CA2874967C - Pteridines as fgfr inhibitors - Google Patents
Pteridines as fgfr inhibitors Download PDFInfo
- Publication number
- CA2874967C CA2874967C CA2874967A CA2874967A CA2874967C CA 2874967 C CA2874967 C CA 2874967C CA 2874967 A CA2874967 A CA 2874967A CA 2874967 A CA2874967 A CA 2874967A CA 2874967 C CA2874967 C CA 2874967C
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- 6alkyl
- substituted
- cancer
- nr14r15
- 4alkyl
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/02—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4
- C07D475/04—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
-
- 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
- A61K31/495—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D403/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
- C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (7)
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| US201261653081P | 2012-05-30 | 2012-05-30 | |
| GB1209613.7 | 2012-05-30 | ||
| US61/653,081 | 2012-05-30 | ||
| GBGB1209613.7A GB201209613D0 (en) | 2012-05-30 | 2012-05-30 | New compounds |
| US201361782233P | 2013-03-14 | 2013-03-14 | |
| US61/782,233 | 2013-03-14 | ||
| PCT/GB2013/051427 WO2013179033A1 (en) | 2012-05-30 | 2013-05-30 | Pteridines as fgfr inhibitors |
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| CA2874967A1 CA2874967A1 (en) | 2013-12-05 |
| CA2874967C true CA2874967C (en) | 2021-11-09 |
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| EP (1) | EP2855480B1 (h) |
| JP (1) | JP6363068B2 (h) |
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| CN (1) | CN104507944B (h) |
| AU (1) | AU2013269316C1 (h) |
| BR (1) | BR112014029709B1 (h) |
| CA (1) | CA2874967C (h) |
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| ES (1) | ES2739348T3 (h) |
| GB (1) | GB201209613D0 (h) |
| HR (1) | HRP20191202T1 (h) |
| HU (1) | HUE045663T2 (h) |
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| RU (1) | RU2702906C2 (h) |
| SI (1) | SI2855480T1 (h) |
| WO (1) | WO2013179033A1 (h) |
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| GB201007286D0 (en) | 2010-04-30 | 2010-06-16 | Astex Therapeutics Ltd | New compounds |
| GB201020179D0 (en) | 2010-11-29 | 2011-01-12 | Astex Therapeutics Ltd | New compounds |
| GB201118656D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201118654D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201118675D0 (en) | 2011-10-28 | 2011-12-14 | Astex Therapeutics Ltd | New compounds |
| GB201118652D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201209613D0 (en) | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
| GB201209609D0 (en) | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
| GB201307577D0 (en) | 2013-04-26 | 2013-06-12 | Astex Therapeutics Ltd | New compounds |
| KR102479696B1 (ko) | 2014-03-26 | 2022-12-22 | 아스텍스 테라퓨틱스 리미티드 | Fgfr 억제제 및 igf1r 억제제의 조합물 |
| PT3122358T (pt) | 2014-03-26 | 2021-03-04 | Astex Therapeutics Ltd | Combinações de inibidores do fgfr e cmet para o tratamento do cancro |
| JO3512B1 (ar) | 2014-03-26 | 2020-07-05 | Astex Therapeutics Ltd | مشتقات كينوكسالين مفيدة كمعدلات لإنزيم fgfr كيناز |
| WO2015160980A1 (en) | 2014-04-15 | 2015-10-22 | Thoratec Corporation | Heart pump providing adjustable out flow |
| CN103992262B (zh) * | 2014-06-12 | 2015-11-11 | 苏州明锐医药科技有限公司 | 塞瑞替尼及其中间体的制备方法 |
| JOP20200201A1 (ar) | 2015-02-10 | 2017-06-16 | Astex Therapeutics Ltd | تركيبات صيدلانية تشتمل على n-(3.5- ثنائي ميثوكسي فينيل)-n'-(1-ميثيل إيثيل)-n-[3-(ميثيل-1h-بيرازول-4-يل) كينوكسالين-6-يل]إيثان-1.2-ثنائي الأمين |
| US10478494B2 (en) | 2015-04-03 | 2019-11-19 | Astex Therapeutics Ltd | FGFR/PD-1 combination therapy for the treatment of cancer |
| RU2747645C2 (ru) * | 2015-09-23 | 2021-05-11 | Янссен Фармацевтика Нв | Новые соединения |
| HUE057090T2 (hu) | 2015-09-23 | 2022-04-28 | Janssen Pharmaceutica Nv | BI-heteroaril-szubsztituált 1,4-benzodiazepinek és alkalmazásuk rák kezelésében |
| WO2017070708A1 (en) | 2015-10-23 | 2017-04-27 | Array Biopharma, Inc. | 2-aryl- and 2-heteroaryl-substituted 2-pyridazin-3(2h)-one compounds as inhibitors of fgfr tyrosine kinases |
| DK3442947T3 (da) * | 2016-04-15 | 2023-09-04 | Epizyme Inc | Aminsubstituerede aryl- eller heteroarylforbindelser som ehmt1- og ehmt2-hæmmere |
| CN118021814A (zh) | 2017-04-21 | 2024-05-14 | Epizyme股份有限公司 | 用ehmt2抑制剂进行的组合疗法 |
| EP3722282B1 (en) * | 2017-12-07 | 2024-09-11 | Harbin Zhenbao Pharmaceutical Co., Ltd. | Salt form and crystal form serving as fgfr and vegfr inhibitor compounds, and preparation method therefor |
| US10992078B2 (en) | 2018-01-29 | 2021-04-27 | Bard Access Systems, Inc. | Connection system for establishing an electrical connection through a drape and methods thereof |
| US10772696B2 (en) | 2018-05-18 | 2020-09-15 | Bard Access Systems, Inc. | Connection systems and methods thereof for establishing an electrical connection through a drape |
| JP2022515197A (ja) | 2018-12-19 | 2022-02-17 | アレイ バイオファーマ インコーポレイテッド | がんを治療するためのｆｇｆｒ阻害剤としての７－（（３，５－ジメトキシフェニル）アミノ）キノキサリン誘導体 |
| US12180207B2 (en) | 2018-12-19 | 2024-12-31 | Array Biopharma Inc. | Substituted pyrazolo[1,5-a]pyridine compounds as inhibitors of FGFR tyrosine kinases |
| BR112021018168B1 (pt) | 2019-03-21 | 2023-11-28 | Onxeo | Composição farmacêutica, combinação e kit compreendendo uma molécula dbait e um inibidor de quinase para o tratamento de câncer |
| EP3996571A4 (en) | 2019-07-12 | 2023-06-28 | Bard Access Systems, Inc. | Catheter tracking and placement system including light emitting diode array |
| WO2021026502A1 (en) | 2019-08-08 | 2021-02-11 | Bard Access Systems, Inc. | Optical-fiber connector modules including shape-sensing systems and methods thereof |
| JP2023500906A (ja) | 2019-11-08 | 2023-01-11 | インサーム（インスティテュ ナシオナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシェ メディカル） | キナーゼ阻害剤に対する獲得抵抗性を有するがんの処置方法 |
| US20230115528A1 (en) | 2019-12-30 | 2023-04-13 | Tyra Biosciences, Inc. | Indazole compounds |
| WO2021138392A1 (en) | 2019-12-30 | 2021-07-08 | Tyra Biosciences, Inc. | Aminopyrimidine compounds |
| BE1027936B1 (nl) | 2019-12-30 | 2021-08-03 | Kreco Nv | Coccolitisch krijtproduct voor toepassing in landbouw en waterbeheer |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| PE20240687A1 (es) | 2020-12-30 | 2024-04-10 | Tyra Biosciences Inc | Compuestos de indazol como inhibidores de cinasas |
| CA3211124A1 (en) | 2021-02-26 | 2022-09-01 | Tyra Biosciences, Inc. | Aminopyrimidine compounds and methods of their use |
| IL317558A (en) | 2022-06-29 | 2025-02-01 | Tyra Biosciences Inc | Indazole compounds |
| TW202408493A (zh) | 2022-06-29 | 2024-03-01 | 美商泰拉生物科學公司 | 多晶形化合物及其用途 |
| CN114984019B (zh) * | 2022-07-15 | 2023-08-22 | 山东中医药大学 | 一种铁死亡抑制剂化合物及在肝损伤修复领域的应用 |
| WO2024138112A1 (en) | 2022-12-22 | 2024-06-27 | Tyra Biosciences, Inc. | Indazole compounds |
| TW202504611A (zh) | 2023-03-30 | 2025-02-01 | 美商銳新醫藥公司 | 用於誘導ｒａｓ ｇｔｐ水解之組合物及其用途 |
| TW202508595A (zh) | 2023-05-04 | 2025-03-01 | 美商銳新醫藥公司 | 用於ｒａｓ相關疾病或病症之組合療法 |
| US20250049810A1 (en) | 2023-08-07 | 2025-02-13 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| US20250154171A1 (en) | 2023-10-12 | 2025-05-15 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025129014A1 (en) | 2023-12-15 | 2025-06-19 | Tyra Biosciences, Inc. | Indazole compounds for the treatment of cancer |
| WO2025171296A1 (en) | 2024-02-09 | 2025-08-14 | Revolution Medicines, Inc. | Ras inhibitors |
Family Cites Families (125)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2940972A (en) * | 1957-06-27 | 1960-06-14 | Thomae Gmbh Dr K | Tri-and tetra-substituted pteridine derivatives |
| US4666828A (en) | 1984-08-15 | 1987-05-19 | The General Hospital Corporation | Test for Huntington's disease |
| US4683202A (en) | 1985-03-28 | 1987-07-28 | Cetus Corporation | Process for amplifying nucleic acid sequences |
| US4801531A (en) | 1985-04-17 | 1989-01-31 | Biotechnology Research Partners, Ltd. | Apo AI/CIII genomic polymorphisms predictive of atherosclerosis |
| US5272057A (en) | 1988-10-14 | 1993-12-21 | Georgetown University | Method of detecting a predisposition to cancer by the use of restriction fragment length polymorphism of the gene for human poly (ADP-ribose) polymerase |
| US5192659A (en) | 1989-08-25 | 1993-03-09 | Genetype Ag | Intron sequence analysis method for detection of adjacent and remote locus alleles as haplotypes |
| GB9125001D0 (en) * | 1991-11-25 | 1992-01-22 | Ici Plc | Heterocyclic compounds |
| AU6909194A (en) | 1993-05-14 | 1994-12-12 | Board Of Regents, The University Of Texas System | Preparation of n-cyanodithioimino-carbonates and 3-mercapto-5-amino-1h-1,2,4-triazole |
| US5700823A (en) | 1994-01-07 | 1997-12-23 | Sugen, Inc. | Treatment of platelet derived growth factor related disorders such as cancers |
| US6331555B1 (en) | 1995-06-01 | 2001-12-18 | University Of California | Treatment of platelet derived growth factor related disorders such as cancers |
| US6218529B1 (en) | 1995-07-31 | 2001-04-17 | Urocor, Inc. | Biomarkers and targets for diagnosis, prognosis and management of prostate, breast and bladder cancer |
| CA2744096C (en) | 1996-07-31 | 2013-07-30 | Laboratory Corporation Of America Holdings | Biomarkers and targets for diagnosis, prognosis and management of prostate disease |
| TW472045B (en) * | 1996-09-25 | 2002-01-11 | Astra Ab | Protein kinase C inhibitor compounds, method for their preparation, pharmaceutical composition thereof and intermediate used for their preparation |
| PL194980B1 (pl) | 1997-05-28 | 2007-07-31 | Aventis Pharma Inc | Nowe związki chinolinowe i chinoksalinowe, kompozycja farmaceutyczna je zawierająca oraz ich zastosowanie |
| UA71555C2 (en) | 1997-10-06 | 2004-12-15 | Zentaris Gmbh | Methods for modulating function of serine/threonine protein kinases by 5-azaquinoline derivatives |
| WO2000042026A1 (en) | 1999-01-15 | 2000-07-20 | Novo Nordisk A/S | Non-peptide glp-1 agonists |
| US7169778B2 (en) * | 1999-09-15 | 2007-01-30 | Warner-Lambert Company | Pteridinones as kinase inhibitors |
| DE10013318A1 (de) | 2000-03-17 | 2001-09-20 | Merck Patent Gmbh | Formulierung enthaltend Chinoxalinderivate |
| WO2002076985A1 (en) | 2001-03-23 | 2002-10-03 | Smithkline Beecham Corporation | Compounds useful as kinase inhibitors for the treatment of hyperproliferative diseases |
| JP2003013463A (ja) * | 2001-06-28 | 2003-01-15 | Works 21:Kk | マンホール施工方法 |
| EP1458383B1 (en) | 2001-12-18 | 2007-11-21 | Merck & Co., Inc. | Heteroaryl substituted pyrazole modulators of metabotropic glutamate receptor-5 |
| RU2323215C2 (ru) | 2001-12-24 | 2008-04-27 | Астразенека Аб | Замещенные производные хиназолина как ингибиторы ауроракиназы |
| JP2003213463A (ja) | 2002-01-17 | 2003-07-30 | Sumitomo Chem Co Ltd | 金属腐食防止剤および洗浄液 |
| AU2003223467B2 (en) | 2002-04-08 | 2007-10-04 | Merck Sharp & Dohme Corp. | Inhibitors of Akt activity |
| US6962995B2 (en) | 2002-07-10 | 2005-11-08 | E. I. Du Pont De Nemours And Company | Charge transport compositions and electronic devices made with such compositions |
| US7825132B2 (en) | 2002-08-23 | 2010-11-02 | Novartis Vaccines And Diagnostics, Inc. | Inhibition of FGFR3 and treatment of multiple myeloma |
| AU2003282726B2 (en) | 2002-10-03 | 2010-10-07 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| AR043059A1 (es) | 2002-11-12 | 2005-07-13 | Bayer Pharmaceuticals Corp | Derivados de indolil pirazinona utiles para el tratamiento de trastornos hiper-proliferativos |
| US7098332B2 (en) | 2002-12-20 | 2006-08-29 | Hoffmann-La Roche Inc. | 5,8-Dihydro-6H-pyrido[2,3-d]pyrimidin-7-ones |
| WO2004065378A1 (en) | 2003-01-17 | 2004-08-05 | Warner-Lambert Company Llc | 2-aminopyridine substituted heterocycles as inhibitors of cellular proliferation |
| EP1620413A2 (en) | 2003-04-30 | 2006-02-01 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| CA2525547C (en) | 2003-05-14 | 2012-07-03 | Torreypines Therapeutics, Inc. | Compounds and uses thereof in modulating amyloid beta |
| DE10323345A1 (de) | 2003-05-23 | 2004-12-16 | Zentaris Gmbh | Neue Pyridopyrazine und deren Verwendung als Kinase-Inhibitoren |
| ES2316985T3 (es) | 2003-05-23 | 2009-04-16 | Aterna Zentaris Gmbh | Nuevas piridopirazidinas y su uso como moduladores de quinasas. |
| WO2005007099A2 (en) | 2003-07-10 | 2005-01-27 | Imclone Systems Incorporated | Pkb inhibitors as anti-tumor agents |
| US7339065B2 (en) | 2003-07-21 | 2008-03-04 | Bethesda Pharmaceuticals, Inc. | Design and synthesis of optimized ligands for PPAR |
| RU2355687C2 (ru) * | 2003-08-01 | 2009-05-20 | Дженелэбс Текнолоджиз, Инк | Бициклические производные имидазола в качестве средства против вирусов семейства flaviviridae |
| AU2004283479A1 (en) * | 2003-10-17 | 2005-05-06 | 4 Aza Bioscience Nv | Heterocycle-substituted pteridine derivatives and their use in therapy |
| CN102225926A (zh) | 2003-11-07 | 2011-10-26 | 诺华疫苗和诊断公司 | 具有改进药物特性的喹啉酮类化合物的药学上可接受的盐 |
| WO2005054201A1 (en) | 2003-11-20 | 2005-06-16 | Janssen Pharmaceutica N.V. | 6-alkenyl and 6-phenylalkyl substituted 2-quinolinones and 2-quinoxalinones as poly(adp-ribose) polymerase inhibitors |
| CN100554264C (zh) | 2003-11-24 | 2009-10-28 | 弗·哈夫曼-拉罗切有限公司 | 吡唑基与咪唑基嘧啶 |
| HRP20100675T1 (hr) | 2003-12-23 | 2011-01-31 | Astex Therapeutics Limited | Derivati pirazola kao modulatori protein kinaze |
| US7098222B2 (en) | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| US7205316B2 (en) | 2004-05-12 | 2007-04-17 | Abbott Laboratories | Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands |
| KR20070048798A (ko) | 2004-08-31 | 2007-05-09 | 아스트라제네카 아베 | 퀴나졸리논 유도체 및 이것의 ｂ-ｒａｆ 억제제로서의 용도 |
| RU2405781C2 (ru) | 2004-10-14 | 2010-12-10 | Ф.Хоффманн-Ля Рош Аг | 1, 5-нафтиридиназолидиноны, обладающие cdk1 антипролиферативной активностью |
| PT1830869E (pt) | 2004-12-24 | 2013-08-22 | Spinifex Pharm Pty Ltd | Método de tratamento ou profilaxia |
| WO2006084338A1 (en) | 2005-02-14 | 2006-08-17 | Bionomics Limited | Novel tubulin polymerisation inhibitors |
| US9271963B2 (en) | 2005-03-03 | 2016-03-01 | Universitat Des Saarlandes | Selective inhibitors of human corticosteroid synthases |
| EP1881986A2 (en) | 2005-05-12 | 2008-01-30 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| BRPI0611521A2 (pt) | 2005-05-18 | 2010-09-14 | Wyeth Corp | inibidores de 4,6-diamino-[1,7]naftiridina-3-carbonitrila de quìnase tpl2 e métodos de fabricação e uso dos mesmos |
| GB0513692D0 (en) | 2005-07-04 | 2005-08-10 | Karobio Ab | Novel pharmaceutical compositions |
| ES2456000T3 (es) | 2005-08-26 | 2014-04-21 | Merck Serono Sa | Derivados de pirazina y su uso como inhibidores de PI3K |
| EP1790342A1 (de) | 2005-11-11 | 2007-05-30 | Zentaris GmbH | Pyridopyrazin-Derivate und deren Verwendung als Modulatoren der Signaltransduktionswege |
| US8217042B2 (en) | 2005-11-11 | 2012-07-10 | Zentaris Gmbh | Pyridopyrazines and their use as modulators of kinases |
| WO2007054556A1 (de) | 2005-11-11 | 2007-05-18 | Æterna Zentaris Gmbh | Neue pyridopyrazine und deren verwendung als modulatoren von kinasen |
| CN101374843B (zh) | 2005-12-21 | 2012-09-05 | 詹森药业有限公司 | 作为酪氨酸激酶调节剂的三唑并哒嗪 |
| JP2009535393A (ja) | 2006-05-01 | 2009-10-01 | ファイザー・プロダクツ・インク | 置換２−アミノ縮合複素環式化合物 |
| GB0609621D0 (en) | 2006-05-16 | 2006-06-21 | Astrazeneca Ab | Novel co-crystal |
| ATE549338T1 (de) | 2006-05-24 | 2012-03-15 | Boehringer Ingelheim Int | Substituierte pteridine, die mit einem viergliedrigen heterocyclus substituiert sind |
| WO2008003702A2 (en) | 2006-07-03 | 2008-01-10 | Vereniging Voor Christelijk Hoger Onderwijs, Wetenschappelijk Onderzoek En Patientenzorg | Fused bicyclic compounds interacting with the histamine h4 receptor |
| JP2008127446A (ja) | 2006-11-20 | 2008-06-05 | Canon Inc | １，５−ナフチリジン化合物及び有機発光素子 |
| CA2672828A1 (en) | 2006-12-13 | 2008-06-26 | Schering Corporation | Methods of treatment |
| AU2007336811A1 (en) | 2006-12-21 | 2008-07-03 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| CN101652352A (zh) | 2006-12-22 | 2010-02-17 | 诺瓦提斯公司 | 用于抑制pdk1的喹唑啉类 |
| CN101679408B (zh) | 2006-12-22 | 2016-04-27 | Astex治疗学有限公司 | 作为fgfr抑制剂的双环杂环化合物 |
| KR20080062876A (ko) | 2006-12-29 | 2008-07-03 | 주식회사 대웅제약 | 신규한 항진균성 트리아졸 유도체 |
| US20100234386A1 (en) | 2007-05-10 | 2010-09-16 | Chaudhari Amita | Quinoxaline derivatives as pi3 kinase inhibitors |
| EP1990342A1 (en) | 2007-05-10 | 2008-11-12 | AEterna Zentaris GmbH | Pyridopyrazine Derivatives, Process of Manufacturing and Uses thereof |
| JP2010529031A (ja) | 2007-05-29 | 2010-08-26 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | Ｐｉ３キナーゼ阻害剤としてのナフチリジン誘導体 |
| AR066879A1 (es) | 2007-06-08 | 2009-09-16 | Novartis Ag | Derivados de quinoxalina como inhibidores de la actividad de cinasa de tirosina de las cinasas janus |
| KR20130008625A (ko) | 2007-06-20 | 2013-01-22 | 미쓰비시 타나베 파마 코퍼레이션 | 신규한 말론산술폰아미드 유도체 및 그 의약 용도 |
| WO2008155378A1 (en) | 2007-06-21 | 2008-12-24 | Janssen Pharmaceutica Nv | Polymorphic and hydrate forms, salts and process for preparing 6-{difluoro[6-(1-methyl-1h-pyrazol-4-yl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}quinoline |
| EP2173338A1 (en) | 2007-07-06 | 2010-04-14 | OSI Pharmaceuticals, Inc. | Combination anti-cancer therapy |
| US7981903B2 (en) | 2007-08-08 | 2011-07-19 | Glaxosmithkline Llc | 2-[2-{phenylamino}-1H-pyrrolo[2,3-D]pyrimidin-4-yl)amino] benzamide derivatives as IGF-1R inhibitors for the treatment of cancer |
| WO2009019518A1 (en) | 2007-08-09 | 2009-02-12 | Astrazeneca Ab | Pyrimidine compounds having a fgfr inhibitory effect |
| WO2009021083A1 (en) | 2007-08-09 | 2009-02-12 | Smithkline Beecham Corporation | Quinoxaline derivatives as pi3 kinase inhibitors |
| US20090054304A1 (en) | 2007-08-23 | 2009-02-26 | Kalypsys, Inc. | Heterocyclic modulators of tgr5 for treatment of disease |
| JP5480813B2 (ja) | 2007-11-16 | 2014-04-23 | インサイト・コーポレイション | Ｊａｎｕｓキナーゼ阻害剤としての置換複素環 |
| WO2009137378A2 (en) | 2008-05-05 | 2009-11-12 | Schering Corporation | Sequential administration of chemotherapeutic agents for treatment of cancer |
| ES2554513T3 (es) | 2008-05-23 | 2015-12-21 | Novartis Ag | Derivados de quinolinas y quinoxalinas como inhibidores de la proteína tirosina quinasa |
| WO2010059771A1 (en) | 2008-11-20 | 2010-05-27 | Osi Pharmaceuticals, Inc. | Substituted pyrrolo[2,3-b]-pyridines and-pyrazines |
| US8716280B2 (en) | 2009-01-21 | 2014-05-06 | Basilea Pharmaceutica Ag | Bicyclic antibiotics |
| US20110288090A1 (en) | 2009-02-02 | 2011-11-24 | Armstrong Donna J | Inhibitors of AKT Activity |
| TW201041888A (en) | 2009-05-06 | 2010-12-01 | Plexxikon Inc | Compounds and methods for kinase modulation, and indications therefor |
| US20120277230A1 (en) | 2009-06-12 | 2012-11-01 | Societe Splicos | Compounds useful for treating cancer |
| ES2534226T3 (es) | 2009-09-03 | 2015-04-20 | Bioenergenix | Compuestos heterocíclicos para la inhibición de PASK |
| CA2772790C (en) | 2009-09-04 | 2017-06-27 | Benjamin Bader | Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors |
| US20110123545A1 (en) | 2009-11-24 | 2011-05-26 | Bristol-Myers Squibb Company | Combination of vegfr2 and igf1r inhibitors for the treatment of proliferative diseases |
| EP2332939A1 (en) | 2009-11-26 | 2011-06-15 | Æterna Zentaris GmbH | Novel Naphthyridine derivatives and the use thereof as kinase inhibitors |
| RU2639876C2 (ru) | 2010-03-30 | 2017-12-25 | Версеон Корпорейшн | Мультизамещенные ароматические соединения в качестве ингибиторов тромбина |
| GB201007286D0 (en) | 2010-04-30 | 2010-06-16 | Astex Therapeutics Ltd | New compounds |
| WO2011146591A1 (en) | 2010-05-19 | 2011-11-24 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| CN103153062B (zh) | 2010-05-24 | 2015-07-15 | 因特利凯有限责任公司 | 杂环化合物及其用途 |
| GB201020179D0 (en) | 2010-11-29 | 2011-01-12 | Astex Therapeutics Ltd | New compounds |
| CN102532141A (zh) | 2010-12-08 | 2012-07-04 | 中国科学院上海药物研究所 | [1，2，4]三唑并[4，3-b][1，2，4]三嗪类化合物、其制备方法和用途 |
| KR101928116B1 (ko) | 2011-01-31 | 2018-12-11 | 노파르티스 아게 | 신규 헤테로시클릭 유도체 |
| JP2014510265A (ja) | 2011-02-02 | 2014-04-24 | アムジェン インコーポレイテッド | Ｉｇｆ−１ｒの阻害に関する方法および組成物 |
| CN103491962B (zh) | 2011-02-23 | 2016-10-12 | 因特利凯有限责任公司 | 激酶抑制剂的组合及其用途 |
| WO2012118492A1 (en) | 2011-03-01 | 2012-09-07 | Array Biopharma Inc. | Heterocyclic sulfonamides as raf inhibitors |
| EP2702173A1 (en) | 2011-04-25 | 2014-03-05 | OSI Pharmaceuticals, LLC | Use of emt gene signatures in cancer drug discovery, diagnostics, and treatment |
| CN107245056A (zh) | 2011-08-26 | 2017-10-13 | 润新生物公司 | 化学实体、组合物及方法 |
| EP2755657B1 (en) | 2011-09-14 | 2017-11-29 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
| EP2757885B1 (en) | 2011-09-21 | 2017-03-15 | Neupharma, Inc. | Certain chemical entites, compositions, and methods |
| EP2763994A4 (en) | 2011-10-04 | 2015-08-26 | Gilead Calistoga Llc | NEW QUINOXALINE INHIBITORS OF THE PI3K PATH |
| GB201118652D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201118654D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201118656D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| JO3210B1 (ar) | 2011-10-28 | 2018-03-08 | Merck Sharp & Dohme | مثبط منصهر لبروتين نقل الكوليسترليستير اوكسازوليدينون ثمائي الحلقة |
| ES2587533T3 (es) | 2011-10-28 | 2016-10-25 | Novartis Ag | Derivados de purina y su uso en el tratamiento de enfermedades |
| GB201118675D0 (en) | 2011-10-28 | 2011-12-14 | Astex Therapeutics Ltd | New compounds |
| EA029140B1 (ru) | 2012-03-08 | 2018-02-28 | Астеллас Фарма Инк. | Новый слитый fgfr3 |
| GB201209613D0 (en) * | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
| GB201209609D0 (en) | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
| US20150203589A1 (en) | 2012-07-24 | 2015-07-23 | The Trustees Of Columbia University In The City Of New York | Fusion proteins and methods thereof |
| CA2898326C (en) | 2013-01-18 | 2022-05-17 | Foundation Medicine, Inc. | Methods of treating cholangiocarcinoma |
| GB201307577D0 (en) | 2013-04-26 | 2013-06-12 | Astex Therapeutics Ltd | New compounds |
| EP3027623A4 (en) | 2013-08-02 | 2017-03-01 | Ignyta, Inc. | METHODS OF TREATING VARIOUS CANCERS USING AN AXL/cMET INHIBITOR ALONE OR IN COMBINATION WITH OTHER AGENTS |
| US9221804B2 (en) | 2013-10-15 | 2015-12-29 | Janssen Pharmaceutica Nv | Secondary alcohol quinolinyl modulators of RORγt |
| KR102479696B1 (ko) | 2014-03-26 | 2022-12-22 | 아스텍스 테라퓨틱스 리미티드 | Fgfr 억제제 및 igf1r 억제제의 조합물 |
| PT3122358T (pt) | 2014-03-26 | 2021-03-04 | Astex Therapeutics Ltd | Combinações de inibidores do fgfr e cmet para o tratamento do cancro |
| JO3512B1 (ar) | 2014-03-26 | 2020-07-05 | Astex Therapeutics Ltd | مشتقات كينوكسالين مفيدة كمعدلات لإنزيم fgfr كيناز |
| JOP20200201A1 (ar) | 2015-02-10 | 2017-06-16 | Astex Therapeutics Ltd | تركيبات صيدلانية تشتمل على n-(3.5- ثنائي ميثوكسي فينيل)-n'-(1-ميثيل إيثيل)-n-[3-(ميثيل-1h-بيرازول-4-يل) كينوكسالين-6-يل]إيثان-1.2-ثنائي الأمين |
| CA2976638A1 (en) | 2015-02-19 | 2016-08-25 | Bioclin Therapeutics, Inc. | Methods, compositions, and kits for treatment of cancer |
| US10478494B2 (en) | 2015-04-03 | 2019-11-19 | Astex Therapeutics Ltd | FGFR/PD-1 combination therapy for the treatment of cancer |
-
2012
- 2012-05-30 GB GBGB1209613.7A patent/GB201209613D0/en not_active Ceased
-
2013
- 2013-05-30 EP EP13731850.7A patent/EP2855480B1/en active Active
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| CN104507944B (zh) | 2017-04-12 |
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| CA2874967A1 (en) | 2013-12-05 |
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| RU2014153050A (ru) | 2016-07-20 |
| DK2855480T3 (da) | 2019-07-22 |
| EP2855480A1 (en) | 2015-04-08 |
| JP6363068B2 (ja) | 2018-07-25 |
| WO2013179033A1 (en) | 2013-12-05 |
| AU2013269316A1 (en) | 2014-10-30 |
| HUE045663T2 (hu) | 2020-01-28 |
| KR20150016595A (ko) | 2015-02-12 |
| HRP20191202T1 (hr) | 2019-10-18 |
| BR112014029709B1 (pt) | 2022-03-22 |
| CN104507944A (zh) | 2015-04-08 |
| IN2014MN02069A (h) | 2015-08-21 |
| SI2855480T1 (sl) | 2019-09-30 |
| JP2015518039A (ja) | 2015-06-25 |
| MX2014014110A (es) | 2015-06-17 |
| BR112014029709A2 (pt) | 2017-06-27 |
| AU2013269316C1 (en) | 2018-04-12 |
| ES2739348T3 (es) | 2020-01-30 |
| AU2013269316B2 (en) | 2017-10-19 |
| US20170000796A1 (en) | 2017-01-05 |
| RU2702906C2 (ru) | 2019-10-14 |
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