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)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (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 2010-06-10
EP10165550.4 2010-06-10
EP11158464.5 2011-03-16
EP11158464 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
US8987209B2 (en) 2010-09-29 2015-03-24 Seattle Genetics, Inc. N-carboxyalkyl-auristatin and the use thereof
ES2543888T3 (es) 2011-03-16 2015-08-25 Seattle Genetics, Inc. N-carboxialquil-auristatinas y su utilización
SG194567A1 (en) * 2011-04-21 2013-12-30 Seattle Genetics Inc Novel binder-drug conjugates (adcs) and their use
EP2780039B9 (en) 2011-11-17 2018-04-18 Pfizer Inc Cytotoxic peptides and antibody drug conjugates thereof
MX2014007121A (es) * 2011-12-14 2014-09-04 Seattle Genetics Inc Nuevos conjugados de principio activo-ligante (adc) y su uso.
US10226535B2 (en) 2012-12-10 2019-03-12 Mersana Therapeutics, Inc. Auristatin compounds and conjugates thereof
HK1220626A1 (zh) 2013-03-15 2017-05-12 The Centre For Drug Research And Development 具细胞毒性和抗有丝分裂的化合物以及其使用方法
FR3005051A1 (fr) * 2013-04-25 2014-10-31 Pf Medicament Derives de la dolastatine 10 et d'auristatines
MX2016008448A (es) 2013-12-27 2017-01-09 Zymeworks Inc Conjugados de var2csa-farmaco.
KR102384740B1 (ko) 2013-12-27 2022-04-07 자임워크스 인코포레이티드 약물 접합체를 위한 설폰아마이드-함유 연결 시스템
MX378281B (es) 2014-04-25 2025-03-10 Pf Medicament Conjugado farmaco-anticuerpo y su uso para el tratamiento contra el cancer.
MA39909B1 (fr) 2014-04-25 2019-05-31 Pf Medicament Conjugué anticorps de l'igf-1r-médicament et son utilisation pour le traitement du cancer
ES2905569T3 (es) * 2014-09-17 2022-04-11 Zymeworks Inc Compuestos citotóxicos y antimitóticos y métodos para utilizarlos
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
WO2022217022A1 (en) 2021-04-10 2022-10-13 Profoundbio Us Co. Folr1 binding agents, conjugates thereof and methods of using the same
CA3216459A1 (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
CA3230737A1 (en) 2021-09-03 2023-03-09 Toray Industries, Inc. Pharmaceutical composition for cancer treatment and/or prevention
AR133955A1 (es) 2023-09-26 2025-11-19 Profoundbio Us Co Agentes de unión a ptk7, conjugados de éstos y métodos de uso de los mismos
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
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
ATE284412T1 (de) * 1998-01-09 2004-12-15 Univ Arizona State Anti-kryptokokkus peptide
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
ES2369542T3 (es) 2002-07-31 2011-12-01 Seattle Genetics, Inc. Conjugados de auristatina y su uso para tratar cáncer, una enfermedad autoinmune o una enfermedad infecciosa.
ES2605443T3 (es) 2003-11-06 2017-03-14 Seattle Genetics, Inc. Conjugados de auristatina con anticuerpos anti-HER2 o anti-CD22 y su uso en terapia
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
ES2708763T3 (es) 2005-07-07 2019-04-11 Seattle Genetics Inc Compuestos de monometilvalina que tienen modificaciones de la cadena lateral de fenilalanina en el extremo C
WO2007008848A2 (en) 2005-07-07 2007-01-18 Seattle Genetics, Inc. Monomethylvaline compounds having phenylalanine carboxy modifications at the c-terminus
PT2845866T (pt) 2006-10-27 2017-08-09 Genentech Inc Anticorpos e imunoconjugados e utilizações dos mesmos
WO2009117531A1 (en) 2008-03-18 2009-09-24 Seattle Genetics, Inc. Auristatin drug linker conjugates
SG194567A1 (en) * 2011-04-21 2013-12-30 Seattle Genetics Inc Novel binder-drug conjugates (adcs) and their use

Also Published As

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

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