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 PDFInfo
- 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
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- group
- novel
- applications
- same
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 abstract 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 abstract 2
- DVFXLNFDWATPMW-IWOKLKJTSA-N tert-butyldiphenylsilyl Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C(C)(C)C)[C@@H](OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](CC(O2)N2C3=NC=NC(N)=C3N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)O)C1 DVFXLNFDWATPMW-IWOKLKJTSA-N 0.000 abstract 2
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical class NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- -1 R3 is group H Chemical group 0.000 abstract 1
- 239000002253 acid Chemical group 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical group 0.000 abstract 1
- 150000001412 amines Chemical group 0.000 abstract 1
- 230000002528 anti-freeze Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 230000002218 hypoglycaemic effect Effects 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
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)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Diabetes (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (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.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
| AU2003274202A AU2003274202A1 (en) | 2002-07-25 | 2003-07-23 | Novel difluorinated gem compounds, preparation methods thereof and applications of same |
| 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 |
| EP03758183A EP1525208A2 (fr) | 2002-07-25 | 2003-07-23 | Nouveaux composes gem difluores, leurs procedes de preparation et leurs applications |
| US10/522,365 US20060142206A1 (en) | 2002-07-25 | 2003-07-23 | Novel difluorinated gem compounds, preparation methods thereof and applications of same |
| 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 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)
| 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 |
| US9175044B2 (en) | 2010-12-22 | 2015-11-03 | Tfchem | Derivatives of glyco-CF2-serine and glyco-CF2-threonine |
| 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 |
| US10100088B2 (en) | 2014-03-17 | 2018-10-16 | Tfchem | Glycopeptide derivatives for the preservation and protection of biological materials and microorganisms |
Citations (4)
| 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 |
-
2002
- 2002-07-25 FR FR0209627A patent/FR2842810B1/fr not_active Expired - Fee Related
-
2003
- 2003-07-23 JP JP2004526949A patent/JP2006508048A/ja active Pending
- 2003-07-23 BR BR0312917-9A patent/BR0312917A/pt not_active IP Right Cessation
- 2003-07-23 WO PCT/FR2003/002330 patent/WO2004014928A2/fr active Application Filing
- 2003-07-23 US US10/522,365 patent/US20060142206A1/en not_active Abandoned
- 2003-07-23 CN CNA038177706A patent/CN1671723A/zh active Pending
- 2003-07-23 EP EP03758183A patent/EP1525208A2/fr not_active Withdrawn
- 2003-07-23 CA CA002492940A patent/CA2492940A1/fr not_active Abandoned
- 2003-07-23 AU AU2003274202A patent/AU2003274202A1/en not_active Abandoned
- 2003-07-23 RU RU2005105066/04A patent/RU2369612C2/ru not_active IP Right Cessation
-
2005
- 2005-01-24 TN TNP2005000017A patent/TNSN05017A1/fr unknown
Patent Citations (4)
| 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)
| 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 |
|---|---|
| TNSN05017A1 (fr) | 2007-05-14 |
| RU2369612C2 (ru) | 2009-10-10 |
| AU2003274202A1 (en) | 2004-02-25 |
| WO2004014928A2 (fr) | 2004-02-19 |
| CN1671723A (zh) | 2005-09-21 |
| FR2842810A1 (fr) | 2004-01-30 |
| CA2492940A1 (fr) | 2004-02-19 |
| AU2003274202A8 (en) | 2004-02-25 |
| US20060142206A1 (en) | 2006-06-29 |
| RU2005105066A (ru) | 2005-08-27 |
| EP1525208A2 (fr) | 2005-04-27 |
| JP2006508048A (ja) | 2006-03-09 |
| BR0312917A (pt) | 2005-07-05 |
| FR2842810B1 (fr) | 2006-01-27 |
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