ZA200201486B - N-(Indolecarbonyl-)piperazine derivatives als 5-HT2A-receptor ligands. - Google Patents
N-(Indolecarbonyl-)piperazine derivatives als 5-HT2A-receptor ligands. Download PDFInfo
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- ZA200201486B ZA200201486B ZA200201486A ZA200201486A ZA200201486B ZA 200201486 B ZA200201486 B ZA 200201486B ZA 200201486 A ZA200201486 A ZA 200201486A ZA 200201486 A ZA200201486 A ZA 200201486A ZA 200201486 B ZA200201486 B ZA 200201486B
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- 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 title claims 2
- 108010072564 5-HT2A Serotonin Receptor Proteins 0.000 title claims 2
- 150000004885 piperazines Chemical class 0.000 title description 3
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 3
- 239000003446 ligand Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 81
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- 238000011282 treatment Methods 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
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- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
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- 239000012047 saturated solution Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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- 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
- C07D409/12—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 linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
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- 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
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A61P25/00—Drugs for disorders of the nervous system
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- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- 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
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- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
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- A—HUMAN NECESSITIES
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- 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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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (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)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Psychology (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Obesity (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19934433A DE19934433A1 (de) | 1999-07-22 | 1999-07-22 | N-(Indolcarbonyl-)piperazinderivate |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200201486B true ZA200201486B (en) | 2003-07-30 |
Family
ID=7915702
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200201486A ZA200201486B (en) | 1999-07-22 | 2002-02-21 | N-(Indolecarbonyl-)piperazine derivatives als 5-HT2A-receptor ligands. |
Country Status (26)
Country | Link |
---|---|
US (2) | US6838461B1 (pl) |
EP (1) | EP1198453B9 (pl) |
JP (2) | JP5242871B2 (pl) |
KR (1) | KR100779207B1 (pl) |
CN (1) | CN1229345C (pl) |
AR (1) | AR024819A1 (pl) |
AT (1) | ATE236877T1 (pl) |
AU (1) | AU770411B2 (pl) |
BR (1) | BR0012607A (pl) |
CA (1) | CA2383779C (pl) |
CZ (1) | CZ300510B6 (pl) |
DE (2) | DE19934433A1 (pl) |
DK (1) | DK1198453T5 (pl) |
ES (1) | ES2192535T3 (pl) |
HK (1) | HK1048636B (pl) |
HU (1) | HUP0201988A3 (pl) |
MX (1) | MXPA02000730A (pl) |
MY (1) | MY122531A (pl) |
NO (1) | NO322154B1 (pl) |
PL (1) | PL201893B1 (pl) |
PT (1) | PT1198453E (pl) |
RU (1) | RU2251548C2 (pl) |
SK (1) | SK286066B6 (pl) |
UA (1) | UA73518C2 (pl) |
WO (1) | WO2001007435A2 (pl) |
ZA (1) | ZA200201486B (pl) |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6589954B1 (en) * | 1998-05-22 | 2003-07-08 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
IL146309A (en) | 1999-05-21 | 2008-03-20 | Scios Inc | Derivatives of the indole type and pharmaceutical preparations containing them as inhibitors of kinase p38 |
DE19934433A1 (de) * | 1999-07-22 | 2001-01-25 | Merck Patent Gmbh | N-(Indolcarbonyl-)piperazinderivate |
DE19934432A1 (de) * | 1999-07-22 | 2001-02-01 | Merck Patent Gmbh | Indolderivate |
US8465468B1 (en) | 2000-06-29 | 2013-06-18 | Becton, Dickinson And Company | Intradermal delivery of substances |
US20020095134A1 (en) * | 1999-10-14 | 2002-07-18 | Pettis Ronald J. | Method for altering drug pharmacokinetics based on medical delivery platform |
US20020156453A1 (en) * | 1999-10-14 | 2002-10-24 | Pettis Ronald J. | Method and device for reducing therapeutic dosage |
DE10102053A1 (de) * | 2001-01-17 | 2002-07-18 | Merck Patent Gmbh | Piperazinylcarbonylchinoline und -isochinoline |
WO2002102774A1 (en) | 2001-06-15 | 2002-12-27 | F. Hoffmann-La Roche Ag | 4-piperazinylindole derivatives with 5-ht6 receptor affinity |
WO2003002069A2 (en) * | 2001-06-29 | 2003-01-09 | Becton, Dickinson And Company | Intradermal delivery of vaccines and gene therapeutic agents via microcannula |
DE10157673A1 (de) * | 2001-11-24 | 2003-06-05 | Merck Patent Gmbh | Verwendung von N-(Indolcarbonyl-)piperazinderivaten |
GB0203811D0 (en) * | 2002-02-18 | 2002-04-03 | Glaxo Group Ltd | Compounds |
DE10212564B4 (de) * | 2002-03-12 | 2007-04-19 | Neurobiotec Gmbh | 1-Allyl-ergotalkaloid-Derivate und ihre Verwendung zur Prophylaxe und Therapie von Migräne |
DE10217006A1 (de) * | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
JP2005537054A (ja) * | 2002-08-30 | 2005-12-08 | ベクトン・ディキンソン・アンド・カンパニー | 免疫調節化合物の薬物動態を制御する方法 |
DE10246357A1 (de) * | 2002-10-04 | 2004-04-15 | Merck Patent Gmbh | Verwendung von 5-HT2Rezeptorantagonisten |
WO2005016401A2 (en) * | 2003-06-13 | 2005-02-24 | Becton Dickinson And Company | Improved intra-dermal delivery of biologically active agents |
WO2005023328A2 (en) * | 2003-08-26 | 2005-03-17 | Becton Dickinson And Company | Methods for intradermal delivery of therapeutics agents |
WO2005091922A2 (en) * | 2004-03-03 | 2005-10-06 | Becton, Dickinson And Company | Methods and devices for improving delivery of a substance to skin |
WO2005108378A2 (en) * | 2004-04-15 | 2005-11-17 | Samaritan Pharmaceuticals, Inc. | Use of (4-alkylpiperazinyl) (phenyl) methanones in the treatment of alzheimer’s disease |
US20050256182A1 (en) * | 2004-05-11 | 2005-11-17 | Sutter Diane E | Formulations of anti-pain agents and methods of using the same |
DE102004047517A1 (de) * | 2004-09-28 | 2006-03-30 | Merck Patent Gmbh | Neuartige Kristallform von (3-Cyan-1H-indol-7-yl)-[4-(4-fluorphenethyl)-piperazin-1-yl]-methanon, Hydrochlorid |
SI1831159T1 (sl) * | 2004-12-21 | 2010-04-30 | Hoffmann La Roche | Derivati tetralina in indana ter njune uporabe |
GT200600042A (es) * | 2005-02-10 | 2006-09-27 | Aventis Pharma Inc | Compuestos de bis arilo y heteroarilo sustituido como antagonistas selectivos de 5ht2a |
CA2652215A1 (en) * | 2006-05-05 | 2007-11-15 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Crystalline (3-cyano-1h-indol-7-yl)-[4-(4-fluorophenethyl)piperazin-1-yl]methanone phosphate |
US7514433B2 (en) * | 2006-08-03 | 2009-04-07 | Hoffmann-La Roche Inc. | 1H-indole-6-yl-piperazin-1-yl-methanone derivatives |
US8815852B2 (en) * | 2007-05-14 | 2014-08-26 | Sk Biopharmaceuticals Co., Ltd. | Carbamoyloxy arylalkan arylpiperazine analgesics |
EP2008656A1 (en) * | 2007-06-28 | 2008-12-31 | Bergen Teknologioverforing AS | Compositions for the treatment of hyperphenylalaninemia |
US9567327B2 (en) * | 2007-08-15 | 2017-02-14 | Arena Pharmaceuticals, Inc. | Imidazo[1,2-a]pyridine derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto |
KR101062376B1 (ko) | 2008-04-10 | 2011-09-06 | 한국화학연구원 | 신규 인돌 카르복실산 비스피리딜 카르복사마이드 유도체,이의 제조방법 및 이를 유효성분으로 함유하는 조성물 |
US9308323B2 (en) | 2011-11-15 | 2016-04-12 | Smiths Medical Asd, Inc. | Systems and methods for illuminated medical tubing detection and management indicating a characteristic of at least one infusion pump |
RU2549963C1 (ru) * | 2014-04-08 | 2015-05-10 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Дальневосточный государственный медицинский университет" Министерства здравоохранения Российской Федерации (ГБОУ ВПО "ДВГМУ" Минздрава России) | Способ прогнозирования развития критической печеночной недостаточности на основании сывороточного уровня селена |
GB2554371B (en) * | 2016-09-22 | 2019-10-09 | Resolute Energy Solutions Ltd | Well apparatus and associated methods |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NO301689B1 (no) | 1987-09-24 | 1997-12-01 | Jencap Research Ltd | Kontraseptivt preparat i form av en forpakning |
US5093341A (en) | 1987-12-17 | 1992-03-03 | Merrell Dow Pharmaceuticals Inc. | N-aralkyl piperidine derivatives useful as antithrombolytic agents |
US5032604A (en) * | 1989-12-08 | 1991-07-16 | Merck & Co., Inc. | Class III antiarrhythmic agents |
US5032598A (en) * | 1989-12-08 | 1991-07-16 | Merck & Co., Inc. | Nitrogens containing heterocyclic compounds as class III antiarrhythmic agents |
US5330986A (en) | 1992-11-24 | 1994-07-19 | Hoechst-Roussel Pharmaceuticals Inc. | Indole-7-carboxamide derivatives |
ZA954689B (en) | 1994-06-08 | 1996-01-29 | Lundbeck & Co As H | 4-Aryl-1-(indanmethyl dihydrobenzofuranmethyl or dihydrobenzothiophenemethyl) piperidines tetrahydropyridines or piperazines |
WO1998006715A1 (en) | 1996-08-09 | 1998-02-19 | Smithkline Beecham Corporation | Novel piperazine containing compounds |
GB9718712D0 (en) * | 1997-09-03 | 1997-11-12 | Merck Sharp & Dohme | Theraputic Agents |
DE19934432A1 (de) * | 1999-07-22 | 2001-02-01 | Merck Patent Gmbh | Indolderivate |
DE19934433A1 (de) * | 1999-07-22 | 2001-01-25 | Merck Patent Gmbh | N-(Indolcarbonyl-)piperazinderivate |
WO2005099240A1 (ja) * | 2004-04-07 | 2005-10-20 | Matsushita Electric Industrial Co., Ltd. | 情報交換支援装置、情報交換支援方法、及び情報交換支援プログラム |
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1999
- 1999-07-22 DE DE19934433A patent/DE19934433A1/de not_active Withdrawn
-
2000
- 2000-07-07 WO PCT/EP2000/006464 patent/WO2001007435A2/de active IP Right Grant
- 2000-07-07 UA UA2002021354A patent/UA73518C2/uk unknown
- 2000-07-07 US US10/031,367 patent/US6838461B1/en not_active Expired - Lifetime
- 2000-07-07 PL PL353446A patent/PL201893B1/pl not_active IP Right Cessation
- 2000-07-07 AT AT00949288T patent/ATE236877T1/de not_active IP Right Cessation
- 2000-07-07 BR BR0012607-1A patent/BR0012607A/pt active Search and Examination
- 2000-07-07 KR KR1020027000315A patent/KR100779207B1/ko not_active IP Right Cessation
- 2000-07-07 JP JP2001512519A patent/JP5242871B2/ja not_active Expired - Fee Related
- 2000-07-07 EP EP00949288A patent/EP1198453B9/de not_active Expired - Lifetime
- 2000-07-07 ES ES00949288T patent/ES2192535T3/es not_active Expired - Lifetime
- 2000-07-07 CN CNB00810719XA patent/CN1229345C/zh not_active Expired - Fee Related
- 2000-07-07 AU AU62704/00A patent/AU770411B2/en not_active Ceased
- 2000-07-07 RU RU2002103302/04A patent/RU2251548C2/ru not_active IP Right Cessation
- 2000-07-07 CA CA2383779A patent/CA2383779C/en not_active Expired - Fee Related
- 2000-07-07 DE DE50001729T patent/DE50001729D1/de not_active Expired - Lifetime
- 2000-07-07 CZ CZ20020068A patent/CZ300510B6/cs not_active IP Right Cessation
- 2000-07-07 DK DK00949288T patent/DK1198453T5/da active
- 2000-07-07 SK SK51-2002A patent/SK286066B6/sk not_active IP Right Cessation
- 2000-07-07 HU HU0201988A patent/HUP0201988A3/hu unknown
- 2000-07-07 MX MXPA02000730A patent/MXPA02000730A/es active IP Right Grant
- 2000-07-07 PT PT00949288T patent/PT1198453E/pt unknown
- 2000-07-20 MY MYPI20003320A patent/MY122531A/en unknown
- 2000-07-21 AR ARP000103775A patent/AR024819A1/es active IP Right Grant
-
2002
- 2002-01-21 NO NO20020307A patent/NO322154B1/no not_active IP Right Cessation
- 2002-02-21 ZA ZA200201486A patent/ZA200201486B/en unknown
-
2003
- 2003-02-04 HK HK03100811.4A patent/HK1048636B/zh not_active IP Right Cessation
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2004
- 2004-12-17 US US11/013,908 patent/US7084143B2/en not_active Expired - Fee Related
-
2011
- 2011-07-29 JP JP2011166851A patent/JP2012006940A/ja active Pending
Also Published As
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