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WO2004014928A3 - Nouveaux composes gem difluores, leurs procedes de preparation et leurs applications - Google Patents

Nouveaux composes gem difluores, leurs procedes de preparation et leurs applications Download PDF

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Publication number
WO2004014928A3
WO2004014928A3 PCT/FR2003/002330 FR0302330W WO2004014928A3 WO 2004014928 A3 WO2004014928 A3 WO 2004014928A3 FR 0302330 W FR0302330 W FR 0302330W WO 2004014928 A3 WO2004014928 A3 WO 2004014928A3
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WO
WIPO (PCT)
Prior art keywords
alkyl
group
novel
applications
same
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/FR2003/002330
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English (en)
Other versions
WO2004014928A2 (fr
Inventor
Jean-Charles Quirion
Xavier Pannecoucke
Hooge Francois D
Stephane Marcotte
Castelot-Deliencourt-Godefroy
Philippe Jubault
Vanessa Gouge
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.)
Institut National des Sciences Appliquees de Rouen
Original Assignee
Institut National des Sciences Appliquees de Rouen
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 Institut National des Sciences Appliquees de Rouen filed Critical Institut National des Sciences Appliquees de Rouen
Priority to CA002492940A priority Critical patent/CA2492940A1/fr
Priority to BR0312917-9A priority patent/BR0312917A/pt
Priority to AU2003274202A priority patent/AU2003274202A1/en
Priority to US10/522,365 priority patent/US20060142206A1/en
Priority to EP03758183A priority patent/EP1525208A2/fr
Priority to JP2004526949A priority patent/JP2006508048A/ja
Publication of WO2004014928A2 publication Critical patent/WO2004014928A2/fr
Publication of WO2004014928A3 publication Critical patent/WO2004014928A3/fr
Priority to TNP2005000017A priority patent/TNSN05017A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/18—Acyclic radicals, substituted by carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • 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

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Virology (AREA)
  • Rheumatology (AREA)
  • Obesity (AREA)
  • Immunology (AREA)
  • Communicable Diseases (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Oncology (AREA)
  • Pain & Pain Management (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Cosmetics (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Le produit selon l'invention concerne un composé gem difluoré de formule (I) où Rl est un groupement comportant une chaîne alkyle substituée par au moins une fonction amine, amide ou acide, R2 est un atome d’hydrogène H ou une fonction alcool libre ou protégée, R3 est un groupement H, CH3, CH2OH, CH2-OGP où GP est un groupe protecteur tel qu'un groupe alkyle, benzyle (Bn), triméthylsilyle (TMS), tert-butyldiméthylsilyle (TBDMS), tert-butyldiphénylsilyle (TBDPS), acétate (Ac)..., Y, Y', Y' sont des groupes indépendants où Y, Y', Y' = H, OR, N3, NR'R', SR`... avec R = H, Bn, Ac, TMS, TBDMS, TBDPS,..., R', R' = H, alkyl, allyl, Bn, tosylate (Ts), C(=O)-alkyl, C(=O)-Bn,..., R'' = H, alkyl, Ac. Elle s'applique notamment à l'utilisation dudit composé pour la préparation de médicaments antitumoraux, antiviraux, hypoglycémiants, anti-inflammatoires et de composés pour l'immunologie, pour la cosmétologie, ou encore d'analogues glycopeptidiques de molécules antigel.
PCT/FR2003/002330 2002-07-25 2003-07-23 Nouveaux composes gem difluores, leurs procedes de preparation et leurs applications Ceased WO2004014928A2 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
CA002492940A CA2492940A1 (fr) 2002-07-25 2003-07-23 Nouveaux composes gem difluores, leurs procedes de preparation et leurs applications
BR0312917-9A BR0312917A (pt) 2002-07-25 2003-07-23 Novos compostos gem difluorados, seus processos de preparo e suas respectivas aplicações
AU2003274202A AU2003274202A1 (en) 2002-07-25 2003-07-23 Novel difluorinated gem compounds, preparation methods thereof and applications of same
US10/522,365 US20060142206A1 (en) 2002-07-25 2003-07-23 Novel difluorinated gem compounds, preparation methods thereof and applications of same
EP03758183A EP1525208A2 (fr) 2002-07-25 2003-07-23 Nouveaux composes gem difluores, leurs procedes de preparation et leurs applications
JP2004526949A JP2006508048A (ja) 2002-07-25 2003-07-23 新規な二フッ化ジェミナル化合物、その製造方法およびその用途
TNP2005000017A TNSN05017A1 (fr) 2002-07-25 2005-01-24 Nouveaux composes gem difluores, leurs procedes de preparation et leurs applications

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0209627A FR2842810B1 (fr) 2002-07-25 2002-07-25 Nouveaux composes gem difluores, leur procedes de preparation et leurs applications.
FR02/09627 2002-07-25

Publications (2)

Publication Number Publication Date
WO2004014928A2 WO2004014928A2 (fr) 2004-02-19
WO2004014928A3 true WO2004014928A3 (fr) 2004-04-01

Family

ID=30011584

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2003/002330 Ceased WO2004014928A2 (fr) 2002-07-25 2003-07-23 Nouveaux composes gem difluores, leurs procedes de preparation et leurs applications

Country Status (11)

Country Link
US (1) US20060142206A1 (fr)
EP (1) EP1525208A2 (fr)
JP (1) JP2006508048A (fr)
CN (1) CN1671723A (fr)
AU (1) AU2003274202A1 (fr)
BR (1) BR0312917A (fr)
CA (1) CA2492940A1 (fr)
FR (1) FR2842810B1 (fr)
RU (1) RU2369612C2 (fr)
TN (1) TNSN05017A1 (fr)
WO (1) WO2004014928A2 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2878851B1 (fr) * 2004-12-02 2007-02-09 Inst Nat Sciences Appliq Composes c-glycopeptides gem-difluores, leur preparation et leur utilisation en cryochirurgie et/ou cryopreservation
FR2900406B1 (fr) * 2006-04-27 2013-09-06 Inst Nat Sciences Appliq Mimes stables de sucres de type c-glycosides et c-glycoconjugues,leur procede de preparation et leurs applications notamment dans le domaine de la cosmetique et du medicament.
FR2900405B1 (fr) * 2006-04-27 2013-11-29 Inst Nat Sciences Appliq Nouveaux composes c-glycosides monofluores, leurs procedes de preparation et leurs applications
FR2900656A1 (fr) * 2006-05-03 2007-11-09 Inst Nat Sciences Appliq Composes c-glycopeptides gem-difluores, leur preparation et leur utilisation notamment pour la preservation de materiaux biologiques
CA2653153A1 (fr) * 2008-02-07 2009-08-07 University Of Ottawa Analogues de glycoproteine antigel et utilisations connexes
FR2929615B1 (fr) * 2008-04-02 2010-12-17 Tfchem Composes c-aryl glycosides pour le traitement du diabete et de l'obesite.
KR100931249B1 (ko) * 2008-06-05 2009-12-11 주식회사 알앤엘바이오 신규 디아릴 헵타노이드계 화합물 및 그 용도
WO2012016935A1 (fr) 2010-08-02 2012-02-09 Centrum Für Angewandte Nanotechnologie (Can) Gmbh Dérivés de sucres à sept atomes de carbone (c-7) et leur utilisation
RU2013133788A (ru) 2010-12-22 2015-01-27 Тфшем Производные глико-cf2-серина и глико-cf2-треонина
EP2742032B1 (fr) 2011-08-08 2015-05-06 Tfchem Dérivés de c-isopropylgalactoside gem-difluorés
CN103497223B (zh) * 2013-09-13 2015-08-05 中国人民解放军第二军医大学 一种北沙参中所含的糖苷类化合物及其制备方法和应用
WO2015140178A1 (fr) 2014-03-17 2015-09-24 Tfchem Dérivés de glycopeptides utilisés en vue de la conservation et de la protection de matières biologiques et de microorganismes

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0354323A2 (fr) * 1988-08-12 1990-02-14 American Cyanamid Company Phosphates antidiabétiques
WO1994003480A1 (fr) * 1992-07-31 1994-02-17 Pfizer Inc. Derives de l'acide peptidyl 4-amino-2,2-difluoro-3-oxo-1,6-hexane-dioïque utilises comme agents antiinflammatoires
WO1999024449A2 (fr) * 1997-11-08 1999-05-20 Glaxo Group Limited Composes chimiques
WO2001027099A2 (fr) * 1999-10-15 2001-04-19 Sucampo, A.G. Nouvelle composition et son procede de stabilisation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0354323A2 (fr) * 1988-08-12 1990-02-14 American Cyanamid Company Phosphates antidiabétiques
WO1994003480A1 (fr) * 1992-07-31 1994-02-17 Pfizer Inc. Derives de l'acide peptidyl 4-amino-2,2-difluoro-3-oxo-1,6-hexane-dioïque utilises comme agents antiinflammatoires
WO1999024449A2 (fr) * 1997-11-08 1999-05-20 Glaxo Group Limited Composes chimiques
WO2001027099A2 (fr) * 1999-10-15 2001-04-19 Sucampo, A.G. Nouvelle composition et son procede de stabilisation

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BERBER, HATICE ET AL: "Part 12: Mixed organofluorine - organosilicon chemistry. Reactions of difluoroenoxysilanes with glycosyl donors: synthesis of difluoro-C-glycosides and difluoro-C-disaccharides", CHEMISTRY--A EUROPEAN JOURNAL (2001), 7(4), 903-909, XP002237146 *
MARCOTTE, S. ET AL: "Synthesis of new.alpha.- and.beta.-gem-difluoromethylene C-glycosides i the galactose and glucose series", TETRAHEDRON LETTERS (2001), 42(34), 5879-5882, XP004295947 *

Also Published As

Publication number Publication date
FR2842810B1 (fr) 2006-01-27
RU2369612C2 (ru) 2009-10-10
EP1525208A2 (fr) 2005-04-27
CA2492940A1 (fr) 2004-02-19
JP2006508048A (ja) 2006-03-09
BR0312917A (pt) 2005-07-05
AU2003274202A8 (en) 2004-02-25
AU2003274202A1 (en) 2004-02-25
RU2005105066A (ru) 2005-08-27
TNSN05017A1 (fr) 2007-05-14
WO2004014928A2 (fr) 2004-02-19
FR2842810A1 (fr) 2004-01-30
US20060142206A1 (en) 2006-06-29
CN1671723A (zh) 2005-09-21

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