KR102659706B1 - 세포독성 벤조다이아제핀 유도체의 제조 방법 - Google Patents

세포독성 벤조다이아제핀 유도체의 제조 방법 Download PDF

Info

Publication number
KR102659706B1
KR102659706B1 KR1020187003181A KR20187003181A KR102659706B1 KR 102659706 B1 KR102659706 B1 KR 102659706B1 KR 1020187003181 A KR1020187003181 A KR 1020187003181A KR 20187003181 A KR20187003181 A KR 20187003181A KR 102659706 B1 KR102659706 B1 KR 102659706B1
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
KR1020187003181A
Other languages
English (en)
Korean (ko)
Other versions
KR20180026741A (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 KR1020247012816A priority Critical patent/KR20240055894A/ko
Publication of KR20180026741A publication Critical patent/KR20180026741A/ko
Application granted granted Critical
Publication of KR102659706B1 publication Critical patent/KR102659706B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28—Preparation 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic 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
    • A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
    • A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic 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
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design 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)
  • Medicinal Preparation (AREA)
  • Pyridine Compounds (AREA)
KR1020187003181A 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법 Active KR102659706B1 (ko)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020247012816A KR20240055894A (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/US2016/043414 WO2017015502A1 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives

Related Child Applications (1)

Application Number Title Priority Date Filing Date
KR1020247012816A Division KR20240055894A (ko) 2015-07-21 2016-07-21 세포독성 벤조다이아제핀 유도체의 제조 방법

Publications (2)

Publication Number Publication Date
KR20180026741A KR20180026741A (ko) 2018-03-13
KR102659706B1 true KR102659706B1 (ko) 2024-04-23

Family

ID=56557925

Family Applications (5)

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

Family Applications After (4)

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

Country Status (23)

Country Link
US (11) US9890179B2 (enExample)
EP (7) EP3325483B1 (enExample)
JP (8) JP6787995B2 (enExample)
KR (5) KR102659706B1 (enExample)
CN (5) CN108026103B (enExample)
AU (7) AU2016297607A1 (enExample)
CA (4) CA2991305C (enExample)
CY (2) CY1122553T1 (enExample)
DK (2) DK3325482T3 (enExample)
ES (4) ES2764548T3 (enExample)
HK (1) HK1252322A1 (enExample)
HR (1) HRP20201479T1 (enExample)
HU (1) HUE051541T2 (enExample)
IL (10) IL286788B2 (enExample)
LT (2) LT3325483T (enExample)
PL (2) PL3325483T3 (enExample)
PT (2) PT3325483T (enExample)
RS (2) RS59806B1 (enExample)
RU (3) RU2746322C2 (enExample)
SG (2) SG10202106529XA (enExample)
SI (2) SI3325483T1 (enExample)
SM (2) SMT202000506T1 (enExample)
WO (3) WO2017015495A1 (enExample)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3325483B1 (en) 2015-07-21 2019-10-02 ImmunoGen, Inc. Methods of preparing cytotoxic benzodiazepine derivatives
EP4036956A1 (de) 2016-03-22 2022-08-03 EV Group E. Thallner GmbH Vorrichtung zum bonden von substraten
KR20250044934A (ko) 2016-10-19 2025-04-01 인벤라 인코포레이티드 항체 구조물
EP3559039A1 (en) 2016-12-22 2019-10-30 Università Degli Studi Magna Graecia Catanzaro A monoclonal antibody targeting a unique sialoglycosilated cancer-associated epitope of cd43
HRP20230002T1 (hr) 2017-01-25 2023-02-17 Immunogen, Inc. Postupci pripreme citotoksičnih derivata benzodiazepina
CN120795120A (zh) 2018-06-05 2025-10-17 伦敦大学国王学院 向胃肠系统递送酬载的btnl3/8导引构建体
CA3119358A1 (en) * 2018-11-12 2020-05-22 Immunogen, Inc. Methods of preparing cytotoxic benzodiazepine derivatives
IL283047B2 (en) * 2018-11-12 2024-04-01 Immunogen Inc Methods for preparing cytotoxic benzodiazepine derivatives
TW202102506A (zh) * 2019-03-29 2021-01-16 美商伊繆諾金公司 苯二氮平衍生物
CN119486758A (zh) 2022-06-30 2025-02-18 东丽株式会社 癌的治疗和/或预防用药物组合物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010064141A1 (en) 2008-12-05 2010-06-10 Christoph Merten Assay
WO2010091150A1 (en) 2009-02-05 2010-08-12 Immunogen, Inc. Novel benzodiazepine derivatives
US20110159481A1 (en) 2009-12-30 2011-06-30 Liu David J Solid-phase chelators and electronic biosensors
WO2012128868A1 (en) 2011-02-15 2012-09-27 Immunogen, Inc. Cytotoxic benzodiazepine derivatives

Family Cites Families (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3860600A (en) 1972-07-10 1975-01-14 Sterling Drug Inc Octahydropyrrido{8 2,1-c{9 {8 1,4{9 benzodiazepines
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
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
DE69231123T2 (de) 1992-03-25 2001-02-15 Immunogen Inc Konjugaten von Zell-bindender Mittel und Derivaten von CC-1065
ATE240334T1 (de) 1998-08-27 2003-05-15 Spirogen Ltd Pyrrolobenzodiazepine
GB9818731D0 (en) 1998-08-27 1998-10-21 Univ Portsmouth Compounds
JP2003514903A (ja) 1999-11-24 2003-04-22 イムノージェン インコーポレーテッド タキサンを含有する細胞傷害薬とその治療への利用
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
JP2005539009A (ja) 2002-08-02 2005-12-22 イミュノジェン・インコーポレーテッド 新規の効力のあるタキサンを含む細胞毒性物質、および、それらの治療用途
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
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
EP1608663B1 (en) 2003-03-31 2008-11-05 Council of Scientific and Industrial Research Pyrrolo (2,1-c)(1,4) benzodiazepines dimers as 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
DE60326060D1 (de) 2003-03-31 2009-03-19 Council Scient Ind Res Nichtvernetzende pyrroloä2,1-cüä1,4übenzodiazepine als potentielle antitumor-agentien und ihre herstellung
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
US7511032B2 (en) 2003-10-22 2009-03-31 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
JP4520411B2 (ja) 2003-12-31 2010-08-04 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 ピロロ［２，１−ｃ］［１，４］ベンゾジアゼピン・ハイブリッドの調製方法
AU2005219626B2 (en) * 2004-03-01 2010-11-18 Medimmune Limited 11-hydroxy-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one derivatives as key intermediates for the preparation of C2 substituted pyrrolobenzodiazepines
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
DE602006011300D1 (de) 2005-04-21 2010-02-04 Spirogen Ltd Pyrrolobenzodiazepine
WO2007039752A1 (en) 2005-10-05 2007-04-12 Spirogen Limited Alkyl 4- [4- (5-oxo-2, 3, 5, 11a-tetrahyd0-5h-pyrr0l0 [2, 1-c] [1, 4] benzodiazepine-8-yloxy) -butyrylamino]-1h-pyrrole-2-carboxylate derivatives and related compounds for the treatment of a proliferative disease
EP1979349B1 (en) * 2005-12-21 2010-07-28 Abbott Laboratories Anti-viral compounds
PT1813614E (pt) 2006-01-25 2012-01-09 Sanofi Sa Agentes citotóxicos compreendendo novos derivados de tomaimicina
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
US8524865B2 (en) 2006-05-30 2013-09-03 Genentech, Inc. Antibodies and immunoconjugates and uses therefor
DK2019104T3 (da) 2007-07-19 2013-12-16 Sanofi Sa Cytotoksiske midler, der omfatter nye tomaymycinderivater, og terapeutisk anvendelse deraf
JP5404624B2 (ja) 2007-08-01 2014-02-05 カウンスィル オブ サイエンティフィック アンド インダストリアル リサーチ 選択的な抗腫瘍薬として有用なピロロ［２，１−ｃ］［１，４］ベンゾジアゼピン−グリコシドプロドラッグ
CN102083461B (zh) 2008-04-30 2014-09-17 伊缪诺金公司 有效的偶联物和亲水性连接体
CN104524592B (zh) 2008-04-30 2018-06-05 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
EP2383263B1 (en) * 2008-12-30 2014-04-16 Industry-academic Cooperation Foundation, Chosun University Novel thiazolidinedione derivative and use thereof
JP2013506709A (ja) 2009-10-06 2013-02-28 イミュノジェン・インコーポレーテッド 有効なコンジュゲートおよび親水性リンカー
US8314250B2 (en) 2009-11-24 2012-11-20 Hoffmann-La Roche Inc. Sultam derivatives
EP2511260B1 (en) 2009-12-08 2015-07-29 Gifu University Aromatic compound, modification carrier that uses same and is used for synthesizing an oligonucleotide derivative, oligonucleotide derivative, and oligonucleotide construct
LT3202460T (lt) * 2010-02-11 2019-10-10 Celgene Corporation Arilmetoksi izoindolino dariniai ir kompozicijos, apimantys ir jų panaudojimo būdus
SMT201700139T1 (it) 2010-02-24 2017-05-08 Immunogen Inc Immunoconiugati contro il recettore 1 del folato e relativi usi
HRP20130953T1 (hr) 2010-04-15 2013-11-22 Spirogen Sàrl Pirolobenzodiazepini i njihovi konjugati
US8697688B2 (en) 2010-04-15 2014-04-15 Seattle Genetics Inc. Pyrrolobenzodiazepines used to treat proliferative diseases
MX2012011900A (es) * 2010-04-15 2013-03-21 Seattle Genetics Inc Conjugados de pirrolobenzodiazepina diana.
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
WO2015051045A2 (en) * 2013-10-04 2015-04-09 Novartis Ag 3'END CAPS FOR RNAi AGENTS FOR USE IN RNA INTERFERENCE
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
MX2017002758A (es) 2014-09-03 2017-10-20 Immunogen Inc Derivados de benzodiazepina citotoxicos.
SG11201701565PA (en) * 2014-09-03 2017-03-30 Immunogen Inc Conjugates comprising cell-binding agents and cytotoxic agents
US9381256B2 (en) 2014-09-03 2016-07-05 Immunogen, Inc. Cytotoxic benzodiazepine derivatives
EP3325483B1 (en) 2015-07-21 2019-10-02 ImmunoGen, Inc. Methods of preparing cytotoxic benzodiazepine derivatives
JP2019501139A (ja) * 2015-11-25 2019-01-17 イミュノジェン・インコーポレーテッド 医薬製剤及びその使用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010064141A1 (en) 2008-12-05 2010-06-10 Christoph Merten Assay
WO2010091150A1 (en) 2009-02-05 2010-08-12 Immunogen, Inc. Novel benzodiazepine derivatives
US20110159481A1 (en) 2009-12-30 2011-06-30 Liu David J Solid-phase chelators and electronic biosensors
WO2012128868A1 (en) 2011-02-15 2012-09-27 Immunogen, Inc. Cytotoxic benzodiazepine derivatives

Also Published As

Publication number Publication date
IL305989A (en) 2023-11-01
AU2021203148B2 (en) 2023-01-12
IL256860A (en) 2018-03-29
IL305279A (en) 2023-10-01
CY1122553T1 (el) 2021-01-27
SMT202000506T1 (it) 2020-11-10
US20210171547A1 (en) 2021-06-10
SI3325482T1 (sl) 2020-11-30
KR20240055903A (ko) 2024-04-29
US11420982B2 (en) 2022-08-23
SG10202009354SA (en) 2020-11-27
SG10202106529XA (en) 2021-07-29
CA2991305C (en) 2024-03-12
EP3653628B1 (en) 2022-09-14
RU2018105609A (ru) 2019-08-26
IL256861A (en) 2018-03-29
RU2018105609A3 (enExample) 2020-04-30
IL256861B (en) 2020-08-31
IL276631A (en) 2020-09-30
EP3325482A1 (en) 2018-05-30
PT3325483T (pt) 2020-01-15
US10392407B2 (en) 2019-08-27
CA3227588A1 (en) 2017-01-26
CN113087763A (zh) 2021-07-09
CN108055844A (zh) 2018-05-18
RU2018105752A (ru) 2019-08-21
WO2017015495A1 (en) 2017-01-26
CA2992082A1 (en) 2017-01-26
RU2018105756A3 (enExample) 2019-12-23
EP3325485A1 (en) 2018-05-30
EP3778602A1 (en) 2021-02-17
IL286788B2 (en) 2024-01-01
CN108290895B (zh) 2021-03-19
HRP20201479T1 (hr) 2020-12-11
ES2764548T3 (es) 2020-06-03
EP3325482B1 (en) 2020-06-24
JP2021100959A (ja) 2021-07-08
IL294651B2 (en) 2024-02-01
JP6787995B2 (ja) 2020-11-18
US20170050986A1 (en) 2017-02-23
CN108026103A (zh) 2018-05-11
LT3325482T (lt) 2020-11-25
DK3325482T3 (da) 2020-09-28
WO2017015502A8 (en) 2017-03-02
AU2016297608B2 (en) 2021-02-18
CN108290895A (zh) 2018-07-17
RU2727151C2 (ru) 2020-07-21
CA2991305A1 (en) 2017-01-26
US20190010169A1 (en) 2019-01-10
SMT202000004T1 (it) 2020-03-13
US10081640B2 (en) 2018-09-25
EP4286387A3 (en) 2024-02-21
IL294651A (en) 2022-09-01
WO2017015496A1 (en) 2017-01-26
JP2021035958A (ja) 2021-03-04
LT3325483T (lt) 2020-01-27
IL283355B (en) 2022-08-01
US10370389B2 (en) 2019-08-06
AU2016297608A1 (en) 2018-02-08
US20170050985A1 (en) 2017-02-23
JP6995178B2 (ja) 2022-02-21
KR20180026741A (ko) 2018-03-13
RU2018105752A3 (enExample) 2019-12-30
RS60840B1 (sr) 2020-10-30
EP4286387A2 (en) 2023-12-06
IL286788B1 (en) 2023-09-01
HUE051541T2 (hu) 2021-03-01
JP2018524387A (ja) 2018-08-30
JP2023162264A (ja) 2023-11-08
JP2023166434A (ja) 2023-11-21
DK3325483T3 (da) 2020-01-20
RS59806B1 (sr) 2020-02-28
PL3325482T3 (pl) 2021-01-11
JP6858745B2 (ja) 2021-04-14
EP4163284A1 (en) 2023-04-12
US10899775B2 (en) 2021-01-26
HK1252322A1 (zh) 2019-05-24
US9890179B2 (en) 2018-02-13
ES2933376T3 (es) 2023-02-06
JP2018522018A (ja) 2018-08-09
AU2023201339A1 (en) 2023-04-06
AU2016297087A1 (en) 2018-02-08
US10787463B2 (en) 2020-09-29
PL3325483T3 (pl) 2020-05-18
AU2016297087B2 (en) 2021-02-18
EP3778602B1 (en) 2023-07-12
SI3325483T1 (sl) 2020-03-31
AU2021203148A1 (en) 2021-06-10
IL256860B (en) 2020-08-31
CN113004288A (zh) 2021-06-22
ES2959741T3 (es) 2024-02-28
AU2023202221A1 (en) 2023-05-04
WO2017015502A1 (en) 2017-01-26
KR102660070B1 (ko) 2024-04-24
CN108026103B (zh) 2021-04-16
IL283355A (en) 2021-07-29
JP7337114B2 (ja) 2023-09-01
AU2021202403A1 (en) 2021-05-20
HK1252321A1 (en) 2019-05-24
IL286788A (en) 2021-10-31
EP3325485B1 (en) 2020-04-08
HK1252323A1 (en) 2019-05-24
KR20180038461A (ko) 2018-04-16
EP3325483B1 (en) 2019-10-02
JP2018526340A (ja) 2018-09-13
CY1123390T1 (el) 2022-03-24
ES2820358T3 (es) 2021-04-20
EP3653628A1 (en) 2020-05-20
US20200017526A1 (en) 2020-01-16
IL276631B (en) 2021-10-31
PT3325482T (pt) 2020-09-24
US20210171546A1 (en) 2021-06-10
IL276630A (en) 2020-09-30
IL294651B1 (en) 2023-10-01
RU2018105756A (ru) 2019-08-21
CA2991326A1 (en) 2017-01-26
US20190389883A1 (en) 2019-12-26
US20230257400A1 (en) 2023-08-17
JP2022046542A (ja) 2022-03-23
US20180201626A1 (en) 2018-07-19
IL256854A (en) 2018-03-29
AU2016297607A1 (en) 2018-02-08
US20170051011A1 (en) 2017-02-23
JP7334228B2 (ja) 2023-08-28
KR20240055894A (ko) 2024-04-29
AU2021202403B2 (en) 2022-12-08
IL276630B (en) 2021-06-30
KR20180038460A (ko) 2018-04-16
US9873708B2 (en) 2018-01-23
US20190112320A1 (en) 2019-04-18
RU2746322C2 (ru) 2021-04-12
EP3325483A1 (en) 2018-05-30

Similar Documents

Publication Publication Date Title
KR102659706B1 (ko) 세포독성 벤조다이아제핀 유도체의 제조 방법
EP2648510B1 (en) Methods for the preparation of charged crosslinkers
HK40047253A (en) Methods of preparing cytotoxic benzodiazepine derivatives
HK40047253B (en) Methods of preparing cytotoxic benzodiazepine derivatives
HK1252321B (en) Methods of preparing cytotoxic benzodiazepine derivatives
HK1186066B (en) Methods for the preparation of charged crosslinkers

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

A201 Request for examination
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

GRNT Written decision to grant
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