CA2548039A1 - 5-fluoro-, chloro- and cyano-pyridin-2-yl-tetrazoles as ligands of the metabotropic glutamate receptor-5 - Google Patents
5-fluoro-, chloro- and cyano-pyridin-2-yl-tetrazoles as ligands of the metabotropic glutamate receptor-5 Download PDFInfo
- Publication number
- CA2548039A1 CA2548039A1 CA002548039A CA2548039A CA2548039A1 CA 2548039 A1 CA2548039 A1 CA 2548039A1 CA 002548039 A CA002548039 A CA 002548039A CA 2548039 A CA2548039 A CA 2548039A CA 2548039 A1 CA2548039 A1 CA 2548039A1
- Authority
- CA
- Canada
- Prior art keywords
- tetrazol
- fluoro
- compounds
- cyano
- benzonitrile
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 title claims 6
- 239000003446 ligand Substances 0.000 title description 5
- LYOJURLAGFMSOQ-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)pyridine-3-carbonitrile Chemical class N#CC1=CC=CN=C1C1=NNN=N1 LYOJURLAGFMSOQ-UHFFFAOYSA-N 0.000 title 1
- 102100038357 Metabotropic glutamate receptor 5 Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 119
- 238000000034 method Methods 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 230000008569 process Effects 0.000 claims abstract description 18
- 239000012453 solvate Substances 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 7
- 238000011282 treatment Methods 0.000 claims description 40
- -1 chloro, bromo, iodo, methoxymethyl Chemical group 0.000 claims description 35
- 102000005962 receptors Human genes 0.000 claims description 30
- 108020003175 receptors Proteins 0.000 claims description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 208000035475 disorder Diseases 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 230000004913 activation Effects 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 230000001404 mediated effect Effects 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 208000002193 Pain Diseases 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 8
- 150000001412 amines Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 235000010288 sodium nitrite Nutrition 0.000 claims description 4
- XUICYRFPJOHKGW-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-(methoxymethyl)benzonitrile Chemical compound COCC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 XUICYRFPJOHKGW-UHFFFAOYSA-N 0.000 claims description 3
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- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- AQGCLHIWIZUYPV-UHFFFAOYSA-N 3-(difluoromethoxy)-5-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]benzonitrile Chemical compound FC(F)OC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 AQGCLHIWIZUYPV-UHFFFAOYSA-N 0.000 claims description 2
- RNUMNUGYLBCCEU-UHFFFAOYSA-N 3-(ethylamino)-5-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]benzonitrile Chemical compound CCNC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 RNUMNUGYLBCCEU-UHFFFAOYSA-N 0.000 claims description 2
- SAWSSPISYVVUPP-UHFFFAOYSA-N 3-[5-(5-chloropyridin-2-yl)tetrazol-2-yl]-5-fluorobenzonitrile Chemical compound FC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(Cl)=CC=2)=C1 SAWSSPISYVVUPP-UHFFFAOYSA-N 0.000 claims description 2
- WQWFBZQKKNQGSY-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-(2-methoxyethoxy)benzonitrile Chemical compound COCCOC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 WQWFBZQKKNQGSY-UHFFFAOYSA-N 0.000 claims description 2
- UYRBZIYJANWFLG-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-(trifluoromethoxy)benzonitrile Chemical compound N1=CC(F)=CC=C1C1=NN(C=2C=C(C=C(OC(F)(F)F)C=2)C#N)N=N1 UYRBZIYJANWFLG-UHFFFAOYSA-N 0.000 claims description 2
- NDUDAERNMBXBRF-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-iodobenzonitrile Chemical compound N1=CC(F)=CC=C1C1=NN(C=2C=C(C=C(I)C=2)C#N)N=N1 NDUDAERNMBXBRF-UHFFFAOYSA-N 0.000 claims description 2
- HVPQJXMCMHHZHI-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 HVPQJXMCMHHZHI-UHFFFAOYSA-N 0.000 claims description 2
- UQCQFXVIFGQFRL-UHFFFAOYSA-N 3-fluoro-5-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]benzonitrile Chemical compound N1=CC(F)=CC=C1C1=NN(C=2C=C(C=C(F)C=2)C#N)N=N1 UQCQFXVIFGQFRL-UHFFFAOYSA-N 0.000 claims description 2
- IFOXWHQFTSCNQB-UHFFFAOYSA-N 5-aminopyridine-2-carbonitrile Chemical group NC1=CC=C(C#N)N=C1 IFOXWHQFTSCNQB-UHFFFAOYSA-N 0.000 claims description 2
- QJWNJNTZXKFBKG-UHFFFAOYSA-N 5-fluoro-2-[2-(3-fluoro-5-methoxyphenyl)tetrazol-5-yl]pyridine Chemical compound COC1=CC(F)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 QJWNJNTZXKFBKG-UHFFFAOYSA-N 0.000 claims description 2
- BHXHRMVSUUPOLX-UHFFFAOYSA-N 5-fluoropyridine-2-carbonitrile Chemical compound FC1=CC=C(C#N)N=C1 BHXHRMVSUUPOLX-UHFFFAOYSA-N 0.000 claims description 2
- RFXRMGATCPIUGX-UHFFFAOYSA-N 6-[2-(3-cyano-5-fluorophenyl)tetrazol-5-yl]pyridine-3-carbonitrile Chemical compound FC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(=CC=2)C#N)=C1 RFXRMGATCPIUGX-UHFFFAOYSA-N 0.000 claims description 2
- WLBDEBUYJGERNR-UHFFFAOYSA-N 6-[5-(3-cyano-5-fluorophenyl)tetrazol-2-yl]pyridine-3-carbonitrile Chemical compound FC1=CC(C#N)=CC(C2=NN(N=N2)C=2N=CC(=CC=2)C#N)=C1 WLBDEBUYJGERNR-UHFFFAOYSA-N 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 230000000063 preceeding effect Effects 0.000 claims 4
- FBUHFQUZAYMTOM-UHFFFAOYSA-N pyridin-2-ylcyanamide Chemical compound N#CNC1=CC=CC=N1 FBUHFQUZAYMTOM-UHFFFAOYSA-N 0.000 claims 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- GTANSZNHJARZLJ-UHFFFAOYSA-N 3-[2-(5-chloropyridin-2-yl)tetrazol-5-yl]-5-fluorobenzonitrile Chemical compound FC1=CC(C#N)=CC(C2=NN(N=N2)C=2N=CC(Cl)=CC=2)=C1 GTANSZNHJARZLJ-UHFFFAOYSA-N 0.000 claims 1
- TUVRMXKPGAJUGF-UHFFFAOYSA-N 3-amino-5-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]benzonitrile Chemical compound NC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 TUVRMXKPGAJUGF-UHFFFAOYSA-N 0.000 claims 1
- CKISQUUTFPIQAX-UHFFFAOYSA-N 3-fluoro-5-[2-(5-fluoropyridin-2-yl)tetrazol-5-yl]benzonitrile Chemical compound N1=CC(F)=CC=C1N1N=C(C=2C=C(C=C(F)C=2)C#N)N=N1 CKISQUUTFPIQAX-UHFFFAOYSA-N 0.000 claims 1
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- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
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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
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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
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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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
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- A61P27/06—Antiglaucoma agents or miotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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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
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- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Addiction (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53063303P | 2003-12-19 | 2003-12-19 | |
| US60/530,633 | 2003-12-19 | ||
| PCT/US2004/041401 WO2005066155A1 (en) | 2003-12-19 | 2004-12-13 | 5-fluoro-, chloro- and cyano-pyridin-2-yl-tetrazoles as ligands of the metabotropic glutamate receptor-5 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2548039A1 true CA2548039A1 (en) | 2005-07-21 |
Family
ID=34748746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002548039A Abandoned CA2548039A1 (en) | 2003-12-19 | 2004-12-13 | 5-fluoro-, chloro- and cyano-pyridin-2-yl-tetrazoles as ligands of the metabotropic glutamate receptor-5 |
Country Status (20)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1706392A2 (en) * | 2004-01-08 | 2006-10-04 | Syngenta Participations AG | Pesticidal heterocyclic dihaloallyl compounds |
| UY29796A1 (es) | 2005-09-29 | 2007-04-30 | Astrazeneca Ab | Nuevos compuestos para el tratamiento de trastornos neurológicos, psiquiátricos o del dolor |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| US20120095056A1 (en) * | 2009-03-19 | 2012-04-19 | Neurosearch A/S | 2,5-disubstituted tetrazole derivatives and their use as nicotinic acetylcholine receptor modulators |
| WO2011073297A1 (en) * | 2009-12-18 | 2011-06-23 | Neurosearch A/S | Tetrazole derivatives as nicotinic acetylcholine receptor moudlators |
| WO2011073298A1 (en) * | 2009-12-18 | 2011-06-23 | Neurosearch A/S | Tetrazole derivatives as nicotinic acetylcholine receptor modulators |
| CN102762572A (zh) | 2010-02-01 | 2012-10-31 | 诺瓦提斯公司 | 作为CRF-1受体拮抗剂的吡唑并[5,1b]*唑衍生物 |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| EP2531490B1 (en) | 2010-02-02 | 2014-10-15 | Novartis AG | Cyclohexyl amide derivatives as crf receptor antagonists |
| GB201312800D0 (en) | 2013-07-17 | 2013-08-28 | Heptares Therapeutics Ltd | mGlu5 modulators |
| WO2016001452A1 (en) | 2014-07-04 | 2016-01-07 | Universität Zürich | Compounds, in particular for use in the treatment of a disease or condition for which a bromodomain inhibitor is indicated |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6660753B2 (en) * | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| PL369598A1 (en) * | 2001-02-21 | 2005-05-02 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| CA2462289C (en) * | 2001-10-04 | 2010-02-23 | Nicholas D. Cosford | Heteroaryl substituted tetrazole modulators of metabotropic glutamate receptor-5 |
-
2004
- 2004-12-13 EP EP04813689A patent/EP1713791B1/en not_active Expired - Lifetime
- 2004-12-13 WO PCT/US2004/041401 patent/WO2005066155A1/en not_active Ceased
- 2004-12-13 RU RU2006118021/04A patent/RU2006118021A/ru not_active Application Discontinuation
- 2004-12-13 US US10/582,051 patent/US20070255061A1/en not_active Abandoned
- 2004-12-13 MX MXPA06006674A patent/MXPA06006674A/es unknown
- 2004-12-13 CN CNA2004800406448A patent/CN1906187A/zh active Pending
- 2004-12-13 JP JP2006545760A patent/JP2007514790A/ja active Pending
- 2004-12-13 DE DE602004013469T patent/DE602004013469T9/de not_active Expired - Fee Related
- 2004-12-13 KR KR1020067011449A patent/KR20060126993A/ko not_active Withdrawn
- 2004-12-13 AT AT04813689T patent/ATE393767T1/de not_active IP Right Cessation
- 2004-12-13 ES ES04813689T patent/ES2303969T3/es not_active Expired - Lifetime
- 2004-12-13 AU AU2004312342A patent/AU2004312342A1/en not_active Abandoned
- 2004-12-13 BR BRPI0417308-2A patent/BRPI0417308A/pt not_active IP Right Cessation
- 2004-12-13 CA CA002548039A patent/CA2548039A1/en not_active Abandoned
- 2004-12-16 TW TW093139143A patent/TW200524602A/zh unknown
- 2004-12-16 AR ARP040104711A patent/AR046768A1/es unknown
- 2004-12-17 UY UY28685A patent/UY28685A1/es unknown
-
2006
- 2006-05-25 IL IL175909A patent/IL175909A0/en unknown
- 2006-06-01 NO NO20062533A patent/NO20062533L/no not_active Application Discontinuation
- 2006-06-07 ZA ZA200604681A patent/ZA200604681B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| UY28685A1 (es) | 2005-06-30 |
| RU2006118021A (ru) | 2007-12-10 |
| HK1095598A1 (en) | 2007-05-11 |
| IL175909A0 (en) | 2008-02-09 |
| EP1713791A1 (en) | 2006-10-25 |
| WO2005066155A1 (en) | 2005-07-21 |
| DE602004013469T2 (de) | 2009-06-18 |
| AR046768A1 (es) | 2005-12-21 |
| ATE393767T1 (de) | 2008-05-15 |
| MXPA06006674A (es) | 2007-04-16 |
| US20070255061A1 (en) | 2007-11-01 |
| AU2004312342A1 (en) | 2005-07-21 |
| EP1713791B1 (en) | 2008-04-30 |
| ZA200604681B (en) | 2007-04-25 |
| CN1906187A (zh) | 2007-01-31 |
| TW200524602A (en) | 2005-08-01 |
| KR20060126993A (ko) | 2006-12-11 |
| JP2007514790A (ja) | 2007-06-07 |
| DE602004013469D1 (de) | 2008-06-12 |
| BRPI0417308A (pt) | 2007-09-11 |
| ES2303969T3 (es) | 2008-09-01 |
| NO20062533L (no) | 2006-09-19 |
| DE602004013469T9 (de) | 2009-09-24 |
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