NO323409B1 - Nye oligosakkarider, deres fremstilling, farmasoytiske preparater inneholdende oligosakkaridene samt deres anvendelse. - Google Patents
Nye oligosakkarider, deres fremstilling, farmasoytiske preparater inneholdende oligosakkaridene samt deres anvendelse. Download PDFInfo
- Publication number
- NO323409B1 NO323409B1 NO20021859A NO20021859A NO323409B1 NO 323409 B1 NO323409 B1 NO 323409B1 NO 20021859 A NO20021859 A NO 20021859A NO 20021859 A NO20021859 A NO 20021859A NO 323409 B1 NO323409 B1 NO 323409B1
- Authority
- NO
- Norway
- Prior art keywords
- oligosaccharides
- formula
- residue
- sodium
- hydrogen atom
- Prior art date
Links
- 150000002482 oligosaccharides Chemical class 0.000 title claims abstract description 81
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 80
- 238000002360 preparation method Methods 0.000 title claims description 19
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 239000000203 mixture Substances 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 45
- 239000011734 sodium Substances 0.000 claims description 33
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 30
- 229910052708 sodium Inorganic materials 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 14
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 12
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 12
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 9
- 239000011591 potassium Chemical group 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 8
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 claims description 7
- 239000000908 ammonium hydroxide Substances 0.000 claims description 7
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
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- 229910052700 potassium Inorganic materials 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 239000011575 calcium Chemical group 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
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- 229940079593 drug Drugs 0.000 claims description 4
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- 239000011777 magnesium Chemical group 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 17
- 229920000669 heparin Polymers 0.000 description 17
- 229960002897 heparin Drugs 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
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- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 4
- WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 108010022901 Heparin Lyase Proteins 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- 206010034576 Peripheral ischaemia Diseases 0.000 description 3
- 239000011543 agarose gel Substances 0.000 description 3
- 229960002246 beta-d-glucopyranose Drugs 0.000 description 3
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- 230000001105 regulatory effect Effects 0.000 description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 3
- 229920000936 Agarose Polymers 0.000 description 2
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- 241000283690 Bos taurus Species 0.000 description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 description 2
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- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 description 2
- 108090000913 Nitrate Reductases Proteins 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
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- VWWQXMAJTJZDQX-UYBVJOGSSA-N flavin adenine dinucleotide Chemical compound C1=NC2=C(N)N=CN=C2N1[C@@H]([C@H](O)[C@@H]1O)O[C@@H]1CO[P@](O)(=O)O[P@@](O)(=O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C2=NC(=O)NC(=O)C2=NC2=C1C=C(C)C(C)=C2 VWWQXMAJTJZDQX-UYBVJOGSSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
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- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- TVZISJTYELEYPI-UHFFFAOYSA-N hypodiphosphoric acid Chemical compound OP(O)(=O)P(O)(O)=O TVZISJTYELEYPI-UHFFFAOYSA-N 0.000 description 1
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- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical group CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- 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
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
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- Neurology (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9913182A FR2800074B1 (fr) | 1999-10-22 | 1999-10-22 | Nouveaux oligosaccharides, leur preparation et les compositions pharmaceutiques les contenant |
| PCT/FR2000/002897 WO2001029055A2 (fr) | 1999-10-22 | 2000-10-18 | Nouveaux oligosaccharides, leur preparation et les compositions pharmaceutiques les contenant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20021859D0 NO20021859D0 (no) | 2002-04-19 |
| NO20021859L NO20021859L (no) | 2002-06-13 |
| NO323409B1 true NO323409B1 (no) | 2007-04-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20021859A NO323409B1 (no) | 1999-10-22 | 2002-04-19 | Nye oligosakkarider, deres fremstilling, farmasoytiske preparater inneholdende oligosakkaridene samt deres anvendelse. |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP1226148B1 (cs) |
| JP (1) | JP4733329B2 (cs) |
| KR (2) | KR100778166B1 (cs) |
| CN (1) | CN1241932C (cs) |
| AT (1) | ATE534656T1 (cs) |
| AU (1) | AU781414B2 (cs) |
| BR (1) | BR0014939A (cs) |
| CA (1) | CA2388369C (cs) |
| CY (1) | CY1112274T1 (cs) |
| CZ (1) | CZ303255B6 (cs) |
| DK (1) | DK1226148T3 (cs) |
| EA (1) | EA004046B1 (cs) |
| EE (1) | EE05091B1 (cs) |
| ES (1) | ES2376409T3 (cs) |
| FR (1) | FR2800074B1 (cs) |
| HK (1) | HK1050535A1 (cs) |
| HR (1) | HRP20020330A2 (cs) |
| HU (1) | HU229385B1 (cs) |
| IL (2) | IL149154A0 (cs) |
| ME (1) | MEP9309A (cs) |
| MX (1) | MXPA02003945A (cs) |
| NO (1) | NO323409B1 (cs) |
| NZ (1) | NZ518539A (cs) |
| PL (1) | PL204623B1 (cs) |
| PT (1) | PT1226148E (cs) |
| RS (1) | RS50829B (cs) |
| SK (1) | SK287459B6 (cs) |
| TR (1) | TR200201102T2 (cs) |
| UA (1) | UA72545C2 (cs) |
| WO (1) | WO2001029055A2 (cs) |
| ZA (1) | ZA200203102B (cs) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4676048B2 (ja) * | 2000-07-10 | 2011-04-27 | 生化学工業株式会社 | 脱髄性疾患処置剤 |
| ES2238383T3 (es) * | 2000-12-16 | 2005-09-01 | Aventis Pharma Deutschland Gmbh | Uso de heparina de bajo peso molecular para el tratamiento de la osteoartrosis. |
| DE10121003A1 (de) | 2001-04-28 | 2002-12-19 | Aventis Pharma Gmbh | Anthranilsäureamide, Verfahren zur Herstellung, ihrer Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| EP2284535A1 (en) | 2002-03-11 | 2011-02-16 | Momenta Pharmaceuticals, Inc. | Low molecular weight heparins |
| FR2844808B1 (fr) * | 2002-09-23 | 2005-02-25 | Aventis Pharma Sa | Methode de determination de groupements specifiques constituant les heparines ou les heparines de bas poids moleculaire |
| US20040171819A1 (en) | 2002-10-10 | 2004-09-02 | Aventis Pharma S.A. | Mixtures of polysaccharides derived from heparin, their preparation and pharmaceutical compositions containing them |
| US7511026B2 (en) * | 2003-03-25 | 2009-03-31 | Seikagaku Corporation | Therapeutic agent for nerve damage |
| US7956046B2 (en) * | 2003-07-24 | 2011-06-07 | Aventis Pharma S.A. | Oligosaccharide mixtures derived from heparin, preparation thereof and pharmaceutical compositions containing them |
| FR2857971B1 (fr) * | 2003-07-24 | 2005-08-26 | Aventis Pharma Sa | Melanges d'oligosaccharides derives d'heparine, leur preparation et les compositions pharmaceutiques les contenant |
| US20050186679A1 (en) * | 2004-02-24 | 2005-08-25 | Christian Viskov | Method for determining specific groups constituting heparins or low molecular weight heparins |
| EP1580197A1 (en) * | 2004-03-24 | 2005-09-28 | Aventis Pharma S.A. | Method for quantitatively determining specific groups constituting heparins or low molecular wieght heparins using HPLC |
| EP1582531A1 (en) | 2004-03-24 | 2005-10-05 | Aventis Pharma S.A. | Process for oxidizing unfractionated heparins and detecting presence or absence of glycoserine in heparin and heparin products |
| DE102005017799A1 (de) * | 2005-04-18 | 2006-10-19 | Abbott Gmbh & Co. Kg | Verwendung von Heparin und Heparinderivaten zur Modulation des Neuritenwachstum-kontrollierenden Nogo-Rezeptors |
| US8101733B1 (en) | 2006-06-27 | 2012-01-24 | Momenta Pharmaceuticals, Inc. | Methods of evaluating mixtures of polysaccharides |
| US7790466B1 (en) | 2007-01-26 | 2010-09-07 | Momenta Pharmaceuticals, Inc. | Evaluating mixtures of low molecular weight heparins by chain profiles or chain mapping |
| US7968082B1 (en) | 2007-01-26 | 2011-06-28 | Momenta Pharmaceuticals, Inc. | Evaluating mixtures of low molecular weight heparins by NMR |
| US9139876B1 (en) | 2007-05-03 | 2015-09-22 | Momenta Pharmacueticals, Inc. | Method of analyzing a preparation of a low molecular weight heparin |
| EP2256138A1 (en) * | 2009-05-05 | 2010-12-01 | Sanofi-Aventis | Novel acylated 1,6-anhhydro decasaccharide and its use as antithrombotic agent |
| FR2949115B1 (fr) * | 2009-08-14 | 2012-11-02 | Sanofi Aventis | OLIGOSACCHARIDES N-SULFATES ACTIVATEURS DES RECEPTEURS DES FGFs, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
| FR2949114B1 (fr) * | 2009-08-14 | 2011-08-26 | Sanofi Aventis | OCTASACCHARIDES N-ACYLES ACTIVATEURS DES RECEPTEURS DES FGFs, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
| US8435795B2 (en) | 2010-01-19 | 2013-05-07 | Momenta Pharmaceuticals, Inc. | Evaluating heparin preparations |
| WO2012115952A1 (en) | 2011-02-21 | 2012-08-30 | Momenta Pharmaceuticals, Inc. | Evaluating heparin preparations |
| CN102864191A (zh) * | 2011-12-16 | 2013-01-09 | 深圳市海普瑞药业股份有限公司 | 肝素双糖混合物及其制备方法和应用 |
| CN104910217B (zh) * | 2015-06-19 | 2018-04-17 | 天津红日药业股份有限公司 | 用于磺达肝癸钠质量控制的参比化合物 |
| CZ308106B6 (cs) * | 2016-06-27 | 2020-01-08 | Contipro A.S. | Nenasycené deriváty polysacharidů, způsob jejich přípravy a jejich použití |
| CN110092848A (zh) * | 2019-05-14 | 2019-08-06 | 山东辰龙药业有限公司 | 一种贝米肝素钠的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2519987A1 (fr) * | 1982-01-15 | 1983-07-22 | Choay Sa | Trisaccharides a structures d-glucosamine, acide d-glucuronique, d-glucosamine et leur preparation |
| AU563351C (en) * | 1982-01-15 | 2003-06-19 | Glaxo Group Limited | Synthesis of oligosaccharides |
| FR2764511B1 (fr) * | 1997-06-13 | 2000-09-08 | Sanofi Sa | Compositions pour le traitement et la prevention de la thrombose arterielle et utilisation d'un inhibiteur du facteur xa seul et/ou en combinaison avec un antiagregant plaquettaire |
| JP4166851B2 (ja) * | 1997-09-29 | 2008-10-15 | 生化学工業株式会社 | 新規虚血・再灌流障害抑制剤 |
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1999
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2000
- 2000-10-18 CA CA2388369A patent/CA2388369C/fr not_active Expired - Fee Related
- 2000-10-18 NZ NZ518539A patent/NZ518539A/en not_active IP Right Cessation
- 2000-10-18 CZ CZ20021385A patent/CZ303255B6/cs not_active IP Right Cessation
- 2000-10-18 EA EA200200479A patent/EA004046B1/ru not_active IP Right Cessation
- 2000-10-18 DK DK00969634.5T patent/DK1226148T3/da active
- 2000-10-18 EP EP00969634A patent/EP1226148B1/fr not_active Expired - Lifetime
- 2000-10-18 BR BR0014939-0A patent/BR0014939A/pt active Pending
- 2000-10-18 AU AU79302/00A patent/AU781414B2/en not_active Ceased
- 2000-10-18 SK SK527-2002A patent/SK287459B6/sk not_active IP Right Cessation
- 2000-10-18 WO PCT/FR2000/002897 patent/WO2001029055A2/fr active IP Right Grant
- 2000-10-18 EE EEP200200208A patent/EE05091B1/xx not_active IP Right Cessation
- 2000-10-18 UA UA2002043067A patent/UA72545C2/uk unknown
- 2000-10-18 PL PL363052A patent/PL204623B1/pl not_active IP Right Cessation
- 2000-10-18 AT AT00969634T patent/ATE534656T1/de active
- 2000-10-18 MX MXPA02003945A patent/MXPA02003945A/es active IP Right Grant
- 2000-10-18 ES ES00969634T patent/ES2376409T3/es not_active Expired - Lifetime
- 2000-10-18 IL IL14915400A patent/IL149154A0/xx active IP Right Grant
- 2000-10-18 JP JP2001531853A patent/JP4733329B2/ja not_active Expired - Fee Related
- 2000-10-18 KR KR1020027005061A patent/KR100778166B1/ko not_active IP Right Cessation
- 2000-10-18 KR KR1020077018523A patent/KR100872215B1/ko not_active IP Right Cessation
- 2000-10-18 TR TR2002/01102T patent/TR200201102T2/xx unknown
- 2000-10-18 CN CNB008145318A patent/CN1241932C/zh not_active Expired - Fee Related
- 2000-10-18 ME MEP-93/09A patent/MEP9309A/xx unknown
- 2000-10-18 HU HU0203821A patent/HU229385B1/hu unknown
- 2000-10-18 PT PT00969634T patent/PT1226148E/pt unknown
- 2000-10-18 RS YUP-298/02A patent/RS50829B/sr unknown
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2002
- 2002-04-15 IL IL149154A patent/IL149154A/en not_active IP Right Cessation
- 2002-04-15 HR HR20020330A patent/HRP20020330A2/xx not_active IP Right Cessation
- 2002-04-18 ZA ZA200203102A patent/ZA200203102B/xx unknown
- 2002-04-19 NO NO20021859A patent/NO323409B1/no not_active IP Right Cessation
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2003
- 2003-04-16 HK HK03102754A patent/HK1050535A1/xx not_active IP Right Cessation
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2012
- 2012-02-01 CY CY20121100113T patent/CY1112274T1/el unknown
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