NO319037B1 - Syntetiske polysakkarider, fremgangsmater for a fremstille dem og farmasoytiske blandinger inneholdende nevnte polysakkarider - Google Patents
Syntetiske polysakkarider, fremgangsmater for a fremstille dem og farmasoytiske blandinger inneholdende nevnte polysakkarider Download PDFInfo
- Publication number
- NO319037B1 NO319037B1 NO19985831A NO985831A NO319037B1 NO 319037 B1 NO319037 B1 NO 319037B1 NO 19985831 A NO19985831 A NO 19985831A NO 985831 A NO985831 A NO 985831A NO 319037 B1 NO319037 B1 NO 319037B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- sulfo
- acid
- formula
- tri
- Prior art date
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- 150000004676 glycans Chemical class 0.000 title claims abstract description 32
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 32
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims description 50
- 230000008569 process Effects 0.000 title description 2
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 50
- 150000002016 disaccharides Chemical class 0.000 claims abstract description 43
- 150000002772 monosaccharides Chemical group 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 150000002402 hexoses Chemical class 0.000 claims abstract description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 89
- 238000002360 preparation method Methods 0.000 claims description 47
- 159000000000 sodium salts Chemical class 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 26
- 239000004480 active ingredient Substances 0.000 claims description 24
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 150000004044 tetrasaccharides Chemical class 0.000 claims description 22
- 239000000370 acceptor Substances 0.000 claims description 21
- 125000006239 protecting group Chemical group 0.000 claims description 21
- 150000001720 carbohydrates Chemical class 0.000 claims description 20
- 150000001768 cations Chemical class 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 239000000386 donor Substances 0.000 claims description 14
- 150000001450 anions Chemical class 0.000 claims description 13
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 13
- 239000011734 sodium Substances 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 12
- 150000002482 oligosaccharides Chemical class 0.000 claims description 11
- 239000003146 anticoagulant agent Substances 0.000 claims description 10
- AEMOLEFTQBMNLQ-HNFCZKTMSA-N L-idopyranuronic acid Chemical compound OC1O[C@@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-HNFCZKTMSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000002785 anti-thrombosis Effects 0.000 claims description 9
- 229940097043 glucuronic acid Drugs 0.000 claims description 9
- 229920001542 oligosaccharide Polymers 0.000 claims description 9
- 235000000346 sugar Nutrition 0.000 claims description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 8
- 238000010511 deprotection reaction Methods 0.000 claims description 8
- 239000008103 glucose Substances 0.000 claims description 8
- 239000000348 glycosyl donor Substances 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 239000000937 glycosyl acceptor Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000012467 final product Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000007170 pathology Effects 0.000 claims description 6
- 229940127219 anticoagulant drug Drugs 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 239000003102 growth factor Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 5
- 125000003158 alcohol group Chemical group 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 230000015271 coagulation Effects 0.000 claims description 4
- 238000005345 coagulation Methods 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 4
- 238000003379 elimination reaction Methods 0.000 claims description 4
- 125000000020 sulfo group Chemical class O=S(=O)([*])O[H] 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 102000003886 Glycoproteins Human genes 0.000 claims description 3
- 108090000288 Glycoproteins Proteins 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 230000019635 sulfation Effects 0.000 claims description 3
- 238000005670 sulfation reaction Methods 0.000 claims description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005552 B01AC04 - Clopidogrel Substances 0.000 claims description 2
- 239000005528 B01AC05 - Ticlopidine Substances 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 2
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 230000002776 aggregation Effects 0.000 claims description 2
- 238000004220 aggregation Methods 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 239000005557 antagonist Substances 0.000 claims description 2
- 230000001772 anti-angiogenic effect Effects 0.000 claims description 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 2
- 230000002001 anti-metastasis Effects 0.000 claims description 2
- 230000000840 anti-viral effect Effects 0.000 claims description 2
- 210000000601 blood cell Anatomy 0.000 claims description 2
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 claims description 2
- 229960003009 clopidogrel Drugs 0.000 claims description 2
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 claims description 2
- 229960002768 dipyridamole Drugs 0.000 claims description 2
- 230000000055 hyoplipidemic effect Effects 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 230000035407 negative regulation of cell proliferation Effects 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 claims description 2
- 229960005001 ticlopidine Drugs 0.000 claims description 2
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 claims 3
- UYUXSRADSPPKRZ-SKNVOMKLSA-N D-glucurono-6,3-lactone Chemical group O=C[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O UYUXSRADSPPKRZ-SKNVOMKLSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 230000017066 negative regulation of growth Effects 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 125000003132 pyranosyl group Chemical group 0.000 claims 1
- -1 sulpho group Chemical class 0.000 abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 129
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
- 239000000243 solution Substances 0.000 description 53
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- 238000004809 thin layer chromatography Methods 0.000 description 33
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000004440 column chromatography Methods 0.000 description 21
- 230000000694 effects Effects 0.000 description 21
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 17
- 229940035024 thioglycerol Drugs 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 12
- 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 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 11
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 108090000379 Fibroblast growth factor 2 Proteins 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 9
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 8
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- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Virology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9607457A FR2749849B1 (fr) | 1996-06-14 | 1996-06-14 | Polysaccharides synthetiques, procede pour leur preparation et compositions pharmaceutiques les contenant |
| PCT/FR1997/001048 WO1997047659A1 (fr) | 1996-06-14 | 1997-06-11 | Polysaccharides synthetiques, procede pour leur preparation et compositions pharmaceutiques les contenant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO985831D0 NO985831D0 (no) | 1998-12-11 |
| NO985831L NO985831L (no) | 1999-02-11 |
| NO319037B1 true NO319037B1 (no) | 2005-06-06 |
Family
ID=9493087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19985831A NO319037B1 (no) | 1996-06-14 | 1998-12-11 | Syntetiske polysakkarider, fremgangsmater for a fremstille dem og farmasoytiske blandinger inneholdende nevnte polysakkarider |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7919614B2 (de) |
| EP (1) | EP0904299B1 (de) |
| JP (1) | JP3501813B2 (de) |
| AT (1) | ATE204883T1 (de) |
| AU (1) | AU3266797A (de) |
| BR (1) | BR9709722B1 (de) |
| CA (1) | CA2258146C (de) |
| CY (1) | CY2281B1 (de) |
| DE (1) | DE69706418T2 (de) |
| DK (1) | DK0904299T3 (de) |
| ES (1) | ES2163171T3 (de) |
| FR (1) | FR2749849B1 (de) |
| NO (1) | NO319037B1 (de) |
| PT (1) | PT904299E (de) |
| WO (1) | WO1997047659A1 (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2751334B1 (fr) * | 1996-07-19 | 1998-10-16 | Sanofi Sa | Polysaccharides synthetiques, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR2773804B1 (fr) * | 1998-01-19 | 2000-02-18 | Sanofi Sa | Polysaccharides de synthese, procede pour leur preparation et compositions pharmaceutiques le contenant |
| EP1574516A1 (de) * | 2004-03-05 | 2005-09-14 | Sanofi-Aventis | Antithrombotische Verbindungen |
| JP4796758B2 (ja) * | 2004-08-24 | 2011-10-19 | 学校法人 京都産業大学 | 組成物及びそれを含有する抗腫瘍剤 |
| TWI403334B (zh) | 2004-12-23 | 2013-08-01 | Merck Sharp & Dohme | 包含生物素殘基之抗血栓雙重抑制劑 |
| KR101529061B1 (ko) | 2008-05-30 | 2015-06-16 | 모멘타 파머슈티컬스 인코포레이티드 | 당류 구조물, 그리고 이러한 구조물의 제조 및 사용 방법 |
| 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 |
| 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 |
| FR2970969B1 (fr) * | 2011-01-27 | 2013-10-18 | Sanofi Aventis | Oligosaccharides 3-o-alkyles activateurs des recepteurs des fgfs, leur preparation et leur application en therapeutique |
| EP2578594A1 (de) * | 2011-10-04 | 2013-04-10 | Sanofi | Verfahren zur Herstellung von L-Iduronsäure mittels einer Decarboxylierung/intramolekulare Zyklisierungs-Tandemreaktion |
| WO2021211441A1 (en) * | 2020-04-13 | 2021-10-21 | The Board Of Regents Of The University Of Oklahoma | Modified sugar polymers with low anticoagulant activity and therapeutic activity |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5529985A (en) * | 1990-04-23 | 1996-06-25 | Akzo Nobel Nv | Sulfated glycosaminoglycanoid derivatives of the dermatan sulfate and chondroitin sulfate type |
| US5382570A (en) * | 1990-04-23 | 1995-01-17 | Akzo, N.V. | Sulfated glycosaminoglycanoid derivatives of the dermatan sulfate and chondroitin sulfate type |
| US5378829A (en) * | 1990-04-23 | 1995-01-03 | Akzo N.V. | Sulfated glycosaminoglycanoid derivatives of the heparin and heparan sulfate type |
| US5668274A (en) * | 1991-04-23 | 1997-09-16 | Akzo Nobel N.V. | Sulfated glycosaminoglycanoid derivatives of the dermatan sulfate and chondroitin sulfate type |
-
1996
- 1996-06-14 FR FR9607457A patent/FR2749849B1/fr not_active Expired - Fee Related
-
1997
- 1997-06-11 DK DK97928337T patent/DK0904299T3/da active
- 1997-06-11 AT AT97928337T patent/ATE204883T1/de active
- 1997-06-11 BR BRPI9709722-5A patent/BR9709722B1/pt not_active IP Right Cessation
- 1997-06-11 WO PCT/FR1997/001048 patent/WO1997047659A1/fr active IP Right Grant
- 1997-06-11 PT PT97928337T patent/PT904299E/pt unknown
- 1997-06-11 ES ES97928337T patent/ES2163171T3/es not_active Expired - Lifetime
- 1997-06-11 EP EP97928337A patent/EP0904299B1/de not_active Expired - Lifetime
- 1997-06-11 CA CA002258146A patent/CA2258146C/fr not_active Expired - Lifetime
- 1997-06-11 DE DE69706418T patent/DE69706418T2/de not_active Expired - Lifetime
- 1997-06-11 JP JP50130798A patent/JP3501813B2/ja not_active Expired - Lifetime
- 1997-06-11 AU AU32667/97A patent/AU3266797A/en not_active Abandoned
-
1998
- 1998-12-11 NO NO19985831A patent/NO319037B1/no not_active IP Right Cessation
-
2002
- 2002-05-15 CY CY0200035A patent/CY2281B1/xx unknown
-
2003
- 2003-10-02 US US10/677,894 patent/US7919614B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR9709722A (pt) | 2000-01-25 |
| DK0904299T3 (da) | 2001-12-17 |
| ES2163171T3 (es) | 2002-01-16 |
| NO985831L (no) | 1999-02-11 |
| FR2749849A1 (fr) | 1997-12-19 |
| AU3266797A (en) | 1998-01-07 |
| CY2281B1 (en) | 2003-07-04 |
| DE69706418T2 (de) | 2002-05-29 |
| JPH11513061A (ja) | 1999-11-09 |
| EP0904299B1 (de) | 2001-08-29 |
| DE69706418D1 (de) | 2001-10-04 |
| EP0904299A1 (de) | 1999-03-31 |
| NO985831D0 (no) | 1998-12-11 |
| US7919614B2 (en) | 2011-04-05 |
| PT904299E (pt) | 2002-02-28 |
| US20040068108A1 (en) | 2004-04-08 |
| ATE204883T1 (de) | 2001-09-15 |
| JP3501813B2 (ja) | 2004-03-02 |
| BR9709722B1 (pt) | 2010-12-14 |
| WO1997047659A1 (fr) | 1997-12-18 |
| CA2258146C (fr) | 2003-10-07 |
| CA2258146A1 (fr) | 1997-12-18 |
| FR2749849B1 (fr) | 1998-09-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |