NO329669B1 - Piperazinylacylpiperidinderivater, deres fremstilling og terapeutiske anvendelse - Google Patents
Piperazinylacylpiperidinderivater, deres fremstilling og terapeutiske anvendelse Download PDFInfo
- Publication number
- NO329669B1 NO329669B1 NO20045331A NO20045331A NO329669B1 NO 329669 B1 NO329669 B1 NO 329669B1 NO 20045331 A NO20045331 A NO 20045331A NO 20045331 A NO20045331 A NO 20045331A NO 329669 B1 NO329669 B1 NO 329669B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- methyl
- trifluoromethyl
- radical
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 94
- 230000001225 therapeutic effect Effects 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 408
- -1 trifluoromethoxy radical Chemical class 0.000 claims abstract description 146
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- 125000005843 halogen group Chemical group 0.000 claims abstract description 23
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 21
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 150000003254 radicals Chemical class 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 239000012453 solvate Substances 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000001412 amines Chemical group 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 230000006870 function Effects 0.000 claims description 6
- 208000014674 injury Diseases 0.000 claims description 6
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 6
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
- 230000008733 trauma Effects 0.000 claims description 6
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
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- 229940079593 drug Drugs 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 4
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 230000002093 peripheral effect Effects 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical group N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 2
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- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
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- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 2
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- 238000003756 stirring Methods 0.000 description 84
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
- 239000012074 organic phase Substances 0.000 description 76
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 36
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- 239000000706 filtrate Substances 0.000 description 29
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- 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
- A61P3/08—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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
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- 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
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- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Oncology (AREA)
- Ophthalmology & Optometry (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0207001 | 2002-06-07 | ||
| PCT/FR2003/001685 WO2003104225A1 (fr) | 2002-06-07 | 2003-06-05 | Derives de piperazinylacylpiperidine, leur preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20045331L NO20045331L (no) | 2005-03-07 |
| NO329669B1 true NO329669B1 (no) | 2010-11-29 |
Family
ID=29724874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20045331A NO329669B1 (no) | 2002-06-07 | 2004-12-06 | Piperazinylacylpiperidinderivater, deres fremstilling og terapeutiske anvendelse |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US7468368B2 (is) |
| EP (2) | EP1513835B1 (is) |
| JP (2) | JP4441401B2 (is) |
| KR (1) | KR100970812B1 (is) |
| CN (1) | CN100448875C (is) |
| AR (2) | AR040246A1 (is) |
| AT (2) | ATE325122T1 (is) |
| AU (2) | AU2003255644B2 (is) |
| BR (1) | BR0311828A (is) |
| CA (1) | CA2487840C (is) |
| CY (2) | CY1107330T1 (is) |
| DE (2) | DE60305037T2 (is) |
| DK (2) | DK1513835T3 (is) |
| EA (1) | EA007501B1 (is) |
| ES (2) | ES2271637T3 (is) |
| HK (1) | HK1076110A1 (is) |
| HR (1) | HRP20041157B1 (is) |
| IS (1) | IS2302B (is) |
| MA (1) | MA27233A1 (is) |
| ME (1) | MEP11508A (is) |
| MX (1) | MXPA04012341A (is) |
| NO (1) | NO329669B1 (is) |
| NZ (1) | NZ537044A (is) |
| PL (1) | PL208711B1 (is) |
| PT (2) | PT1513836E (is) |
| RS (2) | RS52588B (is) |
| TW (2) | TWI283671B (is) |
| UA (1) | UA77526C2 (is) |
| WO (2) | WO2003104225A1 (is) |
| ZA (1) | ZA200409823B (is) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2862967B1 (fr) * | 2003-12-01 | 2006-08-04 | Sanofi Synthelabo | Derives de (4-phenylpiperazin-1-yl)acylpiperidine, leur preparation et leur application en therapeutique |
| FR2862968B1 (fr) * | 2003-12-01 | 2006-08-04 | Sanofi Synthelabo | Derives de 4-[(arylmethyl)aminomethyl]piperidine, leur preparation et leur application en therapeutique |
| US7723362B2 (en) * | 2004-01-08 | 2010-05-25 | Syngenta Crop Protection, Inc. | Pesticidal heterocyclic dihaloallyl compounds |
| CN1984910A (zh) * | 2004-07-16 | 2007-06-20 | 詹森药业有限公司 | 适用于神经变性疾病治疗的哌啶、哌嗪或者吗啉或它们的7元类似物的二聚化合物 |
| CA2580787A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
| WO2006113097A2 (en) * | 2005-04-15 | 2006-10-26 | The University Of North Carolina At Chapel Hill | Methods of facilitating cell survival using neurotrophin mimetics |
| MX2009009948A (es) * | 2007-03-15 | 2009-09-24 | Schering Corp | Derivados de piridazinona utiles como inhibidores de glucano sintasa. |
| MX2009012506A (es) * | 2007-05-21 | 2009-12-09 | Reviva Pharmaceuticals Inc | Composiciones, sintesis, y metodos para utilizar agentes antipsicoticos atipicos basados en quinolinona. |
| DE102007026341A1 (de) | 2007-06-06 | 2008-12-11 | Merck Patent Gmbh | Benzoxazolonderivate |
| DE102007032507A1 (de) | 2007-07-12 | 2009-04-02 | Merck Patent Gmbh | Pyridazinonderivate |
| FR2932482B1 (fr) * | 2008-06-13 | 2010-10-08 | Sanofi Aventis | Nouveaux derives de (phenyl-3,6-dihydro-2h-pyridinyl)- (piperazinyl ponte)-1-alcanone et leur utilisation comme inhibiteurs de p75 |
| FR2932481B1 (fr) | 2008-06-13 | 2010-10-08 | Sanofi Aventis | Derives de 4-{2-°4-phenyl-3,6-dihydro-2h-pyridin-1-yl!-2- oxo-alkyl}-1-piperazin-2-one, leur preparation et leur application en therapeutique. |
| AU2010319349B2 (en) | 2009-11-12 | 2015-07-16 | Pharmatrophix, Inc. | Crystalline forms of neurotrophin mimetic compounds and their salts |
| US10273219B2 (en) | 2009-11-12 | 2019-04-30 | Pharmatrophix, Inc. | Crystalline forms of neurotrophin mimetic compounds and their salts |
| JP2013513628A (ja) | 2009-12-14 | 2013-04-22 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | スフィンゴシンキナーゼの阻害薬 |
| FR2953839A1 (fr) * | 2009-12-14 | 2011-06-17 | Sanofi Aventis | Nouveaux derives d'(heterocycle-piperidine condensee)-(piperazinyl)-1alcanone ou d'(heterocycle-pyrrolidine condensee)-(piperazinyl)-1alcanone et leur utilisation comme inhibiteurs de p75 |
| FR2953836B1 (fr) * | 2009-12-14 | 2012-03-16 | Sanofi Aventis | Nouveaux derives (heterocycle-tetrahydro-pyridine)-(piperazinyl)-1-alcanone et (heterocycle-dihydro-pyrrolidine)-(piperazinyl)-1-alcanone et leur utilisation comme inhibiteurs de p75 |
| EP2606894A1 (en) | 2011-12-20 | 2013-06-26 | Sanofi | Novel therapeutic use of p75 receptor antagonists |
| EP3684364A4 (en) * | 2017-09-18 | 2021-06-02 | Goldfinch Bio, Inc. | PYRIDAZINONE AND METHOD OF USE THEREOF |
| PE20211774A1 (es) | 2018-09-18 | 2021-09-08 | Goldfinch Bio Inc | Piridazinonas y sus metodos de uso |
| EP3858439A1 (en) * | 2020-02-03 | 2021-08-04 | Esteve Pharmaceuticals, S.A. | Amide derivatives having multimodal activity against pain |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4994455A (en) * | 1987-10-26 | 1991-02-19 | Pfizer Inc. | Anti-anxiety agents |
| FR2747041B1 (fr) * | 1996-04-05 | 1998-05-22 | Cird Galderma | Utilisation de derives benzonaphtaleniques pour la fabrication de medicaments destines au traitement des neuropathies |
| US6468990B1 (en) * | 1999-05-17 | 2002-10-22 | Queen's University At Kingston | Method of inhibiting binding of nerve growth factor to p75 NTR receptor |
| FR2803593B1 (fr) * | 2000-01-06 | 2002-02-15 | Sanofi Synthelabo | Nouvelles tetrahydropyridines, procede pour leur preparation et compositions pharmaceutiques les contenant |
-
2003
- 2003-05-06 UA UA20041210010A patent/UA77526C2/uk unknown
- 2003-06-05 DE DE60305037T patent/DE60305037T2/de not_active Expired - Lifetime
- 2003-06-05 WO PCT/FR2003/001685 patent/WO2003104225A1/fr active IP Right Grant
- 2003-06-05 PT PT03757109T patent/PT1513836E/pt unknown
- 2003-06-05 DE DE60307632T patent/DE60307632T2/de not_active Expired - Lifetime
- 2003-06-05 DK DK03757108T patent/DK1513835T3/da active
- 2003-06-05 AT AT03757109T patent/ATE325122T1/de active
- 2003-06-05 ES ES03757108T patent/ES2271637T3/es not_active Expired - Lifetime
- 2003-06-05 JP JP2004511296A patent/JP4441401B2/ja not_active Expired - Fee Related
- 2003-06-05 US US10/516,704 patent/US7468368B2/en active Active
- 2003-06-05 CN CNB038188082A patent/CN100448875C/zh not_active Expired - Fee Related
- 2003-06-05 ES ES03757109T patent/ES2264001T3/es not_active Expired - Lifetime
- 2003-06-05 RS RS20050014A patent/RS52588B/en unknown
- 2003-06-05 EP EP03757108A patent/EP1513835B1/fr not_active Expired - Lifetime
- 2003-06-05 JP JP2004511295A patent/JP4437075B2/ja not_active Expired - Fee Related
- 2003-06-05 PT PT03757108T patent/PT1513835E/pt unknown
- 2003-06-05 AU AU2003255644A patent/AU2003255644B2/en not_active Ceased
- 2003-06-05 MX MXPA04012341A patent/MXPA04012341A/es active IP Right Grant
- 2003-06-05 ME MEP-115/08A patent/MEP11508A/xx unknown
- 2003-06-05 DK DK03757109T patent/DK1513836T3/da active
- 2003-06-05 CA CA2487840A patent/CA2487840C/en not_active Expired - Fee Related
- 2003-06-05 EP EP03757109A patent/EP1513836B1/fr not_active Expired - Lifetime
- 2003-06-05 AU AU2003255645A patent/AU2003255645A1/en not_active Abandoned
- 2003-06-05 WO PCT/FR2003/001686 patent/WO2003104226A1/fr active IP Right Grant
- 2003-06-05 NZ NZ537044A patent/NZ537044A/en not_active IP Right Cessation
- 2003-06-05 BR BR0311828-2A patent/BR0311828A/pt not_active IP Right Cessation
- 2003-06-05 PL PL374729A patent/PL208711B1/pl not_active IP Right Cessation
- 2003-06-05 KR KR1020047019860A patent/KR100970812B1/ko not_active IP Right Cessation
- 2003-06-05 EA EA200401470A patent/EA007501B1/ru not_active IP Right Cessation
- 2003-06-05 AT AT03757108T patent/ATE336491T1/de active
- 2003-06-05 US US10/516,808 patent/US7294628B2/en active Active
- 2003-06-05 RS YUP-2005/0014A patent/RS20050014A/sr unknown
- 2003-06-06 TW TW092115416A patent/TWI283671B/zh not_active IP Right Cessation
- 2003-06-06 AR ARP030102017A patent/AR040246A1/es active IP Right Grant
- 2003-06-06 TW TW092115443A patent/TWI319400B/zh not_active IP Right Cessation
- 2003-06-06 AR ARP030102018A patent/AR040247A1/es active IP Right Grant
-
2004
- 2004-12-02 IS IS7579A patent/IS2302B/is unknown
- 2004-12-03 ZA ZA200409823A patent/ZA200409823B/en unknown
- 2004-12-03 MA MA27980A patent/MA27233A1/fr unknown
- 2004-12-06 NO NO20045331A patent/NO329669B1/no not_active IP Right Cessation
- 2004-12-06 HR HR20041157 patent/HRP20041157B1/xx not_active IP Right Cessation
-
2005
- 2005-11-19 HK HK05110460.5A patent/HK1076110A1/xx not_active IP Right Cessation
-
2006
- 2006-08-03 CY CY20061101094T patent/CY1107330T1/el unknown
- 2006-11-15 CY CY20061101660T patent/CY1105784T1/el unknown
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