HRP20050229A2 - 2,7-substituirani indoli i njihova uporaba kao modulatora za 5-ht6 - Google Patents
2,7-substituirani indoli i njihova uporaba kao modulatora za 5-ht6 Download PDFInfo
- Publication number
- HRP20050229A2 HRP20050229A2 HR20050229A HRP20050229A HRP20050229A2 HR P20050229 A2 HRP20050229 A2 HR P20050229A2 HR 20050229 A HR20050229 A HR 20050229A HR P20050229 A HRP20050229 A HR P20050229A HR P20050229 A2 HRP20050229 A2 HR P20050229A2
- Authority
- HR
- Croatia
- Prior art keywords
- indole
- alkyl
- substituted
- halo
- aryl
- Prior art date
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- 150000002475 indoles Chemical class 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 238000000034 method Methods 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- -1 N-methyl piperidin-4-yl Chemical group 0.000 claims description 47
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
- 201000010099 disease Diseases 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000006239 protecting group Chemical group 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 9
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 7
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- 208000015114 central nervous system disease Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
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- 208000028683 bipolar I disease Diseases 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- NXPOEFGWIXDOJR-UHFFFAOYSA-N 2-(benzenesulfonyl)-7-piperidin-4-yl-1h-indole Chemical compound C=1C=CC=CC=1S(=O)(=O)C(NC1=2)=CC1=CC=CC=2C1CCNCC1 NXPOEFGWIXDOJR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000556 agonist Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
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- 235000020824 obesity Nutrition 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
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- XAPBQLRXHODDJJ-UHFFFAOYSA-N 2-(2-fluorophenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound FC1=CC=CC=C1S(=O)(=O)C1=CC2=CC=CC(N3CCNCC3)=C2N1 XAPBQLRXHODDJJ-UHFFFAOYSA-N 0.000 claims description 3
- ZWXPVTPBDLOVTG-UHFFFAOYSA-N 2-(3-bromophenyl)sulfonyl-7-(4-methylpiperazin-1-yl)-1h-indole Chemical compound C1CN(C)CCN1C1=CC=CC2=C1NC(S(=O)(=O)C=1C=C(Br)C=CC=1)=C2 ZWXPVTPBDLOVTG-UHFFFAOYSA-N 0.000 claims description 3
- VPOGXOWLJJVWDL-UHFFFAOYSA-N 2-(3-bromophenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound BrC1=CC=CC(S(=O)(=O)C=2NC3=C(N4CCNCC4)C=CC=C3C=2)=C1 VPOGXOWLJJVWDL-UHFFFAOYSA-N 0.000 claims description 3
- LXMRZHUWQVPGAY-UHFFFAOYSA-N 2-(benzenesulfonyl)-7-(4-methylpiperazin-1-yl)-1h-indole Chemical compound C1CN(C)CCN1C1=CC=CC2=C1NC(S(=O)(=O)C=1C=CC=CC=1)=C2 LXMRZHUWQVPGAY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- RNIWDFBIEUXJRX-UHFFFAOYSA-N 7-(4-methylpiperazin-1-yl)-2-[2-(trifluoromethyl)phenyl]sulfonyl-1h-indole Chemical compound C1CN(C)CCN1C1=CC=CC2=C1NC(S(=O)(=O)C=1C(=CC=CC=1)C(F)(F)F)=C2 RNIWDFBIEUXJRX-UHFFFAOYSA-N 0.000 claims description 3
- OYAINONYVHDQFT-UHFFFAOYSA-N 7-piperazin-1-yl-2-[2-(trifluoromethyl)phenyl]sulfonyl-1h-indole Chemical compound FC(F)(F)C1=CC=CC=C1S(=O)(=O)C1=CC2=CC=CC(N3CCNCC3)=C2N1 OYAINONYVHDQFT-UHFFFAOYSA-N 0.000 claims description 3
- 208000026139 Memory disease Diseases 0.000 claims description 3
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- 208000025966 Neurological disease Diseases 0.000 claims description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- FYRRWTJHULZSGP-UHFFFAOYSA-N 2-(2,3-dichlorophenyl)sulfonyl-7-(4-methylpiperazin-1-yl)-1h-indole Chemical compound C1CN(C)CCN1C1=CC=CC2=C1NC(S(=O)(=O)C=1C(=C(Cl)C=CC=1)Cl)=C2 FYRRWTJHULZSGP-UHFFFAOYSA-N 0.000 claims description 2
- XYZWTALSHUIGNA-UHFFFAOYSA-N 2-(2,3-dichlorophenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound ClC1=CC=CC(S(=O)(=O)C=2NC3=C(N4CCNCC4)C=CC=C3C=2)=C1Cl XYZWTALSHUIGNA-UHFFFAOYSA-N 0.000 claims description 2
- DOWUJRLLYLCMQG-UHFFFAOYSA-N 2-(benzenesulfonyl)-7-piperazin-1-yl-1h-indole Chemical compound C=1C=CC=CC=1S(=O)(=O)C(NC1=2)=CC1=CC=CC=2N1CCNCC1 DOWUJRLLYLCMQG-UHFFFAOYSA-N 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 8
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006168 tricyclic group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 23
- 239000000651 prodrug Substances 0.000 abstract description 6
- 229940002612 prodrug Drugs 0.000 abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
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- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 8
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Classifications
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- C07—ORGANIC CHEMISTRY
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- 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
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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-
- 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
- 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
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)
- Psychiatry (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41123902P | 2002-09-17 | 2002-09-17 | |
| PCT/EP2003/010101 WO2004026830A1 (en) | 2002-09-17 | 2003-09-11 | 2,7-substituted indoles and their use as 5-ht6 modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20050229A2 true HRP20050229A2 (hr) | 2006-04-30 |
Family
ID=32030655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20050229A HRP20050229A2 (hr) | 2002-09-17 | 2005-03-09 | 2,7-substituirani indoli i njihova uporaba kao modulatora za 5-ht6 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US7247651B2 (ja) |
| EP (1) | EP1587788B9 (ja) |
| JP (1) | JP4327091B2 (ja) |
| KR (1) | KR100686758B1 (ja) |
| CN (1) | CN1314669C (ja) |
| AR (1) | AR041255A1 (ja) |
| AT (1) | ATE362469T1 (ja) |
| AU (1) | AU2003273855B2 (ja) |
| BR (1) | BR0314352A (ja) |
| CA (1) | CA2496765A1 (ja) |
| DE (1) | DE60313895T2 (ja) |
| DK (1) | DK1587788T3 (ja) |
| ES (1) | ES2287518T3 (ja) |
| GT (1) | GT200300199A (ja) |
| HK (1) | HK1083500A1 (ja) |
| HR (1) | HRP20050229A2 (ja) |
| MX (1) | MXPA05002696A (ja) |
| MY (1) | MY138826A (ja) |
| NO (1) | NO20050666L (ja) |
| NZ (1) | NZ537982A (ja) |
| PA (1) | PA8582201A1 (ja) |
| PE (1) | PE20050054A1 (ja) |
| PL (1) | PL376020A1 (ja) |
| PT (1) | PT1587788E (ja) |
| RU (1) | RU2327685C2 (ja) |
| TW (1) | TWI249402B (ja) |
| UY (1) | UY27980A1 (ja) |
| WO (1) | WO2004026830A1 (ja) |
| ZA (1) | ZA200501306B (ja) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2307919T3 (es) | 2002-03-27 | 2008-12-01 | Glaxo Group Limited | Derivados de quinolina y su uso como ligandos de 5-ht6. |
| PT1558582E (pt) | 2003-07-22 | 2006-05-31 | Arena Pharm Inc | Derivados de diaril- e aril-heteroaril-ureia como moduladores do receptor de serotonina 5-ht2a uteis para a profilaxia e tratamento de desordens relacionadas com o mesmo |
| RS50589B (sr) * | 2003-12-23 | 2010-05-07 | H. Lundbeck A/S. | 2-(1h-indolilsulfanil)-benzil amin derivati kao ssri |
| AR052308A1 (es) * | 2004-07-16 | 2007-03-14 | Lundbeck & Co As H | Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto |
| ES2359725T3 (es) | 2004-09-30 | 2011-05-26 | F. Hoffmann-La Roche Ag | Composiciones y métodos para el tratamiento de trastornos cognitivos. |
| US7713954B2 (en) * | 2004-09-30 | 2010-05-11 | Roche Palo Alto Llc | Compositions and methods for treating cognitive disorders |
| WO2006062481A1 (en) * | 2004-12-09 | 2006-06-15 | Biovitrum Ab | New benzofuran derivatives and their use in the treatment of obesity, type ii diabetes and cns disorders . |
| US7629473B2 (en) * | 2005-06-17 | 2009-12-08 | H. Lundbeck A/S | 2-(1H-indolylsulfanyl)-aryl amine derivatives |
| AR054393A1 (es) * | 2005-06-17 | 2007-06-20 | Lundbeck & Co As H | Derivados de benzo(b)furano y benzo(b)tiofeno, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por la inhibicion de la reabsorcion de neurotransmisores de amina biogenicos. |
| BRPI0718776A2 (pt) * | 2006-11-09 | 2013-12-03 | Hoffmann La Roche | Derivados de indol e benzofurano 2-carboxamida |
| EP2254564A1 (en) | 2007-12-12 | 2010-12-01 | Glaxo Group Limited | Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline |
| US20110021538A1 (en) | 2008-04-02 | 2011-01-27 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| US9126946B2 (en) | 2008-10-28 | 2015-09-08 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)urea and crystalline forms related thereto |
| CN103288707B (zh) * | 2013-05-28 | 2015-12-23 | 浙江大学 | 一种3-苯巯基吲哚衍生物的制备方法 |
| US9663498B2 (en) | 2013-12-20 | 2017-05-30 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic compounds and their application in pharmaceuticals |
| WO2016004882A1 (en) | 2014-07-08 | 2016-01-14 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
| RU2017145976A (ru) | 2015-06-12 | 2019-07-15 | Аксовант Сайенсиз Гмбх | Производные диарил- и арилгетероарилмочевины, применимые для профилактики и лечения нарушения поведения во время REM-фазы сна |
| KR20180064373A (ko) | 2015-07-15 | 2018-06-14 | 엑소반트 사이언시즈 게엠베하 | 신경퇴행성 질환과 관련된 환각의 예방 및 치료에 유용한 5-ht2a 세로토닌 수용체의 조절자로서의 다이아릴 및 아릴헤테로아릴 우레아 유도체 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX9700693A (es) | 1994-07-26 | 1997-04-30 | Pfizer | Derivados del 4-indol. |
| US6114532A (en) * | 1998-02-03 | 2000-09-05 | Boehringer Ingelheim Pharma Kg | Bicyclic heterocycles, the preparation thereof, and their use as pharmaceuticals |
| EP0982304B1 (en) | 1998-06-30 | 2002-10-02 | Eli Lilly And Company | Piperidine derivatives having effects on serotonin related systems |
| FR2788772B1 (fr) * | 1999-01-26 | 2001-03-02 | Adir | Nouveaux composes cyano-indoles inhibiteurs de recapture de serotonine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| GB9912413D0 (en) | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
| EP1401813B1 (en) * | 2001-06-07 | 2007-02-07 | F. Hoffman-la Roche AG | New indole derivatives with 5-ht6 receptor affinity |
| CA2450245A1 (en) * | 2001-06-15 | 2002-12-27 | F. Hoffmann-La Roche Ag | 4-piperazinylindole derivatives with 5-ht6 receptor affinity |
| WO2003013510A1 (en) * | 2001-08-07 | 2003-02-20 | Smithkline Beecham P.L.C. | 3-arylsulfonyl-7-piperazinyl- indoles, -benzofurans and -benzothiophenes with 5-ht6 receptor affinity for treating cns disorders |
| JP4754821B2 (ja) | 2002-06-20 | 2011-08-24 | プロキシマゲン・リミテッド | 肥満症、ｉｉ型糖尿病およびｃｎｓ障害の治療に有用な新規化合物 |
-
2003
- 2003-09-11 AT AT03757820T patent/ATE362469T1/de not_active IP Right Cessation
- 2003-09-11 PT PT03757820T patent/PT1587788E/pt unknown
- 2003-09-11 RU RU2005111587/04A patent/RU2327685C2/ru not_active IP Right Cessation
- 2003-09-11 CN CNB03821590XA patent/CN1314669C/zh not_active Expired - Fee Related
- 2003-09-11 BR BR0314352-0A patent/BR0314352A/pt not_active IP Right Cessation
- 2003-09-11 MX MXPA05002696A patent/MXPA05002696A/es active IP Right Grant
- 2003-09-11 DK DK03757820T patent/DK1587788T3/da active
- 2003-09-11 NZ NZ537982A patent/NZ537982A/en unknown
- 2003-09-11 KR KR1020057004480A patent/KR100686758B1/ko not_active IP Right Cessation
- 2003-09-11 EP EP03757820A patent/EP1587788B9/en not_active Expired - Lifetime
- 2003-09-11 AU AU2003273855A patent/AU2003273855B2/en not_active Ceased
- 2003-09-11 JP JP2004537044A patent/JP4327091B2/ja not_active Expired - Fee Related
- 2003-09-11 ES ES03757820T patent/ES2287518T3/es not_active Expired - Lifetime
- 2003-09-11 DE DE60313895T patent/DE60313895T2/de not_active Expired - Lifetime
- 2003-09-11 CA CA002496765A patent/CA2496765A1/en not_active Abandoned
- 2003-09-11 WO PCT/EP2003/010101 patent/WO2004026830A1/en active IP Right Grant
- 2003-09-11 PL PL03376020A patent/PL376020A1/xx not_active Application Discontinuation
- 2003-09-12 TW TW092125197A patent/TWI249402B/zh not_active IP Right Cessation
- 2003-09-12 PE PE2003000929A patent/PE20050054A1/es not_active Application Discontinuation
- 2003-09-12 PA PA20038582201A patent/PA8582201A1/es unknown
- 2003-09-15 UY UY27980A patent/UY27980A1/es not_active Application Discontinuation
- 2003-09-15 AR ARP030103331A patent/AR041255A1/es unknown
- 2003-09-16 GT GT200300199A patent/GT200300199A/es unknown
- 2003-09-16 MY MYPI20033528A patent/MY138826A/en unknown
- 2003-09-16 US US10/663,314 patent/US7247651B2/en not_active Expired - Fee Related
-
2005
- 2005-02-08 NO NO20050666A patent/NO20050666L/no not_active Application Discontinuation
- 2005-02-14 ZA ZA200501306A patent/ZA200501306B/xx unknown
- 2005-03-09 HR HR20050229A patent/HRP20050229A2/hr not_active Application Discontinuation
-
2006
- 2006-03-20 HK HK06103482A patent/HK1083500A1/xx not_active IP Right Cessation
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