KR102427777B1 - 디안하이드로갈락티톨, 디아세틸디안하이드로갈락티톨, 디브로모둘시톨, 또는 그의 유사체 또는 유도체를 이용하여 유전학적 다형성이 있는 환자에 있어서 티로신-키나아제-억제제 내성 악성종양, ahi1 조절곤란 또는 돌연변이를 치료하는 방법 - Google Patents
디안하이드로갈락티톨, 디아세틸디안하이드로갈락티톨, 디브로모둘시톨, 또는 그의 유사체 또는 유도체를 이용하여 유전학적 다형성이 있는 환자에 있어서 티로신-키나아제-억제제 내성 악성종양, ahi1 조절곤란 또는 돌연변이를 치료하는 방법 Download PDFInfo
- Publication number
- KR102427777B1 KR102427777B1 KR1020217036438A KR20217036438A KR102427777B1 KR 102427777 B1 KR102427777 B1 KR 102427777B1 KR 1020217036438 A KR1020217036438 A KR 1020217036438A KR 20217036438 A KR20217036438 A KR 20217036438A KR 102427777 B1 KR102427777 B1 KR 102427777B1
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- KR
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- Prior art keywords
- phenyl
- pyrimidin
- tki
- methyl
- pyridin
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| PCT/US2013/047320 WO2014004376A2 (en) | 2012-06-26 | 2013-06-24 | Methods for treating tyrosine-kinase-inhibitor-resistant malignancies in patients with genetic polymorphisms or ahi1 dysregulations or mutations employing dianhydrogalactitol, diacetyldianhydrogalactitol, dibromodulcitol, or analogs or derivatives thereof |
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| WO2014179528A2 (en) * | 2013-05-01 | 2014-11-06 | Brown Dennis M | Compositions and methods to improve the therapeutic benefit of suboptimally administered chemical compounds including substituted naphthalimides such as amonafide for the treatment of immunological, metabolic, infectious, and benign or neoplastic hyperproliferative disease conditions |
| CA2935077C (en) * | 2013-12-27 | 2022-03-15 | Geoffrey C. Winters | Sulfonamide-containing linkage systems for drug conjugates |
| AU2014373640B2 (en) | 2013-12-27 | 2018-08-30 | Var2 Pharmaceuticals Aps | VAR2CSA-drug conjugates |
| JP2017509336A (ja) | 2014-03-20 | 2017-04-06 | ファーマサイクリックス エルエルシー | ホスホリパーゼcガンマ2及び耐性に関連した変異 |
| SG11201608303QA (en) * | 2014-04-04 | 2016-11-29 | Del Mar Pharmaceuticals | Use of dianhydrogalactitol and analogs or derivatives thereof to treat non-small-cell carcinoma of the lung and ovarian cancer |
| EP3177366A4 (en) * | 2014-08-08 | 2018-04-04 | Pharmacyclics LLC | Bruton's tyrosine kinase inhibitor combinations and uses thereof |
| CA2960899C (en) | 2014-09-17 | 2021-08-17 | Zymeworks Inc. | Cytotoxic and anti-mitotic compounds, and methods of using the same |
| CN108024987A (zh) * | 2014-10-10 | 2018-05-11 | 德玛医药 | 用于治疗癌症的二去水卫矛醇的类似物或衍生物与含铂抗肿瘤药物的组合 |
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| EP3328839A1 (en) * | 2015-07-30 | 2018-06-06 | Bristol-Myers Squibb Company | Aryl substituted bicyclic heteroaryl compounds |
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| US11446274B2 (en) | 2015-10-28 | 2022-09-20 | Del Mar Pharmaceuticals (Bc) Ltd. | Use of dianhydrogalactitol or derivatives or analogs thereof for treatment of pediatric central nervous system malignancies |
| CN105476996B (zh) * | 2015-12-21 | 2017-12-26 | 神威药业集团有限公司 | 姜黄素与阿法替尼联合治疗非小细胞肺癌的用途 |
| CN105663028B (zh) * | 2016-02-23 | 2018-10-30 | 广西梧州制药(集团)股份有限公司 | 一种含去水卫矛醇的经直肠给药双层缓释栓剂 |
| CN105663075B (zh) * | 2016-02-23 | 2018-09-14 | 广西梧州制药(集团)股份有限公司 | 一种二溴卫矛醇肠溶片及其制备方法 |
| US10517958B2 (en) | 2016-10-04 | 2019-12-31 | Zymeworks Inc. | Compositions and methods for the treatment of platinum-drug resistant cancer |
| EP4357463A3 (en) * | 2016-12-01 | 2024-07-17 | Oxford BioDynamics PLC | Application of epigenetic chromsomal interactions in cancer diagnostics |
| EP3549608A4 (en) | 2016-12-01 | 2020-08-12 | Jiangsu Hengrui Medicine Co., Ltd. | USE OF A COMBINATION OF A VEGFR INHIBITOR AND PARP INHIBITOR IN THE MANUFACTURING OF A MEDICINAL PRODUCT FOR TREATMENT OF STOMACH CANCER |
| BR112019018687A2 (pt) | 2017-03-10 | 2020-04-07 | Athenex, Inc. | métodos de tratamento e/ou prevenção da ceratose actínica |
| US20200031920A1 (en) * | 2017-04-04 | 2020-01-30 | The George Washington University | Combination Therapy for Treating Cancer |
| JP2021505548A (ja) | 2017-12-06 | 2021-02-18 | 江蘇恒瑞医薬股▲ふん▼有限公司 | 化学療法抵抗性の卵巣がんまたは乳がんの治療におけるparp阻害剤の使用 |
| KR20190106315A (ko) * | 2018-03-08 | 2019-09-18 | 고려대학교 산학협력단 | 비소세포폐암의 표피성장인자 수용체 표적 항암제에 대한 민감성 증진용 조성물 |
| KR20200143376A (ko) | 2018-03-13 | 2020-12-23 | 샤이어 휴먼 지네틱 테라피즈 인크. | 혈장 칼리크레인 억제제로서의 치환된 이미다조피리딘 및 이의 용도 |
| CN108653293B (zh) * | 2018-05-29 | 2020-08-11 | 复旦大学 | Jak2抑制剂在预防和治疗印戒细胞癌中的应用 |
| US20230093099A1 (en) * | 2019-04-02 | 2023-03-23 | Cullgen (Shanghai), Inc. | Compounds and methods of treating cancers |
| US12371421B2 (en) | 2019-04-29 | 2025-07-29 | Ribon Therapeutics, Inc. | Solid forms of a PARP7 inhibitor |
| CN114667289B (zh) | 2019-09-18 | 2025-08-26 | 武田药品工业有限公司 | 杂芳基血浆激肽释放酶抑制剂 |
| US11787796B2 (en) | 2019-09-18 | 2023-10-17 | Takeda Pharmaceutical Company Limited | Plasma Kallikrein inhibitors and uses thereof |
| CA3160091A1 (en) | 2019-11-05 | 2021-05-14 | Abbvie Inc. | Dosing regimens for use in treating myelofibrosis and mpn-related disorders with navitoclax |
| CN111863159B (zh) * | 2020-06-01 | 2022-02-25 | 中山大学孙逸仙纪念医院 | 一种肿瘤免疫治疗疗效预测的列线图模型的建立方法 |
| GB202013466D0 (en) * | 2020-08-27 | 2020-10-14 | Inst De Medicina Molecular Joaeo Lobo Antunes | Genetic construct |
| AU2022205940A1 (en) * | 2021-01-06 | 2023-07-20 | Inaya Therapeutics, Inc. | Inhalable imatinib formulation |
| JP2024510504A (ja) * | 2021-03-17 | 2024-03-07 | 武田薬品工業株式会社 | 血漿カリクレインの多環式インヒビター |
| CN115745975B (zh) * | 2022-09-15 | 2023-11-24 | 中国药科大学 | 一种jak激酶结构域和假激酶结构域共抑制前药、制备方法及医药用途 |
| AU2024238830A1 (en) * | 2023-03-17 | 2025-10-23 | Cenovari Therapeutics, Inc. | Methods of use and compositions of bisbenzylisoquinolines for the treatment of malignancies |
| CN116987362B (zh) * | 2023-09-27 | 2023-12-05 | 常州宏巨电子科技有限公司 | 一种苯并噁嗪树脂基石墨烯薄膜材料及其制备方法和应用 |
| CN117405894B (zh) * | 2023-11-03 | 2025-02-18 | 华中科技大学同济医学院附属协和医院 | 蛋白激酶ck2在预测kras突变肺癌免疫治疗疗效中的新应用 |
Family Cites Families (222)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59186924A (ja) | 1983-04-08 | 1984-10-23 | Kureha Chem Ind Co Ltd | ヒト免疫グロブリン結合抗腫瘍剤 |
| US5542935A (en) | 1989-12-22 | 1996-08-06 | Imarx Pharmaceutical Corp. | Therapeutic delivery systems related applications |
| US5395855A (en) | 1990-05-07 | 1995-03-07 | Ciba-Geigy Corporation | Hydrazones |
| US5484612A (en) | 1993-09-22 | 1996-01-16 | The Board Of Trustees Of The Leland Stanford Junior University | Method of treating a mammal having a solid tumor susceptible to treatment with cisplatin |
| US6011069A (en) | 1995-12-26 | 2000-01-04 | Nisshin Flour Milling Co., Ltd. | Multidrug resistance inhibitors |
| US20020077461A1 (en) | 1996-04-24 | 2002-06-20 | Soren Bjorn | Pharmaceutical formulation |
| EP0923941B1 (en) | 1996-06-27 | 2006-05-17 | Chugai Seiyaku Kabushiki Kaisha | Remedies for myeloma to be used together with nitrogen mustard antitumor agents |
| US6121245A (en) | 1997-01-29 | 2000-09-19 | Firshein; Richard N. | Method of treating cancer using alkylglycerols in conjunction with chemotherapy |
| CO4950519A1 (es) | 1997-02-13 | 2000-09-01 | Novartis Ag | Ftalazinas, preparaciones farmaceuticas que las comprenden y proceso para su preparacion |
| US20040072889A1 (en) | 1997-04-21 | 2004-04-15 | Pharmacia Corporation | Method of using a COX-2 inhibitor and an alkylating-type antineoplastic agent as a combination therapy in the treatment of neoplasia |
| CA2294247C (en) | 1997-07-01 | 2004-10-26 | Atherogenics, Inc. | Antioxidant enhancement of therapy for hyperproliferative conditions |
| GB9721069D0 (en) | 1997-10-03 | 1997-12-03 | Pharmacia & Upjohn Spa | Polymeric derivatives of camptothecin |
| US6100254A (en) | 1997-10-10 | 2000-08-08 | Board Of Regents, The University Of Texas System | Inhibitors of protein tyrosine kinases |
| AU4543899A (en) | 1998-06-08 | 1999-12-30 | Advanced Medicine, Inc. | Multibinding inhibitors of microsomal triglyceride transferase protein |
| PT1104297E (pt) | 1998-07-09 | 2006-05-31 | Cephalon Inc | Composicoes para o tratamento da leucemia linfocitica cronica |
| BR9912938B1 (pt) | 1998-08-11 | 2011-06-28 | derivados de isoquinolina, composição que os compreende, processo para preparação e uso dos mesmos. | |
| US6326390B1 (en) | 1998-08-25 | 2001-12-04 | King Pharmaceuticals Reseach And Development, Inc. | Use of adenosine A3 receptor antagonists to inhibit tumor growth |
| EP1165085B1 (en) | 1999-03-30 | 2006-06-14 | Novartis AG | Phthalazine derivatives for treating inflammatory diseases |
| WO2008109417A1 (en) | 2007-03-02 | 2008-09-12 | Case Western Reserve University | Mgmt inhibitor combinations for the treatment of neoplastic disorders |
| US7811981B2 (en) | 1999-08-30 | 2010-10-12 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Methods of and compositions for inhibiting the proliferation of mammalian cells |
| AR030557A1 (es) | 2000-04-14 | 2003-08-27 | Jagotec Ag | Una tableta en multicapa de liberacion controlada y metodo de tratamiento |
| US6921722B2 (en) | 2000-05-30 | 2005-07-26 | Ebara Corporation | Coating, modification and etching of substrate surface with particle beam irradiation of the same |
| US20030072794A1 (en) | 2000-06-09 | 2003-04-17 | Teni Boulikas | Encapsulation of plasmid DNA (lipogenes™) and therapeutic agents with nuclear localization signal/fusogenic peptide conjugates into targeted liposome complexes |
| US6613736B2 (en) | 2000-06-16 | 2003-09-02 | Thomas T. Aoki | System and method for treating eye and nerve diseases in diabetic and non-diabetic patients |
| DE60141963D1 (de) | 2000-06-23 | 2010-06-10 | Mitsubishi Tanabe Pharma Corp | Antitumoreffekt-verstärker |
| US7473691B2 (en) | 2000-09-15 | 2009-01-06 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6610677B2 (en) | 2000-09-15 | 2003-08-26 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| WO2002022605A1 (en) | 2000-09-15 | 2002-03-21 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6660731B2 (en) | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| CN1116875C (zh) | 2000-10-19 | 2003-08-06 | 南京振中生物工程有限公司 | 紫杉醇脂质组合物及其制备方法 |
| US6503914B1 (en) | 2000-10-23 | 2003-01-07 | Board Of Regents, The University Of Texas System | Thienopyrimidine-based inhibitors of the Src family |
| US6733783B2 (en) | 2000-10-30 | 2004-05-11 | Euro-Celtique S.A. | Controlled release hydrocodone formulations |
| US7619005B2 (en) | 2000-11-01 | 2009-11-17 | Cognition Pharmaceuticals Llc | Methods for treating cognitive impairment in humans with Multiple Sclerosis |
| US20020155565A1 (en) | 2000-11-10 | 2002-10-24 | Pilar Garin-Chesa | FAP-activated anti-tumor compounds |
| AP2003002825A0 (en) | 2000-12-21 | 2003-09-30 | Vertex Pharma | Pyrazole compounds useful as protein kinase inhibitors |
| US20100098691A1 (en) | 2001-01-24 | 2010-04-22 | S'bio Pte Ltd | Combination of benzimidazole anti-cancer agent and a second anti-cancer agent |
| US7318931B2 (en) | 2001-06-21 | 2008-01-15 | Genentech, Inc. | Sustained release formulation |
| US7005445B2 (en) | 2001-10-22 | 2006-02-28 | The Research Foundation Of State University Of New York | Protein kinase and phosphatase inhibitors and methods for designing them |
| US20030158118A1 (en) | 2001-11-26 | 2003-08-21 | Weidner Morten Sloth | Combination of cimetidine and cysteine derivatives for treating cancer |
| UA76810C2 (uk) | 2001-12-10 | 2006-09-15 | Мерк Енд Ко., Інк. | Фармацевтична композиція антагоніста рецептора тахікініну у формі наночастинок |
| US7045534B2 (en) | 2002-02-12 | 2006-05-16 | The Board Of Trustees Of The Leland Stanford Junior University | Methods of reducing angiogenesis |
| WO2003070823A2 (en) | 2002-02-20 | 2003-08-28 | The General Hospital Corporation | Conjugates comprising a biodegradable polymer and uses therefor |
| US7101576B2 (en) | 2002-04-12 | 2006-09-05 | Elan Pharma International Limited | Nanoparticulate megestrol formulations |
| WO2004037814A1 (en) | 2002-10-25 | 2004-05-06 | Vertex Pharmaceuticals Incorporated | Indazolinone compositions useful as kinase inhibitors |
| US7112676B2 (en) | 2002-11-04 | 2006-09-26 | Hoffmann-La Roche Inc. | Pyrimido compounds having antiproliferative activity |
| TW200413381A (en) | 2002-11-04 | 2004-08-01 | Hoffmann La Roche | Novel amino-substituted dihydropyrimido [4,5-d]pyrimidinone derivatives, their manufacture and use as pharmaceutical agents |
| EP1560931B1 (en) | 2002-11-14 | 2011-07-27 | Dharmacon, Inc. | Functional and hyperfunctional sirna |
| CL2003002287A1 (es) | 2002-11-25 | 2005-01-14 | Wyeth Corp | COMPUESTOS DERIVADOS DE TIENO[3,2-b]-PIRIDINA-6-CARBONITRILOS Y TIENEO[2,3-b]-PIRIDINA-5-CARBONITRILOS, COMPOSICION FARMACEUTICA, PROCEDIMIENTO DE PREPARACION Y COMPUESTOS INTERMEDIARIOS, Y SU USO EN EL TRATAMIENTO DEL CANCER, APOPLEJIA, OSTEOPOROSIS |
| US7276519B2 (en) | 2002-11-25 | 2007-10-02 | Wyeth | Thieno[3,2-b]pyridine-6-carbonitriles and thieno[2,3-b]pyridine-5-carbonitriles as protein kinase inhibitors |
| WO2004060313A2 (en) | 2002-12-30 | 2004-07-22 | Celgene Corporation | Fluoroalkoxy-substituted 1, 3-dihydro-isoindolyl compounds and their pharmaceutical uses |
| ES2502490T3 (es) | 2003-02-26 | 2014-10-03 | Sugen, Inc. | Compuestos aminoheteroarílicos como inhibidores de proteín quinasas |
| US20070207952A1 (en) | 2003-03-24 | 2007-09-06 | Sequoia Pharmaceuticals | Long Acting Biologically Active Conjugates |
| TW200502236A (en) | 2003-03-28 | 2005-01-16 | Hoffmann La Roche | Novel pyrido[2,3-d]pyrimidin-7-carboxylic acid derivatives, their manufacture and use as pharmaceutical agents |
| US7220706B1 (en) | 2003-05-14 | 2007-05-22 | Praxair S.T. Technology, Inc. | Enhanced melt-textured growth |
| WO2004103958A2 (en) | 2003-05-19 | 2004-12-02 | Michigan State University | Preparation of hymenialdisine derivatives and use thereof |
| US7842835B2 (en) | 2003-07-07 | 2010-11-30 | Georgetown University | Histone deacetylase inhibitors and methods of use thereof |
| US20050009891A1 (en) | 2003-07-09 | 2005-01-13 | Lee Francis Y. | Combination of SRC Kinase inhibitors and chemotherapeutic agents for the treatment of proliferative diseases |
| TW200514776A (en) | 2003-08-06 | 2005-05-01 | Vertex Pharma | Aminotriazole compounds useful as inhibitors of protein kinases |
| MXPA06001483A (es) | 2003-08-07 | 2006-05-15 | Schering Corp | Inhibidores novedosos de la proteina farnesil transferasa como agentes antitumorales. |
| MXPA06003758A (es) | 2003-10-02 | 2006-08-11 | Cephalon Inc | Derivados de indol substituido. |
| HUP0303313A2 (hu) | 2003-10-09 | 2005-07-28 | Richter Gedeon Vegyészeti Gyár Rt. | Transzdermális gyógyszerkészítmények |
| US7169781B2 (en) | 2003-10-17 | 2007-01-30 | Hoffmann-La Roche Inc. | Imidazole derivatives and their use as pharmaceutical agents |
| SG146681A1 (en) | 2003-11-06 | 2008-10-30 | Wyeth Corp | 4-anilino-3-quinolinecarbonitriles for the treatment of chronic myelogenous leukemia (cml) |
| US7491725B2 (en) | 2004-02-06 | 2009-02-17 | Bristol-Myers Squibb Company | Process for preparing 2-aminothiazole-5-aromatic carboxamides as kinase inhibitors |
| EP1719771A1 (en) | 2004-02-19 | 2006-11-08 | Takeda Pharmaceutical Company Limited | Pyrazoloquinolone derivative and use thereof |
| RU2006136082A (ru) | 2004-03-15 | 2008-04-27 | Ф.Хоффманн-Ля Рош Аг (Ch) | Новые производныедихлорфенилпиридо[2,3]пиримидина, их получение и применение в качестве фармацевтических агентов |
| WO2005092326A1 (en) | 2004-03-22 | 2005-10-06 | The Regents Of The University Of Michigan | Small molecule antagonists of xiap family proteins |
| US7754897B2 (en) | 2005-06-15 | 2010-07-13 | Cardiome Pharma Corp. | Synthetic processes for the preparation of aminocyclohexyl ether compounds |
| AU2005230682B2 (en) | 2004-04-05 | 2010-10-21 | Merck Hdac Research, Llc | Histone deacetylase inhibitor prodrugs |
| TW200538149A (en) | 2004-05-20 | 2005-12-01 | Telik Inc | Sensitization to another anticancer therapy and/or amelioration of a side effect of another anticancer therapy by treatment with a GST-activated anticancer compound |
| TW200600091A (en) | 2004-05-21 | 2006-01-01 | Telik Inc | Sulfonylethyl phosphorodiamidates |
| ATE456579T1 (de) | 2004-07-20 | 2010-02-15 | Genentech Inc | Angiopoietin-like 4 protein hemmer kombinationen und deren verwendung |
| SE0402025D0 (sv) | 2004-08-13 | 2004-08-13 | Active Biotech Ab | Treatment of hyperproliferative disease with superantigens in combination with another anticancer agent |
| US7479561B2 (en) | 2004-08-16 | 2009-01-20 | Wyeth | 4-(2,4-dichloro-5-methoxyphenyl)amino-6-methoxy-7-{[5-substituted-amino)methyl]-3-furyl}-3-quinolinecarbonitriles as kinase inhibitors |
| CA2576924A1 (en) | 2004-08-31 | 2006-03-09 | F. Hoffmann-La Roche Ag | Amide derivatives of 7-amino-3-phenyl-dihydropyrimido [4,5-d]pyrimidinones, their manufacture and use as pharmaceutical agents |
| US20060100226A1 (en) | 2004-09-10 | 2006-05-11 | Sikorski James A | 2-Thiopyrimidinones as therapeutic agents |
| JP2008518883A (ja) | 2004-09-21 | 2008-06-05 | エフ.ホフマン−ラ ロシュ アーゲー | タンパク質キナーゼ阻害剤として有用な6−(2−アルキル−フェニル)−ピリド[2,3−d]ピリミジン |
| US7355677B2 (en) | 2004-12-09 | 2008-04-08 | Asml Netherlands B.V. | System and method for an improved illumination system in a lithographic apparatus |
| AR054416A1 (es) | 2004-12-22 | 2007-06-27 | Incyte Corp | Pirrolo [2,3-b]piridin-4-il-aminas y pirrolo [2,3-b]pirimidin-4-il-aminas como inhibidores de las quinasas janus. composiciones farmaceuticas. |
| WO2006066914A2 (en) | 2004-12-23 | 2006-06-29 | F. Hoffmann-La Roche Ag | Carbamate substituted imidazo- and pyrrolo-pyridines as protein kinase inhibitors |
| EP1833829A2 (en) | 2004-12-23 | 2007-09-19 | F. Hoffmann-Roche AG | Benzamide substituted imidazo- and pyrrolo-pyridines as protein kinase inhibitors |
| US7968574B2 (en) | 2004-12-28 | 2011-06-28 | Kinex Pharmaceuticals, Llc | Biaryl compositions and methods for modulating a kinase cascade |
| US7884094B2 (en) | 2005-02-17 | 2011-02-08 | Synta Pharmaceuticals Corp. | Compounds for the treatment of proliferative disorders |
| US20060229277A1 (en) | 2005-04-08 | 2006-10-12 | Orbus Pharma, Inc. | Stabilized pharmaceutical compositions comprising an HMG-CoA reductase inhibitor |
| WO2006123185A2 (en) | 2005-05-19 | 2006-11-23 | Merck Sharp & Dohme Limited | Sulphamides for treatment of cancer |
| CA2609343C (en) | 2005-06-07 | 2015-03-31 | Yale University | Methods of treating cancer and other conditions or disease states using lfmau and ldt |
| DK1896421T3 (da) | 2005-06-23 | 2012-01-09 | Merck Sharp & Dohme | Benzocyclohetapyridiner som hæmmere af receptoren tyrosinkinase MET |
| LT1912671T (lt) | 2005-07-18 | 2017-12-11 | Seattle Genetics, Inc. | Vaisto konjugatai, turintys gliukoronido linkerį |
| WO2007014707A1 (en) | 2005-08-01 | 2007-02-08 | F. Hoffmann-La Roche Ag | Heterocyclic benzylamino derivatives, their manufacture and use as pharmaceutical agents |
| CN101300233A (zh) | 2005-09-09 | 2008-11-05 | 先灵公司 | 氮杂稠合的细胞周期蛋白依赖性激酶抑制剂 |
| CA2626016A1 (en) | 2005-10-21 | 2007-06-21 | Panacea Biotec Limited | Pharmaceutical composition comprising at least one anticancer drug and at least one polymer |
| MY167260A (en) | 2005-11-01 | 2018-08-14 | Targegen Inc | Bi-aryl meta-pyrimidine inhibitors of kinases |
| US7528142B2 (en) | 2005-11-03 | 2009-05-05 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| AU2006322314A1 (en) | 2005-11-18 | 2007-06-14 | Synthon B.V. | Zolpidem tablets |
| PT1966202E (pt) | 2005-12-13 | 2012-01-03 | Incyte Corp | Pirrolo[2,3-b] pirimidinas e pirrolo[2,3-b]piridinas substituídas com heteroarilo como inibidores de janus quinase |
| US8014957B2 (en) * | 2005-12-15 | 2011-09-06 | Fred Hutchinson Cancer Research Center | Genes associated with progression and response in chronic myeloid leukemia and uses thereof |
| WO2007081751A2 (en) | 2006-01-05 | 2007-07-19 | The Johns Hopkins University | Compositions and methods for the treatment of cancer |
| EP1981886B1 (en) | 2006-01-31 | 2009-08-12 | F.Hoffmann-La Roche Ag | 7h-pyrido[3,4-d]pyrimidin-8-ones, their manufacture and use as protein kinase inhibitors |
| WO2007106555A2 (en) | 2006-03-14 | 2007-09-20 | Neuren Pharmaceuticals Limited | Oral formulations of glycyl-2-methylprolyl-glutamate |
| US20100261758A1 (en) | 2006-03-28 | 2010-10-14 | Novartis Ag | Heterocyclic amides for use as pharmaceuticals |
| CN102671196B (zh) | 2006-04-05 | 2014-12-03 | 诺华股份有限公司 | 用于治疗癌症的治疗剂的组合 |
| AU2007243519A1 (en) | 2006-04-26 | 2007-11-08 | Merck Sharp & Dohme Corp. | Disubstituted aniline compounds |
| US8299052B2 (en) | 2006-05-05 | 2012-10-30 | Shionogi Inc. | Pharmaceutical compositions and methods for improved bacterial eradication |
| GB0609378D0 (en) | 2006-05-11 | 2006-06-21 | Novartis Ag | Organic compounds |
| US7964728B2 (en) | 2006-07-06 | 2011-06-21 | Solvay Pharmaceuticals B.V. | Azaindole derivatives with a combination of partial nicotinic acetyl-choline receptor agonism and dopamine reuptake inhibition |
| TW200813021A (en) | 2006-07-10 | 2008-03-16 | Merck & Co Inc | Tyrosine kinase inhibitors |
| WO2008009407A2 (en) | 2006-07-17 | 2008-01-24 | Novartis Ag | Sulphonylaminocarbonyl derivatives of bile acid amides for use as immunomodulators |
| US8080252B2 (en) | 2006-07-19 | 2011-12-20 | The Cleveland Clinic Foundation | Compounds and methods of modulating angiogenesis |
| AU2007276760B2 (en) | 2006-07-24 | 2012-01-19 | Tetralogic Pharmaceuticals Corporation | Dimeric IAP antagonists |
| TW200817410A (en) | 2006-08-07 | 2008-04-16 | Incyte Corp | Triazolotriazines as kinase inhibitors |
| PT2068930E (pt) | 2006-08-07 | 2012-10-23 | Abbott Biotherapeutics Corp | Composições e métodos utilizando anticorpos anti-cs1 para tratar mieloma múltiplo |
| WO2008021364A2 (en) | 2006-08-17 | 2008-02-21 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| WO2008022771A1 (en) | 2006-08-23 | 2008-02-28 | Novartis Ag | Amides as sphingomyeline inhibitors |
| US8222288B2 (en) | 2006-08-30 | 2012-07-17 | The Regents Of The University Of Michigan | Small molecule inhibitors of MDM2 and the uses thereof |
| ES2528316T3 (es) | 2006-09-01 | 2015-02-06 | Senhwa Biosciences, Inc. | Moduladores de la serina-treonina proteína quinasa y de PARP |
| WO2008030883A2 (en) | 2006-09-05 | 2008-03-13 | Bipar Sciences, Inc. | Treatment of cancer |
| WO2008030408A2 (en) | 2006-09-05 | 2008-03-13 | Yale University | Proteomimetic compounds as inhibitors of the interaction of a nuclear receptor with coactivator peptides |
| US8242080B2 (en) | 2006-10-13 | 2012-08-14 | The Regents Of The University Of California | Inhibitors of the EGFR kinase targeting the asymmetric activating dimer interface |
| CN103463621B (zh) | 2006-10-31 | 2016-01-06 | 托莱多大学 | Src和Src家族激酶的Na+/K+-ATP酶特异性肽抑制剂/激活剂 |
| JP5103604B2 (ja) | 2006-10-31 | 2012-12-19 | メルク・シャープ・アンド・ドーム・コーポレーション | プロテインキナーゼ阻害剤としての2−アミノチアゾール−4−カルボン酸アミド |
| MY146474A (en) | 2006-11-06 | 2012-08-15 | Supergen Inc | Imidazo[1,2-b]pyridazine and pyrazolo[1,5-a]pyrimidine derivatives and their use as protein kinase inhibitors |
| US20120164075A1 (en) | 2006-11-21 | 2012-06-28 | Jina Pharmaceuticals, Inc. | Endoxifen methods and compositions in the treatment of mammalian diseases |
| US20080125397A1 (en) | 2006-11-28 | 2008-05-29 | Telik, Inc. | 2 (SULFONYL)ETHYL N,N,N',N' tetrakis(2 chloroethyl)phosphorodia |
| US7655799B2 (en) | 2006-11-29 | 2010-02-02 | Telik, Inc. | 2{[2-(substituted amino)ethyl]sulfonyl}ethyl N,N,N',N'-tetrakis(2-chloroethyl)phosphorodiamidates |
| AU2007333105A1 (en) | 2006-12-11 | 2008-06-19 | Kempharm, Inc. | Non-standard amino acid conjugates of amphetamine and processes for making and using the same |
| EP1932820A1 (en) | 2006-12-14 | 2008-06-18 | Bp Oil International Limited | Process for manufacturing neohexene |
| US7956216B2 (en) | 2006-12-21 | 2011-06-07 | The Walter And Eliza Hall Institute Of Medical Research | Alpha-helical mimetics |
| US8536113B2 (en) | 2006-12-21 | 2013-09-17 | Janssen Biotech, Inc. | EGFR binding peptides and uses thereof |
| US8834920B2 (en) | 2006-12-21 | 2014-09-16 | Alza Corporation | Liposome composition for targeting egfr receptor |
| US20080293648A1 (en) | 2007-01-05 | 2008-11-27 | Saha Pharmaceuticals, Inc. | Compositions and Methods for Cancer Treatment |
| ATE483685T1 (de) | 2007-02-06 | 2010-10-15 | Novartis Ag | 1-benzensulfonyl-1h-indol-derivate als hemmer der ccr9-aktivität |
| EP2120900A2 (en) | 2007-02-15 | 2009-11-25 | Novartis AG | Combination of lbh589 with other therapeutic agents for treating cancer |
| AU2008226532B2 (en) | 2007-03-09 | 2011-09-22 | The Regents Of The University Of Michigan | Compositions and methods relating to novel compounds and targets thereof |
| WO2008112277A2 (en) | 2007-03-13 | 2008-09-18 | Wake Forest University | Compositions and methods for treating cancer |
| DK2139484T3 (da) | 2007-04-10 | 2013-10-21 | Exelixis Inc | Fremgangsmåder til behandling af cancer ved brug af pyridopyrimidinon-inhibitorer af PI3K-alfa |
| CA2681311A1 (en) | 2007-04-13 | 2008-10-23 | Novartis Ag | Pyridazine-, pyridine- and pyrane-derivatives as gpbar1 agonisis |
| TWI448284B (zh) | 2007-04-24 | 2014-08-11 | Theravance Inc | 雙效抗高血壓劑 |
| US7838495B2 (en) | 2007-04-27 | 2010-11-23 | University Of Maryland, Baltimore | Compositions and methods of use of EPB1, and ErbB3 binding protein |
| WO2008137619A2 (en) | 2007-05-02 | 2008-11-13 | Vertex Pharmaceuticals Incorporated | Thiazoles and pyrazoles useful as kinase inhibitors |
| US20110021440A1 (en) | 2007-05-16 | 2011-01-27 | University Of Maryland, Baltimore | Apoptotic pathway targeting for the diagnosis and treatment of cancer |
| WO2008153900A1 (en) | 2007-06-06 | 2008-12-18 | University Of Florida Research Foundation | Kinase inhibitor compounds |
| US20110288023A1 (en) | 2007-06-08 | 2011-11-24 | The Regents Of The University Of California Office Of Technology Transfer | Cancer drug delivery using modified transferrin |
| WO2009003911A1 (en) | 2007-06-29 | 2009-01-08 | 4Sc Ag | Thiophene-imidazopyridines |
| JP2010532756A (ja) | 2007-07-06 | 2010-10-14 | オーエスアイ・ファーマスーティカルズ・インコーポレーテッド | mTORC1及びmTORC2の両方の阻害剤を含む組み合わせ抗癌療法 |
| ES2411907T3 (es) | 2007-08-03 | 2013-07-09 | Facet Biotech Corporation | Uso terapéutico de anticuerpos antirreceptor TWEAK |
| HRP20160949T1 (hr) | 2007-09-10 | 2016-10-07 | Boston Biomedical, Inc. | Novi sastavi i metode za liječenje karcinoma |
| WO2009045504A1 (en) | 2007-10-04 | 2009-04-09 | President And Fellows Of Harvard College | Methods and compositions for treating cancer and modulating signal transduction and metabolism pathways |
| SI2211904T1 (sl) | 2007-10-19 | 2016-12-30 | Seattle Genetics, Inc. | CD19 vezavna sredstva in njihove uporabe |
| AU2008317406B2 (en) | 2007-10-25 | 2013-07-18 | Merck Sharp & Dohme Corp. | Therapeutic compounds |
| ES2524787T3 (es) | 2007-11-15 | 2014-12-12 | Msd Italia S.R.L. | Derivados de piridazinona como inhibidores de PARP |
| CA2703600C (en) | 2007-11-15 | 2017-04-25 | Ym Biosciences Australia Pty Ltd | Fused thieno or pyrrolo pyrimidine heterocyclic compounds and use thereof as jak1, jak2, and/or jak3 inhibitors |
| WO2009064835A1 (en) | 2007-11-16 | 2009-05-22 | Incyte Corporation | 4-pyrazolyl-n-arylpyrimidin-2-amines and 4-pyrazolyl-n-heteroarylpyrimidin-2-amines as janus kinase inhibitors |
| CN101444490A (zh) * | 2007-11-26 | 2009-06-03 | 天津市金圭谷木糖醇有限公司 | 一种含脱水卫矛醇经注射给药的制剂及其制备方法 |
| CN101450100A (zh) * | 2007-11-28 | 2009-06-10 | 天津金世制药有限公司 | 一种治疗急慢性粒细胞白血病的药物组合物 |
| WO2009076629A2 (en) | 2007-12-12 | 2009-06-18 | The Regents Of The University Of Michigan | Compositions and methods for treating cancer |
| EP2240172B1 (en) | 2007-12-21 | 2014-03-19 | Novartis AG | Combination of nilotinib and chlorambucil for the treatment of chronic lymphocytic leukemia |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| JP2011511076A (ja) * | 2008-02-08 | 2011-04-07 | エイルロン セラピューティクス,インコーポレイテッド | 治療用ペプチド模倣大環状分子 |
| WO2009102707A2 (en) | 2008-02-11 | 2009-08-20 | Auspex Pharmaceuticals, Inc. | Substituted oxazaphosphorines |
| US20090209340A1 (en) | 2008-02-14 | 2009-08-20 | Aruze Gaming America, Inc. | Gaming Apparatus Capable of Conversation with Player and Control Method Thereof |
| US20110046071A1 (en) | 2008-03-05 | 2011-02-24 | Tel Hashomer Medical Research Infrastructure And Services Ltd. | GLP-1 Receptor Agonists And Related Active Pharmaceutical Ingredients For Treatment Of Cancer |
| BRPI0909040B8 (pt) | 2008-03-11 | 2021-05-25 | Incyte Holdings Corp | derivados de azetidina e ciclobutano, seus usos, e composição |
| EP2110377A1 (en) | 2008-04-15 | 2009-10-21 | DAC S.r.l. | Spirocyclic derivatives as histone deacetylase inhibitors |
| KR101764927B1 (ko) | 2008-04-30 | 2017-08-03 | 이뮤노젠 아이엔씨 | 가교제 및 그 용도 |
| WO2009143018A2 (en) | 2008-05-19 | 2009-11-26 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| EP2303269B1 (en) | 2008-06-03 | 2014-07-30 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
| GB2475183B (en) | 2008-06-04 | 2011-11-23 | Gw Pharma Ltd | Cannabinoids in combination with non-cannabinoid chemotherapeutic agent that are selective estrogen receptor modulators |
| EP2133334A1 (en) | 2008-06-09 | 2009-12-16 | DAC S.r.l. | Heterocyclic derivatives as HDAC inhibitors |
| DK2310011T3 (da) * | 2008-06-17 | 2013-10-14 | Wyeth Llc | Antineoplastiske kombinationer indeholdende hki-272 og vinorelbin |
| US8207195B2 (en) | 2008-06-26 | 2012-06-26 | Inspire Pharmaceuticals, Inc. | Method for treating neurological and neuropathic diseases using rho kinase inhibitor compounds |
| MX2011000235A (es) | 2008-07-08 | 2011-02-23 | Incyte Corp | 1,2,5-oxadiazoles como inhibidores de indolamina 2,3-dioxigenasa. |
| WO2010009334A1 (en) | 2008-07-17 | 2010-01-21 | Colorado State University Research Foundation | Method for preparing largazole analogs and uses thereof |
| JO3041B1 (ar) | 2008-07-25 | 2016-09-05 | Galapagos Nv | مركبات جديدة مفيدة لمعالجة الأمراض التنكسية والالتهابية |
| US20120230991A1 (en) | 2008-07-29 | 2012-09-13 | Douglas Kim Graham | Methods and compounds for enhancing anti-cancer therapy |
| WO2010021822A2 (en) | 2008-07-30 | 2010-02-25 | The Regents Of The University Of California | Discovery of candidate biomarkers of in vivo apoptosis by global profiling of caspase cleavage sites |
| ES2438496T3 (es) | 2008-08-01 | 2014-01-17 | Ventirx Pharmaceuticals, Inc. | Formulaciones de agonistas de receptores de tipo toll y su uso |
| CN102186857A (zh) | 2008-08-26 | 2011-09-14 | 贝林格尔·英格海姆国际有限公司 | 用于药物组合物的噻吩并嘧啶 |
| US20100068302A1 (en) | 2008-09-17 | 2010-03-18 | Traslational Cancer Drugs Pharma, S.L. | Methods and compositions for the treatment of cancer |
| US8476282B2 (en) | 2008-11-03 | 2013-07-02 | Intellikine Llc | Benzoxazole kinase inhibitors and methods of use |
| US20100111901A1 (en) | 2008-11-03 | 2010-05-06 | Auspex Pharmaceuticals, Inc. | Triazole inhibitors of aromatase |
| KR101805754B1 (ko) | 2008-12-08 | 2017-12-07 | 먼디파머 인터내셔널 코포레이션 리미티드 | 단백질 수용체 티로신 키나아제 억제제의 조성물 |
| US20100150896A1 (en) | 2008-12-12 | 2010-06-17 | Auspex Pharmaceuticals, Inc. | Diaminoquinazoline inhibitors of dihydrofolate reductase |
| PA8851101A1 (es) | 2008-12-16 | 2010-07-27 | Lilly Co Eli | Compuesto amino pirazol |
| US20110318430A1 (en) | 2008-12-18 | 2011-12-29 | New York University | Tumor therapy with antitumor agents in combination with sindbis virus-based vectors |
| US20100173013A1 (en) | 2009-01-08 | 2010-07-08 | Denis Drygin | Treatment of neoplastic disorders using combination therapies |
| RU2011136641A (ru) * | 2009-02-04 | 2013-03-10 | Байпар Сайенсиз, Инк. | Лечение рака легких с применением соединения нитробензамида в комбинации с ингибитором фактора роста |
| CN102405044A (zh) | 2009-02-06 | 2012-04-04 | 南加利福尼亚大学 | 含有单萜的治疗组合物 |
| KR101663339B1 (ko) | 2009-03-11 | 2016-10-06 | 플렉시콘 인코퍼레이티드 | Raf 키나제의 억제를 위한 피롤로[2,3-b]피리딘 유도체 |
| AU2010234916A1 (en) | 2009-03-30 | 2011-10-13 | Cerulean Pharma Inc. | Polymer-agent conjugates, particles, compositions, and related methods of use |
| WO2010114805A1 (en) | 2009-03-31 | 2010-10-07 | The Trustees Of The University Of Pennsylvania | Methods of treating cancer with phenformin |
| WO2010114881A1 (en) | 2009-04-01 | 2010-10-07 | Progenra Inc. | Anti-neoplastic compounds, compositions and methods |
| CN102448951B (zh) | 2009-04-06 | 2017-05-10 | 安吉奥斯医药品有限公司 | 丙酮酸激酶m2调节剂、治疗组合物和相关使用方法 |
| US20100291025A1 (en) | 2009-04-13 | 2010-11-18 | Auspex Pharmaceuticals, Inc. | Indazole inhibitors of tyrosine kinase |
| US20110053968A1 (en) | 2009-06-09 | 2011-03-03 | Auspex Pharmaceuticals, Inc. | Aminopyrimidine inhibitors of tyrosine kinase |
| US9151762B2 (en) | 2009-06-12 | 2015-10-06 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Identification of DSG-3 as a biomarker for the detection of metastasis in lymph nodes |
| US8232318B2 (en) | 2009-07-31 | 2012-07-31 | The General Hospital Corporation | Approaches to treat cancer using HB-EGF inhibitors |
| PL2470546T3 (pl) | 2009-08-28 | 2013-12-31 | Takeda Pharmaceuticals Co | Związki heksahydrooksazynopterydynowe do zastosowania jako inhibitory MTOR |
| BR112012005550A2 (pt) | 2009-09-11 | 2015-09-08 | Cylene Pharmaceuticals Inc | lactamas heterociclo-substituídas farmaceuticamente úteis |
| BR112012005970A2 (pt) | 2009-09-16 | 2015-09-08 | Cylene Pharmaceuticals Inc | moduladores tricíclicos de proteína quinase |
| RU2600927C2 (ru) | 2009-09-28 | 2016-10-27 | Ф.Хоффманн-Ля Рош Аг | Бензоксазепиновые ингибиторы pi3k и способы применения |
| US8304577B2 (en) | 2009-10-09 | 2012-11-06 | Bristol-Myers Squibb Company | Modulators of G protein-coupled receptor 88 |
| PH12012500713A1 (en) * | 2009-10-14 | 2012-11-26 | Merck Sharp & Dohme | Substituted piperidines that increase p53 activity and the uses thereof |
| CN110054692A (zh) | 2009-10-23 | 2019-07-26 | 米伦纽姆医药公司 | 抗gcc抗体分子及其相关组合物和方法 |
| AU2010326268B2 (en) | 2009-12-04 | 2016-11-03 | Senhwa Biosciences, Inc. | Pyrazolopyrimidines and related heterocycles as CK2 inhibitors |
| US8445517B2 (en) | 2009-12-11 | 2013-05-21 | Dana-Farber Cancer Institute | Stat modulators |
| US20110195066A1 (en) | 2010-02-05 | 2011-08-11 | Auspex Pharmaceuticals, Inc. | Quinoline inhibitors of tyrosine kinase |
| CA2790199A1 (en) | 2010-02-24 | 2011-09-01 | Auspex Pharmaceuticals, Inc. | Trimethoxyphenyl inhibitors of tyrosine kinase |
| UY33241A (es) | 2010-02-26 | 2011-09-30 | Boehringer Ingelheim Int | ?Tienopirimidinas que contienen heterocicloalquilo para composiciones farmacéuticas?. |
| TW201141483A (en) | 2010-02-26 | 2011-12-01 | Boehringer Ingelheim Int | Thienopyrimidines containing a substituted alkyl group for pharmaceutical compositions |
| WO2011109799A1 (en) | 2010-03-05 | 2011-09-09 | Karyopharm Therapeutics, Inc. | Nuclear transport modulatiors and uses thereof |
| US8389525B2 (en) | 2010-05-05 | 2013-03-05 | Renee Desai | Small molecules for inhibition of protein kinases |
| MX2012013082A (es) | 2010-05-12 | 2013-05-09 | Vertex Pharma | Derivados de 2-aminopiridina utiles como iinhibidores de cinasa atr. |
| WO2011143665A1 (en) * | 2010-05-14 | 2011-11-17 | Genentech, Inc. | Treatment methods |
| EP2600860B1 (en) * | 2010-08-02 | 2020-07-01 | University of Central Florida Research Foundation, Inc. | Substituted 2-hydroxy-4-(2-(phenylsulfonamido)acetamido)benzoic acid analogs as inhibitors of stat proteins |
| SG10201802116RA (en) * | 2010-08-18 | 2018-04-27 | Del Mar Pharmaceuticals | Compositions and methods to improve the therapeutic benefit of suboptimally administered chemical compounds including substituted hexitols such as dianhydrogalactitol and diacetyldianhydrogalactitol |
| US9029103B2 (en) * | 2010-08-27 | 2015-05-12 | Illumina Cambridge Limited | Methods for sequencing polynucleotides |
| US20120213854A1 (en) | 2010-09-30 | 2012-08-23 | Fetzer Oliver S | Methods of treating a subject and related particles, polymers and compositions |
| EP2637669A4 (en) | 2010-11-10 | 2014-04-02 | Infinity Pharmaceuticals Inc | Heterocyclic compounds and their use |
| SG182016A1 (en) * | 2010-12-14 | 2012-07-30 | Univ Singapore | Method of detecting resistance to cancer therapy |
| CA2868302A1 (en) * | 2012-03-23 | 2013-09-26 | Dennis M. Brown | Compositions and methods to improve the therapeutic benefit of indirubin and analogs thereof, including meisoindigo |
| WO2013169600A1 (en) * | 2012-05-09 | 2013-11-14 | Delmar Pharmaceuticals | Veterinary use of dianhydrogalactitol, diacetyldianhydrogalactitol, and dibromodulcitol to treat malignancies |
| US8729286B2 (en) * | 2012-05-10 | 2014-05-20 | Massachusetts Institute Of Technology | Platinum compounds as treatment for cancers, and related methods, kits, and compositions |
-
2013
- 2013-06-24 EP EP13809749.8A patent/EP2872161B1/en active Active
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- 2014-12-24 CL CL2014003526A patent/CL2014003526A1/es unknown
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-
2021
- 2021-02-17 US US17/177,665 patent/US20210251944A1/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| Cancer, 1981, Vol. 47, pp. 442-451* |
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