CA2135852C - 5-methyluridine process for large-scale preparation of 2',3'-didehydro-3'-deoxythymidine (d4t) - Google Patents

5-methyluridine process for large-scale preparation of 2',3'-didehydro-3'-deoxythymidine (d4t) Download PDF

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Publication number
CA2135852C
CA2135852C CA002135852A CA2135852A CA2135852C CA 2135852 C CA2135852 C CA 2135852C CA 002135852 A CA002135852 A CA 002135852A CA 2135852 A CA2135852 A CA 2135852A CA 2135852 C CA2135852 C CA 2135852C
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CA
Canada
Prior art keywords
solvate
compound
give
methyluridine
iii
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.)
Expired - Fee Related
Application number
CA002135852A
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English (en)
French (fr)
Other versions
CA2135852A1 (en
Inventor
Bang-Chi Chen
Derron R. Stark
Stephen R. Baker
Sandra L. Quinlan
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.)
Bristol Myers Squibb Co
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Bristol Myers Squibb Co
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 Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co
Publication of CA2135852A1 publication Critical patent/CA2135852A1/en
Application granted granted Critical
Publication of CA2135852C publication Critical patent/CA2135852C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Virology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA002135852A 1993-11-15 1994-11-15 5-methyluridine process for large-scale preparation of 2',3'-didehydro-3'-deoxythymidine (d4t) Expired - Fee Related CA2135852C (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US15277893A 1993-11-15 1993-11-15
US15305893A 1993-11-15 1993-11-15
US08/152,778 1993-11-15
US08/153,058 1993-11-15
US08/309,637 1994-09-23
US08/309,637 US5672698A (en) 1993-11-15 1994-09-23 Preparation of 2',3'-didehydro-3'-deoxythymidine from 5-methyluridine

Publications (2)

Publication Number Publication Date
CA2135852A1 CA2135852A1 (en) 1995-05-16
CA2135852C true CA2135852C (en) 2006-01-03

Family

ID=27387314

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002135852A Expired - Fee Related CA2135852C (en) 1993-11-15 1994-11-15 5-methyluridine process for large-scale preparation of 2',3'-didehydro-3'-deoxythymidine (d4t)

Country Status (17)

Country Link
US (1) US5672698A (OSRAM)
EP (1) EP0653436B1 (OSRAM)
JP (2) JP3653292B2 (OSRAM)
KR (1) KR100329525B1 (OSRAM)
CN (2) CN1040115C (OSRAM)
AT (1) ATE162530T1 (OSRAM)
AU (1) AU686672B2 (OSRAM)
CA (1) CA2135852C (OSRAM)
DE (1) DE69408099T2 (OSRAM)
DK (1) DK0653436T3 (OSRAM)
ES (1) ES2113626T3 (OSRAM)
FI (1) FI115971B (OSRAM)
GR (1) GR3026638T3 (OSRAM)
HU (2) HU222118B1 (OSRAM)
IL (1) IL111569A (OSRAM)
SG (1) SG63554A1 (OSRAM)
TW (1) TW291480B (OSRAM)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5608049A (en) * 1995-03-10 1997-03-04 Bristol-Myers Squibb Company Preparation of d4T from 5-methyluridine
US5608048A (en) * 1995-06-05 1997-03-04 Bristol-Myers Squibb Company d4 T polymorphic Form 1 process
US7034009B2 (en) * 1995-10-26 2006-04-25 Sirna Therapeutics, Inc. Enzymatic nucleic acid-mediated treatment of ocular diseases or conditions related to levels of vascular endothelial growth factor receptor (VEGF-R)
US6482805B2 (en) 1998-03-25 2002-11-19 Parker Hughes Institute AZT derivatives exhibiting spermicidal and anti-viral activity
US6191120B1 (en) 1998-03-25 2001-02-20 Wayne Hughes Institute Spermicidally active 5-halo-6-alkoxy-5,6-dihydro-2′,3′-dideoxy-uridines and their pharamaceutical compositions
US7144874B2 (en) * 2002-10-25 2006-12-05 Parker Hughes Institute Aryl phosphate derivatives of d4T having activity against resistant HIV strains
US20070015733A1 (en) * 1998-06-29 2007-01-18 Parker Hughes Institute Aryl Phosphate Derivatives of d4T having Activity Against Resistant HIV Strains
US6030957A (en) * 1998-06-29 2000-02-29 Wayne Hughes Institute Aryl phosphate derivatives of d4T having anti-HIV activity
CN1055293C (zh) * 1998-10-06 2000-08-09 中国人民解放军第二军医大学 一种β-胸苷的制备方法
AU2001285197A1 (en) * 2000-09-06 2002-03-22 Bristol-Myers Squibb Company Stavudine polymorphic form 1 process
US6825177B2 (en) * 2000-10-30 2004-11-30 Parker Hughes Institute Aryl phosphate derivatives of d4T with potent anti-viral activity
PT1334108E (pt) * 2000-11-13 2005-08-31 Parker Hughes Inst Derivados arilfosfato da d4t
US20050131224A1 (en) * 2003-12-15 2005-06-16 Cti Pet Systems, Inc. Method for preparing radiolabeled thymidine
US7160537B2 (en) * 2003-12-15 2007-01-09 Siemens Medical Solutions Usa, Inc. Method for preparing radiolabeled thymidine having low chromophoric byproducts
US20060046972A1 (en) * 2004-08-31 2006-03-02 Parker Hughes Institute Cytotoxic nucleoside analog compound 003 for treating cancer
CN102180925B (zh) * 2011-03-22 2013-05-08 苏州迪马生物科技发展有限公司 5-甲基尿苷合成工艺中乳化层的处理方法
CN104926902A (zh) * 2014-03-17 2015-09-23 张容霞 2`-取代-2,2`-脱水尿苷或2`-取代-2,2`-脱水胞苷化合物及其制备方法和用途
CN106967767B (zh) * 2017-04-25 2019-09-24 苏州笃美生物科技有限公司 一种β-胸苷的合成方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
YU110888A (en) * 1987-06-10 1989-08-31 Wellcome Found Process for obtaining timine derivatives
US4921950A (en) * 1988-06-09 1990-05-01 Burroughs Wellcome Co. Preparation of 3'azido-3-'-deoxythymidine
JP3128080B2 (ja) * 1991-10-02 2001-01-29 日本製紙株式会社 核酸化合物の新規な製造方法

Also Published As

Publication number Publication date
US5672698A (en) 1997-09-30
CN1193021A (zh) 1998-09-16
KR100329525B1 (ko) 2002-11-14
CN1112123A (zh) 1995-11-22
KR950014132A (ko) 1995-06-15
TW291480B (OSRAM) 1996-11-21
HUT69172A (en) 1995-08-28
JP3653292B2 (ja) 2005-05-25
SG63554A1 (en) 1999-03-30
JPH07206856A (ja) 1995-08-08
AU686672B2 (en) 1998-02-12
FI945323A0 (fi) 1994-11-11
GR3026638T3 (en) 1998-07-31
HU222118B1 (hu) 2003-04-28
HU0105348D0 (en) 2002-02-28
DE69408099T2 (de) 1998-09-03
JP2005139197A (ja) 2005-06-02
CN1040115C (zh) 1998-10-07
ATE162530T1 (de) 1998-02-15
FI115971B (fi) 2005-08-31
DK0653436T3 (da) 1998-09-14
AU7880494A (en) 1995-06-01
FI945323L (fi) 1995-05-16
ES2113626T3 (es) 1998-05-01
IL111569A (en) 2001-03-19
CN1055477C (zh) 2000-08-16
EP0653436A1 (en) 1995-05-17
IL111569A0 (en) 1995-01-24
HU222119B1 (hu) 2003-04-28
CA2135852A1 (en) 1995-05-16
EP0653436B1 (en) 1998-01-21
HU9403257D0 (en) 1995-01-30
DE69408099D1 (de) 1998-02-26

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