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) |
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|---|---|---|---|---|
| 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 |
| US20060063766A1 (en) | 2004-07-15 | 2006-03-23 | Molino Bruce F | Use of aryl- and heteroaryl-substituted tetrahydroisoquinolines 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 |
| US8877780B2 (en) | 2006-08-30 | 2014-11-04 | Celgene Corporation | 5-substituted isoindoline compounds |
| MX2009001989A (es) * | 2006-08-30 | 2009-03-09 | Celgene Corp | Compuestos de isoindolina 5-substituidos. |
| AU2013260742B2 (en) * | 2007-03-20 | 2016-06-16 | Celgene Corporation | 4'-o-substituted isoindoline derivatives and compositions comprising and methods of using the same |
| US8153659B2 (en) * | 2007-03-20 | 2012-04-10 | Celgene Corporation | 4′-O-substituted isoindoline derivatives and compositions comprising and methods of using the same |
| 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 |
| JP2012526823A (ja) | 2009-05-12 | 2012-11-01 | アルバニー モレキュラー リサーチ， インコーポレイテッド | アリール、ヘテロアリール、および複素環置換テトラヒドロイソキノリンならびにそれらの使用 |
| PE20120373A1 (es) * | 2009-05-12 | 2012-05-17 | Albany Molecular Res Inc | 7-([1,2,4]triazolo[1,5-a]piridin-6-il)-4-(3,4-diclorofenil)-1,2,3,4-tetrahidroisoquinolina |
| US8815894B2 (en) | 2009-05-12 | 2014-08-26 | Bristol-Myers Squibb Company | 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 |
| SI3202460T1 (sl) * | 2010-02-11 | 2019-10-30 | Celgene Corp | Arilmetoksi izoindolin derivati in sestavki, ki jih obsegajo in metode za uporabo le-teh |
| US9193989B2 (en) | 2010-06-18 | 2015-11-24 | Taiho Pharmaceutical Co., Ltd. | 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 |
| WO2013089278A1 (en) | 2011-12-14 | 2013-06-20 | Taiho Pharmaceutical Co., Ltd. | Recombinant prpk-tprkb and uses thereof |
| 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 |
| WO2016065980A1 (zh) | 2014-10-30 | 2016-05-06 | 康朴生物医药技术（上海）有限公司 | 异吲哚啉衍生物、其中间体、制备方法、药物组合物及应用 |
| 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 |
| JP6930969B2 (ja) * | 2015-07-08 | 2021-09-01 | ギルローズ ファーマシューティカルズ，リミティド ライアビリティ カンパニー | 前頭前皮質プロセシング疾患、歩行及び四肢障害の治療 |
| 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 |
| EP3429996A4 (en) * | 2016-03-16 | 2020-02-12 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | SMALL MOLECULES AGAINST CEREBLON TO IMPROVE THE FUNCTION OF EFFECTOR T CELLS |
| AU2017366514B2 (en) * | 2016-11-24 | 2021-01-21 | Ganzhou Hemay Pharmaceutical, Co., Ltd | Piperidine-2,6-dione derivative and treatment for ulcerative colitis |
| KR20200086278A (ko) | 2017-10-18 | 2020-07-16 | 노파르티스 아게 | 선택적 단백질 분해를 위한 조성물 및 방법 |
| SG11202012464WA (en) | 2018-07-11 | 2021-01-28 | H Lee Moffitt Cancer Center And Research Institute Inc | Dimeric immuno-modulatory compounds against cereblon-based mechanisms |
| 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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| CN111601789A (zh) * | 2018-12-20 | 2020-08-28 | 江苏凯迪恩医药科技有限公司 | 一种含氮杂环化合物、其制备方法及应用 |
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| CN114641337A (zh) * | 2019-08-27 | 2022-06-17 | 密歇根大学董事会 | Cereblon e3连接酶抑制剂 |
| KR102783667B1 (ko) | 2019-10-24 | 2025-03-21 | 삼성전자 주식회사 | 전자 장치 및 그의 디스플레이 동작 제어 방법 |
| US12441707B2 (en) | 2019-12-30 | 2025-10-14 | Tyra Biosciences, Inc. | Indazole compounds |
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| KR20220055171A (ko) * | 2020-10-26 | 2022-05-03 | 주식회사 아이비스바이오 | 포말리도마이드로부터 3,6'-디티오포말리도마이드를 선택적으로 합성하는 방법 |
| US20240166647A1 (en) * | 2021-03-03 | 2024-05-23 | The Regents Of The University Of Michigan | Cereblon Ligands |
| EP4484418A1 (en) * | 2022-02-25 | 2025-01-01 | Aevis Bio, Inc. | Use of novel pomalidomide derivative for treating brain disease |
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-
2004
- 2004-09-17 CA CA2538864A patent/CA2538864C/en not_active Expired - Fee Related
- 2004-09-17 SG SG200704530-5A patent/SG133603A1/en unknown
- 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 WO PCT/US2004/030506 patent/WO2005028436A2/en not_active Ceased
- 2004-09-17 CN CN2004800268113A patent/CN1867331B/zh not_active Expired - Fee Related
- 2004-09-17 CA CA2808646A patent/CA2808646C/en not_active Expired - Fee Related
- 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 US US10/572,485 patent/US7973057B2/en 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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