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
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
CA2829736A
Other languages
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

    • 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
    • A61K38/07—Tetrapeptides
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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
    • 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
    • A61K47/62—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 a protein, peptide or polyamino acid
    • A61K47/64—Drug-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
    • A61K47/6415—Toxins or lectins, e.g. clostridial toxins or Pseudomonas exotoxins

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Immunology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Hematology (AREA)
  • Oncology (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 2011-03-16
EP11158481.9 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 (enExample)
EP (1) EP2686336B1 (enExample)
JP (2) JP6023097B2 (enExample)
CN (1) CN103764667B (enExample)
CA (1) CA2829736C (enExample)
ES (1) ES2543888T3 (enExample)
WO (1) WO2012123423A1 (enExample)

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
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
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
WO2015095301A2 (en) 2013-12-17 2015-06-25 Irm Llc Cytotoxic peptides and conjugates thereof
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
US9884817B2 (en) 2014-06-13 2018-02-06 Novartis Ag Auristatin derivatives and conjugates thereof
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
CA3230737A1 (en) 2021-09-03 2023-03-09 Toray Industries, Inc. Pharmaceutical composition for cancer treatment and/or prevention

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

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