CA2579291C - Processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines - Google Patents

Processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines Download PDF

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Publication number
CA2579291C
CA2579291C CA2579291A CA2579291A CA2579291C CA 2579291 C CA2579291 C CA 2579291C CA 2579291 A CA2579291 A CA 2579291A CA 2579291 A CA2579291 A CA 2579291A CA 2579291 C CA2579291 C CA 2579291C
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Prior art keywords
formula
compound
alkyl
hydrogen
group
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Expired - Lifetime
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CA2579291A
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English (en)
French (fr)
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CA2579291A1 (en
Inventor
George W. Muller
Roger Chen
Manohar Tukaram Saindane
Chuansheng Ge
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Celgene Corp
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Celgene Corp
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Application filed by Celgene Corp filed Critical Celgene Corp
Publication of CA2579291A1 publication Critical patent/CA2579291A1/en
Application granted granted Critical
Publication of CA2579291C publication Critical patent/CA2579291C/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Transplantation (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2579291A 2004-09-03 2005-08-31 Processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines Expired - Lifetime CA2579291C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US60740904P 2004-09-03 2004-09-03
US60/607,409 2004-09-03
PCT/US2005/031318 WO2006028964A1 (en) 2004-09-03 2005-08-31 Processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines

Publications (2)

Publication Number Publication Date
CA2579291A1 CA2579291A1 (en) 2006-03-16
CA2579291C true CA2579291C (en) 2011-11-29

Family

ID=35385616

Family Applications (1)

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CA2579291A Expired - Lifetime CA2579291C (en) 2004-09-03 2005-08-31 Processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines

Country Status (22)

Country Link
US (1) US7863451B2 (https=)
EP (2) EP2479172B1 (https=)
JP (2) JP2008512379A (https=)
KR (1) KR20070057907A (https=)
CN (1) CN101080400A (https=)
AR (1) AR050724A1 (https=)
AU (1) AU2005282728A1 (https=)
BR (1) BRPI0514865A (https=)
CA (1) CA2579291C (https=)
ES (2) ES2437592T3 (https=)
GT (1) GT200500242A (https=)
HN (1) HN2005000508A (https=)
IL (1) IL181674A0 (https=)
MX (1) MX2007002521A (https=)
NZ (1) NZ554068A (https=)
PA (1) PA8643901A1 (https=)
PE (1) PE20060648A1 (https=)
SV (1) SV2007002219A (https=)
TW (1) TW200621748A (https=)
UY (1) UY29097A1 (https=)
WO (1) WO2006028964A1 (https=)
ZA (1) ZA200702382B (https=)

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7629360B2 (en) * 1999-05-07 2009-12-08 Celgene Corporation Methods for the treatment of cachexia and graft v. host disease
US7323479B2 (en) * 2002-05-17 2008-01-29 Celgene Corporation Methods for treatment and management of brain cancer using 1-oxo-2-(2,6-dioxopiperidin-3-yl)-4-methylisoindoline
UA83504C2 (en) 2003-09-04 2008-07-25 Селджин Корпорейшн Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione
HRP20130102T1 (hr) * 2005-06-30 2013-03-31 Celgene Corporation Postupak dobivanja spojeva 4-amino-2-(2,6-dioksopiperidin-3-il)izoindolin-1,3-diona
CN101186611B (zh) * 2006-11-15 2011-05-18 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吡咯啉-2-酮衍生物及其制备和应用
CA2717326C (en) * 2008-03-11 2018-10-23 Dr. Reddy's Laboratories Ltd. Preparation of lenalidomide
DE102008057285A1 (de) 2008-11-14 2010-05-20 Ratiopharm Gmbh 3-(4-Amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidindion in Form einer festen Lösung
DE102008057284A1 (de) 2008-11-14 2010-05-20 Ratiopharm Gmbh Tabletten enthaltend Lenalidomid und Adhäsionsverstärker
DE102008057335A1 (de) 2008-11-14 2010-05-20 Ratiopharm Gmbh Amorphes Lenalidomid
WO2010056384A1 (en) * 2008-11-17 2010-05-20 Dr. Reddy's Laboratories Ltd. Lenalidomide solvates and processes
WO2010093434A1 (en) 2009-02-11 2010-08-19 Celgene Corporation Isotopologues of lenalidomide
CN102414196A (zh) * 2009-03-02 2012-04-11 基因里克斯(英国)有限公司 改进的方法
CN101580501B (zh) 2009-06-01 2011-03-09 南京卡文迪许生物工程技术有限公司 3-(取代二氢异吲哚酮-2-基)-2,6-哌啶二酮的合成方法及其中间体
EA201270261A1 (ru) * 2009-08-12 2012-07-30 Синтон Б. В. Соли леналидомида
WO2011033468A1 (en) * 2009-09-16 2011-03-24 Ranbaxy Laboratories Limited Process for the preparation of a crystalline form of lenalidomid
TWI475014B (zh) * 2009-09-17 2015-03-01 Scinopharm Taiwan Ltd 固體形態的３－（４－胺基－１－側氧基－１，３－二氫－異吲哚－２－基）－哌啶－２，６－二酮及其製造方法
WO2011050962A1 (en) 2009-10-29 2011-05-05 Ratiopharm Gmbh Acid addition salts of lenalidomide
CN102060842B (zh) * 2009-11-02 2013-05-08 南京卡文迪许生物工程技术有限公司 3-(取代二氢异吲哚-2-基)-2,6-哌啶二酮多晶型物和药用组合物
CN102127054B (zh) * 2009-11-02 2013-04-03 南京卡文迪许生物工程技术有限公司 3-(取代二氢异吲哚-2-基)-2,6-哌啶二酮多晶型物和药用组合物
CN101696205B (zh) * 2009-11-02 2011-10-19 南京卡文迪许生物工程技术有限公司 3-(取代二氢异吲哚-2-基)-2,6-哌啶二酮多晶型物和药用组合物
WO2011069608A1 (en) * 2009-12-09 2011-06-16 Ratiopharm Gmbh S-lenalidomide, polymorphic forms thereof and blend comprising s- und r-lenalidomide
CN101817813B (zh) * 2010-01-15 2013-04-10 南京卡文迪许生物工程技术有限公司 3-(取代二氢异吲哚酮-2-基)-2,6-哌啶二酮晶体ⅳ及其药用组合物
EP2536706B1 (en) * 2010-02-11 2017-06-14 Celgene Corporation Arylmethoxy isoindoline derivatives and compositions comprising and methods of using the same
CN102453021A (zh) * 2010-10-22 2012-05-16 重庆医药工业研究院有限责任公司 来那度胺的新晶型及其制备方法
WO2012079075A1 (en) 2010-12-10 2012-06-14 Concert Pharmaceuticals, Inc. Deuterated phthalimide derivatives
US9540341B2 (en) 2011-07-19 2017-01-10 Amplio Pharma, Llc Crystalline forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione
JP2015524811A (ja) * 2012-07-27 2015-08-27 セルジーン コーポレイション イソインドリン−１，３−ジオン化合物の調製プロセス
ES2712652T3 (es) * 2012-08-09 2019-05-14 Celgene Corp Procesos para la preparación de (S)-3-4-((4-(morfolinometil) bencil) oxi) -1-oxoisoindolin-2il-) piperidin-2, 6-diona y formas farmacéuticas aceptables de las mismas
WO2014110322A2 (en) 2013-01-11 2014-07-17 Concert Pharmaceuticals, Inc. Substituted dioxopiperidinyl phthalimide derivatives
CN103242215A (zh) * 2013-05-27 2013-08-14 合肥医工医药有限公司 一种来那度胺中间体的制备方法
WO2016024286A2 (en) 2014-08-11 2016-02-18 Avra Laboratories Pvt. Ltd. An improved process for synthesis of lenalidomide
CN111205268B (zh) * 2014-10-30 2021-01-26 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
CN104447689B (zh) * 2014-12-22 2016-07-20 上海迈柏医药科技有限公司 来那度胺的晶型及其制备方法
TWI793151B (zh) 2017-08-23 2023-02-21 瑞士商諾華公司 3-(1-氧異吲哚啉-2-基)之氫吡啶-2,6-二酮衍生物及其用途
CN108191826A (zh) * 2018-01-08 2018-06-22 浙江省医学科学院 一种来那度胺晶体及其制备方法
CN118344338A (zh) 2018-04-23 2024-07-16 细胞基因公司 取代的4-氨基异吲哚啉-1,3-二酮化合物以及它们用于治疗淋巴瘤的用途
AR116109A1 (es) 2018-07-10 2021-03-31 Novartis Ag Derivados de 3-(5-amino-1-oxoisoindolin-2-il)piperidina-2,6-diona y usos de los mismos
DK3820573T3 (da) 2018-07-10 2023-10-23 Novartis Ag 3-(5-hydroxy-1-oxoisoindolin-2-yl)piperidin-2,6-dion-derivativer og anvendelse deraf ved behandling af ikaros family zinc finger 2 (ikzf2)-afhængige sygdomme
WO2020048546A1 (zh) * 2018-09-07 2020-03-12 南京明德新药研发有限公司 三环取代哌啶二酮类化合物
JP2022507267A (ja) 2018-11-13 2022-01-18 バイオセリックス， インコーポレイテッド 置換イソインドリノン
CN109369504B (zh) * 2018-12-06 2020-05-12 温州大学 含硫3-亚甲基异吲哚啉-1-酮衍生物的制备方法
WO2025118133A1 (zh) * 2023-12-05 2025-06-12 浙江普洛家园药业有限公司 一种(s)-来那度胺-5-位衍生物及其合成方法和应用

Family Cites Families (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR0166088B1 (ko) 1990-01-23 1999-01-15 . 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도
DE4236880A1 (de) * 1992-10-31 1994-05-05 Basf Ag N-Phenyl substituierte Glutarimide und N-Phenylglutarsäureamide, deren Herstellung und Verwendung
US6114355A (en) 1993-03-01 2000-09-05 D'amato; Robert Methods and compositions for inhibition of angiogenesis
US5629327A (en) 1993-03-01 1997-05-13 Childrens Hospital Medical Center Corp. Methods and compositions for inhibition of angiogenesis
US5463063A (en) 1993-07-02 1995-10-31 Celgene Corporation Ring closure of N-phthaloylglutamines
US5698579A (en) 1993-07-02 1997-12-16 Celgene Corporation Cyclic amides
DE19601303A1 (de) * 1996-01-16 1997-07-17 Boehringer Ingelheim Kg Neuartige Benzoylguanidin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Herstellung von Arzneimitteln
US6281230B1 (en) 1996-07-24 2001-08-28 Celgene Corporation Isoindolines, method of use, and pharmaceutical compositions
US5798368A (en) 1996-08-22 1998-08-25 Celgene Corporation Tetrasubstituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines and method of reducing TNFα levels
NZ333903A (en) * 1996-07-24 2000-02-28 Celgene Corp Substituted 2(2,6-dioxopiperidin-3-yl)phthalimides and -1oxoisoindolines and method of reducing TNF-alpha levels in a mammal
HU228769B1 (en) * 1996-07-24 2013-05-28 Celgene Corp Substituted 2(2,6-dioxopiperidin-3-yl)phthalimides and -1-oxoisoindolines and their use for production of pharmaceutical compositions for mammals to reduce the level of tnf-alpha
US5635517B1 (en) 1996-07-24 1999-06-29 Celgene Corp Method of reducing TNFalpha levels with amino substituted 2-(2,6-dioxopiperidin-3-YL)-1-oxo-and 1,3-dioxoisoindolines
RU2188819C2 (ru) 1996-08-12 2002-09-10 Селджин Корпорейшн НОВЫЕ ИММУНОТЕРАПЕВТИЧЕСКИЕ СОЕДИНЕНИЯ, СОДЕРЖАЩАЯ ИХ ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ И СПОСОБ СНИЖЕНИЯ УРОВНЕЙ ФДЭ, TNFα И NFκB
US5874448A (en) 1997-11-18 1999-02-23 Celgene Corporation Substituted 2-(2,6 dioxo-3-fluoropiperidin-3-yl)-isoindolines and method of reducing TNFα levels
US5955476A (en) 1997-11-18 1999-09-21 Celgene Corporation Substituted 2-(2,6-dioxo-3-fluoropiperidin-3-yl)-isoindolines and method of reducing inflammatory cytokine levels
EP1064277B1 (en) 1998-03-16 2005-06-15 Celgene Corporation 2-(2,6-dioxopiperidin-3-yl)isoindoline derivatives, their preparation and their use as inhibitors of inflammatory cytokines
KR100672892B1 (ko) 1999-03-18 2007-01-23 셀진 코오퍼레이션 치환된 1-옥소- 및 1,3-디옥소이소인돌린스 및 염증성사이토킨 수치를 감소시키기 위한 약학적 조성물로서의이들의 사용
EP1193248A1 (en) * 2000-09-30 2002-04-03 Aventis Pharma Deutschland GmbH Malonamid and malonamic ester derivatives with antithrombotic activity, their preparation and their use
US6458810B1 (en) 2000-11-14 2002-10-01 George Muller Pharmaceutically active isoindoline derivatives
AU2002253795B2 (en) 2000-11-30 2007-02-01 The Children's Medical Center Corporation Synthesis of 4-Amino-Thalidomide enantiomers
US20030045552A1 (en) 2000-12-27 2003-03-06 Robarge Michael J. Isoindole-imide compounds, compositions, and uses thereof
US7091353B2 (en) 2000-12-27 2006-08-15 Celgene Corporation Isoindole-imide compounds, compositions, and uses thereof
JP2002284761A (ja) * 2001-01-17 2002-10-03 Toray Ind Inc 光学活性３−アミノピロリジン−２，５−ジオン誘導体および光学活性３−アミノピロリジン誘導体の製造方法
WO2003014315A2 (en) * 2001-08-06 2003-02-20 The Children's Medical Center Corporation Synthesis and anti-tumor activity of nitrogen substituted thalidomide analogs
EP1485100B1 (en) 2002-03-15 2010-05-05 Vertex Pharmaceuticals Incorporated Azinylaminoazoles as inhibitors of protein kinases
US7968569B2 (en) 2002-05-17 2011-06-28 Celgene Corporation Methods for treatment of multiple myeloma using 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione
US7189740B2 (en) 2002-10-15 2007-03-13 Celgene Corporation Methods of using 3-(4-amino-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione for the treatment and management of myelodysplastic syndromes
US20040091455A1 (en) 2002-10-31 2004-05-13 Zeldis Jerome B. Methods of using and compositions comprising immunomodulatory compounds for treatment and management of macular degeneration
US7563810B2 (en) 2002-11-06 2009-07-21 Celgene Corporation Methods of using 3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)-piperidine-2,6-dione for the treatment and management of myeloproliferative diseases
CH696542A5 (de) * 2003-07-09 2007-07-31 Siegfried Ltd Verfahren zur Herstellung von substituierten 2,6-Dioxopiperidin-3-yl-Verbindungen.
HRP20130102T1 (hr) 2005-06-30 2013-03-31 Celgene Corporation Postupak dobivanja spojeva 4-amino-2-(2,6-dioksopiperidin-3-il)izoindolin-1,3-diona
KR20080042158A (ko) 2005-08-31 2008-05-14 셀진 코포레이션 이소인돌-이미드 화합물과 이를 포함하는 조성물 및 이를이용한 방법
PL2076260T3 (pl) 2006-09-15 2011-08-31 Celgene Corp Związki N-metyloaminometylo-izoindolu, kompozycje zawierające te związki, oraz metody ich stosowania
CA2717326C (en) 2008-03-11 2018-10-23 Dr. Reddy's Laboratories Ltd. Preparation of lenalidomide
CN101531653B (zh) 2008-03-13 2014-07-09 峡江和美药业有限公司 3-(4-氨基-1-氧代-1,3-二氢异吲哚-2-基)哌啶-2,6-二酮及其衍生物的盐或盐的多晶型物及其制备和应用

Also Published As

Publication number Publication date
EP2479172B1 (en) 2013-10-09
BRPI0514865A (pt) 2008-06-24
JP5701824B2 (ja) 2015-04-15
EP2479172A1 (en) 2012-07-25
CA2579291A1 (en) 2006-03-16
PE20060648A1 (es) 2006-07-14
EP1797068B1 (en) 2013-10-09
TW200621748A (en) 2006-07-01
IL181674A0 (en) 2007-07-04
ES2437592T3 (es) 2014-01-13
NZ554068A (en) 2009-07-31
HN2005000508A (es) 2010-10-08
US7863451B2 (en) 2011-01-04
CN101080400A (zh) 2007-11-28
ZA200702382B (en) 2008-08-27
KR20070057907A (ko) 2007-06-07
EP1797068A1 (en) 2007-06-20
ES2438725T3 (es) 2014-01-20
AR050724A1 (es) 2006-11-15
JP2008512379A (ja) 2008-04-24
SV2007002219A (es) 2007-03-20
GT200500242A (es) 2006-06-22
UY29097A1 (es) 2006-03-31
PA8643901A1 (es) 2006-05-16
JP2012207040A (ja) 2012-10-25
AU2005282728A1 (en) 2006-03-16
US20060052609A1 (en) 2006-03-09
MX2007002521A (es) 2007-05-09
WO2006028964A1 (en) 2006-03-16

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