JP5179174B2 - アルドステロンシンターゼ阻害剤としてのテトラヒドロ−イミダゾ［１，５−ａ］ピリジン誘導体 - Google Patents
アルドステロンシンターゼ阻害剤としてのテトラヒドロ−イミダゾ［１，５−ａ］ピリジン誘導体 Download PDFInfo
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- JP5179174B2 JP5179174B2 JP2007513942A JP2007513942A JP5179174B2 JP 5179174 B2 JP5179174 B2 JP 5179174B2 JP 2007513942 A JP2007513942 A JP 2007513942A JP 2007513942 A JP2007513942 A JP 2007513942A JP 5179174 B2 JP5179174 B2 JP 5179174B2
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- Prior art keywords
- imidazo
- tetrahydro
- acid
- pyridine
- alkyl
- 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.)
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- 229940123338 Aldosterone synthase inhibitor Drugs 0.000 title description 2
- KMJZZOUSHSRQSL-UHFFFAOYSA-N 1,2,3,5-tetrahydroimidazo[1,5-a]pyridine Chemical class C1=CCN2CNCC2=C1 KMJZZOUSHSRQSL-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 88
- -1 di - substituted benzofuranyl Chemical group 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
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- KMUVUHGFNQDMQZ-UHFFFAOYSA-N 8-(1-benzothiophen-2-yl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine Chemical compound C1=CC=C2SC(C3CCCN4C=NC=C43)=CC2=C1 KMUVUHGFNQDMQZ-UHFFFAOYSA-N 0.000 claims description 2
- VFZVAZPJLPXRTH-UHFFFAOYSA-N 8-(1-benzothiophen-3-yl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine Chemical compound C1=CC=C2C(C3CCCN4C=NC=C43)=CSC2=C1 VFZVAZPJLPXRTH-UHFFFAOYSA-N 0.000 claims description 2
- VTMJPEQPALQXQW-UHFFFAOYSA-N 8-(1-methylindol-5-yl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine Chemical compound C1CCN2C=NC=C2C1C1=CC=C2N(C)C=CC2=C1 VTMJPEQPALQXQW-UHFFFAOYSA-N 0.000 claims description 2
- MDVZZACEHBUBHI-UHFFFAOYSA-N 8-(2-methyl-1-benzothiophen-3-yl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine Chemical compound C1CCN2C=NC=C2C1C1=C(C)SC2=CC=CC=C21 MDVZZACEHBUBHI-UHFFFAOYSA-N 0.000 claims description 2
- JOEVCOYKDBLOJN-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-2-yl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine Chemical compound C1CCN2C=NC=C2C1C1=C(C)C2=CC=CC=C2S1 JOEVCOYKDBLOJN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
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- 150000001721 carbon Chemical group 0.000 claims 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Landscapes
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- Cardiology (AREA)
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- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH915/04 | 2004-05-28 | ||
| CH9152004 | 2004-05-28 | ||
| PCT/EP2005/052419 WO2005118581A1 (en) | 2004-05-28 | 2005-05-27 | Tetrahydro-imidazo [1,5-a] pyridin derivatives as aldosterone synthase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008501000A JP2008501000A (ja) | 2008-01-17 |
| JP2008501000A5 JP2008501000A5 (enExample) | 2008-07-10 |
| JP5179174B2 true JP5179174B2 (ja) | 2013-04-10 |
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| JP2007513942A Expired - Fee Related JP5179174B2 (ja) | 2004-05-28 | 2005-05-27 | アルドステロンシンターゼ阻害剤としてのテトラヒドロ−イミダゾ［１，５−ａ］ピリジン誘導体 |
| JP2007513939A Pending JP2008500997A (ja) | 2004-05-28 | 2005-05-27 | アロマターゼ阻害剤としての二環式の窒素含有複素環 |
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| Application Number | Title | Priority Date | Filing Date |
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Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8680079B2 (enExample) |
| EP (2) | EP1749005A1 (enExample) |
| JP (2) | JP5179174B2 (enExample) |
| CN (2) | CN1968930A (enExample) |
| AR (2) | AR049126A1 (enExample) |
| BR (2) | BRPI0511621A (enExample) |
| CA (2) | CA2568163A1 (enExample) |
| IL (2) | IL179406A0 (enExample) |
| TW (2) | TW200616623A (enExample) |
| WO (2) | WO2005118540A2 (enExample) |
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| TW200616623A (en) | 2004-05-28 | 2006-06-01 | Speedel Experimenta Ag | Organic compounds |
| WO2006005725A2 (en) * | 2004-07-09 | 2006-01-19 | Speedel Experimenta Ag | N containing condensed heterocycles with antitumor effects |
| TW200804378A (en) * | 2005-12-09 | 2008-01-16 | Speedel Experimenta Ag | Organic compounds |
| AR060225A1 (es) * | 2006-03-31 | 2008-06-04 | Speedel Experimenta Ag | Proceso para preparar 6,7- dihidro-5h-imidazo (1,5-a) piridin -8- ona |
| EP1842543A1 (en) | 2006-04-05 | 2007-10-10 | Speedel Pharma AG | Pharmaceutical composition coprising an aldosterone synthase inhibitor and a mineralcorticoid receptor antagonist |
| TW200808813A (en) * | 2006-04-12 | 2008-02-16 | Speedel Experimenta Ag | Imidazo compounds |
| TW200808812A (en) * | 2006-04-12 | 2008-02-16 | Speedel Experimenta Ag | Imidazo compounds |
| TW200813071A (en) | 2006-04-12 | 2008-03-16 | Speedel Experimenta Ag | Spiro-imidazo compounds |
| KR101690802B1 (ko) * | 2008-07-24 | 2016-12-28 | 메이지 세이카 파루마 가부시키가이샤 | 피리피로펜 ａ 생합성 유전자 |
| GB2477256B (en) * | 2008-11-07 | 2013-12-25 | Univ Sheffield | Determination of predisposition towards subclinical Cushing's syndrome or incidentaloma |
| DK2426124T3 (da) | 2009-05-13 | 2013-09-30 | Meiji Seika Pharma Co Ltd | Fremgangsmåde til fremstilling af pyripyropene derivater |
| JP5420761B2 (ja) | 2009-05-28 | 2014-02-19 | ノバルティス アーゲー | ネプリリシン阻害剤としての置換アミノプロピオン酸誘導体 |
| KR20120041702A (ko) | 2009-05-28 | 2012-05-02 | 노파르티스 아게 | 네프릴리신 억제제로서의 치환된 아미노부티르산 유도체 |
| ES2663351T3 (es) * | 2009-11-17 | 2018-04-12 | Novartis Ag | Derivados de aril-piridina como inhibidores de la aldosterona sintasa |
| JO2967B1 (en) | 2009-11-20 | 2016-03-15 | نوفارتس ايه جي | Acetic acid derivatives of carbamoyl methyl amino are substituted as new NEP inhibitors |
| UA111151C2 (uk) | 2010-03-01 | 2016-04-11 | Мейдзі Сейка Фарма Ко., Лтд. | Спосіб одержання похідних пірипіропену |
| US8673974B2 (en) | 2010-11-16 | 2014-03-18 | Novartis Ag | Substituted amino bisphenyl pentanoic acid derivatives as NEP inhibitors |
| US8877815B2 (en) | 2010-11-16 | 2014-11-04 | Novartis Ag | Substituted carbamoylcycloalkyl acetic acid derivatives as NEP |
| TWI627167B (zh) | 2011-07-08 | 2018-06-21 | 諾華公司 | 用於高三酸甘油酯個體治療動脈粥狀硬化之方法 |
| CN103958478B (zh) * | 2011-11-30 | 2017-08-01 | 霍夫曼-拉罗奇有限公司 | 双环二氢异喹啉‑1‑酮衍生物 |
| UY35144A (es) | 2012-11-20 | 2014-06-30 | Novartis Ag | Miméticos lineales sintéticos de apelina para el tratamiento de insuficiencia cardiaca |
| WO2014126979A1 (en) | 2013-02-14 | 2014-08-21 | Novartis Ag | Substituted bisphenyl butanoic phosphonic acid derivatives as nep (neutral endopeptidase) inhibitors |
| CA2918074A1 (en) | 2013-07-25 | 2015-01-29 | Novartis Ag | Cyclic polypeptides for the treatment of heart failure |
| CA2918077A1 (en) | 2013-07-25 | 2015-01-29 | Novartis Ag | Bioconjugates of synthetic apelin polypeptides |
| JP6471153B2 (ja) * | 2013-10-17 | 2019-02-13 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | アルドステロン合成酵素阻害剤としての新規フェニルジヒドロピリジン誘導体 |
| CN105593212B (zh) * | 2013-10-17 | 2019-06-04 | 豪夫迈·罗氏有限公司 | 作为醛固酮合酶抑制剂的苯基-二氢吡啶衍生物 |
| JP6484616B2 (ja) * | 2013-10-17 | 2019-03-13 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | アルドステロン合成酵素の阻害剤としてのフェニル−ジヒドロピリジン誘導体 |
| AU2016209968B2 (en) | 2015-01-23 | 2018-11-29 | Novartis Ag | Synthetic apelin fatty acid conjugates with improved half-life |
| JOP20190086A1 (ar) | 2016-10-21 | 2019-04-18 | Novartis Ag | مشتقات نافثيريدينون جديدة واستخدامها في معالجة عدم انتظام ضربات القلب |
| EA201992142A1 (ru) | 2017-03-10 | 2020-04-07 | Эмбера Неуротерапеутикс, Инк. | Фармацевтические композиции и их применения |
| UY38072A (es) | 2018-02-07 | 2019-10-01 | Novartis Ag | Compuestos derivados de éster butanoico sustituido con bisfenilo como inhibidores de nep, composiciones y combinaciones de los mismos |
| WO2020110011A1 (en) | 2018-11-27 | 2020-06-04 | Novartis Ag | Cyclic peptides as proprotein convertase subtilisin/kexin type 9 (pcsk9) inhibitors for the treatment of metabolic disorders |
| US20230089867A1 (en) | 2018-11-27 | 2023-03-23 | Novartis Ag | Cyclic pentamer compounds as proprotein convertase subtilisin/kexin type 9 (pcsk9) inhibitors for the treatment of metabolic disorder |
| UY38485A (es) | 2018-11-27 | 2020-06-30 | Novartis Ag | Compuestos tetrámeros cíclicos como inhibidores de proproteína convertasa subtilisina/kexina tipo 9 (pcsk9), método de tratamiento, uso y su preparación |
| WO2023084449A1 (en) | 2021-11-12 | 2023-05-19 | Novartis Ag | Diaminocyclopentylpyridine derivatives for the treatment of a disease or disorder |
| AR127698A1 (es) | 2021-11-23 | 2024-02-21 | Novartis Ag | Derivados de naftiridinona para el tratamiento de una enfermedad o un trastorno |
| WO2024241229A1 (en) | 2023-05-24 | 2024-11-28 | Novartis Ag | Naphthyridinone derivatives for the treatment of a disease or disorder |
| CN117659075B (zh) * | 2023-12-18 | 2025-02-11 | 中国科学院兰州化学物理研究所 | 一种咪唑衍生型柱[5]芳烃手性填料的制备及应用 |
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| US4889861A (en) * | 1982-12-21 | 1989-12-26 | Ciba-Geigy Corp. | Substituted imidazo[1,5-a]pyridine derivatives and other substituted bicyclic derivatives and their use as aromatase inhibitors |
| US4617307A (en) * | 1984-06-20 | 1986-10-14 | Ciba-Geigy Corporation | Substituted imidazo[1,5-A]pyridine derivatives as aromatase inhibitors |
| JPH0670064B2 (ja) | 1986-12-08 | 1994-09-07 | 三井石油化学工業株式会社 | 二環性イミダゾ−ル誘導体 |
| GB8820730D0 (en) * | 1988-09-02 | 1988-10-05 | Erba Carlo Spa | Substituted 5 6 7 8-tetrahydroimidazo/1.5-a/pyridines & process for their preparation |
| US5057521A (en) | 1988-10-26 | 1991-10-15 | Ciba-Geigy Corporation | Use of bicyclic imidazole compounds for the treatment of hyperaldosteronism |
| CA2026792A1 (en) * | 1989-11-01 | 1991-05-02 | Michael N. Greco | (6,7-dihydro-5h-pyrrolo[1,2-c]imidazol-5-yl)- and (5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl) substituted 1h-benzotriazole derivatives |
| DK0625155T3 (da) * | 1992-01-27 | 2001-11-12 | Janssen Pharmaceutica Nv | Pyrroloimidazolyl- og imidazopyridinyl-substituerede 1H-benzimidazolderivater som aromataseinhibitorer |
| US5763611A (en) * | 1992-05-29 | 1998-06-09 | The Procter & Gamble Company | Thio-substituted cyclic phosphonate compounds, pharmaceutical compositions, and methods for treating abnormal calcium and phosphate metabolism |
| AU6015796A (en) * | 1995-06-14 | 1997-01-15 | Yamanouchi Pharmaceutical Co., Ltd. | Fused imidazole derivatives and medicinal composition thereof |
| JPH0971586A (ja) * | 1995-09-07 | 1997-03-18 | Yamanouchi Pharmaceut Co Ltd | 新規な二環性縮合イミダゾール誘導体 |
| US6333335B1 (en) * | 1999-07-23 | 2001-12-25 | Merck & Co., Inc. | Phenyl-protein transferase inhibitors |
| JP2001151696A (ja) * | 1999-11-22 | 2001-06-05 | Keiko Tanaka | アクチニジンから造る腫瘍の増殖ならびに転移抑制酵素と異質なたんぱく細胞の除去剤 |
| AR034854A1 (es) * | 2000-11-17 | 2004-03-24 | Takeda Chemical Industries Ltd | Compuesto de imidazol condensado, prodroga del mismo, composición farmaceutica y agente para reducir androgenos que lo contienen ,metodo para producirlo, sal diastereomerica de dicho compuesto y metodo para producir un compuesto opticamente activo del compuesto |
| US7612088B2 (en) * | 2004-05-28 | 2009-11-03 | Speedel Experimenta Ag | Heterocyclic compounds and their use as aldosterone synthase inhibitors |
| TW200608978A (en) * | 2004-05-28 | 2006-03-16 | Speedel Experimenta Ag | Organic compounds |
| TW200616623A (en) | 2004-05-28 | 2006-06-01 | Speedel Experimenta Ag | Organic compounds |
| TW200716634A (en) * | 2005-05-31 | 2007-05-01 | Speedel Experimenta Ag | Heterocyclic spiro-compounds |
| TW200716105A (en) * | 2005-05-31 | 2007-05-01 | Speedel Experimenta Ag | Imidazole compounds |
| TW200808812A (en) * | 2006-04-12 | 2008-02-16 | Speedel Experimenta Ag | Imidazo compounds |
| TW200813071A (en) * | 2006-04-12 | 2008-03-16 | Speedel Experimenta Ag | Spiro-imidazo compounds |
| TW200808813A (en) * | 2006-04-12 | 2008-02-16 | Speedel Experimenta Ag | Imidazo compounds |
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2005
- 2005-05-27 TW TW094117480A patent/TW200616623A/zh unknown
- 2005-05-27 CN CNA2005800170603A patent/CN1968930A/zh active Pending
- 2005-05-27 CN CNA2005800173175A patent/CN1960991A/zh active Pending
- 2005-05-27 AR ARP050102199A patent/AR049126A1/es unknown
- 2005-05-27 US US11/597,623 patent/US8680079B2/en not_active Expired - Fee Related
- 2005-05-27 AR ARP050102196A patent/AR049125A1/es unknown
- 2005-05-27 CA CA002568163A patent/CA2568163A1/en not_active Abandoned
- 2005-05-27 JP JP2007513942A patent/JP5179174B2/ja not_active Expired - Fee Related
- 2005-05-27 CA CA002568159A patent/CA2568159A1/en not_active Abandoned
- 2005-05-27 TW TW094117477A patent/TW200612947A/zh unknown
- 2005-05-27 WO PCT/EP2005/052416 patent/WO2005118540A2/en not_active Ceased
- 2005-05-27 BR BRPI0511621-0A patent/BRPI0511621A/pt not_active IP Right Cessation
- 2005-05-27 EP EP05752767A patent/EP1749005A1/en not_active Withdrawn
- 2005-05-27 JP JP2007513939A patent/JP2008500997A/ja active Pending
- 2005-05-27 US US11/597,585 patent/US20080076784A1/en not_active Abandoned
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- 2005-05-27 WO PCT/EP2005/052419 patent/WO2005118581A1/en not_active Ceased
- 2005-05-27 EP EP05747969A patent/EP1765777A2/en not_active Withdrawn
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Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0510409A (pt) | 2007-10-23 |
| EP1765777A2 (en) | 2007-03-28 |
| WO2005118581A1 (en) | 2005-12-15 |
| CN1968930A (zh) | 2007-05-23 |
| CA2568159A1 (en) | 2005-12-15 |
| US8680079B2 (en) | 2014-03-25 |
| EP1749005A1 (en) | 2007-02-07 |
| CA2568163A1 (en) | 2005-12-15 |
| TW200616623A (en) | 2006-06-01 |
| JP2008501000A (ja) | 2008-01-17 |
| AR049125A1 (es) | 2006-06-28 |
| WO2005118540A2 (en) | 2005-12-15 |
| IL179406A0 (en) | 2007-05-15 |
| WO2005118540A3 (en) | 2006-02-02 |
| AR049126A1 (es) | 2006-06-28 |
| US20070225232A1 (en) | 2007-09-27 |
| BRPI0511621A (pt) | 2008-01-02 |
| CN1960991A (zh) | 2007-05-09 |
| IL179408A0 (en) | 2007-05-15 |
| US20080076784A1 (en) | 2008-03-27 |
| TW200612947A (en) | 2006-05-01 |
| JP2008500997A (ja) | 2008-01-17 |
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