AU2014354643B2 - Hydrazinyl-pyrrolo compounds and methods for producing a conjugate - Google Patents

Hydrazinyl-pyrrolo compounds and methods for producing a conjugate Download PDF

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AU2014354643B2
AU2014354643B2 AU2014354643A AU2014354643A AU2014354643B2 AU 2014354643 B2 AU2014354643 B2 AU 2014354643B2 AU 2014354643 A AU2014354643 A AU 2014354643A AU 2014354643 A AU2014354643 A AU 2014354643A AU 2014354643 B2 AU2014354643 B2 AU 2014354643B2
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substituted
alkyl
amino
certain embodiments
peg
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AU2014354643A1 (en
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Aaron Edward ALBERS
Albert W. Garofalo
Romas Alvydas KUDIRKA
Jesse M. McFARLAND
David Rabuka
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Redwood Bioscience Inc
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Redwood Bioscience Inc
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal 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
    • A61K47/51—Medicinal 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
    • A61K47/54—Medicinal 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 an organic compound
    • A61K47/545—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5386—1,4-Oxazines, e.g. morpholine spiro-condensed or forming part of bridged ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal 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
    • A61K47/51—Medicinal 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
    • A61K47/56—Medicinal 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 an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/59—Medicinal 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 an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
    • A61K47/60—Medicinal 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 an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
    • A—HUMAN NECESSITIES
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    • A61K47/50—Medicinal 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
    • A61K47/51—Medicinal 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
    • A61K47/68—Medicinal 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 an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
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    • A61K47/50—Medicinal 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
    • A61K47/51—Medicinal 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
    • A61K47/68—Medicinal 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 an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
    • A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
    • A61K47/68031—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being an auristatin
    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal 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
    • A61K47/51—Medicinal 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
    • A61K47/68—Medicinal 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 an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
    • A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
    • A61K47/68033—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being a maytansine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal 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
    • A61K47/51—Medicinal 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
    • A61K47/68—Medicinal 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 an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
    • A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
    • A61K47/6807—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug or compound being a sugar, nucleoside, nucleotide, nucleic acid, e.g. RNA antisense
    • A61K47/6809—Antibiotics, e.g. antitumor antibiotics anthracyclins, adriamycin, doxorubicin or daunomycin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal 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
    • A61K47/51—Medicinal 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
    • A61K47/68—Medicinal 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 an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
    • A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
    • A61K47/6811—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being a protein or peptide, e.g. transferrin or bleomycin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal 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
    • A61K47/51—Medicinal 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
    • A61K47/68—Medicinal 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 an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6889—Conjugates wherein the antibody being the modifying agent and wherein the linker, binder or spacer confers particular properties to the conjugates, e.g. peptidic enzyme-labile linkers or acid-labile linkers, providing for an acid-labile immuno conjugate wherein the drug may be released from its antibody conjugated part in an acidic, e.g. tumoural or environment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/18—Bridged systems

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  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Immunology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Medicinal Preparation (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Saccharide Compounds (AREA)
  • Indole Compounds (AREA)
  • Genetics & Genomics (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Biotechnology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
AU2014354643A 2013-11-27 2014-11-26 Hydrazinyl-pyrrolo compounds and methods for producing a conjugate Active AU2014354643B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361909897P 2013-11-27 2013-11-27
US61/909,897 2013-11-27
PCT/US2014/067746 WO2015081282A1 (en) 2013-11-27 2014-11-26 Hydrazinyl-pyrrolo compounds and methods for producing a conjugate

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AU2014354643A1 AU2014354643A1 (en) 2016-05-12
AU2014354643B2 true AU2014354643B2 (en) 2020-03-05

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US (5) US9493413B2 (https=)
EP (2) EP3074010B1 (https=)
JP (2) JP6745218B2 (https=)
KR (1) KR102320019B1 (https=)
CN (2) CN105744935B (https=)
AU (1) AU2014354643B2 (https=)
CA (2) CA3178867A1 (https=)
WO (1) WO2015081282A1 (https=)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2012205301B2 (en) 2011-01-14 2017-01-05 Redwood Bioscience, Inc. Aldehyde-tagged immunoglobulin polypeptides and method of use thereof
US9310374B2 (en) 2012-11-16 2016-04-12 Redwood Bioscience, Inc. Hydrazinyl-indole compounds and methods for producing a conjugate
MX379256B (es) * 2013-03-15 2025-03-10 Regeneron Pharma Moleculas biologicamente activas, conjugados de las mismas, y usos terapeuticos.
KR102252925B1 (ko) 2013-08-26 2021-05-18 리제너론 파마슈티칼스 인코포레이티드 마크롤라이드 디아스테레오머를 포함하는 약제학적 조성물, 이의 합성 방법 및 치료학적 용도
WO2015081282A1 (en) 2013-11-27 2015-06-04 Redwood Bioscience, Inc. Hydrazinyl-pyrrolo compounds and methods for producing a conjugate
WO2015187428A1 (en) * 2014-06-06 2015-12-10 Redwood Bioscience, Inc. Anti-her2 antibody-maytansine conjugates and methods of use thereof
EA034950B1 (ru) 2015-03-27 2020-04-09 Регенерон Фармасьютикалз, Инк. Производные майтанзиноида, их конъюгаты и способы использования
KR102783230B1 (ko) * 2015-11-09 2025-03-19 알.피.쉐러 테크놀러지즈 엘엘씨 항-cd22 항체-메이탄신 콘쥬게이트 및 그것의 사용 방법
WO2017132173A1 (en) 2016-01-25 2017-08-03 Regeneron Pharmaceuticals, Inc. Maytansinoid derivatives, conjugates thereof, and methods of use
EP3423105B1 (en) 2016-03-02 2021-05-05 Eisai R&D Management Co., Ltd. Eribulin-based antibody-drug conjugates and methods of use
AU2017257504A1 (en) 2016-04-26 2018-10-25 R.P. Scherer Technologies, Llc Antibody conjugates and methods of making and using the same
EP3458101B1 (en) * 2016-05-20 2020-12-30 H. Hoffnabb-La Roche Ag Protac antibody conjugates and methods of use
WO2018169953A1 (en) 2017-03-17 2018-09-20 R.P. Scherer Technologies, Llc Antibody conjugates and methods of making and using the same
CN108690033B (zh) * 2017-04-05 2021-01-01 中国科学院化学研究所 含黄酮类药物活性分子的荧光探针及其制备方法和应用
US11779592B2 (en) * 2017-08-14 2023-10-10 University Of North Texas Health Science Center Inhibition of NGLY1 for the treatment of cancer
CA3082912A1 (en) * 2017-12-11 2019-06-20 Triphase Accelerator U.S. Corporation Anti-cd22 antibody-maytansine conjugates, combinations, and methods of use thereof
WO2020096775A1 (en) 2018-11-09 2020-05-14 R.P. Scherer Technologies, Llc Sulfatase-cleavable linkers for antibody-drug conjugates
CN113874046B (zh) * 2019-01-23 2025-02-28 R.P.谢勒技术有限责任公司 用于抗体-药物缀合物的含有糖苷的肽接头
HUE060364T2 (hu) * 2019-03-29 2023-02-28 Medimmune Ltd Vegyületek és konjugátumaik
EP3976112A1 (en) * 2019-06-03 2022-04-06 Synaffix B.V. Acetal-based cleavable linkers
JP7252333B2 (ja) * 2019-09-29 2023-04-04 煙台邁百瑞国際生物医薬股▲ふん▼有限公司 酸法による抗体薬物複合体中間体の調製方法及びその応用
KR20220079576A (ko) 2019-10-04 2022-06-13 알.피.쉐러 테크놀러지즈 엘엘씨 항-cd25 항체-메이탄신 접합체 및 이의 사용 방법
EP4051319A4 (en) * 2019-10-31 2024-01-17 R.P. Scherer Technologies, LLC ANTI-CD37-MAYTANSINE ANTIBODY CONJUGATES AND METHODS OF USE THEREOF
KR20230122008A (ko) 2020-11-20 2023-08-22 알.피.쉐러 테크놀러지즈 엘엘씨 항체-약물 접합체를 위한 글리코시드 이중-절단 링커
AU2022207454A1 (en) 2021-01-15 2023-06-22 R.P. Scherer Technologies, Llc Camptothecine antibody-drug conjugates and methods of use thereof
AU2022245388A1 (en) * 2021-03-26 2023-10-05 Angiex, Inc. Maytansine-antibody conjugates and methods of using same
WO2023009759A2 (en) * 2021-07-30 2023-02-02 R.P. Scherer Technologies, Llc Antibody-drug conjugates and methods of use thereof

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030069430A1 (en) * 1997-09-05 2003-04-10 Davis Stephen Thomas Substituted oxindole derivatives as protein tyrosine and as protein serine/threonine kinase inhibitors and compositions and methods of treating chemotherapy and radiation therapy side effects
US20050153989A1 (en) * 2004-01-13 2005-07-14 Ambit Biosciences Corporation Pyrrolopyrimidine derivatives and analogs and their use in the treatment and prevention of diseases
US20060116417A1 (en) * 2004-10-25 2006-06-01 Jyun-Hung Chen Thrombopoietin activity modulating compounds and methods
EP1731506A1 (en) * 2004-03-12 2006-12-13 Shenyang Pharmaceutical University 5-hydroxyindole-3-carboxylates derivatives and their use
US20070275962A1 (en) * 2003-09-10 2007-11-29 Gpc Biotech Ag Heterobicyclic Compounds as Pharmaceutically Active Agents
US20080031823A1 (en) * 2002-09-04 2008-02-07 Bornhop Darryl J Agents for therapy efficacy monitoring and deep tissue imaging
US7754884B2 (en) * 2005-01-03 2010-07-13 Vanderbilt University Targeted, NIR imaging agents for therapy efficacy monitoring, deep tissue disease demarcation and deep tissue imaging
WO2011099718A1 (en) * 2010-02-11 2011-08-18 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2014074218A1 (en) * 2012-11-12 2014-05-15 Redwood Bioscience, Inc. Compounds and methods for producing a conjugate
WO2014078566A1 (en) * 2012-11-16 2014-05-22 Redwood Bioscience, Inc. Hydrazinyl-indole compounds and conjugates
WO2015187428A1 (en) * 2014-06-06 2015-12-10 Redwood Bioscience, Inc. Anti-her2 antibody-maytansine conjugates and methods of use thereof

Family Cites Families (117)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES324609A1 (es) 1966-03-24 1966-12-16 Patronato De Investigacien Cie Procedimiento para la preparaciën de indolil-alquil hidrazinas
US4179337A (en) 1973-07-20 1979-12-18 Davis Frank F Non-immunogenic polypeptides
US4816567A (en) 1983-04-08 1989-03-28 Genentech, Inc. Recombinant immunoglobin preparations
JPS61134325A (ja) 1984-12-04 1986-06-21 Teijin Ltd ハイブリツド抗体遺伝子の発現方法
US5618920A (en) 1985-11-01 1997-04-08 Xoma Corporation Modular assembly of antibody genes, antibodies prepared thereby and use
US5225539A (en) 1986-03-27 1993-07-06 Medical Research Council Recombinant altered antibodies and methods of making altered antibodies
GB8607679D0 (en) 1986-03-27 1986-04-30 Winter G P Recombinant dna product
DE3815826A1 (de) 1988-05-09 1989-11-23 Henkel Kgaa Verfahren zur herstellung von vicinal diacyloxysubstituierten verbindungen
US5470829A (en) 1988-11-17 1995-11-28 Prisell; Per Pharmaceutical preparation
EP0401384B1 (en) 1988-12-22 1996-03-13 Kirin-Amgen, Inc. Chemically modified granulocyte colony stimulating factor
US5530101A (en) 1988-12-28 1996-06-25 Protein Design Labs, Inc. Humanized immunoglobulins
US5089261A (en) 1989-01-23 1992-02-18 Cetus Corporation Preparation of a polymer/interleukin-2 conjugate
US5122614A (en) 1989-04-19 1992-06-16 Enzon, Inc. Active carbonates of polyalkylene oxides for modification of polypeptides
EP0470128B2 (en) 1989-04-19 2003-08-13 Enzon, Inc. Active carbonates of polyalkylene oxides for modification of polypeptides
US5324844A (en) 1989-04-19 1994-06-28 Enzon, Inc. Active carbonates of polyalkylene oxides for modification of polypeptides
IL90193A (en) 1989-05-04 1993-02-21 Biomedical Polymers Int Polurethane-based polymeric materials and biomedical articles and pharmaceutical compositions utilizing the same
US5650388A (en) 1989-11-22 1997-07-22 Enzon, Inc. Fractionated polyalkylene oxide-conjugated hemoglobin solutions
US5312808A (en) 1989-11-22 1994-05-17 Enzon, Inc. Fractionation of polyalkylene oxide-conjugated hemoglobin solutions
GB8928874D0 (en) 1989-12-21 1990-02-28 Celltech Ltd Humanised antibodies
NL194941C (nl) 1990-02-15 2003-08-04 Cordis Corp Werkwijze voor het aanbrengen van een fysiologisch actieve verbinding op een substraatoppervlak.
US5275838A (en) 1990-02-28 1994-01-04 Massachusetts Institute Of Technology Immobilized polyethylene oxide star molecules for bioapplications
US5171264A (en) 1990-02-28 1992-12-15 Massachusetts Institute Of Technology Immobilized polyethylene oxide star molecules for bioapplications
US5219564A (en) 1990-07-06 1993-06-15 Enzon, Inc. Poly(alkylene oxide) amino acid copolymers and drug carriers and charged copolymers based thereon
WO1992000748A1 (en) 1990-07-06 1992-01-23 Enzon, Inc. Poly(alkylene oxide) amino acid copolymers and drug carriers and charged copolymers based thereon
JPH0498240A (ja) * 1990-08-17 1992-03-30 Konica Corp ハロゲン化銀写真感光材料
FR2672053B1 (fr) 1991-01-30 1993-04-23 Atochem Polyether bloc amides, leur procede de synthese.
EP0531472B1 (en) 1991-03-06 2003-08-13 MERCK PATENT GmbH Humanized monoclonal antibodies
FR2673946B1 (fr) 1991-03-15 1993-05-28 Atochem Polyether bloc amides, leur procede de synthese.
WO1992016555A1 (en) 1991-03-18 1992-10-01 Enzon, Inc. Hydrazine containing conjugates of polypeptides and glycopolypeptides with polymers
TW197439B (https=) 1991-04-04 1993-01-01 Ueno Pharmaceutics Applic Res Co Ltd
EP0519596B1 (en) 1991-05-17 2005-02-23 Merck & Co. Inc. A method for reducing the immunogenicity of antibody variable domains
US5281698A (en) 1991-07-23 1994-01-25 Cetus Oncology Corporation Preparation of an activated polymer ester for protein conjugation
AU669124B2 (en) 1991-09-18 1996-05-30 Kyowa Hakko Kirin Co., Ltd. Process for producing humanized chimera antibody
ES2136092T3 (es) 1991-09-23 1999-11-16 Medical Res Council Procedimientos para la produccion de anticuerpos humanizados.
US5283253A (en) 1991-09-23 1994-02-01 Florida State University Furyl or thienyl carbonyl substituted taxanes and pharmaceutical compositions containing them
WO1993010076A1 (en) 1991-11-22 1993-05-27 The University Of Mississippi Synthesis and optical resolution of the taxol side chain and related compounds
GB9125979D0 (en) 1991-12-06 1992-02-05 Wellcome Found Antibody
AU660534B2 (en) 1992-02-13 1995-06-29 Novo Nordisk A/S Polyethylene or polypropylene glycol containing polymer
ATE171472T1 (de) 1992-02-19 1998-10-15 Schering Corp Klonierung und expression von humanisierten monoklonalen antikörpern gegen menschliches interleukin-4
US5200534A (en) 1992-03-13 1993-04-06 University Of Florida Process for the preparation of taxol and 10-deacetyltaxol
JPH08500973A (ja) 1992-05-21 1996-02-06 ザ ペン ステイト リサーチ ファウンデーション タキソール、関連タキサン及び他の新規な抗癌／抗ウイルス性化合物原料としてのイチイ培養組織
US5274137A (en) 1992-06-23 1993-12-28 Nicolaou K C Intermediates for preparation of taxols
US5294637A (en) 1992-07-01 1994-03-15 Bristol-Myers Squibb Company Fluoro taxols
US5202448A (en) 1992-08-14 1993-04-13 Napro Biotherapeutics, Inc. Processes of converting taxanes into baccatin III
US5614549A (en) 1992-08-21 1997-03-25 Enzon, Inc. High molecular weight polymer-based prodrugs
AU5006993A (en) 1992-08-21 1994-03-15 Enzon, Inc. Novel attachment of polyalkylene oxides to bio-effecting substances
US5639641A (en) 1992-09-09 1997-06-17 Immunogen Inc. Resurfacing of rodent antibodies
CA2100808A1 (en) 1992-10-01 1994-04-02 Vittorio Farina Deoxy paclitaxels
FR2696463B1 (fr) 1992-10-05 1994-11-25 Rhone Poulenc Rorer Sa Procédé d'obtention de la désacétyl-10 baccatine III.
FR2696461B1 (fr) 1992-10-05 1994-11-10 Rhone Poulenc Rorer Sa Nouveaux dérivés d'analogues du taxol, leur préparation et les compositions qui les contiennent.
FR2696464B1 (fr) 1992-10-05 1994-11-10 Rhone Poulenc Rorer Sa Nouveau procédé d'estérification de la baccatine III et de la désacétyl-10 baccatine III.
FR2696462B1 (fr) 1992-10-05 1994-11-25 Rhone Poulenc Rorer Sa Procédé d'obtention de la désacétyl-10 baccatine III.
FR2696458B1 (fr) 1992-10-05 1994-11-10 Rhone Poulenc Rorer Sa Procédé de préparation de dérivés du taxane.
US5279949A (en) 1992-12-07 1994-01-18 Board Of Trustees Operating Michigan State University Process for the isolation and purification of taxol and taxanes from Taxus spp
US5298643A (en) 1992-12-22 1994-03-29 Enzon, Inc. Aryl imidate activated polyalkylene oxides
US5349001A (en) 1993-01-19 1994-09-20 Enzon, Inc. Cyclic imide thione activated polyalkylene oxides
US5321095A (en) 1993-02-02 1994-06-14 Enzon, Inc. Azlactone activated polyalkylene oxides
WO1994028937A1 (en) 1993-06-16 1994-12-22 Enzon, Inc. Conjugated biodhesives
US5824701A (en) 1993-10-20 1998-10-20 Enzon, Inc. Taxane-based prodrugs
US5880131A (en) 1993-10-20 1999-03-09 Enzon, Inc. High molecular weight polymer-based prodrugs
US5965566A (en) 1993-10-20 1999-10-12 Enzon, Inc. High molecular weight polymer-based prodrugs
US5840900A (en) 1993-10-20 1998-11-24 Enzon, Inc. High molecular weight polymer-based prodrugs
US5643575A (en) 1993-10-27 1997-07-01 Enzon, Inc. Non-antigenic branched polymer conjugates
US5605976A (en) 1995-05-15 1997-02-25 Enzon, Inc. Method of preparing polyalkylene oxide carboxylic acids
US5919455A (en) 1993-10-27 1999-07-06 Enzon, Inc. Non-antigenic branched polymer conjugates
US5446090A (en) 1993-11-12 1995-08-29 Shearwater Polymers, Inc. Isolatable, water soluble, and hydrolytically stable active sulfones of poly(ethylene glycol) and related polymers for modification of surfaces and molecules
US5415869A (en) 1993-11-12 1995-05-16 The Research Foundation Of State University Of New York Taxol formulation
US5618528A (en) 1994-02-28 1997-04-08 Sterling Winthrop Inc. Biologically compatible linear block copolymers of polyalkylene oxide and peptide units
WO1995033490A1 (en) 1994-06-02 1995-12-14 Enzon, Inc. Method of solubilizing substantially water insoluble materials
US5730990A (en) 1994-06-24 1998-03-24 Enzon, Inc. Non-antigenic amine derived polymers and polymer conjugates
US5824784A (en) 1994-10-12 1998-10-20 Amgen Inc. N-terminally chemically modified protein compositions and methods
US5599902A (en) 1994-11-10 1997-02-04 Arizona Board Of Regents Acting On Behalf Of Arizona State University Cancer inhibitory peptides
US5932462A (en) 1995-01-10 1999-08-03 Shearwater Polymers, Inc. Multiarmed, monofunctional, polymer for coupling to molecules and surfaces
US5705154A (en) 1995-03-08 1998-01-06 Schering Corporation Humanized monoclonal antibodies against human interleukin-4
WO1996033212A1 (fr) 1995-04-21 1996-10-24 Teikoku Hormone Mfg. Co., Ltd. Nouveaux derives peptidiques
US5756593A (en) 1995-05-15 1998-05-26 Enzon, Inc. Method of preparing polyalkyene oxide carboxylic acids
US5672662A (en) 1995-07-07 1997-09-30 Shearwater Polymers, Inc. Poly(ethylene glycol) and related polymers monosubstituted with propionic or butanoic acids and functional derivatives thereof for biotechnical applications
US5919442A (en) 1995-08-11 1999-07-06 Dendritech, Inc. Hyper comb-branched polymer conjugates
ATE330644T1 (de) 1995-12-18 2006-07-15 Angiotech Biomaterials Corp Vernetzten polymerisatmassen und verfahren für ihre verwendung
EP1731174A3 (en) 1996-08-02 2007-01-17 Ortho-McNeil Pharmaceutical, Inc. Polypeptides having a covalently bound N-terminal polyethylene glycol via hydrazone or oxime bond
WO1998008833A1 (en) 1996-08-26 1998-03-05 Bristol-Myers Squibb Company Sulfenamide taxane derivatives
US6214966B1 (en) 1996-09-26 2001-04-10 Shearwater Corporation Soluble, degradable poly(ethylene glycol) derivatives for controllable release of bound molecules into solution
EP0961619A4 (en) 1996-09-27 2001-09-26 Bristol Myers Squibb Co HYDROLYSABLE DRUGS FOR THE RELEASE OF ANTI-CANCER DRUGS IN METASTATIC CELLS
AU4966597A (en) 1996-11-19 1998-06-10 Daiichi Pharmaceutical Co., Ltd. Taxol derivatives
US5977386A (en) 1996-12-24 1999-11-02 Bristol-Myers Squibb Company 6-thio-substituted paclitaxels
JP3957765B2 (ja) 1997-04-07 2007-08-15 ジェネンテク・インコーポレイテッド 抗ｖｅｇｆ抗体
EP2338915A3 (en) 1997-04-07 2011-10-12 Genentech, Inc. Anti-VEGF antibodies
EP0981548A4 (en) 1997-04-30 2005-11-23 Enzon Inc GLYCOSYLATABLE SINGLE CHAIN ANTIGEN-BINDING PROTEINS, MANUFACTURE AND USE THEREOF
US5990237A (en) 1997-05-21 1999-11-23 Shearwater Polymers, Inc. Poly(ethylene glycol) aldehyde hydrates and related polymers and applications in modifying amines
IL133585A0 (en) 1997-06-20 2001-04-30 Baker Norton Pharma Soluble prodrugs of paclitaxel
US7288665B1 (en) 1997-08-18 2007-10-30 Florida State University Process for selective derivatization of taxanes
JPH1192468A (ja) 1997-09-17 1999-04-06 Yakult Honsha Co Ltd 新規なタキサン誘導体
WO1999018113A1 (fr) 1997-10-08 1999-04-15 Bio Research Corporation Of Yokohama Derives taxoides et leur procede de production
US6011042A (en) 1997-10-10 2000-01-04 Enzon, Inc. Acyl polymeric derivatives of aromatic hydroxyl-containing compounds
US6111107A (en) 1997-11-20 2000-08-29 Enzon, Inc. High yield method for stereoselective acylation of tertiary alcohols
WO1999030727A1 (en) 1997-12-17 1999-06-24 Enzon, Inc. Polymeric prodrugs of amino- and hydroxyl-containing bioactive agents
US6180095B1 (en) 1997-12-17 2001-01-30 Enzon, Inc. Polymeric prodrugs of amino- and hydroxyl-containing bioactive agents
US5985263A (en) 1997-12-19 1999-11-16 Enzon, Inc. Substantially pure histidine-linked protein polymer conjugates
US5965119A (en) 1997-12-30 1999-10-12 Enzon, Inc. Trialkyl-lock-facilitated polymeric prodrugs of amino-containing bioactive agents
DK1411075T3 (da) 1998-03-12 2008-10-27 Nektar Therapeutics Al Corp Fremgangsmåde til fremstilling af polymerkonjugater
US6153655A (en) 1998-04-17 2000-11-28 Enzon, Inc. Terminally-branched polymeric linkers and polymeric conjugates containing the same
DE69930328T2 (de) 1998-08-27 2006-12-14 Spirogen Ltd., Ryde Dimere Pyrrolobenzodiazepine
US6323315B1 (en) 1999-09-10 2001-11-27 Basf Aktiengesellschaft Dolastatin peptides
CN1284603C (zh) 1999-10-08 2006-11-15 内科塔治疗亚拉巴马公司 杂双官能聚乙二醇衍生物和它们的制备方法
US6570040B2 (en) 2000-03-16 2003-05-27 The Regents Of The University Of California Chemoselective ligation
EE200300089A (et) 2000-09-08 2005-02-15 Gryphon Therapeutics, Inc. Sünteetilised erütropoeesi stimuleerivad valgud, nende valmistamismeetodid ning kasutamine
AU2003264009A1 (en) 2002-08-15 2004-03-03 Epitomics, Inc. Humanized rabbit antibodies
EP1391213A1 (en) 2002-08-21 2004-02-25 Boehringer Ingelheim International GmbH Compositions and methods for treating cancer using maytansinoid CD44 antibody immunoconjugates and chemotherapeutic agents
EP1651659A4 (en) 2003-08-07 2008-09-17 Epitomics Inc METHOD FOR HUMANIZATION OF MONOCLONAL RABBIT ANTIBODIES
US20050153371A1 (en) * 2004-01-07 2005-07-14 Ambit Biosciences Corporation Conjugated small molecules
JP4806680B2 (ja) 2004-05-19 2011-11-02 メダレックス インコーポレイテッド 自己犠牲リンカー及び薬剤複合体
JP5171621B2 (ja) 2005-07-07 2013-03-27 シアトル ジェネティックス， インコーポレイテッド フェニルアラニン側鎖修飾をｃ末端に有するモノメチルバリン化合物
US7985783B2 (en) 2006-09-21 2011-07-26 The Regents Of The University Of California Aldehyde tags, uses thereof in site-specific protein modification
US8729232B2 (en) 2008-03-27 2014-05-20 The Regents Of The University Of California Aldehyde tags, uses thereof in site-specific protein modification
JP2009298735A (ja) * 2008-06-13 2009-12-24 Univ Of Tokyo 修飾タンパク質の製造方法と該製造方法で得られる修飾タンパク質及びタンパク質修飾キット
AR078471A1 (es) 2009-10-02 2011-11-09 Sanofi Aventis COMPUESTOS MAITANSINOIDES Y EL USO DE ESTOS PARA PREPARAR CONJUGADOS CON UN ANTICUERPO LOS CUALES SE UTILIZAN COMO AGENTES ANTICANCERIGENOS Y EL PROCEDIMIENTO DE PREPARACIoN DE ESTOS CONJUGADOS
WO2015081282A1 (en) * 2013-11-27 2015-06-04 Redwood Bioscience, Inc. Hydrazinyl-pyrrolo compounds and methods for producing a conjugate

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030069430A1 (en) * 1997-09-05 2003-04-10 Davis Stephen Thomas Substituted oxindole derivatives as protein tyrosine and as protein serine/threonine kinase inhibitors and compositions and methods of treating chemotherapy and radiation therapy side effects
US20080031823A1 (en) * 2002-09-04 2008-02-07 Bornhop Darryl J Agents for therapy efficacy monitoring and deep tissue imaging
US20070275962A1 (en) * 2003-09-10 2007-11-29 Gpc Biotech Ag Heterobicyclic Compounds as Pharmaceutically Active Agents
US20050153989A1 (en) * 2004-01-13 2005-07-14 Ambit Biosciences Corporation Pyrrolopyrimidine derivatives and analogs and their use in the treatment and prevention of diseases
EP1731506A1 (en) * 2004-03-12 2006-12-13 Shenyang Pharmaceutical University 5-hydroxyindole-3-carboxylates derivatives and their use
US20060116417A1 (en) * 2004-10-25 2006-06-01 Jyun-Hung Chen Thrombopoietin activity modulating compounds and methods
US7754884B2 (en) * 2005-01-03 2010-07-13 Vanderbilt University Targeted, NIR imaging agents for therapy efficacy monitoring, deep tissue disease demarcation and deep tissue imaging
WO2011099718A1 (en) * 2010-02-11 2011-08-18 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2014074218A1 (en) * 2012-11-12 2014-05-15 Redwood Bioscience, Inc. Compounds and methods for producing a conjugate
WO2014078566A1 (en) * 2012-11-16 2014-05-22 Redwood Bioscience, Inc. Hydrazinyl-indole compounds and conjugates
US20140141025A1 (en) * 2012-11-16 2014-05-22 Redwood Bioscience, Inc. Hydrazinyl-indole compounds and methods for producing a conjugate
WO2015187428A1 (en) * 2014-06-06 2015-12-10 Redwood Bioscience, Inc. Anti-her2 antibody-maytansine conjugates and methods of use thereof

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