CA2829736C - N-carboxyalkylauristatins and use thereof - Google Patents

N-carboxyalkylauristatins and use thereof Download PDF

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Publication number
CA2829736C
CA2829736C CA2829736A CA2829736A CA2829736C CA 2829736 C CA2829736 C CA 2829736C CA 2829736 A CA2829736 A CA 2829736A CA 2829736 A CA2829736 A CA 2829736A CA 2829736 C CA2829736 C CA 2829736C
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CA
Canada
Prior art keywords
stands
methyl
formula
compound
phenyl
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Active
Application number
CA2829736A
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English (en)
French (fr)
Other versions
CA2829736A1 (en
Inventor
Hans-Georg Lerchen
Sherif El Sheikh
Beatrix Stelte-Ludwig
Joachim Schuhmacher
Mark Gnoth
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.)
Seagen Inc
Original Assignee
Seattle Genetics Inc
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 Seattle Genetics Inc filed Critical Seattle Genetics Inc
Publication of CA2829736A1 publication Critical patent/CA2829736A1/en
Application granted granted Critical
Publication of CA2829736C publication Critical patent/CA2829736C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • A61K38/04Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/07Tetrapeptides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0205Peptides 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)3-C(=0)-, e.g. statine or derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • 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
    • A61K47/64Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
    • A61K47/6415Toxins or lectins, e.g. clostridial toxins or Pseudomonas exotoxins

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Immunology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
CA2829736A 2011-03-16 2012-03-12 N-carboxyalkylauristatins and use thereof Active CA2829736C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP11158481.9 2011-03-16
EP11158481 2011-03-16
PCT/EP2012/054294 WO2012123423A1 (de) 2011-03-16 2012-03-12 N-carboxyalkyl-auristatine und ihre verwendung

Publications (2)

Publication Number Publication Date
CA2829736A1 CA2829736A1 (en) 2012-09-20
CA2829736C true CA2829736C (en) 2020-07-21

Family

ID=45812791

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2829736A Active CA2829736C (en) 2011-03-16 2012-03-12 N-carboxyalkylauristatins and use thereof

Country Status (7)

Country Link
US (1) US9029406B2 (https=)
EP (1) EP2686336B1 (https=)
JP (2) JP6023097B2 (https=)
CN (1) CN103764667B (https=)
CA (1) CA2829736C (https=)
ES (1) ES2543888T3 (https=)
WO (1) WO2012123423A1 (https=)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8987209B2 (en) 2010-09-29 2015-03-24 Seattle Genetics, Inc. N-carboxyalkyl-auristatin and the use thereof
KR102023496B1 (ko) * 2011-04-21 2019-09-20 시애틀 지네틱스, 인크. 신규 결합제-약물 콘주게이트 (adc) 및 그의 용도
MY168297A (en) 2011-11-17 2018-10-23 Pfizer Cytotoxic Peptides and Antibody Drug Conjugates Thereof
US10226535B2 (en) 2012-12-10 2019-03-12 Mersana Therapeutics, Inc. Auristatin compounds and conjugates thereof
FR3005051A1 (fr) * 2013-04-25 2014-10-31 Pf Medicament Derives de la dolastatine 10 et d'auristatines
US10208125B2 (en) 2013-07-15 2019-02-19 University of Pittsburgh—of the Commonwealth System of Higher Education Anti-mucin 1 binding agents and uses thereof
BR112016012538A2 (pt) 2013-12-17 2017-09-26 Novartis Ag peptídeos citotóxicos e conjugados dos mesmos
RU2729194C2 (ru) 2013-12-27 2020-08-05 Займворкс Инк. Сульфонамидсодержащие связывающие системы для лекарственных конъюгатов
RU2692563C2 (ru) 2014-04-25 2019-06-25 Пьер Фабр Медикамент Конъюгат антитела против igf-1r с лекарственным средством и его применение для лечения рака
BR112016024363A2 (pt) 2014-04-25 2017-10-10 Pf Medicament conjugado de anticorpo-fármaco e seu uso para tratamento de câncer
CN106573956A (zh) 2014-06-13 2017-04-19 诺华股份有限公司 澳瑞他汀衍生物及其缀合物
EP3554544A4 (en) 2016-12-16 2020-07-29 Bluefin Biomedicine, Inc. ANTI-PROTEIN 1 ANTIBODY CONTAINING AN ANTI-CUB DOMAIN (CDCP1), ANTIBODY-DRUG CONJUGATES AND THEIR METHODS OF USE
CN111393346B (zh) * 2020-06-02 2020-08-25 凯莱英生命科学技术(天津)有限公司 N-Boc-Dolaproine及Boc-Dap DCHA的合成方法
MX2024002571A (es) 2021-09-03 2024-03-20 Toray Industries Composicion farmaceutica para tratamiento y/o prevencion de cancer.

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5663149A (en) 1994-12-13 1997-09-02 Arizona Board Of Regents Acting On Behalf Of Arizona State University Human cancer inhibitory pentapeptide heterocyclic and halophenyl amides
WO1999035164A1 (en) 1998-01-09 1999-07-15 Arizona Board Of Regents, A Body Corporate, Acting On Behalf Of Arizona State University Anti-cryptococcal peptides
CA2370245A1 (en) 1999-05-14 2000-11-23 Boehringer Ingelheim Pharmaceuticals, Inc. Enzyme-activated anti-tumor prodrug compounds
US6323315B1 (en) 1999-09-10 2001-11-27 Basf Aktiengesellschaft Dolastatin peptides
US6884869B2 (en) 2001-04-30 2005-04-26 Seattle Genetics, Inc. Pentapeptide compounds and uses related thereto
US6737409B2 (en) * 2001-07-19 2004-05-18 Hoffmann-La Roche Inc. Dolastatin 10 derivatives
WO2003026577A2 (en) 2001-09-24 2003-04-03 Seattle Genetics, Inc. P-amidobenzylethers in drug delivery agents
SI1545613T1 (sl) 2002-07-31 2011-11-30 Seattle Genetics Inc Avristatinski konjugati in njihova uporaba za zdravljenje raka avtoimunske bolezni ali infekcijskebolezni
US7498298B2 (en) * 2003-11-06 2009-03-03 Seattle Genetics, Inc. Monomethylvaline compounds capable of conjugation to ligands
WO2006132670A2 (en) 2004-11-12 2006-12-14 Seattle Genetics, Inc. Auristatins having an aminobenzoic acid unit at the n terminus
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
US8871720B2 (en) 2005-07-07 2014-10-28 Seattle Genetics, Inc. Monomethylvaline compounds having phenylalanine carboxy modifications at the C-terminus
KR20140116546A (ko) 2006-10-27 2014-10-02 제넨테크, 인크. 항체 및 면역접합체 및 이들의 용도
EP2265283B1 (en) 2008-03-18 2014-09-03 Seattle Genetics, Inc. Auristatin drug linker conjugates
CN103200950B (zh) * 2010-06-10 2016-03-16 西雅图基因公司 新颖的耳他汀衍生物及其用途
US8987209B2 (en) 2010-09-29 2015-03-24 Seattle Genetics, Inc. N-carboxyalkyl-auristatin and the use thereof
KR102023496B1 (ko) 2011-04-21 2019-09-20 시애틀 지네틱스, 인크. 신규 결합제-약물 콘주게이트 (adc) 및 그의 용도

Also Published As

Publication number Publication date
CA2829736A1 (en) 2012-09-20
EP2686336B1 (de) 2015-05-06
US9029406B2 (en) 2015-05-12
WO2012123423A1 (de) 2012-09-20
JP6023097B2 (ja) 2016-11-09
CN103764667B (zh) 2017-06-20
CN103764667A (zh) 2014-04-30
HK1191034A1 (en) 2014-07-18
US20140080763A1 (en) 2014-03-20
JP2016185987A (ja) 2016-10-27
ES2543888T3 (es) 2015-08-25
EP2686336A1 (de) 2014-01-22
JP2014515735A (ja) 2014-07-03

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