JP2006520767A5 - - Google Patents
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- JP2006520767A5 JP2006520767A5 JP2006505152A JP2006505152A JP2006520767A5 JP 2006520767 A5 JP2006520767 A5 JP 2006520767A5 JP 2006505152 A JP2006505152 A JP 2006505152A JP 2006505152 A JP2006505152 A JP 2006505152A JP 2006520767 A5 JP2006520767 A5 JP 2006520767A5
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- Prior art keywords
- pharmaceutical composition
- cancer
- disease
- prevention
- treatment
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 206010053643 Neurodegenerative disease Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 206010001897 Alzheimer's disease Diseases 0.000 claims 1
- 208000004736 B-Cell Leukemia Diseases 0.000 claims 1
- 206010004939 Bipolar I disease Diseases 0.000 claims 1
- 206010004938 Bipolar disease Diseases 0.000 claims 1
- 208000001183 Brain Injury Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 claims 1
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000002154 Non-Small-Cell Lung Carcinoma Diseases 0.000 claims 1
- 108009000071 Non-small cell lung cancer Proteins 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010061536 Parkinson's disease Diseases 0.000 claims 1
- 208000001293 Peripheral Nervous System Disease Diseases 0.000 claims 1
- 206010034606 Peripheral neuropathy Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 206010038932 Retinopathy Diseases 0.000 claims 1
- 208000008513 Spinal Cord Injury Diseases 0.000 claims 1
- 208000000389 T-Cell Leukemia Diseases 0.000 claims 1
- 208000001072 Type 2 Diabetes Mellitus Diseases 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000001154 acute Effects 0.000 claims 1
- 201000004384 alopecia Diseases 0.000 claims 1
- 231100000360 alopecia Toxicity 0.000 claims 1
- 201000001084 cerebrovascular disease Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 230000000472 traumatic Effects 0.000 claims 1
- 201000004810 vascular dementia Diseases 0.000 claims 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N Phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- -1 9- [2- (3-Bromo-phenyl) -2-hydroxy-ethyl] -2,8-dipyridin-4-yl-6,7,8,9-tetrahydro-pyrimido [1,2-a] pyrimidine- 4-on 2-bromoacetophenone Chemical compound 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XWCQSILTDPAWDP-MRVPVSSYSA-N (1S)-2-chloro-1-phenylethanol Chemical compound ClC[C@@H](O)C1=CC=CC=C1 XWCQSILTDPAWDP-MRVPVSSYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- RCYKTASSXMMFJH-UHFFFAOYSA-N 9-(2-hydroxy-2-phenylethyl)-2,8-dipyridin-4-yl-7,8-dihydro-6H-pyrimido[1,2-a]pyrimidin-4-one;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(O)CN1C(C=2C=CN=CC=2)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 RCYKTASSXMMFJH-UHFFFAOYSA-N 0.000 description 1
- IXPJREYPJDQKQH-UHFFFAOYSA-N 9-[2-(3-bromophenyl)-2-oxoethyl]-2,8-dipyridin-4-yl-7,8-dihydro-6H-pyrimido[1,2-a]pyrimidin-4-one;hydrochloride Chemical compound Cl.BrC1=CC=CC(C(=O)CN2C=3N(C(C=C(N=3)C=3C=CN=CC=3)=O)CCC2C=2C=CN=CC=2)=C1 IXPJREYPJDQKQH-UHFFFAOYSA-N 0.000 description 1
Description
実施例15（表1の化合物番号15）
9-[2-(3-ブロモ-フェニル)-2-オキソ-エチル]-2,8-ジピリジン-4-イル-6,7,8,9-テトラヒドロ-ピリミド[1,2-a]ピリミジン-4-オン塩酸塩(1:2)
2-ブロモアセトフェノンを3-ブロモ-(2-ブロモアセトフェノン)に置き換えて、実施例14.3に記載された方法と同様にして、この物質を得た。
Mp : 215-217℃
NMR 1H (200 MHz ; DMSO-d6) : δ(ppm) 8.9 (d, 2H) ; 8.7 (d, 2H); 8.3-7.8 (m, 7H); 7.5 (t, 1H) ; 6.7 (s, 1H) ; 5.75 (d, 1H) ; 5.3 (br s, 1H); 4.7 (d, 1H); 4.5(m,1H) ; 3.1(ddd,1H) ; 2.5(m,2H) .
9-[2-(3-ブロモ-フェニル)-2-オキソ-エチル]-2,8-ジピリジン-4-イル-6,7,8,9-テトラヒドロ-ピリミド[1,2-a]ピリミジン-4-オン塩酸塩(1:2)
2-ブロモアセトフェノンを3-ブロモ-(2-ブロモアセトフェノン)に置き換えて、実施例14.3に記載された方法と同様にして、この物質を得た。
Mp : 215-217℃
NMR 1H (200 MHz ; DMSO-d6) : δ(ppm) 8.9 (d, 2H) ; 8.7 (d, 2H); 8.3-7.8 (m, 7H); 7.5 (t, 1H) ; 6.7 (s, 1H) ; 5.75 (d, 1H) ; 5.3 (br s, 1H); 4.7 (d, 1H); 4.5(m,1H) ; 3.1(ddd,1H) ; 2.5(m,2H) .
実施例16（表1の化合物番号16）
9-(2-ヒドロキシ-2-フェニル-エチル)-2,8-ジピリジン-4-イル-6,7,8,9-テトラヒドロ-ピリミド[1,2-a]ピリミジン-4-オン塩酸塩(1:2)
2-ブロモアセトフェノンを(1-S)-2-クロロ-1-フェニルエタノールに置き換えて、実施例14.3に記載された方法と同様にして、この物質を得た。
Mp : 204-206℃
NMR 1H (200 MHz ; DMSO-d6) : δ(ppm) 9.0 (m, 2H) ; 8.8 (m, 2H); 8.45 (m, 2H); 7.9 (d, 1H) ; 7.8-7.6(m,1H) ; 7.5-7.2(m,5H) ; 6.8 (s, 1H) ; 6.2-5.7 (br d , 1H) ; 5.3- 5.1(m,1H) ; 4.6-4.1(m,2H) ; 3.3(m,2H) ; 2.9(m,1H) ; 2.5-2.2(m,2H) .
9-(2-ヒドロキシ-2-フェニル-エチル)-2,8-ジピリジン-4-イル-6,7,8,9-テトラヒドロ-ピリミド[1,2-a]ピリミジン-4-オン塩酸塩(1:2)
2-ブロモアセトフェノンを(1-S)-2-クロロ-1-フェニルエタノールに置き換えて、実施例14.3に記載された方法と同様にして、この物質を得た。
Mp : 204-206℃
NMR 1H (200 MHz ; DMSO-d6) : δ(ppm) 9.0 (m, 2H) ; 8.8 (m, 2H); 8.45 (m, 2H); 7.9 (d, 1H) ; 7.8-7.6(m,1H) ; 7.5-7.2(m,5H) ; 6.8 (s, 1H) ; 6.2-5.7 (br d , 1H) ; 5.3- 5.1(m,1H) ; 4.6-4.1(m,2H) ; 3.3(m,2H) ; 2.9(m,1H) ; 2.5-2.2(m,2H) .
実施例17（表1の化合物番号17）
9-[2-(3-ブロモ-フェニル)-2-ヒドロキシ-エチル]-2,8-ジピリジン-4-イル-6,7,8,9-テトラヒドロ-ピリミド[1,2-a]ピリミジン-4-オン
2-ブロモアセトフェノンを2-クロロ-1-(3-ブロモ-フェニル)-エタノールに置き換えて、実施例14.3に記載された方法と同様にして、この物質を得た。
Mp : 190-192℃
NMR 1H (200 MHz ; CDCl3) : δ(ppm) 8.8 (d, 2H) ; 8.7 (d, 2H); 7.8 (m, 2H); 7.7-7.4 (m, 2H) ; 7.3(m,2H) ; 7.1(d,2H) ; 6.5 (s, 1H) ; 5.2 (m , 2H) ; 4.8-4.4 (m,3H) ; 3.2 (m,2H) ; 2.3(m,2H) .
9-[2-(3-ブロモ-フェニル)-2-ヒドロキシ-エチル]-2,8-ジピリジン-4-イル-6,7,8,9-テトラヒドロ-ピリミド[1,2-a]ピリミジン-4-オン
2-ブロモアセトフェノンを2-クロロ-1-(3-ブロモ-フェニル)-エタノールに置き換えて、実施例14.3に記載された方法と同様にして、この物質を得た。
Mp : 190-192℃
NMR 1H (200 MHz ; CDCl3) : δ(ppm) 8.8 (d, 2H) ; 8.7 (d, 2H); 7.8 (m, 2H); 7.7-7.4 (m, 2H) ; 7.3(m,2H) ; 7.1(d,2H) ; 6.5 (s, 1H) ; 5.2 (m , 2H) ; 4.8-4.4 (m,3H) ; 3.2 (m,2H) ; 2.3(m,2H) .
実施例18（表1の化合物番号18）
9-[2-(3-フルオロ-フェニル)-2-オキソ-エチル]-2,8-ジピリジン-4-イル-6,7,8,9-テトラヒドロ-ピリミド[1,2-a]ピリミジン-4-オン塩酸塩(1:2)
2-ブロモアセトフェノンを3-フルオロ-(2-ブロモアセトフェノン)に置き換えて、実施例14.3に記載された方法と同様にして、この物質を得た。
Mp : 132-134℃
NMR 1H (200 MHz ; DMSO-d6) : δ(ppm) 8.9 (d, 2H) ; 8.7 (d, 2H); 8.1 (d, 2H); 8.0 (d, 2H) ; 7.9-7.7(m,2H) ; 7.7-7.5(m,2H) ; 6.8 (s, 1H) ; 5.7 (d , 2H) ; 5.3 (br s,1H) ; 4.7(d,1H) ; 4.4(m,1H) ; 3.1(ddd,1H) ; 2.4(m,1H) .
9-[2-(3-フルオロ-フェニル)-2-オキソ-エチル]-2,8-ジピリジン-4-イル-6,7,8,9-テトラヒドロ-ピリミド[1,2-a]ピリミジン-4-オン塩酸塩(1:2)
2-ブロモアセトフェノンを3-フルオロ-(2-ブロモアセトフェノン)に置き換えて、実施例14.3に記載された方法と同様にして、この物質を得た。
Mp : 132-134℃
NMR 1H (200 MHz ; DMSO-d6) : δ(ppm) 8.9 (d, 2H) ; 8.7 (d, 2H); 8.1 (d, 2H); 8.0 (d, 2H) ; 7.9-7.7(m,2H) ; 7.7-7.5(m,2H) ; 6.8 (s, 1H) ; 5.7 (d , 2H) ; 5.3 (br s,1H) ; 4.7(d,1H) ; 4.4(m,1H) ; 3.1(ddd,1H) ; 2.4(m,1H) .
Claims (5)
- GSK3βの異常活性に起因する疾患の予防および／または治療のための、請求項1〜4のいずれか1つに記載の化合物を含む医薬組成物。
- 神経変性疾患の予防および／または治療のための、請求項1〜4のいずれか1つに記載の化合物を含む医薬組成物。
- 神経変性疾患がアルツハイマー病、パーキンソン病、タウ病、血管性痴呆、急性脳卒中、外傷性の障害、脳血管障害、脳損傷、脊髄損傷、末梢神経障害、網膜症または緑内障からなる群から選択される、請求項9に記載の医薬組成物。
- 非インスリン依存性糖尿病、肥満症、躁うつ病、統合失調症、脱毛症または癌の予防および／または治療のための、請求項1〜4のいずれか1つに記載の化合物を含む医薬組成物。
- 癌が乳癌、非小細胞肺癌、甲状腺癌、TもしくはB-細胞白血病またはウイルス誘発性腫瘍である、請求項11に記載の医薬組成物。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03290727A EP1460075A1 (en) | 2003-03-21 | 2003-03-21 | Substituted 8-Pyridinyl-6,7,8,9-Tetrahydropyrimido[1,2-a]Pyrimidin-4-one and 8-Phenyl-6-7,8,9-Tetrahydropyrimido[1,2-a]Pyrimidin-4-one derivatives |
| PCT/EP2004/004014 WO2004082577A2 (en) | 2003-03-21 | 2004-03-19 | 8-SUBSTITUTED-6, 7, 8, 9-TETRAHYDROPYRIMIDO[1,2-a] PYRIMIDIN-4-ONE DERIVATIVES |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006520767A JP2006520767A (ja) | 2006-09-14 |
| JP2006520767A5 true JP2006520767A5 (ja) | 2007-05-10 |
| JP4572195B2 JP4572195B2 (ja) | 2010-10-27 |
Family
ID=32799140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006505152A Expired - Fee Related JP4572195B2 (ja) | 2003-03-21 | 2004-03-19 | ８−置換−６，７，８，９−テトラヒドロピリミド［１，２−ａ］ピリミジン−４−オン誘導体 |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US7247638B2 (ja) |
| EP (2) | EP1460075A1 (ja) |
| JP (1) | JP4572195B2 (ja) |
| KR (1) | KR101070149B1 (ja) |
| CN (1) | CN100358897C (ja) |
| AR (1) | AR043658A1 (ja) |
| AT (1) | ATE452892T1 (ja) |
| AU (1) | AU2004222596B2 (ja) |
| BR (1) | BRPI0408591A (ja) |
| CA (1) | CA2518299C (ja) |
| CY (1) | CY1109890T1 (ja) |
| DE (1) | DE602004024770D1 (ja) |
| DK (1) | DK1608654T3 (ja) |
| EA (1) | EA009197B1 (ja) |
| ES (1) | ES2338325T3 (ja) |
| HK (1) | HK1086012A1 (ja) |
| IL (1) | IL170680A (ja) |
| MX (1) | MXPA05010158A (ja) |
| NO (1) | NO20054330L (ja) |
| NZ (1) | NZ542380A (ja) |
| PL (1) | PL1608654T3 (ja) |
| PT (1) | PT1608654E (ja) |
| SI (1) | SI1608654T1 (ja) |
| TW (1) | TWI330186B (ja) |
| WO (1) | WO2004082577A2 (ja) |
| ZA (1) | ZA200507487B (ja) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1460075A1 (en) * | 2003-03-21 | 2004-09-22 | Sanofi-Synthelabo | Substituted 8-Pyridinyl-6,7,8,9-Tetrahydropyrimido[1,2-a]Pyrimidin-4-one and 8-Phenyl-6-7,8,9-Tetrahydropyrimido[1,2-a]Pyrimidin-4-one derivatives |
| RU2009108280A (ru) | 2006-08-08 | 2010-09-20 | Санофи-Авентис (Fr) | Ариламиноарилалкилзамещенные имидазолидин-2,4-дионы, способы их получения, содержащие эти соединения лекарственные средства и их применение |
| EP1939187A1 (en) * | 2006-12-20 | 2008-07-02 | Sanofi-Aventis | Substituted heteroaryl pyridopyrimidone derivatives |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| AR072707A1 (es) | 2008-07-09 | 2010-09-15 | Sanofi Aventis | Compuestos heterociclicos, procesos para su preparacion, medicamentos que comprenden estos compuestos y el uso de los mismos |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| EP2470552B1 (en) | 2009-08-26 | 2013-11-13 | Sanofi | Novel crystalline heteroaromatic fluoroglycoside hydrates, pharmaceuticals comprising these compounds and their use |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| US8846666B2 (en) | 2011-03-08 | 2014-09-30 | Sanofi | Oxathiazine derivatives which are substituted with benzyl or heteromethylene groups, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| EP2683703B1 (de) | 2011-03-08 | 2015-05-27 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683700B1 (de) | 2011-03-08 | 2015-02-18 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| AU2020353055B2 (en) | 2019-09-26 | 2024-03-07 | Gilead Sciences, Inc. | Antiviral pyrazolopyridinone compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1136482A1 (en) * | 2000-03-23 | 2001-09-26 | Sanofi-Synthelabo | 2-Amino-3-(alkyl)-pyrimidone derivatives as GSK3beta inhibitors |
| JP2001270884A (ja) * | 2000-03-23 | 2001-10-02 | Mitsubishi-Tokyo Pharmaceuticals Inc | ピリミドン誘導体 |
| EP1315731B1 (en) * | 2000-09-01 | 2004-06-16 | Sanofi-Synthelabo | 2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1h)one derivatives |
| EP1184383A1 (en) * | 2000-09-01 | 2002-03-06 | Sanofi-Synthelabo | 9-[Alkyl], 9-[(heteroaryl)alkyl] and 9-[(aryl)alkyl]-2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one derivatives |
| EP1460075A1 (en) * | 2003-03-21 | 2004-09-22 | Sanofi-Synthelabo | Substituted 8-Pyridinyl-6,7,8,9-Tetrahydropyrimido[1,2-a]Pyrimidin-4-one and 8-Phenyl-6-7,8,9-Tetrahydropyrimido[1,2-a]Pyrimidin-4-one derivatives |
-
2003
- 2003-03-21 EP EP03290727A patent/EP1460075A1/en not_active Withdrawn
-
2004
- 2004-03-17 TW TW093107079A patent/TWI330186B/zh not_active IP Right Cessation
- 2004-03-19 MX MXPA05010158A patent/MXPA05010158A/es active IP Right Grant
- 2004-03-19 WO PCT/EP2004/004014 patent/WO2004082577A2/en active Application Filing
- 2004-03-19 ES ES04721906T patent/ES2338325T3/es not_active Expired - Lifetime
- 2004-03-19 AR ARP040100917A patent/AR043658A1/es unknown
- 2004-03-19 EA EA200501315A patent/EA009197B1/ru not_active IP Right Cessation
- 2004-03-19 ZA ZA200507487A patent/ZA200507487B/en unknown
- 2004-03-19 EP EP04721906A patent/EP1608654B1/en not_active Expired - Lifetime
- 2004-03-19 DK DK04721906.8T patent/DK1608654T3/da active
- 2004-03-19 KR KR1020057017572A patent/KR101070149B1/ko not_active IP Right Cessation
- 2004-03-19 PT PT04721906T patent/PT1608654E/pt unknown
- 2004-03-19 SI SI200431367T patent/SI1608654T1/sl unknown
- 2004-03-19 BR BRPI0408591-4A patent/BRPI0408591A/pt not_active IP Right Cessation
- 2004-03-19 PL PL04721906T patent/PL1608654T3/pl unknown
- 2004-03-19 AT AT04721906T patent/ATE452892T1/de active
- 2004-03-19 NZ NZ542380A patent/NZ542380A/en not_active IP Right Cessation
- 2004-03-19 CN CNB2004800120116A patent/CN100358897C/zh not_active Expired - Fee Related
- 2004-03-19 JP JP2006505152A patent/JP4572195B2/ja not_active Expired - Fee Related
- 2004-03-19 CA CA2518299A patent/CA2518299C/en not_active Expired - Fee Related
- 2004-03-19 AU AU2004222596A patent/AU2004222596B2/en not_active Ceased
- 2004-03-19 DE DE602004024770T patent/DE602004024770D1/de not_active Expired - Lifetime
-
2005
- 2005-09-05 IL IL170680A patent/IL170680A/en not_active IP Right Cessation
- 2005-09-13 US US11/225,218 patent/US7247638B2/en not_active Expired - Fee Related
- 2005-09-20 NO NO20054330A patent/NO20054330L/no not_active Application Discontinuation
-
2006
- 2006-06-24 HK HK06108336A patent/HK1086012A1/xx not_active IP Right Cessation
-
2007
- 2007-06-18 US US11/764,374 patent/US8093256B2/en not_active Expired - Fee Related
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2010
- 2010-03-09 CY CY20101100221T patent/CY1109890T1/el unknown
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