AU731018B2 - New N-aryl piperidine compounds, a process for their preparation and pharmaceutical compositions containing them - Google Patents
New N-aryl piperidine compounds, a process for their preparation and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- AU731018B2 AU731018B2 AU59677/98A AU5967798A AU731018B2 AU 731018 B2 AU731018 B2 AU 731018B2 AU 59677/98 A AU59677/98 A AU 59677/98A AU 5967798 A AU5967798 A AU 5967798A AU 731018 B2 AU731018 B2 AU 731018B2
- Authority
- AU
- Australia
- Prior art keywords
- dihydro
- benzodioxin
- amine
- piperid
- fumarate
- 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.)
- Ceased
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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
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- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- OZUPVQXYPSHGFY-UHFFFAOYSA-N methyl 2-(8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl)acetate Chemical compound C12=CC(OC)=C(OC)C=C2CCN2C1=CC(CC(=O)OC)=C2 OZUPVQXYPSHGFY-UHFFFAOYSA-N 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- COGGGWRHZQTITF-UHFFFAOYSA-N n-(oxan-4-ylidene)hydroxylamine Chemical compound ON=C1CCOCC1 COGGGWRHZQTITF-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
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- 239000002858 neurotransmitter agent Substances 0.000 description 1
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- 235000020824 obesity Nutrition 0.000 description 1
- KWZSCXIYGVEHOB-UHFFFAOYSA-N oxan-4-amine;hydrochloride Chemical compound [Cl-].[NH3+]C1CCOCC1 KWZSCXIYGVEHOB-UHFFFAOYSA-N 0.000 description 1
- JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 229960001412 pentobarbital Drugs 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
- 239000008363 phosphate buffer Substances 0.000 description 1
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical group NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 1
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 238000012552 review Methods 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 238000010972 statistical evaluation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
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- 230000002889 sympathetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000012795 verification Methods 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)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- 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 |
|---|---|
| AU5967798A AU5967798A (en) | 1998-10-01 |
| AU731018B2 true AU731018B2 (en) | 2001-03-22 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU59677/98A Ceased AU731018B2 (en) | 1997-03-27 | 1998-03-27 | New N-aryl piperidine compounds, a process for their preparation and pharmaceutical compositions containing them |
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 |
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| 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 |
| EP1189900B1 (en) * | 1999-06-30 | 2004-01-14 | Bristol-Myers Squibb Company | Heterocyclic aminopyrrolidine derivatives as melatonergic agents |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
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| 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
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 |
| 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 |
| JPH10279578A (ja) | 1998-10-20 |
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