JP2013516399A5 - - Google Patents
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- JP2013516399A5 JP2013516399A5 JP2012546501A JP2012546501A JP2013516399A5 JP 2013516399 A5 JP2013516399 A5 JP 2013516399A5 JP 2012546501 A JP2012546501 A JP 2012546501A JP 2012546501 A JP2012546501 A JP 2012546501A JP 2013516399 A5 JP2013516399 A5 JP 2013516399A5
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- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- substituents
- membered
- group
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- -1 one) Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 125000003003 spiro group Chemical group 0.000 description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 5
- 125000003386 piperidinyl group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 4
- 125000000168 pyrrolyl group Chemical group 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000006164 6-membered heteroaryl group Chemical group 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- AGTPSAZJSOQXHJ-UHFFFAOYSA-N (1-methylpiperidin-4-yl)methanamine Chemical compound CN1CCC(CN)CC1 AGTPSAZJSOQXHJ-UHFFFAOYSA-N 0.000 description 1
- SXKLBWHPONWBNP-UHFFFAOYSA-N 9-ethyl-n-[(1-methylpiperidin-4-yl)methyl]-3-[3-(trifluoromethoxy)phenyl]-7,8-dihydro-[1,2,4]triazolo[2,3]pyridazino[3,4-c][1,4]oxazin-10-amine Chemical compound C=12N(CC)CCOC2=NN2C(C=3C=C(OC(F)(F)F)C=CC=3)=NN=C2C=1NCC1CCN(C)CC1 SXKLBWHPONWBNP-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09380202 | 2009-12-31 | ||
| EP09380202.3 | 2009-12-31 | ||
| PCT/GB2010/002348 WO2011080510A1 (en) | 2009-12-31 | 2010-12-31 | Tricyclic compounds for use as kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013516399A JP2013516399A (ja) | 2013-05-13 |
| JP2013516399A5 true JP2013516399A5 (https=) | 2015-04-23 |
| JP5913126B2 JP5913126B2 (ja) | 2016-04-27 |
Family
ID=42200029
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012546501A Active JP5913126B2 (ja) | 2009-12-31 | 2010-12-31 | キナーゼ阻害剤としての使用のための三環式化合物 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9682991B2 (https=) |
| EP (1) | EP2519526B1 (https=) |
| JP (1) | JP5913126B2 (https=) |
| KR (1) | KR20120111739A (https=) |
| CN (1) | CN102791715B (https=) |
| AU (1) | AU2010338038B2 (https=) |
| CA (1) | CA2786002C (https=) |
| IL (1) | IL220701A0 (https=) |
| NZ (1) | NZ601033A (https=) |
| PH (1) | PH12012501361A1 (https=) |
| SG (1) | SG182297A1 (https=) |
| WO (1) | WO2011080510A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI617559B (zh) | 2010-12-22 | 2018-03-11 | 江蘇恆瑞醫藥股份有限公司 | ２－芳基咪唑并［１，２－ｂ］嗒．２－苯基咪唑并［１，２－ａ］吡啶，和２－苯基咪唑并［１，２－ａ］吡衍生物 |
| WO2013004984A1 (en) * | 2011-07-07 | 2013-01-10 | Centro Nacional De Investigaciones Oncologicas (Cnio) | Tricyclic compounds for use as kinase inhibitors |
| WO2013005041A1 (en) * | 2011-07-07 | 2013-01-10 | Centro Nacional De Investigaciones Oncológicas (Cnio) | Tricyclic heterocyclic compounds as kinase inhibitors |
| WO2013005057A1 (en) * | 2011-07-07 | 2013-01-10 | Centro Nacional De Investigaciones Oncológicas (Cnio) | New compounds |
| CN104768554B (zh) | 2012-11-07 | 2018-04-17 | 霍夫曼-拉罗奇有限公司 | 三唑并化合物 |
| CN108931633B (zh) * | 2018-05-22 | 2021-08-27 | 郑州大学第一附属医院 | 胆囊癌诊断和预后判断标志物pim1 |
| AU2021360636A1 (en) * | 2020-10-16 | 2023-06-15 | Shanghai De Novo Pharmatech Co., Ltd. | Triheterocyclic derivative, and pharmaceutical composition and application thereof |
| CN113214255B (zh) * | 2021-04-22 | 2023-09-29 | 无锡合全药业有限公司 | 2,6-二氮杂螺[3.5]壬烷-6-甲酸叔丁基酯及其盐的合成方法 |
| US20250042918A1 (en) | 2021-12-01 | 2025-02-06 | Fundación Del Sector Públlco Estatal Centro Nacional De Investigaciones Oncológicas Carlos III | Compounds |
| EP4279074A1 (en) * | 2022-05-19 | 2023-11-22 | Georg-August-Universität Göttingen Stiftung Öffentlichen Rechts, Universitätsmedizin | Azolo compounds for treatment of fibrotic diseases |
| EP4458358A1 (en) * | 2023-05-02 | 2024-11-06 | Tietze Chemical Consulting UG | Pyridazine compounds for antifibrotic therapy |
Family Cites Families (65)
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|---|---|---|---|---|
| JPS603080B2 (ja) | 1976-08-10 | 1985-01-25 | 三菱化学株式会社 | Ｓ―トリアゾロ〔３，４ ―α〕〔５，６，７，８〕テトラヒドロ フタラジン類 |
| GR70309B (https=) | 1979-10-29 | 1982-09-08 | Dow Chemical Co | |
| PH21834A (en) | 1982-01-18 | 1988-03-17 | Lepetit Spa | New 6-substituted-s-triazolo(3,4-a)phthalazine derivatives |
| US4487930A (en) | 1982-09-07 | 1984-12-11 | The Dow Chemical Company | 6-[(Cyclic amino)alkylamino]-tetrahydrotriazolo[3,4-a]phthalazines |
| FR2601675B1 (fr) | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent |
| US5011835A (en) | 1990-02-07 | 1991-04-30 | Merrell Dow Pharmaceuticals Inc. | Substituted triazolopyridazines, pharmaceutical compositions and use |
| US5714512A (en) | 1991-07-08 | 1998-02-03 | Rhone-Poulenc Rorer, S.A. | Compositions containing taxane derivatives |
| US5698582A (en) | 1991-07-08 | 1997-12-16 | Rhone-Poulenc Rorer S.A. | Compositions containing taxane derivatives |
| US5750561A (en) | 1991-07-08 | 1998-05-12 | Rhone-Poulenc Rorer, S.A. | Compositions containing taxane derivatives |
| TW211013B (https=) | 1991-12-27 | 1993-08-11 | Takeda Pharm Industry Co Ltd | |
| LT3200B (en) | 1992-03-18 | 1995-03-27 | Takeda Chemical Industries Ltd | Triazolopyridazine methodfor production thereof and use |
| FR2698543B1 (fr) | 1992-12-02 | 1994-12-30 | Rhone Poulenc Rorer Sa | Nouvelles compositions à base de taxoides. |
| EP0620224B1 (en) | 1993-04-12 | 1998-07-15 | Takeda Chemical Industries, Ltd. | Triazolopyridazine derivatives, their production and use |
| WO1998004560A1 (en) | 1996-07-25 | 1998-02-05 | Merck Sharp & Dohme Limited | SUBSTITUTED TRIAZOLO PYRIDAZINE DERIVATIVES AS INVERSE AGONISTS OF THE GABAAα5 RECEPTOR SUBTYPE |
| KR20000029548A (ko) | 1996-07-25 | 2000-05-25 | 더블유. 지. 콜 | 가바수용체에대한리간드로서의치환된트리아졸로-피리다진유도체 |
| ES2137113B1 (es) | 1997-07-29 | 2000-09-16 | Almirall Prodesfarma Sa | Nuevos derivados de triazolo-piridazinas heterociclicos. |
| WO1999025353A1 (en) | 1997-11-13 | 1999-05-27 | Merck Sharp & Dohme Limited | Therapeutic uses of triazolo-pyridazine derivatives |
| RS49779B (sr) | 1998-01-12 | 2008-06-05 | Glaxo Group Limited, | Biciklična heteroaromatična jedinjenja kao inhibitori protein tirozin kinaze |
| GB9801208D0 (en) | 1998-01-21 | 1998-03-18 | Merck Sharp & Dohme | Therapeutic agents |
| GB9813576D0 (en) | 1998-06-24 | 1998-08-19 | Merck Sharp & Dohme | Therapeutic agents |
| GB2345443A (en) | 1999-01-08 | 2000-07-12 | Merck Sharp & Dohme | Use of triazolo-pyridazines for treating premenstrual syndrome |
| US6933299B1 (en) | 1999-07-09 | 2005-08-23 | Smithkline Beecham Corporation | Anilinoquinazolines as protein tyrosine kinase inhibitors |
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| TWI271406B (en) | 1999-12-13 | 2007-01-21 | Eisai Co Ltd | Tricyclic condensed heterocyclic compounds, preparation method of the same and pharmaceuticals comprising the same |
| AU2001273071B2 (en) | 2000-06-30 | 2005-09-08 | Glaxo Group Limited | Quinazoline ditosylate salt compounds |
| 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 |
| DE60203260T2 (de) | 2001-01-16 | 2006-02-02 | Glaxo Group Ltd., Greenford | Pharmazeutische kombination, die ein 4-chinazolinamin und paclitaxel, carboplatin oder vinorelbin enthält, zur behandlung von krebs |
| US20040102455A1 (en) * | 2001-01-30 | 2004-05-27 | Burns Christopher John | Method of inhibiting kinases |
| US6958334B2 (en) | 2001-04-10 | 2005-10-25 | Merck & Co., Inc. | Inhibitors of Akt activity |
| US20040106540A1 (en) | 2001-04-10 | 2004-06-03 | Barnett Stanley F | Method of treating cancer |
| IL149462A0 (en) | 2001-05-09 | 2002-11-10 | Warner Lambert Co | Method of treating or inhibiting neutrophil chemotaxis by administering a mek inhibitor |
| MXPA04005939A (es) | 2002-01-22 | 2005-01-25 | Warner Lambert Co | 2-(piridin-2-ilamino)-pirido[2,3-d]pirimidin-7-onas. |
| EP1496981A2 (en) | 2002-04-08 | 2005-01-19 | Merck & Co., Inc. | Method of treating cancer |
| DE10239042A1 (de) | 2002-08-21 | 2004-03-04 | Schering Ag | Makrozyclische Pyrimidine, deren Herstellung und Verwendung als Arzneimittel |
| US20040102360A1 (en) | 2002-10-30 | 2004-05-27 | Barnett Stanley F. | Combination therapy |
| MXPA05003431A (es) | 2002-11-15 | 2005-07-05 | Warner Lambert Co | Quimioterapia de combinacion. |
| WO2004058769A2 (en) | 2002-12-18 | 2004-07-15 | Vertex Pharmaceuticals Incorporated | Triazolopyridazines as protein kinases inhibitors |
| AU2004255934B2 (en) | 2003-07-11 | 2010-02-25 | Warner-Lambert Company Llc | Isethionate salt of a selective CDK4 inhibitor |
| CN1871008A (zh) | 2003-10-21 | 2006-11-29 | 默克公司 | 用于治疗神经病变性疼痛的三唑并－哒嗪化合物和它们的衍生物 |
| NZ546011A (en) | 2003-10-21 | 2009-09-25 | Warner Lambert Co | Polymorphic form of N-[(R)-2,3-dihydroxy-propoxy]-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-benzamide |
| AU2005212096B2 (en) | 2004-02-18 | 2010-12-16 | Msd K.K. | Nitrogenous fused heteroaromatic ring derivative |
| WO2005094830A1 (en) | 2004-03-30 | 2005-10-13 | Pfizer Products Inc. | Combinations of signal transduction inhibitors |
| KR101368093B1 (ko) | 2004-09-02 | 2014-03-14 | 다케다 게엠베하 | 트리아졸로프탈라진 |
| GB0423653D0 (en) | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| CN101103033B (zh) | 2005-01-05 | 2010-08-04 | 尼科梅德有限责任公司 | 作为pde2抑制剂的三唑并酞嗪 |
| CA2591991C (en) | 2005-01-05 | 2013-11-19 | Altana Pharma Ag | Triazolophthalazines |
| TW200639163A (en) | 2005-02-04 | 2006-11-16 | Genentech Inc | RAF inhibitor compounds and methods |
| WO2007129161A2 (en) | 2006-04-26 | 2007-11-15 | F. Hoffmann-La Roche Ag | Thieno [3, 2-d] pyrimidine derivative useful as pi3k inhibitor |
| BRPI0716880A2 (pt) | 2006-09-08 | 2013-10-15 | Pfizer Prod Inc | Síntese de 2-(piridin-2-ilamino)-pirido[2,3-d]pirimidin-7-onas |
| WO2008109104A1 (en) | 2007-03-07 | 2008-09-12 | The Regents Of The University Of California | Bivalent inhibitors of akt protein kinase |
| EP2142551B1 (en) | 2007-04-17 | 2015-10-14 | Bristol-Myers Squibb Company | Fused heterocyclic 11-beta-hydroxysteroid dehydrogenase type i inhibitors |
| DE102007032349A1 (de) * | 2007-07-11 | 2009-01-15 | Bayer Healthcare Ag | Imidazo-, Pyrazolopyrazine und Imidazotriazine und ihre Verwendung |
| EP2205242B1 (en) | 2007-09-12 | 2015-04-15 | Genentech, Inc. | Combinations of phosphoinositide 3-kinase inhibitor compounds and chemotherapeutic agents, and methods of use |
| HUE025976T2 (en) | 2007-09-27 | 2016-05-30 | Fund Centro Nac De Investig Oncologicas Carlos Iii | Imidazolothiadiazoles for use as protein kinase inhibitors |
| EP2211615A4 (en) | 2007-10-22 | 2010-10-13 | Glaxosmithkline Llc | PYRIDOSULFONAMIDE DERIVATIVES AS PI3 KINASE INHIBITORS |
| JP5348725B2 (ja) | 2007-10-25 | 2013-11-20 | ジェネンテック， インコーポレイテッド | チエノピリミジン化合物の製造方法 |
| EP2217601A1 (en) * | 2007-11-08 | 2010-08-18 | Centro Nacional de Investigaciones Oncológicas (CNIO) | Imidazopyridazines for use as protein kinase inhibitors |
| DK2644194T3 (en) | 2008-03-18 | 2017-07-03 | Genentech Inc | Combinations of an anti-HER2 antibody-drug conjugate and docetaxel |
| WO2010085597A1 (en) | 2009-01-23 | 2010-07-29 | Incyte Corporation | Macrocyclic compounds and their use as kinase inhibitors |
| JP5709766B2 (ja) | 2009-03-12 | 2015-04-30 | ジェネンテック， インコーポレイテッド | 造血器腫瘍の治療のためのホスホイノシチド３キナーゼ阻害剤化合物と化学療法剤の併用 |
| JP2012521354A (ja) | 2009-03-20 | 2012-09-13 | アムジエン・インコーポレーテツド | Ｐｉ３キナーゼの阻害薬 |
| CN102361878A (zh) | 2009-03-24 | 2012-02-22 | 住友化学株式会社 | 用于制备硼酸酯化合物的方法 |
| US20120214828A1 (en) | 2009-08-24 | 2012-08-23 | Georgia Hatzivassiliou | Determining sensitivity of cells to b-raf inhibitor treatment by detecting kras mutation and rtk expression levels |
| CA2776944A1 (en) | 2009-10-12 | 2011-05-12 | F. Hoffmann-La Roche Ag | Combinations of a pi3k inhibitor and a mek inhibitor |
| WO2011130654A1 (en) | 2010-04-16 | 2011-10-20 | Genentech, Inc. | Fox03a as predictive biomarker for pi3k/akt kinase pathway inhibitor efficacy |
-
2010
- 2010-12-21 PH PH1/2012/501361A patent/PH12012501361A1/en unknown
- 2010-12-31 KR KR1020127020212A patent/KR20120111739A/ko not_active Withdrawn
- 2010-12-31 JP JP2012546501A patent/JP5913126B2/ja active Active
- 2010-12-31 US US13/519,872 patent/US9682991B2/en active Active - Reinstated
- 2010-12-31 AU AU2010338038A patent/AU2010338038B2/en not_active Ceased
- 2010-12-31 CA CA2786002A patent/CA2786002C/en active Active
- 2010-12-31 NZ NZ601033A patent/NZ601033A/en not_active IP Right Cessation
- 2010-12-31 CN CN201080064929.0A patent/CN102791715B/zh not_active Expired - Fee Related
- 2010-12-31 WO PCT/GB2010/002348 patent/WO2011080510A1/en not_active Ceased
- 2010-12-31 EP EP10803613.8A patent/EP2519526B1/en active Active
- 2010-12-31 SG SG2012048476A patent/SG182297A1/en unknown
-
2012
- 2012-07-01 IL IL220701A patent/IL220701A0/en unknown
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