CA2801971C - Novel auristatin derivatives and their use - Google Patents

Novel auristatin derivatives and their use Download PDF

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Publication number
CA2801971C
CA2801971C CA2801971A CA2801971A CA2801971C CA 2801971 C CA2801971 C CA 2801971C CA 2801971 A CA2801971 A CA 2801971A CA 2801971 A CA2801971 A CA 2801971A CA 2801971 C CA2801971 C CA 2801971C
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CA
Canada
Prior art keywords
compound
methyl
formula
salt
methoxy
Prior art date
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Active
Application number
CA2801971A
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English (en)
French (fr)
Other versions
CA2801971A1 (en
Inventor
Hans-Georg Lerchen
Beatrix Stelte-Ludwig
Sven Golfier
Joachim Schuhmacher
Ursula Krenz
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Seagen Inc
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Seattle Genetics Inc
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Publication of CA2801971A1 publication Critical patent/CA2801971A1/en
Application granted granted Critical
Publication of CA2801971C publication Critical patent/CA2801971C/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/02—Linear peptides containing at least one abnormal peptide link
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/08—Peptides having 5 to 11 amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • 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
    • C07K5/0205—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)3-C(=0)-, e.g. statine or derivatives thereof
    • 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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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
CA2801971A 2010-06-10 2011-06-06 Novel auristatin derivatives and their use Active CA2801971C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP10165550.4 2010-06-10
EP10165550 2010-06-10
EP11158464 2011-03-16
EP11158464.5 2011-03-16
PCT/EP2011/059300 WO2011154359A1 (de) 2010-06-10 2011-06-06 Neue auristatin-derivate und ihre verwendung

Publications (2)

Publication Number Publication Date
CA2801971A1 CA2801971A1 (en) 2011-12-15
CA2801971C true CA2801971C (en) 2018-07-24

Family

ID=44275637

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2801971A Active CA2801971C (en) 2010-06-10 2011-06-06 Novel auristatin derivatives and their use

Country Status (7)

Country Link
US (1) US8722629B2 (https=)
EP (1) EP2579887B1 (https=)
JP (1) JP5791707B2 (https=)
CN (1) CN103200950B (https=)
CA (1) CA2801971C (https=)
ES (1) ES2528956T3 (https=)
WO (1) WO2011154359A1 (https=)

Families Citing this family (24)

* 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
US9029406B2 (en) 2011-03-16 2015-05-12 Seattle Genetics, Inc N-carboxyalkylauristatins and 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
AU2012351685A1 (en) * 2011-12-14 2014-07-03 Seattle Genetics, Inc. FGFR antibody drug conjugates (ADCs) and the use thereof
US10226535B2 (en) 2012-12-10 2019-03-12 Mersana Therapeutics, Inc. Auristatin compounds and conjugates thereof
PL2968440T3 (pl) 2013-03-15 2019-12-31 Zymeworks Inc. Związki cytotoksyczne i antymitotyczne oraz sposoby ich stosowania
FR3005051A1 (fr) * 2013-04-25 2014-10-31 Pf Medicament Derives de la dolastatine 10 et d'auristatines
RU2729194C2 (ru) 2013-12-27 2020-08-05 Займворкс Инк. Сульфонамидсодержащие связывающие системы для лекарственных конъюгатов
AU2014373640B2 (en) 2013-12-27 2018-08-30 Var2 Pharmaceuticals Aps VAR2CSA-drug conjugates
BR112016024363A2 (pt) 2014-04-25 2017-10-10 Pf Medicament conjugado de anticorpo-fármaco e seu uso para tratamento de câncer
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
AU2015318556C1 (en) * 2014-09-17 2021-01-07 Zymeworks Bc Inc. Cytotoxic and anti-mitotic compounds, and methods of using the same
CN106279352B (zh) 2015-05-29 2020-05-22 上海新理念生物医药科技有限公司 海兔毒素10的衍生物及其应用
WO2017161206A1 (en) 2016-03-16 2017-09-21 Halozyme, Inc. Conjugates containing conditionally active antibodies or antigen-binding fragments thereof, and methods of use
US10517958B2 (en) 2016-10-04 2019-12-31 Zymeworks Inc. Compositions and methods for the treatment of platinum-drug resistant cancer
CN108690119B (zh) * 2018-06-04 2022-04-19 莎穆(上海)生物科技有限公司 一种伊文思蓝修饰的多肽类前药及其制备和应用
JP7717832B2 (ja) 2021-04-10 2025-08-04 ジェンマブ エー／エス Ｆｏｌｒ１結合剤、そのコンジュゲートおよびこれを使用する方法
WO2022226317A1 (en) 2021-04-23 2022-10-27 Profoundbio Us Co. Anti-cd70 antibodies, conjugates thereof and methods of using the same
TW202320857A (zh) 2021-07-06 2023-06-01 美商普方生物製藥美國公司 連接子、藥物連接子及其結合物及其使用方法
MX2024002571A (es) 2021-09-03 2024-03-20 Toray Industries Composicion farmaceutica para tratamiento y/o prevencion de cancer.
AU2024353316A1 (en) 2023-09-26 2026-03-26 Genmab A/S Ptk7 binding agents, conjugates thereof and methods of using the same
WO2025149661A1 (en) 2024-01-10 2025-07-17 Genmab A/S Slitrk6 binding agents, conjugates thereof and methods of using the same
WO2025181219A1 (en) 2024-02-29 2025-09-04 Genmab A/S Egfr and c-met bispecific binding agents, conjugates thereof and methods of using the same

Family Cites Families (16)

* 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
CA2462653C (en) * 2001-11-07 2016-06-07 Aya Jakobovits Nucleic acid and corresponding protein entitled 161p2f10b useful in treatment and detection of cancer
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
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
HK1184363A1 (en) 2014-01-24
JP2013533228A (ja) 2013-08-22
US20130157960A1 (en) 2013-06-20
CN103200950B (zh) 2016-03-16
CA2801971A1 (en) 2011-12-15
WO2011154359A1 (de) 2011-12-15
ES2528956T3 (es) 2015-02-13
EP2579887A1 (de) 2013-04-17
EP2579887B1 (de) 2014-11-12
CN103200950A (zh) 2013-07-10
JP5791707B2 (ja) 2015-10-07
US8722629B2 (en) 2014-05-13

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