SK285594B6 - Gama-karbolín, spôsob jeho prípravy a kompozícia s jeho obsahom - Google Patents
Gama-karbolín, spôsob jeho prípravy a kompozícia s jeho obsahom Download PDFInfo
- Publication number
- SK285594B6 SK285594B6 SK299-2000A SK2992000A SK285594B6 SK 285594 B6 SK285594 B6 SK 285594B6 SK 2992000 A SK2992000 A SK 2992000A SK 285594 B6 SK285594 B6 SK 285594B6
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- SK
- Slovakia
- Prior art keywords
- formula
- alkyl
- radical
- hydrogen
- gamma
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- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 16
- RDMFHRSPDKWERA-UHFFFAOYSA-N 5H-Pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=CC=C3NC2=C1 RDMFHRSPDKWERA-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 230000008569 process Effects 0.000 title claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 29
- 150000002367 halogens Chemical class 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 88
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- -1 amino, hydroxy Chemical group 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
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- 239000002585 base Substances 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000012442 inert solvent Substances 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- RPROHCOBMVQVIV-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole Chemical class N1C2=CC=CC=C2C2=C1CCNC2 RPROHCOBMVQVIV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
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- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
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- 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 201000000980 schizophrenia Diseases 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
- AYGJDUHQRFKLBG-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;dihydrate Chemical compound O.O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 AYGJDUHQRFKLBG-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
- 210000003802 sputum Anatomy 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 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
- 125000003944 tolyl group Chemical group 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
- 239000008215 water for injection Substances 0.000 description 1
- 230000004580 weight loss Effects 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)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Anesthesiology (AREA)
- Child & Adolescent Psychology (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 (en) | 1997-09-08 | 1997-09-08 | Tetrahydro gamma-carbolines |
| PCT/EP1998/005710 WO1999012926A1 (en) | 1997-09-08 | 1998-09-01 | Tetrahydro gamma-carbolines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK2992000A3 SK2992000A3 (en) | 2001-03-12 |
| SK285594B6 true SK285594B6 (sk) | 2007-04-05 |
Family
ID=8228715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK299-2000A SK285594B6 (sk) | 1997-09-08 | 1998-09-01 | Gama-karbolín, spôsob jeho prípravy a kompozícia s jeho obsahom |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US6303614B1 (cs) |
| EP (2) | EP0905136A1 (cs) |
| JP (1) | JP2001515899A (cs) |
| KR (1) | KR100603896B1 (cs) |
| CN (1) | CN1110496C (cs) |
| AT (1) | ATE243209T1 (cs) |
| AU (1) | AU752410B2 (cs) |
| BR (1) | BR9811769A (cs) |
| CA (1) | CA2301807A1 (cs) |
| CZ (1) | CZ297220B6 (cs) |
| DE (1) | DE69815700T2 (cs) |
| EE (1) | EE04496B1 (cs) |
| ES (1) | ES2202902T3 (cs) |
| HR (1) | HRP20000108A2 (cs) |
| HU (1) | HUP0003577A3 (cs) |
| ID (1) | ID23954A (cs) |
| IL (1) | IL134894A (cs) |
| MY (1) | MY129176A (cs) |
| NO (1) | NO315236B1 (cs) |
| NZ (1) | NZ503096A (cs) |
| PL (1) | PL191863B1 (cs) |
| RU (1) | RU2208614C2 (cs) |
| SK (1) | SK285594B6 (cs) |
| TR (1) | TR200000616T2 (cs) |
| TW (1) | TW531539B (cs) |
| WO (1) | WO1999012926A1 (cs) |
| ZA (1) | ZA988161B (cs) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5069907B2 (ja) * | 2003-09-17 | 2012-11-07 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 縮合複素環式化合物 |
| CN101318962A (zh) * | 2003-09-17 | 2008-12-10 | 詹森药业有限公司 | 稠合杂环化合物 |
| EP1905774B1 (en) * | 2003-09-17 | 2013-02-20 | Janssen Pharmaceutica N.V. | Fused heterocyclic compounds as serotonin receptor modulators |
| CA2562406C (en) * | 2004-04-12 | 2013-03-19 | Taisho Pharmaceutical Co., Ltd. | Cyclic amine compound |
| WO2006089053A2 (en) | 2005-02-17 | 2006-08-24 | Wyeth | Cycloalkylfused indole, benzothiophene, benzofuran and indene derivatives |
| FR2885905A1 (fr) * | 2005-05-23 | 2006-11-24 | Trophos Sa | Nouveaux composes chimiques et leurs utilisations comme medicament |
| WO2007009485A1 (en) * | 2005-07-22 | 2007-01-25 | Pharma C S.A. | Substituted 8-phenoxy-y-carboline derivatives with 5ht1 activity |
| JP2009515949A (ja) * | 2005-11-15 | 2009-04-16 | アストラゼネカ・アクチエボラーグ | 新規な２−アミノピリミジノン誘導体およびそれらの使用 |
| US8584921B2 (en) * | 2006-10-06 | 2013-11-19 | Covidien Lp | Surgical instrument with articulating tool assembly |
| CA2700160A1 (en) * | 2007-09-20 | 2009-03-26 | D2E, Llc | Fluoro-containing derivatives of hydrogenated pyrido[4,3-b]indoles with neuroprotective and cognition enhancing properties, process for preparing, and use |
| WO2009082268A2 (ru) | 2007-12-21 | 2009-07-02 | Alla Chem, Llc | ЛИГАНДЫ α-АДРЕНОЦЕПТОРОВ, ДОПАМИНОВЫХ, ГИСТАМИНОВЫХ, ИМИДАЗОЛИНОВЫХ И СЕРОТОНИНОВЫХ РЕЦЕПТОРОВ И ИХ ПРИМЕНЕНИЕ |
| 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 |
| CA3194682A1 (en) * | 2020-10-09 | 2022-04-14 | Zehong Wan | Heterocyclic substituted fused .gamma.-carboline derivative, preparationmethod therefor, intermediate thereof and use thereof |
Family Cites Families (6)
| 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 |
| US4636563A (en) * | 1985-09-16 | 1987-01-13 | American Home Products Corporation | Antipsychotic γ-carbolines |
| US4798896A (en) * | 1988-01-19 | 1989-01-17 | American Home Products Corporation | Antipsychotic gamma-carboline N-oxides |
| RU2067980C1 (ru) * | 1992-06-30 | 1996-10-20 | Глэксо Груп Лимитед | Производные лактама и фармацевтическая композиция, являющаяся антагонистом 5-окситраптамина /5-нт/ на 5- нт3 -рецепторах или их физиологически приемлемые соли и соловаты |
| ES2204932T3 (es) * | 1994-09-12 | 2004-05-01 | Eli Lilly And Company Limited | Moduladores serotonergicos. |
-
1997
- 1997-09-08 EP EP97202761A patent/EP0905136A1/en not_active Withdrawn
-
1998
- 1998-09-01 JP JP2000510733A patent/JP2001515899A/ja not_active Withdrawn
- 1998-09-01 EE EEP200000059A patent/EE04496B1/xx not_active IP Right Cessation
- 1998-09-01 CZ CZ20000726A patent/CZ297220B6/cs not_active IP Right Cessation
- 1998-09-01 ID IDW20000432A patent/ID23954A/id unknown
- 1998-09-01 AU AU97421/98A patent/AU752410B2/en not_active Ceased
- 1998-09-01 ES ES98951365T patent/ES2202902T3/es not_active Expired - Lifetime
- 1998-09-01 HR HR20000108A patent/HRP20000108A2/xx not_active Application Discontinuation
- 1998-09-01 RU RU2000109310/04A patent/RU2208614C2/ru not_active IP Right Cessation
- 1998-09-01 US US09/508,240 patent/US6303614B1/en not_active Expired - Fee Related
- 1998-09-01 BR BR9811769-6A patent/BR9811769A/pt not_active Application Discontinuation
- 1998-09-01 PL PL339143A patent/PL191863B1/pl not_active IP Right Cessation
- 1998-09-01 EP EP98951365A patent/EP1015451B1/en not_active Expired - Lifetime
- 1998-09-01 KR KR1020007000970A patent/KR100603896B1/ko not_active Expired - Fee Related
- 1998-09-01 NZ NZ503096A patent/NZ503096A/en unknown
- 1998-09-01 IL IL13489498A patent/IL134894A/xx not_active IP Right Cessation
- 1998-09-01 CN CN98808818A patent/CN1110496C/zh not_active Expired - Fee Related
- 1998-09-01 CA CA002301807A patent/CA2301807A1/en not_active Abandoned
- 1998-09-01 WO PCT/EP1998/005710 patent/WO1999012926A1/en active IP Right Grant
- 1998-09-01 SK SK299-2000A patent/SK285594B6/sk unknown
- 1998-09-01 AT AT98951365T patent/ATE243209T1/de not_active IP Right Cessation
- 1998-09-01 DE DE69815700T patent/DE69815700T2/de not_active Expired - Fee Related
- 1998-09-01 TR TR2000/00616T patent/TR200000616T2/xx 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
-
2001
- 2001-08-15 US US09/930,005 patent/US6506768B2/en not_active Expired - Fee Related
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