ES2342783T3 - Aril aciltioureas sustituidas y compuestos relacionados, inhibidores de la replicacion viral. - Google Patents

Aril aciltioureas sustituidas y compuestos relacionados, inhibidores de la replicacion viral. Download PDF

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Publication number
ES2342783T3
ES2342783T3 ES05856726T ES05856726T ES2342783T3 ES 2342783 T3 ES2342783 T3 ES 2342783T3 ES 05856726 T ES05856726 T ES 05856726T ES 05856726 T ES05856726 T ES 05856726T ES 2342783 T3 ES2342783 T3 ES 2342783T3
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thiourea
phenyl
pentyloxy
carbonyl
trifluoromethyl
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Avinash Phadke
Dawei Chen
Milind Deshpande
Andrew Thurkauf
Xiangzhu Wang
Yiping Shen
Liu Cuixian
Quinn Jesse
Shouming Li
Junko Ohkanda
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Achillion Pharmaceuticals Inc
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Achillion Pharmaceuticals Inc
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    • 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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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    • C07D211/40—Oxygen atoms
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    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4
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    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract

Un compuesto o sal farmacéuticamente aceptable del mismo, en que el compuesto es: 1-(4-pentilfenil)-3-(1,2,3-tiadiazol-4-carbonil)-tiourea; 1-(3-(4-fenil-benciloxi)fenil)-3-(2-morfolinoacetil)-tiourea; 1-(3-cianobenzoil)-3-(3-benciloxi-fenil)-tiourea; 1-(1-metilpiperidino-3-carbonil)-3-(4-pentiloxifenil)-tiourea; 1-(1-metilpiperidino-3-carbonil)-3-(4-pentilfenil)-tiourea; 1-(4-(pentiloxi)fenil)-3-(quinoxalino-7-carbonil)-tiourea; 1-(4-pentilfenil)-3-(quinolino-3-carbonil)-tiourea; 1-(4-(pentiloxi)fenil)-3-(quinoxalino-7-carbonil)-tiourea; 1-(4-pentilfenil)-3-(quinoxalino-7-carbonil)-tiourea; 1-(2-metil-5-(trifluorometil)oxazol-4-carbonil)-3-(4-pentilfenil)-tiourea; 1-(2-metil-5-(trifluorometil)oxazol-4-carbonil)-3-(4-(pentiloxi)fenil)-tiourea; 1-(4-pentilfenil)-3-(1,2,3-tiadiazol-4-carbonil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(H-imidazo[1,2-a]piridino-6-carbonil)-tiourea; 1-(1-(2-amino-2-oxoetil)-2-oxo-1,2-dihidropiridino-5-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(3-ciclopropil-4-(pentiloxi)fenil)-3-nicotinoiltiourea; 1-(1-metil-2-oxo-1,2-dihidropiridino-5-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(4-(hexiloxi)fenil)-3-(1-metil-2-oxo-1,2-dihidropiridino-5-carbonil)-tiourea; 2-oxo-2-(5-((3-(4-(pentiloxi)-3-(trifluorometil)-fenil)tioureido)carbonil)piridin-2-ilamino)acetato de metilo; 2-(5-((3-(4-(heptiloxi)fenil)tioureido)carbonil)-piridin-2-ilamino)-2-oxoacetato de metilo; 1-(2-(2-amino-2-oxoacetamido)nicotinoil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(5-metil-4,5,6,7-tetrahidrofuro[3,2-c]piridino-2-carbonil)-3-(4-(pentiloxi)fenil)-tiourea; 1-(2-(1H-imidazol-1-il)acetil)-3-(4-(pentiloxi)fenil)-tiourea; 1-(4-(pentiloxi)fenil)-3-(3-(piridin-3-il)propanoil)-tiourea; 1-(3-fluoro-4-(4-fenilpiperidin-1-il)fenil)-3-nicotinoiltiourea; 1-(4-(ciclohexilmetoxi)-3-fluorofenil)-3-nicotinoiltiourea; 1-(4-(4-hexilbiciclo[2.2.2]octan-1-il)fenil)-3-nicotinoiltiourea; 1-nicotinoil-3-(4-((1s,4r)-4-propilciclohexil)fenil)-tiourea; 1-(4-((1s,4r)-4-hexilciclohexil)fenil)-3-nicotinoiltiourea; 1-(3-fenoxifenil)-3-(2-(pirrolidin-1-il)nicotinoil)-tiourea; 1-(3-(benciloxi)fenil)-3-(2-(pirrolidin-1-il)nicotinoil)-tiourea; 1-(6-(pentiloxi)piridin-3-il)-3-(2-(pirrolidin-1-il)nicotinoil)-tiourea; 1-(3-(2,3-dihidro-1H-inden-2-iloxi)fenil)-3-(2-(pirrolidin-1-il)nicotinoil)-tiourea; 1-(6-(2-(dimetilamino)etoxi)nicotinoil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(5-metilisoxazol-3-carbonil)-3-(6-(pentiloxi)piridin-3-il)-tiourea; 1-(4-metil-1,2,3-tiadiazol-5-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(3-terc-butil-1-metil-1H-pirazol-5-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(2-metilnicotinoil)-3-(6-(pentiloxi)piridin-3-il)-tiourea; 1-(1,3-dimetil-1H-pirazol-5-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(6-(pentiloxi)piridin-3-il)-3-(2-(piridin-4-il)tiazol-4-carbonil)-tiourea; 1-(6-(pentiloxi)piridin-3-il)-3-(2-fenil-5-(trifluorometil)oxazol-4-carbonil)-tiourea; 1-(4-(pentiloxi)-3-(trifluorometil)fenil)-3-(2-(piridin-3-il)tiazol-4-carbonil)-tiourea; 1-(2-metil-1,8-naftiridino-3-carbonil)-3-(6-(pentiloxi)piridin-3-il)-tiourea; 1-(2,7-dimetilpirazolo[1,5-a]pirimidino-6-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(2-metil-5-(trifluorometil)oxazol-4-carbonil)-3-(6-(pentiloxi)piridin-3-il)-tiourea; 1-(4-metil-2-fenil-2H-1,2,3-triazol-5-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(5-metilisoxazol-4-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(5-metilisoxazol-3-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(6-(pentiloxi)piridin-3-il)-3-(1,2,3-tiadiazol-4-carbonil)-tiourea; 1-(2-metil-H-imidazo[1,2-a]piridino-3-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(isoxazol-5-carbonil)-3-(6-(pentiloxi)piridin-3-il)-tiourea; 1-(2-metilnicotinoil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(benzo[c][1,2,5]oxadiazol-6-carbonil)-3-(6-(pentiloxi)piridin-3-il)-tiourea; 1-(4-(pentiloxi)-3-(trifluorometil)fenil)-3-(2-(piridin-4-il)tiazol-4-carbonil)-tiourea; 1-(1,3-dimetil-1H-tieno[2,3-c]pirazol-5-carbonil)-3-(6-(pentiloxi)piridin-3-il)-tiourea; 1-(2-metil-1,8-naftiridino-3-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(2-metil-5-(trifluorometil)oxazol-4-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(4-(pentiloxi)-3-(trifluorometil)fenil)-3-(1,2,3-tiadiazol-4-carbonil)-tiourea; 1-(isoxazol-5-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(benzo[c][1,2,5]oxadiazol-6-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(4-metil-1,2,3-tiadiazol-5-carbonil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(4-metil-1,2,3-tiadiazol-5-carbonil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(2-(piridin-3-il)tiazol-4-carbonil)-tiourea; 1-(2,7-dimetilpirazolo[1,5-a]pirimidino-6-carbonil)-3-(3-fluoro-4-(pentiloxi)fenil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(4-metil-2-fenil-2H-1,2,3-triazol-5-carbonil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(5-metilisoxazol-4-carbonil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(5-metilisoxazol-3-carbonil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(2-(piridin-4-il)tiazol-4-carbonil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(2-fenil-5-(trifluorometil)oxazol-4-carbonil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(2-metil-1,8-naftiridino-3-carbonil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(2-metil-5-(trifluorometil)oxazol-4-carbonil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(1,2,3-tiadiazol-4-carbonil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(isoxazol-5-carbonil)-tiourea; 1-(benzo[c][1,2,5]oxadiazol-6-carbonil)-3-(3-fluoro-4-(pentiloxi)fenil)-tiourea; 1-(1,3-dimetil-1H-tieno[2,3-c]pirazol-5-carbonil)-3-(3-fluoro-4-(pentiloxi)fenil)-tiourea; 1-(4-metil-1,2,3-tiadiazol-5-carbonil)-3-(6-(pentiloxi)piridin-3-il)-tiourea; 1-(1,3-dimetil-1H-pirazol-5-carbonil)-3-(6-(pentiloxi)piridin-3-il)-tiourea; 1-(6-(pentiloxi)piridin-3-il)-3-(2-(piridin-3-il)tiazol-4-carbonil)-tiourea; 1-(2,7-dimetilpirazolo[1,5-a]pirimidino-6-carbonil)-3-(6-(pentiloxi)piridin-3-il)-tiourea; 1-(4-metil-2-fenil-2H-1,2,3-triazol-5-carbonil)-3-(6-(pentiloxi)piridin-3-il)-tiourea; 1-(3-(benciloxi)fenil)-3-(6-(4-metilpiperazin-1-il)nicotinoil)-tiourea; 1-(6-(4-metilpiperazin-1-il)nicotinoil)-3-(3-fenoxifenil)-tiourea; 1-(6-(4-metilpiperazin-1-il)nicotinoil)-3-(4-pentilfenil)-tiourea; 1-(6-(4-metilpiperazin-1-il)nicotinoil)-3-(4-(pentiloxi)fenil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(2-(4-metilpiperazin-1-il)nicotinoil)-tiourea; 1-(6-(4-metilpiperazin-1-il)nicotinoil)-3-(6-(pentiloxi)piridin-3-il)-tiourea; 1-(6-(4-metilpiperazin-1-il)nicotinoil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(3-metil-4-(pentiloxi)fenil)-3-(2-(4-metilpiperazin-1-il)nicotinoil)-tiourea; 1-(6-hidroxinicotinoil)-3-(3-fenoxifenil)-tiourea; 1-(6-hidroxinicotinoil)-3-(4-(pentiloxi)fenil)-tiourea; 1-(6-hidroxinicotinoil)-3-(4-pentilfenil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(2-hidroxinicotinoil)-tiourea; 1-(6-hidroxinicotinoil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(6-hidroxinicotinoil)-3-(4-(piperidin-1-il)-3-(trifluorometil)fenil)-tiourea; 1-(4-(metil(pentil)amino)-3-(trifluorometil)fenil)-3-nicotinoiltiourea; 1-(5-hidroxinicotinoil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(5-hidroxinicotinoil)-3-(3-fenoxifenil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(3-hidroxinicotinoil)-tiourea; 1-(4-(pentiloxi)-3-(trifluorometil)fenil)-3-(pirazolo[1,5-a]pirimidino-6-carbonil)-tiourea; 1-(4-(pentiloxi)fenil)-3-(pirazolo[1,5-a]pirimidino-6-carbonil)-tiourea; 1-(4-pentilfenil)-3-(pirazolo[1,5-a]pirimidino-6-carbonil)-tiourea; 1-(3-fenoxifenil)-3-(pirazolo[1,5-a]pirimidino-6-carbonil)-tiourea; 1-(6-(pentiloxi)piridin-3-il)-3-(pirazolo[1,5-a]pirimidino-6-carbonil)-tiourea; 1-(3-fluoro-4-(pentiloxi)fenil)-3-(pirazolo[1,5-a]pirimidino-6-carbonil)-tiourea; 1-(6-(morfolino-4-carbonil)nicotinoil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(6-(morfolino-4-carbonil)nicotinoil)-3-(3-fenoxifenil)-tiourea; 1-(6-((dimetilamino)metil)nicotinoil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(6-acetamidonicotinoil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; acetato de (5-((3-(4-(pentiloxi)-3-(trifluorometil)fenil)tioureido)carbonil)piridin-2-il)metilo; 1-(6-(hidroximetil)nicotinoil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-nicotinoil-3-(3-(trifluorometil)-4-(4-(trifluorometil)piperidin-1-il)fenil)-tiourea; 1-(3-fluoro-4-(4-(trifluorometil)piperidin-1-il)fenil)-3-nicotinoiltiourea; 1-(6-(morfolino-4-carbonil)nicotinoil)-3-(2-fenilbenzo[d][1,3]dioxol-5-il)-tiourea; 1-(6-(morfolinometil)nicotinoil)-3-(4-(pentiloxi)fenil)-tiourea; 1-(6-(morfolinometil)nicotinoil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(6-((dimetilamino)metil)nicotinoil)-3-(4-pentilfenil)-tiourea; 1-(3-(benciloxi)fenil)-3-(2-((dimetilamino)metil)nicotinoil)-tiourea; 1-(6-((dimetilamino)metil)nicotinoil)-3-(3-fenoxifenil)-tiourea; 1-(4-(heptiloxi)fenil)-3-(2-(morfolino-4-carbonil)nicotinoil)-tiourea; 1-(6-(morfolino-4-carbonil)nicotinoil)-3-(4-(octiloxi)fenil)-tiourea; 1-(6-(morfolino-4-carbonil)nicotinoil)-3-(3-fenoxifenil)-tiourea; 1-(6-(morfolino-4-carbonil)nicotinoil)-3-(4-pentilfenil)-tiourea; 1-(4-(heptiloxi)fenil)-3-(2-((4-metilpiperazin-1-il)metil)nicotinoil)-tiourea; 1-(6-((4-metilpiperazin-1-il)metil)nicotinoil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(6-((dimetilamino)metil)nicotinoil)-3-(4-(pentiloxi)fenil)-tiourea; 1-(2-oxo-2H-piran-5-carbonil)-3-(4-(pentiloxi)-3-(trifluorometil)fenil)-tiourea; 1-(4-(heptiloxi)fenil)-3-(2-hidroxinicotinoil)-tiourea; 1-(6-((dimetilamino)metil)nicotinoil)-3-(4-(hexiloxi)fenil)-tiourea; 1-(6-((dimetilamino)metil)nicotinoil)-3-(2-fenilbenzo[d][1,3]dioxol-5-il)-tiourea; 1-(6-(morfolinometil)nicotinoil)-3-(3-fenoxifenil)-tiourea; 1-(4-(hexiloxi)fenil)-3-(2-(morfolinometil)-nicotinoil)-tioure
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JP4109271B2 (ja) 2008-07-02
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ATE457301T1 (de) 2010-02-15
US7767706B2 (en) 2010-08-03
AP2006003808A0 (en) 2006-12-31
US20090023730A1 (en) 2009-01-22
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US7365068B2 (en) 2008-04-29
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