CA2253913A1 - Sel de bismuth de sialyloligosaccharide et procede pour traiter et inhiber les ulceres gastriques et duodenaux avec cette substance - Google Patents
Sel de bismuth de sialyloligosaccharide et procede pour traiter et inhiber les ulceres gastriques et duodenaux avec cette substance Download PDFInfo
- Publication number
- CA2253913A1 CA2253913A1 CA002253913A CA2253913A CA2253913A1 CA 2253913 A1 CA2253913 A1 CA 2253913A1 CA 002253913 A CA002253913 A CA 002253913A CA 2253913 A CA2253913 A CA 2253913A CA 2253913 A1 CA2253913 A1 CA 2253913A1
- Authority
- CA
- Canada
- Prior art keywords
- oligosaccharide
- galactose
- group
- stomach
- bismuth salt
- 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.)
- Abandoned
Links
- 150000001621 bismuth Chemical class 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 33
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 12
- 230000002496 gastric effect Effects 0.000 title abstract description 19
- 208000007107 Stomach Ulcer Diseases 0.000 title abstract description 11
- 208000000718 duodenal ulcer Diseases 0.000 title abstract description 11
- 229920001542 oligosaccharide Polymers 0.000 claims abstract description 63
- 150000002482 oligosaccharides Chemical class 0.000 claims abstract description 51
- 229930182830 galactose Natural products 0.000 claims abstract description 35
- 125000005647 linker group Chemical group 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 239000001301 oxygen Substances 0.000 claims abstract description 15
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 35
- 210000002784 stomach Anatomy 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 22
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- 150000001875 compounds Chemical class 0.000 claims description 12
- 210000001198 duodenum Anatomy 0.000 claims description 12
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 9
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- 239000003242 anti bacterial agent Substances 0.000 claims description 6
- 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 claims description 6
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 5
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 claims description 5
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 claims description 5
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims description 5
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- WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 claims description 4
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 4
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 claims description 4
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- OVRNDRQMDRJTHS-CBQIKETKSA-N N-Acetyl-D-Galactosamine Chemical compound CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-CBQIKETKSA-N 0.000 claims description 4
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims description 4
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- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims description 4
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 claims description 4
- 208000035415 Reinfection Diseases 0.000 claims description 4
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 4
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- 108091003079 Bovine Serum Albumin Proteins 0.000 claims description 3
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- 102000008100 Human Serum Albumin Human genes 0.000 claims description 3
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- 229920000858 Cyclodextrin Polymers 0.000 claims description 2
- 229920002307 Dextran Polymers 0.000 claims description 2
- ZSZNTTHCWDYSDW-UHFFFAOYSA-N N=C=S.NCCC1=CC=CC=C1 Chemical group N=C=S.NCCC1=CC=CC=C1 ZSZNTTHCWDYSDW-UHFFFAOYSA-N 0.000 claims description 2
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- 229940098773 bovine serum albumin Drugs 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims description 2
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 claims description 2
- 239000002960 lipid emulsion Substances 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- 239000002502 liposome Substances 0.000 claims description 2
- 229920002401 polyacrylamide Polymers 0.000 claims description 2
- 229920000656 polylysine Polymers 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 2
- OXNGKCPRVRBHPO-XLMUYGLTSA-N alpha-L-Fucp-(1->2)-beta-D-Galp-(1->3)-[alpha-L-Fucp-(1->4)]-beta-D-GlcpNAc Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](CO)O[C@@H](O)[C@@H]2NC(C)=O)O[C@H]2[C@H]([C@H](O)[C@H](O)[C@H](C)O2)O)O[C@H](CO)[C@H](O)[C@@H]1O OXNGKCPRVRBHPO-XLMUYGLTSA-N 0.000 claims 2
- 125000002951 idosyl group Chemical class C1([C@@H](O)[C@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims 2
- -1 sialyl oligosaccharide Chemical class 0.000 description 30
- 230000027455 binding Effects 0.000 description 24
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- 230000005764 inhibitory process Effects 0.000 description 19
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- 239000000243 solution Substances 0.000 description 8
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- 229940060155 neuac Drugs 0.000 description 7
- 229910052797 bismuth Inorganic materials 0.000 description 6
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- SUWYPNNPLSRNPS-UHFFFAOYSA-N plaunotol Natural products CC(C)=CCCC(C)=CCCC(CO)=CCCC(C)=CCO SUWYPNNPLSRNPS-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- SPOAFZKFCYREMW-FWYLUGOYSA-N rioprostil Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCCO SPOAFZKFCYREMW-FWYLUGOYSA-N 0.000 description 1
- 229950004712 rioprostil Drugs 0.000 description 1
- NMAOJFAMEOVURT-RTKIROINSA-N rosaprostol Chemical compound CCCCCC[C@H]1CCC(O)[C@@H]1CCCCCCC(O)=O NMAOJFAMEOVURT-RTKIROINSA-N 0.000 description 1
- 229950003055 rosaprostol Drugs 0.000 description 1
- NVBZUCIQNYPGCI-CTYIDZIISA-N rotraxate Chemical compound C1C[C@@H](CN)CC[C@@H]1C(=O)C1=CC=C(CCC(O)=O)C=C1 NVBZUCIQNYPGCI-CTYIDZIISA-N 0.000 description 1
- 229950007757 rotraxate Drugs 0.000 description 1
- 229960003287 roxatidine acetate Drugs 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 230000009450 sialylation Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229950004782 sofalcone Drugs 0.000 description 1
- GFWRVVCDTLRWPK-KPKJPENVSA-N sofalcone Chemical compound C1=CC(OCC=C(C)C)=CC=C1\C=C\C(=O)C1=CC=C(OCC=C(C)C)C=C1OCC(O)=O GFWRVVCDTLRWPK-KPKJPENVSA-N 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- SETMGIIITGNLAS-UHFFFAOYSA-N spizofurone Chemical compound O=C1C2=CC(C(=O)C)=CC=C2OC21CC2 SETMGIIITGNLAS-UHFFFAOYSA-N 0.000 description 1
- 229950001870 spizofurone Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 201000000498 stomach carcinoma Diseases 0.000 description 1
- 229960004291 sucralfate Drugs 0.000 description 1
- MNQYNQBOVCBZIQ-JQOFMKNESA-A sucralfate Chemical compound O[Al](O)OS(=O)(=O)O[C@@H]1[C@@H](OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](COS(=O)(=O)O[Al](O)O)O[C@H]1O[C@@]1(COS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)O1 MNQYNQBOVCBZIQ-JQOFMKNESA-A 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229950006156 teprenone Drugs 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229950008298 trimoprostil Drugs 0.000 description 1
- 229950008599 tritiozine Drugs 0.000 description 1
- MVOUIYUWRXPNKD-UHFFFAOYSA-N tritiozine Chemical compound COC1=C(OC)C(OC)=CC(C(=S)N2CCOCC2)=C1 MVOUIYUWRXPNKD-UHFFFAOYSA-N 0.000 description 1
- 229960001341 troxipide Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229960003118 zolimidine Drugs 0.000 description 1
- VSLIUWLPFRVCDL-UHFFFAOYSA-N zolimidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN(C=CC=C2)C2=N1 VSLIUWLPFRVCDL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7135—Compounds containing heavy metals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/245—Bismuth; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Procédé pour traiter et/ou inhiber les ulcères gastriques et duodénaux, comprenant l'administration d'une composition pharmaceutique contenant un sel de bismuth d'un oligosaccharide défini par la formule (I): (NeuAc-$(a)(2-3)-pGal-.beta.(1)-(-X-)¿m?-(-Y-)¿n?-)¿p?-Z dans laquelle X = une laison chimique ou un groupe capable de lier la p galactose soit au groupe de liaison Y soit au support multivalent Z; dans laquelle l'oxygène glycosidique C¿1? de galactose peut être remplacé par N, S ou C; Y = un groupe de liaison; Z = un support multivalent; m = 0 ou 1; n = 0 ou 1; et p = un nombre entier de 2-1000. L'invention propose également un procédé pour traiter et/ou inhiber les ulcères gastriques et duodénaux par l'administration d'une composition pharmaceutique comprenant un sel de bismuth d'un oligosaccharide défini par la formule (III) (NeuAc-.alpha.(2-3)-pGal-.beta.(1)-A dans laquelle A = un groupe capable de se lier avec la p galactose et dans laquelle l'oxygène glycosidique C¿1? de galactose peut être remplacé par N, S ou C.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1676596P | 1996-05-03 | 1996-05-03 | |
| US60/016,765 | 1996-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2253913A1 true CA2253913A1 (fr) | 1997-11-13 |
Family
ID=21778853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002253913A Abandoned CA2253913A1 (fr) | 1996-05-03 | 1997-04-28 | Sel de bismuth de sialyloligosaccharide et procede pour traiter et inhiber les ulceres gastriques et duodenaux avec cette substance |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0918526A1 (fr) |
| JP (1) | JP2000509714A (fr) |
| KR (1) | KR20000010732A (fr) |
| AU (1) | AU710576B2 (fr) |
| CA (1) | CA2253913A1 (fr) |
| WO (1) | WO1997041875A1 (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI20011403L (fi) * | 2001-06-29 | 2002-12-30 | Carbion Oy | Menetelmä ja koostumukset vatsan sairauksien hoitoon |
| US20040176320A1 (en) * | 2001-06-29 | 2004-09-09 | Jari Natunen | Use of at least one glycoinhibitor substance |
| JP5014018B2 (ja) * | 2006-10-18 | 2012-08-29 | 旭化成ケミカルズ株式会社 | ピロリ菌の抑制剤または静菌剤 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4935406A (en) * | 1988-09-20 | 1990-06-19 | Marion Laboratories, Inc. | Use of bismuth (phosph/sulf)ated saccharides against Camplyobacter-associated gastrointestinal disorders |
| AU4993893A (en) * | 1992-07-31 | 1994-03-03 | Neose Pharmaceuticals, Inc. | Compositions for treating and inhibiting gastric and duodenal ulcers |
| MX9304638A (es) * | 1992-07-31 | 1994-05-31 | Neose Pharm Inc | Composicion para tratar e inhibir las ulceras gastricas y duodenales. |
| EP0749314A4 (fr) * | 1994-03-02 | 2002-09-18 | Neose Technologies Inc | Procede de traitement et d'inhibition des ulceres gastriques et duodenaux |
-
1997
- 1997-04-28 CA CA002253913A patent/CA2253913A1/fr not_active Abandoned
- 1997-04-28 JP JP9539929A patent/JP2000509714A/ja active Pending
- 1997-04-28 AU AU27326/97A patent/AU710576B2/en not_active Ceased
- 1997-04-28 KR KR1019980708842A patent/KR20000010732A/ko not_active Withdrawn
- 1997-04-28 EP EP97921225A patent/EP0918526A1/fr not_active Withdrawn
- 1997-04-28 WO PCT/US1997/006376 patent/WO1997041875A1/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO1997041875A1 (fr) | 1997-11-13 |
| AU710576B2 (en) | 1999-09-23 |
| EP0918526A1 (fr) | 1999-06-02 |
| KR20000010732A (ko) | 2000-02-25 |
| AU2732697A (en) | 1997-11-26 |
| JP2000509714A (ja) | 2000-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |