KR20090080573A - 신경계 증후군의 치료를 위한 pde-4 억제제로서의 4-(4-알콕시-3-히드록시페닐)-2-피롤리돈 유도체 - Google Patents
신경계 증후군의 치료를 위한 pde-4 억제제로서의 4-(4-알콕시-3-히드록시페닐)-2-피롤리돈 유도체 Download PDFInfo
- Publication number
- KR20090080573A KR20090080573A KR1020097014588A KR20097014588A KR20090080573A KR 20090080573 A KR20090080573 A KR 20090080573A KR 1020097014588 A KR1020097014588 A KR 1020097014588A KR 20097014588 A KR20097014588 A KR 20097014588A KR 20090080573 A KR20090080573 A KR 20090080573A
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- KR
- South Korea
- Prior art keywords
- pyrrolidone
- methoxyphenyl
- cyclopentyloxy
- alkyl
- substituted
- 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.)
- Ceased
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- 208000011580 syndromic disease Diseases 0.000 title description 5
- 230000000926 neurological effect Effects 0.000 title description 4
- 239000003112 inhibitor Substances 0.000 title description 3
- -1 4- (substituted-phenyl) -2-pyrrolidinone compounds Chemical class 0.000 claims abstract description 280
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 125000000217 alkyl group Chemical group 0.000 claims description 153
- 125000004432 carbon atom Chemical group C* 0.000 claims description 124
- 229910052736 halogen Inorganic materials 0.000 claims description 114
- 150000002367 halogens Chemical class 0.000 claims description 114
- 125000004043 oxo group Chemical group O=* 0.000 claims description 79
- 125000003545 alkoxy group Chemical group 0.000 claims description 69
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 125000003282 alkyl amino group Chemical group 0.000 claims description 53
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 53
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 52
- 229920006395 saturated elastomer Polymers 0.000 claims description 51
- 125000006413 ring segment Chemical group 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 46
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 45
- 125000000623 heterocyclic group Chemical group 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 38
- 125000002252 acyl group Chemical group 0.000 claims description 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 29
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 29
- 125000004414 alkyl thio group Chemical group 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 29
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 29
- 125000004423 acyloxy group Chemical group 0.000 claims description 28
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 28
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 125000004434 sulfur atom Chemical group 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 21
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 21
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 20
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 18
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- CZVACZOPGDMVPI-UHFFFAOYSA-N 4-[4-methoxy-3-(3-phenylpropoxy)phenyl]pyrrolidin-2-one Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OCCCC1=CC=CC=C1 CZVACZOPGDMVPI-UHFFFAOYSA-N 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
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- LSFGUQHTBIISPG-SFHVURJKSA-N (4r)-1-[(2-chlorophenyl)methyl]-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one Chemical compound COC1=CC=C([C@H]2CC(=O)N(CC=3C(=CC=CC=3)Cl)C2)C=C1OC1CCCC1 LSFGUQHTBIISPG-SFHVURJKSA-N 0.000 claims description 4
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- YIMRISPWLFQGDA-KRWDZBQOSA-N (4r)-1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one Chemical compound COC1=CC=C([C@H]2CC(=O)N(CC=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)C2)C=C1OC1CCCC1 YIMRISPWLFQGDA-KRWDZBQOSA-N 0.000 claims description 4
- JYAROCCYXSPCQH-INIZCTEOSA-N (4r)-1-butyl-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one Chemical compound C1C(=O)N(CCCC)C[C@H]1C1=CC=C(OC)C(OC2CCCC2)=C1 JYAROCCYXSPCQH-INIZCTEOSA-N 0.000 claims description 4
- LGBQCIPOEYOPSZ-HNNXBMFYSA-N (4r)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-(2-methoxyethyl)pyrrolidin-2-one Chemical compound C1C(=O)N(CCOC)C[C@H]1C1=CC=C(OC)C(OC2CCCC2)=C1 LGBQCIPOEYOPSZ-HNNXBMFYSA-N 0.000 claims description 4
- MBFVIJKOQKNJKX-KRWDZBQOSA-N (4r)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(2,3-difluorophenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=C([C@H]2CC(=O)N(CC=3C(=C(F)C=CC=3)F)C2)C=C1OC1CCCC1 MBFVIJKOQKNJKX-KRWDZBQOSA-N 0.000 claims description 4
- XLVHYQWLMAYSJS-KRWDZBQOSA-N (4r)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(2,4-difluorophenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=C([C@H]2CC(=O)N(CC=3C(=CC(F)=CC=3)F)C2)C=C1OC1CCCC1 XLVHYQWLMAYSJS-KRWDZBQOSA-N 0.000 claims description 4
- HBJULFRETHSMHP-INIZCTEOSA-N (4r)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(2,6-difluorophenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=C([C@H]2CC(=O)N(CC=3C(=CC=CC=3F)F)C2)C=C1OC1CCCC1 HBJULFRETHSMHP-INIZCTEOSA-N 0.000 claims description 4
- JZNWWODWNNLGID-SFHVURJKSA-N (4r)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(2-fluorophenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=C([C@H]2CC(=O)N(CC=3C(=CC=CC=3)F)C2)C=C1OC1CCCC1 JZNWWODWNNLGID-SFHVURJKSA-N 0.000 claims description 4
- ZKZGOHAIRWNOTC-FQEVSTJZSA-N (4r)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(2-methylphenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=C([C@H]2CC(=O)N(CC=3C(=CC=CC=3)C)C2)C=C1OC1CCCC1 ZKZGOHAIRWNOTC-FQEVSTJZSA-N 0.000 claims description 4
- XAAPAYLZALZJOA-DEOSSOPVSA-N (4r)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(2-phenylphenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=C([C@H]2CC(=O)N(CC=3C(=CC=CC=3)C=3C=CC=CC=3)C2)C=C1OC1CCCC1 XAAPAYLZALZJOA-DEOSSOPVSA-N 0.000 claims description 4
- IJRMNBMFUBIHEG-KRWDZBQOSA-N (4r)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(3,4-dichlorophenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=C([C@H]2CC(=O)N(CC=3C=C(Cl)C(Cl)=CC=3)C2)C=C1OC1CCCC1 IJRMNBMFUBIHEG-KRWDZBQOSA-N 0.000 claims description 4
- KZIJCFUSRLJAQR-KRWDZBQOSA-N (4r)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(3,4-difluorophenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=C([C@H]2CC(=O)N(CC=3C=C(F)C(F)=CC=3)C2)C=C1OC1CCCC1 KZIJCFUSRLJAQR-KRWDZBQOSA-N 0.000 claims description 4
- JOCZJNKUOWPQST-KRWDZBQOSA-N (4r)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(3,5-difluorophenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=C([C@H]2CC(=O)N(CC=3C=C(F)C=C(F)C=3)C2)C=C1OC1CCCC1 JOCZJNKUOWPQST-KRWDZBQOSA-N 0.000 claims description 4
- XSNZHLZBNOJCAD-SFHVURJKSA-N (4r)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(3-fluorophenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=C([C@H]2CC(=O)N(CC=3C=C(F)C=CC=3)C2)C=C1OC1CCCC1 XSNZHLZBNOJCAD-SFHVURJKSA-N 0.000 claims description 4
- OVFDOBITJAKRJC-IBGZPJMESA-N (4r)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(3-methoxyphenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=CC(CN2C(C[C@@H](C2)C=2C=C(OC3CCCC3)C(OC)=CC=2)=O)=C1 OVFDOBITJAKRJC-IBGZPJMESA-N 0.000 claims description 4
- JHUISJNNTQYGFK-SFHVURJKSA-N (4r)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(4-fluorophenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=C([C@H]2CC(=O)N(CC=3C=CC(F)=CC=3)C2)C=C1OC1CCCC1 JHUISJNNTQYGFK-SFHVURJKSA-N 0.000 claims description 4
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Classifications
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| US8153646B2 (en) | 2000-08-10 | 2012-04-10 | Dart Neuroscience (Cayman) Ltd. | Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation |
| US9931318B2 (en) | 2003-04-08 | 2018-04-03 | Dart Neuroscience (Cayman) Ltd. | Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation |
| DE60140074D1 (de) * | 2000-12-14 | 2009-11-12 | Burnham Inst | Non-apoptotische formen des zelltods und verfahren zur modulation |
| CN1604776A (zh) | 2001-10-16 | 2005-04-06 | 记忆药物公司 | 作为用于治疗神经病综合症的pde-4抑制剂的4-(4-烷氧基-3-羟基苯基)-2-吡咯烷酮衍生物 |
| US20030157053A1 (en) * | 2002-02-19 | 2003-08-21 | Sabina Sperandio | Modulators of paraptosis and related methods |
| US7495016B2 (en) | 2002-10-21 | 2009-02-24 | Irm Llc | Pyrrolidones with anti-HIV activity |
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| DOP2005000123A (es) * | 2004-07-02 | 2011-07-15 | Merck Sharp & Dohme | Inhibidores de cetp |
| EP1802615A1 (en) * | 2004-10-20 | 2007-07-04 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors |
| US8637559B2 (en) * | 2005-11-15 | 2014-01-28 | Otsuka Pharmaceutical Co., Ltd. | Oxazole compound and pharmaceutical composition |
| US7915271B2 (en) * | 2005-12-30 | 2011-03-29 | Merck Sharp & Dohme Corp. | 1,3-oxazolidin-2-one derivatives useful as CETP inhibitors |
| BRPI0711816A2 (pt) * | 2006-05-19 | 2011-12-13 | Helicon Therapeutics Inc | inibidores fosfodiesterase 4 para rehabilitação motora e cognitiva |
| ES2320954B1 (es) * | 2007-03-02 | 2010-03-16 | Laboratorio Almirall S.A. | Nuevo procedimiento de preparacion de 3-metil-4-fenilisoxazolo (3,4-d)iridazin-7(6h)-ona. |
| WO2009067607A2 (en) * | 2007-11-20 | 2009-05-28 | Memory Pharmaceuticals Corporation | Combinations of pde4 inhibitors and antipsychotics for the treatment of psychotic disorders |
| DK3260118T3 (da) | 2008-10-16 | 2021-04-19 | Univ Johns Hopkins | Fremgangsmåder og sammensætninger til forbedring af kognitiv funktion |
| WO2010075086A2 (en) * | 2008-12-15 | 2010-07-01 | Auspex Pharmaceuticals, Inc. | Pyrrolidinone inhibitors of pde-4 |
| EP3090999A1 (en) | 2009-06-18 | 2016-11-09 | Concert Pharmaceuticals Inc. | Deuterated isoindoline-1, 3-dione derivatives as pde4 and tnf-alpha inhibitors |
| US20140206667A1 (en) | 2012-11-14 | 2014-07-24 | Michela Gallagher | Methods and compositions for treating schizophrenia |
| CN105121439A (zh) | 2013-02-19 | 2015-12-02 | 辉瑞公司 | 作为pde4亚型抑制剂用于治疗cns和其他病症的氮杂苯并咪唑化合物 |
| AU2014228512A1 (en) | 2013-03-15 | 2015-10-01 | Agenebio, Inc. | Methods and compositions for improving cognitive function |
| WO2014144663A1 (en) | 2013-03-15 | 2014-09-18 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| WO2016012896A1 (en) | 2014-07-24 | 2016-01-28 | Pfizer Inc. | Pyrazolopyrimidine compounds |
| PL3177624T3 (pl) | 2014-08-06 | 2019-09-30 | Pfizer Inc. | Związki imidazopirydazynowe |
| CA2986598C (en) | 2015-05-22 | 2023-09-26 | Agenebio, Inc. | Extended release pharmaceutical compositions of levetiracetam |
| JP2017141222A (ja) * | 2016-02-09 | 2017-08-17 | 国立大学法人帯広畜産大学 | パーキンソン病に併発した認知障害の治療剤及びそのスクリーニング方法 |
| TWI877358B (zh) * | 2020-04-29 | 2025-03-21 | 大陸商廣東東陽光藥業股份有限公司 | 取代的吡咯烷類化合物及其在藥物中的應用 |
| CN112479966B (zh) * | 2020-12-11 | 2022-05-17 | 南京工业大学 | 一种咯利普兰的合成方法 |
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| DE2413935A1 (de) | 1974-03-20 | 1975-10-16 | Schering Ag | 4-(polyalkoxy-phenyl)-2-pyrrolidone |
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| US5814651A (en) | 1992-12-02 | 1998-09-29 | Pfizer Inc. | Catechol diethers as selective PDEIV inhibitors |
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| CN1087725C (zh) | 1994-03-25 | 2002-07-17 | 同位素技术有限公司 | 用氘代方法增强药物效果 |
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| DK0758233T3 (da) | 1994-04-21 | 2004-03-22 | Schering Ag | PDE IV-inhibitorer til behandling af multipel sklerose |
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| DE19601938A1 (de) | 1996-01-12 | 1997-07-17 | Schering Ag | Neue Phosphodiesteraseinhibitoren |
| JPH1072415A (ja) | 1996-06-26 | 1998-03-17 | Nikken Chem Co Ltd | 3−アニリノ−2−シクロアルケノン誘導体 |
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| JP3085249B2 (ja) | 1997-07-09 | 2000-09-04 | 松下電器産業株式会社 | ホットプレート |
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| EP1343528A2 (en) | 2000-11-02 | 2003-09-17 | Research Foundation of City University of New York | Methods for stimulating nervous system regeneration and repair by inhibition phosphodiesterase type 4 |
| US6495154B1 (en) * | 2000-11-21 | 2002-12-17 | Vivus Inc. | On demand administration of clomipramine and salts thereof to treat premature ejaculation |
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- 2002-10-16 NZ NZ532288A patent/NZ532288A/en not_active IP Right Cessation
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- 2002-10-16 JP JP2003535784A patent/JP4484515B2/ja not_active Expired - Fee Related
- 2002-10-16 KR KR1020097014588A patent/KR20090080573A/ko not_active Ceased
- 2002-10-16 KR KR1020047005475A patent/KR100951218B1/ko not_active Expired - Fee Related
- 2002-10-16 AT AT02801710T patent/ATE444065T1/de not_active IP Right Cessation
- 2002-10-16 AU AU2002335015A patent/AU2002335015B8/en not_active Ceased
- 2002-10-16 ES ES02801710T patent/ES2334650T3/es not_active Expired - Lifetime
- 2002-10-16 HR HR20040409A patent/HRP20040409A2/hr not_active Application Discontinuation
- 2002-10-16 DE DE60233884T patent/DE60233884D1/de not_active Expired - Lifetime
- 2002-10-16 CA CA002463469A patent/CA2463469A1/en not_active Abandoned
- 2002-10-16 WO PCT/US2002/032834 patent/WO2003032981A1/en not_active Ceased
- 2002-10-16 MX MXPA04003516A patent/MXPA04003516A/es active IP Right Grant
- 2002-10-16 BR BR0213660-0A patent/BR0213660A/pt not_active IP Right Cessation
- 2002-10-16 IL IL16131702A patent/IL161317A0/xx unknown
- 2002-10-16 RU RU2004115333/04A patent/RU2340600C2/ru not_active IP Right Cessation
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2004
- 2004-04-15 CO CO04034582A patent/CO5570674A2/es not_active Application Discontinuation
- 2004-04-15 ZA ZA200402856A patent/ZA200402856B/en unknown
- 2004-05-14 NO NO20042024A patent/NO20042024L/no not_active Application Discontinuation
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2005
- 2005-07-22 US US11/186,958 patent/US20050272803A1/en not_active Abandoned
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2008
- 2008-06-16 RU RU2008123376/04A patent/RU2008123376A/ru not_active Application Discontinuation
- 2008-12-01 US US12/325,433 patent/US20090176799A1/en not_active Abandoned
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2009
- 2009-09-07 JP JP2009205533A patent/JP2009286797A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20050272803A1 (en) | 2005-12-08 |
| ATE444065T1 (de) | 2009-10-15 |
| RU2008123376A (ru) | 2009-12-27 |
| RU2340600C2 (ru) | 2008-12-10 |
| KR20050037404A (ko) | 2005-04-21 |
| US20090176799A1 (en) | 2009-07-09 |
| CO5570674A2 (es) | 2005-10-31 |
| CA2463469A1 (en) | 2003-04-24 |
| BR0213660A (pt) | 2004-08-24 |
| EP1435944B1 (en) | 2009-09-30 |
| AU2002335015B8 (en) | 2006-11-30 |
| JP4484515B2 (ja) | 2010-06-16 |
| DE60233884D1 (de) | 2009-11-12 |
| US20030139406A1 (en) | 2003-07-24 |
| EP1435944A1 (en) | 2004-07-14 |
| KR100951218B1 (ko) | 2010-04-05 |
| ES2334650T3 (es) | 2010-03-15 |
| US7235579B2 (en) | 2007-06-26 |
| RU2004115333A (ru) | 2005-10-27 |
| WO2003032981A1 (en) | 2003-04-24 |
| NO20042024L (no) | 2004-05-14 |
| JP2005508961A (ja) | 2005-04-07 |
| CN1604776A (zh) | 2005-04-06 |
| JP2009286797A (ja) | 2009-12-10 |
| NZ532288A (en) | 2005-12-23 |
| ZA200402856B (en) | 2005-01-25 |
| HRP20040409A2 (en) | 2005-06-30 |
| IL161317A0 (en) | 2004-09-27 |
| MXPA04003516A (es) | 2004-07-23 |
| AU2002335015B2 (en) | 2006-11-02 |
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