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.)
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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)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Immunology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Oncology (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 (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
JP5933562B2 (ja) 2010-09-29 2016-06-15 シアトル ジェネティックス, インコーポレイテッド N−カルボキシアルキル−アウリスタチンおよびその使用
BR112013027119A8 (pt) * 2011-04-21 2018-03-06 Seattle Genetics Inc novos conjugados ligante-droga (adcs) e uso dos mesmos
CN104185477B (zh) 2011-11-17 2017-05-24 辉瑞公司 细胞毒性肽及其抗体‑药物缀合物
WO2014093379A1 (en) 2012-12-10 2014-06-19 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
JP6636925B2 (ja) 2013-12-17 2020-01-29 ノバルティス アーゲー 細胞障害性ペプチドおよびその抱合体
WO2015095953A1 (en) 2013-12-27 2015-07-02 The Centre For Drug Research And Development Sulfonamide-containing linkage systems for drug conjugates
HUE047952T2 (hu) 2014-04-25 2020-05-28 Pf Medicament Ellenanyag-drog konjugátum és alkalmazása rák kezelésében történõ alkalmazásra
HRP20190888T8 (hr) 2014-04-25 2019-10-04 Pierre Fabre Médicament Konjugat antitijela za igf-1r i lijeka i njegova upotreba u liječenju karcinoma
CA2951368A1 (en) 2014-06-13 2015-12-17 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
CN118119409A (zh) 2021-09-03 2024-05-31 东丽株式会社 癌的治疗和/或预防用药物组合物

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
DK1545613T3 (da) 2002-07-31 2011-11-14 Seattle Genetics Inc Auristatinkonjugater og deres anvendelse til behandling af cancer, en autoimmun sygdom eller en infektiøs sygdom
EP2478912B1 (en) 2003-11-06 2016-08-31 Seattle Genetics, Inc. Auristatin conjugates with anti-HER2 or anti-CD22 antibodies and their use in therapy
US8288352B2 (en) 2004-11-12 2012-10-16 Seattle Genetics, Inc. Auristatins having an aminobenzoic acid unit at the N terminus
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
BRPI0717638A2 (pt) 2006-10-27 2013-11-12 Genentech Inc Anticorpors e imunoconjugados e usos para os mesmos
DK2265283T3 (da) 2008-03-18 2014-10-20 Seattle Genetics Inc Auristatin-lægemiddel-linker-konjugater
WO2011154359A1 (de) 2010-06-10 2011-12-15 Bayer Pharma Aktiengesellschaft Neue auristatin-derivate und ihre verwendung
JP5933562B2 (ja) * 2010-09-29 2016-06-15 シアトル ジェネティックス, インコーポレイテッド N−カルボキシアルキル−アウリスタチンおよびその使用
BR112013027119A8 (pt) 2011-04-21 2018-03-06 Seattle Genetics Inc novos conjugados ligante-droga (adcs) e uso dos mesmos

Also Published As

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

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