JPH10279578A - 新規なアリールピペリジン化合物、その製造法、及びそれらを含む医薬組成物 - Google Patents
新規なアリールピペリジン化合物、その製造法、及びそれらを含む医薬組成物Info
- Publication number
- JPH10279578A JPH10279578A JP10081710A JP8171098A JPH10279578A JP H10279578 A JPH10279578 A JP H10279578A JP 10081710 A JP10081710 A JP 10081710A JP 8171098 A JP8171098 A JP 8171098A JP H10279578 A JPH10279578 A JP H10279578A
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- piperid
- benzodioxin
- amine
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 150000001412 amines Chemical class 0.000 claims abstract description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims abstract description 4
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- -1 2,3-dihydro [1, 4] Benzodioxin-5-yl Chemical group 0.000 claims description 45
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 45
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
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- 239000001257 hydrogen Substances 0.000 claims description 7
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
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- XUBOFCIEDMCFES-UHFFFAOYSA-N n-[2-(8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl)ethyl]-1-(6-fluoro-3,4-dihydro-2h-chromen-8-yl)piperidin-4-amine Chemical compound C1CCOC2=C1C=C(F)C=C2N(CC1)CCC1NCCC1=CN2CCC(C=C(C(=C3)OC)OC)=C3C2=C1 XUBOFCIEDMCFES-UHFFFAOYSA-N 0.000 claims description 2
- NESXRYWWENJSPU-UHFFFAOYSA-N n-benzyl-1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-[2-(2,3-dihydro-1h-inden-1-yl)ethyl]piperidin-4-amine Chemical compound C1CC2=CC=CC=C2C1CCN(C1CCN(CC1)C=1C=2OCCOC=2C=CC=1)CC1=CC=CC=C1 NESXRYWWENJSPU-UHFFFAOYSA-N 0.000 claims description 2
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- 231100000736 substance abuse Toxicity 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- PSUZUNWPCASNJA-UHFFFAOYSA-N 1-(3,4-dihydro-2h-chromen-8-yl)-n-[2-(8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl)ethyl]piperidin-4-amine Chemical compound C1CCOC2=C1C=CC=C2N(CC1)CCC1NCCC1=CN2CCC(C=C(C(=C3)OC)OC)=C3C2=C1 PSUZUNWPCASNJA-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- HBMUMVMGBLMQJT-UHFFFAOYSA-N pyrrolo[2,1-a]isoquinoline Chemical compound C12=CC=CC=C2C=CN2C1=CC=C2 HBMUMVMGBLMQJT-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
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- 229910052736 halogen Inorganic materials 0.000 abstract 2
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- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 62
- 239000000047 product Substances 0.000 description 41
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- RJVZEPWRJJBXLH-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-1-yl)acetic acid Chemical compound C1=CC=C2C(CC(=O)O)CCC2=C1 RJVZEPWRJJBXLH-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 102000005962 receptors Human genes 0.000 description 16
- 108020003175 receptors Proteins 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 238000012360 testing method Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- 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
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- 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
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- 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
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- 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)
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Addiction (AREA)
- Child & Adolescent Psychology (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9703760 | 1997-03-27 | ||
| 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 |
Publications (2)
| Publication Number | Publication Date |
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| JPH10279578A true JPH10279578A (ja) | 1998-10-20 |
| JPH10279578A5 JPH10279578A5 (enExample) | 2005-08-25 |
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| JP10081710A Pending JPH10279578A (ja) | 1997-03-27 | 1998-03-27 | 新規なアリールピペリジン化合物、その製造法、及びそれらを含む医薬組成物 |
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| EP (1) | EP0867436B1 (enExample) |
| JP (1) | JPH10279578A (enExample) |
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| 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) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003503492A (ja) * | 1999-06-30 | 2003-01-28 | ブリストルーマイヤーズ スクイブ カンパニー | メラトニン作用剤としての複素環式アミノピロリジン誘導体 |
| WO2005005406A1 (ja) * | 2003-07-14 | 2005-01-20 | Ube Industries, Ltd. | 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 |
| JP2006290890A (ja) * | 2005-04-08 | 2006-10-26 | Lab Servier | ピペラジン化合物、その製造方法およびそれを含有する医薬組成物 |
Families Citing this family (25)
| 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 |
| CA2360683A1 (en) * | 1999-01-28 | 2000-08-03 | Joseph P. Yevich | Antidepressant heterocyclic compounds |
| GB0013737D0 (en) | 2000-06-07 | 2000-07-26 | Astrazeneca Ab | Novel compounds |
| SE0103646D0 (sv) * | 2001-11-01 | 2001-11-01 | Astrazeneca Ab | Therapeutic chroman compounds |
| CN100384833C (zh) * | 2001-01-16 | 2008-04-30 | 阿斯特拉曾尼卡有限公司 | 治疗用苯并二氢吡喃化合物 |
| SE0103650D0 (sv) * | 2001-11-01 | 2001-11-01 | Astrazeneca Ab | Therapeutic heterocyclic compounds |
| JP4280067B2 (ja) | 2001-01-16 | 2009-06-17 | アストラゼネカ・アクチエボラーグ | 治療用ヘテロ環式化合物 |
| 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 |
| DE602004022415D1 (de) * | 2003-06-30 | 2009-09-17 | Nycomed Gmbh | Pyrrolo-dihydroisochinolin-derivate als pde10-inhibitoren |
| CA2530316A1 (en) * | 2003-06-30 | 2005-01-13 | Altana Pharma Ag | Pyrrolodihydroisoquinolines as pde10 inhibitors |
| 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 |
| ATE430148T1 (de) * | 2005-01-12 | 2009-05-15 | Nycomed Gmbh | Neue pyrrolodihydroisochinoline als pde10- inhibitoren |
| EP1838708A2 (en) * | 2005-01-12 | 2007-10-03 | Nycomed GmbH | Pyrrolodihydroisoquinolines as antiproliferative agents |
| US8599822B2 (en) * | 2005-03-23 | 2013-12-03 | Cisco Technology, Inc. | Slot-based transmission synchronization mechanism in wireless mesh networks |
| UY29892A1 (es) * | 2005-11-04 | 2007-06-29 | Astrazeneca Ab | Nuevos derivados de cromano, composiciones farmaceuticas conteniendolos, procesos de preparacion y aplicaciones |
| US8604031B2 (en) | 2006-05-18 | 2013-12-10 | Mannkind Corporation | Intracellular kinase inhibitors |
| KR20090122396A (ko) | 2007-03-22 | 2009-11-27 | 아스트라제네카 아베 | 염증성 질환 치료용 퀴놀린 유도체 |
| US8106073B2 (en) | 2007-11-30 | 2012-01-31 | Astrazeneca Ab | Quinoline derivatives 057 |
| 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 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2692264B1 (fr) * | 1992-06-12 | 1994-08-05 | Adir | Nouvelles piperazines 1,4-disubstituees, leur procede de preparation et les compositions pharmaceutiques les contenant. |
| GB9318431D0 (en) * | 1993-09-06 | 1993-10-20 | Boots Co Plc | Therapeutic agents |
| FR2734819B1 (fr) * | 1995-05-31 | 1997-07-04 | Adir | Nouveaux composes de la piperazine, de la piperidine et de la 1,2,5,6-tetrahydropyridine, leur procede de preparation 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 CN CN98109437A patent/CN1090628C/zh not_active Expired - Fee Related
- 1998-03-26 PL PL325575A patent/PL194118B1/pl not_active IP Right Cessation
- 1998-03-26 AT AT98400711T patent/ATE268767T1/de not_active IP Right Cessation
- 1998-03-26 NZ NZ330041A patent/NZ330041A/xx unknown
- 1998-03-26 DE DE69824332T patent/DE69824332T2/de not_active Expired - Fee Related
- 1998-03-26 PT PT98400711T patent/PT867436E/pt unknown
- 1998-03-26 EP EP98400711A patent/EP0867436B1/fr not_active Expired - Lifetime
- 1998-03-26 DK DK98400711T patent/DK0867436T3/da active
- 1998-03-26 ES ES98400711T patent/ES2223110T3/es not_active Expired - Lifetime
- 1998-03-27 BR BR9803295A patent/BR9803295A/pt not_active Application Discontinuation
- 1998-03-27 JP JP10081710A patent/JPH10279578A/ja active Pending
- 1998-03-27 US US09/049,233 patent/US5965575A/en not_active Expired - Fee Related
- 1998-03-27 AU AU59677/98A patent/AU731018B2/en not_active Ceased
- 1998-03-27 ZA ZA982607A patent/ZA982607B/xx unknown
- 1998-03-27 NO NO19981415A patent/NO314628B1/no unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003503492A (ja) * | 1999-06-30 | 2003-01-28 | ブリストルーマイヤーズ スクイブ カンパニー | メラトニン作用剤としての複素環式アミノピロリジン誘導体 |
| JP4767463B2 (ja) * | 1999-06-30 | 2011-09-07 | ブリストル−マイヤーズ スクイブ カンパニー | メラトニン作用剤としての複素環式アミノピロリジン誘導体 |
| WO2005005406A1 (ja) * | 2003-07-14 | 2005-01-20 | Ube Industries, Ltd. | 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 |
| JPWO2005005406A1 (ja) * | 2003-07-14 | 2007-09-20 | 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 |
| US7365215B2 (en) | 2003-07-14 | 2008-04-29 | Ube Industries, Ltd. | Process for preparing 4-aminotetrahydropyran compound and an acid salt thereof, synthetic intermediate thereof and process for preparing the same |
| 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 |
| JP2006290890A (ja) * | 2005-04-08 | 2006-10-26 | Lab Servier | ピペラジン化合物、その製造方法およびそれを含有する医薬組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69824332T2 (de) | 2005-06-16 |
| ES2223110T3 (es) | 2005-02-16 |
| NO981415D0 (no) | 1998-03-27 |
| AU5967798A (en) | 1998-10-01 |
| CA2232116C (fr) | 2003-09-16 |
| FR2761358A1 (fr) | 1998-10-02 |
| CA2232116A1 (fr) | 1998-09-27 |
| PL194118B1 (pl) | 2007-04-30 |
| US5965575A (en) | 1999-10-12 |
| AU731018B2 (en) | 2001-03-22 |
| DK0867436T3 (da) | 2004-10-04 |
| NZ330041A (en) | 1999-01-28 |
| BR9803295A (pt) | 2000-03-21 |
| PL325575A1 (en) | 1998-09-28 |
| CN1090628C (zh) | 2002-09-11 |
| ZA982607B (en) | 1998-09-30 |
| CN1197072A (zh) | 1998-10-28 |
| FR2761358B1 (fr) | 1999-05-07 |
| PT867436E (pt) | 2004-09-30 |
| HK1014954A1 (en) | 1999-10-08 |
| ATE268767T1 (de) | 2004-06-15 |
| NO981415L (no) | 1998-09-28 |
| EP0867436A1 (fr) | 1998-09-30 |
| EP0867436B1 (fr) | 2004-06-09 |
| DE69824332D1 (de) | 2004-07-15 |
| NO314628B1 (no) | 2003-04-22 |
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