AU2010319964A1 - Kinase inhibitors - Google Patents
Kinase inhibitorsInfo
- Publication number
- AU2010319964A1 AU2010319964A1 AU2010319964A AU2010319964A AU2010319964A1 AU 2010319964 A1 AU2010319964 A1 AU 2010319964A1 AU 2010319964 A AU2010319964 A AU 2010319964A AU 2010319964 A AU2010319964 A AU 2010319964A AU 2010319964 A1 AU2010319964 A1 AU 2010319964A1
- Authority
- AU
- Australia
- Prior art keywords
- substituted
- unsubstituted
- heteroaryl
- alkyl
- heterocycloalkyl
- 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.)
- Abandoned
Links
- 229940043355 kinase inhibitor Drugs 0.000 title claims abstract description 191
- 239000003757 phosphotransferase inhibitor Substances 0.000 title claims abstract description 189
- 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 134
- 102000020233 phosphotransferase Human genes 0.000 claims abstract description 134
- 238000000034 method Methods 0.000 claims abstract description 90
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 234
- 125000000217 alkyl group Chemical group 0.000 claims description 179
- 125000003118 aryl group Chemical group 0.000 claims description 162
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 160
- 150000001875 compounds Chemical class 0.000 claims description 152
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 144
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 138
- 229910052739 hydrogen Inorganic materials 0.000 claims description 122
- 239000001257 hydrogen Substances 0.000 claims description 114
- 229910052736 halogen Inorganic materials 0.000 claims description 94
- 150000002367 halogens Chemical class 0.000 claims description 92
- -1 7H-pyrrolo[2,3-d]pyrimidinyl Chemical group 0.000 claims description 91
- 150000002431 hydrogen Chemical class 0.000 claims description 87
- 230000002441 reversible effect Effects 0.000 claims description 87
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 85
- 108060006633 protein kinase Proteins 0.000 claims description 84
- 102000001253 Protein Kinase Human genes 0.000 claims description 83
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 83
- 230000000694 effects Effects 0.000 claims description 52
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 47
- 125000002947 alkylene group Chemical group 0.000 claims description 40
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 39
- 125000005549 heteroarylene group Chemical group 0.000 claims description 39
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 36
- 125000000732 arylene group Chemical group 0.000 claims description 35
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 35
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 33
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 230000005764 inhibitory process Effects 0.000 claims description 20
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- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
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- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
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- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
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- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
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- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 2
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- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000005306 thianaphthenyl group Chemical group 0.000 claims description 2
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 46
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- 230000002829 reductive effect Effects 0.000 description 30
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- A—HUMAN NECESSITIES
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- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
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| US26169609P | 2009-11-16 | 2009-11-16 | |
| US61/261,696 | 2009-11-16 | ||
| US33027110P | 2010-04-30 | 2010-04-30 | |
| US61/330,271 | 2010-04-30 | ||
| PCT/US2010/056890 WO2011060440A2 (en) | 2009-11-16 | 2010-11-16 | Kinase inhibitors |
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| AU2010319964A1 true AU2010319964A1 (en) | 2012-06-07 |
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| EP (1) | EP2558099A4 (enExample) |
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| MX (1) | MX2012005678A (enExample) |
| WO (1) | WO2011060440A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US9376438B2 (en) | 2011-05-17 | 2016-06-28 | Principia Biopharma, Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
| ES2770550T3 (es) * | 2011-05-17 | 2020-07-02 | Univ California | Inhibidores de quinasa |
| PL2710005T3 (pl) | 2011-05-17 | 2017-07-31 | Principia Biopharma Inc. | Inhibitory kinazy tyrozynowej |
| AU2013277582B2 (en) | 2012-06-18 | 2017-11-30 | Principia Biopharma Inc. | Reversible covalent pyrrolo- or pyrazolopyrimidines useful for the treatment cancer and autoimmune diseases |
| WO2014036016A1 (en) | 2012-08-31 | 2014-03-06 | Principia Biopharma Inc. | Benzimidazole derivatives as itk inhibitors |
| SMT201900344T1 (it) | 2012-09-10 | 2019-07-11 | Principia Biopharma Inc | Composti di pirazolopirimidina come inibitori di chinasi |
| WO2014093230A2 (en) | 2012-12-10 | 2014-06-19 | Merck Patent Gmbh | Compositions and methods for the production of pyrimidine and pyridine compounds with btk inhibitory activity |
| US8957080B2 (en) | 2013-04-09 | 2015-02-17 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| KR20220027271A (ko) | 2014-02-21 | 2022-03-07 | 프린시피아 바이오파마, 인코퍼레이티드 | Btk 억제제의 염 및 고체 형태 |
| JP6409116B2 (ja) | 2014-07-07 | 2018-10-17 | チャンスー ヘンルイ メディシン カンパニー,リミテッド | プロテインキナーゼ阻害剤としてのアミノピリダジノン化合物 |
| CA2970723C (en) | 2014-12-18 | 2023-09-05 | Principia Biopharma Inc. | Treatment of pemphigus |
| MA42242A (fr) | 2015-06-24 | 2018-05-02 | Principia Biopharma Inc | Inhibiteurs de la tyrosine kinase |
| CN106939002B (zh) * | 2016-01-05 | 2019-09-24 | 江苏恒瑞医药股份有限公司 | 一种btk激酶抑制剂的结晶形式及其制备方法 |
| CN107406453B (zh) * | 2016-01-05 | 2018-12-28 | 江苏恒瑞医药股份有限公司 | 一种btk激酶抑制剂的结晶形式及其制备方法 |
| WO2018005849A1 (en) | 2016-06-29 | 2018-01-04 | Principia Biopharma Inc. | Modified release formulations of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
| JOP20180094A1 (ar) | 2017-10-18 | 2019-04-18 | Hk Inno N Corp | مركب حلقي غير متجانس كمثبط بروتين كيناز |
| KR102195348B1 (ko) | 2018-11-15 | 2020-12-24 | 에이치케이이노엔 주식회사 | 단백질 키나제 억제제로서의 신규 화합물 및 이를 포함하는 약제학적 조성물 |
| TWI877239B (zh) | 2019-10-14 | 2025-03-21 | 美商普林斯匹亞生物製藥公司 | 藉由投予(R)-2-[3-[4-胺基-3-(2-氟-4-苯氧基-苯基)吡唑并[3,4-d]嘧啶-1-基]哌啶-1-羰基]-4-甲基-4-[4-(氧呾-3-基)哌-1-基]戊-2-烯腈來治療免疫血小板減少症之方法 |
| BR112022014149A2 (pt) | 2020-01-22 | 2022-09-27 | Principia Biopharma Inc | Formas cristalinas de 2-[3-[4-amino-3-(2-fluoro-4-fenóxi-fenil)-1h-pirazolo[3,4-d]pirimidina-1-il]piperidina-1-carbonil]-4-metil-4-[4-(oxetan-3-il)piperazin-1-il]pent-2-enenitrila |
| CN111205232B (zh) * | 2020-02-26 | 2022-07-01 | 浙江天宇药业股份有限公司 | 一种替格瑞洛中间体的合成方法 |
| WO2022251597A1 (en) | 2021-05-28 | 2022-12-01 | Verge Analytics, Inc. | Methods of treating neurological disorders with modulators of ribosomal protein s6 kinase alpha-1 (rsk1) and ribosomal protein s6 kinase alpha-3 (rsk2) |
| CN116410228B (zh) * | 2023-05-04 | 2025-10-31 | 南京颐媛生物医学研究院有限公司 | 一种抗冠状病毒核苷类化合物的制备方法及其应用 |
| CN116284135B (zh) * | 2023-05-04 | 2025-03-21 | 南京颐媛生物医学研究院有限公司 | 抗冠状病毒核苷类化合物的制备方法及其应用 |
| CN116332996B (zh) * | 2023-05-04 | 2025-04-01 | 南京颐媛生物医学研究院有限公司 | L-呋喃核糖型抗冠状病毒化合物及其制备方法和应用 |
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| US4444770A (en) * | 1980-05-29 | 1984-04-24 | Bayer Aktiengesellschaft | New imidazoazole-alkenoic acid amide compounds, intermediate products for their production, their production, and their medicinal use |
| DE3216416A1 (de) * | 1982-05-03 | 1983-11-03 | Bayer Ag, 5090 Leverkusen | Heteroarylthiovinyl-verbindungen, ein verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| US4911920A (en) | 1986-07-30 | 1990-03-27 | Alcon Laboratories, Inc. | Sustained release, comfort formulation for glaucoma therapy |
| DE3502264A1 (de) * | 1985-01-24 | 1986-07-24 | Bayer Ag, 5090 Leverkusen | Imidazoalkensaeurederivate, ein verfahren zu ihrer herstellung und ihre verwendung fuer die herstellung pharmazeutischer wirkstoffe |
| FR2588189B1 (fr) | 1985-10-03 | 1988-12-02 | Merck Sharp & Dohme | Composition pharmaceutique de type a transition de phase liquide-gel |
| US5112833A (en) * | 1988-12-26 | 1992-05-12 | Zenyaku Kogyo Kabushiki Kaisha | 1-azaindolizine derivatives, synthetic intermediates thereof and antiallergic agents containing 1-azaindolizine derivatives |
| GB9004483D0 (en) * | 1990-02-28 | 1990-04-25 | Erba Carlo Spa | New aryl-and heteroarylethenylene derivatives and process for their preparation |
| ATE141502T1 (de) | 1991-01-15 | 1996-09-15 | Alcon Lab Inc | Verwendung von karrageenan in topischen ophthalmologischen zusammensetzungen |
| US5212162A (en) | 1991-03-27 | 1993-05-18 | Alcon Laboratories, Inc. | Use of combinations gelling polysaccharides and finely divided drug carrier substrates in topical ophthalmic compositions |
| JPH05301838A (ja) * | 1991-10-15 | 1993-11-16 | Mitsubishi Kasei Corp | スチレン誘導体 |
| US5792771A (en) * | 1992-11-13 | 1998-08-11 | Sugen, Inc. | Quinazoline compounds and compositions thereof for the treatment of disease |
| GB9226855D0 (en) * | 1992-12-23 | 1993-02-17 | Erba Carlo Spa | Vinylene-azaindole derivatives and process for their preparation |
| AU2096895A (en) * | 1994-03-07 | 1995-09-25 | Sugen, Incorporated | Receptor tyrosine kinase inhibitors for inhibiting cell proliferative disorders and compositions thereof |
| GB9406137D0 (en) * | 1994-03-28 | 1994-05-18 | Erba Carlo Spa | N-substituted beta-aryl- and betaheteroaryl-alpha-cyanoacrylamide derivatives and process for their preparation |
| GB9412719D0 (en) * | 1994-06-24 | 1994-08-17 | Erba Carlo Spa | Substituted azaindolylidene compounds and process for their preparation |
| US6331555B1 (en) * | 1995-06-01 | 2001-12-18 | University Of California | Treatment of platelet derived growth factor related disorders such as cancers |
| WO1999043673A1 (en) * | 1998-02-26 | 1999-09-02 | Zenyaku Kogyo Kabushiki Kaisha | 1-azaindolizine derivatives |
| DE602004009582T2 (de) * | 2003-08-01 | 2009-01-02 | Chugai Seiyaku K.K. | Cyanoamid-verbindungen als nützliche malonyl-coa decarboxylase-hemmer |
| US7807719B2 (en) * | 2004-09-14 | 2010-10-05 | Chaim Roifman | Compounds useful for modulating abnormal cell proliferation |
| WO2007043400A1 (ja) * | 2005-10-07 | 2007-04-19 | Kissei Pharmaceutical Co., Ltd. | 含窒素芳香族複素環化合物およびそれを含有する医薬組成物 |
| AU2007234455B2 (en) * | 2006-03-31 | 2012-10-04 | The Board Of Regents Of The University Of Texas System | Orally bioavailable caffeic acid related anticancer drugs |
| US7645748B2 (en) | 2006-04-03 | 2010-01-12 | Forbes Medi-Tech Inc. | Sterol/stanol phosphorylnitroderivatives and use thereof |
| US20100292229A1 (en) * | 2006-06-30 | 2010-11-18 | The Board Of Regents Of The University Of Texas System | Tryphostin-analogs for the treatment of cell proliferative diseases |
| CA2662677C (en) * | 2006-09-05 | 2016-05-31 | Emory University | Kinase inhibitors for preventing or treating pathogen infection and method of use thereof |
| US20120028981A1 (en) | 2008-11-05 | 2012-02-02 | Principia Biopharma Inc. | Kinase Knockdown Via Electrophilically Enhanced Inhibitors |
| US20100113520A1 (en) | 2008-11-05 | 2010-05-06 | Principia Biopharma, Inc. | Kinase knockdown via electrophilically enhanced inhibitors |
| US8426428B2 (en) | 2008-12-05 | 2013-04-23 | Principia Biopharma, Inc. | EGFR kinase knockdown via electrophilically enhanced inhibitors |
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- 2010-11-16 BR BR112012011528A patent/BR112012011528A2/pt not_active IP Right Cessation
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| AU2010319964A2 (en) | 2012-08-02 |
| EP2558099A2 (en) | 2013-02-20 |
| US20150045343A1 (en) | 2015-02-12 |
| MX2012005678A (es) | 2012-09-07 |
| US9505766B2 (en) | 2016-11-29 |
| CN102711765A (zh) | 2012-10-03 |
| US20130035325A1 (en) | 2013-02-07 |
| EP2558099A4 (en) | 2013-07-17 |
| WO2011060440A2 (en) | 2011-05-19 |
| BR112012011528A2 (pt) | 2019-09-24 |
| JP2013510886A (ja) | 2013-03-28 |
| CA2781056A1 (en) | 2011-05-19 |
| WO2011060440A3 (en) | 2011-11-03 |
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| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |