WO2004046170A3 - Tubulysine, herstellungsverfahren und tubulysin-mittel - Google Patents

Tubulysine, herstellungsverfahren und tubulysin-mittel Download PDF

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Publication number
WO2004046170A3
WO2004046170A3 PCT/EP2003/011603 EP0311603W WO2004046170A3 WO 2004046170 A3 WO2004046170 A3 WO 2004046170A3 EP 0311603 W EP0311603 W EP 0311603W WO 2004046170 A3 WO2004046170 A3 WO 2004046170A3
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
aryl
alkenyl
tubulysin
tubulysins
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
PCT/EP2003/011603
Other languages
English (en)
French (fr)
Other versions
WO2004046170A2 (de
Inventor
Gerhard Hoefle
Nicole Glaser
Heinrich Steinmetz
Thomas Leibold
Florenz Sasse
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.)
Helmholtz Zentrum fuer Infektionsforschung HZI GmbH
Original Assignee
Helmholtz Zentrum fuer Infektionsforschung HZI GmbH
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 Helmholtz Zentrum fuer Infektionsforschung HZI GmbH filed Critical Helmholtz Zentrum fuer Infektionsforschung HZI GmbH
Priority to JP2004552485A priority Critical patent/JP4620467B2/ja
Priority to DE50310721T priority patent/DE50310721D1/de
Priority to US10/535,630 priority patent/US7754885B2/en
Priority to EP03775204A priority patent/EP1562979B1/de
Priority to AU2003283282A priority patent/AU2003283282A1/en
Publication of WO2004046170A2 publication Critical patent/WO2004046170A2/de
Publication of WO2004046170A3 publication Critical patent/WO2004046170A3/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/021—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)n-C(=0)-, n being 5 or 6; for n > 6, classification in C07K5/06 - C07K5/10, according to the moiety having normal peptide bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Die Erfindung betrifft eine Verbindung der folgenden allgemeinen Formel (Tubulysin) mit den folgenden Bedeutungen für R, R1, R2, R3, R4, R5, R6, R7,R8 R9, R10, R11, S, T, U, V, W, X, Y und Z: R = H, C1-4-Alkyl, Aryl, OR1, NR1R2 oder NH- (CH2) 2-R1 = H, C1-6-Alkyl oder Aryl R2 = H, C1-6-Alkyl oder Aryl S = H, Hal, NO2 oder NHR3 U = H, Hal, NO2 oder NHR3 R3 = H, HCO oder C1-4-Alkyl-CO T = H oder OR4 R4 = H, C1-4-Alkyl, Aryl, COR5, P (O) (OR6) 2 oder SO3R6 R5 = C1-6-Alkyl, Alkenyl, Aryl oder Heteroaryl R6 = H, C1-4-Alkyl oder Metallion V = H oder R7 oder (für W = O) O R7 = H, C1-4-Alkyl oder COR8 R8 = C-1-4-Alkyl, Alkenyl oder Aryl W = H oder C1-4-Alkyl oder (für V = O) O X = H, C1-4-Alkyl, Alkenyl oder CH20R9 R9 = H, C1-4-Alkyl, Alkenyl, Aryl oder COR10 R10 = C1-6-Alkyl, Alkenyl, Aryl oder Heteroaryl Y = (für Z = CH3 oder COR11)freies Elektronenpaar oder (für Z =CH3) O R11 = C1-4-Alkyl, CF3 oder Aryl und/oder Z = (für Y = O oder freies Elektronenpaar) CH3 oder (für Y = freies Elektronenpaar) COR11.
PCT/EP2003/011603 2002-11-21 2003-10-20 Tubulysine, herstellungsverfahren und tubulysin-mittel Ceased WO2004046170A2 (de)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2004552485A JP4620467B2 (ja) 2002-11-21 2003-10-20 チューブライシン、その製造方法、及び、チューブライシン製剤
DE50310721T DE50310721D1 (de) 2002-11-21 2003-10-20 Tubulysine, herstellungsverfahren und tubulysin-mittel
US10/535,630 US7754885B2 (en) 2002-11-21 2003-10-20 Tubulysins, method for producing the same and tubulysin preparations
EP03775204A EP1562979B1 (de) 2002-11-21 2003-10-20 Tubulysine, herstellungsverfahren und tubulysin-mittel
AU2003283282A AU2003283282A1 (en) 2002-11-21 2003-10-20 Tubulysins, method for producing the same and tubulysin preparations

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10254439A DE10254439A1 (de) 2002-11-21 2002-11-21 Tubulysine, Herstellungsverfahren und Tubulysin-Mittel
DE10254439.5 2002-11-21

Publications (2)

Publication Number Publication Date
WO2004046170A2 WO2004046170A2 (de) 2004-06-03
WO2004046170A3 true WO2004046170A3 (de) 2004-07-01

Family

ID=32240267

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/011603 Ceased WO2004046170A2 (de) 2002-11-21 2003-10-20 Tubulysine, herstellungsverfahren und tubulysin-mittel

Country Status (7)

Country Link
US (1) US7754885B2 (de)
EP (2) EP1562979B1 (de)
JP (1) JP4620467B2 (de)
AT (1) ATE412659T1 (de)
AU (1) AU2003283282A1 (de)
DE (2) DE10254439A1 (de)
WO (1) WO2004046170A2 (de)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9138484B2 (en) 2007-06-25 2015-09-22 Endocyte, Inc. Conjugates containing hydrophilic spacer linkers
US9187521B2 (en) 2007-10-25 2015-11-17 Endocyte, Inc. Tubulysins and processes for preparing
US9505747B2 (en) 2012-03-29 2016-11-29 Endocyte, Inc. Processes for preparing tubulysin derivatives and conjugates thereof
US9550734B2 (en) 2004-07-23 2017-01-24 Endocyte, Inc. Bivalent linkers and conjugates thereof
US9555139B2 (en) 2007-03-14 2017-01-31 Endocyte, Inc. Binding ligand linked drug delivery conjugates of tubulysins
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

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WO2002085908A1 (en) 2001-04-24 2002-10-31 Purdue Research Foundation Folate mimetics and folate-receptor binding conjugates thereof
CA2484640C (en) * 2002-05-15 2012-01-17 Endocyte, Inc. Vitamin-mitomycin conjugates
DK1523493T3 (da) * 2002-07-09 2013-12-02 Alexander Doemling Nye tubulysinanaloge
JP5576007B2 (ja) 2003-01-27 2014-08-20 エンドサイト・インコーポレイテッド ビタミン受容体結合性薬剤送達結合体
WO2006101845A2 (en) * 2005-03-16 2006-09-28 Endocyte, Inc. Synthesis and purification of pteroic acid and conjugates thereof
EP2374480A3 (de) * 2005-08-19 2013-05-01 Endocyte, Inc. Multidrug-Ligandenkonjugate
JP2009504783A (ja) * 2005-08-19 2009-02-05 エンドサイト，インコーポレイテッド ビンカアルカロイド、類似体および誘導体のリガンド結合体
US20100104626A1 (en) * 2007-02-16 2010-04-29 Endocyte, Inc. Methods and compositions for treating and diagnosing kidney disease
EP2532673A3 (de) * 2007-05-10 2014-01-08 R & D Biopharmaceuticals Gmbh Tubulysinderivate
US9877965B2 (en) 2007-06-25 2018-01-30 Endocyte, Inc. Vitamin receptor drug delivery conjugates for treating inflammation
US8476451B2 (en) * 2007-07-20 2013-07-02 The Regents Of The University Of California Tubulysin D analogues
WO2009012958A2 (en) * 2007-07-20 2009-01-29 Helmholtz-Zentrum für Infektionsforschung GmbH Tubulysin d analogues
EP2174947A1 (de) * 2008-09-25 2010-04-14 Universität des Saarlandes Bioaktive Prätubulysine und Verwendung davon
IT1394860B1 (it) 2009-07-22 2012-07-20 Kemotech S R L Composti farmaceutici
US8394922B2 (en) * 2009-08-03 2013-03-12 Medarex, Inc. Antiproliferative compounds, conjugates thereof, methods therefor, and uses thereof
EP2409983A1 (de) * 2010-07-19 2012-01-25 Leibniz-Institut für Pflanzenbiochemie (IPB) Tubulysinanaloga
MX2013001402A (es) * 2010-08-06 2013-08-29 Endocyte Inc Proceso para preparar tubulisinas.
CA2837840C (en) 2011-06-10 2020-08-04 Mersana Therapeutics, Inc. Protein-polymer-drug conjugates
AU2012348017A1 (en) * 2011-12-05 2014-07-03 Igenica Biotherapeutics, Inc. Antibody-drug conjugates and related compounds, compositions, and methods
US10080805B2 (en) 2012-02-24 2018-09-25 Purdue Research Foundation Cholecystokinin B receptor targeting for imaging and therapy
EP3925627A1 (de) 2012-05-15 2021-12-22 Concortis Biosystems, Corp Arzneimittel-konjugate und verwendungen davon
EP3210627B1 (de) 2012-07-12 2022-12-21 Hangzhou Dac Biotech Co., Ltd Konjugate aus zellbindungsmolekülen mit zytotoxika
US11873281B2 (en) 2012-07-12 2024-01-16 Hangzhou Dac Biotech Co., Ltd. Conjugates of cell binding molecules with cytotoxic agents
EP2708243A1 (de) 2012-09-17 2014-03-19 OntoChem GmbH Rezeptor-Ligand-verbundene zytotoxische Moleküle
JP2015536323A (ja) 2012-10-16 2015-12-21 エンドサイト・インコーポレイテッドＥｎｄｏｃｙｔｅ， Ｉｎｃ． 非天然アミノ酸を含む薬物送達結合体および使用方法
AU2013344778C1 (en) 2012-11-15 2024-06-27 Endocyte, Inc. Conjugates for treating diseases caused by PSMA expressing cells
AU2012395148B2 (en) 2012-11-24 2016-10-27 Hangzhou Dac Biotech Co., Ltd. Hydrophilic linkers and their uses for conjugation of drugs to cell binding molecules
CA2892863C (en) 2012-12-10 2022-03-15 Mersana Therapeutics, Inc. Polymeric scaffold based on phf for targeted drug delivery
EP2931316B1 (de) 2012-12-12 2019-02-20 Mersana Therapeutics, Inc. Hydroxylpolymer-heilmittelproteinkonjugate
LT2956173T (lt) 2013-02-14 2017-06-26 Bristol-Myers Squibb Company Tubulizino junginiai, gavimo ir panaudojimo būdai
US20140249315A1 (en) 2013-03-01 2014-09-04 Endocyte, Inc. Processes for preparing tubulysins
WO2014197866A1 (en) 2013-06-06 2014-12-11 Igenica Biotherapeutics, Inc. Modified antibodies and related compounds, compositions, and methods of use
AU2014337555C1 (en) 2013-10-15 2021-01-28 Seagen Inc. PEGylated drug-linkers for improved Ligand-Drug Conjugate pharmacokinetics
EP3057610B1 (de) 2013-10-15 2021-09-22 Sorrento Therapeutics, Inc. Wirkstoffkonjugate mit einem zielmolekül und zwei verschiedenen wirkstoffen
ES2843537T3 (es) 2014-01-28 2021-07-19 Tube Pharmaceuticals Gmbh Compuestos citotóxicos de tubulisina y conjugados de los mismos
FI3122757T3 (fi) 2014-02-28 2023-10-10 Hangzhou Dac Biotech Co Ltd Varautuneita linkkereitä ja niiden konjugointikäyttötapoja
SG11201608192SA (en) 2014-04-11 2016-10-28 Medimmune Llc Bispecific her2 antibodies
US10077287B2 (en) 2014-11-10 2018-09-18 Bristol-Myers Squibb Company Tubulysin analogs and methods of making and use
CN110279872A (zh) * 2014-11-11 2019-09-27 杭州多禧生物科技有限公司 细胞毒素分子同细胞结合受体分子的共轭体
JP6871858B2 (ja) 2015-01-28 2021-05-19 ソレント・セラピューティクス・インコーポレイテッドＳｏｒｒｅｎｔｏ Ｔｈｅｒａｐｅｕｔｉｃｓ， Ｉｎｃ． 抗体薬物コンジュゲート
EP3319936B1 (de) 2015-07-12 2025-12-17 Hangzhou Dac Biotech Co., Ltd. Brückenlinker zur konjugation von zellbindenden molekülen
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
LT3374398T (lt) 2015-11-10 2020-09-10 Medimmune, Llc Asct2 atžvilgiu specifinės surišančios molekulės ir jų panaudojimai
KR102626498B1 (ko) 2016-03-25 2024-01-19 씨젠 인크. 페길화된 약물-링커 및 그의 중간체의 제조를 위한 공정
AU2016429272A1 (en) 2016-11-14 2019-05-02 Hangzhou Dac Biotech Co., Ltd. Conjugation linkers, cell binding molecule-drug conjugates containing the likers, methods of making and uses such conjugates with the linkers
US11730822B2 (en) 2017-03-24 2023-08-22 Seagen Inc. Process for the preparation of glucuronide drug-linkers and intermediates thereof
SG11202000499RA (en) 2017-08-01 2020-02-27 Medimmune Llc Bcma monoclonal antibody-drug conjugate
JP2022540395A (ja) 2019-06-29 2022-09-15 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． 細胞結合性分子－チューブリシン誘導体共役体及びその調製方法
WO2021013999A1 (en) 2019-07-24 2021-01-28 Ontochem Gmbh Receptor-targeting peptide-drug conjugates
CA3193594A1 (en) 2020-09-11 2022-03-17 Medimmune Limited Therapeutic b7-h4 binding molecules
CN117980327A (zh) 2021-11-03 2024-05-03 杭州多禧生物科技有限公司 抗体的特异性偶联
GB202117928D0 (en) 2021-12-11 2022-01-26 Cancer Research Tech Ltd Immunotherapy for cancer
AU2023229884A1 (en) 2022-03-09 2024-10-10 Astrazeneca Ab BINDING MOLECULES AGAINST FRα
JP2026506049A (ja) 2023-02-16 2026-02-20 アストラゼネカ・アクチエボラーグ 治療用結合分子を用いた癌の治療のための併用療法

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DE10008089A1 (de) * 2000-02-22 2001-10-31 Biotechnolog Forschung Gmbh Syntheseverfahren zur Herstellung von Tubulysinen

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Publication number Priority date Publication date Assignee Title
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Patent Citations (2)

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DE10008089A1 (de) * 2000-02-22 2001-10-31 Biotechnolog Forschung Gmbh Syntheseverfahren zur Herstellung von Tubulysinen

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9550734B2 (en) 2004-07-23 2017-01-24 Endocyte, Inc. Bivalent linkers and conjugates thereof
US9555139B2 (en) 2007-03-14 2017-01-31 Endocyte, Inc. Binding ligand linked drug delivery conjugates of tubulysins
US9138484B2 (en) 2007-06-25 2015-09-22 Endocyte, Inc. Conjugates containing hydrophilic spacer linkers
US9187521B2 (en) 2007-10-25 2015-11-17 Endocyte, Inc. Tubulysins and processes for preparing
US9505747B2 (en) 2012-03-29 2016-11-29 Endocyte, Inc. Processes for preparing tubulysin derivatives and conjugates 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

Also Published As

Publication number Publication date
WO2004046170A2 (de) 2004-06-03
US7754885B2 (en) 2010-07-13
AU2003283282A1 (en) 2004-06-15
AU2003283282A8 (en) 2004-06-15
US20060128754A1 (en) 2006-06-15
JP4620467B2 (ja) 2011-01-26
DE10254439A1 (de) 2004-06-03
EP1562979A2 (de) 2005-08-17
EP1562979B1 (de) 2008-10-29
EP2028185A1 (de) 2009-02-25
DE50310721D1 (de) 2008-12-11
ATE412659T1 (de) 2008-11-15
JP2006518704A (ja) 2006-08-17

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