CN101080251B - 制备莰佛胺及其盐的方法和中间体、含中间体的药物组合物，及其作为抗癌药的应用 - Google Patents

制备莰佛胺及其盐的方法和中间体、含中间体的药物组合物，及其作为抗癌药的应用 Download PDF

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Publication number
CN101080251B
CN101080251B CN2005800428600A CN200580042860A CN101080251B CN 101080251 B CN101080251 B CN 101080251B CN 2005800428600 A CN2005800428600 A CN 2005800428600A CN 200580042860 A CN200580042860 A CN 200580042860A CN 101080251 B CN101080251 B CN 101080251B
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China
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compound
acid
benzyloxycarbonyl
protecting group
canfosfamide
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Expired - Fee Related
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Chinese (zh)
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CN101080251A (zh
Inventor
威廉·A·布朗热
史蒂文·J·科利尔
斯蒂芬·A·伊斯特汉
丹尼斯·L·伊迪
罗南·Y·盖韦尔
佩德里·E·埃尔南德斯阿瓦德
詹森·R·海若
汉斯·J·谢尔斯高
哈罗德·梅克勒
罗伯特·E·波沃姆斯基
史蒂文·R·修
帕维尔·E·日奇金
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Telik Inc
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Telik Inc
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    • 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

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  • 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)
CN2005800428600A 2004-12-21 2005-11-23 制备莰佛胺及其盐的方法和中间体、含中间体的药物组合物，及其作为抗癌药的应用 Expired - Fee Related CN101080251B (zh)

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
CN101080251A CN101080251A (zh) 2007-11-28
CN101080251B true CN101080251B (zh) 2012-08-29

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CN2005800428600A Expired - Fee Related CN101080251B (zh) 2004-12-21 2005-11-23 制备莰佛胺及其盐的方法和中间体、含中间体的药物组合物，及其作为抗癌药的应用

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

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6506739B1 (en) * 2001-05-01 2003-01-14 Telik, Inc. Bis-(N,N'-bis-(2-haloethyl)amino)phosphoramidates as antitumor agents

Family Cites Families (5)

* 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
CN101090977B (zh) * 2005-01-06 2013-04-10 泰立克公司 三肽和四肽硫醚

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6506739B1 (en) * 2001-05-01 2003-01-14 Telik, Inc. Bis-(N,N'-bis-(2-haloethyl)amino)phosphoramidates as antitumor agents

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
Danyelle M.Townsend et al.efficacy of a glutathione s-transferase п-activated prodrug in platinum-resistant ovarian cancer cells.《molecular cancer therapeutics》.2002,第1卷第1089页右栏倒数第1段至第1090页左栏第1段和图1. *
J.A.Mclntyre et al.canfosfamide hydrochloride oncolytic DNA alkylating drug.《drugs of the future》.2004,第29卷(第10期),第986页方案1. *
Jan-Olov HooG et al.glutathione derivatives as inhibitors of glutaredoxin and ribonucleotide reductase from ESCHERICHIA COLI.《febs letters》.1982,第138卷(第1期),第59-61页. *
ke-wu yang et al.explaining the inhibition of glyoxalase II by 9-fluorenylmethoxycarbonyl-protected glutathione derivatives.《archives of biochemistry and biophysics》.2003,第414卷第271-278页. *
Matthew H.lyttle et al.glutathione-s-transferase activates novel alkylating agents.《journal of medicinal chemistry》.1994,第37卷(第10期),第1501-1507页. *
Paul j.ciaccio et al.modulation of detoxification gene expression in human colon HT29 cells by glutathione-s-transferase inhibitors.《molecular pharmacology》.1995,第48卷(第4期),第639-647页. *

Also Published As

Publication number Publication date
WO2006068769A1 (en) 2006-06-29
AU2005319579B2 (en) 2011-07-21
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
EA200701180A1 (ru) 2008-04-28

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