IL133598A - 4-Tricyclyl silyl alkoxy (alkylthio) phenolic as antioxidants - Google Patents
4-Tricyclyl silyl alkoxy (alkylthio) phenolic as antioxidantsInfo
- Publication number
- IL133598A IL133598A IL13359898A IL13359898A IL133598A IL 133598 A IL133598 A IL 133598A IL 13359898 A IL13359898 A IL 13359898A IL 13359898 A IL13359898 A IL 13359898A IL 133598 A IL133598 A IL 133598A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- phenol
- methyl
- pharmaceutical composition
- dimethylethyl
- Prior art date
Links
- 239000003963 antioxidant agent Substances 0.000 title claims description 12
- 150000002989 phenols Chemical class 0.000 title description 3
- 125000004414 alkyl thio group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 41
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 236
- -1 dimethyl-2-thienylsilyl Chemical group 0.000 claims description 68
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 58
- 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 claims description 45
- 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 claims description 45
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 40
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
- 108010064593 Intercellular Adhesion Molecule-1 Proteins 0.000 claims description 28
- 102000015271 Intercellular Adhesion Molecule-1 Human genes 0.000 claims description 28
- 230000014509 gene expression Effects 0.000 claims description 28
- 201000001320 Atherosclerosis Diseases 0.000 claims description 22
- 230000002401 inhibitory effect Effects 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 208000037976 chronic inflammation Diseases 0.000 claims description 13
- 102000004127 Cytokines Human genes 0.000 claims description 12
- 108090000695 Cytokines Proteins 0.000 claims description 12
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 9
- 230000000879 anti-atherosclerotic effect Effects 0.000 claims description 8
- 230000003078 antioxidant effect Effects 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 8
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 6
- 238000005502 peroxidation Methods 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- 206010052779 Transplant rejections Diseases 0.000 claims description 4
- 230000006020 chronic inflammation Effects 0.000 claims description 4
- 238000008214 LDL Cholesterol Methods 0.000 claims description 3
- 230000005747 tumor angiogenesis Effects 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- 210000002966 serum Anatomy 0.000 description 51
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 39
- 238000000034 method Methods 0.000 description 33
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 32
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 30
- 210000004185 liver Anatomy 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 21
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 21
- 238000003756 stirring Methods 0.000 description 20
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- 239000000524 Thiobarbituric Acid Reactive Substance Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000002835 absorbance Methods 0.000 description 12
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- 239000010410 layer Substances 0.000 description 12
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- 125000001424 substituent group Chemical group 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 239000002207 metabolite Substances 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- 229960005137 succinic acid Drugs 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- JVYPWWAPULSFQL-UHFFFAOYSA-N chloromethyl-(furan-2-yl)-dimethylsilane Chemical compound ClC[Si](C)(C)C1=CC=CO1 JVYPWWAPULSFQL-UHFFFAOYSA-N 0.000 description 10
- 150000001993 dienes Chemical class 0.000 description 10
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- 235000019260 propionic acid Nutrition 0.000 description 9
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- 208000029078 coronary artery disease Diseases 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
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- 230000005764 inhibitory process Effects 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 235000009518 sodium iodide Nutrition 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 6
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
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- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
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- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
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- 235000013874 shellac Nutrition 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- 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
-
- 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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Biochemistry (AREA)
- Cardiology (AREA)
- Toxicology (AREA)
- Transplantation (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88162797A | 1997-06-24 | 1997-06-24 | |
| PCT/US1998/010510 WO1998058938A1 (en) | 1997-06-24 | 1998-05-21 | Alkyl-4-silylheterocyclic phenols and thiophenols as antioxidant agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL133598A0 IL133598A0 (en) | 2001-04-30 |
| IL133598A true IL133598A (en) | 2004-08-31 |
Family
ID=25378856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL13359898A IL133598A (en) | 1997-06-24 | 1998-05-21 | 4-Tricyclyl silyl alkoxy (alkylthio) phenolic as antioxidants |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0998477B1 (de) |
| JP (1) | JP2002514226A (de) |
| KR (1) | KR20010014118A (de) |
| CN (1) | CN1147495C (de) |
| AR (1) | AR013114A1 (de) |
| AT (1) | ATE235498T1 (de) |
| AU (1) | AU731278B2 (de) |
| BR (1) | BR9810311A (de) |
| CA (1) | CA2293461C (de) |
| DE (1) | DE69812635T2 (de) |
| DK (1) | DK0998477T3 (de) |
| ES (1) | ES2190592T3 (de) |
| HU (1) | HUP0002775A3 (de) |
| IL (1) | IL133598A (de) |
| NO (1) | NO996395L (de) |
| NZ (1) | NZ501342A (de) |
| PT (1) | PT998477E (de) |
| SI (1) | SI0998477T1 (de) |
| TW (1) | TW517054B (de) |
| WO (1) | WO1998058938A1 (de) |
| ZA (1) | ZA985318B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007509054A (ja) * | 2003-10-17 | 2007-04-12 | アミリン・ファーマシューティカルズ，インコーポレイテッド | 血管健康を促進するシリルフェノール |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5155250A (en) * | 1990-07-05 | 1992-10-13 | Merrell Dow Pharmaceuticals Inc. | 2,6-di-alkyl-4-silyl-phenols as antiatheroscerotic agents |
| ES2233937T3 (es) * | 1993-12-10 | 2005-06-16 | Merrell Pharmaceuticals Inc. | Metodo para disminuir los niveles de colesterol serico con 2,6-dialquil-4-silil-fenoles. |
-
1998
- 1998-05-21 ES ES98923681T patent/ES2190592T3/es not_active Expired - Lifetime
- 1998-05-21 AU AU75915/98A patent/AU731278B2/en not_active Ceased
- 1998-05-21 CN CNB988065770A patent/CN1147495C/zh not_active Expired - Fee Related
- 1998-05-21 EP EP98923681A patent/EP0998477B1/de not_active Expired - Lifetime
- 1998-05-21 IL IL13359898A patent/IL133598A/en not_active IP Right Cessation
- 1998-05-21 AT AT98923681T patent/ATE235498T1/de not_active IP Right Cessation
- 1998-05-21 WO PCT/US1998/010510 patent/WO1998058938A1/en not_active Ceased
- 1998-05-21 KR KR19997012174A patent/KR20010014118A/ko not_active Abandoned
- 1998-05-21 DK DK98923681T patent/DK0998477T3/da active
- 1998-05-21 CA CA002293461A patent/CA2293461C/en not_active Expired - Fee Related
- 1998-05-21 DE DE69812635T patent/DE69812635T2/de not_active Expired - Fee Related
- 1998-05-21 NZ NZ501342A patent/NZ501342A/en unknown
- 1998-05-21 BR BR9810311-3A patent/BR9810311A/pt not_active IP Right Cessation
- 1998-05-21 SI SI9830429T patent/SI0998477T1/xx unknown
- 1998-05-21 JP JP50443199A patent/JP2002514226A/ja active Pending
- 1998-05-21 HU HU0002775A patent/HUP0002775A3/hu unknown
- 1998-05-21 PT PT98923681T patent/PT998477E/pt unknown
- 1998-06-18 ZA ZA985318A patent/ZA985318B/xx unknown
- 1998-06-19 TW TW087109867A patent/TW517054B/zh not_active IP Right Cessation
- 1998-06-22 AR ARP980102977A patent/AR013114A1/es not_active Application Discontinuation
-
1999
- 1999-12-22 NO NO996395A patent/NO996395L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU7591598A (en) | 1999-01-04 |
| TW517054B (en) | 2003-01-11 |
| BR9810311A (pt) | 2000-09-19 |
| HK1027815A1 (en) | 2001-01-23 |
| ZA985318B (en) | 1999-01-11 |
| AU731278B2 (en) | 2001-03-29 |
| CN1261367A (zh) | 2000-07-26 |
| NO996395D0 (no) | 1999-12-22 |
| HUP0002775A3 (en) | 2001-08-28 |
| DK0998477T3 (da) | 2003-07-21 |
| HUP0002775A2 (hu) | 2001-05-28 |
| AR013114A1 (es) | 2000-12-13 |
| PT998477E (pt) | 2003-07-31 |
| SI0998477T1 (en) | 2003-08-31 |
| KR20010014118A (ko) | 2001-02-26 |
| CA2293461C (en) | 2004-02-24 |
| NO996395L (no) | 2000-02-23 |
| ES2190592T3 (es) | 2003-08-01 |
| EP0998477B1 (de) | 2003-03-26 |
| IL133598A0 (en) | 2001-04-30 |
| CN1147495C (zh) | 2004-04-28 |
| WO1998058938A1 (en) | 1998-12-30 |
| NZ501342A (en) | 2001-10-26 |
| CA2293461A1 (en) | 1998-12-30 |
| JP2002514226A (ja) | 2002-05-14 |
| DE69812635D1 (de) | 2003-04-30 |
| DE69812635T2 (de) | 2003-10-23 |
| EP0998477A1 (de) | 2000-05-10 |
| ATE235498T1 (de) | 2003-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| MM9K | Patent not in force due to non-payment of renewal fees |