RU2702906C2 - Птеридины в качестве fgfr ингибиторов - Google Patents
Птеридины в качестве fgfr ингибиторов Download PDFInfo
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- RU2702906C2 RU2702906C2 RU2014153050A RU2014153050A RU2702906C2 RU 2702906 C2 RU2702906 C2 RU 2702906C2 RU 2014153050 A RU2014153050 A RU 2014153050A RU 2014153050 A RU2014153050 A RU 2014153050A RU 2702906 C2 RU2702906 C2 RU 2702906C2
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Classifications
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- 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
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- 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
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- 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (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 | |
| GBGB1209613.7A GB201209613D0 (en) | 2012-05-30 | 2012-05-30 | New compounds |
| US61/653,081 | 2012-05-30 | ||
| GB1209613.7 | 2012-05-30 | ||
| 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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| RU2014153050A RU2014153050A (ru) | 2016-07-20 |
| RU2702906C2 true RU2702906C2 (ru) | 2019-10-14 |
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| RU2014153050A RU2702906C2 (ru) | 2012-05-30 | 2013-05-30 | Птеридины в качестве fgfr ингибиторов |
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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 |
| 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 |
| GB201118675D0 (en) | 2011-10-28 | 2011-12-14 | Astex Therapeutics Ltd | New compounds |
| GB2504177B (en) | 2012-05-14 | 2014-12-10 | Thoratec Corp | Sheath system for catheter pump |
| 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 |
| HRP20210338T1 (hr) | 2014-03-26 | 2021-04-30 | Astex Therapeutics Ltd. | Kombinacije fgfr-i cmet-inhibitora za liječenje raka |
| CN106456648B (zh) | 2014-03-26 | 2021-11-02 | 阿斯特克斯治疗有限公司 | Fgfr抑制剂和igf1r抑制剂的组合 |
| 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 |
| AU2016328692B2 (en) * | 2015-09-23 | 2021-03-11 | Janssen Pharmaceutica Nv | New compounds |
| LT3353164T (lt) * | 2015-09-23 | 2022-01-25 | Janssen Pharmaceutica, N.V. | Diheteroarilpakeistieji 1,4-benzodiazepinai ir jų naudojimas vėžio gydymui |
| MX382526B (es) | 2015-10-23 | 2025-03-13 | Array Biopharma Inc | Compuestos de 2-piridazin-3(2h)-ona 2-aril sustituidas y 2-heteroaril sustituidas como inhibidores de las tirosina quinasas fgfr |
| PL3442947T3 (pl) * | 2016-04-15 | 2023-10-02 | Epizyme, Inc. | Związki arylowe lub heteroarylowe podstawione aminą jako inhibitory ehmt1 i ehmt2 |
| US11672800B2 (en) | 2017-04-21 | 2023-06-13 | Epizyme, Inc. | Combination therapies with EHMT2 inhibitors |
| JP6974618B2 (ja) * | 2017-12-07 | 2021-12-01 | ハルビン チェンバオ ファーマシューティカル カンパニー リミテッド | Ｆｇｆｒ及びｖｅｇｆｒ阻害剤としての化合物の塩形態、結晶形およびその製造方法 |
| 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 |
| EP3793464A4 (en) | 2018-05-18 | 2021-07-21 | Bard Access Systems, Inc. | CONNECTION SYSTEM AND METHOD FOR MAKING AN ELECTRICAL CONNECTION THROUGH A COVERING CLOTH |
| US12180207B2 (en) | 2018-12-19 | 2024-12-31 | Array Biopharma Inc. | Substituted pyrazolo[1,5-a]pyridine compounds as inhibitors of FGFR tyrosine kinases |
| EP3898615A1 (en) | 2018-12-19 | 2021-10-27 | Array Biopharma, Inc. | 7-((3,5-dimethoxyphenyl)amino)quinoxaline derivatives as fgfr inhibitors for treating cancer |
| 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 |
| WO2021011411A1 (en) | 2019-07-12 | 2021-01-21 | Bard Access Systems, Inc. | Catheter tracking and placement system including light emitting diode array |
| CN112336338A (zh) | 2019-08-08 | 2021-02-09 | 巴德阿克塞斯系统股份有限公司 | 包括光纤连接器模块的形状感测系统及其方法 |
| KR20220098759A (ko) | 2019-11-08 | 2022-07-12 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 키나제 억제제에 대해 내성을 획득한 암의 치료 방법 |
| US20230115945A1 (en) | 2019-12-30 | 2023-04-13 | Tyra Biosciences, Inc. | Aminopyrimidine compounds |
| WO2021138391A1 (en) | 2019-12-30 | 2021-07-08 | Tyra Biosciences, Inc. | Indazole 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 |
| US12264149B2 (en) | 2020-12-30 | 2025-04-01 | Tyra Biosciences, Inc. | Indazole compounds as kinase inhibitors |
| EP4297873A1 (en) | 2021-02-26 | 2024-01-03 | Tyra Biosciences, Inc. | Aminopyrimidine compounds and methods of their use |
| JP2025525434A (ja) | 2022-06-29 | 2025-08-05 | タイラ・バイオサイエンシーズ・インコーポレイテッド | 多形化合物及びその使用 |
| AU2023300362A1 (en) | 2022-06-29 | 2025-01-09 | Tyra Biosciences, Inc. | Indazole compounds |
| 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 |
| KR20250164828A (ko) | 2023-03-30 | 2025-11-25 | 레볼루션 메디슨즈, 인크. | Ras gtp 가수분해 유도를 위한 조성물 및 이의 용도 |
| AU2024265078A1 (en) | 2023-05-04 | 2025-12-11 | Revolution Medicines, Inc. | Combination therapy for a ras related disease or disorder |
| 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 |
| TW202535368A (zh) | 2023-12-15 | 2025-09-16 | 美商泰拉生物科學公司 | 吲唑化合物 |
| WO2025171296A1 (en) | 2024-02-09 | 2025-08-14 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025222097A1 (en) | 2024-04-19 | 2025-10-23 | Tyra Biosciences, Inc. | Indazole-based protac degraders and their anticancer activity |
| WO2025240847A1 (en) | 2024-05-17 | 2025-11-20 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025255438A1 (en) | 2024-06-07 | 2025-12-11 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001019825A1 (en) * | 1999-09-15 | 2001-03-22 | Warner-Lambert Company | Pteridinones as kinase inhibitors |
| RU2355687C2 (ru) * | 2003-08-01 | 2009-05-20 | Дженелэбс Текнолоджиз, Инк | Бициклические производные имидазола в качестве средства против вирусов семейства flaviviridae |
Family Cites Families (123)
| 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 |
| JPH09500615A (ja) | 1993-05-14 | 1997-01-21 | ジェネンテク，インコーポレイテッド | Ｒａｓ−ファルネシル転移酵素阻害剤 |
| 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 |
| WO1998004689A1 (en) | 1995-07-31 | 1998-02-05 | Urocor, Inc. | 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 |
| PL194670B1 (pl) | 1997-05-28 | 2007-06-29 | 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 |
| AU3033500A (en) | 1999-01-15 | 2000-08-01 | Agouron Pharmaceuticals, Inc. | Non-peptide glp-1 agonists |
| 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 |
| JP4286146B2 (ja) | 2001-12-18 | 2009-06-24 | メルク エンド カムパニー インコーポレーテッド | メタボトロピックグルタミン酸受容体−５のヘテロアリール置換ピラゾール系調節剤 |
| WO2003055491A1 (en) | 2001-12-24 | 2003-07-10 | Astrazeneca Ab | Substituted quinazoline derivatives as inhibitors of aurora kinases |
| 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 |
| WO2003086394A1 (en) | 2002-04-08 | 2003-10-23 | Merck & Co., Inc. | Inhibitors of akt activity |
| US7074534B2 (en) | 2002-07-10 | 2006-07-11 | E. I. Du Pont De Nemours And Company | Polymeric 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 |
| BR0315053A (pt) | 2002-10-03 | 2005-08-09 | Targegen Inc | Agentes vasculostáticos , composição, artigo e processo de preparação dos mesmos |
| 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 |
| CA2512646A1 (en) | 2003-01-17 | 2004-08-05 | Warner-Lambert Company Llc | 2-aminopyridine substituted heterocycles as inhibitors of cellular proliferation |
| WO2004098494A2 (en) | 2003-04-30 | 2004-11-18 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| CN102584813B (zh) | 2003-05-14 | 2016-07-06 | Ngc药物公司 | 化合物及其在调节淀粉样蛋白β中的用途 |
| ME00541B (me) | 2003-05-23 | 2011-10-10 | Zentaris Gmbh | NOVI PIRIDOPIRAZINI I NJlUHOVA UPOTREBA KAO MODULATORA KlNAZA |
| DE10323345A1 (de) | 2003-05-23 | 2004-12-16 | Zentaris Gmbh | Neue Pyridopyrazine und deren Verwendung als Kinase-Inhibitoren |
| WO2005007099A2 (en) | 2003-07-10 | 2005-01-27 | Imclone Systems Incorporated | Pkb inhibitors as anti-tumor agents |
| EP1646383A4 (en) | 2003-07-21 | 2009-03-25 | Bethesda Pharmaceuticals Inc | DESIGN AND SYNTHESIS OF OPTIMIZED LIGANDS FOR PPAR |
| JP2007508355A (ja) * | 2003-10-17 | 2007-04-05 | ４・アー・ゼット・アー・バイオサイエンス・ナムローゼ・フエンノートシャップ | 複素環−置換プテリジン誘導体と治療におけるその利用 |
| EP2762475A1 (en) | 2003-11-07 | 2014-08-06 | Novartis Vaccines and Diagnostics, Inc. | Pharmaceutically acceptable salts of quinolinone compounds and their medical use |
| AU2004295058B9 (en) | 2003-11-20 | 2011-06-30 | Janssen Pharmaceutica N.V. | 6-alkenyl and 6-phenylalkyl substituted 2-quinolinones and 2-quinoxalinones as poly(ADP-ribose) polymerase inhibitors |
| JP2007512275A (ja) | 2003-11-24 | 2007-05-17 | エフ．ホフマン−ラ ロシュ アーゲー | ピラゾリルおよびイミダゾリルピリミジン |
| KR101164258B1 (ko) | 2003-12-23 | 2012-07-11 | 아스텍스 테라퓨틱스 리미티드 | 단백질 키나아제 조절제로서의 피라졸 유도체 |
| US7205316B2 (en) | 2004-05-12 | 2007-04-17 | Abbott Laboratories | Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands |
| US7098222B2 (en) | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| US20090118261A1 (en) | 2004-08-31 | 2009-05-07 | Astrazeneca Ab | Quinazolinone derivatives and their use as b-raf inhibitors |
| CA2583192A1 (en) | 2004-10-14 | 2006-04-20 | F. Hoffmann-La Roche Ag | 1,5-naphthyridine azolidinones having cdk1 antiproliferative activity |
| SI1830869T1 (sl) | 2004-12-24 | 2013-12-31 | Spinifex Pharmaceuticals Pty Ltd | Postopek zdravljenja ali profilakse |
| 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 |
| WO2006124354A2 (en) | 2005-05-12 | 2006-11-23 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| EP1881981A1 (en) | 2005-05-18 | 2008-01-30 | Wyeth | 4, 6-diamino-[1,7] naphthyridine-3-carbonitrile inhibitors of tpl2 kinase and methods of making and using the same |
| GB0513692D0 (en) | 2005-07-04 | 2005-08-10 | Karobio Ab | Novel pharmaceutical compositions |
| AU2006283846B2 (en) | 2005-08-26 | 2012-04-05 | Merck Serono Sa | Pyrazine derivatives and use as PI3K inhibitors |
| US8217042B2 (en) | 2005-11-11 | 2012-07-10 | Zentaris Gmbh | Pyridopyrazines and their use as modulators of kinases |
| CA2628039A1 (en) | 2005-11-11 | 2007-05-18 | Aeterna Zentaris Gmbh | Novel pyridopyrazines and their use as modulators of kinases |
| EP1790342A1 (de) | 2005-11-11 | 2007-05-30 | Zentaris GmbH | Pyridopyrazin-Derivate und deren Verwendung als Modulatoren der Signaltransduktionswege |
| KR101412675B1 (ko) | 2005-12-21 | 2014-07-03 | 얀센 파마슈티카 엔.브이. | 티로신 키나제 모듈레이터로서의 트리아졸로피리다진 |
| 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 |
| CA2653117A1 (en) | 2006-05-24 | 2007-11-29 | Boehringer Ingelheim International Gmbh | Substituted pteridines substituted with a four-membered heterocycle |
| AU2007271187A1 (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 |
| JP2010513278A (ja) | 2006-12-13 | 2010-04-30 | シェーリング コーポレイション | Ｉｇｆ１ｒインヒビターを用いた癌の処置方法 |
| RU2009122670A (ru) | 2006-12-21 | 2011-01-27 | Плекссикон, Инк. (Us) | Соединения и способы для модуляции киназ и показания к их применению |
| CA2673003A1 (en) | 2006-12-22 | 2008-07-03 | Novartis Ag | Quinazolines for pdk1 inhibition |
| HRP20150642T1 (hr) | 2006-12-22 | 2015-08-14 | Astex Therapeutics Limited | BICIKLIÄŚKE HETEROCIKLIÄŚKE TVARI KAO INHIBITORI FGFR-a |
| KR20080062876A (ko) | 2006-12-29 | 2008-07-03 | 주식회사 대웅제약 | 신규한 항진균성 트리아졸 유도체 |
| EP1990342A1 (en) | 2007-05-10 | 2008-11-12 | AEterna Zentaris GmbH | Pyridopyrazine Derivatives, Process of Manufacturing and Uses thereof |
| PE20090288A1 (es) | 2007-05-10 | 2009-04-03 | Smithkline Beecham Corp | Derivados de quinoxalina como inhibidores de la pi3 quinasa |
| WO2008150827A1 (en) | 2007-05-29 | 2008-12-11 | Smithkline Beecham Corporation | Naphthyridine, derivatives as p13 kinase inhibitors |
| 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 |
| AU2008264458B2 (en) | 2007-06-20 | 2013-01-24 | Mitsubishi Tanabe Pharma Corporation | Novel malonic acid sulfonamide derivative and pharmaceutical use thereof |
| EP2170894A1 (en) | 2007-06-21 | 2010-04-07 | Janssen Pharmaceutica N.V. | 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 |
| WO2009020990A1 (en) | 2007-08-08 | 2009-02-12 | Smithkline Beecham Corporation | 2- [ (2-{phenylamino}-1h-pyrrolo [2, 3-d] pyrimidin-4-yl) amino] benzamide derivatives as igf-1r inhibitors for the treatment of cancer |
| WO2009021083A1 (en) | 2007-08-09 | 2009-02-12 | Smithkline Beecham Corporation | Quinoxaline derivatives as pi3 kinase inhibitors |
| WO2009019518A1 (en) | 2007-08-09 | 2009-02-12 | Astrazeneca Ab | Pyrimidine compounds having a fgfr inhibitory effect |
| US20090054304A1 (en) | 2007-08-23 | 2009-02-26 | Kalypsys, Inc. | Heterocyclic modulators of tgr5 for treatment of disease |
| US8309718B2 (en) | 2007-11-16 | 2012-11-13 | Incyte Corporation | 4-pyrazolyl-N-arylpyrimidin-2-amines and 4-pyrazolyl-N-heteroarylpyrimidin-2-amines as janus kinase inhibitors |
| MX2010012064A (es) | 2008-05-05 | 2010-12-06 | Schering Corp | Uso secuencial de agentes quimioterapeuticos citotoxicos para el tratamiento de cancer. |
| EA021421B1 (ru) | 2008-05-23 | 2015-06-30 | Новартис Аг | Производные хинолинов и хиноксалинов в качестве ингибиторов протеинтирозинкиназы, способ их получения, содержащая их фармацевтическая композиция и способ лечения заболеваний с применением таких соединений |
| 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 |
| JP2012516847A (ja) | 2009-02-02 | 2012-07-26 | メルク・シャープ・エンド・ドーム・コーポレイション | Ａｋｔ活性の阻害剤 |
| TW201041888A (en) | 2009-05-06 | 2010-12-01 | Plexxikon Inc | Compounds and methods for kinase modulation, and indications therefor |
| CA2764026C (en) | 2009-06-12 | 2019-10-29 | Splicos | Compounds useful for treating aids |
| JP5696856B2 (ja) | 2009-09-03 | 2015-04-08 | バイオエナジェニックス | Ｐａｓｋの阻害用複素環式化合物 |
| WO2011026579A1 (en) | 2009-09-04 | 2011-03-10 | Bayer Schering Pharma Aktiengesellschaft | 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 |
| AU2011238616B2 (en) | 2010-03-30 | 2016-08-04 | Verseon Corporation | Multisubstituted aromatic compounds as inhibitors of thrombin |
| 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 |
| CA2804304C (en) | 2010-05-24 | 2020-02-25 | Intellikine, Llc | Heterocyclic compounds and uses thereof |
| 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 |
| US8987257B2 (en) | 2011-01-31 | 2015-03-24 | Novartis Ag | Heterocyclic derivatives |
| WO2012106556A2 (en) | 2011-02-02 | 2012-08-09 | Amgen Inc. | Methods and compositons relating to inhibition of igf-1r |
| CN106619647A (zh) | 2011-02-23 | 2017-05-10 | 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 |
| CA2846574C (en) | 2011-08-26 | 2020-07-07 | Neupharma, Inc. | Quinoxaline sulfonamide derivates for use as kinase inhibitors |
| EP3332785B1 (en) | 2011-09-14 | 2020-05-06 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
| EP2757885B1 (en) | 2011-09-21 | 2017-03-15 | Neupharma, Inc. | Certain chemical entites, compositions, and methods |
| WO2013052699A2 (en) | 2011-10-04 | 2013-04-11 | Gilead Calistoga Llc | Novel quinoxaline inhibitors of pi3k |
| GB201118675D0 (en) | 2011-10-28 | 2011-12-14 | Astex Therapeutics Ltd | New compounds |
| US9334271B2 (en) | 2011-10-28 | 2016-05-10 | Novarits Ag | Purine derivatives and their use in the treatment of disease |
| 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 |
| GB201118654D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201118652D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| JP6107812B2 (ja) | 2012-03-08 | 2017-04-05 | アステラス製薬株式会社 | 新規ｆｇｆｒ３融合体 |
| GB201209609D0 (en) | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
| GB201209613D0 (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 |
| US10980804B2 (en) | 2013-01-18 | 2021-04-20 | Foundation Medicine, Inc. | Methods of treating cholangiocarcinoma |
| GB201307577D0 (en) | 2013-04-26 | 2013-06-12 | Astex Therapeutics Ltd | New compounds |
| JP2016527274A (ja) | 2013-08-02 | 2016-09-08 | イグナイタ インコーポレイテッド | ＡＸＬ／ｃＭＥＴ阻害剤を単独または他の薬剤と組み合わせて用いて各種がんを治療する方法 |
| US9221804B2 (en) | 2013-10-15 | 2015-12-29 | Janssen Pharmaceutica Nv | Secondary alcohol quinolinyl modulators of RORγt |
| HRP20210338T1 (hr) | 2014-03-26 | 2021-04-30 | Astex Therapeutics Ltd. | Kombinacije fgfr-i cmet-inhibitora za liječenje raka |
| CN106456648B (zh) | 2014-03-26 | 2021-11-02 | 阿斯特克斯治疗有限公司 | Fgfr抑制剂和igf1r抑制剂的组合 |
| 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 |
| EP3258966A4 (en) | 2015-02-19 | 2018-07-25 | 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 |
-
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001019825A1 (en) * | 1999-09-15 | 2001-03-22 | Warner-Lambert Company | Pteridinones as kinase inhibitors |
| RU2355687C2 (ru) * | 2003-08-01 | 2009-05-20 | Дженелэбс Текнолоджиз, Инк | Бициклические производные имидазола в качестве средства против вирусов семейства flaviviridae |
Non-Patent Citations (3)
| Title |
|---|
| Garuti L. et al. Irreversible Protein Kinase Inhibitors Current medicinal chemistry, 01.07.2011, Vol:18, Nr:20, Page(s): 2981-2994. * |
| Garuti L. et al. Irreversible Protein Kinase Inhibitors Current medicinal chemistry, 01.07.2011, Vol:18, Nr:20, Page(s): 2981-2994. Zhou W. et al. A Structure-Guided Approach to Creating Covalent FGFR Inhibitors, CHEMISTRY AND BIOLOGY, 26.03.2010, Vol:17, Nr:3, Page(s): 285-295. * |
| Zhou W. et al. A Structure-Guided Approach to Creating Covalent FGFR Inhibitors, CHEMISTRY AND BIOLOGY, 26.03.2010, Vol:17, Nr:3, Page(s): 285-295. * |
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| KR102149759B1 (ko) | 2020-08-31 |
| KR20150016595A (ko) | 2015-02-12 |
| HUE045663T2 (hu) | 2020-01-28 |
| AU2013269316C1 (en) | 2018-04-12 |
| SI2855480T1 (sl) | 2019-09-30 |
| IN2014MN02069A (cg-RX-API-DMAC7.html) | 2015-08-21 |
| EP2855480B1 (en) | 2019-06-26 |
| BR112014029709A2 (pt) | 2017-06-27 |
| MX359418B (es) | 2018-09-27 |
| CN104507944B (zh) | 2017-04-12 |
| RU2014153050A (ru) | 2016-07-20 |
| CA2874967C (en) | 2021-11-09 |
| BR112014029709B1 (pt) | 2022-03-22 |
| JP6363068B2 (ja) | 2018-07-25 |
| US9447098B2 (en) | 2016-09-20 |
| AU2013269316A1 (en) | 2014-10-30 |
| AU2013269316B2 (en) | 2017-10-19 |
| JP2015518039A (ja) | 2015-06-25 |
| GB201209613D0 (en) | 2012-07-11 |
| MX2014014110A (es) | 2015-06-17 |
| US20170000796A1 (en) | 2017-01-05 |
| DK2855480T3 (da) | 2019-07-22 |
| ES2739348T3 (es) | 2020-01-30 |
| EP2855480A1 (en) | 2015-04-08 |
| CA2874967A1 (en) | 2013-12-05 |
| US20150291589A1 (en) | 2015-10-15 |
| WO2013179033A1 (en) | 2013-12-05 |
| HRP20191202T1 (hr) | 2019-10-18 |
| US10272087B2 (en) | 2019-04-30 |
| CN104507944A (zh) | 2015-04-08 |
| LT2855480T (lt) | 2019-08-12 |
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