NO315236B1 - Tetrahydro gamma-karboliner, deres fremstilling og farmasöytiske sammensetninger inneholdende det samme - Google Patents
Tetrahydro gamma-karboliner, deres fremstilling og farmasöytiske sammensetninger inneholdende det samme Download PDFInfo
- Publication number
- NO315236B1 NO315236B1 NO20000737A NO20000737A NO315236B1 NO 315236 B1 NO315236 B1 NO 315236B1 NO 20000737 A NO20000737 A NO 20000737A NO 20000737 A NO20000737 A NO 20000737A NO 315236 B1 NO315236 B1 NO 315236B1
- Authority
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- Norway
- Prior art keywords
- formula
- alkyl
- radical
- hydrogen
- 6alkyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 title description 5
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- 239000000203 mixture Substances 0.000 claims abstract description 47
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 30
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 28
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- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
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- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 3
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- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 229960001186 methysergide Drugs 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- IRBXWOSHUFMZCL-UHFFFAOYSA-N n-[3-(5-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-2-yl)propyl]-1h-benzimidazol-2-amine;dihydrochloride Chemical compound Cl.Cl.C12=CC=CC=C2N(C)C2=C1CN(CCCNC=1NC3=CC=CC=C3N=1)CC2 IRBXWOSHUFMZCL-UHFFFAOYSA-N 0.000 description 1
- 230000003880 negative regulation of appetite Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000019818 neurotransmitter uptake Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 208000004259 scirrhous adenocarcinoma Diseases 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 230000000697 serotonin reuptake Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000004544 spot-on Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97202761A EP0905136A1 (fr) | 1997-09-08 | 1997-09-08 | Tétrahydro gamma-carbolines |
| PCT/EP1998/005710 WO1999012926A1 (fr) | 1997-09-08 | 1998-09-01 | Tetrahydro gamma-carbolines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20000737D0 NO20000737D0 (no) | 2000-02-14 |
| NO20000737L NO20000737L (no) | 2000-05-08 |
| NO315236B1 true NO315236B1 (no) | 2003-08-04 |
Family
ID=8228715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20000737A NO315236B1 (no) | 1997-09-08 | 2000-02-14 | Tetrahydro gamma-karboliner, deres fremstilling og farmasöytiske sammensetninger inneholdende det samme |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US6303614B1 (fr) |
| EP (2) | EP0905136A1 (fr) |
| JP (1) | JP2001515899A (fr) |
| KR (1) | KR100603896B1 (fr) |
| CN (1) | CN1110496C (fr) |
| AT (1) | ATE243209T1 (fr) |
| AU (1) | AU752410B2 (fr) |
| BR (1) | BR9811769A (fr) |
| CA (1) | CA2301807A1 (fr) |
| CZ (1) | CZ297220B6 (fr) |
| DE (1) | DE69815700T2 (fr) |
| EE (1) | EE04496B1 (fr) |
| ES (1) | ES2202902T3 (fr) |
| HK (1) | HK1029107A1 (fr) |
| HR (1) | HRP20000108A2 (fr) |
| HU (1) | HUP0003577A3 (fr) |
| ID (1) | ID23954A (fr) |
| IL (1) | IL134894A (fr) |
| MY (1) | MY129176A (fr) |
| NO (1) | NO315236B1 (fr) |
| NZ (1) | NZ503096A (fr) |
| PL (1) | PL191863B1 (fr) |
| RU (1) | RU2208614C2 (fr) |
| SK (1) | SK285594B6 (fr) |
| TR (1) | TR200000616T2 (fr) |
| TW (1) | TW531539B (fr) |
| WO (1) | WO1999012926A1 (fr) |
| ZA (1) | ZA988161B (fr) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1944306A1 (fr) * | 2003-09-17 | 2008-07-16 | Janssen Pharmaceutica, N.V. | Composés hétérocycliques fusionnés |
| CN1882590B (zh) * | 2003-09-17 | 2014-03-05 | 詹森药业有限公司 | 作为血清素受体调节剂的稠合杂环化合物 |
| CN103788089A (zh) * | 2003-09-17 | 2014-05-14 | 詹森药业有限公司 | 作为血清素受体调节剂的稠合杂环化合物 |
| EP1757605A4 (fr) * | 2004-04-12 | 2007-12-19 | Taisho Pharmaceutical Co Ltd | Composé amine cyclique |
| EP1856126A2 (fr) | 2005-02-17 | 2007-11-21 | Wyeth a Corporation of the State of Delaware | Derive d'indole, benzothiophene, benzofurane et indene a fusion cycloalkyle |
| FR2885905A1 (fr) * | 2005-05-23 | 2006-11-24 | Trophos Sa | Nouveaux composes chimiques et leurs utilisations comme medicament |
| WO2007009485A1 (fr) * | 2005-07-22 | 2007-01-25 | Pharma C S.A. | Derives de 8-phenoxy-y-carboline substitues a activite 5ht1 |
| WO2007058580A1 (fr) * | 2005-11-15 | 2007-05-24 | Astrazeneca Ab | Nouveaux derives de 2-aminopyrimidinone et leur utilisation |
| US7637410B2 (en) * | 2006-10-06 | 2009-12-29 | Tyco Healthcare Group Lp | Surgical instrument including a locking assembly |
| MX2010003149A (es) * | 2007-09-20 | 2010-11-10 | D2E Llc | Derivados que contienen fluor de pirido[4,3-b]indoles hidrogenados con propiedades neuroprotectoras y de mejoramiento de cognicion, proceso de preparacion y uso. |
| WO2009082268A2 (fr) | 2007-12-21 | 2009-07-02 | Alla Chem, Llc | Ligands dalpha-adrénorécepteurs, de récepteurs de dopamine, de l'histamine, d'imidazoline et de sérotonine ainsi que leurs procédés d'utilisation |
| RU2374245C1 (ru) | 2008-08-22 | 2009-11-27 | Андрей Александрович Иващенко | Лиганд с широким спектром одновременной рецепторной активности, фармацевтическая композиция, способ ее получения и лекарственное средство |
| CN105399674B (zh) | 2015-12-31 | 2017-02-15 | 青岛清原化合物有限公司 | 吡唑类化合物或其盐、制备方法、除草剂组合物及用途 |
| CN106631941B (zh) * | 2016-12-30 | 2018-09-28 | 青岛瀚生生物科技股份有限公司 | 一种2-甲基-3氯苯基甲硫醚的制备方法 |
| GB201704325D0 (en) * | 2017-03-17 | 2017-05-03 | Argonaut Therapeutics Ltd | Compounds |
| CN110698474B (zh) * | 2019-11-14 | 2021-11-02 | 福州大学 | 一种α位取代四氢-γ-咔啉类化合物及其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3410286C2 (de) * | 1984-03-21 | 1986-01-23 | Fresenius AG, 6380 Bad Homburg | Verfahren zur Trennung von Blut sowie Vorrichtung zur Durchführung des Verfahrens |
| US4672117A (en) * | 1985-09-16 | 1987-06-09 | American Home Products Corporation | Antipsychotic gamma-carbolines |
| US4798896A (en) * | 1988-01-19 | 1989-01-17 | American Home Products Corporation | Antipsychotic gamma-carboline N-oxides |
| EP0705832B1 (fr) * | 1994-09-12 | 2003-08-13 | Eli Lilly And Company Limited | Modulateurs serotonergiques |
-
1997
- 1997-09-08 EP EP97202761A patent/EP0905136A1/fr not_active Withdrawn
-
1998
- 1998-09-01 CZ CZ20000726A patent/CZ297220B6/cs not_active IP Right Cessation
- 1998-09-01 TR TR2000/00616T patent/TR200000616T2/xx unknown
- 1998-09-01 CA CA002301807A patent/CA2301807A1/fr not_active Abandoned
- 1998-09-01 WO PCT/EP1998/005710 patent/WO1999012926A1/fr active IP Right Grant
- 1998-09-01 EE EEP200000059A patent/EE04496B1/xx not_active IP Right Cessation
- 1998-09-01 AU AU97421/98A patent/AU752410B2/en not_active Ceased
- 1998-09-01 RU RU2000109310/04A patent/RU2208614C2/ru not_active IP Right Cessation
- 1998-09-01 JP JP2000510733A patent/JP2001515899A/ja not_active Withdrawn
- 1998-09-01 ES ES98951365T patent/ES2202902T3/es not_active Expired - Lifetime
- 1998-09-01 CN CN98808818A patent/CN1110496C/zh not_active Expired - Fee Related
- 1998-09-01 KR KR1020007000970A patent/KR100603896B1/ko not_active IP Right Cessation
- 1998-09-01 PL PL339143A patent/PL191863B1/pl not_active IP Right Cessation
- 1998-09-01 BR BR9811769-6A patent/BR9811769A/pt not_active Application Discontinuation
- 1998-09-01 US US09/508,240 patent/US6303614B1/en not_active Expired - Fee Related
- 1998-09-01 DE DE69815700T patent/DE69815700T2/de not_active Expired - Fee Related
- 1998-09-01 EP EP98951365A patent/EP1015451B1/fr not_active Expired - Lifetime
- 1998-09-01 NZ NZ503096A patent/NZ503096A/en unknown
- 1998-09-01 AT AT98951365T patent/ATE243209T1/de not_active IP Right Cessation
- 1998-09-01 IL IL13489498A patent/IL134894A/xx not_active IP Right Cessation
- 1998-09-01 SK SK299-2000A patent/SK285594B6/sk unknown
- 1998-09-01 ID IDW20000432A patent/ID23954A/id unknown
- 1998-09-02 TW TW087114508A patent/TW531539B/zh not_active IP Right Cessation
- 1998-09-07 ZA ZA9808161A patent/ZA988161B/xx unknown
- 1998-09-07 MY MYPI98004080A patent/MY129176A/en unknown
- 1998-09-08 HU HU0003577A patent/HUP0003577A3/hu unknown
-
2000
- 2000-02-14 NO NO20000737A patent/NO315236B1/no unknown
- 2000-02-29 HR HR20000108A patent/HRP20000108A2/xx not_active Application Discontinuation
- 2000-11-10 HK HK00107165A patent/HK1029107A1/xx not_active IP Right Cessation
-
2001
- 2001-08-15 US US09/930,005 patent/US6506768B2/en not_active Expired - Fee Related
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