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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Inventor
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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    • C07D295/04Heterocyclic 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
    • C07D295/14Heterocyclic 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
    • C07D295/145Heterocyclic 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
    • C07D295/15Heterocyclic 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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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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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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US20060025416A1 (en) 2006-02-02
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ATE457301T1 (de) 2010-02-15
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