JP2012021006A5 - - Google Patents
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- Publication number
- JP2012021006A5 JP2012021006A5 JP2011177726A JP2011177726A JP2012021006A5 JP 2012021006 A5 JP2012021006 A5 JP 2012021006A5 JP 2011177726 A JP2011177726 A JP 2011177726A JP 2011177726 A JP2011177726 A JP 2011177726A JP 2012021006 A5 JP2012021006 A5 JP 2012021006A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- methyl
- benzyl
- phenyl
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 318
- -1 ester salt Chemical class 0.000 claims 94
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 64
- 125000003342 alkenyl group Chemical group 0.000 claims 36
- 125000000304 alkynyl group Chemical group 0.000 claims 31
- 125000001475 halogen functional group Chemical group 0.000 claims 29
- 125000001424 substituent group Chemical group 0.000 claims 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims 27
- 125000003118 aryl group Chemical group 0.000 claims 26
- 125000001072 heteroaryl group Chemical group 0.000 claims 26
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 23
- 125000001188 haloalkyl group Chemical group 0.000 claims 23
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 22
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 21
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 19
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 14
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 14
- 125000004043 oxo group Chemical group O=* 0.000 claims 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 13
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 13
- 125000004971 nitroalkyl group Chemical group 0.000 claims 13
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 11
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 10
- 125000004967 formylalkyl group Chemical group 0.000 claims 10
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims 10
- 150000003839 salts Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 239000000651 prodrug Chemical class 0.000 claims 8
- 229940002612 prodrug Drugs 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 150000002148 esters Chemical class 0.000 claims 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 0.000 claims 2
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims 2
- 125000000232 haloalkynyl group Chemical group 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- HADZANADRJVJNN-ULGDXOGHSA-N (2r)-2-[[2-[(3-fluorophenyl)methylamino]acetyl]amino]-n-[(2s,3r)-3-hydroxy-4-[[4-[(e)-hydroxyiminomethyl]phenyl]sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-3,3-dimethylbutanamide Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(\C=N\O)=CC=1)NC(=O)[C@H](NC(=O)CNCC=1C=C(F)C=CC=1)C(C)(C)C)C1=CC=CC=C1 HADZANADRJVJNN-ULGDXOGHSA-N 0.000 claims 1
- HADZANADRJVJNN-MLANHYEYSA-N (2s)-2-[[2-[(3-fluorophenyl)methylamino]acetyl]amino]-n-[(2s,3r)-3-hydroxy-4-[[4-[(e)-hydroxyiminomethyl]phenyl]sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-3,3-dimethylbutanamide Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(\C=N\O)=CC=1)NC(=O)[C@@H](NC(=O)CNCC=1C=C(F)C=CC=1)C(C)(C)C)C1=CC=CC=C1 HADZANADRJVJNN-MLANHYEYSA-N 0.000 claims 1
- XAHUNXHJQGQIFA-LNCSBHOOSA-N (2s,3s)-2-[[(3-aminophenyl)methyl-methylcarbamoyl]amino]-n-[(2s,3r)-3-hydroxy-4-[[4-[(e)-hydroxyiminomethyl]phenyl]sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-3-methylpentanamide Chemical compound N([C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C=CC=CC=1)[C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(\C=N\O)=CC=1)C(=O)N(C)CC1=CC=CC(N)=C1 XAHUNXHJQGQIFA-LNCSBHOOSA-N 0.000 claims 1
- DMRYBLMRXWKJPS-ILOUGMCFSA-N (2s,3s)-2-[[2-[(3-fluorophenyl)methylamino]acetyl]amino]-n-[(2s,3r)-3-hydroxy-4-[[4-[(e)-hydroxyiminomethyl]phenyl]sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-3-methylpentanamide Chemical compound N([C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C=CC=CC=1)[C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(\C=N\O)=CC=1)C(=O)CNCC1=CC=CC(F)=C1 DMRYBLMRXWKJPS-ILOUGMCFSA-N 0.000 claims 1
- 125000005084 alkoxyalkylaminoalkyl group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000005335 azido alkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- FASRBZCEQXWPSU-ADBCUUMKSA-N benzyl n-[(2s)-1-[[(2s,3r)-3-hydroxy-4-[[4-[(e)-hydroxyiminomethyl]phenyl]sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]carbamate Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(\C=N\O)=CC=1)NC(=O)[C@@H](NC(=O)OCC=1C=CC=CC=1)C(C)(C)C)C1=CC=CC=C1 FASRBZCEQXWPSU-ADBCUUMKSA-N 0.000 claims 1
- AHMHMGFLIXDQDO-CRKYSRFYSA-N benzyl n-[(2s)-1-[[(2s,3r)-3-hydroxy-4-[[4-[(e)-hydroxyiminomethyl]phenyl]sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamate Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(\C=N\O)=CC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 AHMHMGFLIXDQDO-CRKYSRFYSA-N 0.000 claims 1
- JZXIWUZDOBNYJN-HXEKFNLZSA-N benzyl n-[(2s)-4-amino-1-[[(2s,3r)-3-hydroxy-4-[[4-[(e)-hydroxyiminomethyl]phenyl]sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]amino]-1,4-dioxobutan-2-yl]carbamate Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(\C=N\O)=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 JZXIWUZDOBNYJN-HXEKFNLZSA-N 0.000 claims 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- WRSLYHOZMJSDIU-BZFPHEIKSA-N methyl n-[(2s)-1-[[(2s,3r)-3-hydroxy-4-[[4-[(e)-hydroxyiminomethyl]phenyl]sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]carbamate Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(\C=N\O)=CC=1)C1=CC=CC=C1 WRSLYHOZMJSDIU-BZFPHEIKSA-N 0.000 claims 1
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- WJTNYOMNYKREIK-CRZKBIAESA-N tert-butyl n-[(2s)-1-[[(2s,3r)-3-hydroxy-4-[[4-[(e)-hydroxyiminomethyl]phenyl]sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]carbamate Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(\C=N\O)=CC=1)NC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)C1=CC=CC=C1 WJTNYOMNYKREIK-CRZKBIAESA-N 0.000 claims 1
- ZQSBRXJFPXAWPJ-FFQSGBJSSA-N tert-butyl n-[(2s,3s)-1-[[(2s,3r)-3-hydroxy-4-[[4-[(e)-hydroxyiminomethyl]phenyl]sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamate Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC(C)(C)C)[C@@H](C)CC)[C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(\C=N\O)=CC=1)C1=CC=CC=C1 ZQSBRXJFPXAWPJ-FFQSGBJSSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/733,915 | 2003-12-11 | ||
| US10/733,915 US20050131042A1 (en) | 2003-12-11 | 2003-12-11 | HIV protease inhibiting compounds |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006543826A Division JP2007513944A (ja) | 2003-12-11 | 2004-11-10 | Ｈｉｖプロテアーゼ阻害性スルホンアミド類 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012021006A JP2012021006A (ja) | 2012-02-02 |
| JP2012021006A5 true JP2012021006A5 (https=) | 2012-11-01 |
Family
ID=34653241
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006543826A Pending JP2007513944A (ja) | 2003-12-11 | 2004-11-10 | Ｈｉｖプロテアーゼ阻害性スルホンアミド類 |
| JP2011177726A Pending JP2012021006A (ja) | 2003-12-11 | 2011-08-15 | Ｈｉｖプロテアーゼ阻害性スルホンアミド類 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006543826A Pending JP2007513944A (ja) | 2003-12-11 | 2004-11-10 | Ｈｉｖプロテアーゼ阻害性スルホンアミド類 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20050131042A1 (https=) |
| EP (3) | EP2216334B1 (https=) |
| JP (2) | JP2007513944A (https=) |
| AT (1) | ATE452889T1 (https=) |
| CA (2) | CA2549389A1 (https=) |
| DE (1) | DE602004024830D1 (https=) |
| ES (3) | ES2337581T3 (https=) |
| MX (1) | MXPA06006610A (https=) |
| TW (1) | TWI353833B (https=) |
| WO (1) | WO2005061450A2 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0847452B1 (en) | 1995-06-07 | 2009-04-01 | Progenics Pharmaceuticals, Inc. | Monoclonal antibody for inhibiting hiv-1 envelope glycoprotein mediated membrane fusion |
| US7118859B2 (en) * | 1996-01-17 | 2006-10-10 | Progenics Pharmaceuticals, Inc. | Methods for inhibiting HIV-1 infection |
| US6344545B1 (en) * | 1996-06-14 | 2002-02-05 | Progenics Pharmaceuticals, Inc. | Method for preventing HIV-1 infection of CD4+ cells |
| US7858298B1 (en) | 1996-04-01 | 2010-12-28 | Progenics Pharmaceuticals Inc. | Methods of inhibiting human immunodeficiency virus type 1 (HIV-1) infection through the administration of CCR5 chemokine receptor antagonists |
| US20040228869A1 (en) * | 1998-12-16 | 2004-11-18 | Progenics Pharmaceuticals, Inc. | Synergistic inhibition of HIV-1 fusion and attachment, compositions and antibodies thereto |
| US20080015348A1 (en) * | 1998-12-16 | 2008-01-17 | Progenics Pharmaceuticals, Inc. | Nucleic acids encoding polypeptides of anti-CCR5 antibodies |
| US7138119B2 (en) * | 2000-09-15 | 2006-11-21 | Progenics Pharmaceuticals, Inc. | Compositions and methods for inhibition of HIV-1 infection |
| US7060273B2 (en) * | 2001-04-06 | 2006-06-13 | Progenics Pharmaceuticals, Inc. | Methods for inhibiting HIV-1 infection |
| US7122185B2 (en) * | 2002-02-22 | 2006-10-17 | Progenics Pharmaceuticals, Inc. | Anti-CCR5 antibody |
| JP4803352B2 (ja) * | 2005-07-13 | 2011-10-26 | Ｊｓｒ株式会社 | アミノ酸−ｎ−カルボキシ無水物の製造方法 |
| CA2616189C (en) * | 2005-07-22 | 2019-03-26 | Progenics Pharmaceuticals, Inc. | Methods for reducing viral load in hiv-1-infected patients |
| US8048871B2 (en) * | 2006-08-18 | 2011-11-01 | Sequoia Pharmaceuticals, Inc. | Compositions and methods for inhibiting cytochrome P450 |
| JP5270943B2 (ja) * | 2008-03-28 | 2013-08-21 | 大阪瓦斯株式会社 | フルオレン誘導体およびこのフルオレン誘導体を用いたアミノ基含有フルオレン誘導体の製造方法 |
| SI2373172T1 (sl) | 2008-12-03 | 2013-12-31 | Presidio Pharmaceuticals, Inc. | Inhibitorji HCV NS5A |
| US8314250B2 (en) | 2009-11-24 | 2012-11-20 | Hoffmann-La Roche Inc. | Sultam derivatives |
| CA2902624C (en) | 2013-02-28 | 2021-05-18 | Takeda Pharmaceutical Company Limited | Method for producing sulfonyl chloride compound |
| AU2013385618B2 (en) * | 2013-04-02 | 2017-01-05 | Annji Pharmaceutical Co., Ltd. | Multifunctional quinoline derivatives as anti-neurodegenerative agents |
| UY37592A (es) | 2017-02-06 | 2018-08-31 | Gilead Sciences Inc | Compuestos inhibidores del vih |
| CN111205206B (zh) * | 2020-02-13 | 2021-10-22 | 中国医学科学院医药生物技术研究所 | 一种包含氨基酸连接链的羰基化合物或其药学上可接受的盐及其制备方法和应用 |
| CN111265499B (zh) * | 2020-02-17 | 2022-11-15 | 江苏艾立康医药科技有限公司 | 一种洛匹那韦吸入气雾剂及其制备方法 |
| US12083099B2 (en) | 2020-10-28 | 2024-09-10 | Accencio LLC | Methods of treating symptoms of coronavirus infection with viral protease inhibitors |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE218541T1 (de) * | 1992-08-25 | 2002-06-15 | Searle & Co | Hydroxyethylaminosulfonamide verwendbar als inhibitoren retroviraler proteasen |
| IS2334B (is) * | 1992-09-08 | 2008-02-15 | Vertex Pharmaceuticals Inc., (A Massachusetts Corporation) | Aspartyl próteasi hemjari af nýjum flokki súlfonamíða |
| US5723490A (en) * | 1992-09-08 | 1998-03-03 | Vertex Pharmaceuticals Incorporated | THF-containing sulfonamide inhibitors of aspartyl protease |
| EP0715618B1 (en) * | 1993-08-24 | 1998-12-16 | G.D. Searle & Co. | Hydroxyethylamino sulphonamides useful as retroviral protease inhibitors |
| UA49803C2 (uk) * | 1994-06-03 | 2002-10-15 | Дж.Д. Сьорль Енд Ко | Спосіб лікування ретровірусних інфекцій |
| US6150556A (en) * | 1995-03-10 | 2000-11-21 | G. D. Dearle & Co. | Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors |
| US5691372A (en) * | 1995-04-19 | 1997-11-25 | Vertex Pharmaceuticals Incorporated | Oxygenated-Heterocycle containing sulfonamide inhibitors of aspartyl protease |
| AU7722296A (en) * | 1995-11-15 | 1997-06-05 | G.D. Searle & Co. | Substituted sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease inhibitors |
| US5914332A (en) * | 1995-12-13 | 1999-06-22 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| US6436989B1 (en) * | 1997-12-24 | 2002-08-20 | Vertex Pharmaceuticals, Incorporated | Prodrugs of aspartyl protease inhibitors |
| WO1999033792A2 (en) * | 1997-12-24 | 1999-07-08 | Vertex Pharmaceuticals Incorporated | Prodrugs os aspartyl protease inhibitors |
| US6251906B1 (en) * | 1998-05-15 | 2001-06-26 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| GB9914821D0 (en) * | 1999-06-24 | 1999-08-25 | Glaxo Group Ltd | Compounds |
| US6617310B2 (en) * | 2000-07-19 | 2003-09-09 | Bristol-Myers Squibb Pharma Company | Phosphate esters of bis-amino acid sulfonamides containing substituted benzyl amines |
| US20020022742A1 (en) * | 2000-07-19 | 2002-02-21 | Harris Gregory D. | Salt forms of an HIV protease inhibitor |
| EA009590B1 (ru) * | 2001-05-11 | 2008-02-28 | Тиботек Фармасьютикалз Лтд. | 2-аминобензоксазолсульфонамидные ингибиторы вич-протеазы широкого спектра |
| US7157489B2 (en) * | 2002-03-12 | 2007-01-02 | The Board Of Trustees Of The University Of Illinois | HIV protease inhibitors |
-
2003
- 2003-12-11 US US10/733,915 patent/US20050131042A1/en not_active Abandoned
-
2004
- 2004-11-10 EP EP09176641A patent/EP2216334B1/en not_active Expired - Lifetime
- 2004-11-10 AT AT04810802T patent/ATE452889T1/de not_active IP Right Cessation
- 2004-11-10 EP EP10176829.9A patent/EP2264032B1/en not_active Expired - Lifetime
- 2004-11-10 ES ES04810802T patent/ES2337581T3/es not_active Expired - Lifetime
- 2004-11-10 DE DE602004024830T patent/DE602004024830D1/de not_active Expired - Lifetime
- 2004-11-10 WO PCT/US2004/037745 patent/WO2005061450A2/en not_active Ceased
- 2004-11-10 MX MXPA06006610A patent/MXPA06006610A/es active IP Right Grant
- 2004-11-10 ES ES09176641T patent/ES2396761T3/es not_active Expired - Lifetime
- 2004-11-10 EP EP04810802A patent/EP1709037B8/en not_active Expired - Lifetime
- 2004-11-10 JP JP2006543826A patent/JP2007513944A/ja active Pending
- 2004-11-10 CA CA002549389A patent/CA2549389A1/en not_active Abandoned
- 2004-11-10 CA CA2792483A patent/CA2792483A1/en not_active Abandoned
- 2004-11-10 ES ES10176829T patent/ES2426965T3/es not_active Expired - Lifetime
- 2004-12-10 TW TW093138495A patent/TWI353833B/zh not_active IP Right Cessation
-
2011
- 2011-08-15 JP JP2011177726A patent/JP2012021006A/ja active Pending