CA2446331A1 - 4-(phenyl-piperidin-4-ylidene-methyl)-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders - Google Patents
4-(phenyl-piperidin-4-ylidene-methyl)-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders Download PDFInfo
- Publication number
- CA2446331A1 CA2446331A1 CA002446331A CA2446331A CA2446331A1 CA 2446331 A1 CA2446331 A1 CA 2446331A1 CA 002446331 A CA002446331 A CA 002446331A CA 2446331 A CA2446331 A CA 2446331A CA 2446331 A1 CA2446331 A1 CA 2446331A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- methyl
- ylidene
- piperidin
- benzamide
- 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
- 230000036407 pain Effects 0.000 title claims abstract description 10
- 208000019901 Anxiety disease Diseases 0.000 title claims abstract description 9
- 208000018522 Gastrointestinal disease Diseases 0.000 title claims abstract description 8
- 230000036506 anxiety Effects 0.000 title claims abstract description 8
- 208000027520 Somatoform disease Diseases 0.000 title abstract description 4
- 208000027753 pain disease Diseases 0.000 title abstract description 4
- TZKLMPPHEAGFJR-UHFFFAOYSA-N 4-[phenyl(piperidin-4-ylidene)methyl]benzamide Chemical class C1=CC(C(=O)N)=CC=C1C(C=1C=CC=CC=1)=C1CCNCC1 TZKLMPPHEAGFJR-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 125000002541 furyl group Chemical group 0.000 claims abstract description 6
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 6
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
- 125000002346 iodo group Chemical group I* 0.000 claims abstract description 5
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 3
- 125000001425 triazolyl group Chemical group 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
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- YKZDJDHSSCAGCZ-UHFFFAOYSA-N 4-[(3-hydroxyphenyl)-[1-(1,3-thiazol-2-ylmethyl)piperidin-4-ylidene]methyl]-n,n-di(propan-2-yl)benzamide Chemical compound C1=CC(C(=O)N(C(C)C)C(C)C)=CC=C1C(C=1C=C(O)C=CC=1)=C1CCN(CC=2SC=CN=2)CC1 YKZDJDHSSCAGCZ-UHFFFAOYSA-N 0.000 claims 1
- JGRISOTXIVNHEM-UHFFFAOYSA-N 4-[(3-hydroxyphenyl)-[1-(1h-imidazol-2-ylmethyl)piperidin-4-ylidene]methyl]-n,n-di(propan-2-yl)benzamide Chemical compound C1=CC(C(=O)N(C(C)C)C(C)C)=CC=C1C(C=1C=C(O)C=CC=1)=C1CCN(CC=2NC=CN=2)CC1 JGRISOTXIVNHEM-UHFFFAOYSA-N 0.000 claims 1
- KKKDXIZHAKECPH-UHFFFAOYSA-N 4-[(3-hydroxyphenyl)-[1-(1h-pyrrol-2-ylmethyl)piperidin-4-ylidene]methyl]-n,n-di(propan-2-yl)benzamide Chemical compound C1=CC(C(=O)N(C(C)C)C(C)C)=CC=C1C(C=1C=C(O)C=CC=1)=C1CCN(CC=2NC=CC=2)CC1 KKKDXIZHAKECPH-UHFFFAOYSA-N 0.000 claims 1
- XZRLUGGNSDNNPA-UHFFFAOYSA-N 4-[(3-hydroxyphenyl)-[1-(pyridin-2-ylmethyl)piperidin-4-ylidene]methyl]-n,n-di(propan-2-yl)benzamide Chemical compound C1=CC(C(=O)N(C(C)C)C(C)C)=CC=C1C(C=1C=C(O)C=CC=1)=C1CCN(CC=2N=CC=CC=2)CC1 XZRLUGGNSDNNPA-UHFFFAOYSA-N 0.000 claims 1
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- ZGHXWEPUBQIIBU-UHFFFAOYSA-N 4-[(3-hydroxyphenyl)-[1-(thiophen-2-ylmethyl)piperidin-4-ylidene]methyl]-n,n-di(propan-2-yl)benzamide Chemical compound C1=CC(C(=O)N(C(C)C)C(C)C)=CC=C1C(C=1C=C(O)C=CC=1)=C1CCN(CC=2SC=CC=2)CC1 ZGHXWEPUBQIIBU-UHFFFAOYSA-N 0.000 claims 1
- FZFUOIOHBFULAX-UHFFFAOYSA-N 4-[(3-hydroxyphenyl)-[1-(thiophen-3-ylmethyl)piperidin-4-ylidene]methyl]-n,n-di(propan-2-yl)benzamide Chemical compound C1=CC(C(=O)N(C(C)C)C(C)C)=CC=C1C(C=1C=C(O)C=CC=1)=C1CCN(CC2=CSC=C2)CC1 FZFUOIOHBFULAX-UHFFFAOYSA-N 0.000 claims 1
- RWISWBNYFAHLPO-UHFFFAOYSA-N 4-[(3-hydroxyphenyl)-[1-[(4-methoxyphenyl)methyl]piperidin-4-ylidene]methyl]-n,n-di(propan-2-yl)benzamide Chemical compound C1=CC(OC)=CC=C1CN(CC1)CCC1=C(C=1C=C(O)C=CC=1)C1=CC=C(C(=O)N(C(C)C)C(C)C)C=C1 RWISWBNYFAHLPO-UHFFFAOYSA-N 0.000 claims 1
- IOPTYCUDVSURJE-UHFFFAOYSA-N 4-[[1-(furan-2-ylmethyl)piperidin-4-ylidene]-(3-hydroxyphenyl)methyl]-n,n-di(propan-2-yl)benzamide Chemical compound C1=CC(C(=O)N(C(C)C)C(C)C)=CC=C1C(C=1C=C(O)C=CC=1)=C1CCN(CC=2OC=CC=2)CC1 IOPTYCUDVSURJE-UHFFFAOYSA-N 0.000 claims 1
- RNPRTYDFPBDEIT-UHFFFAOYSA-N 4-[[1-(furan-3-ylmethyl)piperidin-4-ylidene]-(3-hydroxyphenyl)methyl]-n,n-di(propan-2-yl)benzamide Chemical compound C1=CC(C(=O)N(C(C)C)C(C)C)=CC=C1C(C=1C=C(O)C=CC=1)=C1CCN(CC2=COC=C2)CC1 RNPRTYDFPBDEIT-UHFFFAOYSA-N 0.000 claims 1
- PIPMONPNGJEOIM-UHFFFAOYSA-N 4-[[1-[(4-bromophenyl)methyl]piperidin-4-ylidene]-(3-hydroxyphenyl)methyl]-n,n-di(propan-2-yl)benzamide Chemical compound C1=CC(C(=O)N(C(C)C)C(C)C)=CC=C1C(C=1C=C(O)C=CC=1)=C1CCN(CC=2C=CC(Br)=CC=2)CC1 PIPMONPNGJEOIM-UHFFFAOYSA-N 0.000 claims 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D409/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Psychology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0101767A SE0101767D0 (sv) | 2001-05-18 | 2001-05-18 | Novel compounds |
| SE0101767-2 | 2001-05-18 | ||
| PCT/SE2002/000946 WO2002094810A1 (en) | 2001-05-18 | 2002-05-16 | 4-(phenyl-piperidin-4-ylidene-methyl)-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2446331A1 true CA2446331A1 (en) | 2002-11-28 |
Family
ID=20284170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002446331A Abandoned CA2446331A1 (en) | 2001-05-18 | 2002-05-16 | 4-(phenyl-piperidin-4-ylidene-methyl)-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US20040138259A1 (enExample) |
| EP (1) | EP1395574B1 (enExample) |
| JP (1) | JP2005507372A (enExample) |
| KR (1) | KR20030094423A (enExample) |
| CN (1) | CN1547579A (enExample) |
| AR (1) | AR033756A1 (enExample) |
| AT (1) | ATE287400T1 (enExample) |
| BG (1) | BG108328A (enExample) |
| BR (1) | BR0209667A (enExample) |
| CA (1) | CA2446331A1 (enExample) |
| CO (1) | CO5540304A2 (enExample) |
| CZ (1) | CZ20033087A3 (enExample) |
| DE (1) | DE60202679T2 (enExample) |
| EE (1) | EE200300543A (enExample) |
| HU (1) | HUP0401285A2 (enExample) |
| IL (1) | IL158695A0 (enExample) |
| IS (1) | IS7024A (enExample) |
| MX (1) | MXPA03010438A (enExample) |
| NO (1) | NO20035118D0 (enExample) |
| PL (1) | PL366389A1 (enExample) |
| RU (1) | RU2003131968A (enExample) |
| SE (1) | SE0101767D0 (enExample) |
| SK (1) | SK13932003A3 (enExample) |
| WO (1) | WO2002094810A1 (enExample) |
| ZA (1) | ZA200308635B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CL2004000754A1 (es) * | 2003-04-11 | 2005-02-25 | Janssen Pharmaceutica Nv | Uso de compuestos derivados de 4-fenil-4-(1h-imidazol-2-il)piperidina, como agonistas delta-opioides no peptidicos, para preparar un medicamento util en prevenir o tratar trastornos del sistema nervioso central. |
| RU2005136524A (ru) * | 2003-05-16 | 2006-06-27 | Астразенека Аб (Se) | Производные диарилметилиденпиперидина, способы их получения и их применение |
| SE0301443D0 (sv) * | 2003-05-16 | 2003-05-16 | Astrazeneca Ab | Diarylmethylidene piperidine derivatives, preparations thereof and uses thereof |
| WO2005005478A2 (en) * | 2003-07-02 | 2005-01-20 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with g protein-coupled opioid receptor; delta 1 (oprd1) |
| KR20140015122A (ko) | 2003-10-01 | 2014-02-06 | 아돌로 코포레이션 | 스피로시클릭 헤테로시클릭 유도체 및 이의 사용 방법 |
| US7598261B2 (en) | 2005-03-31 | 2009-10-06 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| US7576207B2 (en) | 2006-04-06 | 2009-08-18 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| WO2008033299A2 (en) | 2006-09-12 | 2008-03-20 | Adolor Corporation | Use of n-containing spirocompounds for the enhancement of cognitive function |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2898339A (en) * | 1957-07-29 | 1959-08-04 | Wm S Merrell Co | N-substituted benzhydrol, benzhydryl, and benzhydrylidene piperidine |
| US4581171A (en) * | 1983-07-27 | 1986-04-08 | Janssen Pharmaceutica, N.V. | [[Bis(aryl)methylene]-1-piperidinyl]alkyl-pyrimidinones useful for treating psychotropic disorders |
| US4816586A (en) * | 1987-07-29 | 1989-03-28 | Regents Of The University Of Minnesota | Delta opioid receptor antagonists |
| US5140029A (en) * | 1989-01-09 | 1992-08-18 | Janssen Pharmaceutica N.V. | 2-aminopyrimidinone derivatives |
| US4939137A (en) * | 1989-06-28 | 1990-07-03 | Ortho Pharmaceutical Corporation | Ring-fused thienopyrimidinedione derivatives |
| US5683998A (en) * | 1991-04-23 | 1997-11-04 | Toray Industries, Inc. | Tricyclic triazolo derivatives, processes for producing the same and the uses of the same |
| US5574159A (en) * | 1992-02-03 | 1996-11-12 | Delta Pharmaceuticals, Inc. | Opioid compounds and methods for making therefor |
| TW548271B (en) * | 1996-12-20 | 2003-08-21 | Astra Pharma Inc | Novel piperidine derivatives having an exocyclic double bond with analgesic effects |
| US6436959B1 (en) * | 1998-12-23 | 2002-08-20 | Ortho-Mcneil Pharmaceutical, Inc. | 4-[aryl(piperidin-4-yl)]aminobenzamides |
| SE0001207D0 (sv) * | 2000-04-04 | 2000-04-04 | Astrazeneca Canada Inc | Novel compounds |
-
2001
- 2001-05-18 SE SE0101767A patent/SE0101767D0/xx unknown
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2002
- 2002-05-16 EP EP02733703A patent/EP1395574B1/en not_active Expired - Lifetime
- 2002-05-16 KR KR10-2003-7014944A patent/KR20030094423A/ko not_active Withdrawn
- 2002-05-16 PL PL02366389A patent/PL366389A1/xx not_active Application Discontinuation
- 2002-05-16 US US10/477,854 patent/US20040138259A1/en not_active Abandoned
- 2002-05-16 SK SK1393-2003A patent/SK13932003A3/sk unknown
- 2002-05-16 RU RU2003131968/04A patent/RU2003131968A/ru not_active Application Discontinuation
- 2002-05-16 AT AT02733703T patent/ATE287400T1/de not_active IP Right Cessation
- 2002-05-16 MX MXPA03010438A patent/MXPA03010438A/es unknown
- 2002-05-16 DE DE60202679T patent/DE60202679T2/de not_active Expired - Fee Related
- 2002-05-16 BR BR0209667-6A patent/BR0209667A/pt not_active Application Discontinuation
- 2002-05-16 EE EEP200300543A patent/EE200300543A/xx unknown
- 2002-05-16 CN CNA02810191XA patent/CN1547579A/zh active Pending
- 2002-05-16 CZ CZ20033087A patent/CZ20033087A3/cs unknown
- 2002-05-16 HU HU0401285A patent/HUP0401285A2/hu unknown
- 2002-05-16 CA CA002446331A patent/CA2446331A1/en not_active Abandoned
- 2002-05-16 IL IL15869502A patent/IL158695A0/xx unknown
- 2002-05-16 JP JP2002591483A patent/JP2005507372A/ja active Pending
- 2002-05-16 WO PCT/SE2002/000946 patent/WO2002094810A1/en not_active Ceased
- 2002-05-16 AR ARP020101812A patent/AR033756A1/es not_active Application Discontinuation
-
2003
- 2003-11-05 ZA ZA200308635A patent/ZA200308635B/en unknown
- 2003-11-07 BG BG108328A patent/BG108328A/bg unknown
- 2003-11-11 IS IS7024A patent/IS7024A/is unknown
- 2003-11-12 CO CO03100160A patent/CO5540304A2/es not_active Application Discontinuation
- 2003-11-17 NO NO20035118A patent/NO20035118D0/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL366389A1 (en) | 2005-01-24 |
| JP2005507372A (ja) | 2005-03-17 |
| EP1395574A1 (en) | 2004-03-10 |
| EP1395574B1 (en) | 2005-01-19 |
| DE60202679T2 (de) | 2006-03-30 |
| DE60202679D1 (de) | 2005-02-24 |
| CO5540304A2 (es) | 2005-07-29 |
| CN1547579A (zh) | 2004-11-17 |
| WO2002094810A1 (en) | 2002-11-28 |
| EE200300543A (et) | 2004-02-16 |
| RU2003131968A (ru) | 2005-05-10 |
| US20040138259A1 (en) | 2004-07-15 |
| IL158695A0 (en) | 2004-05-12 |
| BR0209667A (pt) | 2004-04-20 |
| SE0101767D0 (sv) | 2001-05-18 |
| MXPA03010438A (es) | 2004-03-09 |
| ATE287400T1 (de) | 2005-02-15 |
| ZA200308635B (en) | 2005-02-07 |
| SK13932003A3 (sk) | 2004-05-04 |
| BG108328A (bg) | 2004-12-30 |
| NO20035118D0 (no) | 2003-11-17 |
| HUP0401285A2 (hu) | 2004-12-28 |
| AR033756A1 (es) | 2004-01-07 |
| IS7024A (is) | 2003-11-11 |
| CZ20033087A3 (cs) | 2004-05-12 |
| KR20030094423A (ko) | 2003-12-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |