JP2007505922A5 - - Google Patents
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- Publication number
- JP2007505922A5 JP2007505922A5 JP2006527059A JP2006527059A JP2007505922A5 JP 2007505922 A5 JP2007505922 A5 JP 2007505922A5 JP 2006527059 A JP2006527059 A JP 2006527059A JP 2006527059 A JP2006527059 A JP 2006527059A JP 2007505922 A5 JP2007505922 A5 JP 2007505922A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- amino
- acyloxy
- alkoxy
- 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.)
- Granted
Links
- 125000004423 acyloxy group Chemical group 0.000 claims 51
- 125000002252 acyl group Chemical group 0.000 claims 46
- 125000000217 alkyl group Chemical group 0.000 claims 44
- 150000002431 hydrogen Chemical class 0.000 claims 44
- 229910052739 hydrogen Inorganic materials 0.000 claims 44
- 239000001257 hydrogen Substances 0.000 claims 44
- 150000001875 compounds Chemical class 0.000 claims 41
- 125000000547 substituted alkyl group Chemical group 0.000 claims 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 40
- 229910052717 sulfur Inorganic materials 0.000 claims 31
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 30
- 239000011593 sulfur Substances 0.000 claims 30
- -1 Amino, substituted amino Chemical group 0.000 claims 29
- 229910052736 halogen Inorganic materials 0.000 claims 26
- 150000002367 halogens Chemical class 0.000 claims 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 26
- 125000003545 alkoxy group Chemical group 0.000 claims 25
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 25
- 125000003118 aryl group Chemical group 0.000 claims 24
- 125000003342 alkenyl group Chemical group 0.000 claims 23
- 125000000304 alkynyl group Chemical group 0.000 claims 23
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 23
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 23
- 125000003107 substituted aryl group Chemical group 0.000 claims 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 17
- 229910052760 oxygen Inorganic materials 0.000 claims 17
- 239000001301 oxygen Substances 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 12
- ZNXFEZJRALUZGZ-UHFFFAOYSA-N 2-(2-oxo-6-sulfanylidenepiperidin-3-yl)-3-sulfanylideneisoindol-1-one Chemical compound S=C1C2=CC=CC=C2C(=O)N1C1CCC(=S)NC1=O ZNXFEZJRALUZGZ-UHFFFAOYSA-N 0.000 claims 8
- HPZIYTPFXVRSEL-UHFFFAOYSA-N 2-[2,6-bis(sulfanylidene)piperidin-3-yl]-3-sulfanylideneisoindol-1-one Chemical compound S=C1C2=CC=CC=C2C(=O)N1C1CCC(=S)NC1=S HPZIYTPFXVRSEL-UHFFFAOYSA-N 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- YIVPAGQZXIJWBX-UHFFFAOYSA-N 2-[2,6-bis(sulfanylidene)piperidin-3-yl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=S)NC1=S YIVPAGQZXIJWBX-UHFFFAOYSA-N 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- GXIXKSMAOXPPGZ-UHFFFAOYSA-N 2-cyclohex-3-en-1-ylisoindole-1,3-dithione Chemical compound S=C1C2=CC=CC=C2C(=S)N1C1CCC=CC1 GXIXKSMAOXPPGZ-UHFFFAOYSA-N 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims 3
- QFSZJXRBCXUCMD-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)pyrrolo[3,4-c]pyridine-1,3-dione Chemical compound O=C1C2=CN=CC=C2C(=O)N1C1CCC(=O)NC1=O QFSZJXRBCXUCMD-UHFFFAOYSA-N 0.000 claims 3
- FNFLWRDNFCUNQT-UHFFFAOYSA-N 2-(2-oxo-6-sulfanylidenepiperidin-3-yl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=S)NC1=O FNFLWRDNFCUNQT-UHFFFAOYSA-N 0.000 claims 3
- OTDLWDKISPNCQW-UHFFFAOYSA-N 2-[2,6-dioxo-1-(2-phenylethyl)piperidin-3-yl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(C1=O)CCC(=O)N1CCC1=CC=CC=C1 OTDLWDKISPNCQW-UHFFFAOYSA-N 0.000 claims 3
- VDXNOKQEYGTPGZ-UHFFFAOYSA-N 2-cyclohex-3-en-1-yl-3-sulfanylideneisoindol-1-one Chemical compound S=C1C2=CC=CC=C2C(=O)N1C1CCC=CC1 VDXNOKQEYGTPGZ-UHFFFAOYSA-N 0.000 claims 3
- FVOWJCUUOBMLPE-UHFFFAOYSA-N 3-(1-oxo-3-sulfanylideneisoindol-2-yl)piperidine-2,6-dione Chemical compound S=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O FVOWJCUUOBMLPE-UHFFFAOYSA-N 0.000 claims 3
- QOVMQFRFRYWHFV-UHFFFAOYSA-N 3-n-(2,6-dioxopiperidin-3-yl)naphthalene-2,3-dicarboxamide Chemical compound NC(=O)C1=CC2=CC=CC=C2C=C1C(=O)NC1CCC(=O)NC1=O QOVMQFRFRYWHFV-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- KZVNYZQKCAGNHL-UHFFFAOYSA-N [2-[(2,6-dioxopiperidin-3-yl)carbamoyl]phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NC1C(=O)NC(=O)CC1 KZVNYZQKCAGNHL-UHFFFAOYSA-N 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- DZVUHHROHSPUED-UHFFFAOYSA-N dimethyl 2-(1-oxo-3-sulfanylideneisoindol-2-yl)pentanedioate Chemical compound C1=CC=C2C(=S)N(C(CCC(=O)OC)C(=O)OC)C(=O)C2=C1 DZVUHHROHSPUED-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims 2
- DNYJMSSHPMBPGB-UHFFFAOYSA-N 2-(1-oxo-3-sulfanylideneisoindol-2-yl)pentanedioic acid Chemical compound C1=CC=C2C(=S)N(C(CCC(=O)O)C(O)=O)C(=O)C2=C1 DNYJMSSHPMBPGB-UHFFFAOYSA-N 0.000 claims 2
- IOLMYDDAHXTLLS-UHFFFAOYSA-N 3-aminopiperidine-2,6-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC1CCC(=O)NC1=O IOLMYDDAHXTLLS-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000034038 Pathologic Neovascularization Diseases 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- NPWMTBZSRRLQNJ-UHFFFAOYSA-N pyroglutamine Chemical compound NC1CCC(=O)NC1=O NPWMTBZSRRLQNJ-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 229960003433 thalidomide Drugs 0.000 claims 2
- VVNYDCGZZSTUBC-LURJTMIESA-N (2s)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCC(N)=O VVNYDCGZZSTUBC-LURJTMIESA-N 0.000 claims 1
- PAMWIQZMLLUFBP-UHFFFAOYSA-N 1-aminopiperidine-2,6-dione Chemical compound NN1C(=O)CCCC1=O PAMWIQZMLLUFBP-UHFFFAOYSA-N 0.000 claims 1
- MBYLNRRTUYQZAW-UHFFFAOYSA-N 2-(2-phenylethyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC1=CC=CC=C1 MBYLNRRTUYQZAW-UHFFFAOYSA-N 0.000 claims 1
- GWSCZWXCPVOCOC-UHFFFAOYSA-N 2-benzyl-3-benzyliminoisoindol-1-one Chemical compound C=1C=CC=CC=1CN=C1C2=CC=CC=C2C(=O)N1CC1=CC=CC=C1 GWSCZWXCPVOCOC-UHFFFAOYSA-N 0.000 claims 1
- ZIKDETHPMRZUKO-UHFFFAOYSA-N 2-cyclohex-3-en-1-ylisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC=CC1 ZIKDETHPMRZUKO-UHFFFAOYSA-N 0.000 claims 1
- QFODIVSHCUILDZ-UHFFFAOYSA-N 3-(3-oxoisoindol-1-ylidene)piperidine-2,6-dione Chemical compound C12=CC=CC=C2C(=O)NC1=C1CCC(=O)NC1=O QFODIVSHCUILDZ-UHFFFAOYSA-N 0.000 claims 1
- JTZRBPSHQZOCBU-UHFFFAOYSA-N 6-sulfanylidenepiperidin-2-one Chemical compound O=C1CCCC(=S)N1 JTZRBPSHQZOCBU-UHFFFAOYSA-N 0.000 claims 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-L glutarate(2-) Chemical compound [O-]C(=O)CCCC([O-])=O JFCQEDHGNNZCLN-UHFFFAOYSA-L 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- CMTSCLKCQBPLSH-UHFFFAOYSA-N isoindole-1,3-dithione Chemical compound C1=CC=C2C(=S)NC(=S)C2=C1 CMTSCLKCQBPLSH-UHFFFAOYSA-N 0.000 claims 1
- ABLCLJKCIOWZAQ-UHFFFAOYSA-N piperidine-2,3,6-trione Chemical compound O=C1CCC(=O)NC1=O ABLCLJKCIOWZAQ-UHFFFAOYSA-N 0.000 claims 1
- ICJTYWLQSDUPRA-UHFFFAOYSA-N piperidine-2,6-dithione Chemical compound S=C1CCCC(=S)N1 ICJTYWLQSDUPRA-UHFFFAOYSA-N 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 0 CC(C)C(CC(*)C(*)C1=C(C*=C2*)[N+]([O-])=O)C1=C2O Chemical compound CC(C)C(CC(*)C(*)C1=C(C*=C2*)[N+]([O-])=O)C1=C2O 0.000 description 6
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50472403P | 2003-09-17 | 2003-09-17 | |
| US60/504,724 | 2003-09-17 | ||
| PCT/US2004/030506 WO2005028436A2 (en) | 2003-09-17 | 2004-09-17 | Thalidomide analogs as tnf-alpha modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007505922A JP2007505922A (ja) | 2007-03-15 |
| JP2007505922A5 true JP2007505922A5 (enExample) | 2007-10-11 |
| JP4943845B2 JP4943845B2 (ja) | 2012-05-30 |
Family
ID=34375538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006527059A Expired - Fee Related JP4943845B2 (ja) | 2003-09-17 | 2004-09-17 | サリドマイド類似体 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US7973057B2 (enExample) |
| EP (1) | EP1663223B1 (enExample) |
| JP (1) | JP4943845B2 (enExample) |
| CN (1) | CN1867331B (enExample) |
| AU (1) | AU2004274474B2 (enExample) |
| BR (1) | BRPI0414497A (enExample) |
| CA (2) | CA2538864C (enExample) |
| SG (1) | SG133603A1 (enExample) |
| WO (1) | WO2005028436A2 (enExample) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2929331B2 (ja) * | 1990-07-18 | 1999-08-03 | 丸善石油化学株式会社 | トラクションドライブ用流体 |
| NZ552397A (en) | 2004-07-15 | 2011-04-29 | Amr Technology Inc | Aryl-and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| CN100383139C (zh) | 2005-04-07 | 2008-04-23 | 天津和美生物技术有限公司 | 可抑制细胞释放肿瘤坏死因子的哌啶-2，6-二酮衍生物 |
| CN1939922B (zh) * | 2005-09-27 | 2010-10-13 | 天津和美生物技术有限公司 | 可抑制细胞释放肿瘤坏死因子的5H-噻吩[3，4-c]吡咯-4，6-二酮衍生物 |
| US20080064876A1 (en) * | 2006-05-16 | 2008-03-13 | Muller George W | Process for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione |
| CL2007002513A1 (es) * | 2006-08-30 | 2008-04-04 | Celgene Corp Soc Organizada Ba | Compuestos derivados de isoindolina sustituidos, compuestos intermediarios; composicion farmaceutica; y uso en el tratamiento y prevencion de enfermedades tales como cancer, dolor, degeneracion macular, entre otras. |
| US8877780B2 (en) | 2006-08-30 | 2014-11-04 | Celgene Corporation | 5-substituted isoindoline compounds |
| AU2013260742B2 (en) * | 2007-03-20 | 2016-06-16 | Celgene Corporation | 4'-o-substituted isoindoline derivatives and compositions comprising and methods of using the same |
| MX2009010082A (es) * | 2007-03-20 | 2009-10-19 | Celgene Corp | Derivados y composiciones que comprenden isoindolina 4'-o-sustituida y metodos para utilizar la misma. |
| US7723301B2 (en) * | 2007-08-29 | 2010-05-25 | The Board Of Trustees Of The University Of Arkansas | Pharmaceutical compositions comprising an anti-teratogenic compound and applications of the same |
| US20090298882A1 (en) * | 2008-05-13 | 2009-12-03 | Muller George W | Thioxoisoindoline compounds and compositions comprising and methods of using the same |
| US9156812B2 (en) | 2008-06-04 | 2015-10-13 | Bristol-Myers Squibb Company | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
| AU2010247735B2 (en) | 2009-05-12 | 2015-07-16 | Albany Molecular Research, Inc. | Crystalline forms of (S)-7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)- 1,2,3,4-tetrahydroisoquinoline and use thereof |
| AU2010247763B2 (en) * | 2009-05-12 | 2015-12-24 | Albany Molecular Research, Inc. | 7-([1,2,4,]triazolo[1,5,-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4- tetrahydroisoquinoline and use thereof |
| WO2010132437A1 (en) | 2009-05-12 | 2010-11-18 | Albany Molecular Research, Inc. | Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof |
| PL3202460T3 (pl) | 2010-02-11 | 2019-12-31 | Celgene Corporation | Pochodne arylometoksyizoindoliny i zawierające je kompozycje oraz sposoby ich zastosowania |
| WO2011160042A2 (en) * | 2010-06-18 | 2011-12-22 | Makoto Life Sciences, Inc. | Prpk-tprkb modulators and uses thereof |
| US8927725B2 (en) | 2011-12-02 | 2015-01-06 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Thio compounds |
| JP2015500001A (ja) | 2011-12-14 | 2015-01-05 | 大鵬薬品工業株式会社 | 組換えｐｒｐｋ−ｔｐｒｋｂ及びその使用 |
| US9383644B2 (en) | 2014-09-18 | 2016-07-05 | Heraeus Precious Metals North America Daychem LLC | Sulfonic acid derivative compounds as photoacid generators in resist applications |
| NZ731789A (en) | 2014-10-30 | 2019-04-26 | Kangpu Biopharmaceuticals Ltd | Isoindoline derivative, intermediate, preparation method, pharmaceutical composition and use thereof |
| US9477150B2 (en) | 2015-03-13 | 2016-10-25 | Heraeus Precious Metals North America Daychem LLC | Sulfonic acid derivative compounds as photoacid generators in resist applications |
| EP3319603B1 (en) * | 2015-07-08 | 2021-11-17 | Gilrose Pharmaceuticals, LLC | Use of methylphenidate for the treatment of gait and limb impairment secondary to pre-frontal cortex processing disorder |
| AU2016330967B2 (en) | 2015-09-30 | 2021-03-25 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Thalidomide analogs and methods of use |
| BR112018068906A2 (pt) | 2016-03-16 | 2019-01-22 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | composição, método, método de redução de risco, prevenção ou tratamento de um indivíduo que tem uma doença ou distúrbio autoimune, método de indução de degradação de uma proteína-alvo numa célula, método para reduzir o risco, prevenir ou tratar um estado da doença ou afecção num paciente em que a atividade proteica desregulada é responsável pelo referido estado da doença ou afecção, método para reduzir o risco, prevenir ou tratar câncer num indivíduo e método de tratamento de uma doença ou distúrbio genético num indivíduo |
| WO2018095377A1 (zh) * | 2016-11-24 | 2018-05-31 | 天津和美生物技术有限公司 | 哌啶-2,6-二酮衍生物以及溃疡性结肠炎的治疗 |
| AU2018351050B2 (en) | 2017-10-18 | 2025-09-18 | Novartis Ag | Compositions and methods for selective protein degradation |
| CN112512589A (zh) | 2018-07-11 | 2021-03-16 | H·李·莫菲特癌症中心研究有限公司 | 二聚体免疫调节化合物对抗基于cereblon的机制 |
| US11324731B2 (en) | 2018-09-13 | 2022-05-10 | City Of Hope | TXNIP-TRX complex inhibitors and methods of using the same |
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| AU2021226514B2 (en) * | 2020-02-25 | 2023-10-19 | Shanghaitech University | Glutarimide skeleton-based compounds and application thereof |
| KR102943446B1 (ko) * | 2020-10-26 | 2026-04-01 | 주식회사 아이비스바이오 | 포말리도마이드로부터 3,6'-디티오포말리도마이드를 선택적으로 합성하는 방법 |
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-
2004
- 2004-09-17 US US10/572,485 patent/US7973057B2/en not_active Expired - Fee Related
- 2004-09-17 JP JP2006527059A patent/JP4943845B2/ja not_active Expired - Fee Related
- 2004-09-17 AU AU2004274474A patent/AU2004274474B2/en not_active Ceased
- 2004-09-17 CA CA2538864A patent/CA2538864C/en not_active Expired - Fee Related
- 2004-09-17 WO PCT/US2004/030506 patent/WO2005028436A2/en not_active Ceased
- 2004-09-17 EP EP04784385.9A patent/EP1663223B1/en not_active Expired - Lifetime
- 2004-09-17 BR BRPI0414497-0A patent/BRPI0414497A/pt not_active IP Right Cessation
- 2004-09-17 CA CA2808646A patent/CA2808646C/en not_active Expired - Fee Related
- 2004-09-17 SG SG200704530-5A patent/SG133603A1/en unknown
- 2004-09-17 CN CN2004800268113A patent/CN1867331B/zh not_active Expired - Fee Related
-
2011
- 2011-06-03 US US13/153,355 patent/US8546430B2/en not_active Expired - Fee Related
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