NO317516B1 - Nye indan-l-ol forbindelser, en fremgangsmate for a behandle dem og farmasoytiske forbindelser inneholdende dem - Google Patents
Nye indan-l-ol forbindelser, en fremgangsmate for a behandle dem og farmasoytiske forbindelser inneholdende dem Download PDFInfo
- Publication number
- NO317516B1 NO317516B1 NO19994041A NO994041A NO317516B1 NO 317516 B1 NO317516 B1 NO 317516B1 NO 19994041 A NO19994041 A NO 19994041A NO 994041 A NO994041 A NO 994041A NO 317516 B1 NO317516 B1 NO 317516B1
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- formula
- dihydro
- amino
- indanol
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims description 13
- YIAPLDFPUUJILH-UHFFFAOYSA-N indan-1-ol Chemical class C1=CC=C2C(O)CCC2=C1 YIAPLDFPUUJILH-UHFFFAOYSA-N 0.000 title description 2
- 239000002253 acid Substances 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims abstract description 3
- 229940079593 drug Drugs 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 230000002295 serotoninergic effect Effects 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 230000002490 cerebral effect Effects 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 206010002388 Angina unstable Diseases 0.000 claims description 3
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- 230000036506 anxiety Effects 0.000 claims description 3
- 231100000869 headache Toxicity 0.000 claims description 3
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 3
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 claims description 3
- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- OXARMVQQPRHXEI-WIYYLYMNSA-N (1r,2r)-2-[[1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperidin-4-yl]amino]-2,3-dihydro-1h-inden-1-ol Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1N[C@H]1[C@H](O)C2=CC=CC=C2C1 OXARMVQQPRHXEI-WIYYLYMNSA-N 0.000 claims description 2
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- 208000022531 anorexia Diseases 0.000 claims description 2
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical group C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000969 carrier Substances 0.000 claims description 2
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- 230000004064 dysfunction Effects 0.000 claims description 2
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- 231100000252 nontoxic Toxicity 0.000 claims description 2
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- 238000000746 purification Methods 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- FRUBNNQTJYFFHM-IFMALSPDSA-N (1r,2r)-2-[[1-(3,4-dihydro-2h-chromen-8-yl)piperidin-4-yl]amino]-5-fluoro-2,3-dihydro-1h-inden-1-ol Chemical compound C1CCOC2=C1C=CC=C2N(CC1)CCC1N[C@H]1[C@H](O)C2=CC=C(F)C=C2C1 FRUBNNQTJYFFHM-IFMALSPDSA-N 0.000 claims 1
- QIBUNEWDULRYRV-IFMALSPDSA-N (1r,2r)-2-[[1-(3,4-dihydro-2h-chromen-8-yl)piperidin-4-yl]amino]-6-fluoro-2,3-dihydro-1h-inden-1-ol Chemical compound C1CCOC2=C1C=CC=C2N(CC1)CCC1N[C@H]1[C@H](O)C2=CC(F)=CC=C2C1 QIBUNEWDULRYRV-IFMALSPDSA-N 0.000 claims 1
- QIBUNEWDULRYRV-RBBKRZOGSA-N (1r,2s)-2-[[1-(3,4-dihydro-2h-chromen-8-yl)piperidin-4-yl]amino]-6-fluoro-2,3-dihydro-1h-inden-1-ol Chemical compound C1CCOC2=C1C=CC=C2N(CC1)CCC1N[C@@H]1[C@H](O)C2=CC(F)=CC=C2C1 QIBUNEWDULRYRV-RBBKRZOGSA-N 0.000 claims 1
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- 125000000217 alkyl group Chemical group 0.000 abstract 3
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- 238000002474 experimental method Methods 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
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- 239000006071 cream Substances 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000005153 frontal cortex Anatomy 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000002197 limbic effect Effects 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- -1 lithium aluminum hydride Chemical compound 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 230000001272 neurogenic effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 229960001779 pargyline Drugs 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-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
- 238000005406 washing 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
- A61P25/06—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
- A61P25/22—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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9810601A FR2782515B1 (fr) | 1998-08-21 | 1998-08-21 | NOUVEAUX DERIVES DE L'INDANE-1-Ol, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO994041D0 NO994041D0 (no) | 1999-08-20 |
| NO994041L NO994041L (no) | 2000-02-22 |
| NO317516B1 true NO317516B1 (no) | 2004-11-08 |
Family
ID=9529811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19994041A NO317516B1 (no) | 1998-08-21 | 1999-08-20 | Nye indan-l-ol forbindelser, en fremgangsmate for a behandle dem og farmasoytiske forbindelser inneholdende dem |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6153625A (hu) |
| EP (1) | EP0982305B1 (hu) |
| JP (1) | JP2000072748A (hu) |
| CN (1) | CN1128144C (hu) |
| AT (1) | ATE214064T1 (hu) |
| AU (1) | AU747494B2 (hu) |
| BR (1) | BR9903867A (hu) |
| CA (1) | CA2280596A1 (hu) |
| DE (1) | DE69900961T2 (hu) |
| DK (1) | DK0982305T3 (hu) |
| ES (1) | ES2172294T3 (hu) |
| FR (1) | FR2782515B1 (hu) |
| HK (1) | HK1026212A1 (hu) |
| HU (1) | HUP9902784A3 (hu) |
| NO (1) | NO317516B1 (hu) |
| NZ (1) | NZ337362A (hu) |
| PL (1) | PL194852B1 (hu) |
| PT (1) | PT982305E (hu) |
| ZA (1) | ZA995321B (hu) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0103647D0 (sv) * | 2001-11-01 | 2001-11-01 | Astrazeneca Ab | Therapeutic chromone compounds |
| EP1353914A2 (en) * | 2001-01-16 | 2003-10-22 | AstraZeneca AB | Therapeutic chromone 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 |
| CN100509794C (zh) * | 2001-01-16 | 2009-07-08 | 阿斯特拉曾尼卡有限公司 | 治疗性杂环化合物 |
| DE10142661B4 (de) * | 2001-08-31 | 2004-06-09 | Aventis Pharma Deutschland Gmbh | Mehrfach substituierte Indan-1-ol-Systeme und ihre Verwendung als Arzneimittel |
| DE10142667B4 (de) * | 2001-08-31 | 2004-06-09 | Aventis Pharma Deutschland Gmbh | C2-substituierte Indan-1-ole und ihre Derivate und ihre Verwendung als Arzneimittel |
| DE10142662B4 (de) * | 2001-08-31 | 2004-07-08 | Aventis Pharma Deutschland Gmbh | Derivate von C2-substituierten Indan-1-ol-Systemen und ihre Verwendung als Arzneimittel |
| UY29892A1 (es) * | 2005-11-04 | 2007-06-29 | Astrazeneca Ab | Nuevos derivados de cromano, composiciones farmaceuticas conteniendolos, procesos de preparacion y aplicaciones |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2681325B1 (fr) * | 1991-09-16 | 1993-12-17 | Fabre Medicament Pierre | Derives de l'aminomethyl-4 piperidine, leur preparation et leur application en therapeutique. |
| GB9318431D0 (en) * | 1993-09-06 | 1993-10-20 | Boots Co Plc | Therapeutic agents |
| FR2761358B1 (fr) * | 1997-03-27 | 1999-05-07 | Adir | Nouveaux composes de n-aryl piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
1998
- 1998-08-21 FR FR9810601A patent/FR2782515B1/fr not_active Expired - Fee Related
-
1999
- 1999-08-13 US US09/374,161 patent/US6153625A/en not_active Expired - Fee Related
- 1999-08-19 JP JP11232097A patent/JP2000072748A/ja active Pending
- 1999-08-19 HU HU9902784A patent/HUP9902784A3/hu unknown
- 1999-08-20 BR BR9903867-6A patent/BR9903867A/pt not_active Application Discontinuation
- 1999-08-20 EP EP99402092A patent/EP0982305B1/fr not_active Expired - Lifetime
- 1999-08-20 ES ES99402092T patent/ES2172294T3/es not_active Expired - Lifetime
- 1999-08-20 AT AT99402092T patent/ATE214064T1/de not_active IP Right Cessation
- 1999-08-20 NO NO19994041A patent/NO317516B1/no unknown
- 1999-08-20 ZA ZA9905321A patent/ZA995321B/xx unknown
- 1999-08-20 AU AU44637/99A patent/AU747494B2/en not_active Ceased
- 1999-08-20 NZ NZ337362A patent/NZ337362A/xx unknown
- 1999-08-20 CN CN99119425A patent/CN1128144C/zh not_active Expired - Fee Related
- 1999-08-20 DE DE69900961T patent/DE69900961T2/de not_active Expired - Fee Related
- 1999-08-20 CA CA002280596A patent/CA2280596A1/fr not_active Abandoned
- 1999-08-20 PT PT99402092T patent/PT982305E/pt unknown
- 1999-08-20 DK DK99402092T patent/DK0982305T3/da active
- 1999-08-20 PL PL335012A patent/PL194852B1/pl not_active IP Right Cessation
-
2000
- 2000-09-04 HK HK00105538A patent/HK1026212A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9902784A2 (hu) | 2000-12-28 |
| PL335012A1 (en) | 2000-02-28 |
| FR2782515B1 (fr) | 2000-09-22 |
| HU9902784D0 (en) | 1999-10-28 |
| DE69900961D1 (de) | 2002-04-11 |
| PL194852B1 (pl) | 2007-07-31 |
| NO994041D0 (no) | 1999-08-20 |
| CN1128144C (zh) | 2003-11-19 |
| ES2172294T3 (es) | 2002-09-16 |
| ATE214064T1 (de) | 2002-03-15 |
| EP0982305B1 (fr) | 2002-03-06 |
| AU747494B2 (en) | 2002-05-16 |
| US6153625A (en) | 2000-11-28 |
| CN1250051A (zh) | 2000-04-12 |
| FR2782515A1 (fr) | 2000-02-25 |
| PT982305E (pt) | 2002-07-31 |
| BR9903867A (pt) | 2000-09-05 |
| HUP9902784A3 (en) | 2001-03-28 |
| HK1026212A1 (en) | 2000-12-08 |
| NO994041L (no) | 2000-02-22 |
| JP2000072748A (ja) | 2000-03-07 |
| ZA995321B (en) | 2000-02-22 |
| EP0982305A1 (fr) | 2000-03-01 |
| DE69900961T2 (de) | 2002-11-07 |
| DK0982305T3 (da) | 2002-06-24 |
| CA2280596A1 (fr) | 2000-02-21 |
| AU4463799A (en) | 2000-03-09 |
| NZ337362A (en) | 2000-04-28 |
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