AU2013328673B2 - Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation - Google Patents

Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation Download PDF

Info

Publication number
AU2013328673B2
AU2013328673B2 AU2013328673A AU2013328673A AU2013328673B2 AU 2013328673 B2 AU2013328673 B2 AU 2013328673B2 AU 2013328673 A AU2013328673 A AU 2013328673A AU 2013328673 A AU2013328673 A AU 2013328673A AU 2013328673 B2 AU2013328673 B2 AU 2013328673B2
Authority
AU
Australia
Prior art keywords
group
formula
single bond
compound
alkyl
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.)
Ceased
Application number
AU2013328673A
Other languages
English (en)
Other versions
AU2013328673A1 (en
Inventor
Philip Wilson Howard
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
MedImmune Ltd
Original Assignee
MedImmune Ltd
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 MedImmune Ltd filed Critical MedImmune Ltd
Publication of AU2013328673A1 publication Critical patent/AU2013328673A1/en
Assigned to MEDIMMUNE LIMITED reassignment MEDIMMUNE LIMITED Request for Assignment Assignors: SPIROGEN SARL
Application granted granted Critical
Publication of AU2013328673B2 publication Critical patent/AU2013328673B2/en
Ceased legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/62Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
    • A61K47/65Peptidic linkers, binders or spacers, e.g. peptidic enzyme-labile linkers
    • 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
    • C07K5/06034Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06043Leu-amino acid
    • 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
    • C07K5/06034Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06052Val-amino acid
    • 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
    • C07K5/06078Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • 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
    • C07K5/06139Dipeptides with the first amino acid being heterocyclic

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
AU2013328673A 2012-10-12 2013-10-11 Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation Ceased AU2013328673B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261713083P 2012-10-12 2012-10-12
US61/713,083 2012-10-12
PCT/EP2013/071234 WO2014057072A1 (en) 2012-10-12 2013-10-11 Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation

Publications (2)

Publication Number Publication Date
AU2013328673A1 AU2013328673A1 (en) 2015-04-02
AU2013328673B2 true AU2013328673B2 (en) 2017-07-13

Family

ID=49510114

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2013328673A Ceased AU2013328673B2 (en) 2012-10-12 2013-10-11 Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation

Country Status (6)

Country Link
US (1) US9745303B2 (OSRAM)
EP (1) EP2906249B1 (OSRAM)
JP (1) JP6367204B2 (OSRAM)
AU (1) AU2013328673B2 (OSRAM)
CA (1) CA2885305C (OSRAM)
WO (1) WO2014057072A1 (OSRAM)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0819095D0 (en) 2008-10-17 2008-11-26 Spirogen Ltd Pyrrolobenzodiazepines
JP5875083B2 (ja) 2010-04-15 2016-03-02 メディミューン リミテッド 増殖性疾患治療用ピロロベンゾジアゼピン
KR101671360B1 (ko) 2010-04-15 2016-11-01 시애틀 지네틱스, 인크. 표적화된 피롤로벤조디아제핀 접합체
MX341524B (es) 2011-09-20 2016-08-24 Medimmune Ltd Pirrolobenzodiazepinas como compuestos pbd dimericos asimetricos para inclusion en conjugados dirigidos.
EA026643B1 (ru) 2011-10-14 2017-04-28 Сиэтл Дженетикс, Инк. Пирролбензодиазепины и конъюгаты направленного действия
WO2013055990A1 (en) 2011-10-14 2013-04-18 Seattle Genetics, Inc. Pyrrolobenzodiazepines and targeted conjugates
EA027386B1 (ru) 2011-10-14 2017-07-31 Медимьюн Лимитед Пирролобензодиазепины
US9399073B2 (en) 2011-10-14 2016-07-26 Seattle Genetics, Inc. Pyrrolobenzodiazepines
RS57104B1 (sr) 2012-10-12 2018-06-29 Adc Therapeutics Sa Konjugati pirolobenzodiazepin-antitela
WO2014057120A1 (en) 2012-10-12 2014-04-17 Adc Therapeutics Sàrl Pyrrolobenzodiazepine-antibody conjugates
ES2713164T3 (es) 2012-10-12 2019-05-20 Medimmune Ltd Pirrolobenzodiazepinas y conjugados de las mismas
US9745303B2 (en) 2012-10-12 2017-08-29 Medimmune Limited Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation
AU2013328580B2 (en) 2012-10-12 2016-01-21 Medimmune Limited Pyrrolobenzodiazepines and conjugates thereof
JP6392765B2 (ja) 2012-10-12 2018-09-19 エイディーシー・セラピューティクス・エス・アーAdc Therapeutics Sa ピロロベンゾジアゼピン−抗体結合体
WO2014057114A1 (en) 2012-10-12 2014-04-17 Adc Therapeutics Sàrl Pyrrolobenzodiazepine-anti-psma antibody conjugates
EP2906253B9 (en) 2012-10-12 2019-02-27 ADC Therapeutics SA Pyrrolobenzodiazepine - anti-psma antibody conjugates
NZ707534A (en) 2012-10-12 2018-08-31 Adc Therapeutics Sa Pyrrolobenzodiazepine-antibody conjugates
EA032986B1 (ru) 2012-12-21 2019-08-30 Медимьюн Лимитед Пирролобензодиазепины
CA2894961C (en) 2012-12-21 2020-09-15 Spirogen Sarl Pyrrolobenzodiazepines and conjugates thereof
ME03394B (me) 2013-02-22 2020-01-20 Medimmune Ltd Antidllз-antitelo-pbd konjugati i nihovа upotreba
US9649390B2 (en) 2013-03-13 2017-05-16 Medimmune Limited Pyrrolobenzodiazepines and conjugates thereof
TWI680766B (zh) 2013-03-13 2020-01-01 英商梅迪繆思有限公司 吡咯并苯并二氮呯及其共軛物
BR112016004242A8 (pt) 2013-08-28 2018-06-12 Stemcentrx Inc Métodos para conjugação sítio-específica de anticorpos e composições
GB201317982D0 (en) 2013-10-11 2013-11-27 Spirogen Sarl Pyrrolobenzodiazepines and conjugates thereof
EP3054986B1 (en) 2013-10-11 2019-03-20 Medimmune Limited Pyrrolobenzodiazepine-antibody conjugates
GB201317981D0 (en) 2013-10-11 2013-11-27 Spirogen Sarl Pyrrolobenzodiazepines and conjugates thereof
EP3054985B1 (en) 2013-10-11 2018-12-26 Medimmune Limited Pyrrolobenzodiazepine-antibody conjugates
US10010624B2 (en) 2013-10-11 2018-07-03 Medimmune Limited Pyrrolobenzodiazepine-antibody conjugates
KR20170008202A (ko) 2014-02-21 2017-01-23 애브비 스템센트알엑스 엘엘씨 흑색종에 사용하기 위한 항-dll3 항체 및 약물 접합체
SG11201701623UA (en) 2014-09-12 2017-03-30 Genentech Inc Anti-her2 antibodies and immunoconjugates
GB201416112D0 (en) 2014-09-12 2014-10-29 Medimmune Ltd Pyrrolobenzodiazepines and conjugates thereof
BR112017011111A2 (pt) 2014-11-25 2017-12-26 Adc Therapeutics Sa conjugados de pirrolobenzodiazepina-anticorpo
GB201506402D0 (en) 2015-04-15 2015-05-27 Berkel Patricius H C Van And Howard Philip W Site-specific antibody-drug conjugates
GB201506411D0 (en) 2015-04-15 2015-05-27 Bergenbio As Humanized anti-axl antibodies
MA43345A (fr) 2015-10-02 2018-08-08 Hoffmann La Roche Conjugués anticorps-médicaments de pyrrolobenzodiazépine et méthodes d'utilisation
GB201601431D0 (en) 2016-01-26 2016-03-09 Medimmune Ltd Pyrrolobenzodiazepines
GB201602356D0 (en) 2016-02-10 2016-03-23 Medimmune Ltd Pyrrolobenzodiazepine Conjugates
GB201602359D0 (en) 2016-02-10 2016-03-23 Medimmune Ltd Pyrrolobenzodiazepine Conjugates
GB201607478D0 (en) 2016-04-29 2016-06-15 Medimmune Ltd Pyrrolobenzodiazepine Conjugates
GB201617466D0 (en) 2016-10-14 2016-11-30 Medimmune Ltd Pyrrolobenzodiazepine conjugates
GB201619490D0 (en) * 2016-11-17 2017-01-04 Medimmune Ltd Pyrrolobenzodiazepine conjugates
GB201702031D0 (en) 2017-02-08 2017-03-22 Medlmmune Ltd Pyrrolobenzodiazepine-antibody conjugates
BR112019016373B1 (pt) 2017-02-08 2022-01-25 Medimmune Limited Conjugado anticorpo-fármaco que se liga ao axl, composição e composição farmacêutica que compreende o mesmo e uso terapêutico do dito conjugado
US11370801B2 (en) 2017-04-18 2022-06-28 Medimmune Limited Pyrrolobenzodiazepine conjugates
EP3612234B1 (en) 2017-04-20 2024-03-13 ADC Therapeutics SA Combination therapy with an anti-axl antibody-drug conjugate
JP7145891B2 (ja) 2017-06-14 2022-10-03 アーデーセー セラピューティクス ソシエテ アノニム 抗cd19 adcを投与するための投与レジメ
PT3668874T (pt) 2017-08-18 2022-02-24 Medimmune Ltd Conjugados de pirrolobenzodiazepina
CN117003875A (zh) 2017-09-29 2023-11-07 第一三共株式会社 抗体或其功能性片段、多核苷酸、表达载体、宿主细胞、糖链重构抗体、药物组合物、应用
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
MX2021010477A (es) 2019-03-15 2021-10-01 Medimmune Ltd Dimeros de azetidobenzodiazepina y conjugados que los comprenden para uso en el tratamiento de cancer.
WO2024005123A1 (ja) 2022-06-30 2024-01-04 東レ株式会社 癌の治療及び/又は予防用医薬組成物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008009079A2 (en) * 2006-07-20 2008-01-24 Gilead Sciences, Inc. Substituted pteridines useful for the treatment and prevention of viral infections
WO2009027707A2 (en) * 2007-08-31 2009-03-05 University Of Kent Methods for preparing peptides, especially radio-labelled peptides
WO2012109164A1 (en) * 2011-02-07 2012-08-16 Rempex Pharmaceuticals, Inc. Boron containing polybasic bacterial efflux pump inhibitors and therapeutics uses thereof

Family Cites Families (130)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3361742A (en) 1964-12-07 1968-01-02 Hoffmann La Roche 5-oxo-1h-pyrrolo-[2, 1-c][1, 4]-benzodiazepin-2-crylamides
US3523941A (en) 1967-03-06 1970-08-11 Hoffmann La Roche Benzodiazepine compounds and process for their preparation
US3524849A (en) 1967-10-27 1970-08-18 Hoffmann La Roche Process for the preparation of pyrrolo-benzodiazepine acrylamides and intermediates useful therein
JPS4843755B1 (OSRAM) 1969-06-26 1973-12-20
DE1965304A1 (de) 1968-12-30 1970-07-23 Fujisawa Pharmaceutical Co Benzdiazepinon-Verbindungen und Verfahren zu ihrer Herstellung
IL33558A (en) 1968-12-30 1973-10-25 Fujisawa Pharmaceutical Co Antibiotic pyrrolo-benzodiazepine compound,its derivatives and processes for their production
JPS6053033B2 (ja) 1976-12-28 1985-11-22 財団法人微生物化学研究会 新制癌抗生物質マゼスラマイシン及びその製造方法
JPS585916B2 (ja) 1977-12-27 1983-02-02 株式会社ミドリ十字 新規ベンゾジアゼピン系化合物
JPS5615289A (en) 1979-07-17 1981-02-14 Green Cross Corp:The Novel benzodiazepinnbased compound 3
JPS57131791A (en) 1980-12-31 1982-08-14 Fujisawa Pharmaceut Co Ltd Benzodiazepine derivative and its preparation
CA1185602A (en) 1981-02-27 1985-04-16 Emilio Kyburz Imidazodiazepines
CA1184175A (en) 1981-02-27 1985-03-19 Walter Hunkeler Imidazodiazepines
CA1173441A (en) 1981-02-27 1984-08-28 Hoffmann-La Roche Limited Imidazodiazepines
JPS58180487A (ja) 1982-04-16 1983-10-21 Kyowa Hakko Kogyo Co Ltd 抗生物質dc−81およびその製造法
US4427588A (en) 1982-11-08 1984-01-24 Bristol-Myers Company Process for conversion of oxotomaymycin to tomaymycin
US4427587A (en) 1982-11-10 1984-01-24 Bristol-Myers Company Total synthesis of antitumor antibiotics BBM-2040A and BBM-2040B
JPS59152329A (ja) 1983-02-17 1984-08-31 Green Cross Corp:The 局所障害抑制剤
US4816567A (en) 1983-04-08 1989-03-28 Genentech, Inc. Recombinant immunoglobin preparations
FR2586683B1 (fr) 1985-08-29 1988-07-01 Centre Nat Rech Scient Nouveaux derives de neothramycine, leur procede de preparation et leur application en tant que medicaments
US5583024A (en) 1985-12-02 1996-12-10 The Regents Of The University Of California Recombinant expression of Coleoptera luciferase
JP2660201B2 (ja) 1988-08-05 1997-10-08 塩野義製薬株式会社 新規ピロロ[1,4]ベンゾジアゼピン誘導体および老人性痴呆薬
FR2676230B1 (fr) 1991-05-07 1993-08-27 Centre Nat Rech Scient Nouveaux derives de pyrrolo [1,4]-benzodiazepines, leur procede de preparation et medicaments les contenant.
GB9205051D0 (en) 1992-03-09 1992-04-22 Cancer Res Campaign Tech Pyrrolobenzodiazepine derivatives,their preparation,and compositions containing them
FR2696176B1 (fr) 1992-09-28 1994-11-10 Synthelabo Dérivés de pipéridine, leur préparation et leur application en thérapeutique.
US6214345B1 (en) 1993-05-14 2001-04-10 Bristol-Myers Squibb Co. Lysosomal enzyme-cleavable antitumor drug conjugates
GB9316162D0 (en) 1993-08-04 1993-09-22 Zeneca Ltd Fungicides
US6143790A (en) 1994-03-10 2000-11-07 G.D. Searle & Co. L-N6 -(1-iminoethyl)lysine derivatives useful as nitric oxide synthase inhibitors
JPH08336393A (ja) 1995-04-13 1996-12-24 Mitsubishi Chem Corp 光学活性なγ−置換−β−ヒドロキシ酪酸エステルの製造法
DE69934618T2 (de) 1998-07-08 2007-05-03 E-Ink Corp., Cambridge Verbesserte farbige mikroverkapselte elektrophoretische Anzeige
ES2244210T3 (es) 1998-08-27 2005-12-01 Spirogen Limited Pirrolobenzodiazepinas.
GB9818730D0 (en) 1998-08-27 1998-10-21 Univ Portsmouth Collections of compounds
GB9818732D0 (en) 1998-08-27 1998-10-21 Univ Portsmouth Collection of compounds
GB9818731D0 (en) 1998-08-27 1998-10-21 Univ Portsmouth Compounds
US6909006B1 (en) 1999-08-27 2005-06-21 Spirogen Limited Cyclopropylindole derivatives
DE60115265T2 (de) 2000-09-19 2006-08-10 Lee, Moses, Holland Zusammensetzungen und verfahren zur verwendung achiraler analoge von cc-1065 und den duocarmycinen
US6362331B1 (en) 2001-03-30 2002-03-26 Council Of Scientific And Industrial Research Process for the preparation of antitumor agents
EP1401850A1 (en) * 2001-06-20 2004-03-31 Nuevolution A/S Nucleoside derivatives for library preparation
US6660856B2 (en) 2002-03-08 2003-12-09 Kaohsiung Medical University Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine analogues
PT2357006E (pt) 2002-07-31 2016-01-22 Seattle Genetics Inc Conjugados de fármacos e sua utilização para tratamento do cancro, de uma doença autoimune ou de uma doença infeciosa
US20040138269A1 (en) 2002-10-11 2004-07-15 Sugen, Inc. Substituted pyrroles as kinase inhibitors
GB0226593D0 (en) 2002-11-14 2002-12-24 Consultants Ltd Compounds
DE60326060D1 (de) 2003-03-31 2009-03-19 Council Scient Ind Res Nichtvernetzende pyrroloä2,1-cüä1,4übenzodiazepine als potentielle antitumor-agentien und ihre herstellung
GB0321295D0 (en) 2003-09-11 2003-10-15 Spirogen Ltd Synthesis of protected pyrrolobenzodiazepines
AU2004284075A1 (en) 2003-10-22 2005-05-06 Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services Pyrrolobenzodiazepine derivatives, compositions comprising the same and methods related thereto
GB0416511D0 (en) 2003-10-22 2004-08-25 Spirogen Ltd Pyrrolobenzodiazepines
SG149815A1 (en) 2003-11-06 2009-02-27 Seattle Genetics Inc Monomethylvaline compounds capable of conjugation to ligands
AU2005214988A1 (en) 2004-02-17 2005-09-01 Absalus, Inc. Super-humanized antibodies against respiratory syncytial virus
JP5064037B2 (ja) 2004-02-23 2012-10-31 ジェネンテック, インコーポレイテッド 複素環式自壊的リンカーおよび結合体
ES2381858T3 (es) 2004-03-01 2012-06-01 Spirogen Limited 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
GB0404574D0 (en) 2004-03-01 2004-04-07 Spirogen Ltd Amino acids
GB0404577D0 (en) 2004-03-01 2004-04-07 Spirogen Ltd Pyrrolobenzodiazepines
GB0404578D0 (en) 2004-03-01 2004-04-07 Spirogen Ltd Pyrrolobenzodiazepines
DE102004010943A1 (de) 2004-03-03 2005-09-29 Degussa Ag Verfahren zur Herstellung von N-geschützten 4-Ketprolinderivaten
US7528126B2 (en) 2004-03-09 2009-05-05 Spirogen Limited Pyrrolobenzodiazepines
FR2869231B1 (fr) 2004-04-27 2008-03-14 Sod Conseils Rech Applic Composition therapeutique contenant au moins un derive de la pyrrolobenzodiazepine et la fludarabine
GB0410725D0 (en) 2004-05-13 2004-06-16 Spirogen Ltd Pyrrolobenzodiazepine therapeutic agents
TR201808537T4 (tr) 2004-09-23 2018-07-23 Genentech Inc Sistein değiştirilmiş antikorlar ve konjugatlar.
WO2006068325A2 (en) 2004-12-24 2006-06-29 Showa Denko K. K. Production method of thermoelectric semiconductor alloy, thermoelectric conversion module and thermoelectric power generating device
CN101203241B (zh) 2005-04-19 2012-02-22 西雅图基因公司 人源化抗-cd70结合物和其应用
WO2006111759A1 (en) 2005-04-21 2006-10-26 Spirogen Limited Pyrrolobenzodiazepines
US20070154906A1 (en) 2005-10-05 2007-07-05 Spirogen Ltd. Methods to identify therapeutic candidates
DE602006006199D1 (de) 2005-10-05 2009-05-20 Spirogen Ltd 4-ä4-(5-oxo-2,3,5,11a-tetrahydro-5h-pyrrolo ä2, 1-cüä1,4übenzodiazepin-8-yloxy)-butyrylaminoü-1h-pyrrol-2-carbonsäurealkylesterderivate und verwandte verbindung zur behandlung einer proliferativen erkrankung
PL1813614T3 (pl) 2006-01-25 2012-03-30 Sanofi Sa Środki cytotoksyczne zawierające nowe pochodne tomaymycyny
ES2673822T3 (es) 2006-07-18 2018-06-25 Sanofi Anticuerpo antagonista contra EphA2 para el tratamiento de cáncer
EP1914242A1 (en) 2006-10-19 2008-04-23 Sanofi-Aventis Novel anti-CD38 antibodies for the treatment of cancer
WO2008050140A2 (en) 2006-10-27 2008-05-02 Spirogen Limited Compounds for treatment of parasitic infection
CA2699837C (en) 2006-12-01 2017-06-13 Seattle Genetics, Inc. Variant target binding agents and uses thereof
JP2008291207A (ja) * 2007-04-27 2008-12-04 Kyowa Hakko Kirin Co Ltd 塩基性アミノ酸を有するらせん状ポリマー
AU2008251608B2 (en) 2007-05-08 2014-03-27 Genentech, Inc. Cysteine engineered anti-MUC16 antibodies and antibody drug conjugates
PT2019104E (pt) 2007-07-19 2013-12-03 Sanofi Sa Agentes citotóxicos compreendendo novos derivados de tomaimicina e sua utilização terapêutica
NZ584514A (en) 2007-10-19 2012-07-27 Genentech Inc Cysteine engineered anti-tenb2 antibodies and antibody drug conjugates
GB0722087D0 (en) 2007-11-09 2007-12-19 Spirogen Ltd Polyamides
GB0722088D0 (en) 2007-11-09 2007-12-19 Spirogen Ltd Pyrrolobenzodiazepines
EP2265283B1 (en) 2008-03-18 2014-09-03 Seattle Genetics, Inc. Auristatin drug linker conjugates
GB0813432D0 (en) 2008-07-22 2008-08-27 Spirogen Ltd Pyrrolobenzodiazepines
GB0819097D0 (en) 2008-10-17 2008-11-26 Spirogen Ltd Pyrrolobenzodiazepines
GB0819095D0 (en) 2008-10-17 2008-11-26 Spirogen Ltd Pyrrolobenzodiazepines
US20110077365A1 (en) 2008-12-29 2011-03-31 Gilbert Yu Preparation of organosilicon-containing triazoles
CN108727407B (zh) 2009-02-05 2022-01-28 伊缪诺金公司 新型苯并二氮杂䓬衍生物
CN101492494A (zh) 2009-03-05 2009-07-29 浙江大学 整合素配体环肽类似物及其环化方法
FR2949469A1 (fr) 2009-08-25 2011-03-04 Sanofi Aventis Derives anticancereux, leur preparation et leur application en therapeutique
KR20120083292A (ko) * 2009-09-16 2012-07-25 아스테라스 세이야쿠 가부시키가이샤 글리신 화합물
JP2013505944A (ja) 2009-09-24 2013-02-21 シアトル ジェネティックス, インコーポレイテッド Dr5リガンド薬物結合体
ES2449379T3 (es) 2010-02-09 2014-03-19 Bristol-Myers Squibb Company Derivados de bencilpirrolidinona como moduladores de la actividad de receptores de quimiocinas
GB201006340D0 (en) 2010-04-15 2010-06-02 Spirogen Ltd Synthesis method and intermediates
JP5875083B2 (ja) 2010-04-15 2016-03-02 メディミューン リミテッド 増殖性疾患治療用ピロロベンゾジアゼピン
TWI540136B (zh) 2010-04-15 2016-07-01 梅迪繆思有限公司 吡咯并苯并二氮呯及其共軛物
KR101671360B1 (ko) 2010-04-15 2016-11-01 시애틀 지네틱스, 인크. 표적화된 피롤로벤조디아제핀 접합체
WO2011130615A2 (en) 2010-04-15 2011-10-20 Dr. Reddy's Laboratories Ltd. Preparation of lacosamide
WO2012112708A1 (en) 2011-02-15 2012-08-23 Immunogen, Inc. Cytotoxic benzodiazepine derivatives and methods of preparation
MX341524B (es) 2011-09-20 2016-08-24 Medimmune Ltd Pirrolobenzodiazepinas como compuestos pbd dimericos asimetricos para inclusion en conjugados dirigidos.
WO2013055990A1 (en) 2011-10-14 2013-04-18 Seattle Genetics, Inc. Pyrrolobenzodiazepines and targeted conjugates
EA026643B1 (ru) 2011-10-14 2017-04-28 Сиэтл Дженетикс, Инк. Пирролбензодиазепины и конъюгаты направленного действия
US9399073B2 (en) 2011-10-14 2016-07-26 Seattle Genetics, Inc. Pyrrolobenzodiazepines
EA027386B1 (ru) 2011-10-14 2017-07-31 Медимьюн Лимитед Пирролобензодиазепины
SG11201401406YA (en) 2011-10-14 2014-05-29 Spirogen Sarl Pyrrolobenzodiazepines and conjugates thereof
CA2850096C (en) 2011-10-14 2018-07-03 Spirogen Sarl Synthesis method and intermediates useful in the preparation of pyrrolobenzodiazepines
AU2013221448B2 (en) * 2012-02-16 2017-02-23 The University Of Toledo Xenoantigen-displaying anti-cancer vaccines and method of making
FR2989085A1 (fr) * 2012-04-05 2013-10-11 Commissariat Energie Atomique Radiotraceurs, procedes de preparation et applications
AU2013255612B2 (en) 2012-04-30 2017-06-22 Medimmune Limited Pyrrolobenzodiazepines
US9376440B2 (en) 2012-04-30 2016-06-28 Medimmune Limited Pyrrolobenzodiazepines as antiproliferative agents
JP2015523380A (ja) 2012-07-09 2015-08-13 ジェネンテック, インコーポレイテッド 抗cd79b抗体を含む免疫複合体
TW201406785A (zh) 2012-07-09 2014-02-16 Genentech Inc 抗cd22抗體及免疫結合物
CN104717979A (zh) 2012-08-02 2015-06-17 基因泰克公司 抗etbr抗体和免疫偶联物
EP2906253B9 (en) 2012-10-12 2019-02-27 ADC Therapeutics SA Pyrrolobenzodiazepine - anti-psma antibody conjugates
JP6392765B2 (ja) 2012-10-12 2018-09-19 エイディーシー・セラピューティクス・エス・アーAdc Therapeutics Sa ピロロベンゾジアゼピン−抗体結合体
WO2014057114A1 (en) 2012-10-12 2014-04-17 Adc Therapeutics Sàrl Pyrrolobenzodiazepine-anti-psma antibody conjugates
AU2013328580B2 (en) 2012-10-12 2016-01-21 Medimmune Limited Pyrrolobenzodiazepines and conjugates thereof
WO2014057118A1 (en) 2012-10-12 2014-04-17 Adc Therapeutics Sarl Pyrrolobenzodiazepine-anti-cd22 antibody conjugates
RS57104B1 (sr) 2012-10-12 2018-06-29 Adc Therapeutics Sa Konjugati pirolobenzodiazepin-antitela
US9745303B2 (en) 2012-10-12 2017-08-29 Medimmune Limited Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation
ES2713164T3 (es) 2012-10-12 2019-05-20 Medimmune Ltd Pirrolobenzodiazepinas y conjugados de las mismas
NZ707534A (en) 2012-10-12 2018-08-31 Adc Therapeutics Sa Pyrrolobenzodiazepine-antibody conjugates
RS56222B1 (sr) 2012-10-12 2017-11-30 Adc Therapeutics Sa Pirolobenzodiazepin-anti-her2 konjugati antitela
WO2014057120A1 (en) 2012-10-12 2014-04-17 Adc Therapeutics Sàrl Pyrrolobenzodiazepine-antibody conjugates
CA2894961C (en) 2012-12-21 2020-09-15 Spirogen Sarl Pyrrolobenzodiazepines and conjugates thereof
EA032986B1 (ru) 2012-12-21 2019-08-30 Медимьюн Лимитед Пирролобензодиазепины
ME03394B (me) 2013-02-22 2020-01-20 Medimmune Ltd Antidllз-antitelo-pbd konjugati i nihovа upotreba
TWI680766B (zh) 2013-03-13 2020-01-01 英商梅迪繆思有限公司 吡咯并苯并二氮呯及其共軛物
US9649390B2 (en) 2013-03-13 2017-05-16 Medimmune Limited Pyrrolobenzodiazepines and conjugates thereof
MX362970B (es) 2013-03-13 2019-02-28 Medimmune Ltd Pirrolobenzodiazepinas y conjugados de las mismas.
WO2014174111A1 (en) 2013-04-26 2014-10-30 Pierre Fabre Medicament Axl antibody-drug conjugate and its use for the treatment of cancer
GB201317982D0 (en) 2013-10-11 2013-11-27 Spirogen Sarl Pyrrolobenzodiazepines and conjugates thereof
EP3054985B1 (en) 2013-10-11 2018-12-26 Medimmune Limited Pyrrolobenzodiazepine-antibody conjugates
US20160256561A1 (en) 2013-10-11 2016-09-08 Medimmune Limited Pyrrolobenzodiazepine-antibody conjugates
GB201317981D0 (en) 2013-10-11 2013-11-27 Spirogen Sarl Pyrrolobenzodiazepines and conjugates thereof
EP3054986B1 (en) 2013-10-11 2019-03-20 Medimmune Limited Pyrrolobenzodiazepine-antibody conjugates
US10010624B2 (en) 2013-10-11 2018-07-03 Medimmune Limited Pyrrolobenzodiazepine-antibody conjugates
HK1222577A1 (zh) 2013-12-16 2017-07-07 Genentech Inc. 擬肽化合物及其抗體藥物偶聯物
GB201406767D0 (en) 2014-04-15 2014-05-28 Cancer Rec Tech Ltd Humanized anti-Tn-MUC1 antibodies anf their conjugates

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008009079A2 (en) * 2006-07-20 2008-01-24 Gilead Sciences, Inc. Substituted pteridines useful for the treatment and prevention of viral infections
WO2009027707A2 (en) * 2007-08-31 2009-03-05 University Of Kent Methods for preparing peptides, especially radio-labelled peptides
WO2012109164A1 (en) * 2011-02-07 2012-08-16 Rempex Pharmaceuticals, Inc. Boron containing polybasic bacterial efflux pump inhibitors and therapeutics uses thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
GRAVEL, M. et al., "Universal Solid-Phase Approach for the Immobilization, Derivatization, and Resin-to-Resin Transfer Reactions of Boronic Acids", J. Org. Chem. 2002, Vol. 67, Pages 3-15 *
ITOH, F. et al., "Non-glutamate Type Pyrrolo[2,3-d]pyrimidine Antifolates. II. Synthesis and Antitumor Activity of N5-Substituted Glutamine Analogs", Chemical & Pharmaceutical Bulletin (1996), Vol. 44(8), Pages 1498-1509 *

Also Published As

Publication number Publication date
JP6367204B2 (ja) 2018-08-01
US9745303B2 (en) 2017-08-29
EP2906249A1 (en) 2015-08-19
HK1213488A1 (en) 2016-09-09
WO2014057072A1 (en) 2014-04-17
CA2885305C (en) 2019-11-12
EP2906249B1 (en) 2018-06-27
AU2013328673A1 (en) 2015-04-02
JP2015534574A (ja) 2015-12-03
CA2885305A1 (en) 2014-04-17
US20150274737A1 (en) 2015-10-01

Similar Documents

Publication Publication Date Title
AU2013328673B2 (en) Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation
AU2012311505B2 (en) Pyrrolobenzodiazepines as unsymmetrical dimeric PBD compounds for inclusion in targeted conjugates
JP7123635B2 (ja) ピロロベンゾジアゼピンおよび標的コンジュゲート
AU2009305190B2 (en) Unsymmetrical pyrrolobenzodiazepine-dimers for treatment of proliferative diseases
EP1879901B1 (en) Pyrrolobenzodiazepines
AU2012322934B2 (en) Pyrrolobenzodiazepines
CA2872205C (en) Pyrrolobenzodiazepines
AU2012322932B2 (en) Pyrrolobenzodiazepines
CA2795353C (en) Pyrrolobenzodiazepines used to treat proliferative diseases
EP2558127B1 (en) Targeted pyrrolobenzodiazepine conjugates
HK1213488B (en) Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation
HK1195073B (en) Pyrrolobenzodiazepines as unsymmetrical dimeric pbd compounds for inclusion in targeted conjugates
HK1195073A (en) Pyrrolobenzodiazepines as unsymmetrical dimeric pbd compounds for inclusion in targeted conjugates
HK1154575B (en) Unsymmetrical pyrrolobenzodiazepine-dimers for treatment of proliferative diseases

Legal Events

Date Code Title Description
PC1 Assignment before grant (sect. 113)

Owner name: MEDIMMUNE LIMITED

Free format text: FORMER APPLICANT(S): SPIROGEN SARL

FGA Letters patent sealed or granted (standard patent)
MK14 Patent ceased section 143(a) (annual fees not paid) or expired