CN1090628C - 新的n－芳基哌啶化合物,其制备方法和含有它们的药物组合物 - Google Patents
新的n－芳基哌啶化合物,其制备方法和含有它们的药物组合物 Download PDFInfo
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- CN1090628C CN1090628C CN98109437A CN98109437A CN1090628C CN 1090628 C CN1090628 C CN 1090628C CN 98109437 A CN98109437 A CN 98109437A CN 98109437 A CN98109437 A CN 98109437A CN 1090628 C CN1090628 C CN 1090628C
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- Prior art keywords
- dihydro
- piperidin
- fumarate
- amine
- benzo dioxine
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- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 208000024732 dysthymic disease Diseases 0.000 description 1
- 230000008451 emotion Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 235000013569 fruit product Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical group NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 239000004002 serotonin 1B agonist Substances 0.000 description 1
- 239000004000 serotonin 1B antagonist Substances 0.000 description 1
- 239000004001 serotonin 1D antagonist Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-N sodium;5-ethyl-5-pentan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)NC1=O QGMRQYFBGABWDR-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 210000003901 trigeminal nerve Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000002227 vasoactive effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Hematology (AREA)
- Obesity (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Addiction (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9703760A FR2761358B1 (fr) | 1997-03-27 | 1997-03-27 | Nouveaux composes de n-aryl piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR9703760 | 1997-03-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1197072A CN1197072A (zh) | 1998-10-28 |
| CN1090628C true CN1090628C (zh) | 2002-09-11 |
Family
ID=9505236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98109437A Expired - Fee Related CN1090628C (zh) | 1997-03-27 | 1998-03-26 | 新的n－芳基哌啶化合物,其制备方法和含有它们的药物组合物 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5965575A (enExample) |
| EP (1) | EP0867436B1 (enExample) |
| JP (1) | JPH10279578A (enExample) |
| CN (1) | CN1090628C (enExample) |
| AT (1) | ATE268767T1 (enExample) |
| AU (1) | AU731018B2 (enExample) |
| BR (1) | BR9803295A (enExample) |
| CA (1) | CA2232116C (enExample) |
| DE (1) | DE69824332T2 (enExample) |
| DK (1) | DK0867436T3 (enExample) |
| ES (1) | ES2223110T3 (enExample) |
| FR (1) | FR2761358B1 (enExample) |
| NO (1) | NO314628B1 (enExample) |
| NZ (1) | NZ330041A (enExample) |
| PL (1) | PL194118B1 (enExample) |
| PT (1) | PT867436E (enExample) |
| ZA (1) | ZA982607B (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2782515B1 (fr) * | 1998-08-21 | 2000-09-22 | Adir | NOUVEAUX DERIVES DE L'INDANE-1-Ol, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT |
| US6225324B1 (en) * | 1999-01-28 | 2001-05-01 | Bristol-Myers Squibb Company | Antidepressant heterocyclic compounds |
| PT1189900E (pt) * | 1999-06-30 | 2004-05-31 | Bristol Myers Squibb Co | Derivados de aminopirrolidina heterociclicos utilizados como agentes melatonergicos |
| GB0013737D0 (en) | 2000-06-07 | 2000-07-26 | Astrazeneca Ab | Novel compounds |
| SE0103650D0 (sv) * | 2001-11-01 | 2001-11-01 | Astrazeneca Ab | Therapeutic heterocyclic compounds |
| SE0103646D0 (sv) * | 2001-11-01 | 2001-11-01 | Astrazeneca Ab | Therapeutic chroman compounds |
| KR100864356B1 (ko) * | 2001-01-16 | 2008-10-17 | 아스트라제네카 아베 | 치료용 헤테로시클릭 화합물 |
| NZ526699A (en) * | 2001-01-16 | 2005-03-24 | Astrazeneca Ab | 8-amino derivatives and their use in treating migraine |
| US6713479B2 (en) * | 2001-03-02 | 2004-03-30 | Sepracor Inc. | Piperidine-piperazine ligands for neurotransmitter receptors |
| SE0103836D0 (sv) * | 2001-11-16 | 2001-11-16 | Astrazeneca Ab | Novel compounds |
| 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 |
| SE0300480D0 (sv) | 2003-02-21 | 2003-02-21 | Astrazeneca Ab | Novel compounds |
| GB0312609D0 (en) | 2003-06-02 | 2003-07-09 | Astrazeneca Ab | Novel compounds |
| TW200510407A (en) * | 2003-06-30 | 2005-03-16 | Altana Pharma Ag | Novel pyrrolodihydroisoquinolines as PDE 10 inhibitors |
| US20070105840A1 (en) * | 2003-06-30 | 2007-05-10 | Altana Pharma Ag | Pyrrolo-dihydroisoquinoline derivatives as pde10 inhibitors |
| JP4591349B2 (ja) * | 2003-07-14 | 2010-12-01 | 宇部興産株式会社 | ４−アミノテトラヒドロピラン化合物及びその酸塩の製法、その合成中間体およびその製法 |
| AR045258A1 (es) * | 2003-08-21 | 2005-10-19 | Altana Pharma Ag | Un producto farmaceutico para inyeccion |
| US20060085924A1 (en) * | 2004-10-13 | 2006-04-27 | Gaelle Brun | Coloring composition comprising at least one pigment and at least one electrophilic cyanoacrylate monomer |
| EP1838708A2 (en) * | 2005-01-12 | 2007-10-03 | Nycomed GmbH | Pyrrolodihydroisoquinolines as antiproliferative agents |
| EP1838707B1 (en) * | 2005-01-12 | 2009-04-29 | Nycomed GmbH | Novel pyrrolodihydroisoquinolines as pde10 inhibitors |
| US8599822B2 (en) * | 2005-03-23 | 2013-12-03 | Cisco Technology, Inc. | Slot-based transmission synchronization mechanism in wireless mesh networks |
| FR2884251B1 (fr) * | 2005-04-08 | 2007-07-13 | Servier Lab | Derives de piperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| UY29892A1 (es) * | 2005-11-04 | 2007-06-29 | Astrazeneca Ab | Nuevos derivados de cromano, composiciones farmaceuticas conteniendolos, procesos de preparacion y aplicaciones |
| JP5682051B2 (ja) | 2006-05-18 | 2015-03-11 | ファーマサイクリックス，インク． | 細胞内キナーゼ阻害剤 |
| ES2388454T3 (es) | 2007-03-22 | 2012-10-15 | Astrazeneca Ab | Derivados de quinolina para el tratamiento de enfermedades inflamatorias |
| PE20091036A1 (es) | 2007-11-30 | 2009-08-15 | Astrazeneca Ab | Derivado de quinolina como antagonista del receptor p2x7 |
| TW200944523A (en) * | 2008-02-08 | 2009-11-01 | Organon Nv | (Dihydro)pyrrolo[2,1-a]isoquinolines |
| WO2020183011A1 (en) | 2019-03-14 | 2020-09-17 | Institut Curie | Htr1d inhibitors and uses thereof in the treatment of cancer |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995007274A1 (en) * | 1993-09-06 | 1995-03-16 | Knoll Ag | Bicyclic aromatic compounds as therapeutic agents |
| US5464834A (en) * | 1992-06-12 | 1995-11-07 | Adir Et Compagnie | N-substituted N'-heterobicyclic piperazines having pharmaceutical activity |
| EP0745598A1 (fr) * | 1995-05-31 | 1996-12-04 | Adir Et Compagnie | Nouveaux composés de la pipérazine, de la pipéridine et de la 1,2,5,6-tétra-hydropyridine, leur procédé de préparation et les compositions pharmaceutiques les contenant |
-
1997
- 1997-03-27 FR FR9703760A patent/FR2761358B1/fr not_active Expired - Fee Related
-
1998
- 1998-03-12 CA CA002232116A patent/CA2232116C/fr not_active Expired - Fee Related
- 1998-03-26 DE DE69824332T patent/DE69824332T2/de not_active Expired - Fee Related
- 1998-03-26 AT AT98400711T patent/ATE268767T1/de not_active IP Right Cessation
- 1998-03-26 CN CN98109437A patent/CN1090628C/zh not_active Expired - Fee Related
- 1998-03-26 PT PT98400711T patent/PT867436E/pt unknown
- 1998-03-26 PL PL325575A patent/PL194118B1/pl not_active IP Right Cessation
- 1998-03-26 NZ NZ330041A patent/NZ330041A/xx unknown
- 1998-03-26 DK DK98400711T patent/DK0867436T3/da active
- 1998-03-26 EP EP98400711A patent/EP0867436B1/fr not_active Expired - Lifetime
- 1998-03-26 ES ES98400711T patent/ES2223110T3/es not_active Expired - Lifetime
- 1998-03-27 AU AU59677/98A patent/AU731018B2/en not_active Ceased
- 1998-03-27 NO NO19981415A patent/NO314628B1/no unknown
- 1998-03-27 US US09/049,233 patent/US5965575A/en not_active Expired - Fee Related
- 1998-03-27 JP JP10081710A patent/JPH10279578A/ja active Pending
- 1998-03-27 BR BR9803295A patent/BR9803295A/pt not_active Application Discontinuation
- 1998-03-27 ZA ZA982607A patent/ZA982607B/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5464834A (en) * | 1992-06-12 | 1995-11-07 | Adir Et Compagnie | N-substituted N'-heterobicyclic piperazines having pharmaceutical activity |
| WO1995007274A1 (en) * | 1993-09-06 | 1995-03-16 | Knoll Ag | Bicyclic aromatic compounds as therapeutic agents |
| EP0745598A1 (fr) * | 1995-05-31 | 1996-12-04 | Adir Et Compagnie | Nouveaux composés de la pipérazine, de la pipéridine et de la 1,2,5,6-tétra-hydropyridine, leur procédé de préparation et les compositions pharmaceutiques les contenant |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10279578A (ja) | 1998-10-20 |
| PT867436E (pt) | 2004-09-30 |
| NZ330041A (en) | 1999-01-28 |
| PL194118B1 (pl) | 2007-04-30 |
| CA2232116C (fr) | 2003-09-16 |
| DE69824332D1 (de) | 2004-07-15 |
| US5965575A (en) | 1999-10-12 |
| FR2761358A1 (fr) | 1998-10-02 |
| ES2223110T3 (es) | 2005-02-16 |
| NO314628B1 (no) | 2003-04-22 |
| DE69824332T2 (de) | 2005-06-16 |
| DK0867436T3 (da) | 2004-10-04 |
| ZA982607B (en) | 1998-09-30 |
| AU5967798A (en) | 1998-10-01 |
| AU731018B2 (en) | 2001-03-22 |
| ATE268767T1 (de) | 2004-06-15 |
| NO981415L (no) | 1998-09-28 |
| NO981415D0 (no) | 1998-03-27 |
| FR2761358B1 (fr) | 1999-05-07 |
| PL325575A1 (en) | 1998-09-28 |
| BR9803295A (pt) | 2000-03-21 |
| EP0867436A1 (fr) | 1998-09-30 |
| EP0867436B1 (fr) | 2004-06-09 |
| CN1197072A (zh) | 1998-10-28 |
| CA2232116A1 (fr) | 1998-09-27 |
| HK1014954A1 (en) | 1999-10-08 |
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