NO329426B1 - 3-heteroaryl-3,5-dihydro-4-okso-4H-pyridazino[4,5-b]indol-1-acetamid-derivater, farmasoytiske preparater omfattende slike, fremgangsmater for fremstilling derav og syntese-mellomprodukter derav - Google Patents
3-heteroaryl-3,5-dihydro-4-okso-4H-pyridazino[4,5-b]indol-1-acetamid-derivater, farmasoytiske preparater omfattende slike, fremgangsmater for fremstilling derav og syntese-mellomprodukter derav Download PDFInfo
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- NO329426B1 NO329426B1 NO20044153A NO20044153A NO329426B1 NO 329426 B1 NO329426 B1 NO 329426B1 NO 20044153 A NO20044153 A NO 20044153A NO 20044153 A NO20044153 A NO 20044153A NO 329426 B1 NO329426 B1 NO 329426B1
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- Prior art keywords
- compound
- hydrogen atom
- alkyl group
- general formula
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- 238000002329 infrared spectrum Methods 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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- UTBCRHAMJFMIIR-UHFFFAOYSA-N methyl 3-chloro-3-oxopropanoate Chemical compound COC(=O)CC(Cl)=O UTBCRHAMJFMIIR-UHFFFAOYSA-N 0.000 description 1
- OIOQCOWQAQZWQH-UHFFFAOYSA-N methyl 6-chloro-3-(3-ethoxy-3-oxopropanoyl)-1-methylindole-2-carboxylate Chemical compound ClC1=CC=C2C(C(=O)CC(=O)OCC)=C(C(=O)OC)N(C)C2=C1 OIOQCOWQAQZWQH-UHFFFAOYSA-N 0.000 description 1
- JIIBSKHERZAHCH-UHFFFAOYSA-N methyl 6-fluoro-1h-indole-2-carboxylate Chemical compound C1=C(F)C=C2NC(C(=O)OC)=CC2=C1 JIIBSKHERZAHCH-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
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- 208000018389 neoplasm of cerebral hemisphere Diseases 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
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- 230000016273 neuron death Effects 0.000 description 1
- 230000006576 neuronal survival Effects 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
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- 239000003900 neurotrophic factor Substances 0.000 description 1
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 208000027232 peripheral nervous system disease Diseases 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical compound NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
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- 230000025053 regulation of cell proliferation Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 230000009424 thromboembolic effect Effects 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
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- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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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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- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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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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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
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- A61P37/02—Immunomodulators
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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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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (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)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0204158A FR2838124B1 (fr) | 2002-04-03 | 2002-04-03 | Derives de 3-heteroaryl-3,5-dihydro-4-oxo-4h-pyridazino [4,5-b]indole-1-acetamide, leur preparation et leur application en therapeutique |
PCT/FR2003/001027 WO2003082874A2 (fr) | 2002-04-03 | 2003-04-02 | DERIVES DE 3-HETEROARYL-3,5-DIHYDRO-4-OXO-4H-PYRIDAZINO[4,5-b]INDOLE-1-ACETAMIDE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
Publications (2)
Publication Number | Publication Date |
---|---|
NO20044153L NO20044153L (no) | 2004-12-27 |
NO329426B1 true NO329426B1 (no) | 2010-10-18 |
Family
ID=28052083
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20044153A NO329426B1 (no) | 2002-04-03 | 2004-09-30 | 3-heteroaryl-3,5-dihydro-4-okso-4H-pyridazino[4,5-b]indol-1-acetamid-derivater, farmasoytiske preparater omfattende slike, fremgangsmater for fremstilling derav og syntese-mellomprodukter derav |
Country Status (29)
Country | Link |
---|---|
US (4) | US7235554B2 (pt) |
EP (1) | EP1492792B1 (pt) |
JP (2) | JP4575670B2 (pt) |
KR (1) | KR100975999B1 (pt) |
CN (2) | CN100406459C (pt) |
AT (1) | ATE321763T1 (pt) |
AU (1) | AU2003240930B2 (pt) |
BR (1) | BR0309018A (pt) |
CA (1) | CA2481460C (pt) |
CY (1) | CY1104998T1 (pt) |
DE (1) | DE60304327T2 (pt) |
DK (1) | DK1492792T3 (pt) |
EA (1) | EA007219B1 (pt) |
ES (1) | ES2261940T3 (pt) |
FR (1) | FR2838124B1 (pt) |
HK (2) | HK1074632A1 (pt) |
HR (1) | HRP20040911B1 (pt) |
IL (2) | IL164257A0 (pt) |
IS (1) | IS2483B (pt) |
ME (2) | ME00081B (pt) |
MX (1) | MXPA04009635A (pt) |
NO (1) | NO329426B1 (pt) |
NZ (1) | NZ535741A (pt) |
PL (1) | PL372617A1 (pt) |
PT (1) | PT1492792E (pt) |
RS (1) | RS51244B (pt) |
UA (1) | UA77273C2 (pt) |
WO (1) | WO2003082874A2 (pt) |
ZA (1) | ZA200407945B (pt) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1786905B1 (en) * | 2004-08-18 | 2011-08-03 | Lorus Therapeutics Inc. | Small interfering rna molecules against ribonucleotide reductase and uses thereof |
CA2619419A1 (en) * | 2005-08-19 | 2007-03-22 | Schering Corporation | Fused tricyclic mglur1 antagonists as therapeutic agents |
EP2391607A1 (en) * | 2009-01-30 | 2011-12-07 | AstraZeneca AB | Novel process for preparing carboxy-containing pyrazoleamido compounds 597 |
CN105330665B (zh) * | 2015-11-04 | 2017-10-03 | 衡阳师范学院 | 一种抑制激肽释放酶klk7的化合物、制备方法和用途 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2754262B1 (fr) * | 1996-10-08 | 1998-10-30 | Synthelabo | Derives de 1h-pyrido[3,4-b]indole-4-carboxamide, leur preparation et leur application en therapeutique |
FR2766823B1 (fr) * | 1997-07-30 | 1999-10-08 | Synthelabo | Derives de 4-oxo-3,5-dihydro-4h-pyridazino[4,5-b] indole-1-acetamide, leur preparation et leur application en therapeutique |
FR2788696B1 (fr) * | 1999-01-26 | 2004-03-05 | Synthelabo | Utilisation de derives de pyridazino [4,5-b] indole-1-acetamide pour la preparation de medicaments destines aux maladies du systeme nerveux central |
FR2788776B1 (fr) * | 1999-01-26 | 2001-02-23 | Synthelabo | Derives de 4-oxo-3, 5-dihydro-4h-pyridazino [4,5-b] indole-1 -carboxamide, leur preparation et leur application en therapeutique |
FR2811990A1 (fr) * | 2000-07-24 | 2002-01-25 | Sanofi Synthelabo | DERIVES DE 1-(4-OXO-3,5-DIHYDRO-4H-PYRIDAZINO[4,5-b]INDOLE-1 -CARBONYL)PIPERAZINE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
FR2811897A1 (fr) * | 2000-07-24 | 2002-01-25 | Sanofi Synthelabo | UTILISATION DE DERIVES DE PYRIDAZINO[4,5-b]INDOLE-1- ACETAMIDE POUR LA PREPARATION DE MEDICAMENTS DESTINES AU TRAITEMENT DES DYSFONCTIONNEMENTS DES RECEPTEURS DE TYPE PERIPHERIQUE AUX BENZODIAZEPINES |
FR2833953B1 (fr) * | 2001-12-21 | 2004-12-03 | Sanofi Synthelabo | DERIVES DE 3-HETEROARYL-3,5-DIHYDRO-4-OXO-4H-PYRIDAZINO [4,5-b]INDOLE-1-CARBOXAMIDE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
-
2002
- 2002-04-03 FR FR0204158A patent/FR2838124B1/fr not_active Expired - Fee Related
-
2003
- 2003-02-04 UA UA20041008012A patent/UA77273C2/uk unknown
- 2003-04-02 CN CNB038122227A patent/CN100406459C/zh not_active Expired - Fee Related
- 2003-04-02 CA CA2481460A patent/CA2481460C/en not_active Expired - Fee Related
- 2003-04-02 WO PCT/FR2003/001027 patent/WO2003082874A2/fr active Application Filing
- 2003-04-02 PL PL03372617A patent/PL372617A1/xx unknown
- 2003-04-02 BR BR0309018-3A patent/BR0309018A/pt not_active IP Right Cessation
- 2003-04-02 DK DK03730299T patent/DK1492792T3/da active
- 2003-04-02 RS YUP-869/04A patent/RS51244B/sr unknown
- 2003-04-02 KR KR1020047015629A patent/KR100975999B1/ko not_active IP Right Cessation
- 2003-04-02 EP EP03730299A patent/EP1492792B1/fr not_active Expired - Lifetime
- 2003-04-02 AU AU2003240930A patent/AU2003240930B2/en not_active Ceased
- 2003-04-02 US US10/509,695 patent/US7235554B2/en not_active Expired - Lifetime
- 2003-04-02 PT PT03730299T patent/PT1492792E/pt unknown
- 2003-04-02 NZ NZ535741A patent/NZ535741A/en not_active IP Right Cessation
- 2003-04-02 EA EA200401146A patent/EA007219B1/ru not_active IP Right Cessation
- 2003-04-02 AT AT03730299T patent/ATE321763T1/de active
- 2003-04-02 MX MXPA04009635A patent/MXPA04009635A/es active IP Right Grant
- 2003-04-02 DE DE60304327T patent/DE60304327T2/de not_active Expired - Lifetime
- 2003-04-02 JP JP2003580339A patent/JP4575670B2/ja not_active Expired - Fee Related
- 2003-04-02 CN CNB2006101003182A patent/CN100543016C/zh not_active Expired - Fee Related
- 2003-04-02 ES ES03730299T patent/ES2261940T3/es not_active Expired - Lifetime
- 2003-04-02 ME MEP-2008-237A patent/ME00081B/me unknown
- 2003-04-02 IL IL16425703A patent/IL164257A0/xx unknown
- 2003-04-02 ME MEP-237/08A patent/MEP23708A/xx unknown
-
2004
- 2004-09-23 IL IL164257A patent/IL164257A/en not_active IP Right Cessation
- 2004-09-30 IS IS7478A patent/IS2483B/is unknown
- 2004-09-30 NO NO20044153A patent/NO329426B1/no not_active IP Right Cessation
- 2004-10-01 ZA ZA2004/07945A patent/ZA200407945B/en unknown
- 2004-10-04 HR HRP20040911 patent/HRP20040911B1/xx not_active IP Right Cessation
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2005
- 2005-10-04 HK HK05108771A patent/HK1074632A1/xx not_active IP Right Cessation
- 2005-10-04 HK HK07108859.6A patent/HK1102371A1/xx not_active IP Right Cessation
-
2006
- 2006-06-29 CY CY20061100885T patent/CY1104998T1/el unknown
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2007
- 2007-05-16 US US11/749,342 patent/US7323467B2/en not_active Expired - Lifetime
- 2007-10-04 US US11/867,366 patent/US7405306B2/en not_active Expired - Fee Related
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2008
- 2008-06-20 US US12/143,059 patent/US20080255129A1/en not_active Abandoned
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2010
- 2010-06-22 JP JP2010141683A patent/JP5277208B2/ja not_active Expired - Fee Related
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