NO323236B1 - Indolderivater, deres anvendelse og farmasoytiske sammensetninger omfattende disse - Google Patents
Indolderivater, deres anvendelse og farmasoytiske sammensetninger omfattende disse Download PDFInfo
- Publication number
- NO323236B1 NO323236B1 NO20026005A NO20026005A NO323236B1 NO 323236 B1 NO323236 B1 NO 323236B1 NO 20026005 A NO20026005 A NO 20026005A NO 20026005 A NO20026005 A NO 20026005A NO 323236 B1 NO323236 B1 NO 323236B1
- Authority
- NO
- Norway
- Prior art keywords
- dihydro
- indole
- piperidin
- fluoro
- quinolin
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 150000002475 indoles Chemical class 0.000 title claims description 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 112
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 46
- 230000000694 effects Effects 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 229940079593 drug Drugs 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 201000000980 schizophrenia Diseases 0.000 claims description 11
- 208000024891 symptom Diseases 0.000 claims description 11
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 208000028017 Psychotic disease Diseases 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 5
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 5
- 208000019695 Migraine disease Diseases 0.000 claims description 5
- 239000000164 antipsychotic agent Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 206010027599 migraine Diseases 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 230000006872 improvement Effects 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 208000011688 Generalised anxiety disease Diseases 0.000 claims description 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
- 230000016571 aggressive behavior Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 3
- 208000019906 panic disease Diseases 0.000 claims description 3
- 230000007958 sleep Effects 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- FAYLLIQOZYADJB-UHFFFAOYSA-N 1-(3,4-dihydro-2h-quinolin-1-yl)-4-[4-(4-fluoro-1h-indol-3-yl)piperidin-1-yl]butan-1-one Chemical compound C1CCC2=CC=CC=C2N1C(=O)CCCN(CC1)CCC1C1=CNC2=C1C(F)=CC=C2 FAYLLIQOZYADJB-UHFFFAOYSA-N 0.000 claims description 2
- CKHXYJHHWFPINQ-UHFFFAOYSA-N 4-[4-(5-chloro-1h-indol-3-yl)piperidin-1-yl]-1-(3,4-dihydro-2h-quinolin-1-yl)butan-1-one Chemical compound C1CCC2=CC=CC=C2N1C(=O)CCCN(CC1)CCC1C1=CNC2=CC=C(Cl)C=C21 CKHXYJHHWFPINQ-UHFFFAOYSA-N 0.000 claims description 2
- AXZHMCJZZKXAGI-UHFFFAOYSA-N 4-[4-(7-chloro-1h-indol-3-yl)piperidin-1-yl]-1-(3,4-dihydro-2h-quinolin-1-yl)butan-1-one Chemical compound C1CCC2=CC=CC=C2N1C(=O)CCCN(CC1)CCC1C1=CNC2=C1C=CC=C2Cl AXZHMCJZZKXAGI-UHFFFAOYSA-N 0.000 claims description 2
- SHOFJJYJPCUKIL-UHFFFAOYSA-N 4-[4-[4-(5-fluoro-1h-indol-3-yl)piperidin-1-yl]butyl]-1,4-benzoxazin-3-one Chemical compound O=C1COC2=CC=CC=C2N1CCCCN(CC1)CCC1C1=CNC2=CC=C(F)C=C21 SHOFJJYJPCUKIL-UHFFFAOYSA-N 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
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- LBQPBGAWOICMMY-UHFFFAOYSA-N 1-(3,4-dihydro-1h-isoquinolin-2-yl)-3-[4-(5-fluoro-1h-indol-3-yl)piperidin-1-yl]propan-1-one Chemical compound C1CC2=CC=CC=C2CN1C(=O)CCN(CC1)CCC1C1=CNC2=CC=C(F)C=C21 LBQPBGAWOICMMY-UHFFFAOYSA-N 0.000 claims 1
- QKDAJRUPDKYNRO-UHFFFAOYSA-N 1-(3,4-dihydro-1h-isoquinolin-2-yl)-4-[4-(4-fluoro-1h-indol-3-yl)piperidin-1-yl]butan-1-one Chemical compound C1CC2=CC=CC=C2CN1C(=O)CCCN(CC1)CCC1C1=CNC2=C1C(F)=CC=C2 QKDAJRUPDKYNRO-UHFFFAOYSA-N 0.000 claims 1
- UOPZVMQSXQGJPX-UHFFFAOYSA-N 1-(3,4-dihydro-1h-isoquinolin-2-yl)-4-[4-(5-fluoro-1h-indol-3-yl)piperidin-1-yl]butan-1-one Chemical compound C1CC2=CC=CC=C2CN1C(=O)CCCN(CC1)CCC1C1=CNC2=CC=C(F)C=C21 UOPZVMQSXQGJPX-UHFFFAOYSA-N 0.000 claims 1
- WNPFFSLNMCAVDB-UHFFFAOYSA-N 1-(3,4-dihydro-1h-isoquinolin-2-yl)-5-[4-(5-fluoro-1h-indol-3-yl)piperidin-1-yl]pentan-1-one Chemical compound C1CC2=CC=CC=C2CN1C(=O)CCCCN(CC1)CCC1C1=CNC2=CC=C(F)C=C21 WNPFFSLNMCAVDB-UHFFFAOYSA-N 0.000 claims 1
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- NMDUEZSJYPLVLS-UHFFFAOYSA-N 1-(3,4-dihydro-2h-quinolin-1-yl)-3-[4-(5-fluoro-1h-indol-3-yl)piperidin-1-yl]propan-1-one Chemical compound C1CCC2=CC=CC=C2N1C(=O)CCN(CC1)CCC1C1=CNC2=CC=C(F)C=C21 NMDUEZSJYPLVLS-UHFFFAOYSA-N 0.000 claims 1
- ARBGPUGFFUMXCU-UHFFFAOYSA-N 1-(3,4-dihydro-2h-quinolin-1-yl)-4-[4-(5-fluoro-1h-indol-3-yl)piperidin-1-yl]butan-1-one Chemical compound C1CCC2=CC=CC=C2N1C(=O)CCCN(CC1)CCC1C1=CNC2=CC=C(F)C=C21 ARBGPUGFFUMXCU-UHFFFAOYSA-N 0.000 claims 1
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- RRJSVTKIKRWIOS-UHFFFAOYSA-N 1-(3,4-dihydro-2h-quinolin-1-yl)-6-[4-(5-fluoro-1h-indol-3-yl)piperidin-1-yl]hexan-1-one Chemical compound C1CCC2=CC=CC=C2N1C(=O)CCCCCN(CC1)CCC1C1=CNC2=CC=C(F)C=C21 RRJSVTKIKRWIOS-UHFFFAOYSA-N 0.000 claims 1
- JFSOFXZDECSVCC-UHFFFAOYSA-N 1-[3-[4-(5-chloro-1h-indol-3-yl)piperidin-1-yl]propyl]-3,4-dihydroquinolin-2-one Chemical compound O=C1CCC2=CC=CC=C2N1CCCN(CC1)CCC1C1=CNC2=CC=C(Cl)C=C21 JFSOFXZDECSVCC-UHFFFAOYSA-N 0.000 claims 1
- USLDVLHOXAMFMO-UHFFFAOYSA-N 1-[3-[4-(5-fluoro-1-methylindol-3-yl)piperidin-1-yl]propyl]-3,4-dihydroquinolin-2-one Chemical compound C12=CC(F)=CC=C2N(C)C=C1C1CCN(CCCN2C3=CC=CC=C3CCC2=O)CC1 USLDVLHOXAMFMO-UHFFFAOYSA-N 0.000 claims 1
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- SWSVBXDGTNXZPC-UHFFFAOYSA-N 1-[4-[4-(5-fluoro-1h-indol-3-yl)-3,6-dihydro-2h-pyridin-1-yl]butyl]-3,4-dihydroquinolin-2-one Chemical compound O=C1CCC2=CC=CC=C2N1CCCCN(CC1)CC=C1C1=CNC2=CC=C(F)C=C21 SWSVBXDGTNXZPC-UHFFFAOYSA-N 0.000 claims 1
- PWJRYZJSQMCNJJ-UHFFFAOYSA-N 1-[4-[4-(5-fluoro-1h-indol-3-yl)piperidin-1-yl]butyl]-3,4-dihydroquinolin-2-one Chemical compound O=C1CCC2=CC=CC=C2N1CCCCN(CC1)CCC1C1=CNC2=CC=C(F)C=C21 PWJRYZJSQMCNJJ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
-
- 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
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200000919 | 2000-06-14 | ||
| US21244500P | 2000-06-16 | 2000-06-16 | |
| PCT/DK2001/000406 WO2001096328A1 (en) | 2000-06-14 | 2001-06-13 | Indole derivatives useful for the treatment of cns disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20026005D0 NO20026005D0 (no) | 2002-12-13 |
| NO20026005L NO20026005L (no) | 2002-12-13 |
| NO323236B1 true NO323236B1 (no) | 2007-02-05 |
Family
ID=26068835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20026005A NO323236B1 (no) | 2000-06-14 | 2002-12-13 | Indolderivater, deres anvendelse og farmasoytiske sammensetninger omfattende disse |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US6890916B2 (pt) |
| EP (1) | EP1294710B1 (pt) |
| JP (1) | JP2004503550A (pt) |
| KR (1) | KR20030007967A (pt) |
| AR (1) | AR028685A1 (pt) |
| AT (2) | ATE297391T1 (pt) |
| AU (2) | AU2001273881B8 (pt) |
| BG (1) | BG107449A (pt) |
| CA (1) | CA2411412C (pt) |
| CZ (1) | CZ200335A3 (pt) |
| DE (2) | DE60130691T2 (pt) |
| DK (1) | DK1468996T3 (pt) |
| ES (2) | ES2290587T3 (pt) |
| HR (1) | HRP20021008A2 (pt) |
| HU (1) | HUP0301735A2 (pt) |
| NO (1) | NO323236B1 (pt) |
| NZ (1) | NZ523076A (pt) |
| PT (2) | PT1468996E (pt) |
| SG (1) | SG148840A1 (pt) |
| WO (1) | WO2001096328A1 (pt) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2165274B1 (es) * | 1999-06-04 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de indolilpiperidina como agentes antihistaminicos y antialergicos. |
| EP1468996B1 (en) * | 2000-06-14 | 2007-09-26 | H. Lundbeck A/S | Indole derivatives for the treatment of CNS disorders |
| ES2172436B1 (es) | 2000-10-31 | 2004-01-16 | Almirall Prodesfarma Sa | Derivados de indolilpiperidina como agentes antihistaminicos y antialergicos. |
| AU2003236207A1 (en) * | 2002-05-31 | 2003-12-19 | H. Lundbeck A/S | The hydrochloride of (s)-(+)-3-(1-(2-(1-acetyl-2,3-dihydro-1h-indol-3-yl)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-6-chloro-1h-indole |
| WO2004020437A1 (en) * | 2002-08-29 | 2004-03-11 | H. Lundbeck A/S | S-(+)-3-{1-[2-(2,3-dihydro-1h-indol-3-yl)ethyl]-3,6-dihydro-2h-pyridin-4-yl}-6-chloro-1h-indole and acid addition salts thereof |
| GB0306604D0 (en) * | 2003-03-21 | 2003-04-30 | Curidium Ltd | Second medical use |
| WO2004108671A1 (en) * | 2003-06-06 | 2004-12-16 | Suven Life Sciences Limited | Substituted indoles with serotonin receptor affinity, process for their preparation and pharmaceutical compositions containing them |
| GB0708186D0 (en) * | 2007-04-27 | 2007-06-06 | Merck Sharp & Dohme | Therapeutic compounds |
| SE531698C2 (sv) | 2007-07-12 | 2009-07-07 | Respiratorius Ab | Nya bronkdilaterande a,b-omättade amider |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9202915D0 (en) * | 1992-02-12 | 1992-03-25 | Wellcome Found | Chemical compounds |
| ZA9711376B (en) * | 1996-12-20 | 1998-07-21 | Lundbeck & Co As H | Indole or dihydroindole derivatives |
| AU8743098A (en) * | 1997-08-22 | 1999-03-16 | Eli Lilly And Company Limited | Benzothiadiazinyl-indole derivatives and their use as serotonin receptor ligands |
| GB9718833D0 (en) * | 1997-09-04 | 1997-11-12 | Merck Sharp & Dohme | Therapeutic agents |
| GB9810886D0 (en) * | 1998-05-13 | 1998-07-22 | Lilly Industries Ltd | Pharmaceutical compounds |
| GB9825413D0 (en) * | 1998-11-19 | 1999-01-13 | Lilly Co Eli | Pharmaceutical compounds |
| WO2000040581A1 (en) * | 1999-01-07 | 2000-07-13 | American Home Products Corporation | 3,4-dihydro-2h-benzo[1,4]oxazine derivatives |
| CA2373855A1 (en) * | 1999-05-12 | 2000-11-23 | Solvay Pharmaceuticals B.V. | Method of treating psychotic disorders |
| WO2000078716A1 (fr) * | 1999-06-24 | 2000-12-28 | Toray Industries, Inc. | ANTAGONISTES DU RECEPTEUR ADRENERGIQUE-α¿1B? |
| GB2362381A (en) * | 2000-05-18 | 2001-11-21 | Lilly Co Eli | Pharmaceutically active indolyl-piperidines |
-
2001
- 2001-06-06 AR ARP010102697A patent/AR028685A1/es not_active Application Discontinuation
- 2001-06-13 HU HU0301735A patent/HUP0301735A2/hu unknown
- 2001-06-13 ES ES04012325T patent/ES2290587T3/es not_active Expired - Lifetime
- 2001-06-13 PT PT04012325T patent/PT1468996E/pt unknown
- 2001-06-13 DK DK04012325T patent/DK1468996T3/da active
- 2001-06-13 AU AU2001273881A patent/AU2001273881B8/en not_active Ceased
- 2001-06-13 SG SG200501564-9A patent/SG148840A1/en unknown
- 2001-06-13 KR KR1020027017034A patent/KR20030007967A/ko active IP Right Grant
- 2001-06-13 AT AT01940240T patent/ATE297391T1/de not_active IP Right Cessation
- 2001-06-13 WO PCT/DK2001/000406 patent/WO2001096328A1/en active IP Right Grant
- 2001-06-13 NZ NZ523076A patent/NZ523076A/en unknown
- 2001-06-13 CA CA002411412A patent/CA2411412C/en not_active Expired - Fee Related
- 2001-06-13 DE DE60130691T patent/DE60130691T2/de not_active Expired - Fee Related
- 2001-06-13 PT PT01940240T patent/PT1294710E/pt unknown
- 2001-06-13 CZ CZ200335A patent/CZ200335A3/cs unknown
- 2001-06-13 AT AT04012325T patent/ATE374197T1/de not_active IP Right Cessation
- 2001-06-13 ES ES01940240T patent/ES2243508T3/es not_active Expired - Lifetime
- 2001-06-13 AU AU7388101A patent/AU7388101A/xx active Pending
- 2001-06-13 DE DE60111379T patent/DE60111379T2/de not_active Expired - Fee Related
- 2001-06-13 JP JP2002510470A patent/JP2004503550A/ja active Pending
- 2001-06-13 EP EP01940240A patent/EP1294710B1/en not_active Expired - Lifetime
-
2002
- 2002-12-09 US US10/315,927 patent/US6890916B2/en not_active Expired - Fee Related
- 2002-12-13 NO NO20026005A patent/NO323236B1/no unknown
- 2002-12-17 HR HR20021008A patent/HRP20021008A2/hr not_active Application Discontinuation
-
2003
- 2003-01-08 BG BG107449A patent/BG107449A/bg unknown
-
2005
- 2005-03-03 US US11/073,497 patent/US7276508B2/en not_active Expired - Fee Related
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