JP2009532379A5 - - Google Patents
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- Publication number
- JP2009532379A5 JP2009532379A5 JP2009503258A JP2009503258A JP2009532379A5 JP 2009532379 A5 JP2009532379 A5 JP 2009532379A5 JP 2009503258 A JP2009503258 A JP 2009503258A JP 2009503258 A JP2009503258 A JP 2009503258A JP 2009532379 A5 JP2009532379 A5 JP 2009532379A5
- Authority
- JP
- Japan
- Prior art keywords
- benzyloxy
- thiadiazolidin
- title compound
- trioxo
- dioxo
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 description 13
- 238000000034 method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- -1 3-benzyloxy-4-nitrobenzyl Chemical group 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XSUCKWHLLFTGQF-VQHVLOKHSA-N (e)-3-[3-phenylmethoxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]prop-2-enoic acid Chemical compound C=1C=CC=CC=1COC1=CC(/C=C/C(=O)O)=CC=C1N1CC(=O)NS1(=O)=O XSUCKWHLLFTGQF-VQHVLOKHSA-N 0.000 description 2
- UMPCRQWRRIQOMZ-UHFFFAOYSA-N 5-(4-iodo-2-phenylmethoxyphenyl)-1,1-dioxo-2-(2-trimethylsilylethyl)-1,2,5-thiadiazolidin-3-one Chemical compound O=S1(=O)N(CC[Si](C)(C)C)C(=O)CN1C1=CC=C(I)C=C1OCC1=CC=CC=C1 UMPCRQWRRIQOMZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FAJOMXOMVWXMTD-SECBINFHSA-N (3r)-3-(iodomethyl)-2,3-dihydro-2-benzazepin-1-one Chemical compound C1=C[C@H](CI)NC(=O)C2=CC=CC=C21 FAJOMXOMVWXMTD-SECBINFHSA-N 0.000 description 1
- IDDBUTYTSVGOFC-QMMMGPOBSA-N (3s)-3-(iodomethyl)-3,4-dihydro-2h-isoquinolin-1-one Chemical compound C1=CC=C2C(=O)N[C@H](CI)CC2=C1 IDDBUTYTSVGOFC-QMMMGPOBSA-N 0.000 description 1
- NQHPTSCAFOPVMO-UHFFFAOYSA-N 1,1-dioxo-5-[4-[(5-oxo-6,7-dihydrobenzo[d][2]benzazepin-7-yl)methyl]-2-phenylmethoxyphenyl]-2-(2-trimethylsilylethyl)-1,2,5-thiadiazolidin-3-one Chemical compound O=S1(=O)N(CC[Si](C)(C)C)C(=O)CN1C(C(=C1)OCC=2C=CC=CC=2)=CC=C1CC1C2=CC=CC=C2C2=CC=CC=C2C(=O)N1 NQHPTSCAFOPVMO-UHFFFAOYSA-N 0.000 description 1
- HOOUDUZIDKKFDE-RUZDIDTESA-N 1,1-dioxo-5-[4-[[(3r)-1-oxo-3,4-dihydro-2h-isoquinolin-3-yl]methyl]-2-phenylmethoxyphenyl]-2-(2-trimethylsilylethyl)-1,2,5-thiadiazolidin-3-one Chemical compound O=S1(=O)N(CC[Si](C)(C)C)C(=O)CN1C(C(=C1)OCC=2C=CC=CC=2)=CC=C1C[C@H]1NC(=O)C2=CC=CC=C2C1 HOOUDUZIDKKFDE-RUZDIDTESA-N 0.000 description 1
- OWPDXBAPGBONBX-AREMUKBSSA-N 1,1-dioxo-5-[4-[[(3s)-1-oxo-2,3-dihydro-2-benzazepin-3-yl]methyl]-2-phenylmethoxyphenyl]-2-(2-trimethylsilylethyl)-1,2,5-thiadiazolidin-3-one Chemical compound O=S1(=O)N(CC[Si](C)(C)C)C(=O)CN1C(C(=C1)OCC=2C=CC=CC=2)=CC=C1C[C@H]1C=CC2=CC=CC=C2C(=O)N1 OWPDXBAPGBONBX-AREMUKBSSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- CXNDUFLGBNIOJV-UHFFFAOYSA-N 1-[(4-nitro-3-phenylmethoxyphenyl)methyl]-3,4-dihydro-1h-naphthalen-2-one Chemical compound [O-][N+](=O)C1=CC=C(CC2C3=CC=CC=C3CCC2=O)C=C1OCC1=CC=CC=C1 CXNDUFLGBNIOJV-UHFFFAOYSA-N 0.000 description 1
- MLBCDQHOBLVBQD-UHFFFAOYSA-N 2,4-Dimethyl-5-vinylthiazole Chemical compound CC1=NC(C)=C(C=C)S1 MLBCDQHOBLVBQD-UHFFFAOYSA-N 0.000 description 1
- XAHWXDLKIYXDCK-UHFFFAOYSA-N 2,4-dimethyl-1,3-thiazole-5-carbaldehyde Chemical compound CC1=NC(C)=C(C=O)S1 XAHWXDLKIYXDCK-UHFFFAOYSA-N 0.000 description 1
- OYWIUAJLASMCBP-UHFFFAOYSA-N 4-(2-methylsulfonyl-3-phenylmethoxyphenoxy)butan-1-amine Chemical compound CS(=O)(=O)C1=C(OCCCCN)C=CC=C1OCC1=CC=CC=C1 OYWIUAJLASMCBP-UHFFFAOYSA-N 0.000 description 1
- HFHUKDDAGCVZKT-UHFFFAOYSA-N 4-(bromomethyl)-1-nitro-2-phenylmethoxybenzene Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1OCC1=CC=CC=C1 HFHUKDDAGCVZKT-UHFFFAOYSA-N 0.000 description 1
- RBHBMCRKBGEHET-UHFFFAOYSA-N 4-nitro-3-phenylmethoxybenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1OCC1=CC=CC=C1 RBHBMCRKBGEHET-UHFFFAOYSA-N 0.000 description 1
- OFMYVDPBZARMHM-UHFFFAOYSA-N 5-[2-hydroxy-4-(3-oxo-2,3-diphenylpropyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 OFMYVDPBZARMHM-UHFFFAOYSA-N 0.000 description 1
- KBSSPJQTFBORLB-UHFFFAOYSA-N 5-[4-(2-benzoylpentyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C=1C=CC=CC=1C(=O)C(CCC)CC(C=C1O)=CC=C1N1CC(=O)NS1(=O)=O KBSSPJQTFBORLB-UHFFFAOYSA-N 0.000 description 1
- RYBXVHWOECBUAR-UHFFFAOYSA-N 5-[4-[2-(2,4-dimethyl-1,3-thiazol-5-yl)ethyl]-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound S1C(C)=NC(C)=C1CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 RYBXVHWOECBUAR-UHFFFAOYSA-N 0.000 description 1
- JJIQYBXWMVCZFD-UHFFFAOYSA-N 7-(iodomethyl)-6,7-dihydrobenzo[d][2]benzazepin-5-one Chemical compound ICC1NC(=O)C2=CC=CC=C2C2=CC=CC=C12 JJIQYBXWMVCZFD-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- CCFNBOVNMOLCHA-UHFFFAOYSA-N n-[4-(2-acetyl-3-hydroxyphenoxy)butyl]-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanamide Chemical compound CC(=O)C1=C(O)C=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 CCFNBOVNMOLCHA-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- DHWQSSVGSIQILQ-UHFFFAOYSA-N tert-butyl n-[4-(2-methylsulfonyl-3-phenylmethoxyphenoxy)butyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCOC1=CC=CC(OCC=2C=CC=CC=2)=C1S(C)(=O)=O DHWQSSVGSIQILQ-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78850206P | 2006-03-31 | 2006-03-31 | |
| PCT/US2007/065421 WO2007115058A2 (en) | 2006-03-31 | 2007-03-29 | Thiadiazolidinone inhibitors of ptpase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009532379A JP2009532379A (ja) | 2009-09-10 |
| JP2009532379A5 true JP2009532379A5 (cg-RX-API-DMAC10.html) | 2010-04-30 |
Family
ID=38458259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009503258A Pending JP2009532379A (ja) | 2006-03-31 | 2007-03-29 | ＰＴＰａｓｅのチアジアゾリジノン阻害剤 |
Country Status (11)
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA94724C2 (en) * | 2005-12-08 | 2011-06-10 | Новартис Аг | Thiadiazolidinone derivatives as antidiabetic agents |
| EP1963294B1 (en) * | 2005-12-08 | 2012-10-10 | Novartis AG | 1,2,5-thiazolidine derivatives useful for treating conditions mediated by protein tyrosine phosphatases (ptpase) |
| US20080293782A1 (en) * | 2005-12-08 | 2008-11-27 | David Barnes | 1,1,3-Trioxo-1,2,5-Thiadiazolidines and Their Use as Ptp-Ases Inhibitors |
| UA94921C2 (en) | 2005-12-08 | 2011-06-25 | Новартис Аг | 1-orthofluorophenyl substituted 1, 2, 5-thiazolidinedione derivatives as ptp-as inhibitors |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| NZ600367A (en) | 2009-12-04 | 2013-08-30 | Taisho Pharmaceutical Co Ltd | 2-pyridone compounds |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| 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 |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process 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 |
| 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 |
| WO2012046869A1 (ja) | 2010-10-08 | 2012-04-12 | 持田製薬株式会社 | 環状アミド誘導体 |
| 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 |
| 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 |
| WO2012120053A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012147516A1 (ja) * | 2011-04-28 | 2012-11-01 | 持田製薬株式会社 | 環状アミド誘導体 |
| EP2703393A4 (en) * | 2011-04-28 | 2014-09-24 | Mochida Pharm Co Ltd | CYCLIC AMIDE DERIVATIVE |
| 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 |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US9216988B2 (en) * | 2011-12-22 | 2015-12-22 | Genentech, Inc. | Benzyl sulfonamide derivatives as RORc modulators |
| CN102659539A (zh) * | 2012-05-15 | 2012-09-12 | 北京化工大学 | 一种由α,β-不饱和酰氯制备二氢查尔酮类化合物的方法 |
| MX2015006152A (es) | 2012-11-20 | 2016-01-20 | Genentech Inc | Compuestos de aminopirimidina como inhibidores de mutantes de egfr que contienen t7 9 0m. |
| US10550091B2 (en) | 2016-03-25 | 2020-02-04 | St. Jude Children's Research Hospital | 1,4,5-substituted 1,2,3-triazole analogues as antagonists of the pregnane X receptor |
| AU2019200683B2 (en) * | 2018-02-01 | 2024-05-30 | The University Of Sydney | Anti-cancer compounds |
| WO2019191189A1 (en) * | 2018-03-27 | 2019-10-03 | Neuropore Therapies, Inc. | Compounds as modulators of tlr2 signaling |
| JP7217762B2 (ja) * | 2018-06-21 | 2023-02-03 | カリコ ライフ サイエンシーズ エルエルシー | タンパク質チロシンホスファターゼ阻害剤及びそれらの使用方法 |
| WO2020035019A1 (zh) | 2018-08-17 | 2020-02-20 | 浙江海正药业股份有限公司 | 吲唑胺类衍生物及其制备方法和其在医药上的用途 |
| AU2020234712B2 (en) * | 2019-03-14 | 2025-12-04 | Abbvie Inc. | Protein tyrosine phosphatase inhibitors and methods of use thereof |
| PE20241474A1 (es) * | 2021-11-23 | 2024-07-17 | Kumquat Biosciences Inc | Compuestos que contienen heteroatomos y usos de estos |
| CA3243580A1 (en) * | 2022-02-02 | 2023-08-10 | Nerio Therapeutics, Inc. | TYROSINE PHOSPHATASE PROTEIN INHIBITORS AND THEIR USES |
| WO2023200964A1 (en) * | 2022-04-14 | 2023-10-19 | Nerio Therapeutics, Inc. | Protein tyrosine phosphatase inhibitors and uses thereof |
| CN119522216A (zh) * | 2022-05-13 | 2025-02-25 | 尼斯治疗公司 | Ptpn2抑制剂 |
| CN117658947A (zh) * | 2022-09-06 | 2024-03-08 | 杭州中美华东制药有限公司 | 蛋白酪氨酸磷酸酶抑制作用的5-(取代芳基)-1,2,5-噻二唑啉-3-酮类化合物 |
| AR131413A1 (es) * | 2022-12-21 | 2025-03-19 | Bristol Myers Squibb Co | Inhibidores de la proteína tirosina fosfatasa, composiciones y métodos de uso |
| CN116283467B (zh) * | 2023-01-18 | 2024-06-11 | 四川大学 | 一种合成二芳基烷基甲烷的方法 |
| AU2024276994A1 (en) | 2023-05-24 | 2025-10-23 | Kumquat Biosciences Inc. | Heterocyclic compounds and uses thereof |
| CN119818693A (zh) * | 2023-10-13 | 2025-04-15 | 华东师范大学 | 一种用于前药给药系统的可裂解支链连接体化合物及其制备和应用 |
| WO2026015417A1 (en) * | 2024-07-08 | 2026-01-15 | Bristol-Myers Squibb Company | Inhibitors of protein tyrosine phosphatase, compositions, and methods of use |
| US12516051B1 (en) | 2024-09-30 | 2026-01-06 | St. Jude Children's Research Hospital, Inc. | Small molecule degraders and fluorescent probes of PXR |
| CN119220146A (zh) * | 2024-10-24 | 2024-12-31 | 山东三佳聚合高分子材料有限公司 | 一种新型隔热保温涂料 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2381397A (en) * | 1996-04-19 | 1997-11-12 | Novo Nordisk A/S | Modulators of molecules with phosphotyrosine recognition units |
| ES2378146T3 (es) * | 2002-04-03 | 2012-04-09 | Novartis Ag | Derivados de 1,1-dioxo-1, 2,5-tiazolidina-3-ona sustituida como inhibidores de ptpasa 1B |
| GB0225986D0 (en) * | 2002-11-07 | 2002-12-11 | Astrazeneca Ab | Chemical compounds |
| GB0227813D0 (en) * | 2002-11-29 | 2003-01-08 | Astrazeneca Ab | Chemical compounds |
| US7432292B2 (en) * | 2002-12-30 | 2008-10-07 | Vertex Pharmaceuticals Incorporated | Sulfhydantoins as phosphate isosteres |
| EP1963294B1 (en) * | 2005-12-08 | 2012-10-10 | Novartis AG | 1,2,5-thiazolidine derivatives useful for treating conditions mediated by protein tyrosine phosphatases (ptpase) |
| US20080293782A1 (en) * | 2005-12-08 | 2008-11-27 | David Barnes | 1,1,3-Trioxo-1,2,5-Thiadiazolidines and Their Use as Ptp-Ases Inhibitors |
| UA94921C2 (en) * | 2005-12-08 | 2011-06-25 | Новартис Аг | 1-orthofluorophenyl substituted 1, 2, 5-thiazolidinedione derivatives as ptp-as inhibitors |
-
2007
- 2007-03-29 RU RU2008143053/04A patent/RU2008143053A/ru not_active Application Discontinuation
- 2007-03-29 WO PCT/US2007/065421 patent/WO2007115058A2/en not_active Ceased
- 2007-03-29 EP EP20070780835 patent/EP2038267A2/en not_active Withdrawn
- 2007-03-29 CN CNA2007800120054A patent/CN101421256A/zh active Pending
- 2007-03-29 KR KR1020087026637A patent/KR20080110882A/ko not_active Withdrawn
- 2007-03-29 US US12/295,545 patent/US8084448B2/en not_active Expired - Fee Related
- 2007-03-29 JP JP2009503258A patent/JP2009532379A/ja active Pending
- 2007-03-29 MX MX2008012598A patent/MX2008012598A/es not_active Application Discontinuation
- 2007-03-29 CA CA002647472A patent/CA2647472A1/en not_active Abandoned
- 2007-03-29 AU AU2007233251A patent/AU2007233251A1/en not_active Abandoned
- 2007-03-29 BR BRPI0710182-1A patent/BRPI0710182A2/pt not_active Application Discontinuation
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