ES2604668T3 - Nuevos derivados de benzodiacepina - Google Patents
Nuevos derivados de benzodiacepina Download PDFInfo
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- ES2604668T3 ES2604668T3 ES10739103.9T ES10739103T ES2604668T3 ES 2604668 T3 ES2604668 T3 ES 2604668T3 ES 10739103 T ES10739103 T ES 10739103T ES 2604668 T3 ES2604668 T3 ES 2604668T3
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Classifications
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| PCT/US2010/023150 WO2010091150A1 (en) | 2009-02-05 | 2010-02-04 | Novel benzodiazepine derivatives |
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Families Citing this family (187)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20100056762A1 (en) | 2001-05-11 | 2010-03-04 | Old Lloyd J | Specific binding proteins and uses thereof |
| PT2163256E (pt) | 2001-05-11 | 2015-11-20 | Ludwig Inst For Cancer Res Ltd | Proteínas de ligação específica e suas utilizações |
| US7742064B2 (en) * | 2001-10-30 | 2010-06-22 | Semiconductor Energy Laboratory Co., Ltd | Signal line driver circuit, light emitting device and driving method thereof |
| US20110166319A1 (en) * | 2005-02-11 | 2011-07-07 | Immunogen, Inc. | Process for preparing purified drug conjugates |
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| ES2609094T3 (es) | 2007-01-25 | 2017-04-18 | Dana-Farber Cancer Institute, Inc. | Uso de anticuerpos anti-EGFR en el tratamiento de enfermedades mediadas por un EGFR mutante |
| CA2680854C (en) | 2007-03-15 | 2017-02-14 | Ludwig Institute For Cancer Research | Treatment method using egfr antibodies and src inhibitors and related formulations |
| EP2188311B1 (en) | 2007-08-14 | 2016-10-05 | Ludwig Institute for Cancer Research Ltd. | Monoclonal antibody 175 targeting the egf receptor and derivatives and uses thereof |
| CN105198908B (zh) * | 2009-02-05 | 2019-12-24 | 伊缪诺金公司 | 新型苯并二氮杂*衍生物 |
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| KR20170085143A (ko) | 2010-02-24 | 2017-07-21 | 이뮤노젠 아이엔씨 | 엽산염 수용체 1 항체와 면역접합체 및 이들의 용도 |
| CN103068405A (zh) | 2010-04-15 | 2013-04-24 | 西雅图基因公司 | 靶向吡咯并苯并二氮杂卓结合物 |
| ES2623057T3 (es) | 2010-04-15 | 2017-07-10 | Medimmune Limited | Pirrolobenzodiazepinas usadas para tratar enfermedades proliferativas |
| CN102933236B (zh) | 2010-04-15 | 2014-10-08 | 斯皮罗根有限公司 | 吡咯并苯二氮卓类及其结合物 |
| FR2963007B1 (fr) * | 2010-07-26 | 2013-04-05 | Sanofi Aventis | Derives anticancereux, leur preparation et leur application therapeutique |
| DK3153504T3 (en) | 2010-12-09 | 2019-01-07 | Immunogen Inc | PROCEDURES FOR MANUFACTURING CHARGED CROSS BINDERS |
| AU2015202826B2 (en) * | 2011-02-15 | 2017-03-30 | Immunogen, Inc. | Cytotoxic benzodiazepine derivatives |
| PT2675480T (pt) * | 2011-02-15 | 2019-04-15 | Immunogen Inc | Métodos para preparação de conjugados |
| MX339927B (es) | 2011-03-29 | 2016-06-16 | Immunogen Inc | Preparacion de conjugados de maitansinoides y anticuerpos mediante un proceso de una etapa. |
| EP2524929A1 (en) * | 2011-05-17 | 2012-11-21 | Sanofi | Use of anti-CD19 maytansinoid immunoconjugate antibody for the treatment of CD19+ B-cell malignancies syptoms |
| US8815226B2 (en) | 2011-06-10 | 2014-08-26 | Mersana Therapeutics, Inc. | Protein-polymer-drug conjugates |
| EP2717916B1 (en) | 2011-06-10 | 2017-03-08 | Mersana Therapeutics, Inc. | Protein-polymer-drug conjugates |
| CN103987718A (zh) | 2011-09-20 | 2014-08-13 | 斯皮罗根有限公司 | 作为非对称二聚体pbd化合物用于内含在靶向结合物中的吡咯并苯并二氮杂卓 |
| CA2850375C (en) | 2011-10-14 | 2019-07-02 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| CN103998449A (zh) | 2011-10-14 | 2014-08-20 | 斯皮罗根有限公司 | 吡咯并苯并二氮杂卓 |
| CA2850373C (en) | 2011-10-14 | 2019-07-16 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| CN103998450B (zh) | 2011-10-14 | 2017-03-08 | 麦迪穆有限责任公司 | 吡咯并苯并二氮杂卓 |
| WO2013055987A1 (en) | 2011-10-14 | 2013-04-18 | Spirogen Sàrl | Pyrrolobenzodiazepines and conjugates thereof |
| CN104093425A (zh) * | 2011-12-13 | 2014-10-08 | 伊缪诺金公司 | N-羟基琥珀酰亚胺用于改善缀合物的稳定性的用途 |
| KR102144069B1 (ko) | 2012-05-15 | 2020-08-13 | 시애틀 지네틱스, 인크. | 자가-안정화 링커 접합체 |
| US9504756B2 (en) | 2012-05-15 | 2016-11-29 | Seattle Genetics, Inc. | Self-stabilizing linker conjugates |
| WO2013177481A1 (en) | 2012-05-25 | 2013-11-28 | Immunogen, Inc. | Benzodiazepines and conjugates thereof |
| HK1211208A1 (zh) | 2012-08-22 | 2016-05-20 | Immunogen, Inc. | 細胞毒性苯並二氮呯衍生物 |
| SG11201502429YA (en) | 2012-10-04 | 2015-04-29 | Immunogen Inc | Use of a pvdf membrane to purify cell-binding agent cytotoxic agent conjugates |
| ES2680153T3 (es) | 2012-10-12 | 2018-09-04 | Adc Therapeutics Sa | Conjugados de anticuerpos anti-PSMA-pirrolobenzodiazepinas |
| HRP20182129T1 (hr) * | 2012-10-12 | 2019-02-08 | Adc Therapeutics Sa | Konjugati protutijelo - pirolobenzodiazepin |
| RS58921B1 (sr) | 2012-10-12 | 2019-08-30 | Medimmune Ltd | Pirolobenzodiazepini i njihovi konjugati |
| PT2906253T (pt) | 2012-10-12 | 2018-11-05 | Medimmune Ltd | Conjugados de anticorpo anti-psma de pirrolobenzodiazepina |
| CN104703630A (zh) | 2012-10-12 | 2015-06-10 | 斯皮罗根有限公司 | 吡咯并苯并二氮杂卓及其结合物 |
| HRP20180945T1 (hr) * | 2012-10-12 | 2018-08-10 | Adc Therapeutics Sa | Konjugati protutijelo-pirolobenzodiazepin |
| CA2885305C (en) | 2012-10-12 | 2019-11-12 | Spirogen Sarl | Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation |
| WO2014057120A1 (en) * | 2012-10-12 | 2014-04-17 | Adc Therapeutics Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| LT2906251T (lt) | 2012-10-12 | 2017-12-11 | Adc Therapeutics Sa | Pirolobenzodiazepino-anti-cd22 antikūno konjugatai |
| JP6133431B2 (ja) | 2012-11-24 | 2017-05-24 | ハンジョウ ディーエーシー バイオテック シーオー.,エルティディ.Hangzhou Dac Biotech Co.,Ltd. | 親水性連結体及び薬物分子と細胞結合分子との共役反応における親水性連結体の使用 |
| JP6527466B2 (ja) | 2012-12-21 | 2019-06-05 | メドイミューン・リミテッドMedImmune Limited | 増殖性疾患および自己免疫疾患の治療に使用するための非対称ピロロベンゾジアゼピンニ量体 |
| WO2014096368A1 (en) | 2012-12-21 | 2014-06-26 | Spirogen Sàrl | Pyrrolobenzodiazepines and conjugates thereof |
| NZ710746A (en) | 2013-03-13 | 2018-11-30 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| US9453046B2 (en) | 2013-03-13 | 2016-09-27 | Seattle Genetics, Inc. | Activated carbon filtration for purification of benzodiazepine ADCs |
| KR102066319B1 (ko) | 2013-03-13 | 2020-01-14 | 메디뮨 리미티드 | 피롤로벤조디아제핀 및 그의 컨쥬게이트 |
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| HK1220698A1 (zh) | 2013-03-13 | 2017-05-12 | Seattle Genetics, Inc. | 环糊精和抗体药物偶联物制剂 |
| EP2970474B1 (en) | 2013-03-14 | 2017-12-20 | Genentech, Inc. | Anti-b7-h4 antibodies and immunoconjugates |
| US9562099B2 (en) | 2013-03-14 | 2017-02-07 | Genentech, Inc. | Anti-B7-H4 antibodies and immunoconjugates |
| JP6574754B2 (ja) | 2013-03-19 | 2019-09-11 | ベイジン シェノゲン ファーマ グループ リミテッド | エストロゲン受容体関連疾患を処置するための抗体及び方法 |
| US10208125B2 (en) | 2013-07-15 | 2019-02-19 | University of Pittsburgh—of the Commonwealth System of Higher Education | Anti-mucin 1 binding agents and uses thereof |
| US10442836B2 (en) * | 2013-08-12 | 2019-10-15 | Genentech, Inc. | 1-(chloromethyl)-2,3-dihydro-1H-benzo[E]indole dimer antibody-drug conjugate compounds, and methods of use and treatment |
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| BR112016007736B1 (pt) | 2013-10-11 | 2022-09-27 | Mersana Therapeutics, Inc | Armação polimérica, e, composição farmacêutica |
| IL245009B (en) | 2013-10-11 | 2022-08-01 | Asana Biosciences Llc | Protein-polymer-drug conjugates |
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| WO2015052534A1 (en) | 2013-10-11 | 2015-04-16 | Spirogen Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| WO2015052535A1 (en) | 2013-10-11 | 2015-04-16 | Spirogen Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| GB201317981D0 (en) | 2013-10-11 | 2013-11-27 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| JP6747971B2 (ja) | 2013-10-15 | 2020-08-26 | シアトル ジェネティックス, インコーポレイテッド | 改善されたリガンド−薬物コンジュゲート薬物動態のためのpeg化薬物−リンカー |
| SG11201604784XA (en) | 2013-12-13 | 2016-07-28 | Genentech Inc | Anti-cd33 antibodies and immunoconjugates |
| MX2016007578A (es) | 2013-12-16 | 2016-10-03 | Genentech Inc | Compuestos de conjugado anticuerpo-farmaco dimerico de 1-(clorometil)-2,3-dihidro-1h-benzo [e] indol, y metodos de uso y tratamiento. |
| CN106062002B (zh) * | 2013-12-17 | 2021-05-04 | 埃姆医疗有限公司 | 抵抗骨髓增生障碍或淋巴组织增生障碍的手段和方法 |
| EP4190809A1 (en) | 2014-02-11 | 2023-06-07 | Seagen Inc. | Selective reduction of proteins |
| US10464955B2 (en) | 2014-02-28 | 2019-11-05 | Hangzhou Dac Biotech Co., Ltd. | Charged linkers and their uses for conjugation |
| MX2016015162A (es) | 2014-05-22 | 2017-03-03 | Genentech Inc | Anticuerpos anti - gpc3 e inmunoconjugados. |
| WO2016008112A1 (en) | 2014-07-16 | 2016-01-21 | Medshine Discovery Inc. | Linkers and application towards adc thereof |
| JP2017527562A (ja) * | 2014-09-03 | 2017-09-21 | イミュノジェン・インコーポレーテッド | 細胞毒性ベンゾジアゼピン誘導体 |
| ES2815353T3 (es) * | 2014-09-03 | 2021-03-29 | Immunogen Inc | Derivados de benzodiazepina citotóxicos |
| CN106687141A (zh) | 2014-09-10 | 2017-05-17 | 麦迪穆有限责任公司 | 吡咯并苯并二氮杂卓及其缀合物 |
| EP3191518B1 (en) | 2014-09-12 | 2020-01-15 | Genentech, Inc. | Anti-b7-h4 antibodies and immunoconjugates |
| GB201416112D0 (en) | 2014-09-12 | 2014-10-29 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| PL3191135T3 (pl) | 2014-09-12 | 2021-01-25 | Genentech, Inc. | Przeciwciała i immunokoniugaty anty-HER2 |
| EP3191520B1 (en) | 2014-09-12 | 2020-01-01 | Genentech, Inc. | Anti-cll-1 antibodies and immunoconjugates |
| JP2017531620A (ja) | 2014-09-12 | 2017-10-26 | ジェネンテック, インコーポレイテッド | システイン操作抗体及びコンジュゲート |
| PE20170905A1 (es) | 2014-09-17 | 2017-07-12 | Genentech Inc | Pirrolobenzodiazepinas y conjugados de anticuerpo-disulfuro de las mismas |
| HK1243629A1 (zh) | 2014-09-17 | 2018-07-20 | 基因泰克公司 | 包含抗her2抗体和吡咯并苯并二氮杂䓬的免疫缀合物 |
| KR20170101895A (ko) | 2014-11-25 | 2017-09-06 | 에이디씨 테라퓨틱스 에스에이 | 피롤로벤조디아제핀-항체 접합체 |
| JP6498773B2 (ja) * | 2015-01-14 | 2019-04-10 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | ベンゾジアゼピン二量体、そのコンジュゲート、ならびに製造および使用方法 |
| JP6676058B2 (ja) | 2015-01-14 | 2020-04-08 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | ヘテロアリーレン架橋したベンゾジアゼピン二量体、そのコンジュゲート、ならびに製造および使用方法 |
| US9504694B2 (en) | 2015-03-19 | 2016-11-29 | Cellerant Therapeutics, Inc. | Isoquinolidinobenzodiazepines |
| GB201506411D0 (en) | 2015-04-15 | 2015-05-27 | Bergenbio As | Humanized anti-axl antibodies |
| GB201506402D0 (en) | 2015-04-15 | 2015-05-27 | Berkel Patricius H C Van And Howard Philip W | Site-specific antibody-drug conjugates |
| EA039619B1 (ru) * | 2015-05-20 | 2022-02-17 | Иммуноджен, Инк. | Способ получения индолинобензодиазепиновых соединений |
| GB201510010D0 (en) * | 2015-06-09 | 2015-07-22 | King S College London | PDD and BPD compounds |
| CN108026123B (zh) | 2015-06-15 | 2021-02-05 | 杭州多禧生物科技有限公司 | 用于偶联的亲水链接体 |
| MX2017015814A (es) | 2015-06-23 | 2018-04-10 | Squibb Bristol Myers Co | Dimeros de benzodiazepina macrociclica, conjugados de los mismos, preparacion y usos. |
| LT3313845T (lt) | 2015-06-29 | 2020-12-10 | Immunogen, Inc. | Cisteino inžinerijos antikūnų konjugatai |
| CN113350518A (zh) | 2015-07-12 | 2021-09-07 | 杭州多禧生物科技有限公司 | 与细胞结合分子的共轭偶联的桥连接体 |
| US9839687B2 (en) | 2015-07-15 | 2017-12-12 | Suzhou M-Conj Biotech Co., Ltd. | Acetylenedicarboxyl linkers and their uses in specific conjugation of a cell-binding molecule |
| US10081640B2 (en) * | 2015-07-21 | 2018-09-25 | Immunogen, Inc. | Methods of preparing cytotoxic benzodiazepine derivatives |
| US20180339985A1 (en) | 2015-08-21 | 2018-11-29 | Femtogenix Limited | Pdd compounds |
| GB201514928D0 (en) * | 2015-08-21 | 2015-10-07 | King S College London | PDD compounds |
| EP3350224B1 (en) | 2015-09-20 | 2024-06-19 | The United States of America, as Represented By the Secretary, Department of Health and Human Services | Monoclonal antibodies specific for fibroblast growth factor receptor 4 (fgfr4) and methods of their use |
| MA43345A (fr) | 2015-10-02 | 2018-08-08 | Hoffmann La Roche | Conjugués anticorps-médicaments de pyrrolobenzodiazépine et méthodes d'utilisation |
| MA43354A (fr) | 2015-10-16 | 2018-08-22 | Genentech Inc | Conjugués médicamenteux à pont disulfure encombré |
| WO2017091745A1 (en) | 2015-11-25 | 2017-06-01 | Immunogen, Inc. | Pharmaceutical formulations and methods of use thereof |
| US11229708B2 (en) | 2015-12-04 | 2022-01-25 | Seagen Inc. | Conjugates of quaternized tubulysin compounds |
| US11793880B2 (en) | 2015-12-04 | 2023-10-24 | Seagen Inc. | Conjugates of quaternized tubulysin compounds |
| GB201601431D0 (en) | 2016-01-26 | 2016-03-09 | Medimmune Ltd | Pyrrolobenzodiazepines |
| GB201602359D0 (en) | 2016-02-10 | 2016-03-23 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| GB201602356D0 (en) | 2016-02-10 | 2016-03-23 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| EP3433278A4 (en) | 2016-03-25 | 2019-11-06 | Seattle Genetics, Inc. | METHOD FOR THE PRODUCTION OF PEGYLATED ACTIVE LINKERS AND INTERMEDIATE PRODUCTS THEREOF |
| MA45328A (fr) | 2016-04-01 | 2019-02-06 | Avidity Biosciences Llc | Compositions acide nucléique-polypeptide et utilisations de celles-ci |
| FR3049605B1 (fr) * | 2016-04-05 | 2018-03-23 | Arkema France | Procede d'obtention de films fins et articles filmogenes |
| US10934359B2 (en) | 2016-04-21 | 2021-03-02 | Abbvie Stemcentrx Llc | Anti-BMPR1B antibodies and methods of use |
| GB201607478D0 (en) | 2016-04-29 | 2016-06-15 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| WO2017196847A1 (en) | 2016-05-10 | 2017-11-16 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Variable new antigen receptor (vnar) antibodies and antibody conjugates targeting tumor and viral antigens |
| WO2017201132A2 (en) | 2016-05-18 | 2017-11-23 | Mersana Therapeutics, Inc. | Pyrrolobenzodiazepines and conjugates thereof |
| EP3465221B1 (en) | 2016-05-27 | 2020-07-22 | H. Hoffnabb-La Roche Ag | Bioanalytical method for the characterization of site-specific antibody-drug conjugates |
| WO2017214182A1 (en) | 2016-06-07 | 2017-12-14 | The United States Of America. As Represented By The Secretary, Department Of Health & Human Services | Fully human antibody targeting pdi for cancer immunotherapy |
| JP7049276B2 (ja) | 2016-06-24 | 2022-04-06 | メルサナ セラピューティクス インコーポレイテッド | ピロロベンゾジアゼピンおよびその結合体 |
| CA3031559A1 (en) | 2016-08-02 | 2018-02-08 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Monoclonal antibodies targeting glypican-2 (gpc2) and use thereof |
| CN109562152B (zh) | 2016-08-09 | 2024-04-02 | 西雅图基因公司 | 含有具有改善的生理化学性质的自稳定性接头的药物缀合物 |
| JP7093767B2 (ja) | 2016-08-11 | 2022-06-30 | ジェネンテック, インコーポレイテッド | ピロロベンゾジアゼピンプロドラッグ及びその抗体コンジュゲート |
| EP3522932A4 (en) | 2016-10-10 | 2020-06-24 | Cellerant Therapeutics, Inc. | ISOCHINOLIDINOBENZODIAZEPINE (IQB) -1 (CHLORMETHYL) -2,3-DIHYDRO-1-H-BENZO [E] INDOL (CBI) DIMERS |
| GB201617466D0 (en) | 2016-10-14 | 2016-11-30 | Medimmune Ltd | Pyrrolobenzodiazepine conjugates |
| US20200261470A1 (en) * | 2016-11-02 | 2020-08-20 | Immunogen, Inc. | Combination treatment with antibody-drug conjugates and parp inhibitors |
| CN116143678A (zh) | 2016-11-14 | 2023-05-23 | 杭州多禧生物科技有限公司 | 偶联连接体,含有此连接体的细胞结合分子-药物偶联物及其制备和应用 |
| KR102221364B1 (ko) | 2016-11-21 | 2021-03-04 | 쿠레아브 게엠베하 | 항-gp73 항체 및 면역접합체 |
| WO2018098258A2 (en) | 2016-11-23 | 2018-05-31 | Immunogen, Inc. | Selective sulfonation of benzodiazepine derivatives |
| JP7244987B2 (ja) | 2016-12-14 | 2023-03-23 | シージェン インコーポレイテッド | 多剤抗体薬物コンジュゲート |
| CN110234348B (zh) | 2016-12-16 | 2024-06-25 | 蓝鳍生物医药公司 | 抗-含cub结构域蛋白1(cdcp1)抗体、抗体药物缀合物及其使用方法 |
| CA3045902A1 (en) | 2016-12-21 | 2018-06-28 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Human monoclonal antibodies specific for flt3 and uses thereof |
| WO2018119196A1 (en) | 2016-12-23 | 2018-06-28 | Immunogen, Inc. | Immunoconjugates targeting adam9 and methods of use thereof |
| US20180230218A1 (en) | 2017-01-04 | 2018-08-16 | Immunogen, Inc. | Met antibodies and immunoconjugates and uses thereof |
| GB201702031D0 (en) | 2017-02-08 | 2017-03-22 | Medlmmune Ltd | Pyrrolobenzodiazepine-antibody conjugates |
| SI3544636T1 (sl) | 2017-02-08 | 2021-08-31 | Adc Therapeutics Sa | Konjugati pirolobenzodiazepin-protitelo |
| CN110430901B (zh) | 2017-03-24 | 2024-08-16 | 西雅图基因公司 | 制备葡糖苷酸药物-接头及其中间体的方法 |
| HRP20221063T1 (hr) | 2017-04-18 | 2022-11-11 | Medimmune Limited | Konjugati pirolobenzodiazepina |
| CN115448926A (zh) * | 2017-04-20 | 2022-12-09 | 伊缪诺金公司 | 制备吲哚啉并苯并二氮杂䓬衍生物的方法 |
| WO2018193102A1 (en) | 2017-04-20 | 2018-10-25 | Adc Therapeutics Sa | Combination therapy with an anti-axl antibody-drug conjugate |
| CA3059232A1 (en) * | 2017-04-27 | 2018-11-01 | The Brigham And Women's Hospital, Inc. | Novel alk2 inhibitors and methods for inhibiting bmp signaling |
| US11389480B2 (en) | 2017-05-19 | 2022-07-19 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Human monoclonal antibody targeting TNFR2 for cancer immunotherapy |
| ES2988683T3 (es) | 2017-06-14 | 2024-11-21 | Adc Therapeutics Sa | Pautas posológicas para la administración de un CAF anti-CD19 |
| WO2019005208A1 (en) | 2017-06-30 | 2019-01-03 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | ANTIBODIES TO HUMAN MESOTHELIN AND USES IN ANTICANCER THERAPY |
| WO2019006280A1 (en) | 2017-06-30 | 2019-01-03 | Lentigen Technology, Inc. | HUMAN MONOCLONAL ANTIBODIES SPECIFIC TO CD33 AND METHODS OF USE |
| US12227567B2 (en) | 2017-07-25 | 2025-02-18 | Truebinding, Inc. | Treating cancer by blocking the interaction of TIM-3 and its ligand |
| JP7220203B2 (ja) | 2017-08-18 | 2023-02-09 | メドイミューン・リミテッド | ピロロベンゾジアゼピン複合体 |
| MX2020003125A (es) | 2017-09-29 | 2020-10-01 | Daiichi Sankyo Co Ltd | Conjugado de anticuerpo-derivado de pirrolobenzodiazepina. |
| US11638760B2 (en) | 2017-11-27 | 2023-05-02 | Mersana Therapeutics, Inc. | Pyrrolobenzodiazepine antibody conjugates |
| EP3732178A1 (en) * | 2017-12-28 | 2020-11-04 | ImmunoGen, Inc. | Benzodiazepine derivatives |
| GB201803342D0 (en) | 2018-03-01 | 2018-04-18 | Medimmune Ltd | Methods |
| GB201806022D0 (en) | 2018-04-12 | 2018-05-30 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| US11084801B2 (en) | 2018-05-29 | 2021-08-10 | Intocell, Inc. | Benzodiazepine derivatives and uses thereof |
| CA3105694A1 (en) | 2018-07-12 | 2020-01-16 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Affinity matured cd22-specific monoclonal antibody and uses thereof |
| WO2020033430A1 (en) | 2018-08-08 | 2020-02-13 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | High affinity monoclonal antibodies targeting glypican-2 and uses thereof |
| TWI897855B (zh) | 2018-10-26 | 2025-09-21 | 美商免疫遺傳股份有限公司 | E p C A M 抗體、可活化抗體及免疫偶聯物以及其用途 |
| US12274898B2 (en) | 2018-10-31 | 2025-04-15 | Intocell, Inc. | Substituted benzodiazepines as antibody-drug conjugates |
| IL319265A (en) | 2018-12-21 | 2025-04-01 | Avidity Biosciences Inc | Anti-transferrin receptor antibodies and their uses |
| US12180296B2 (en) | 2019-01-08 | 2024-12-31 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Cross species single domain antibodies targeting mesothelin for treating solid tumors |
| US12122843B2 (en) | 2019-01-22 | 2024-10-22 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | High affinity monoclonal antibodies targeting glypican-1 and methods of use |
| EP3918323A4 (en) | 2019-01-30 | 2022-12-28 | TrueBinding, Inc. | ANTI-GAL3 ANTIBODIES AND THEIR USES |
| CN113631560B (zh) | 2019-03-15 | 2025-02-18 | 麦迪穆有限责任公司 | 氮杂环丁烷并苯并二氮杂䓬二聚体和用于治疗癌症的包含它们的缀合物 |
| MA55520A (fr) * | 2019-03-29 | 2022-02-09 | Immunogen Inc | Dérivés de bis-benzodiazépine cytotoxiques et leurs conjugués avec des agents de liaison à une cellule pour inhiber la croissance cellulaire anormale ou pour traiter des maladies prolifératives |
| CA3156761A1 (en) | 2019-10-22 | 2021-04-29 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | High affinity nanobodies targeting b7h3 (cd276) for treating multiple solid tumors |
| US20230032465A1 (en) | 2019-12-12 | 2023-02-02 | The U.S.A., As Represented By The Secretary, Department Of Health And Human Services | Antibody-drug conjugates specific for cd276 and uses thereof |
| IL296387B2 (en) | 2020-03-19 | 2024-08-01 | Avidity Biosciences Inc | Preparations and methods for the treatment of facial, back and arm muscle atrophy |
| MX2022011880A (es) | 2020-03-27 | 2022-10-20 | Avidity Biosciences Inc | Composiciones y metodos para tratar distrofia muscular. |
| CN115955980A (zh) | 2020-04-10 | 2023-04-11 | 思进公司 | 电荷可变接头 |
| CA3185040A1 (en) | 2020-05-26 | 2021-12-02 | Truebinding, Inc. | Methods of treating inflammatory diseases by blocking galectin-3 |
| CN111646999A (zh) * | 2020-07-30 | 2020-09-11 | 内江师范学院 | 一种吲哚啉羧酸类化合物及其制备方法 |
| WO2022082058A1 (en) * | 2020-10-16 | 2022-04-21 | Eleusis Therapeutics Us, Inc. | Method of treatment by tryptamine alkaloids |
| US20230391852A1 (en) | 2020-10-26 | 2023-12-07 | The U.S.A., As Represented By The Secretary, Department Of Health And Human Services | Single domain antibodies targeting sars coronavirus spike protein and uses thereof |
| WO2022098812A1 (en) | 2020-11-04 | 2022-05-12 | Keros Therapeutics, Inc. | Methods of treating iron overload |
| KR20230158006A (ko) | 2021-03-18 | 2023-11-17 | 씨젠 인크. | 생물학적 활성 화합물의 내재화된 접합체로부터의 선택적 약물 방출 |
| KR20230158005A (ko) | 2021-03-18 | 2023-11-17 | 씨젠 인크. | 생물학적 활성 화합물의 내재화된 접합체로부터의 선택적 약물 방출 |
| WO2022232612A1 (en) | 2021-04-29 | 2022-11-03 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Lassa virus-specific nanobodies and methods of their use |
| CN117500831A (zh) | 2021-06-09 | 2024-02-02 | 美国政府(由卫生和人类服务部的部长所代表) | 用于治疗实体瘤的靶向pd-l1的跨物种单结构域抗体 |
| WO2023288252A1 (en) | 2021-07-13 | 2023-01-19 | Truebinding, Inc. | Methods of preventing protein aggregation |
| JP2024530501A (ja) | 2021-08-13 | 2024-08-21 | イミュノジェン・インコーポレーテッド | 細胞毒性を有するベンゾジアゼピン誘導体を調製するための改良法 |
| KR20240055874A (ko) | 2021-09-16 | 2024-04-29 | 어비디티 바이오사이언시스 인크. | 안면견갑상완 근이영양증을 치료하는 조성물 및 방법 |
| KR20240095442A (ko) | 2021-11-03 | 2024-06-25 | 항저우 디에이씨 바이오테크 씨오, 엘티디 | 항체의 특이적 접합 |
| AU2022388722A1 (en) | 2021-11-09 | 2024-05-23 | Truebinding, Inc. | Methods of treating or inhibiting cardiovascular diseases |
| EP4519322A1 (en) | 2022-05-03 | 2025-03-12 | Genentech, Inc. | Anti-ly6e antibodies, immunoconjugates, and uses thereof |
| AU2023298568A1 (en) | 2022-06-30 | 2025-01-09 | Toray Industries, Inc. | Pharmaceutical composition for cancer treatment and/or prevention |
| EP4634227A1 (en) | 2022-12-13 | 2025-10-22 | Seagen Inc. | Site-specific engineered cysteine antibody drug conjugates |
| WO2024258995A2 (en) * | 2023-06-13 | 2024-12-19 | Delix Therapeutics, Inc. | Fused tetrahydroazepine psychoplastogens and uses thereof |
| WO2025019228A1 (en) | 2023-07-20 | 2025-01-23 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Fully human monoclonal antibodies and chimeric antigen receptors against cd276 for the treatment of solid tumors |
| EP4509142A1 (en) | 2023-08-16 | 2025-02-19 | Ona Therapeutics S.L. | Fgfr4 as target in cancer treatment |
| WO2025149947A1 (en) | 2024-01-12 | 2025-07-17 | Seagen Inc. | Antibody-drug conjugates |
| WO2025171238A1 (en) | 2024-02-07 | 2025-08-14 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Monoclonal antibodies that bind the juxta-membrane region of mesothelin and uses thereof |
Family Cites Families (108)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US860600A (en) * | 1900-05-07 | 1907-07-16 | U S Standard Voting Machine Company | Interlocking mechanism. |
| SU11248A1 (ru) | 1927-03-29 | 1929-09-30 | В.С. Григорьев | Способ очистки антрацена |
| US3453266A (en) | 1966-03-14 | 1969-07-01 | American Home Prod | 1,2,5-benzothiadiazepine 1,1-dioxides |
| US3506646A (en) | 1966-06-27 | 1970-04-14 | American Home Prod | Process for the preparation of 7h-pyrido (1,2-b)(1,2,5)benzothiadiazepine 5,5 - dioxides and pyrrolo(1,2-b)(1,2,5)benzothiadiazepine 5,5-dioxides |
| US3763183A (en) * | 1972-07-10 | 1973-10-02 | Sterling Drug Inc | 1,2,3,10,11,11a-hexahydro-5h-pyrrolo (2,1-c)(1,4)benzodiazepines |
| US3860600A (en) * | 1972-07-10 | 1975-01-14 | Sterling Drug Inc | Octahydropyrrido{8 2,1-c{9 {8 1,4{9 benzodiazepines |
| US3875162A (en) | 1973-07-26 | 1975-04-01 | Squibb & Sons Inc | Certain 6H-pyrimido{8 1,2-c{9 {8 1,3,5{9 benzothiadiaza compounds |
| US4003905A (en) | 1974-12-11 | 1977-01-18 | E. R. Squibb & Sons, Inc. | Diels-alder adducts of benzdiazepines |
| JPS57131791A (en) * | 1980-12-31 | 1982-08-14 | Fujisawa Pharmaceut Co Ltd | Benzodiazepine derivative and its preparation |
| US4444688A (en) | 1981-05-11 | 1984-04-24 | Ciba-Geigy Corporation | Imidazobenzothiadiazepines |
| US4678784A (en) | 1984-04-11 | 1987-07-07 | Mcneilab, Inc. | Method for the treatment of LHRH diseases and conditions |
| US4928908A (en) | 1987-06-12 | 1990-05-29 | Reiko Co., Ltd. | Balloon made of metal vapor deposited film |
| FR2633167B1 (fr) | 1988-06-27 | 1990-09-21 | Oreal | Ensemble applicateur d'un produit en poudre ou pateux notamment d'un produit cosmetique |
| JP2920385B2 (ja) | 1988-08-18 | 1999-07-19 | 武田薬品工業株式会社 | 1,2,5‐ベンゾチアジアゼピン誘導体,その製造法および用途 |
| GB8827305D0 (en) | 1988-11-23 | 1988-12-29 | British Bio Technology | Compounds |
| US5208020A (en) | 1989-10-25 | 1993-05-04 | Immunogen Inc. | Cytotoxic agents comprising maytansinoids and their therapeutic use |
| GB9015198D0 (en) | 1990-07-10 | 1990-08-29 | Brien Caroline J O | Binding substance |
| DE69233745D1 (de) | 1991-12-02 | 2008-10-23 | Cambridge Antibody Tech | Herstellung von Autoantikörpern auf Phagenoberflächen ausgehend von Antikörpersegmentbibliotheken |
| EP0911398B1 (en) * | 1991-12-06 | 2008-06-11 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Phosphorylation epitopes of Tau protein for the diagnosis and treatment of Alzheimer's disease |
| GB9205051D0 (en) * | 1992-03-09 | 1992-04-22 | Cancer Res Campaign Tech | Pyrrolobenzodiazepine derivatives,their preparation,and compositions containing them |
| CA2076465C (en) | 1992-03-25 | 2002-11-26 | Ravi V. J. Chari | Cell binding agent conjugates of analogues and derivatives of cc-1065 |
| US5639641A (en) | 1992-09-09 | 1997-06-17 | Immunogen Inc. | Resurfacing of rodent antibodies |
| US5455258A (en) | 1993-01-06 | 1995-10-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
| JPH08176070A (ja) | 1994-12-19 | 1996-07-09 | Mitsubishi Chem Corp | ジデプシド誘導体及びpi3キナーゼ阻害剤 |
| JPH08175990A (ja) | 1994-12-19 | 1996-07-09 | Mitsubishi Chem Corp | Pi3キナーゼ阻害剤とその製造法 |
| US5863949A (en) | 1995-03-08 | 1999-01-26 | Pfizer Inc | Arylsulfonylamino hydroxamic acid derivatives |
| FI973974A7 (fi) | 1995-04-20 | 1997-10-16 | Pfizer | Aryylisulfonyylihydroksaamihappojohdannaisia MMP- ja TNF-inhibiittorei na |
| GB9521987D0 (en) | 1995-10-26 | 1996-01-03 | Ludwig Inst Cancer Res | Phosphoinositide 3-kinase modulators |
| GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| DE69624081T2 (de) | 1995-12-20 | 2003-06-12 | Agouron Pharmaceuticals, Inc. | Matrix-metalloprotease Inhibitoren |
| BR9707495A (pt) | 1996-02-13 | 1999-07-27 | Zeneca Ltd | Derivado de quinazolina processo para a preparação do mesmo composição farmacêutica e processo para a produç o de um efeito antiangiogênico e/ou de redução de permeabilidade vascular em um animal de sangue quente |
| JP4464466B2 (ja) | 1996-03-05 | 2010-05-19 | アストラゼネカ・ユーケイ・リミテッド | 4―アニリノキナゾリン誘導体 |
| EP0818442A3 (en) | 1996-07-12 | 1998-12-30 | Pfizer Inc. | Cyclic sulphone derivatives as inhibitors of metalloproteinases and of the production of tumour necrosis factor |
| HUP9903014A3 (en) | 1996-07-18 | 2000-08-28 | Pfizer | Phosphinate derivatives having matrix metalloprotease inhibitor effect and medicaments containing the same |
| IL128189A0 (en) | 1996-08-23 | 1999-11-30 | Pfizer | Arylsulfonylamino hydroxamic acid derivatives |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| ES2224277T3 (es) | 1997-01-06 | 2005-03-01 | Pfizer Inc. | Derivados de sulfonas ciclicas. |
| PT977733E (pt) | 1997-02-03 | 2003-12-31 | Pfizer Prod Inc | Derivados de acido arilsulfonilamino-hidroxamico |
| JP2000507975A (ja) | 1997-02-07 | 2000-06-27 | ファイザー・インク | N−ヒドロキシ−β−スルホニルプロピオンアミド誘導体類及びそれらのマトリックスメタロプロテイナーゼ阻害薬としての使用 |
| IL131123A0 (en) | 1997-02-11 | 2001-01-28 | Pfizer | Arylsulfonyl hydroxamic acid derivatives |
| AU6111298A (en) | 1997-02-12 | 1998-09-08 | Samir M. Hanash | Protein markers for lung cancer and use thereof |
| WO1999006587A2 (en) | 1997-08-01 | 1999-02-11 | Morphosys Ag | Novel method and phage for the identification of nucleic acid sequences encoding members of a multimeric (poly)peptide complex |
| ES2216293T3 (es) | 1997-08-08 | 2004-10-16 | Pfizer Products Inc. | Derivados de acido ariloxiarilsulfonilamino-hidroxamico. |
| GB9725782D0 (en) | 1997-12-05 | 1998-02-04 | Pfizer Ltd | Therapeutic agents |
| GB9801690D0 (en) | 1998-01-27 | 1998-03-25 | Pfizer Ltd | Therapeutic agents |
| JP4462654B2 (ja) | 1998-03-26 | 2010-05-12 | ソニー株式会社 | 映像素材選択装置及び映像素材選択方法 |
| PA8469401A1 (es) | 1998-04-10 | 2000-05-24 | Pfizer Prod Inc | Derivados biciclicos del acido hidroxamico |
| PA8469501A1 (es) | 1998-04-10 | 2000-09-29 | Pfizer Prod Inc | Hidroxamidas del acido (4-arilsulfonilamino)-tetrahidropiran-4-carboxilico |
| US6156746A (en) | 1998-08-25 | 2000-12-05 | Bristol-Myers Squibb Company | 1,2,5-benzothiadiazepine-1,1-dioxides with n-2 imidazolylalkyl substituents |
| ATE320436T1 (de) * | 1998-08-27 | 2006-04-15 | Spirogen Ltd | Dimere pyrrolobenzodiazepine |
| GB9818731D0 (en) * | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Compounds |
| DK1004578T3 (da) | 1998-11-05 | 2004-06-28 | Pfizer Prod Inc | 5-oxo-pyrrolidin-2-carboxylsyrehydroxamidderivater |
| PL199802B1 (pl) | 1999-02-10 | 2008-10-31 | Astrazeneca Ab | Pochodne chinazoliny, sposoby ich wytwarzania, ich kompozycje farmaceutyczne i ich zastosowania |
| EP1676845B1 (en) | 1999-11-05 | 2008-06-11 | AstraZeneca AB | New quinazoline derivatives |
| DK1242401T3 (da) | 1999-11-24 | 2007-05-07 | Immunogen Inc | Cytotoksiske midler, der omfatter taxaner, og den terapeutiske anvendelse deraf |
| BRPI0117360B8 (pt) | 2000-02-15 | 2021-07-06 | Upjohn Co | inibidores de proteína de quinase de 2-indolinona de pirrol substituído, seus sais e composições farmacêuticas compreendendo os mesmos |
| JP2001247477A (ja) | 2000-03-03 | 2001-09-11 | Teikoku Hormone Mfg Co Ltd | 抗腫瘍剤 |
| US6608053B2 (en) | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| US6403588B1 (en) | 2000-04-27 | 2002-06-11 | Yamanouchi Pharmaceutical Co., Ltd. | Imidazopyridine derivatives |
| JP2003534384A (ja) | 2000-05-26 | 2003-11-18 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | 神経保護性ペプチド |
| ATE290882T1 (de) | 2001-01-16 | 2005-04-15 | Glaxo Group Ltd | Pharmazeutische mischung gegen krebs, die ein 4- chinazolinamin in kombination mit paclitaxel, carboplatin or vinorelbine enthält |
| US6441163B1 (en) | 2001-05-31 | 2002-08-27 | Immunogen, Inc. | Methods for preparation of cytotoxic conjugates of maytansinoids and cell binding agents |
| US20040242545A1 (en) | 2001-07-26 | 2004-12-02 | Santen Phamaceutical Co., Ltd. | Remedy for glaucoma comprising as the active ingredient compound having p13 kinase inhibitory effect |
| US6703414B2 (en) | 2001-09-14 | 2004-03-09 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Device and method for treating restenosis |
| WO2003034997A2 (en) | 2001-10-24 | 2003-05-01 | Iconix Pharmaceuticals, Inc. | Modulators of phosphoinositide 3-kinase |
| US6908932B2 (en) | 2001-10-24 | 2005-06-21 | Iconix Pharmaceuticals, Inc. | Modulators of phosphoinositide 3-kinase |
| MXPA04004064A (es) | 2001-10-30 | 2004-09-06 | Pharmacia Corp | Derivados heteroaromaticos de carboxamida para el tratramiento de la inflamacion. |
| US6716821B2 (en) | 2001-12-21 | 2004-04-06 | Immunogen Inc. | Cytotoxic agents bearing a reactive polyethylene glycol moiety, cytotoxic conjugates comprising polyethylene glycol linking groups, and methods of making and using the same |
| US6756397B2 (en) | 2002-04-05 | 2004-06-29 | Immunogen, Inc. | Prodrugs of CC-1065 analogs |
| GB0209467D0 (en) | 2002-04-25 | 2002-06-05 | Astrazeneca Ab | Chemical compounds |
| US7538195B2 (en) | 2002-06-14 | 2009-05-26 | Immunogen Inc. | Anti-IGF-I receptor antibody |
| US20040092561A1 (en) | 2002-11-07 | 2004-05-13 | Thomas Ruckle | Azolidinone-vinyl fused -benzene derivatives |
| CA2493843C (en) | 2002-07-10 | 2012-04-17 | Applied Research Systems Ars Holding N.V. | Azolidinone-vinyl fused-benzene derivatives |
| CA2489779A1 (en) | 2002-07-10 | 2004-01-22 | Applied Research Systems Ars Holding N.V. | Use of compounds for increasing spermatozoa motility |
| WO2004013093A2 (en) | 2002-08-02 | 2004-02-12 | Immunogen, Inc. | Cytotoxic agents containing novel potent taxanes and their therapeutic use |
| ATE499116T1 (de) | 2002-08-16 | 2011-03-15 | Immunogen Inc | Vernetzer mit hoher reaktivität und löslichkeit und ihre verwendung bei der herstellung von konjugaten für die gezielte abgabe von kleinmolekularen arzneimitteln |
| WO2004017950A2 (en) | 2002-08-22 | 2004-03-04 | Piramed Limited | Phosphadidylinositol 3,5-biphosphate inhibitors as anti-viral agents |
| FR2850654A1 (fr) | 2003-02-03 | 2004-08-06 | Servier Lab | Nouveaux derives d'azepines tricycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CA2520898C (en) * | 2003-03-31 | 2009-10-20 | Council Of Scientific And Industrial Research | Non-cross-linking pyrrolo(2,1-c)(1,4)benzodiazepines as potential antitumour agents and process thereof |
| RU2338747C2 (ru) * | 2003-03-31 | 2008-11-20 | Каунсил Оф Сайентифик Энд Индастриал Рисерч | ДИМЕРЫ ПИРРОЛО [2, 1-c][1, 4] БЕНЗОДИАЗЕПИНА В КАЧЕСТВЕ ПРОТИВООПУХОЛЕВЫХ СРЕДСТВ И СПОСОБ ИХ ПОЛУЧЕНИЯ |
| RU2314309C2 (ru) * | 2003-03-31 | 2008-01-10 | Каунсил Оф Сайентифик Энд Индастриал Рисерч | Пирроло [2.1-c][1.4] бензодиазепины, способ их получения и фармацевтическая композиция на их основе |
| WO2004087716A1 (en) | 2003-03-31 | 2004-10-14 | Council Of Scientific And Industrial Research | Pyrrolo[(2,1-c)(1,4) benzodiazepines dimers as antitumour agents and process thereof |
| US8088387B2 (en) | 2003-10-10 | 2012-01-03 | Immunogen Inc. | Method of targeting specific cell populations using cell-binding agent maytansinoid conjugates linked via a non-cleavable linker, said conjugates, and methods of making said conjugates |
| US7276497B2 (en) | 2003-05-20 | 2007-10-02 | Immunogen Inc. | Cytotoxic agents comprising new maytansinoids |
| EP1675857B1 (en) * | 2003-10-22 | 2011-07-13 | THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES | Pyrrolobenzodiazepine derivatives, compositions comprising the same and methods related thereto |
| GB0404578D0 (en) * | 2004-03-01 | 2004-04-07 | Spirogen Ltd | Pyrrolobenzodiazepines |
| WO2005085260A1 (en) | 2004-03-09 | 2005-09-15 | Spirogen Limited | Pyrrolobenzodiazepines |
| GB0410725D0 (en) * | 2004-05-13 | 2004-06-16 | Spirogen Ltd | Pyrrolobenzodiazepine therapeutic agents |
| BRPI0510883B8 (pt) | 2004-06-01 | 2021-05-25 | Genentech Inc | composto conjugado de droga e anticorpo, composição farmacêutica, método de fabricação de composto conjugado de droga e anticorpo e usos de uma formulação, de um conjugado de droga e anticorpo e um agente quimioterapêutico e de uma combinação |
| GB0423653D0 (en) | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| WO2006065533A2 (en) | 2004-11-29 | 2006-06-22 | Seattle Genetics, Inc. | Engineered antibodies and immunoconjugates |
| ITRM20050416A1 (it) | 2005-08-03 | 2007-02-04 | Uni Degli Studi Di Roma Tor Vergata | Derivati delle benzodiazepine e loro usi in campo medico. |
| US8637664B2 (en) | 2005-10-05 | 2014-01-28 | Spirogen Sarl | Alkyl 4- [4- (5-oxo-2,3,5, 11a-tetrahydo-5H-pyrrolo [2, 1-c] [1,4] benzodiazepine-8-yloxy)-butyrylamino]-1H-pyrrole-2-carboxylate derivatives and related compounds for the treatment of a proliferative disease |
| GB0520657D0 (en) | 2005-10-11 | 2005-11-16 | Ludwig Inst Cancer Res | Pharmaceutical compounds |
| SI1813614T1 (sl) * | 2006-01-25 | 2012-01-31 | Sanofi 174 | Citotoksična sredstva, ki obsegajo nove tomajmicinske derivate |
| JP2009526778A (ja) * | 2006-02-13 | 2009-07-23 | カウンシル オブ サイエンティフィク アンド インダストリアル リサーチ | 抗腫瘍剤としてのビス−ピロロ[2,1−c][1,4]ベンゾジアゼピン−アントラキノン抱合体およびその製造方法 |
| EP1864682A1 (en) | 2006-06-09 | 2007-12-12 | Sanofi-Aventis | Leptomycin derivatives |
| ES2435779T3 (es) | 2007-07-19 | 2013-12-23 | Sanofi | Agentes citotóxicos que comprenden nuevos derivados de tomaimicina y su uso terapéutico |
| EP2188297B1 (en) | 2007-08-01 | 2012-02-01 | Council of Scientific & Industrial Research | Pyrrolo [2,1-c][1, 4] benzodiazepine-glycoside prodrugs useful as a selective anti tumor agent |
| GB0819095D0 (en) | 2008-10-17 | 2008-11-26 | Spirogen Ltd | Pyrrolobenzodiazepines |
| CN105198908B (zh) | 2009-02-05 | 2019-12-24 | 伊缪诺金公司 | 新型苯并二氮杂*衍生物 |
| KR20120080611A (ko) | 2009-10-06 | 2012-07-17 | 이뮤노젠 아이엔씨 | 효능 있는 접합체 및 친수성 링커 |
| KR20170085143A (ko) | 2010-02-24 | 2017-07-21 | 이뮤노젠 아이엔씨 | 엽산염 수용체 1 항체와 면역접합체 및 이들의 용도 |
| CN102933236B (zh) * | 2010-04-15 | 2014-10-08 | 斯皮罗根有限公司 | 吡咯并苯二氮卓类及其结合物 |
| CN103068405A (zh) | 2010-04-15 | 2013-04-24 | 西雅图基因公司 | 靶向吡咯并苯并二氮杂卓结合物 |
| ES2623057T3 (es) | 2010-04-15 | 2017-07-10 | Medimmune Limited | Pirrolobenzodiazepinas usadas para tratar enfermedades proliferativas |
| PT2675480T (pt) | 2011-02-15 | 2019-04-15 | Immunogen Inc | Métodos para preparação de conjugados |
| HK1211208A1 (zh) | 2012-08-22 | 2016-05-20 | Immunogen, Inc. | 細胞毒性苯並二氮呯衍生物 |
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