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
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.)
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
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.)
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Publication date
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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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Anticipated expiration legal-status Critical

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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)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (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 (enExample)
EP (1) EP2579887B1 (enExample)
JP (1) JP5791707B2 (enExample)
CN (1) CN103200950B (enExample)
CA (1) CA2801971C (enExample)
ES (1) ES2528956T3 (enExample)
WO (1) WO2011154359A1 (enExample)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2553874T3 (es) 2010-09-29 2015-12-14 Seattle Genetics, Inc. N-Carboxialquil-auristatinas y su uso
CA2829736C (en) 2011-03-16 2020-07-21 Seattle Genetics, Inc. N-carboxyalkylauristatins and use thereof
EP3501546A3 (de) * 2011-04-21 2019-09-18 Seattle Genetics, Inc. Cystein-wirkstoff konjugate und ihre verwendung
TWI589592B (zh) 2011-11-17 2017-07-01 輝瑞股份有限公司 胞毒性肽類以及其抗體藥物共軛體
MX2014007121A (es) * 2011-12-14 2014-09-04 Seattle Genetics Inc Nuevos conjugados de principio activo-ligante (adc) y su uso.
WO2014093379A1 (en) 2012-12-10 2014-06-19 Mersana Therapeutics, Inc. Auristatin compounds and conjugates thereof
US9522876B2 (en) 2013-03-15 2016-12-20 Zymeworks Inc. Cytotoxic and anti-mitotic compounds, and methods of using the same
FR3005051A1 (fr) * 2013-04-25 2014-10-31 Pf Medicament Derives de la dolastatine 10 et d'auristatines
ES2916722T3 (es) 2013-12-27 2022-07-05 Zymeworks Inc Sistemas de enlace que contienen sulfonamida para conjugados de fármacos
SG11201605260VA (en) 2013-12-27 2016-07-28 Zymeworks Inc Var2csa-drug conjugates
EP3134124B1 (en) 2014-04-25 2019-02-20 Pierre Fabre Medicament Igf-1r antibody-drug-conjugate and its use for the treatment of cancer
CN106470708B (zh) 2014-04-25 2019-12-31 皮埃尔法布雷医药公司 抗体-药物-缀合物和其用于治疗癌症的用途
EP3194421B1 (en) 2014-09-17 2021-11-03 Zymeworks 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
EP4319820A1 (en) 2021-04-10 2024-02-14 Profoundbio Us Co. Folr1 binding agents, conjugates thereof and methods of using the same
JP7742892B2 (ja) 2021-04-23 2025-09-22 ジェンマブ エー／エス 抗ｃｄ７０抗体、そのコンジュゲートおよびこれを使用する方法
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
EP4400121A1 (en) 2021-09-03 2024-07-17 Toray Industries, Inc. Pharmaceutical composition for treating and/or preventing cancer
WO2025072406A1 (en) 2023-09-26 2025-04-03 Profoundbio Us Co. Ptk7 binding agents, conjugates thereof and methods of using the same
TW202547866A (zh) 2024-01-10 2025-12-16 丹麥商珍美寶股份有限公司 Ｓｌｉｔｒｋ６結合劑、其共軛物及使用彼之方法
US20250381289A1 (en) 2024-02-29 2025-12-18 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
CA2315230C (en) 1998-01-09 2004-06-29 Arizona Board Of Regents, A Body Corporate, Acting On Behalf Of Arizona State University Anti-cryptococcal peptides
MXPA01011502A (es) 1999-05-14 2003-08-20 Boehringer Ingelheim Pharma Compuestos de tipo profarmaco anti-tumorigenos, activados por enzimas.
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
EP1537140B1 (en) * 2001-11-07 2013-01-02 Agensys, Inc. Nucleic acid and corresponding protein entitled 161p2f10b useful in treatment and detection of cancer
ES2544527T3 (es) 2002-07-31 2015-09-01 Seattle Genetics, Inc. Conjugados de fármacos y su uso para tratar el cáncer, una enfermedad autoinmune o una enfermedad infecciosa
EP3434275A1 (en) 2003-11-06 2019-01-30 Seattle Genetics, Inc. Assay for cancer cells based on the use of auristatin conjugates with antibodies
JP2008519863A (ja) 2004-11-12 2008-06-12 シアトル ジェネティクス インコーポレイティッド Ｎ末端にアミノ安息香酸単位を有するオーリスタチン
WO2007008848A2 (en) 2005-07-07 2007-01-18 Seattle Genetics, Inc. Monomethylvaline compounds having phenylalanine carboxy modifications at the c-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
AU2007308792B2 (en) 2006-10-27 2013-01-24 Genentech, Inc. Antibodies and immunoconjugates and uses therefor
EP2265283B1 (en) 2008-03-18 2014-09-03 Seattle Genetics, Inc. Auristatin drug linker conjugates
EP3501546A3 (de) * 2011-04-21 2019-09-18 Seattle Genetics, Inc. Cystein-wirkstoff konjugate und ihre verwendung

Also Published As

Publication number Publication date
US20130157960A1 (en) 2013-06-20
JP5791707B2 (ja) 2015-10-07
CN103200950B (zh) 2016-03-16
JP2013533228A (ja) 2013-08-22
WO2011154359A1 (de) 2011-12-15
CA2801971A1 (en) 2011-12-15
EP2579887A1 (de) 2013-04-17
ES2528956T3 (es) 2015-02-13
HK1184363A1 (en) 2014-01-24
US8722629B2 (en) 2014-05-13
CN103200950A (zh) 2013-07-10
EP2579887B1 (de) 2014-11-12

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