CN110452221A - (e)-n-{4-[3-氯-4-(2-吡啶甲氧基)苯胺基]-3-氰基-7-乙氧基-6-喹啉基}-4-(二甲氨基)-2-丁烯酰胺马来酸盐及晶形 - Google Patents
(e)-n-{4-[3-氯-4-(2-吡啶甲氧基)苯胺基]-3-氰基-7-乙氧基-6-喹啉基}-4-(二甲氨基)-2-丁烯酰胺马来酸盐及晶形 Download PDFInfo
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- CN110452221A CN110452221A CN201910667051.2A CN201910667051A CN110452221A CN 110452221 A CN110452221 A CN 110452221A CN 201910667051 A CN201910667051 A CN 201910667051A CN 110452221 A CN110452221 A CN 110452221A
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- maleate
- chloro
- anilino
- dimethylamino
- cyano
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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Landscapes
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| US12479607P | 2007-10-17 | 2007-10-17 | |
| US61/124,796 | 2007-10-17 | ||
| CN200880118789.3A CN101918390B (zh) | 2007-10-17 | 2008-10-16 | (e)-n-{4-[3-氯-4-(2-吡啶基甲氧基)苯胺基]-3-氰基-7-乙氧基-6-喹啉基}-4-(二甲基氨基)-2-丁烯酰胺的马来酸盐及其结晶形式 |
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|---|---|---|---|
| CN200880118789.3A Division CN101918390B (zh) | 2007-10-17 | 2008-10-16 | (e)-n-{4-[3-氯-4-(2-吡啶基甲氧基)苯胺基]-3-氰基-7-乙氧基-6-喹啉基}-4-(二甲基氨基)-2-丁烯酰胺的马来酸盐及其结晶形式 |
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| CN201710057547.9A Active CN106822127B (zh) | 2007-10-17 | 2008-10-16 | 来那替尼马来酸盐及晶形 |
| CN202310690478.0A Pending CN116715653A (zh) | 2007-10-17 | 2008-10-16 | 来那替尼马来酸盐及晶形 |
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| CN200880118789.3A Active CN101918390B (zh) | 2007-10-17 | 2008-10-16 | (e)-n-{4-[3-氯-4-(2-吡啶基甲氧基)苯胺基]-3-氰基-7-乙氧基-6-喹啉基}-4-(二甲基氨基)-2-丁烯酰胺的马来酸盐及其结晶形式 |
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| CN201710057547.9A Active CN106822127B (zh) | 2007-10-17 | 2008-10-16 | 来那替尼马来酸盐及晶形 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE10349113A1 (de) | 2003-10-17 | 2005-05-12 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung von Aminocrotonylverbindungen |
| DK1848414T3 (da) * | 2005-02-03 | 2011-07-25 | Gen Hospital Corp | Fremgangsmåde til behandling af gefitinib-resistent cancer |
| AU2006311877A1 (en) | 2005-11-04 | 2007-05-18 | Wyeth Llc | Antineoplastic combinations with mTOR inhibitor, herceptin, and/orHKI-272 |
| US8022216B2 (en) * | 2007-10-17 | 2011-09-20 | Wyeth Llc | Maleate salts of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof |
| SI2310011T1 (sl) | 2008-06-17 | 2013-10-30 | Wyeth Llc | Antineoplastične kombinacije, ki vsebujejo HKI-272 in vinorelbin |
| BRPI0916694B1 (pt) | 2008-08-04 | 2021-06-08 | Wyeth Llc | uso de neratinibe em combinação com capecitabina para tratar câncer de mama metastático de erbb-2 positivo, kit e produto compreendendo os mesmos |
| CA2755789C (en) | 2009-04-06 | 2016-01-19 | Wyeth Llc | Treatment regimen utilizing neratinib for breast cancer |
| CN102428086B (zh) * | 2009-04-29 | 2014-08-20 | 内尔维阿诺医学科学有限公司 | Cdk抑制剂的盐类 |
| CN107441058A (zh) | 2009-11-09 | 2017-12-08 | 惠氏有限责任公司 | 包衣药物球状体及消除或减少病症如呕吐和腹泻的用途 |
| EP3575413A1 (en) | 2009-12-11 | 2019-12-04 | Wyeth LLC | Phosphatidylinositol-3-kinase pathway biomarkers |
| ES2638821T3 (es) * | 2010-01-13 | 2017-10-24 | Wyeth Llc | Un punto de corte en la expresión de la proteína PTEN que identifica tumores con precisión y es predictivo de la respuesta a fármacos a un inhibidor pan-ErbB |
| CN102675287A (zh) * | 2011-03-11 | 2012-09-19 | 江苏恒瑞医药股份有限公司 | (e)-n-[4-[[3-氯-4-(2-吡啶基甲氧基)苯基]氨基]-3-氰基-7-乙氧基-6-喹啉基]-3-[(2r)-1-甲基吡咯烷-2-基]丙-2-烯酰胺的可药用的盐、其制备方法及其在医药上的应用 |
| US9586939B2 (en) | 2011-05-26 | 2017-03-07 | Xuanzhu Pharma Co., Ltd. | Quinazoline derivative as tyrosine-kinase inhibitor, preparation method therefor and application thereof |
| CN103539783A (zh) * | 2012-07-12 | 2014-01-29 | 江苏恒瑞医药股份有限公司 | 一种酪氨酸激酶抑制剂的二马来酸盐的i型结晶及制备方法 |
| CN104513200B (zh) * | 2013-09-26 | 2017-05-03 | 江苏苏中药业集团股份有限公司 | 取代丁烯酰胺的马来酸盐及其晶型 |
| TR201905365T4 (tr) * | 2014-12-12 | 2019-05-21 | Sanofi Sa | Tıbbi aparat ambalajı. |
| EP3229860B1 (en) * | 2014-12-12 | 2019-01-30 | Sanofi | Medical apparatus package |
| CN105367552A (zh) | 2015-01-09 | 2016-03-02 | 苏州晶云药物科技有限公司 | 来那替尼马来酸盐的新晶型及其制备方法 |
| US10774068B2 (en) * | 2015-06-25 | 2020-09-15 | The Scripps Research Institute | Composition and methods for inhibiting mammalian sterile 20-like kinase 1 |
| CN105949176B (zh) * | 2016-06-24 | 2018-10-26 | 浙江海正药业股份有限公司 | 一种来那替尼的纯化方法 |
| EP3475269A1 (en) | 2016-06-27 | 2019-05-01 | Pliva Hrvatska D.O.O. | Solid state forms of neratinib and salts thereof |
| CN107721985A (zh) * | 2016-08-12 | 2018-02-23 | 山东轩竹医药科技有限公司 | 喹唑啉类酪氨酸激酶抑制剂的晶型 |
| CN107721986A (zh) * | 2016-08-12 | 2018-02-23 | 山东轩竹医药科技有限公司 | 喹唑啉类酪氨酸激酶抑制剂的晶型 |
| US11111234B2 (en) | 2016-08-12 | 2021-09-07 | Xuanzhu Pharma Co., Ltd. | Salt of a quinazoline derivative-like tyrosine kinase inhibitor and crystal form thereof |
| CN107721987A (zh) * | 2016-08-12 | 2018-02-23 | 山东轩竹医药科技有限公司 | 喹唑啉类酪氨酸激酶抑制剂的晶型 |
| WO2018134843A1 (en) * | 2017-01-23 | 2018-07-26 | Msn Laboratories Private Limited, R&D Center | Polymorphic forms of (e)-n-{4-[3-chloro-4-((pyridin-2-yl methoxy)anilino]-3-cyano-7- ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide, its maleate salt and process for preparation thereof |
| WO2018189695A1 (en) * | 2017-04-11 | 2018-10-18 | Lupin Limited | Neratinib crystalline forms and process for preparation thereof |
| WO2019015394A1 (zh) * | 2017-07-17 | 2019-01-24 | 苏州科睿思制药有限公司 | 一种来那替尼单马来酸盐的晶型及其制备方法和用途 |
| WO2019096327A1 (en) * | 2017-11-20 | 2019-05-23 | Teligene Ltd | Maleate salts of (e)-n-(3-cyano-7-ethoxy-4-((4-phenoxyphenyl)amino) quinolin-6-yl)-4-(dimethylamino) but-2-enamide and crystalline forms thereof |
| CN107698563B (zh) * | 2017-11-23 | 2020-10-30 | 江苏创诺制药有限公司 | 制备马来酸来那替尼晶型的方法 |
| CN108299394A (zh) * | 2018-02-28 | 2018-07-20 | 江苏创诺制药有限公司 | 来那替尼二马来酸盐晶型及其制备方法 |
| CN110357855A (zh) * | 2018-03-26 | 2019-10-22 | 江苏创诺制药有限公司 | 一种来那替尼盐酸盐晶型及其制备方法 |
| CN109053683A (zh) * | 2018-07-27 | 2018-12-21 | 苏州晶云药物科技股份有限公司 | 来那替尼马来酸盐晶型c的制备方法以及来那替尼马来酸盐晶型c |
| CN109053702A (zh) * | 2018-08-13 | 2018-12-21 | 扬子江药业集团有限公司 | 一种阿法替尼类似物及其制备方法和用途 |
| CN109503479A (zh) * | 2018-12-03 | 2019-03-22 | 四川自豪时代药业有限公司 | 一种磷酸萘酚喹工艺杂质及其合成方法 |
| CN111848581B (zh) * | 2020-08-19 | 2021-08-10 | 昆明学院 | 3-氰基-4-苯胺基-6-氨基喹啉衍生物的制备方法 |
| CN111943933B (zh) * | 2020-09-02 | 2021-05-28 | 重庆医科大学 | 一种来那替尼杂质d的制备方法 |
| CN111995618B (zh) * | 2020-09-02 | 2021-06-11 | 重庆医科大学 | 一种来那替尼杂质g的制备方法 |
| CN114380745A (zh) * | 2020-10-19 | 2022-04-22 | 江苏苏中药业集团股份有限公司 | 一种取代丁烯酰胺颗粒混合物及晶型ii制备方法与应用 |
| CN116723845A (zh) * | 2020-11-02 | 2023-09-08 | 特雷西拉公司 | 脱氧胞苷激酶抑制剂的结晶形式及其用途 |
| JP2023548605A (ja) * | 2020-11-02 | 2023-11-17 | トレセラ コーポレーション | デオキシシチジンキナーゼ阻害剤の結晶形態およびその使用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060270668A1 (en) * | 2005-05-25 | 2006-11-30 | Wyeth | Methods of synthesizing substituted 3-cyanoquinolines and intermediates thereof |
| US20060270669A1 (en) * | 2005-05-25 | 2006-11-30 | Warren Chew | Method of preparing 3-cyano-quinolines and intermediates made thereby |
Family Cites Families (178)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1327358C (en) | 1987-11-17 | 1994-03-01 | Morio Fujiu | Fluoro cytidine derivatives |
| WO1989006692A1 (en) | 1988-01-12 | 1989-07-27 | Genentech, Inc. | Method of treating tumor cells by inhibiting growth factor receptor function |
| EP0940468A1 (en) | 1991-06-14 | 1999-09-08 | Genentech, Inc. | Humanized antibody variable domain |
| AU671491B2 (en) | 1992-12-18 | 1996-08-29 | F. Hoffmann-La Roche Ag | N-oxycarbonyl substituted 5'-deoxy-5-fluorcytidines |
| TW254946B (enExample) | 1992-12-18 | 1995-08-21 | Hoffmann La Roche | |
| US5362718A (en) | 1994-04-18 | 1994-11-08 | American Home Products Corporation | Rapamycin hydroxyesters |
| ZA956029B (en) | 1994-07-22 | 1997-01-20 | Lilly Co Eli | Combination treatment for inhibiting bone loss |
| US5476932A (en) | 1994-08-26 | 1995-12-19 | Hoffmann-La Roche Inc. | Process for producing N4-acyl-5'-deoxy-5-fluorocytidine derivatives |
| GB9508565D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quiazoline derivative |
| GB9508538D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| US5705151A (en) | 1995-05-18 | 1998-01-06 | National Jewish Center For Immunology & Respiratory Medicine | Gene therapy for T cell regulation |
| US6267958B1 (en) | 1995-07-27 | 2001-07-31 | Genentech, Inc. | Protein formulation |
| JP3437685B2 (ja) | 1995-09-12 | 2003-08-18 | 株式会社東芝 | 交直変換装置の制御保護システム |
| US6143764A (en) | 1995-11-07 | 2000-11-07 | Kirin Beer Kabushiki Kaisha | Quinoline and quinazoline derivatives inhibiting platelet-derived growth factor receptor autophosphorylation and pharmaceutical compositions containing the same |
| US5760041A (en) | 1996-02-05 | 1998-06-02 | American Cyanamid Company | 4-aminoquinazoline EGFR Inhibitors |
| UA73073C2 (uk) | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
| US6002008A (en) | 1997-04-03 | 1999-12-14 | American Cyanamid Company | Substituted 3-cyano quinolines |
| RS49733B (sr) * | 1997-05-23 | 2008-04-04 | Sikirić, Predrag dr.sc.., | Soli bpc peptida sa organo- zaštitnom aktivnošću, postupak za njihovo dobijanje i njihova primena |
| US6426383B1 (en) | 1997-05-28 | 2002-07-30 | Nalco Chemical Company | Preparation of water soluble polymer dispersions from vinylamide monomers |
| US6251912B1 (en) | 1997-08-01 | 2001-06-26 | American Cyanamid Company | Substituted quinazoline derivatives |
| US6288082B1 (en) | 1998-09-29 | 2001-09-11 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| US6297258B1 (en) | 1998-09-29 | 2001-10-02 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| PT1117659E (pt) | 1998-09-29 | 2004-04-30 | Wyeth Corp | Cianoquinolinas substituidas como inibidores de tirosina-quinases de proteinas |
| US6432979B1 (en) | 1999-08-12 | 2002-08-13 | American Cyanamid Company | Method of treating or inhibiting colonic polyps and colorectal cancer |
| TWI256395B (en) | 1999-09-29 | 2006-06-11 | Wyeth Corp | Regioselective synthesis of rapamycin derivatives |
| US6277983B1 (en) | 2000-09-27 | 2001-08-21 | American Home Products Corporation | Regioselective synthesis of rapamycin derivatives |
| AU2930501A (en) * | 2000-01-07 | 2001-07-24 | Transform Pharmaceuticals, Inc. | High-throughput formation, identification, and analysis of diverse solid-forms |
| CA2396956C (en) | 2000-01-11 | 2010-10-26 | Biostream Therapeutics, Inc. | Polypharmacophoric agents |
| US6384051B1 (en) | 2000-03-13 | 2002-05-07 | American Cyanamid Company | Method of treating or inhibiting colonic polyps |
| TWI310684B (en) | 2000-03-27 | 2009-06-11 | Bristol Myers Squibb Co | Synergistic pharmaceutical kits for treating cancer |
| GB0008368D0 (en) | 2000-04-06 | 2000-05-24 | Astrazeneca Ab | Combination product |
| US7306801B2 (en) | 2000-05-15 | 2007-12-11 | Health Research, Inc. | Methods of therapy for cancers characterized by overexpression of the HER2 receptor protein |
| CN100448487C (zh) | 2000-08-11 | 2009-01-07 | 惠氏公司 | 治疗雌激素受体阳性癌的方法 |
| TWI286074B (en) | 2000-11-15 | 2007-09-01 | Wyeth Corp | Pharmaceutical composition containing CCI-779 as an antineoplastic agent |
| TWI296196B (en) | 2001-04-06 | 2008-05-01 | Wyeth Corp | Antineoplastic combinations |
| SI1385551T1 (sl) | 2001-04-06 | 2008-12-31 | Wyeth Five Giralda Farms | Antineoplastiäśne kombinacije, ki vsebujejo cci-779 (derivat rapamicina) skupaj z gemcitabinom ali fluorouracilom |
| TWI233359B (en) | 2001-04-06 | 2005-06-01 | Wyeth Corp | Pharmaceutical composition for treating neoplasm |
| ZA200603888B (en) | 2001-06-01 | 2007-05-30 | Wyeth Corp | Antineoplastic combinations |
| JP2004532883A (ja) | 2001-06-01 | 2004-10-28 | ワイス | 抗腫瘍コンビネーション |
| AU2002345670A1 (en) | 2001-06-14 | 2003-01-02 | The Regents Of The University Of California | Mutations in the bcr-abl tyrosine kinase associated with resistance to sti-571 |
| UA77200C2 (en) | 2001-08-07 | 2006-11-15 | Wyeth Corp | Antineoplastic combination of cci-779 and bkb-569 |
| ATE370123T1 (de) | 2001-11-27 | 2007-09-15 | Wyeth Corp | 3-cyanochinoline als inhibitoren von egf-r- und her2-kinasen |
| KR100956195B1 (ko) | 2002-02-01 | 2010-05-06 | 어리어드 파마슈티칼스, 인코포레이티드 | 인 함유 화합물 및 이의 용도 |
| TWI275390B (en) | 2002-04-30 | 2007-03-11 | Wyeth Corp | Process for the preparation of 7-substituted-3- quinolinecarbonitriles |
| US7026330B2 (en) | 2002-05-30 | 2006-04-11 | The Children's Hospital Of Philadelphia | Methods for treatment of acute lymphocytic leukemia |
| EP1509230B1 (en) | 2002-06-05 | 2007-01-03 | Cedars-Sinai Medical Center | Gefitinib (iressa) for the treatment of cancer |
| AU2003248813A1 (en) | 2002-07-05 | 2004-01-23 | Beth Israel Deaconess Medical Center | Combination of mtor inhibitor and a tyrosine kinase inhibitor for the treatment of neoplasms |
| US20040209930A1 (en) | 2002-10-02 | 2004-10-21 | Carboni Joan M. | Synergistic methods and compositions for treating cancer |
| CL2004000016A1 (es) | 2003-01-21 | 2005-04-15 | Wyeth Corp | Compuesto derivado de cloruro de 4-amino-2-butenoilo o una sal farmaceuticamente aceptable del mismo; procedimiento para preparar dicho compuesto, util como intermediario en la sintesis de compuestos inhibidores de proteina quinasa tirosina. |
| CN1437942A (zh) | 2003-02-08 | 2003-08-27 | 杭州华卫制药技术开发有限公司 | 注射用长春瑞滨粉针剂及制备方法 |
| UA83484C2 (uk) | 2003-03-05 | 2008-07-25 | Уайт | Спосіб лікування раку грудей комбінацією похідного рапаміцину і інгібітора ароматази - летрозолу, фармацевтична композиція |
| PL1615640T3 (pl) | 2003-04-22 | 2007-05-31 | Wyeth Corp | Kombinacje przeciwnowotworowe |
| US20050043233A1 (en) | 2003-04-29 | 2005-02-24 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation, migration or apoptosis of myeloma cells or angiogenesis |
| NZ544920A (en) | 2003-07-23 | 2009-11-27 | Bayer Healthcare Llc | 4{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide and metabolites for the treatment and prevention of diseases and conditions |
| US20050025825A1 (en) | 2003-07-31 | 2005-02-03 | Xanodyne Pharmacal, Inc. | Tranexamic acid formulations with reduced adverse effects |
| RU2006106267A (ru) | 2003-08-01 | 2006-07-27 | Уайт Холдингз Корпорейшн (Us) | Применение комбинации ингибитора киназы рецептора эпидермального фактора роста и цитотоксических средств для лечения и ингибирования рака |
| EP1660453A2 (en) | 2003-08-19 | 2006-05-31 | Wyeth Holdings Corporation | Process for the preparation of 4-amino-3-quinolinecarbonitriles |
| US7399865B2 (en) | 2003-09-15 | 2008-07-15 | Wyeth | Protein tyrosine kinase enzyme inhibitors |
| AU2003304497B2 (en) | 2003-09-15 | 2010-06-24 | Wyeth Llc | Substituted quinolines as protein tyrosine kinase enzyme inhibitors |
| TWI372066B (en) | 2003-10-01 | 2012-09-11 | Wyeth Corp | Pantoprazole multiparticulate formulations |
| US20050142192A1 (en) | 2003-10-15 | 2005-06-30 | Wyeth | Oral administration of [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)alkyl] phosphonic acid and derivatives |
| WO2005049021A1 (en) | 2003-11-03 | 2005-06-02 | Oy Helsinki Transplantation R & D Ltd | Materials and methods for inhibiting neointimal hyperplasia |
| US7981618B2 (en) | 2003-11-05 | 2011-07-19 | Board Of Regents Of The University Of Texas System | Diagnostic and therapeutic methods and compositions involving PTEN and breast cancer |
| AR046639A1 (es) | 2003-11-21 | 2005-12-14 | Schering Corp | Combinaciones terapeuticas de anticuerpo anti- igfr1 |
| US7235564B2 (en) | 2003-12-04 | 2007-06-26 | Amr Technology, Inc. | Vinorelbine derivatives |
| US9016221B2 (en) | 2004-02-17 | 2015-04-28 | University Of Florida Research Foundation, Inc. | Surface topographies for non-toxic bioadhesion control |
| AR047988A1 (es) | 2004-03-11 | 2006-03-15 | Wyeth Corp | Combinaciones antineoplásicas de cci-779 y rituximab |
| EP1733056B1 (en) | 2004-03-31 | 2013-05-22 | The General Hospital Corporation | Method to determine responsiveness of cancer to epidermal growth factor receptor targeting treatments |
| US7365206B2 (en) * | 2004-05-28 | 2008-04-29 | Hetero Drugs Limited | Stereoselective synthesis of benzimidazole sulfoxides |
| EP3042964A1 (en) | 2004-06-04 | 2016-07-13 | Genentech, Inc. | Egfr mutations |
| AU2005263972A1 (en) | 2004-07-23 | 2006-01-26 | Astrazeneca Ab | Method of predicting the responsiveness of a tumor to erbB receptor drugs |
| US20060058311A1 (en) | 2004-08-14 | 2006-03-16 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation |
| TW200616612A (en) | 2004-10-08 | 2006-06-01 | Wyeth Corp | Method for the teatment of polycystic kidney disease field of invention |
| US7666901B2 (en) | 2004-10-13 | 2010-02-23 | Wyeth | Analogs of 17-hydroxywortmannin as PI3K inhibitors |
| US20080254497A1 (en) | 2004-10-15 | 2008-10-16 | Monogram Biosciences, Inc. | Response Predictors for Erbb Pathway-Specific Drugs |
| US20060084666A1 (en) | 2004-10-18 | 2006-04-20 | Harari Paul M | Combined treatment with radiation and an epidermal growth factor receptor kinase inhibitor |
| US20080268034A1 (en) | 2005-01-07 | 2008-10-30 | Girish Karanth | Solid Oral Dosage Forms of Ziprasidone Containing Colloidal Silicone Dioxide |
| GB0501999D0 (en) | 2005-02-01 | 2005-03-09 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| DK1848414T3 (da) | 2005-02-03 | 2011-07-25 | Gen Hospital Corp | Fremgangsmåde til behandling af gefitinib-resistent cancer |
| WO2006081985A1 (en) | 2005-02-04 | 2006-08-10 | F. Hoffmann-La Roche Ag | Combined treatment with an n4-(substituted-oxycarbonyl)-5’-deoxy-5-fluorocytidine derivative and an epidermal growth factor receptor kinase inhibitor |
| US7981605B2 (en) | 2005-02-24 | 2011-07-19 | Amgen Inc. | Epidermal growth factor receptor mutations |
| SI1859793T1 (sl) | 2005-02-28 | 2011-08-31 | Eisai R&D Man Co Ltd | Nova kombinirana uporaba sulfonamidne spojine za zdravljenje raka |
| US8828429B2 (en) | 2005-03-03 | 2014-09-09 | Takeda Pharmaceutical Company Limited | Release-control composition |
| US8105768B2 (en) | 2005-03-09 | 2012-01-31 | Abbott Laboratories | Methods of identifying patients for treatment with HER-2/neu inhibitors based on detection of HER-2/neu and TOP2A gene copy number |
| GB0504994D0 (en) | 2005-03-11 | 2005-04-20 | Biotica Tech Ltd | Novel compounds |
| US20060235006A1 (en) | 2005-04-13 | 2006-10-19 | Lee Francis Y | Combinations, methods and compositions for treating cancer |
| RU2007134908A (ru) | 2005-04-14 | 2009-05-20 | Вайет (Us) | Применение ингибитора активности киназы рецептора эпидермального фактора роста для лечения пациентов, невосприимчивых к гефитинибу |
| WO2006116016A2 (en) | 2005-04-21 | 2006-11-02 | The Regents Of The University Of California | Molecular determinants of egfr kinase inhibitor response in glioblastoma |
| MX2007013465A (es) | 2005-04-28 | 2008-01-21 | Wyeth Corp | Tanaproget micronizado, composiciones y metodos para preparar las mismas. |
| CA2603445A1 (en) | 2005-05-12 | 2006-11-16 | Pfizer Inc. | Anticancer combination therapy using sunitinib malate |
| DE102005053679A1 (de) | 2005-06-24 | 2006-12-28 | Bayer Healthcare Ag | Therapeutischer Einsatz von Moxifloxacin zur Rekonstruktion von Funktionsstörungen des Immunsystems |
| AR054833A1 (es) | 2005-07-15 | 2007-07-18 | Wyeth Corp | Formas de dosificacion de liberacion retardada oral altamemte biodisponibles de succinato de o-desmetilvenlafaxina |
| JP5066446B2 (ja) | 2005-08-01 | 2012-11-07 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 血管新生阻害物質の効果を予測する方法 |
| EP2281901B1 (en) | 2005-08-02 | 2013-11-27 | Eisai R&D Management Co., Ltd. | Anti-tumour pharmaceutical composition with angiogenesis inhibitors |
| KR20080028857A (ko) | 2005-10-05 | 2008-04-01 | 아스트라제네카 유케이 리미티드 | ＥｒｂＢ 수용체 약물에 대한 환자반응을 예측 및 모니터링하는 방법 |
| US20110052570A1 (en) | 2005-10-26 | 2011-03-03 | Children's Medical Center Corporation | Method to prognose response to anti-egfr therapeutics |
| AU2006311877A1 (en) | 2005-11-04 | 2007-05-18 | Wyeth Llc | Antineoplastic combinations with mTOR inhibitor, herceptin, and/orHKI-272 |
| US20070105887A1 (en) | 2005-11-04 | 2007-05-10 | Wyeth | Antineoplastic combinations of temsirolimus and sunitinib malate |
| PL1948180T3 (pl) | 2005-11-11 | 2013-09-30 | Boehringer Ingelheim Int | Terapia skojarzona raka polegająca na podawaniu inhibitorów EGFR/HER2 |
| ATE450266T1 (de) | 2005-11-24 | 2009-12-15 | Aicuris Gmbh & Co Kg | Parapocken-viren in kombination mit klassischen zytotoxischen chemotherapeutika als biochemotherapie zur behandlung von krebs |
| JP2007145745A (ja) | 2005-11-25 | 2007-06-14 | Osaka Univ | 変異型ＥＧＦＲ下流シグナルを抑制するＳｒｃファミリーチロシンキナーゼ阻害剤を含む肺癌治療剤およびその利用 |
| EP1965770A2 (en) | 2005-12-22 | 2008-09-10 | Wyeth a Corporation of the State of Delaware | Oral formulations comprising tigecycline |
| WO2007095038A2 (en) | 2006-02-09 | 2007-08-23 | Novartis Ag | Mutations and polymorphisms of erbb2 |
| MX2008012903A (es) | 2006-04-07 | 2008-10-13 | Novartis Ag | Uso de inhibidores de c-src en combinacion con un compuesto de pirimidilaminobenzamida para el tratamiento de la leucemia. |
| TW200806282A (en) | 2006-05-05 | 2008-02-01 | Wyeth Corp | Solid dosage formulations |
| US20100113299A1 (en) | 2008-10-14 | 2010-05-06 | Von Hoff Daniel D | Gene and gene expressed protein targets depicting biomarker patterns and signature sets by tumor type |
| BRPI0711011A2 (pt) | 2006-05-18 | 2011-08-23 | Molecular Profiling Inst Inc | método para a determinação da intervenção médica para um estado de doença, método para a identificação de uma terapia de droga com capacidade de interação com um alvo molecular e sistema para a determinação da intervenção médica individualizada para um estado de doença |
| TW200808728A (en) | 2006-05-23 | 2008-02-16 | Wyeth Corp | Method of preparing 4-halogenated quinoline intermediates |
| JP5399900B2 (ja) | 2006-06-30 | 2014-01-29 | メルク・シャープ・アンド・ドーム・コーポレーション | Ｉｇｆｂｐ２インヒビター |
| US8877764B2 (en) | 2006-09-18 | 2014-11-04 | Boehringer Ingelheim International Gmbh | Method for treating cancer harboring EGFR mutations |
| US8252749B2 (en) | 2006-09-28 | 2012-08-28 | Follica, Inc. | Methods, kits, and compositions for generating new hair follicles and growing hair |
| US20090317456A1 (en) | 2006-10-13 | 2009-12-24 | Medigene Ag | Use of oncolytic viruses and antiangiogenic agents in the treatment of cancer |
| MX2009006466A (es) | 2006-12-13 | 2009-06-26 | Schering Corp | Metodos de tratamiento de cancer con inhibidores del receptor del factor 1 de crecimiento similar a la insulina. |
| EP2121018A2 (en) | 2006-12-13 | 2009-11-25 | Schering Corporation | Treating cancer with anti-igf1r antibody 19d12=sch 717454 |
| AU2007334402B2 (en) | 2006-12-14 | 2014-02-13 | Exelixis, Inc. | Methods of using MEK inhibitors |
| WO2008076143A1 (en) | 2006-12-18 | 2008-06-26 | Osi Pharmaceuticals, Inc. | Combination of igfr inhibitor and anti-cancer agent |
| CA2673472A1 (en) | 2006-12-21 | 2008-07-03 | Vertex Pharmaceuticals Incorporated | 5-cyan0-4- (pyrrolo) [2, 3b] pyridine-3-yl) -pyrimidine derivatives useful as protein kinase inhibitors |
| PE20081632A1 (es) | 2007-01-12 | 2008-12-10 | Wyeth Corp | Composiciones de tableta en tableta |
| MX338185B (es) | 2007-01-25 | 2016-04-05 | Dana Farber Cancer Inst Inc | Uso de anticuerpos anti-egfr en el tratamiento de enfermedad mediada por egfr mutante. |
| CA2677193C (en) | 2007-02-01 | 2015-06-30 | Takeda Pharmaceutical Company Limited | Tablet preparation without causing a tableting trouble |
| WO2008121467A2 (en) | 2007-02-28 | 2008-10-09 | Dana-Farber Cancer Institute, Inc. | Combination therapy for treating cancer |
| GB0706633D0 (en) | 2007-04-04 | 2007-05-16 | Cyclacel Ltd | Combination |
| EP1978106A1 (en) | 2007-04-07 | 2008-10-08 | Universitätsklinikum Hamburg-Eppendorf | Detection of ESR1 amplification in endometrium cancer and ovary cancer |
| US8715665B2 (en) | 2007-04-13 | 2014-05-06 | The General Hospital Corporation | Methods for treating cancer resistant to ErbB therapeutics |
| CA2684265A1 (en) | 2007-04-19 | 2008-10-30 | Wellstat Biologics Corporation | Detection of elevated levels of her-2/neu protein from non-isolated circulating cancer cells and treatment |
| WO2008136838A1 (en) | 2007-05-04 | 2008-11-13 | Trustees Of Dartmouth College | Novel amide derivatives of cddo and methods of use thereof |
| WO2009005673A1 (en) | 2007-06-28 | 2009-01-08 | Schering Corporation | Anti-igf1r |
| CA2736564A1 (en) | 2007-09-10 | 2009-03-19 | Boston Biomedical, Inc. | Novel compositions and methods for cancer treatment |
| US20110306572A1 (en) | 2007-09-24 | 2011-12-15 | Tragara Pharmaceuticals, Inc | COMBINATION THERAPY FOR THE TREATMENT OF CANCER USING COX-2 INHIBITORS AND DUAL InHIBITORS OF EGFR [ErbB1] AND HER-2 [ErbB2] |
| US8022216B2 (en) | 2007-10-17 | 2011-09-20 | Wyeth Llc | Maleate salts of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof |
| WO2009055343A2 (en) | 2007-10-22 | 2009-04-30 | Schering Corporation | Fully human anti-vegf antibodies and methods of using |
| WO2009061349A1 (en) | 2007-11-05 | 2009-05-14 | Puretech Ventures | Methods, kits, and compositions for administering pharmaceutical compounds |
| CN101185633A (zh) | 2007-12-14 | 2008-05-28 | 山东蓝金生物工程有限公司 | 一种治疗实体肿瘤的尼拉替尼缓释植入剂 |
| WO2009079587A2 (en) | 2007-12-18 | 2009-06-25 | Schering Corporation | Biomarkers for sensitivity to anti-igf1r therapy |
| US20100297118A1 (en) | 2007-12-27 | 2010-11-25 | Macdougall John | Therapeutic Cancer Treatments |
| WO2009100176A2 (en) | 2008-02-07 | 2009-08-13 | Abbott Laboratories | Pharmaceutical dosage form for oral administration of tyrosine kinase inhibitor |
| WO2009105234A2 (en) | 2008-02-19 | 2009-08-27 | Combinatorx, Incorporated | Methods and compositions for the treatment of disorders associated with defects of the cystic fibrosis transmembrane conductance regulator gene or protein |
| EP2618146B1 (en) | 2008-02-25 | 2015-06-17 | Nestec S.A. | Drug selection for breast cancer therapy using antibody-based arrays |
| US20100081632A1 (en) | 2008-03-06 | 2010-04-01 | Odyssey Thera, Inc. | High-content and high throughput assays for identification of lipid-regulating pathways, and novel therapeutic agents for lipid disorders |
| CA2718918A1 (en) | 2008-03-25 | 2009-11-26 | Schering Corporation | Methods for treating or preventing colorectal cancer |
| WO2009121031A1 (en) | 2008-03-27 | 2009-10-01 | Vascular Biosciences, Inc. | Methods of novel therapeutic candidate identification through gene expression analysis in vascular-related diseases |
| US20090246198A1 (en) | 2008-03-31 | 2009-10-01 | Takeda Pharmaceutical Company Limited | Mapk/erk kinase inhibitors and methods of use thereof |
| WO2009126662A1 (en) | 2008-04-08 | 2009-10-15 | Syndax Pharmaceuticals, Inc. | Administration of an inhibitor of hdac, an inhibitor of her-2, and a selective estrogen receptor modulator |
| TW201006474A (en) | 2008-04-18 | 2010-02-16 | Reata Pharmaceuticals Inc | Natural products including an anti-flammatory pharmacore and methods of use |
| NZ588711A (en) | 2008-04-18 | 2012-10-26 | Reata Pharmaceuticals Inc | C-17 homologated oleanolic acid derivatives for treating cancer |
| LT2276493T (lt) | 2008-04-18 | 2019-01-10 | Reata Pharmaceuticals, Inc. | Antioksidaciniai uždegimo moduliatoriai: oleanolio rūgšties dariniai su amino ir kitomis modifikacijomis c-17 |
| TW201004627A (en) | 2008-04-18 | 2010-02-01 | Reata Pharmaceuticals Inc | Antioxidant inflammation modulators: novel derivatives of oleanolic acid |
| BRPI0911208B1 (pt) | 2008-04-18 | 2021-05-25 | Reata Pharmaceuticals, Inc | Compostos moduladores inflamatórios antioxidantes, seu uso, e composição farmacêutica |
| US20110129456A1 (en) | 2008-05-05 | 2011-06-02 | Yaolin Wang | Sequential Administration of Chemotherapeutic Agents for Treatment of Cancer |
| WO2009151910A2 (en) | 2008-05-25 | 2009-12-17 | Wyeth | Combination product of receptor tyrosine kinase inhibitor and fatty acid synthase inhibitor for treating cancer |
| SI2310011T1 (sl) | 2008-06-17 | 2013-10-30 | Wyeth Llc | Antineoplastične kombinacije, ki vsebujejo HKI-272 in vinorelbin |
| JP5758801B2 (ja) | 2008-07-22 | 2015-08-05 | トラスティーズ・オブ・ダートマス・カレッジＴｒｕｓｔｅｅｓ ｏｆ Ｄａｒｔｍｏｕｔｈ Ｃｏｌｌｅｇｅ | 単環式シアノエノンおよびその使用方法説明 |
| BRPI0916694B1 (pt) | 2008-08-04 | 2021-06-08 | Wyeth Llc | uso de neratinibe em combinação com capecitabina para tratar câncer de mama metastático de erbb-2 positivo, kit e produto compreendendo os mesmos |
| US20100069340A1 (en) | 2008-09-11 | 2010-03-18 | Wyeth | Pharmaceutical compositions of an src kinase inhibitor and an aromatase inhibitor |
| WO2010048477A2 (en) | 2008-10-24 | 2010-04-29 | Wyeth Llc | Improved process for preparation of coupled products from 4-amino-3-cyanoquinolines using stabilized intermediates |
| WO2010054051A1 (en) | 2008-11-07 | 2010-05-14 | Santaris Pharma A/S | Erbb-3 (her3)-selective combination therapy |
| WO2010085845A1 (en) | 2009-01-28 | 2010-08-05 | The University Of Queensland | Cancer therapy and/or diagnosis |
| KR20110113648A (ko) | 2009-02-04 | 2011-10-17 | 바이파 사이언스 인코포레이티드 | Ｐａｒｐ 억제제와 함께 성장인자 억제제를 사용한 폐암의 치료 |
| WO2010098627A2 (ko) | 2009-02-27 | 2010-09-02 | 한올바이오파마주식회사 | 약제학적 제제 |
| WO2010104406A1 (en) | 2009-03-11 | 2010-09-16 | Auckland Uniservices Limited | Prodrug forms of kinase inhibitors and their use in therapy |
| CA2755789C (en) | 2009-04-06 | 2016-01-19 | Wyeth Llc | Treatment regimen utilizing neratinib for breast cancer |
| AR076053A1 (es) | 2009-04-14 | 2011-05-18 | Schering Corp | Derivados de pirazolo[1,5-a]pirimidina como inhibidores de mtor |
| WO2010124009A2 (en) | 2009-04-21 | 2010-10-28 | Schering Corporation | Fully human anti-vegf antibodies and methods of using |
| KR101705158B1 (ko) | 2009-05-05 | 2017-02-09 | 다나-파버 캔서 인스티튜트 인크. | Ｅｇｆｒ 억제제 및 질환 치료방법 |
| BRPI1015941A2 (pt) | 2009-07-02 | 2016-04-19 | Wyeth Llc | formulações de comprimido de 3-cianoquinolina e uso das mesmas. |
| WO2011008054A2 (ko) | 2009-07-17 | 2011-01-20 | 한올바이오파마주식회사 | Ｎ,ｎ-디메틸 이미도디카르본이미딕 디아미드의 부틸산염, 이의 제조방법, 이를 포함하는 약제학적 조성물 및 이를 포함하는 복합제제 |
| WO2011008053A2 (ko) | 2009-07-17 | 2011-01-20 | 한올바이오파마주식회사 | Ｎ,ｎ-디메틸 이미도디카르본이미딕 디아미드의 프로피온산염, 이의 제조방법, 이를 포함하는 약제학적 조성물 및 이를 포함하는 복합제제 |
| WO2011025267A2 (ko) | 2009-08-25 | 2011-03-03 | 한올바이오파마주식회사 | 메트포르민 메탄설폰산염, 그의 제조방법, 그를 포함하는 약학 조성물 및 그를 포함하는 복합제제 |
| WO2011025271A2 (ko) | 2009-08-25 | 2011-03-03 | 한올바이오파마주식회사 | 메트포르민 아스코르브산염, 그의 제조방법, 그를 포함하는 약학 조성물 및 그를 포함하는 복합제제 |
| WO2011025269A2 (ko) | 2009-08-25 | 2011-03-03 | 한올바이오파마주식회사 | 메트포르민 타우린염, 그의 제조방법, 그를 포함하는 약학 조성물 및 그를 포함하는 복합제제 |
| US20110055838A1 (en) | 2009-08-28 | 2011-03-03 | Moyes William A | Optimized thread scheduling via hardware performance monitoring |
| US20120244116A1 (en) | 2009-10-01 | 2012-09-27 | Csl Limited | Method of treatment of philadelphia chromosome positive leukaemia |
| ES2757882T5 (es) | 2009-11-09 | 2023-05-10 | Wyeth Llc | Formulaciones de comprimidos de maleato de neratinib |
| CN107441058A (zh) | 2009-11-09 | 2017-12-08 | 惠氏有限责任公司 | 包衣药物球状体及消除或减少病症如呕吐和腹泻的用途 |
| NO2719708T3 (enExample) | 2009-11-13 | 2018-03-24 | ||
| US20130012465A1 (en) | 2009-12-07 | 2013-01-10 | Boehringer Ingelheim International Gmbh | Bibw 2992 for use in the treatment of triple negative breast cancer |
| EP3575413A1 (en) | 2009-12-11 | 2019-12-04 | Wyeth LLC | Phosphatidylinositol-3-kinase pathway biomarkers |
| ES2638821T3 (es) | 2010-01-13 | 2017-10-24 | Wyeth Llc | Un punto de corte en la expresión de la proteína PTEN que identifica tumores con precisión y es predictivo de la respuesta a fármacos a un inhibidor pan-ErbB |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060270668A1 (en) * | 2005-05-25 | 2006-11-30 | Wyeth | Methods of synthesizing substituted 3-cyanoquinolines and intermediates thereof |
| US20060270669A1 (en) * | 2005-05-25 | 2006-11-30 | Warren Chew | Method of preparing 3-cyano-quinolines and intermediates made thereby |
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