NO322666B1 - Substituerte fenyl-piperazinderivater, farmasoytiske sammensetninger inneholdende disse og deres anvendelse - Google Patents
Substituerte fenyl-piperazinderivater, farmasoytiske sammensetninger inneholdende disse og deres anvendelse Download PDFInfo
- Publication number
- NO322666B1 NO322666B1 NO20023146A NO20023146A NO322666B1 NO 322666 B1 NO322666 B1 NO 322666B1 NO 20023146 A NO20023146 A NO 20023146A NO 20023146 A NO20023146 A NO 20023146A NO 322666 B1 NO322666 B1 NO 322666B1
- Authority
- NO
- Norway
- Prior art keywords
- piperazine
- indol
- propyl
- phenyl
- yloxy
- Prior art date
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- 239000008194 pharmaceutical composition Chemical class 0.000 title claims description 4
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 57
- -1 1-homopiperidinyl Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 230000027455 binding Effects 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- JCXYIZHUALZKGZ-UHFFFAOYSA-N 3-[3-[4-[2-(2,3-dihydro-1,4-benzodioxin-5-yloxy)phenyl]piperazin-1-yl]propyl]-5-fluoro-1h-indole Chemical compound O1CCOC2=C1C=CC=C2OC1=CC=CC=C1N(CC1)CCN1CCCC1=CNC2=CC=C(F)C=C21 JCXYIZHUALZKGZ-UHFFFAOYSA-N 0.000 claims description 6
- 208000012902 Nervous system disease Diseases 0.000 claims description 6
- 208000025966 Neurological disease Diseases 0.000 claims description 6
- YULASTKKEXFGFD-UHFFFAOYSA-N 5-fluoro-3-[3-[4-[2-(2-methoxyphenoxy)phenyl]piperazin-1-yl]propyl]-1h-indole Chemical compound COC1=CC=CC=C1OC1=CC=CC=C1N1CCN(CCCC=2C3=CC(F)=CC=C3NC=2)CC1 YULASTKKEXFGFD-UHFFFAOYSA-N 0.000 claims description 5
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- OWEYIAFRYKPGTI-UHFFFAOYSA-N 3-[2-[4-[2-(1,3-benzodioxol-5-yloxy)phenyl]piperazin-1-yl]ethyl]-6-chloro-1h-indole Chemical compound C1=C2OCOC2=CC(OC2=CC=CC=C2N2CCN(CC2)CCC=2C3=CC=C(C=C3NC=2)Cl)=C1 OWEYIAFRYKPGTI-UHFFFAOYSA-N 0.000 claims description 4
- JJWGGTBCCAPKEC-UHFFFAOYSA-N 3-[2-[4-[2-(6-chloro-1h-indol-3-yl)ethyl]piperazin-1-yl]phenoxy]-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC(OC=2C(=CC=CC=2)N2CCN(CCC=3C4=CC=C(Cl)C=C4NC=3)CC2)=C1 JJWGGTBCCAPKEC-UHFFFAOYSA-N 0.000 claims description 4
- XHYDHLYHMNFUCR-UHFFFAOYSA-N 3-[2-[4-[3-(5-fluoro-1h-indol-3-yl)propyl]piperazin-1-yl]phenoxy]-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC(OC=2C(=CC=CC=2)N2CCN(CCCC=3C4=CC(F)=CC=C4NC=3)CC2)=C1 XHYDHLYHMNFUCR-UHFFFAOYSA-N 0.000 claims description 4
- XKYRGHFKHNICJW-UHFFFAOYSA-N 3-[3-[4-[2-(1,3-benzodioxol-5-yloxy)phenyl]piperazin-1-yl]propyl]-5-chloro-1h-indole Chemical compound C1=C2OCOC2=CC(OC2=CC=CC=C2N2CCN(CC2)CCCC2=CNC3=CC=C(C=C32)Cl)=C1 XKYRGHFKHNICJW-UHFFFAOYSA-N 0.000 claims description 4
- FSEDYOZYCMHMQU-UHFFFAOYSA-N 3-[3-[4-[2-(1,3-benzodioxol-5-yloxy)phenyl]piperazin-1-yl]propyl]-5-fluoro-1h-indole Chemical compound C1=C2OCOC2=CC(OC2=CC=CC=C2N2CCN(CC2)CCCC2=CNC3=CC=C(C=C32)F)=C1 FSEDYOZYCMHMQU-UHFFFAOYSA-N 0.000 claims description 4
- VDUCKTWNZRHCIM-UHFFFAOYSA-N 3-[3-[4-[2-(1,3-benzodioxol-5-yloxy)phenyl]piperazin-1-yl]propyl]-5-methyl-1h-indole Chemical compound C1=C2OCOC2=CC(OC2=CC=CC=C2N2CCN(CC2)CCCC2=CNC3=CC=C(C=C32)C)=C1 VDUCKTWNZRHCIM-UHFFFAOYSA-N 0.000 claims description 4
- XEPRNSDBSCSQII-UHFFFAOYSA-N 3-[3-[4-[2-(1,3-benzodioxol-5-yloxy)phenyl]piperazin-1-yl]propyl]-7-bromo-1h-indole Chemical compound C1=C2OCOC2=CC(OC2=CC=CC=C2N2CCN(CC2)CCCC=2C=3C=CC=C(C=3NC=2)Br)=C1 XEPRNSDBSCSQII-UHFFFAOYSA-N 0.000 claims description 4
- YWFVVSIGTZAXMZ-UHFFFAOYSA-N 3-[3-[4-[2-(2,3-dihydro-1,4-benzodioxin-5-yloxy)phenyl]piperazin-1-yl]propyl]-5-methyl-1h-indole Chemical compound O1CCOC2=C1C=CC=C2OC1=CC=CC=C1N(CC1)CCN1CCCC1=CNC2=CC=C(C)C=C21 YWFVVSIGTZAXMZ-UHFFFAOYSA-N 0.000 claims description 4
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- GWXJVSCULKGPCF-UHFFFAOYSA-N n,n-diethyl-3-[2-[4-[3-(5-fluoro-1h-indol-3-yl)propyl]piperazin-1-yl]phenoxy]aniline Chemical compound CCN(CC)C1=CC=CC(OC=2C(=CC=CC=2)N2CCN(CCCC=3C4=CC(F)=CC=C4NC=3)CC2)=C1 GWXJVSCULKGPCF-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
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Classifications
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- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
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- 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
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- A—HUMAN NECESSITIES
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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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- A61P25/22—Anxiolytics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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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
- 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
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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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- 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
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA199901885 | 1999-12-30 | ||
| PCT/DK2000/000721 WO2001049678A1 (fr) | 1999-12-30 | 2000-12-20 | Derives phenyl-piperazine substitues, leur preparation et utilisation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20023146D0 NO20023146D0 (no) | 2002-06-28 |
| NO20023146L NO20023146L (no) | 2002-06-28 |
| NO322666B1 true NO322666B1 (no) | 2006-11-13 |
Family
ID=8108803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20023146A NO322666B1 (no) | 1999-12-30 | 2002-06-28 | Substituerte fenyl-piperazinderivater, farmasoytiske sammensetninger inneholdende disse og deres anvendelse |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US6699864B2 (fr) |
| EP (1) | EP1246816B1 (fr) |
| JP (1) | JP2003519224A (fr) |
| KR (1) | KR100790916B1 (fr) |
| CN (1) | CN1230432C (fr) |
| AR (1) | AR029428A1 (fr) |
| AT (1) | ATE261959T1 (fr) |
| AU (1) | AU2152101A (fr) |
| BG (1) | BG65262B1 (fr) |
| BR (1) | BR0016952A (fr) |
| CA (1) | CA2395705C (fr) |
| CZ (1) | CZ20022319A3 (fr) |
| DE (1) | DE60009155T2 (fr) |
| EA (1) | EA006071B1 (fr) |
| ES (1) | ES2213634T3 (fr) |
| HU (1) | HUP0203722A3 (fr) |
| IL (2) | IL150241A0 (fr) |
| IS (1) | IS2174B (fr) |
| MX (1) | MXPA02006223A (fr) |
| NO (1) | NO322666B1 (fr) |
| NZ (1) | NZ519647A (fr) |
| PL (1) | PL199351B1 (fr) |
| PT (1) | PT1246816E (fr) |
| SK (1) | SK9442002A3 (fr) |
| TR (2) | TR200400645T4 (fr) |
| UA (1) | UA72948C2 (fr) |
| WO (1) | WO2001049678A1 (fr) |
| ZA (1) | ZA200204814B (fr) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA81749C2 (uk) | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
| DE10259244A1 (de) * | 2002-12-17 | 2004-07-01 | Merck Patent Gmbh | N-(Indolethyl-)cycloamin-Verbindungen |
| UA81300C2 (en) * | 2003-04-04 | 2007-12-25 | Lundbeck & Co As H | Derivates of 4-(2-fenilsulfanilfenil)-1,2,3,6-tetrahydropiridin as retarding agents of serotonin recapture |
| AU2004226838B8 (en) | 2003-04-04 | 2009-06-11 | H. Lundbeck A/S | 4-(2-phenylsulfanyl-phenyl)-piperidine derivatives as serotonin reuptake inhibitors |
| MXPA06007172A (es) | 2003-12-23 | 2006-08-23 | Lundbeck & Co As H | Derivados de 2-(1h-indolilsulfanil)-bencilamina como ssri. |
| SE0400441D0 (sv) | 2004-02-25 | 2004-02-25 | Active Biotech Ab | Novel Benzofurans and Indols |
| AR052308A1 (es) | 2004-07-16 | 2007-03-14 | Lundbeck & Co As H | Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto |
| AR054393A1 (es) | 2005-06-17 | 2007-06-20 | Lundbeck & Co As H | Derivados de benzo(b)furano y benzo(b)tiofeno, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por la inhibicion de la reabsorcion de neurotransmisores de amina biogenicos. |
| US7629473B2 (en) | 2005-06-17 | 2009-12-08 | H. Lundbeck A/S | 2-(1H-indolylsulfanyl)-aryl amine derivatives |
| EP2044043B2 (fr) | 2006-06-16 | 2021-03-03 | H. Lundbeck A/S | 1-[2-(2, 4-dimethylphenylsulfanyl)-phenyl]piperazine hydrobromide comme compose presentant une activite sur la serotonine, 5-ht3 et 5-ht1a pour le traitement du deficit cognitif |
| AU2008310883A1 (en) * | 2007-10-09 | 2009-04-16 | Hamann, Mark T | Method to use compositions having antidepressant anxiolytic and other neurological activity and compositions of matter |
| CA2718138A1 (fr) * | 2008-03-14 | 2009-09-17 | Timo Heinrich | Composes d'azaindole pour le traitement de troubles du systeme nerveux central |
| CN105283442B (zh) * | 2013-04-04 | 2018-04-13 | 斯洛文尼亚莱柯制药股份有限公司 | 用于合成1‑(2‑((2,4‑二甲基苯基)硫代)苯基)哌嗪的方法 |
| WO2015169180A1 (fr) * | 2014-05-04 | 2015-11-12 | Sunshine Lake Pharma Co., Ltd. | Composés pipéraziniques substitués, procédés et utilisation associés |
| CN105085491B (zh) * | 2014-05-05 | 2019-06-25 | 广东东阳光药业有限公司 | 取代的吲哚化合物及其使用方法和用途 |
| US10316025B2 (en) | 2015-06-03 | 2019-06-11 | Sunshine Lake Pharma Co., Ltd. | Substituted piperazine compounds and methods of use and use thereof |
| WO2017012579A1 (fr) * | 2015-07-23 | 2017-01-26 | 广东东阳光药业有限公司 | Composés d'indole substitués, méthodes d'utilisation et utilisations de ceux-ci |
| US11285153B2 (en) | 2017-09-29 | 2022-03-29 | Sunshine Lake Pharma Co., Ltd. | Substituted pyrimidine piperazine compound and use thereof |
| CN111518012A (zh) * | 2020-05-27 | 2020-08-11 | 中国药科大学 | 含苯硫醚结构的化合物或其药学上可接受的盐、制备方法和用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2138865A1 (de) * | 1970-08-15 | 1973-02-22 | Sumitomo Chemical Co | 3-indolylpiperazine, verfahren zu ihrer herstellung und arzneimittel |
| GB8830312D0 (en) * | 1988-12-28 | 1989-02-22 | Lundbeck & Co As H | Heterocyclic compounds |
| WO1994024105A1 (fr) * | 1993-04-15 | 1994-10-27 | Merck Sharp & Dohme Limited | Derives d'indole utiles comme antagonistes de la dopamine d4 |
| FR2712591B1 (fr) | 1993-11-19 | 1996-02-09 | Pf Medicament | Nouvelles arylpipérazines dérivées d'indole, leur préparation et leur utilisation thérapeutique. |
| WO1997019039A1 (fr) | 1995-11-17 | 1997-05-29 | Novartis Ag | Synthese en phase solide de composes heterocycliques et d'une banque combinatoire de composes |
| USH2007H1 (en) * | 1996-01-19 | 2001-12-04 | Fmc Corporation | Insecticidal N-heterocyclylalkyl-or N-[(polycyclyl)alkyl]-N′substituted piperazines |
| ES2128266B1 (es) * | 1997-07-08 | 2000-01-16 | Vita Invest Sa | Compuestos derivados de tiofeno y benzotiofeno y utilizacion y composicion correspondientes. |
| WO2000077519A1 (fr) | 1999-06-15 | 2000-12-21 | Aventis Pharmaceuticals Products Inc. | Synthese en phase solide de derives de diazacycloalkylcarboxy n,n-disubstitues |
| EP1246819A1 (fr) * | 1999-12-30 | 2002-10-09 | H. Lundbeck A/S | Procede de preparation de derives de benzene substitue |
-
2000
- 2000-12-20 KR KR1020027008608A patent/KR100790916B1/ko not_active IP Right Cessation
- 2000-12-20 CN CNB008192057A patent/CN1230432C/zh not_active Expired - Fee Related
- 2000-12-20 UA UA2002065260A patent/UA72948C2/uk unknown
- 2000-12-20 SK SK944-2002A patent/SK9442002A3/sk unknown
- 2000-12-20 BR BR0016952-8A patent/BR0016952A/pt not_active Application Discontinuation
- 2000-12-20 CA CA002395705A patent/CA2395705C/fr not_active Expired - Fee Related
- 2000-12-20 PT PT00984924T patent/PT1246816E/pt unknown
- 2000-12-20 AT AT00984924T patent/ATE261959T1/de not_active IP Right Cessation
- 2000-12-20 PL PL355539A patent/PL199351B1/pl not_active IP Right Cessation
- 2000-12-20 TR TR2004/00645T patent/TR200400645T4/xx unknown
- 2000-12-20 EP EP00984924A patent/EP1246816B1/fr not_active Expired - Lifetime
- 2000-12-20 AU AU21521/01A patent/AU2152101A/en not_active Abandoned
- 2000-12-20 WO PCT/DK2000/000721 patent/WO2001049678A1/fr active IP Right Grant
- 2000-12-20 JP JP2001550218A patent/JP2003519224A/ja active Pending
- 2000-12-20 DE DE60009155T patent/DE60009155T2/de not_active Expired - Fee Related
- 2000-12-20 TR TR2002/01683T patent/TR200201683T2/xx unknown
- 2000-12-20 ES ES00984924T patent/ES2213634T3/es not_active Expired - Lifetime
- 2000-12-20 CZ CZ20022319A patent/CZ20022319A3/cs unknown
- 2000-12-20 HU HU0203722A patent/HUP0203722A3/hu unknown
- 2000-12-20 NZ NZ519647A patent/NZ519647A/en unknown
- 2000-12-20 MX MXPA02006223A patent/MXPA02006223A/es active IP Right Grant
- 2000-12-20 EA EA200200732A patent/EA006071B1/ru not_active IP Right Cessation
- 2000-12-20 IL IL15024100A patent/IL150241A0/xx unknown
- 2000-12-28 AR ARP000106987A patent/AR029428A1/es unknown
-
2002
- 2002-06-13 IS IS6420A patent/IS2174B/is unknown
- 2002-06-14 ZA ZA200204814A patent/ZA200204814B/xx unknown
- 2002-06-16 IL IL150241A patent/IL150241A/en not_active IP Right Cessation
- 2002-06-20 US US10/177,261 patent/US6699864B2/en not_active Expired - Fee Related
- 2002-06-28 NO NO20023146A patent/NO322666B1/no not_active IP Right Cessation
- 2002-07-17 BG BG106930A patent/BG65262B1/bg unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |