AU2012213390A1 - New azaindolylphenyl sulfonamides as serine/threonine kinase inhibitors - Google Patents
New azaindolylphenyl sulfonamides as serine/threonine kinase inhibitors Download PDFInfo
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- AU2012213390A1 AU2012213390A1 AU2012213390A AU2012213390A AU2012213390A1 AU 2012213390 A1 AU2012213390 A1 AU 2012213390A1 AU 2012213390 A AU2012213390 A AU 2012213390A AU 2012213390 A AU2012213390 A AU 2012213390A AU 2012213390 A1 AU2012213390 A1 AU 2012213390A1
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- Prior art keywords
- salkyl
- independently
- cycloalkyl
- alkyl
- compounds according
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- 150000003456 sulfonamides Chemical class 0.000 title description 11
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 title description 3
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- 229940043355 kinase inhibitor Drugs 0.000 title description 3
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
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- 125000001424 substituent group Chemical group 0.000 claims description 37
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Classifications
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- 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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- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A—HUMAN NECESSITIES
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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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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- 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
Landscapes
- Chemical & Material Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
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| EP11153087.9 | 2011-02-02 | ||
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| EP11181258.2 | 2011-09-14 | ||
| EP11181258 | 2011-09-14 | ||
| PCT/EP2012/051796 WO2012104388A1 (en) | 2011-02-02 | 2012-02-02 | New azaindolylphenyl sulfonamides as serine/threonine kinase inhibitors |
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| 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 |
| EP2571361A4 (en) | 2010-05-19 | 2013-11-13 | Univ North Carolina | PYRAZOLOPYRIMIDINE COMPOUNDS FOR CANCER TREATMENT |
| US8710055B2 (en) | 2010-12-21 | 2014-04-29 | Boehringer Ingelheim International Gmbh | Triazolylphenyl 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 |
| HRP20190281T1 (hr) | 2011-09-14 | 2019-05-31 | Samumed, Llc | Indazol-3-karboksamidi i njihova uporaba kao inhibitora signalizacijskog puta wnt/b-katenin |
| PH12017500997A1 (en) | 2012-04-04 | 2018-02-19 | Samumed Llc | Indazole inhibitors of the wnt signal pathway and therapeutic uses thereof |
| PL2770994T3 (pl) | 2012-05-04 | 2020-03-31 | Samumed, Llc | 1H-Pirazolo[3,4-b]pirydyny i ich zastosowania terapeutyczne |
| BR112014028424A2 (pt) | 2012-05-22 | 2018-04-24 | Univ North Carolina Chapel Hill | compostos de pirimidina para o tratamento de câncer |
| EP2909211A4 (en) | 2012-10-17 | 2016-06-22 | Univ North Carolina | PYRAZOLOPYRIMIDINE COMPOUNDS FOR CANCER TREATMENT |
| EP2925752A4 (en) | 2012-11-27 | 2016-06-01 | Univ North Carolina | PYRIMIDINE COMPOUNDS FOR CANCER TREATMENT |
| EP2943198B1 (en) | 2013-01-08 | 2019-07-17 | Samumed, LLC | 3-(benzoimidazol-2-yl)-indazole inhibitors of the wnt signaling pathway and therapeutic uses thereof |
| CA2906523A1 (en) | 2013-03-15 | 2014-09-25 | Myriad Genetics, Inc. | Genes and gene signatures for diagnosis and treatment of melanoma |
| CA2945128A1 (en) | 2014-04-11 | 2015-10-15 | The University Of North Carolina At Chapel Hill | Mertk-specific pyrimidine compounds |
| WO2016003810A1 (en) | 2014-07-02 | 2016-01-07 | Myriad Genetics, Inc. | Genes and gene signatures for diagnosis and treatment of melanoma |
| WO2016040193A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridine and therapeutic uses thereof |
| WO2016040180A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-benzo[d]imidazol-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040181A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040182A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 2-(1h-indazol-3-yl)-1h-imidazo[4,5-c]pyridine and therapeutic uses thereof |
| WO2016040190A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridine and therapeutic uses thereof |
| WO2016040185A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 2-(1h-indazol-3-yl)-3h-imidazo[4,5-b]pyridine and therapeutic uses thereof |
| WO2016040188A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040184A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| US10239881B2 (en) | 2014-10-27 | 2019-03-26 | University Health Network | RIPK2 inhibitors and method of treating cancer with same |
| US10285982B2 (en) | 2015-08-03 | 2019-05-14 | Samumed, Llc | 3-(1H-pyrrolo[2,3-B]pyridin-2-yl)-1H-pyrazolo[3,4-C]pyridines and therapeutic uses thereof |
| WO2017023975A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[2,3-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridines and therapeutic uses thereof |
| US10519169B2 (en) | 2015-08-03 | 2019-12-31 | Samumed, Llc | 3-(1H-pyrrolo[2,3-C]pyridin-2-yl)-1 H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| WO2017024015A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| US10166218B2 (en) | 2015-08-03 | 2019-01-01 | Samumed, Llc | 3-(1H-indol-2-yl)-1H-pyrazolo[3,4-C]pyridines and therapeutic uses thereof |
| US10392383B2 (en) | 2015-08-03 | 2019-08-27 | Samumed, Llc | 3-(1H-benzo[d]imidazol-2-yl)-1H-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| US10350199B2 (en) | 2015-08-03 | 2019-07-16 | Samumed, Llc | 3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-indazoles and therapeutic uses thereof |
| US10206909B2 (en) | 2015-08-03 | 2019-02-19 | Samumed, Llc | 3-(1H-pyrrolo[2,3-B]pyridin-2-yl)-1H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| WO2017023986A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc | 3-(1h-indol-2-yl)-1h-indazoles and therapeutic uses thereof |
| WO2017023984A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridines and therapeutic uses thereof |
| WO2017023987A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridines and therapeutic uses thereof |
| WO2017023972A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| US10231956B2 (en) | 2015-08-03 | 2019-03-19 | Samumed, Llc | 3-(1H-pyrrolo[3,2-C]pyridin-2-YL)-1 H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| US10188634B2 (en) | 2015-08-03 | 2019-01-29 | Samumed, Llc | 3-(3H-imidazo[4,5-C]pyridin-2-yl)-1 H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| US10285983B2 (en) | 2015-08-03 | 2019-05-14 | Samumed, Llc | 3-(1H-pyrrolo[2,3-B]pyridin-2-yl)-1H-pyrazolo[3,4-B] pyridines and therapeutic uses thereof |
| WO2017023993A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-indol-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| WO2017024010A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-indazoles and therapeutic uses thereof |
| EP3336090B1 (en) * | 2015-08-13 | 2020-07-22 | Beijing Hanmi Pharmaceutical Co., Ltd. | Irak4 inhibitor and use thereof |
| KR20180080262A (ko) | 2015-11-06 | 2018-07-11 | 사뮤메드, 엘엘씨 | 골관절염의 치료 |
| US10709708B2 (en) | 2016-03-17 | 2020-07-14 | The University Of North Carolina At Chapel Hill | Method of treating cancer with a combination of MER tyrosine kinase inhibitor and an epidermal growth factor receptor (EGFR) inhibitor |
| AR108325A1 (es) | 2016-04-27 | 2018-08-08 | Samumed Llc | Isoquinolin-3-il carboxamidas y preparación y uso de las mismas |
| ES2933109T3 (es) | 2016-06-01 | 2023-02-02 | Biosplice Therapeutics Inc | Proceso para preparar N-(5-(3-(7-(3-fluorofenil)-3h-imidazo[4,5-c]piridin-2-il)-1h-indazol-5-il)piridin-3-il)-3-metilbutanamida |
| CN110709082A (zh) | 2016-10-21 | 2020-01-17 | 萨穆梅德有限公司 | 吲唑-3-甲酰胺的使用方法及其作为Wnt/β-连环蛋白信号传导途径抑制剂的用途 |
| KR102558716B1 (ko) | 2016-11-07 | 2023-07-21 | 사뮤메드, 엘엘씨 | 단일-투여량, 즉시-사용가능한 주사용 제제 |
| DK3689868T3 (da) | 2016-12-01 | 2024-01-02 | Arvinas Operations Inc | Tetrahydronaphthalen- og tetrahydroisoquinolinderivater som østrogenreceptordegraderende midler |
| US11173211B2 (en) | 2016-12-23 | 2021-11-16 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of rapidly accelerated Fibrosarcoma polypeptides |
| AU2017382436C1 (en) * | 2016-12-23 | 2021-05-27 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of Rapidly Accelerated Fibrosarcoma polypeptides |
| JP7230041B2 (ja) * | 2017-10-26 | 2023-02-28 | ザイノミック・ファーマシューティカルズ・インコーポレイテッド | B-rafキナーゼ阻害物質の結晶塩 |
| IL290789B2 (en) | 2019-08-26 | 2025-09-01 | Arvinas Operations Inc | Methods for treating breast cancer with a history of tetrahydronaphthalene as estrogen receptor-disrupting agents |
| JP2023539663A (ja) | 2020-08-28 | 2023-09-15 | アルビナス・オペレーションズ・インコーポレイテッド | 急速進行性線維肉腫タンパク質分解化合物及び関連する使用方法 |
| CN116390916A (zh) | 2020-09-14 | 2023-07-04 | 阿尔维纳斯运营股份有限公司 | 用于靶向降解雌激素受体的化合物的结晶形式 |
| US12084453B2 (en) | 2021-12-10 | 2024-09-10 | Incyte Corporation | Bicyclic amines as CDK12 inhibitors |
| CN115010574B (zh) * | 2022-06-06 | 2024-01-05 | 爱斯特(成都)生物制药股份有限公司 | 1-溴-2-氯-4-氟-2碘苯的合成方法 |
| US11957759B1 (en) | 2022-09-07 | 2024-04-16 | Arvinas Operations, Inc. | Rapidly accelerated fibrosarcoma (RAF) degrading compounds and associated methods of use |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1326457A (zh) * | 1998-09-18 | 2001-12-12 | 巴斯福股份公司 | 作为激酶抑制剂的4-氨基吡咯并嘧啶 |
| TR200201505T2 (tr) * | 1999-09-17 | 2003-01-21 | Abbott Gmbh & Co.Kg | Terapötik maddeler olarak pirazolopirimidinler |
| US7166628B2 (en) | 2002-11-27 | 2007-01-23 | Boehringer Ingelheim Pharmaceuticals, Inc. | Cytokine inhibitors |
| US7521448B2 (en) * | 2003-08-21 | 2009-04-21 | Osi Pharmaceuticals, Inc. | N-substituted benzimidazolyl c-Kit inhibitors |
| US7511042B2 (en) | 2003-12-03 | 2009-03-31 | Boehringer Ingelheim Pharmaceuticals, Inc. | Triazole compounds |
| MXPA06007640A (es) * | 2004-01-12 | 2007-04-17 | Cytopia Res Pty Ltd | Inhibidores de quinasa selectivos. |
| SI1725544T1 (sl) | 2004-03-09 | 2009-10-31 | Boehringer Ingelheim Pharma | 3-(4-heterociklil-1,2,3-triazol-1-il)-N-aril-benzamidi kot inhibitorji proizvodnje citokinov za zdravljenje kroničnih vnetnih bolezni |
| US7485657B2 (en) | 2004-05-12 | 2009-02-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
| US20060004197A1 (en) * | 2004-07-02 | 2006-01-05 | Thomas Thrash | Sulfonamide-based compounds as protein tyrosine kinase inhibitors |
| 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 |
| GB0526246D0 (en) * | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| JP2009536618A (ja) | 2006-04-18 | 2009-10-15 | 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 | 4−及び5−イミダゾリル環を含むサイトカイン阻害化合物の製造方法及びその中間体 |
| BRPI0712795A2 (pt) | 2006-07-07 | 2012-09-04 | Boehringer Ingelheim Int | derivados de heteroarila substituìdos com fenila e uso dos mesmos como agentes antitumorais |
| EP2176249A2 (en) | 2007-07-02 | 2010-04-21 | Boehringer Ingelheim International GmbH | New chemical compounds |
| PE20090837A1 (es) | 2007-07-02 | 2009-07-24 | Boehringer Ingelheim Int | Nuevos compuestos quimicos |
| EP2170830B1 (en) * | 2007-07-17 | 2014-10-15 | Plexxikon, Inc. | 2-FLUORO-BENZENESULFONAMIDE COMPOUNDS AS Raf KINASE MODULATORS |
| AU2008323628B2 (en) * | 2007-11-15 | 2013-10-17 | Ym Biosciences Australia Pty Ltd | N-containing heterocyclic compounds |
| EA201100564A1 (ru) | 2008-09-29 | 2011-12-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Антипролиферативные соединения |
| WO2010042337A1 (en) | 2008-10-07 | 2010-04-15 | Merck Sharp & Dohme Corp. | Novel 6-azaindole aminopyrimidine derivatives having nik inhibitory activity |
| TW201041888A (en) * | 2009-05-06 | 2010-12-01 | Plexxikon Inc | Compounds and methods for kinase modulation, and indications therefor |
| JP2013503188A (ja) * | 2009-08-28 | 2013-01-31 | アレイ バイオファーマ、インコーポレイテッド | Raf阻害化合物およびその使用方法 |
| 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 |
| US8546443B2 (en) | 2010-12-21 | 2013-10-01 | Boehringer Ingelheim International Gmbh | Benzylic oxindole pyrimidines |
| 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 |
-
2012
- 2012-01-27 US US13/359,555 patent/US8889684B2/en active Active
- 2012-02-01 UY UY0001033890A patent/UY33890A/es unknown
- 2012-02-02 EP EP12701914.9A patent/EP2670749B1/en active Active
- 2012-02-02 BR BR112013019714A patent/BR112013019714A2/pt not_active IP Right Cessation
- 2012-02-02 MX MX2013008868A patent/MX2013008868A/es not_active Application Discontinuation
- 2012-02-02 CN CN2012800157100A patent/CN103476773A/zh active Pending
- 2012-02-02 CA CA2825279A patent/CA2825279A1/en not_active Abandoned
- 2012-02-02 AU AU2012213390A patent/AU2012213390A1/en not_active Abandoned
- 2012-02-02 JP JP2013552207A patent/JP5850952B2/ja active Active
- 2012-02-02 EA EA201300874A patent/EA201300874A1/ru unknown
- 2012-02-02 WO PCT/EP2012/051796 patent/WO2012104388A1/en not_active Ceased
- 2012-02-02 PH PH1/2013/501618A patent/PH12013501618A1/en unknown
- 2012-02-02 KR KR1020137022388A patent/KR20140014149A/ko not_active Withdrawn
-
2013
- 2013-07-09 IL IL227399A patent/IL227399A0/en unknown
- 2013-07-17 CL CL2013002063A patent/CL2013002063A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN103476773A (zh) | 2013-12-25 |
| CL2013002063A1 (es) | 2013-12-27 |
| WO2012104388A1 (en) | 2012-08-09 |
| US20130029993A1 (en) | 2013-01-31 |
| US8889684B2 (en) | 2014-11-18 |
| EP2670749B1 (en) | 2016-01-27 |
| CA2825279A1 (en) | 2012-08-09 |
| IL227399A0 (en) | 2013-09-30 |
| KR20140014149A (ko) | 2014-02-05 |
| JP5850952B2 (ja) | 2016-02-03 |
| EA201300874A1 (ru) | 2014-02-28 |
| UY33890A (es) | 2012-08-31 |
| EP2670749A1 (en) | 2013-12-11 |
| MX2013008868A (es) | 2013-08-14 |
| JP2014504622A (ja) | 2014-02-24 |
| PH12013501618A1 (en) | 2013-09-30 |
| BR112013019714A2 (pt) | 2016-10-18 |
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