KR102660070B1 - 세포독성 벤조다이아제핀 유도체의 제조 방법 - Google Patents

세포독성 벤조다이아제핀 유도체의 제조 방법 Download PDF

Info

Publication number
KR102660070B1
KR102660070B1 KR1020187005041A KR20187005041A KR102660070B1 KR 102660070 B1 KR102660070 B1 KR 102660070B1 KR 1020187005041 A KR1020187005041 A KR 1020187005041A KR 20187005041 A KR20187005041 A KR 20187005041A KR 102660070 B1 KR102660070 B1 KR 102660070B1
Authority
KR
South Korea
Prior art keywords
formula
compound
delete delete
reacting
reagent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
KR1020187005041A
Other languages
English (en)
Korean (ko)
Other versions
KR20180038461A (ko
Inventor
보두앵 제라드
마나미 시즈카
마이클 루이스 밀러
리차드 에이. 실바
Original Assignee
이뮤노젠 아이엔씨
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 이뮤노젠 아이엔씨 filed Critical 이뮤노젠 아이엔씨
Priority to KR1020247012991A priority Critical patent/KR20240055903A/ko
Publication of KR20180038461A publication Critical patent/KR20180038461A/ko
Application granted granted Critical
Publication of KR102660070B1 publication Critical patent/KR102660070B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D519/00Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06Dipeptides
    • C07K5/06008Dipeptides with the first amino acid being neutral
    • C07K5/06017Dipeptides with the first amino acid being neutral and aliphatic
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A61K31/55131,4-Benzodiazepines, e.g. diazepam or clozapine
    • A61K31/55171,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63Esters of sulfonic acids
    • C07C309/64Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
    • C07F7/1872Preparation; Treatments not provided for in C07F7/20
    • C07F7/188Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08Tripeptides
    • C07K5/0802Tripeptides with the first amino acid being neutral
    • C07K5/0804Tripeptides with the first amino acid being neutral and aliphatic
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pyridine Compounds (AREA)
  • Medicinal Preparation (AREA)
KR1020187005041A 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법 Active KR102660070B1 (ko)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020247012991A KR20240055903A (ko) 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201562195023P 2015-07-21 2015-07-21
US62/195,023 2015-07-21
US201662327973P 2016-04-26 2016-04-26
US62/327,973 2016-04-26
PCT/US2016/043406 WO2017015496A1 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives

Related Child Applications (1)

Application Number Title Priority Date Filing Date
KR1020247012991A Division KR20240055903A (ko) 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법

Publications (2)

Publication Number Publication Date
KR20180038461A KR20180038461A (ko) 2018-04-16
KR102660070B1 true KR102660070B1 (ko) 2024-04-24

Family

ID=56557925

Family Applications (5)

Application Number Title Priority Date Filing Date
KR1020247012991A Withdrawn KR20240055903A (ko) 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법
KR1020247012816A Withdrawn KR20240055894A (ko) 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법
KR1020187003181A Active KR102659706B1 (ko) 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법
KR1020187005040A Withdrawn KR20180038460A (ko) 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법
KR1020187005041A Active KR102660070B1 (ko) 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법

Family Applications Before (4)

Application Number Title Priority Date Filing Date
KR1020247012991A Withdrawn KR20240055903A (ko) 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법
KR1020247012816A Withdrawn KR20240055894A (ko) 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법
KR1020187003181A Active KR102659706B1 (ko) 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법
KR1020187005040A Withdrawn KR20180038460A (ko) 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법

Country Status (23)

Country Link
US (11) US9873708B2 (enExample)
EP (7) EP3653628B1 (enExample)
JP (8) JP6858745B2 (enExample)
KR (5) KR20240055903A (enExample)
CN (5) CN108026103B (enExample)
AU (7) AU2016297608B2 (enExample)
CA (4) CA2992082A1 (enExample)
CY (2) CY1122553T1 (enExample)
DK (2) DK3325483T3 (enExample)
ES (4) ES2959741T3 (enExample)
HK (1) HK1252322A1 (enExample)
HR (1) HRP20201479T1 (enExample)
HU (1) HUE051541T2 (enExample)
IL (10) IL286788B2 (enExample)
LT (2) LT3325483T (enExample)
PL (2) PL3325482T3 (enExample)
PT (2) PT3325482T (enExample)
RS (2) RS59806B1 (enExample)
RU (3) RU2018105752A (enExample)
SG (2) SG10202009354SA (enExample)
SI (2) SI3325482T1 (enExample)
SM (2) SMT202000004T1 (enExample)
WO (3) WO2017015502A1 (enExample)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3653628B1 (en) 2015-07-21 2022-09-14 ImmunoGen, Inc. Methods of preparing cytotoxic benzodiazepine derivatives
KR102609698B1 (ko) 2016-03-22 2023-12-04 에베 그룹 에. 탈너 게엠베하 기판을 결합하기 위한 방법 및 장치
CA3041254A1 (en) 2016-10-19 2018-04-26 Invenra Inc. Antibody constructs
BR112019013107A2 (pt) 2016-12-22 2019-12-17 Univ Degli Studi Magna Graecia Catanzaro anticorpos, molécula de ligação, receptor de antígeno quimérico, vetor de expressão, composição farmacêutica, linfócito, ácido nucleico, célula de hibridoma, método para a produção do anticorpo monoclonal e usos
IL287405B (en) * 2017-01-25 2022-07-01 Immunogen Inc Methods of preparing cytotoxic benzodiazepine derivatives
WO2019234136A1 (en) 2018-06-05 2019-12-12 King's College London Btnl3/8 targeting constructs for delivery of payloads to the gastrointestinal system
MA54225A (fr) * 2018-11-12 2021-09-22 Immunogen Inc Procédés de préparation de dérivés de benzodiazépine cytotoxiques
WO2020102051A1 (en) 2018-11-12 2020-05-22 Immunogen, Inc. Methods of preparing cytotoxic benzodiazepine derivatives
CN113661172A (zh) * 2019-03-29 2021-11-16 伊缪诺金公司 用于抑制异常细胞生长或治疗增生性疾病的细胞毒性双苯并二氮杂䓬衍生物及其与细胞结合剂的缀合物
EP4548932A1 (en) 2022-06-30 2025-05-07 Toray Industries, Inc. Pharmaceutical composition for treating and/or preventing cancer

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012128868A1 (en) 2011-02-15 2012-09-27 Immunogen, Inc. Cytotoxic benzodiazepine derivatives

Family Cites Families (62)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US4678784A (en) 1984-04-11 1987-07-07 Mcneilab, Inc. Method for the treatment of LHRH diseases and conditions
US5208020A (en) 1989-10-25 1993-05-04 Immunogen Inc. Cytotoxic agents comprising maytansinoids and their therapeutic use
GB9205051D0 (en) 1992-03-09 1992-04-22 Cancer Res Campaign Tech Pyrrolobenzodiazepine derivatives,their preparation,and compositions containing them
ES2149768T3 (es) 1992-03-25 2000-11-16 Immunogen Inc Conjugados de agentes enlazantes de celulas derivados de cc-1065.
DK1413582T3 (da) 1998-08-27 2006-07-17 Spirogen Ltd Dimere pyrrolobenzodiazepiner
GB9818731D0 (en) 1998-08-27 1998-10-21 Univ Portsmouth Compounds
CA2388063C (en) 1999-11-24 2010-06-08 Immunogen, Inc. Cytotoxic agents comprising taxanes and their therapeutic use
US6548042B2 (en) * 2000-08-07 2003-04-15 Arstad Erik Bis-phosphonate compounds
UA75093C2 (en) * 2000-10-06 2006-03-15 Dimensional Pharm Inc Aminopyridinyl-,aminoguanidinyl-, and alkoxyguanidinesubstituted phenylsubstituted phenylacetamides as protease inhibitors
US6441163B1 (en) 2001-05-31 2002-08-27 Immunogen, Inc. Methods for preparation of cytotoxic conjugates of maytansinoids and cell binding agents
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
MXPA05001390A (es) 2002-08-02 2005-07-29 Immunogen Inc Agentes citotoxicos que contienen taxanos potentes novedosos y su uso terapeutico.
ES2361739T3 (es) 2002-08-16 2011-06-21 Immunogen, Inc. Reticulantes con elevada reactividad y solubilidad y su uso en la preparación de conjugados para el suministro dirigido de fármacos de molécula pequeña.
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
EP1608664B1 (en) 2003-03-31 2009-01-28 Council of Scientific and Industrial Research Non-cross-linking pyrrolo[2,1-c][1,4]benzodiazepines as potential antitumour agents and process thereof
ATE413407T1 (de) 2003-03-31 2008-11-15 Council Scient Ind Res Pyrrolo(2,1-c)(1,4)benzodiazepin-dimere als antitumormittel und verfahren dafür
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
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
ATE516288T1 (de) 2003-10-22 2011-07-15 Us Gov Health & Human Serv Pyrrolobenzodiazepinderivate, zusammensetzungen, die diese enthalten, und damit in zusammenhang stehende verfahren
GB2424883B (en) 2003-12-31 2008-10-22 Council Scient Ind Res Process for preparing pyrrolo[2, 1-c] [1,4] benzodiazepine hybrids
ES2398975T3 (es) * 2004-03-01 2013-03-25 Spirogen Sàrl Derivados de 11-hidroxi-5H-pirrolo[2,1-c][1,4]benzodiazepin-5-ona como intermedios clave para la preparación de pirrolobenzodiazepinas sustituidas en C2
GB0404578D0 (en) 2004-03-01 2004-04-07 Spirogen Ltd Pyrrolobenzodiazepines
GB0410725D0 (en) 2004-05-13 2004-06-16 Spirogen Ltd Pyrrolobenzodiazepine therapeutic agents
GB0412492D0 (en) * 2004-06-04 2004-07-07 Sterix Ltd Compound
GB0508084D0 (en) * 2005-04-21 2005-06-01 Spirogen Ltd Pyrrolobenzodiazepines
SI1879901T1 (sl) 2005-04-21 2010-04-30 Spirogen Ltd Pirolobenzodiazepini
ATE427949T1 (de) 2005-10-05 2009-04-15 Spirogen Ltd 4-a4-(5-oxo-2,3,5,11a-tetrahydro-5h-pyrrolo a2, 1-cua1,4ubenzodiazepin-8-yloxy)-butyrylaminou-1 - pyrrol-2-carbonsaurealkylesterderivate und verwandte verbindung zur behandlung einer proliferativen erkrankung
DE602006015861D1 (de) * 2005-12-21 2010-09-09 Abbott Lab Antivirale verbindungen
DK1813614T3 (da) 2006-01-25 2012-01-23 Sanofi Sa Cytotoksiske midler, der omfatter nye tomaymycinderivater
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
HRP20140172T1 (hr) 2006-05-30 2014-03-28 Genentech, Inc. Protutijela i imunokonjugati kao i njihove uporabe
SI2019104T1 (sl) 2007-07-19 2013-12-31 Sanofi Citotoksična sredstva, ki obsegajo nove tomaimicinske derivate, in njihova terapevtska uporaba
ATE543826T1 (de) 2007-08-01 2012-02-15 Council Scient Ind Res Als selektive antitumormittel geeignete pyrroloä2,1-cüä1,4übenzodiazepinglycosid-prodru s
MX2010011808A (es) 2008-04-30 2011-03-04 Immunogen Inc Conjugados potentes y enlazadores hidrofilicos.
CN104524590B (zh) 2008-04-30 2019-06-21 伊缪诺金公司 交联剂和它们的用途
GB0819095D0 (en) 2008-10-17 2008-11-26 Spirogen Ltd Pyrrolobenzodiazepines
GB0822260D0 (en) * 2008-12-05 2009-01-14 Merten Christoph Assay
US8637558B2 (en) * 2008-12-30 2014-01-28 Industry-Academic Cooperation Foundation, Chosun University Thiazolidinedione derivative and use thereof
EP3100745B1 (en) * 2009-02-05 2018-04-18 Immunogen, Inc. Novel benzodiazepine derivatives
EP2486023A4 (en) 2009-10-06 2014-05-07 Immunogen Inc EFFICIENT CONJUGATES AND HYDROPHILIC BINDER
US8314250B2 (en) * 2009-11-24 2012-11-20 Hoffmann-La Roche Inc. Sultam derivatives
WO2011071078A1 (ja) * 2009-12-08 2011-06-16 国立大学法人岐阜大学 芳香族化合物、並びに、それを用いたオリゴヌクレオチド誘導体合成用修飾担体、オリゴヌクレオチド誘導体及びオリゴヌクレオチド構築物
US8962279B2 (en) * 2009-12-30 2015-02-24 Intel Corporation Solid-phase chelators and electronic biosensors
RS56232B1 (sr) * 2010-02-11 2017-11-30 Celgene Corp Derivati arilmetoksi izoindolina i kompozicije koje ih obuhvataju i postupci njihove primene
KR20230044026A (ko) 2010-02-24 2023-03-31 이뮤노젠 아이엔씨 엽산염 수용체 1 항체와 면역접합체 및 이들의 용도
NZ602932A (en) * 2010-04-15 2014-08-29 Seattle Genetics Inc Targeted pyrrolobenzodiazapine conjugates
BR112012026213B1 (pt) 2010-04-15 2021-12-28 Medimmune Limited Compostos de pirrolobenzodiazepinas, conjugado das mesmas, composição farmacêutica compreendendo o conjugado e uso do mesmo para o tratamento de uma doença proliferativa
MX368648B (es) 2010-04-15 2019-10-09 Seattle Genetics Inc Pirrolobenzodiazepinas usadas para tratar enfermedades proliferativas.
CN102234253B (zh) * 2011-06-02 2013-07-03 重庆莱美药业股份有限公司 一种制备非布索坦中间体的方法
WO2014031566A1 (en) * 2012-08-22 2014-02-27 Immunogen, Inc. Cytotoxic benzodiazepine derivatives
JP6694811B2 (ja) 2013-10-04 2020-05-20 ノバルティス アーゲー RNA干渉に使用するためのRNAi剤用の3’末端キャップ
CN104628772A (zh) 2013-11-07 2015-05-20 四川恒康发展有限责任公司 一种抗肿瘤前药及其激活剂、组合物和应用
CN103664896B (zh) * 2013-11-25 2016-03-02 济南精合医药科技有限公司 一种抗肿瘤分子靶向药物克里唑替尼的合成工艺方法
TW201609152A (zh) * 2014-09-03 2016-03-16 免疫原公司 包含細胞結合劑及細胞毒性劑之偶聯物
TW201613930A (en) 2014-09-03 2016-04-16 Immunogen Inc Cytotoxic benzodiazepine derivatives
TW202417447A (zh) 2014-09-03 2024-05-01 美商免疫原公司 細胞毒性苯并二氮呯衍生物
EP3653628B1 (en) 2015-07-21 2022-09-14 ImmunoGen, Inc. Methods of preparing cytotoxic benzodiazepine derivatives
FI3380525T3 (fi) * 2015-11-25 2024-01-30 Immunogen Inc Lääkeformulaatioita ja niiden käyttömenetelmiä

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012128868A1 (en) 2011-02-15 2012-09-27 Immunogen, Inc. Cytotoxic benzodiazepine derivatives
US20130302359A1 (en) 2011-02-15 2013-11-14 Wei Li Cytotoxic benzodiazepine derivatives

Also Published As

Publication number Publication date
US10370389B2 (en) 2019-08-06
CA2991326A1 (en) 2017-01-26
US11420982B2 (en) 2022-08-23
ES2959741T3 (es) 2024-02-28
AU2016297087B2 (en) 2021-02-18
EP3778602A1 (en) 2021-02-17
RU2018105609A3 (enExample) 2020-04-30
AU2021203148B2 (en) 2023-01-12
IL256854A (en) 2018-03-29
EP4286387A3 (en) 2024-02-21
IL294651A (en) 2022-09-01
SG10202106529XA (en) 2021-07-29
KR20240055894A (ko) 2024-04-29
US10899775B2 (en) 2021-01-26
US20190010169A1 (en) 2019-01-10
US20210171546A1 (en) 2021-06-10
JP6858745B2 (ja) 2021-04-14
US9890179B2 (en) 2018-02-13
AU2016297608B2 (en) 2021-02-18
US20170050986A1 (en) 2017-02-23
US20210171547A1 (en) 2021-06-10
JP7334228B2 (ja) 2023-08-28
JP2018524387A (ja) 2018-08-30
JP2023162264A (ja) 2023-11-08
EP4286387A2 (en) 2023-12-06
KR20180038461A (ko) 2018-04-16
IL283355B (en) 2022-08-01
JP2018526340A (ja) 2018-09-13
PL3325483T3 (pl) 2020-05-18
AU2021202403B2 (en) 2022-12-08
DK3325482T3 (da) 2020-09-28
US20170050985A1 (en) 2017-02-23
US20190112320A1 (en) 2019-04-18
IL276630A (en) 2020-09-30
JP6787995B2 (ja) 2020-11-18
CN108026103B (zh) 2021-04-16
IL305989A (en) 2023-11-01
RU2018105756A (ru) 2019-08-21
CN108290895A (zh) 2018-07-17
EP3778602B1 (en) 2023-07-12
AU2016297087A1 (en) 2018-02-08
JP7337114B2 (ja) 2023-09-01
KR20180038460A (ko) 2018-04-16
RS59806B1 (sr) 2020-02-28
RU2018105752A (ru) 2019-08-21
CN108055844A (zh) 2018-05-18
SMT202000004T1 (it) 2020-03-13
CA2992082A1 (en) 2017-01-26
CA2991305A1 (en) 2017-01-26
AU2021202403A1 (en) 2021-05-20
KR20180026741A (ko) 2018-03-13
US20180201626A1 (en) 2018-07-19
HRP20201479T1 (hr) 2020-12-11
ES2933376T3 (es) 2023-02-06
CN108026103A (zh) 2018-05-11
US10787463B2 (en) 2020-09-29
IL276631A (en) 2020-09-30
EP3325482B1 (en) 2020-06-24
EP3325483B1 (en) 2019-10-02
HK1252322A1 (zh) 2019-05-24
IL286788B2 (en) 2024-01-01
IL294651B1 (en) 2023-10-01
JP2022046542A (ja) 2022-03-23
CA2991305C (en) 2024-03-12
EP3653628B1 (en) 2022-09-14
WO2017015495A1 (en) 2017-01-26
RU2018105752A3 (enExample) 2019-12-30
WO2017015502A8 (en) 2017-03-02
EP3325485B1 (en) 2020-04-08
US10392407B2 (en) 2019-08-27
US20190389883A1 (en) 2019-12-26
PT3325482T (pt) 2020-09-24
SMT202000506T1 (it) 2020-11-10
RU2727151C2 (ru) 2020-07-21
SI3325482T1 (sl) 2020-11-30
IL283355A (en) 2021-07-29
KR102659706B1 (ko) 2024-04-23
CA3227588A1 (en) 2017-01-26
US9873708B2 (en) 2018-01-23
IL256861A (en) 2018-03-29
HUE051541T2 (hu) 2021-03-01
PT3325483T (pt) 2020-01-15
WO2017015496A1 (en) 2017-01-26
RS60840B1 (sr) 2020-10-30
LT3325482T (lt) 2020-11-25
JP2021100959A (ja) 2021-07-08
HK1252321A1 (en) 2019-05-24
EP3653628A1 (en) 2020-05-20
EP4163284A1 (en) 2023-04-12
IL276630B (en) 2021-06-30
IL256861B (en) 2020-08-31
KR20240055903A (ko) 2024-04-29
RU2746322C2 (ru) 2021-04-12
CY1122553T1 (el) 2021-01-27
AU2023201339A1 (en) 2023-04-06
EP3325482A1 (en) 2018-05-30
US20230257400A1 (en) 2023-08-17
AU2016297608A1 (en) 2018-02-08
LT3325483T (lt) 2020-01-27
IL256860B (en) 2020-08-31
EP3325485A1 (en) 2018-05-30
US20170051011A1 (en) 2017-02-23
CN113004288A (zh) 2021-06-22
US20200017526A1 (en) 2020-01-16
SG10202009354SA (en) 2020-11-27
RU2018105609A (ru) 2019-08-26
AU2023202221A1 (en) 2023-05-04
US10081640B2 (en) 2018-09-25
JP2018522018A (ja) 2018-08-09
JP2021035958A (ja) 2021-03-04
JP2023166434A (ja) 2023-11-21
ES2764548T3 (es) 2020-06-03
IL276631B (en) 2021-10-31
SI3325483T1 (sl) 2020-03-31
JP6995178B2 (ja) 2022-02-21
AU2021203148A1 (en) 2021-06-10
IL286788A (en) 2021-10-31
EP3325483A1 (en) 2018-05-30
WO2017015502A1 (en) 2017-01-26
CN108290895B (zh) 2021-03-19
IL286788B1 (en) 2023-09-01
HK1252323A1 (en) 2019-05-24
DK3325483T3 (da) 2020-01-20
CY1123390T1 (el) 2022-03-24
ES2820358T3 (es) 2021-04-20
AU2016297607A1 (en) 2018-02-08
RU2018105756A3 (enExample) 2019-12-23
IL294651B2 (en) 2024-02-01
IL256860A (en) 2018-03-29
IL305279A (en) 2023-10-01
CN113087763A (zh) 2021-07-09
PL3325482T3 (pl) 2021-01-11

Similar Documents

Publication Publication Date Title
KR102660070B1 (ko) 세포독성 벤조다이아제핀 유도체의 제조 방법
HK40088821A (en) Methods of preparing cytotoxic benzodiazepine derivatives
HK40029973A (en) Methods of preparing cytotoxic benzodiazepine derivatives
HK40029973B (en) Methods of preparing cytotoxic benzodiazepine derivatives
HK1252323B (en) Methods of preparing cytotoxic benzodiazepine derivatives

Legal Events

Date Code Title Description
PA0105 International application

St.27 status event code: A-0-1-A10-A15-nap-PA0105

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

E13-X000 Pre-grant limitation requested

St.27 status event code: A-2-3-E10-E13-lim-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

St.27 status event code: A-1-2-D10-D22-exm-PE0701

PA0104 Divisional application for international application

St.27 status event code: A-0-1-A10-A17-div-PA0104

St.27 status event code: A-0-1-A10-A16-div-PA0104

PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U12-oth-PR1002

Fee payment year number: 1

PG1601 Publication of registration

St.27 status event code: A-4-4-Q10-Q13-nap-PG1601

R18 Changes to party contact information recorded

Free format text: ST27 STATUS EVENT CODE: A-5-5-R10-R18-OTH-X000 (AS PROVIDED BY THE NATIONAL OFFICE)

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000