FR2869611B1 - Derives de l'acide hexenoique, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique - Google Patents

Derives de l'acide hexenoique, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique

Info

Publication number
FR2869611B1
FR2869611B1 FR0404713A FR0404713A FR2869611B1 FR 2869611 B1 FR2869611 B1 FR 2869611B1 FR 0404713 A FR0404713 A FR 0404713A FR 0404713 A FR0404713 A FR 0404713A FR 2869611 B1 FR2869611 B1 FR 2869611B1
Authority
FR
France
Prior art keywords
processes
preparation
pharmaceutical compositions
compositions containing
acid derivatives
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.)
Expired - Fee Related
Application number
FR0404713A
Other languages
English (en)
Other versions
FR2869611A1 (fr
Inventor
Jean Jacques Zeiller
Herve Dumas
Dangremont Valerie Guyard
Isabelle Berard
Francis Contard
Daniel Guerrier
Gerard Ferrand
Yves Bonhomme
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Sante SAS
Original Assignee
Merck Sante SAS
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to FR0404713A priority Critical patent/FR2869611B1/fr
Application filed by Merck Sante SAS filed Critical Merck Sante SAS
Priority to CA2565187A priority patent/CA2565187C/fr
Priority to DE602005002647T priority patent/DE602005002647T2/de
Priority to ES05730245T priority patent/ES2293563T3/es
Priority to EP05730245A priority patent/EP1742902B1/fr
Priority to PCT/EP2005/003606 priority patent/WO2005105724A1/fr
Priority to JP2007511902A priority patent/JP4819801B2/ja
Priority to US11/579,361 priority patent/US7632846B2/en
Priority to AU2005238142A priority patent/AU2005238142B2/en
Priority to AT05730245T priority patent/ATE374172T1/de
Priority to ARP050101702A priority patent/AR048717A1/es
Publication of FR2869611A1 publication Critical patent/FR2869611A1/fr
Application granted granted Critical
Publication of FR2869611B1 publication Critical patent/FR2869611B1/fr
Priority to US12/507,880 priority patent/US8063067B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/19—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/56—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
FR0404713A 2004-05-03 2004-05-03 Derives de l'acide hexenoique, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique Expired - Fee Related FR2869611B1 (fr)

Priority Applications (12)

Application Number Priority Date Filing Date Title
FR0404713A FR2869611B1 (fr) 2004-05-03 2004-05-03 Derives de l'acide hexenoique, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique
AU2005238142A AU2005238142B2 (en) 2004-05-03 2005-04-06 Hexenoic acid derivatives, processes for the preparation thereof, pharmaceutical compositions comprising them, and therapeutic applications thereof
ES05730245T ES2293563T3 (es) 2004-05-03 2005-04-06 Derivados del acido hexenoico, procesos para su preparacion, composiciones farmaceuticas que los contengan y su aplicacion terapeutica.
EP05730245A EP1742902B1 (fr) 2004-05-03 2005-04-06 Derives de l'acide hexenoique, procedes de preparation de ces derives, compositions pharmaceutiques les contenant et applications therapeutiques associees
PCT/EP2005/003606 WO2005105724A1 (fr) 2004-05-03 2005-04-06 Derives de l'acide hexenoique, procedes de preparation de ces derives, compositions pharmaceutiques les contenant et applications therapeutiques associees
JP2007511902A JP4819801B2 (ja) 2004-05-03 2005-04-06 ヘキセン酸誘導体、その調製方法、それらを含む医薬組成物およびその治療用途
CA2565187A CA2565187C (fr) 2004-05-03 2005-04-06 Derives de l'acide hexenoique, procedes de preparation de ces derives, compositions pharmaceutiques les contenant et applications therapeutiques associees
DE602005002647T DE602005002647T2 (de) 2004-05-03 2005-04-06 Hexensäurederivate, verfahren zu deren herstellung, pharmazeutische zusammensetzungen, die diese enthalten, und therapeutische anwendungen davon
AT05730245T ATE374172T1 (de) 2004-05-03 2005-04-06 Hexensäurederivate, verfahren zu deren herstellung, pharmazeutische zusammensetzungen, die diese enthalten, und therapeutische anwendungen davon
US11/579,361 US7632846B2 (en) 2004-05-03 2005-04-06 Hexenoic acid derivatives, processes for the preparation thereof, pharmaceutical compositions comprising them, and therapeutic applications thereof
ARP050101702A AR048717A1 (es) 2004-05-03 2005-04-29 Derivados de acido hexenoico, procedimientos para su preparacion, composiciones farmaceuticas que los comprenden y sus aplicaciones terapeuticas
US12/507,880 US8063067B2 (en) 2004-05-03 2009-07-23 Hexenoic acid derivatives, processes for the preparation thereof, pharmaceutical compositions comprising them, and therapeutic applications thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0404713A FR2869611B1 (fr) 2004-05-03 2004-05-03 Derives de l'acide hexenoique, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique

Publications (2)

Publication Number Publication Date
FR2869611A1 FR2869611A1 (fr) 2005-11-04
FR2869611B1 true FR2869611B1 (fr) 2006-07-28

Family

ID=34944690

Family Applications (1)

Application Number Title Priority Date Filing Date
FR0404713A Expired - Fee Related FR2869611B1 (fr) 2004-05-03 2004-05-03 Derives de l'acide hexenoique, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique

Country Status (11)

Country Link
US (2) US7632846B2 (fr)
EP (1) EP1742902B1 (fr)
JP (1) JP4819801B2 (fr)
AR (1) AR048717A1 (fr)
AT (1) ATE374172T1 (fr)
AU (1) AU2005238142B2 (fr)
CA (1) CA2565187C (fr)
DE (1) DE602005002647T2 (fr)
ES (1) ES2293563T3 (fr)
FR (1) FR2869611B1 (fr)
WO (1) WO2005105724A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2880887B1 (fr) * 2005-01-14 2009-01-30 Merck Sante Soc Par Actions Si Derives d'hydroxyphenols, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique
AU2007239283B2 (en) * 2006-04-18 2013-02-07 Nippon Chemiphar Co., Ltd. Activating agent for peroxisome proliferator activated receptor delta
FR2909379B1 (fr) * 2006-11-30 2009-01-16 Servier Lab Nouveaux derives heterocycliques,leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
EP2125711B1 (fr) 2007-03-08 2013-11-06 Albireo Ab Derives de l'acide 3-phenylpropionique et leur utilisation dans le traitement des maladies intestinales inflammatoires
LT2277874T (lt) * 2008-04-15 2018-10-10 Nippon Chemiphar Co., Ltd. Peroksisomų proliferatoriaus aktyvuotų receptorių aktyvatorius
CA2770494A1 (fr) * 2009-08-14 2011-02-17 Ronald Barbaras Utilisation des ligands ppar? dans le traitement ou la prevention d'inflammations ou de maladies associees au metabolisme/production energetique
KR101307494B1 (ko) * 2010-07-07 2013-09-11 주식회사 엘지화학 광반응성 작용기를 갖는 화합물, 광반응성 중합체 및 이를 포함하는 배향막
CA2912747C (fr) 2013-06-27 2021-05-04 Lg Life Sciences Ltd. Derives de biaryle en tant qu'agonistes de gpr120
WO2016105118A2 (fr) 2014-12-24 2016-06-30 주식회사 엘지생명과학 Dérivé de biaryle utilisable en tant qu'agoniste du gpr120
KR20200092971A (ko) * 2017-11-15 2020-08-04 닛뽕 케미파 가부시키가이샤 페르옥시솜 증식제 응답성 수용체 활성화제
US11730714B2 (en) * 2017-12-14 2023-08-22 Nmd Pharma A/S Compounds for the treatment of neuromuscular disorders
US11591284B2 (en) 2017-12-14 2023-02-28 Nmd Pharma A/S Compounds for the treatment of neuromuscular disorders

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3378582A (en) * 1964-03-20 1968-04-16 Merck & Co Inc (alpha-phenoxy)-and (alpha-phenylthio)-omegaphenyl-alkanoic acids
US4335249A (en) * 1975-09-03 1982-06-15 Rohm And Haas Company Herbicidal diphenyl ethers, sulfides, sulfoxides and sulfones
IT1212821B (it) * 1983-06-03 1989-11-30 Scharper Spa Derivati dell'acido fenil-etil-acetico ad attivita'antiinfiammatoria.
FR2869610B1 (fr) * 2004-05-03 2006-07-28 Merck Sante Soc Par Actions Si Derives de l'acide pentenoique, procedes pour leur preparation, compositions pharmaceutiques les contenant et leurs applications therapeutiques

Also Published As

Publication number Publication date
JP4819801B2 (ja) 2011-11-24
AU2005238142A1 (en) 2005-11-10
FR2869611A1 (fr) 2005-11-04
CA2565187A1 (fr) 2005-11-10
JP2007536290A (ja) 2007-12-13
ES2293563T3 (es) 2008-03-16
AU2005238142B2 (en) 2011-01-27
DE602005002647D1 (de) 2007-11-08
US7632846B2 (en) 2009-12-15
US8063067B2 (en) 2011-11-22
CA2565187C (fr) 2012-12-18
AR048717A1 (es) 2006-05-17
EP1742902A1 (fr) 2007-01-17
US20080194564A1 (en) 2008-08-14
ATE374172T1 (de) 2007-10-15
DE602005002647T2 (de) 2008-07-17
EP1742902B1 (fr) 2007-09-26
WO2005105724A1 (fr) 2005-11-10
US20090286776A1 (en) 2009-11-19

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