AU2005319579B2 - Process for and intermediates in the preparation of canfosfamide and its salts, pharmaceutical compositions containing some intermediates, and their use as anticancer agents - Google Patents

Process for and intermediates in the preparation of canfosfamide and its salts, pharmaceutical compositions containing some intermediates, and their use as anticancer agents Download PDF

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Publication number
AU2005319579B2
AU2005319579B2 AU2005319579A AU2005319579A AU2005319579B2 AU 2005319579 B2 AU2005319579 B2 AU 2005319579B2 AU 2005319579 A AU2005319579 A AU 2005319579A AU 2005319579 A AU2005319579 A AU 2005319579A AU 2005319579 B2 AU2005319579 B2 AU 2005319579B2
Authority
AU
Australia
Prior art keywords
compound
compounds
canfosfamide
benzyloxycarbonyl
protecting group
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
AU2005319579A
Other languages
English (en)
Other versions
AU2005319579A1 (en
Inventor
William A. Boulanger
Steven J. Collier
Stephen A. Eastham
Dennis L. Edie
Ronan Y. Guevel
Pedro E. Hernandez Abad
Jason R. Herr
Hans J. Kjaersgaard
Harold Meckler
Robert E. Polomski
Steven R. Schow
Pavel E. Zhichkin
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.)
Telik Inc
Original Assignee
Telik 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 Telik Inc filed Critical Telik Inc
Publication of AU2005319579A1 publication Critical patent/AU2005319579A1/en
Application granted granted Critical
Publication of AU2005319579B2 publication Critical patent/AU2005319579B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/36—Amides thereof
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/26—Amides of acids of phosphorus containing P-halide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/44—Amides thereof
    • 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
    • C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
    • 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
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
    • 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
    • C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
AU2005319579A 2004-12-21 2005-11-23 Process for and intermediates in the preparation of canfosfamide and its salts, pharmaceutical compositions containing some intermediates, and their use as anticancer agents Ceased AU2005319579B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11/018,391 US8198247B2 (en) 2004-12-21 2004-12-21 Process for and intermediates in the preparation of canfosfamide and its salts
US11/018,391 2004-12-21
PCT/US2005/042693 WO2006068769A1 (en) 2004-12-21 2005-11-23 Process for and intermediates in the preparation of canfosfamide and its salts, pharmaceutical compositions containing some intermediates, and their use as anticancer agents

Publications (2)

Publication Number Publication Date
AU2005319579A1 AU2005319579A1 (en) 2006-06-29
AU2005319579B2 true AU2005319579B2 (en) 2011-07-21

Family

ID=36216909

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2005319579A Ceased AU2005319579B2 (en) 2004-12-21 2005-11-23 Process for and intermediates in the preparation of canfosfamide and its salts, pharmaceutical compositions containing some intermediates, and their use as anticancer agents

Country Status (15)

Country Link
US (2) US8198247B2 (enExample)
EP (1) EP1827605B1 (enExample)
JP (1) JP5060306B2 (enExample)
KR (1) KR20070089795A (enExample)
CN (1) CN101080251B (enExample)
AR (1) AR052167A1 (enExample)
AU (1) AU2005319579B2 (enExample)
BR (1) BRPI0519141A2 (enExample)
CA (1) CA2587088A1 (enExample)
EA (1) EA016052B1 (enExample)
IL (1) IL182835A0 (enExample)
MX (1) MX2007007215A (enExample)
TW (1) TW200633717A (enExample)
WO (1) WO2006068769A1 (enExample)
ZA (1) ZA200704318B (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100056825A1 (en) * 2008-08-28 2010-03-04 Telik, Inc. Formulations of canfosfamide and their preparation
US8324426B2 (en) 2008-08-28 2012-12-04 Telik, Inc. Formulations of canfosfamide and their preparation
CA2733732A1 (en) * 2011-02-25 2012-08-25 Telik, Inc. Formulations of canfosfamide and their preparation

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5556942A (en) * 1991-04-29 1996-09-17 Terrapin Technologies, Inc. Glutathione S-transferase-activated compounds
US6627732B1 (en) * 1998-04-16 2003-09-30 Teijin Limited Glutathione derivatives and their dosage forms
US6417397B1 (en) * 1999-10-04 2002-07-09 The Regents Of The University Of California, San Diego N-substituted alkylamino acids for use as amino-protecting groups
UA74574C2 (en) 2000-05-02 2006-01-16 Telik Inc Bis (n,n'-bis(2-halogenethyl)amino)phosphodiamates, a method for producing thereof (variants), a pharmaceutical composition containing them, and a method for the treatment of tumors
US6506739B1 (en) * 2001-05-01 2003-01-14 Telik, Inc. Bis-(N,N'-bis-(2-haloethyl)amino)phosphoramidates as antitumor agents
CN101090977B (zh) * 2005-01-06 2013-04-10 泰立克公司 三肽和四肽硫醚

Also Published As

Publication number Publication date
WO2006068769A1 (en) 2006-06-29
CN101080251A (zh) 2007-11-28
JP2008524327A (ja) 2008-07-10
US8334266B2 (en) 2012-12-18
BRPI0519141A2 (pt) 2008-12-30
KR20070089795A (ko) 2007-09-03
IL182835A0 (en) 2007-08-19
TW200633717A (en) 2006-10-01
JP5060306B2 (ja) 2012-10-31
AR052167A1 (es) 2007-03-07
EP1827605A1 (en) 2007-09-05
MX2007007215A (es) 2007-08-14
EP1827605B1 (en) 2014-03-26
US20120238772A1 (en) 2012-09-20
CA2587088A1 (en) 2006-06-29
AU2005319579A1 (en) 2006-06-29
US20060135409A1 (en) 2006-06-22
ZA200704318B (en) 2008-09-25
US8198247B2 (en) 2012-06-12
EA016052B1 (ru) 2012-01-30
CN101080251B (zh) 2012-08-29
EA200701180A1 (ru) 2008-04-28

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Legal Events

Date Code Title Description
FGA Letters patent sealed or granted (standard patent)
MK14 Patent ceased section 143(a) (annual fees not paid) or expired