NO310976B1 - 5,11-dihydrobenzo[b,e][1,4]oksazepinderivater og farmasoytiske sammensetninger inneholdende de samme - Google Patents
5,11-dihydrobenzo[b,e][1,4]oksazepinderivater og farmasoytiske sammensetninger inneholdende de samme Download PDFInfo
- Publication number
- NO310976B1 NO310976B1 NO19984162A NO984162A NO310976B1 NO 310976 B1 NO310976 B1 NO 310976B1 NO 19984162 A NO19984162 A NO 19984162A NO 984162 A NO984162 A NO 984162A NO 310976 B1 NO310976 B1 NO 310976B1
- Authority
- NO
- Norway
- Prior art keywords
- oxazepine
- hydrogen atom
- mmol
- dihydro
- hydrates
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 19
- WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical class O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 150000004677 hydrates Chemical class 0.000 claims abstract description 20
- 210000001035 gastrointestinal tract Anatomy 0.000 claims abstract description 17
- CJKPKVLFYAXEBS-UHFFFAOYSA-N 2,3,6,7-tetrahydrooxazepine Chemical class C1CC=CCNO1 CJKPKVLFYAXEBS-UHFFFAOYSA-N 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- REUFESBNLHXVHN-HSZRJFAPSA-N 11-[[(2r)-1-[2-(4-methoxyphenyl)ethyl]pyrrolidin-2-yl]methyl]-6h-benzo[c][1,5]benzoxazepine Chemical group C1=CC(OC)=CC=C1CCN1[C@@H](CN2C3=CC=CC=C3OCC3=CC=CC=C32)CCC1 REUFESBNLHXVHN-HSZRJFAPSA-N 0.000 claims description 5
- 208000012661 Dyskinesia Diseases 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- UKPCNMUHCSROLE-HSZRJFAPSA-N 11-[[(2r)-1-[2-(4-fluorophenyl)ethyl]pyrrolidin-2-yl]methyl]-6h-benzo[c][1,5]benzoxazepine Chemical compound C1=CC(F)=CC=C1CCN1[C@@H](CN2C3=CC=CC=C3OCC3=CC=CC=C32)CCC1 UKPCNMUHCSROLE-HSZRJFAPSA-N 0.000 claims description 3
- 230000006806 disease prevention Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 52
- 230000000694 effects Effects 0.000 abstract description 17
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- 230000002411 adverse Effects 0.000 abstract 1
- 230000007659 motor function Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
- 239000000243 solution Substances 0.000 description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 46
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000011780 sodium chloride Substances 0.000 description 23
- 238000000921 elemental analysis Methods 0.000 description 22
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- -1 methoxy, ethoxy Chemical group 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
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- 239000012044 organic layer Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 14
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
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- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- SLGIBJWUMUWIFH-UHFFFAOYSA-N 6,11-dihydrobenzo[c][1,5]benzoxazepine Chemical compound C1OC2=CC=CC=C2NC2=CC=CC=C12 SLGIBJWUMUWIFH-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 5
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 208000028774 intestinal disease Diseases 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920000609 methyl cellulose Polymers 0.000 description 5
- 239000001923 methylcellulose Substances 0.000 description 5
- 235000010981 methylcellulose Nutrition 0.000 description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- 108090000312 Calcium Channels Proteins 0.000 description 4
- 102000003922 Calcium Channels Human genes 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
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- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 3
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- FZTPYHFHQJQQFN-PKTZIBPZSA-N (3s,5r)-5-(6h-benzo[c][1,5]benzoxazepin-11-ylmethyl)-1-[2-(4-methoxyphenyl)ethyl]pyrrolidin-3-ol Chemical compound C1=CC(OC)=CC=C1CCN1[C@@H](CN2C3=CC=CC=C3OCC3=CC=CC=C32)C[C@H](O)C1 FZTPYHFHQJQQFN-PKTZIBPZSA-N 0.000 description 2
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- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 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
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- 239000002253 acid Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229940125714 antidiarrheal agent Drugs 0.000 description 1
- 239000003793 antidiarrheal agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
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- 210000001367 artery Anatomy 0.000 description 1
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- 235000010233 benzoic acid Nutrition 0.000 description 1
- 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 1
- 239000008280 blood Substances 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
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- PMMYEEVYMWASQN-QWWZWVQMSA-N cis-4-hydroxy-D-proline Chemical compound O[C@H]1C[NH2+][C@@H](C([O-])=O)C1 PMMYEEVYMWASQN-QWWZWVQMSA-N 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 230000007012 clinical effect Effects 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000003871 intestinal function Effects 0.000 description 1
- 230000008991 intestinal motility Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 229940125722 laxative agent Drugs 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940039748 oxalate Drugs 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
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- 230000035945 sensitivity Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
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- NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8310496 | 1996-03-11 | ||
| PCT/JP1997/000754 WO1997033885A1 (fr) | 1996-03-11 | 1997-03-11 | DERIVES DE 5,11-DIHYDRODIBENZ[b,e] [1,4]OXAZEPINE, ET COMPOSITIONS MEDICAMENTEUSES LES COMPORTANT |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO984162D0 NO984162D0 (no) | 1998-09-10 |
| NO984162L NO984162L (no) | 1998-11-05 |
| NO310976B1 true NO310976B1 (no) | 2001-09-24 |
Family
ID=13792896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19984162A NO310976B1 (no) | 1996-03-11 | 1998-09-10 | 5,11-dihydrobenzo[b,e][1,4]oksazepinderivater og farmasoytiske sammensetninger inneholdende de samme |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6127361A (pt) |
| EP (1) | EP0889043B1 (pt) |
| JP (1) | JP3127469B2 (pt) |
| KR (1) | KR100344331B1 (pt) |
| CN (1) | CN1085209C (pt) |
| AT (1) | ATE204871T1 (pt) |
| AU (1) | AU704521B2 (pt) |
| BR (1) | BR9707962A (pt) |
| CA (1) | CA2261271C (pt) |
| DE (1) | DE69706406T2 (pt) |
| ES (1) | ES2159843T3 (pt) |
| NO (1) | NO310976B1 (pt) |
| PT (1) | PT889043E (pt) |
| TW (1) | TW479057B (pt) |
| WO (1) | WO1997033885A1 (pt) |
| ZA (1) | ZA972038B (pt) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2304262A1 (en) * | 1997-09-10 | 1999-03-18 | Ajinomoto Co., Inc. | 5,11-dihydrodibenzo[b,e][i,4]oxazepine derivatives and pharmaceutical composition containing the same |
| WO2000040570A1 (fr) * | 1999-01-08 | 2000-07-13 | Ajinomoto Co., Inc. | Derives d'oxazepine et medicaments contenant ces derives |
| EP1219611A4 (en) * | 1999-09-03 | 2003-03-19 | Ajinomoto Kk | NEW PROCESSES FOR THE PRODUCTION OF OXAZEPINE DERIVATIVES |
| WO2002048120A1 (fr) * | 2000-12-11 | 2002-06-20 | Ajinomoto Co.,Inc. | Nouveaux cristaux de derives d'oxazepine et procede de production de ces derniers |
| JPWO2002096891A1 (ja) * | 2001-05-30 | 2004-09-09 | 味の素株式会社 | ジヒドロジアリールオキサゼピン誘導体及び該誘導体を含有する医薬組成物 |
| JP2005343791A (ja) * | 2002-05-31 | 2005-12-15 | Ajinomoto Co Inc | 消化管疾患を治療するための医薬組成物 |
| JP2005343790A (ja) * | 2002-05-31 | 2005-12-15 | Ajinomoto Co Inc | カルシウムチャネル拮抗薬を含有する医薬組成物 |
| CN104016937B (zh) * | 2014-05-09 | 2016-12-07 | 中科院广州化学有限公司 | 一种n-芳基氧氮杂卓酮类化合物及其制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8912303D0 (en) * | 1989-05-27 | 1989-07-12 | Pfizer Ltd | Therapeutic agents |
| AU2669992A (en) * | 1991-11-05 | 1993-06-07 | G.D. Searle & Co. | 10-acyl-dibenz(b,f) (1,4)-oxazepines and their thiazepines analo gues useful as prostaglandin antagonists |
| CA2429769C (en) * | 2000-12-07 | 2016-04-26 | Board Of Regents, The University Of Texas System | Methods of treatment involving human mda-7 |
-
1997
- 1997-03-10 TW TW086102931A patent/TW479057B/zh not_active IP Right Cessation
- 1997-03-10 ZA ZA9702038A patent/ZA972038B/xx unknown
- 1997-03-11 PT PT97905478T patent/PT889043E/pt unknown
- 1997-03-11 US US09/147,012 patent/US6127361A/en not_active Expired - Fee Related
- 1997-03-11 KR KR1019980707117A patent/KR100344331B1/ko not_active IP Right Cessation
- 1997-03-11 DE DE69706406T patent/DE69706406T2/de not_active Expired - Fee Related
- 1997-03-11 EP EP97905478A patent/EP0889043B1/en not_active Expired - Lifetime
- 1997-03-11 WO PCT/JP1997/000754 patent/WO1997033885A1/ja active IP Right Grant
- 1997-03-11 CN CN97193005A patent/CN1085209C/zh not_active Expired - Fee Related
- 1997-03-11 JP JP09532434A patent/JP3127469B2/ja not_active Expired - Fee Related
- 1997-03-11 CA CA002261271A patent/CA2261271C/en not_active Expired - Fee Related
- 1997-03-11 BR BR9707962A patent/BR9707962A/pt not_active IP Right Cessation
- 1997-03-11 ES ES97905478T patent/ES2159843T3/es not_active Expired - Lifetime
- 1997-03-11 AT AT97905478T patent/ATE204871T1/de not_active IP Right Cessation
- 1997-03-11 AU AU22335/97A patent/AU704521B2/en not_active Ceased
-
1998
- 1998-09-10 NO NO19984162A patent/NO310976B1/no unknown
-
2000
- 2000-06-19 US US09/597,409 patent/US6436922B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE204871T1 (de) | 2001-09-15 |
| CA2261271C (en) | 2003-09-16 |
| ES2159843T3 (es) | 2001-10-16 |
| DE69706406D1 (de) | 2001-10-04 |
| TW479057B (en) | 2002-03-11 |
| PT889043E (pt) | 2002-02-28 |
| US6436922B1 (en) | 2002-08-20 |
| AU2233597A (en) | 1997-10-01 |
| BR9707962A (pt) | 1999-07-27 |
| KR100344331B1 (ko) | 2002-12-05 |
| CN1085209C (zh) | 2002-05-22 |
| JP3127469B2 (ja) | 2001-01-22 |
| NO984162L (no) | 1998-11-05 |
| AU704521B2 (en) | 1999-04-22 |
| CA2261271A1 (en) | 1997-09-18 |
| ZA972038B (en) | 1997-09-17 |
| CN1213371A (zh) | 1999-04-07 |
| DE69706406T2 (de) | 2002-04-18 |
| US6127361A (en) | 2000-10-03 |
| EP0889043A4 (en) | 1999-07-21 |
| EP0889043A1 (en) | 1999-01-07 |
| NO984162D0 (no) | 1998-09-10 |
| KR19990087655A (ko) | 1999-12-27 |
| EP0889043B1 (en) | 2001-08-29 |
| WO1997033885A1 (fr) | 1997-09-18 |
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