |
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