WO1999032509A3 - Hemiasterlin analogs - Google Patents

Hemiasterlin analogs Download PDF

Info

Publication number
WO1999032509A3
WO1999032509A3 PCT/CA1998/001184 CA9801184W WO9932509A3 WO 1999032509 A3 WO1999032509 A3 WO 1999032509A3 CA 9801184 W CA9801184 W CA 9801184W WO 9932509 A3 WO9932509 A3 WO 9932509A3
Authority
WO
WIPO (PCT)
Prior art keywords
analogs
hemiasterlin
hemiasterlin analogs
cytotoxic
synthesis
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.)
Ceased
Application number
PCT/CA1998/001184
Other languages
French (fr)
Other versions
WO1999032509A2 (en
Inventor
Raymond Andersen
Edward Piers
James Nieman
John Coleman
Michel Roberge
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.)
University of British Columbia
Original Assignee
University of British Columbia
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
Priority to US09/581,511 priority Critical patent/US7579323B1/en
Priority to IL13665498A priority patent/IL136654A0/en
Priority to HK01105313.8A priority patent/HK1034523B/en
Priority to DE69840415T priority patent/DE69840415D1/en
Priority to EP98962157A priority patent/EP1040119B1/en
Priority to BR9813817-0A priority patent/BR9813817A/en
Priority to CA2312826A priority patent/CA2312826C/en
Priority to AU17459/99A priority patent/AU762691C/en
Application filed by University of British Columbia filed Critical University of British Columbia
Priority to NZ505086A priority patent/NZ505086A/en
Priority to JP2000525446A priority patent/JP4417551B2/en
Priority to DK98962157T priority patent/DK1040119T3/en
Priority to KR1020007006814A priority patent/KR100937756B1/en
Publication of WO1999032509A2 publication Critical patent/WO1999032509A2/en
Publication of WO1999032509A3 publication Critical patent/WO1999032509A3/en
Anticipated expiration legal-status Critical
Priority to US12/491,839 priority patent/US20090264487A1/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Junction Field-Effect Transistors (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyrrole Compounds (AREA)
  • Amplifiers (AREA)
  • Steroid Compounds (AREA)

Abstract

This invention provides analogs of hemiasterlin, methods of synthesis of the analogs and use of the analogs as a cytotoxic and anti-mitotic agents.
PCT/CA1998/001184 1997-12-19 1998-12-18 Hemiasterlin analogs Ceased WO1999032509A2 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
US09/581,511 US7579323B1 (en) 1997-12-19 1998-12-13 Hemiasterlin analogs
NZ505086A NZ505086A (en) 1997-12-19 1998-12-18 Dipeptide and tripeptide hemiasterlin analogs
DE69840415T DE69840415D1 (en) 1997-12-19 1998-12-18 HAEMASTERLIN ANALOG
EP98962157A EP1040119B1 (en) 1997-12-19 1998-12-18 Hemiasterlin analogs
BR9813817-0A BR9813817A (en) 1997-12-19 1998-12-18 Hemiasterline analogs
CA2312826A CA2312826C (en) 1997-12-19 1998-12-18 Hemiasterlin analogs
AU17459/99A AU762691C (en) 1997-12-19 1998-12-18 Hemiasterlin analogs
IL13665498A IL136654A0 (en) 1997-12-19 1998-12-18 Hemiasterlin analogs
DK98962157T DK1040119T3 (en) 1997-12-19 1998-12-18 Hemiasterline analogues
HK01105313.8A HK1034523B (en) 1997-12-19 1998-12-18 Hemiasterlin analogs
JP2000525446A JP4417551B2 (en) 1997-12-19 1998-12-18 Hemia Stalin analog
KR1020007006814A KR100937756B1 (en) 1997-12-19 1998-12-18 Hemiasterin analogs
US12/491,839 US20090264487A1 (en) 1997-12-19 2009-06-25 Hemiasterlin analogs

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CA2,225,325 1997-12-19
CA002225325A CA2225325A1 (en) 1997-12-19 1997-12-19 Hemiasterlin analogs

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/491,839 Division US20090264487A1 (en) 1997-12-19 2009-06-25 Hemiasterlin analogs

Publications (2)

Publication Number Publication Date
WO1999032509A2 WO1999032509A2 (en) 1999-07-01
WO1999032509A3 true WO1999032509A3 (en) 1999-10-07

Family

ID=4161925

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA1998/001184 Ceased WO1999032509A2 (en) 1997-12-19 1998-12-18 Hemiasterlin analogs

Country Status (16)

Country Link
US (2) US7579323B1 (en)
EP (1) EP1040119B1 (en)
JP (1) JP4417551B2 (en)
KR (1) KR100937756B1 (en)
CN (1) CN100422208C (en)
AT (1) ATE419268T1 (en)
AU (1) AU762691C (en)
BR (1) BR9813817A (en)
CA (2) CA2225325A1 (en)
DE (1) DE69840415D1 (en)
DK (1) DK1040119T3 (en)
ES (1) ES2320499T3 (en)
HU (1) HUP0105460A3 (en)
IL (1) IL136654A0 (en)
NZ (1) NZ505086A (en)
WO (1) WO1999032509A2 (en)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1531846A4 (en) * 2002-02-27 2006-04-19 Us Gov Health & Human Serv LIGAND CONJUGATES, ADAPTER AND CYTOTOXIC AGENT, RELATED COMPOSITIONS AND RELATED METHODS OF USE
US7064211B2 (en) 2002-03-22 2006-06-20 Eisai Co., Ltd. Hemiasterlin derivatives and uses thereof
KR101208266B1 (en) * 2002-03-22 2012-12-05 에자이 알앤드디 매니지먼트 가부시키가이샤 Hemiasterlin derivatives and uses thereof
MXPA05002874A (en) 2002-09-20 2005-05-27 Wyeth Corp Process for the synthesis of intermediates useful for the synthesis of tubulin inhibitors.
WO2004026293A2 (en) * 2002-09-20 2004-04-01 Wyeth Holdings Corporation Hemiasterlin derivatives for treating resistant tumors
AU2003295808A1 (en) * 2002-11-21 2004-06-18 Wyeth Hemiasterlin affinity probes and their uses
US7390910B2 (en) * 2003-08-08 2008-06-24 Wyeth Compounds for treating tumors
GB201001070D0 (en) 2010-01-22 2010-03-10 St George's Hospital Medical School Theraputic compounds and their use
HK1220626A1 (en) 2013-03-15 2017-05-12 The Centre For Drug Research And Development Cytotoxic and anti-mitotic compounds, and methods of using the same
WO2015095953A1 (en) 2013-12-27 2015-07-02 The Centre For Drug Research And Development Sulfonamide-containing linkage systems for drug conjugates
BR112016015105A8 (en) * 2013-12-27 2018-04-24 Var2 Pharmaceuticals Aps var2csa-drug conjugates
ES2905569T3 (en) 2014-09-17 2022-04-11 Zymeworks Inc Cytotoxic and antimitotic compounds and methods of using them
PT3250237T (en) 2015-01-30 2021-06-30 Sutro Biopharma Inc Hemiasterlin derivatives for conjugation and therapy
US11021514B2 (en) 2016-06-01 2021-06-01 Athira Pharma, Inc. Compounds
US10517958B2 (en) 2016-10-04 2019-12-31 Zymeworks Inc. Compositions and methods for the treatment of platinum-drug resistant cancer
WO2018128745A1 (en) 2017-01-06 2018-07-12 The Board Of Trustees Of The Leland Stanford Junior University Ciliary neurotrophic factor receptor ligands and methods of using the same
EP4321523A3 (en) 2017-08-10 2024-04-24 Sumitomo Pharma Co., Ltd. Hemiasterlin derivatives and antibody-drug conjugates including same
PL3666787T3 (en) 2017-08-10 2024-04-29 Sumitomo Pharma Co., Ltd. Antibody-drug conjugates including hemiasterlin derivative
JP7432531B2 (en) 2019-02-13 2024-02-16 住友ファーマ株式会社 Hemiasterlin derivatives with cysteine residues
WO2020166592A1 (en) 2019-02-13 2020-08-20 大日本住友製薬株式会社 Hemiasterlin derivative and antibody-drug conjugate thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4048305A (en) * 1975-04-09 1977-09-13 Dr. L. Zambeletti S.P.A. Tripeptides, their esters and amides, and anti-ulcera activity thereof
EP0150227A1 (en) * 1983-12-23 1985-08-07 FUJIREBIO KABUSHIKI KAISHA also trading as FUJIREBIO INC. Dipeptide derivatives and their use in determining the activity of carboxypeptidase A
WO1996033211A1 (en) * 1995-04-20 1996-10-24 University Of British Columbia Biologically active peptides and compositions, their use
US5661175A (en) * 1995-06-20 1997-08-26 Kashman; Yoel Hemiasterlin and geodiamolide TA

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1209644B (en) * 1985-06-21 1989-08-30 Isf Spa PHARMACOLOGICALLY ACTIVE COMPOUNDS.
US4820691A (en) * 1987-06-24 1989-04-11 E. R. Squibb & Sons, Inc. Amino acid 1,2-diketo derivatives as renin inhibitors
CA2042027A1 (en) 1989-09-15 1991-03-16 Arthur E. Bogden Treatment of colon cancer
US5811515A (en) * 1995-06-12 1998-09-22 California Institute Of Technology Synthesis of conformationally restricted amino acids, peptides, and peptidomimetics by catalytic ring closing metathesis
US6034066A (en) * 1995-07-17 2000-03-07 Peptide Therapeutics Limited Cysteine protease inhibitors for use in treatment of IGE mediated allergic diseases
US6214799B1 (en) * 1996-05-14 2001-04-10 Agouron Pharmaceuticals, Inc. Antipicornaviral compounds and methods for their use and preparation
US6126939A (en) * 1996-09-03 2000-10-03 Yeda Research And Development Co. Ltd. Anti-inflammatory dipeptide and pharmaceutical composition thereof
US6331554B1 (en) * 1997-03-28 2001-12-18 Agouron Pharmaceuticals, Inc. Antipicornaviral compounds, compositions containing them, and methods for their use
US6194578B1 (en) 1998-11-20 2001-02-27 Pfizer Inc. Dipeptide derivatives

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4048305A (en) * 1975-04-09 1977-09-13 Dr. L. Zambeletti S.P.A. Tripeptides, their esters and amides, and anti-ulcera activity thereof
EP0150227A1 (en) * 1983-12-23 1985-08-07 FUJIREBIO KABUSHIKI KAISHA also trading as FUJIREBIO INC. Dipeptide derivatives and their use in determining the activity of carboxypeptidase A
WO1996033211A1 (en) * 1995-04-20 1996-10-24 University Of British Columbia Biologically active peptides and compositions, their use
US5661175A (en) * 1995-06-20 1997-08-26 Kashman; Yoel Hemiasterlin and geodiamolide TA

Also Published As

Publication number Publication date
CA2312826C (en) 2013-06-11
US20090264487A1 (en) 2009-10-22
AU1745999A (en) 1999-07-12
US7579323B1 (en) 2009-08-25
JP4417551B2 (en) 2010-02-17
ATE419268T1 (en) 2009-01-15
CA2225325A1 (en) 1999-06-19
CN100422208C (en) 2008-10-01
CN1282336A (en) 2001-01-31
HUP0105460A2 (en) 2002-06-29
HK1034523A1 (en) 2001-10-26
JP2001526294A (en) 2001-12-18
DE69840415D1 (en) 2009-02-12
EP1040119B1 (en) 2008-12-31
KR20010024783A (en) 2001-03-26
DK1040119T3 (en) 2009-04-14
AU762691C (en) 2004-07-08
BR9813817A (en) 2000-10-10
KR100937756B1 (en) 2010-01-20
ES2320499T3 (en) 2009-05-22
IL136654A0 (en) 2001-06-14
CA2312826A1 (en) 1999-07-01
EP1040119A2 (en) 2000-10-04
NZ505086A (en) 2003-05-30
HUP0105460A3 (en) 2002-08-28
AU762691B2 (en) 2003-07-03
WO1999032509A2 (en) 1999-07-01

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