IL171087A - 4-(2-phenylsulfanyl-phenyl)-piperidine derivatives as serotonin reuptake inhibitors - Google Patents
4-(2-phenylsulfanyl-phenyl)-piperidine derivatives as serotonin reuptake inhibitorsInfo
- Publication number
- IL171087A IL171087A IL171087A IL17108705A IL171087A IL 171087 A IL171087 A IL 171087A IL 171087 A IL171087 A IL 171087A IL 17108705 A IL17108705 A IL 17108705A IL 171087 A IL171087 A IL 171087A
- Authority
- IL
- Israel
- Prior art keywords
- alk
- fluoro
- hydrogen
- phenyl
- piperidine
- Prior art date
Links
- 239000003772 serotonin uptake inhibitor Substances 0.000 title description 15
- OITWUTJGZGVOKQ-UHFFFAOYSA-N 4-(2-phenylsulfanylphenyl)piperidine Chemical class C1CNCCC1C1=CC=CC=C1SC1=CC=CC=C1 OITWUTJGZGVOKQ-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 230
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 20
- 208000019906 panic disease Diseases 0.000 claims abstract description 14
- 208000019022 Mood disease Diseases 0.000 claims abstract description 8
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims description 143
- 229910052739 hydrogen Inorganic materials 0.000 claims description 143
- -1 Ci-6-alkyl Inorganic materials 0.000 claims description 89
- 229910052736 halogen Inorganic materials 0.000 claims description 85
- 150000002367 halogens Chemical group 0.000 claims description 82
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 75
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 206010041250 Social phobia Diseases 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 208000008811 Agoraphobia Diseases 0.000 claims description 6
- 206010033664 Panic attack Diseases 0.000 claims description 6
- 206010034912 Phobia Diseases 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 6
- 201000001716 specific phobia Diseases 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims 26
- VUDOWOVTAVLYGF-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)sulfanyl-5-(trifluoromethyl)phenyl]piperidine Chemical compound C1CNCCC1C1=CC(C(F)(F)F)=CC=C1SC1=CC=C(Cl)C=C1 VUDOWOVTAVLYGF-UHFFFAOYSA-N 0.000 claims 1
- LGMJHHBWRCGXHG-UHFFFAOYSA-N CC1=C(C=CC(=C1)C)SC1=C(C=C(C=C1)C)C1CCNCC1.CC1=CC=C(C=C1)SC1=C(C=C(C=C1)C)C1CCNCC1.COC1=CC=C(C=C1)SC1=C(C=CC(=C1)F)C1CCNCC1 Chemical compound CC1=C(C=CC(=C1)C)SC1=C(C=C(C=C1)C)C1CCNCC1.CC1=CC=C(C=C1)SC1=C(C=C(C=C1)C)C1CCNCC1.COC1=CC=C(C=C1)SC1=C(C=CC(=C1)F)C1CCNCC1 LGMJHHBWRCGXHG-UHFFFAOYSA-N 0.000 claims 1
- QLWDIUDVIWUHHI-UHFFFAOYSA-N COC1=CC=C(C=C1)SC1=C(C=C(C=C1)C)C1CCNCC1.FC1=CC(=C(C=C1)SC1=C(C=C(C=C1)C)C1CCNCC1)C Chemical compound COC1=CC=C(C=C1)SC1=C(C=C(C=C1)C)C1CCNCC1.FC1=CC(=C(C=C1)SC1=C(C=C(C=C1)C)C1CCNCC1)C QLWDIUDVIWUHHI-UHFFFAOYSA-N 0.000 claims 1
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- 239000012043 crude product Substances 0.000 description 15
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- 229910052763 palladium Inorganic materials 0.000 description 12
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- 239000011780 sodium chloride Substances 0.000 description 9
- 235000019270 ammonium chloride Nutrition 0.000 description 8
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- 238000010168 coupling process Methods 0.000 description 8
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 8
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- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 7
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- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 7
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- LYQRZYFUNCUAAK-UHFFFAOYSA-N tert-butyl 4-[2-(4-chlorophenyl)sulfanylphenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=CC=C1SC1=CC=C(Cl)C=C1 LYQRZYFUNCUAAK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- 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
-
- 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
- A61P25/22—Anxiolytics
-
- 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
-
- 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
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/24—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by sulfur atoms to which a second hetero atom is attached
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46052803P | 2003-04-04 | 2003-04-04 | |
| DKPA200300520 | 2003-04-04 | ||
| PCT/DK2004/000244 WO2004087156A1 (en) | 2003-04-04 | 2004-04-02 | 4-(2-phenylsulfanyl-phenyl)-piperidine derivatives as serotonin reuptake inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL171087A true IL171087A (en) | 2011-01-31 |
Family
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Family Applications (1)
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|---|---|---|---|
| IL171087A IL171087A (en) | 2003-04-04 | 2005-09-25 | 4-(2-phenylsulfanyl-phenyl)-piperidine derivatives as serotonin reuptake inhibitors |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7732463B2 (enExample) |
| EP (1) | EP1626720B1 (enExample) |
| JP (1) | JP4667366B2 (enExample) |
| AT (1) | ATE406894T1 (enExample) |
| AU (1) | AU2004226838B8 (enExample) |
| CA (1) | CA2521258C (enExample) |
| CO (1) | CO5700748A2 (enExample) |
| CY (1) | CY1108464T1 (enExample) |
| DE (1) | DE602004016316D1 (enExample) |
| DK (1) | DK1626720T3 (enExample) |
| ES (1) | ES2309514T3 (enExample) |
| HR (1) | HRP20080478T3 (enExample) |
| IL (1) | IL171087A (enExample) |
| MX (1) | MXPA05009592A (enExample) |
| NO (1) | NO20055208L (enExample) |
| PL (1) | PL1626720T3 (enExample) |
| PT (1) | PT1626720E (enExample) |
| SI (1) | SI1626720T1 (enExample) |
| WO (1) | WO2004087156A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA81749C2 (uk) * | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
| EP1792629A4 (en) | 2004-08-25 | 2010-08-25 | Takeda Pharmaceutical | MEANS FOR THE PREVENTION / TREATMENT OF STRESS-RELATED HARNINE INCONTINENCE AND PRECAUTIONARY METHOD FOR THIS |
| JP5528699B2 (ja) | 2006-05-16 | 2014-06-25 | 武田薬品工業株式会社 | 縮合複素環化合物およびその用途 |
| EP2439201B1 (en) | 2006-06-16 | 2013-08-07 | H. Lundbeck A/S | Compounds with combined sert, 5-ht3 and 5-ht1a activity |
| TWI432194B (zh) * | 2007-03-20 | 2014-04-01 | Lundbeck & Co As H | ４-〔２-（４-甲基苯硫基）苯基〕哌啶之新穎治療用途 |
| TWI405588B (zh) * | 2007-03-20 | 2013-08-21 | Lundbeck & Co As H | ４-〔２-（４-甲苯基硫基）-苯基〕哌啶之鹽類的液體調配物 |
| TW200932233A (en) | 2007-11-13 | 2009-08-01 | Lundbeck & Co As H | Therapeutic uses of compounds having combined SERT, 5-HT3 and 5-HT1a activity |
| WO2009063992A1 (ja) | 2007-11-15 | 2009-05-22 | Takeda Pharmaceutical Company Limited | 縮合ピリジン誘導体およびその用途 |
| TW200938194A (en) * | 2007-12-14 | 2009-09-16 | Lundbeck & Co As H | Therapeutic uses of compounds having affinity to the serotonin transporter, serotonin receptors and noradrenalin transporter |
| TW200932225A (en) * | 2007-12-14 | 2009-08-01 | Lundbeck & Co As H | 4-[2,3-difluoro-6-(2-fluoro-4-methyl-phenylsulfanyl)-phenyl]-piperidine |
| UA98698C2 (en) * | 2008-03-03 | 2012-06-11 | Х. Луннбек А/С | Phenylsulfanylphenyl-piperidines and process for the preparation thereof |
| HRP20140880T1 (hr) | 2009-04-24 | 2014-11-07 | H. Lundbeck A/S | Tekuä†a formulacija soli 1-/2-(2,4 dimetilfenilsulfanil)fenil/piperazina |
| EP2510949A4 (en) | 2009-12-11 | 2013-11-13 | Astellas Pharma Inc | THERAPEUTICS FOR FIBROMYALGIA |
| EP2564838A4 (en) * | 2010-04-30 | 2014-06-04 | Takeda Pharmaceutical | ENTERICIAN TABLET |
| US8920840B2 (en) * | 2010-04-30 | 2014-12-30 | Takeda Pharmaceutical Company Limited | Enteric tablet |
| EP3733204A4 (en) | 2017-12-27 | 2021-09-15 | Takeda Pharmaceutical Company Limited | THERAPEUTIC AGENT FOR URINARY INCONTINENCE OF STRESS AND FECAL INCONTINENCE |
| AU2019232437A1 (en) | 2018-03-07 | 2020-10-08 | Bayer Aktiengesellschaft | Identification and use of ERK5 inhibitors |
| CN119546584A (zh) | 2022-05-11 | 2025-02-28 | Pi工业有限公司 | 双环化合物及其作为害虫控制剂的用途 |
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| DE2802306A1 (de) * | 1977-01-27 | 1978-08-10 | Hoechst Ag | Azacycloalkane, azacycloalkene und ihre derivate |
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| EP0396827A1 (en) | 1989-05-09 | 1990-11-14 | SPOFA Spojené Podniky Pro Zdravotnickou Vyrobu | 2-Phenylthiobenzylamine dervivatives and acid addition salts thereof |
| GB8912971D0 (en) | 1989-06-06 | 1989-07-26 | Wellcome Found | Halogen substituted diphenylsulfides |
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| CZ293595A3 (cs) | 1995-11-09 | 1999-12-15 | Farmak A. S. | Deriváty N,N-dimethyl-2-(arylthio)benzylaminu, jejich soli, způsoby jejich přípravy a jejich použití v léčivých přípravcích |
| US5912256A (en) | 1996-06-20 | 1999-06-15 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| AU4091697A (en) | 1996-08-27 | 1998-03-19 | American Home Products Corporation | 4-aminoethoxy indoles as dopamin d2 agonists and as 5ht1a ligands |
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| CN1721401A (zh) | 1999-04-02 | 2006-01-18 | 伊科斯公司 | 白细胞功能相关抗原与细胞间粘着分子结合的抑制剂及其用途 |
| JP2002543173A (ja) | 1999-04-30 | 2002-12-17 | ザ トラスティーズ オブ ザ ユニバーシティ オブ ペンシルベニア | セロトニン輸送体のためのｓｐｅｃｔ画像化剤 |
| WO2001010842A2 (en) | 1999-08-04 | 2001-02-15 | Millennium Pharmaceuticals, Inc. | Melanocortin-4 receptor binding compounds and methods of use thereof |
| HUP0203448A3 (en) * | 1999-10-13 | 2005-07-28 | Pfizer Prod Inc | Biaryl ether derivatives useful as monoamine reuptake inhibitors and pharmaceutical compositions containing them |
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| US6436938B1 (en) * | 2001-01-22 | 2002-08-20 | Pfizer Inc. | Combination treatment for depression |
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| SK16052003A3 (en) | 2001-06-07 | 2004-10-05 | Hoffmann La Roche | New indole derivatives with 5-HT6 receptor affinity |
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| HUP0402319A2 (hu) | 2001-12-21 | 2005-02-28 | H. Lundbeck A/S | Szerotonin és norepinefrin felvételt gátló aminoindán-származékok |
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| WO2005000309A2 (en) | 2003-06-27 | 2005-01-06 | Ionix Pharmaceuticals Limited | Chemical compounds |
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2004
- 2004-04-02 SI SI200430864T patent/SI1626720T1/sl unknown
- 2004-04-02 JP JP2006504349A patent/JP4667366B2/ja not_active Expired - Fee Related
- 2004-04-02 EP EP04725291A patent/EP1626720B1/en not_active Expired - Lifetime
- 2004-04-02 AU AU2004226838A patent/AU2004226838B8/en not_active Ceased
- 2004-04-02 AT AT04725291T patent/ATE406894T1/de active
- 2004-04-02 PT PT04725291T patent/PT1626720E/pt unknown
- 2004-04-02 MX MXPA05009592A patent/MXPA05009592A/es active IP Right Grant
- 2004-04-02 PL PL04725291T patent/PL1626720T3/pl unknown
- 2004-04-02 US US10/551,883 patent/US7732463B2/en not_active Expired - Fee Related
- 2004-04-02 DK DK04725291T patent/DK1626720T3/da active
- 2004-04-02 HR HR20080478T patent/HRP20080478T3/xx unknown
- 2004-04-02 DE DE602004016316T patent/DE602004016316D1/de not_active Expired - Lifetime
- 2004-04-02 WO PCT/DK2004/000244 patent/WO2004087156A1/en not_active Ceased
- 2004-04-02 ES ES04725291T patent/ES2309514T3/es not_active Expired - Lifetime
- 2004-04-02 CA CA002521258A patent/CA2521258C/en not_active Expired - Fee Related
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- 2005-09-25 IL IL171087A patent/IL171087A/en not_active IP Right Cessation
- 2005-11-03 CO CO05112440A patent/CO5700748A2/es not_active Application Discontinuation
- 2005-11-04 NO NO20055208A patent/NO20055208L/no not_active Application Discontinuation
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- 2008-10-30 CY CY20081101225T patent/CY1108464T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004226838A1 (en) | 2004-10-14 |
| HRP20080478T3 (hr) | 2009-02-28 |
| AU2004226838B8 (en) | 2009-06-11 |
| AU2004226838B2 (en) | 2009-02-12 |
| MXPA05009592A (es) | 2005-10-18 |
| ATE406894T1 (de) | 2008-09-15 |
| PL1626720T3 (pl) | 2009-02-27 |
| JP4667366B2 (ja) | 2011-04-13 |
| US7732463B2 (en) | 2010-06-08 |
| CA2521258A1 (en) | 2004-10-14 |
| EP1626720A1 (en) | 2006-02-22 |
| WO2004087156A1 (en) | 2004-10-14 |
| CA2521258C (en) | 2009-12-01 |
| EP1626720B1 (en) | 2008-09-03 |
| CO5700748A2 (es) | 2006-11-30 |
| SI1626720T1 (sl) | 2008-12-31 |
| DE602004016316D1 (de) | 2008-10-16 |
| DK1626720T3 (da) | 2008-12-01 |
| ES2309514T3 (es) | 2008-12-16 |
| JP2006522030A (ja) | 2006-09-28 |
| NO20055208L (no) | 2005-11-04 |
| CY1108464T1 (el) | 2014-04-09 |
| PT1626720E (pt) | 2008-11-10 |
| US20060100242A1 (en) | 2006-05-11 |
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