ES2675022T3 - Inhibidores de indolamina 2,3-dioxigenasa (IDO) - Google Patents
Inhibidores de indolamina 2,3-dioxigenasa (IDO) Download PDFInfo
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- ES2675022T3 ES2675022T3 ES14729491.2T ES14729491T ES2675022T3 ES 2675022 T3 ES2675022 T3 ES 2675022T3 ES 14729491 T ES14729491 T ES 14729491T ES 2675022 T3 ES2675022 T3 ES 2675022T3
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- phenyl
- ureido
- cyclopropancarboxylic acid
- diisobutylamino
- acid
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
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- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
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Abstract
Un compuesto de la Fórmula (I)**Fórmula** caracterizado por que X es**Fórmula** E es NH o CH2; W es CR10; Y es CR11; V es CR12;**Fórmula** es cicloalquilo C3-C8; R1 es arilo, aril-alquilo C1-C10 o alquilo C1-C10; R2 es COOH, heteroarilo o -CONHSO2R14; R3 es H, alquilo C1-C10 o halo; R4 es H, alquilo C1-C10 o halo; R6 es H; R7 y R8 se seleccionan independientemente entre**Fórmula** R10 es H o halo; R11 es H o halo; y R12 es H, alquilo C1-C10 o alquenilo C2-C10; y R14 es CF3, cicloalquilo C3-C8 o alquilo C1-C10; y/o un estereoisómero, un tautómero o una sal del mismo farmacéuticamente aceptable.
Description
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DESCRIPCION
Inhibidores de indolamina 2,3-dioxigenasa (IDO)
Esta solicitud reivindica el beneficio de la Solicitud Provisional de los Estados Unidos No. 61/791,224, presentada el 15 de marzo de 2013.
Campo de la Invención
La invención se refiere en general a compuestos que modulan o inhiben la actividad enzimática de indolamina 2,3- dioxigenasa (IDO), composiciones farmacéuticas que contienen tales compuestos y el udos de tales compuestos en métodos para tratar trastornos proliferativos, tales como cáncer, infecciones virales y/o enfermedades autoinmunes.
Antecedentes de la Invención
El triptofano es un aminoácido el cual es esencial para la proliferación y supervivencia celular. La indolamina-2,3- dioxigenasa es una enzima intracelular que contiene hematina que cataliza la primera etapa y determinante de la velocidad en la degradación del aminoácido esencial L-triptofano a N-formil-cinurenina. La N-formil-cinurenina es entonces metabolizada por etapas múltiples para producir eventualmente nicotinamida adenina dinucleótido (NAD+). Los catabolitos de triptofano producidos a partir de N-formil-cinurenina, tales como cinurenina, se conocen por ser preferencialmente citotóxicos a células-T. De este modo, una sobreexpresión de IDO puede conducir a tolerancia incrementada en el microambiente tumoral. La sobre expresión de IDO ha sido mostrada por ser un factor pronóstico independiente para supervivencia disminuida en pacientes con melanoma, cánceres pancreáticos, colorrectal y endometrial entre otros. Sin embargo, el IDO se ha encontrado por estar implicado en los trastornos neurológicos y psiquiátricos que incluyen trastornos de humor así como también otras enfermedades crónicas caracterizadas por la activación de IDO y supresión de triptofano, tales como infecciones virales, por ejemplo SIDA, enfermedad de Alzheimer, cánceres que incluyen leucemia de células T y cáncer de colon, enfermedades autoinmunes, enfermedades de los ojos tales como cataratas, infecciones bacterianas tales como enfermedad de Lyme, e infecciones estreptocócicas.
Por consiguiente, un agente el cual es seguro y efectivo en la inhibición de la producción de IDO podría ser una adición muy bienvenida al arsenal del especialista.
Los moduladores IDO destinados a usarse en el tratamiento del cáncer y otras enfermedades se describen en los documentos WO 2008/058178 A1 y WO 2007/075598 A2. Las consideraciones con respecto al diseño de inhibidores de IDO se encuentran en Lancellotti et al. (Curr Med Chem 2011, 18 (15): 2205-14).
Breve Descripción de la Invención
La presente invención proporciona compuestos y/o sales de los mismos farmacéuticamente aceptables, estereoisómeros de los mismos o tautómeros de los mismos, como se define en las reivindicaciones. Además, se describen en el presente documento métodos para modular o inhibir la actividad enzimática de IDO, y métodos para tratar varias condiciones médicas usando tales compuestos.
También se descroben en el presente documento procesos e intermediarios para elaborar los compuestos de la presente invención y/o sales de los mismos farmacéuticamente aceptables o estereoisómeros de los mismos o tautómeros de los mismos.
La presente invención también proporciona composiciones farmacéuticas que comprenden un portador farmacéuticamente aceptable y uno o más de los compuestos de la presente invención y/o sales de los mismos farmacéuticamente aceptables o estereoisómeros de los mismos o tautómeros de los mismos.
Los compuestos de la invención y/o sales de los mismos farmacéuticamente aceptables o estereoisómeros de los mismos o tautómeros de los mismos pueden ser usados en el tratamiento y/o profilaxis de trastornos o enfermedades múltiples asociados con la actividad enzimática de la inhibición de IDO, tales como cáncer, infecciones virales, enfermedades autoinmunes, y otros males.
Los compuestos de la invención y/o sales de los mismos farmacéuticamente aceptables o estereoisómeros de los mismos o tautómeros de los mismos pueden ser usados en terapia.
Los compuestos de la invención y/o sales de los mismos farmacéuticamente aceptables o estereoisómeros de los mismos o tautómeros de los mismos pueden ser usados para la manufactura de un medicamento para el tratamiento y/o profilaxis de trastornos o enfermedades múltiples asociados con la actividad enzimática de IDO.
Los compuestos de la invención y/o sales de los mismos farmacéuticamente aceptables o estereoisómeros de los mismos o tautómeros de los mismos pueden ser usados solos, en combinación con otros compuestos de la presente
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invención y/o sales de los mismos farmacéuticamente aceptables o estereoisómeros de los mismos o tautómeros de los mismos, o en combinación con uno o más de otro(s) agente(s).
Otras características y ventajas de la invención serán aparentes a partir de la siguiente descripción detallada y reivindicaciones.
Descripción Detallada de la Invención
I. COMPUESTOS DE LA INVENCIÓN
En un primer aspecto, la presente invención proporciona compuestos de Formula (I)
donde
X es
E es NH o CH2; W es N o CR10;
Y es N o CR11;
V es N o CR12;
es un cicloalquilo C3-C8;
R1 es arilo, aril-alquilo C1-C10, o alquilo C1-C10;
R2 es COOH, heteroarilo o -CONHSO2R14;
R es H, alquilo C1-C10 o halo;
R4 es H, alquilo C1-C10, o halo;
R6 es H;
R7 y R8 se seleccionan independientemente entre
CH3,
5
CF3(CH2)2-
10
o
R9 es
CF3CH2“~CH—ch2 ch3
Claims (11)
- 510152025REIVINDICACIONES1. Un compuesto de la Fórmula (I)caracterizado por que X es
imagen1 imagen2 imagen3 E es NH o CH2; W es CR10;Y es CR11;V es CR12;imagen4 es cicloalquilo C3-C8;R1 es arilo, aril-alquilo C1-C10 o alquilo C1-C10;R2 es COOH, heteroarilo o -CONHSO2R14;R es H, alquilo C1-C10 o halo;R4 es H, alquilo C1-C10 o halo;R6 es H;R7 y R8 se seleccionan independientemente entreimagen5 imagen6 CH3,5imagen7 CF3(CH2)2-,10oimagen8 imagen9 15 R9esimagen10 imagen11 imagen12 imagen13 imagen14 o5imagen15 R10 es H o halo;R11 es H o halo; yR es H, alquilo C1-C10 o alquenilo C2-C10; y 10 R14 es CF3, cicloalquilo C3-C8 o alquilo C1-C10;y/o un estereoisómero, un tautómero o una sal del mismo farmacéuticamente aceptable.51015202530imagen16 en donde X, Eimagen17 R2 , R3, R4, R6 R9 ,10 11 12R , R y R son como se definen en la reivindicación 1;y/o un estereoisómero, un tautómero o una sal del mismo farmacéuticamente aceptable. - 3. El compuesto de conformidad con la Reivindicación 2 caracterizado porque
imagen18 X es NR7R8; E es NH;R2 es COOH,imagen19 o -CONHSO2R14;R3 es H o alquilo C1-C6;R4 es H, alquilo C1-C6 o halo;R6 es como se define en la reivindicación 1; R10 es H;R12 es H; yR es CF3, cicloalquilo C3-C6 o alquilo C1-C6;y/o un estereoisómero, un tautómero o una sal del mismo farmacéuticamente aceptable.5101520253035imagen20 E es NH;X esimagen21 imagen22 R2 es COOH;R3, R4, R5 y R6 son H; yR7 y R8 son como se definen en la reivindicación 1;y/o un estereoisómero, un tautómero o una sal del mismo farmacéuticamente aceptable. - 5. El compuesto de conformidad con la Reivindicación 4, caracterizado porque R7 y R8 son cada uno
imagen23 R9 esimagen24 y/o un estereoisómero, un tautómero o una sal del mismo farmacéuticamente aceptable. - 6. El compuesto de conformidad con la Reivindicación 2, caracterizado porque
imagen25 X es OR1;E es NH;R2 es COOH,^/VTU-V/'imagen26 N=No -CONHSO2R14; R3, R4 y R6 son H;R1 es arilo, aril-alquilo C1-C6 o alquilo C1-C6;R9 es arilo o alquil arilo C1-C6;R es H, alquilo C1-C6, alquenilo C2-C6 o halo; y R14 es como se define en la reivindicación 1;5y/o un estereoisómero, un tautómero o una sal del mismo farmacéuticamente aceptable.10 - 7. El compuesto de conformidad con la Reivindicación 2, caracterizado porque E es CH2;
imagen27 X es -NR7R8;R2 es COOH; y15 R3, R4, R6, R7 y R8 son como se definen en la Reivindicación 1;y/o un estereoisómero, un tautómero o una sal del mismo farmacéuticamente aceptable.20 - 8. El compuesto de conformidad con la Reivindicación 7, caracterizado porque R7 y R8 son cada unoh3cxJcH—CH2 h3c25YR9 es
imagen28 y/o un estereoisómero, un tautómero o una sal del mismo farmacéuticamente aceptable.30 9. El compuesto de conformidad con la Reivindicación 1 seleccionado entre el grupo que consiste en:ácido 2-(4-(diisobutilamino)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico,ácido 2-(3-(3-(4-clorofenil)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido 2-(4-(diisobutilamino)-3-(3-(4-(trifluorometil)fenil)ureido)fenil)ciclopropancarboxílico,35 ácido 2-(4-(diisobutilamino)-3-(3-(4-fluorofenil)ureido)fenil)ciclopropancarboxílico,ácido 2-(3-(3-(2,4-difluorofenil)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico, ácido 2-(4-(diisobutilamino)-3-(3-(2-fluorofenil)ureido)fenil)ciclopropancarboxílico, ácido 2-(3-(3-(4-ciclopropilfenil)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico, ácido 2-(4-(diisobutilamino)-2-fluoro-5-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico,40 ácido 2-(4-(diisobutilamino)-2-fluoro-5-(3-(6-metilpiridin-3-il)ureido)fenil)ciclopropancarboxílico,ácido 2-(4-(diisobutilamino)-2-fluoro-5-(3-(3-metilisoxazol-5-il)ureido)fenil)ciclopropancarboxílico, ácido 2-(4-(diisobutilamino)-3-(3-(3-metilisoxazol-5-il)ureido)fenil)ciclopropancarboxílico, ácido 2-(4-(diisobutilamino)-3-(3-(6-(trifluorometil)piridin-3-il)ureido)fenil)ciclopropancarboxílico, ácido 2-(4-(diisobutilamino)-3-(3-(6-fluoropiridin-3-il)ureido)fenil)ciclopropancarboxílico,45 ácido 2-(3-(3-(3-ciclopropilisoxazol-5-il)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido 2-(4-(diisobutilamino)-3-(3-(3-(trifluorometil)isoxazol-5-il)ureido)fenil)ciclopropancarboxílico, ácido 2-(5-(3-(4-cloro-2-fluorofenil)urcido)-4-(diisobutilamino)-2-fluorofenil)ciclopropancarboxílico, ácido 2-(4-(diisobutilamino)-2-fluoro-5-(3-(2-fluorofenil)ureido)fenil)ciclopropancarboxílico, ácido 2-(4-(diisobutilamino)-3-(3-(6-metilpiridin-3-il)ureido)fenil)ciclopropancarboxílico,50 ácido 2-(4-((4-clorobencil)(2-metoxietil)amino)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico,ácido 2-(4-((4-clorobencil)(2-metoxietil)amino)-3-(3-(2-fluorofenil)ureido)fenil)ciclopropancarboxílico,ácido 2-(4-(ciclohexil(isobutil)amino)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico,ácido 2-(4-(ciclohexil(isobutil)amino)-3-(3-(3-metilisoxazol-5-il)ureido)fenil)ciclopropancarboxílico,5101520253035404550556065ácido 2-(4-(diisobutilamino)-3-(3-(p-tolil)ureido)fenil)-1-metilciclopropancarboxílico,ácido 3-(4-(diisobutilamino)-3-(3-(p-tolil)ureido)fenil)-2,2-difluorociclopropancarboxílico,2-(1H-tetrazol-5-il)ciclopropil)-2-(diisobutilamino)fenil)-3-(p-tolil)urea,ácido 3-(4-(diisobutilamino)-3-(3-(p-tolil)ureido)fenil)-2,2-dimetilciclopropancarboxílico,ácido 3-(4-(diisobutilamino)-3-(3-(2-fluorofenil)ureido)fenil)-2,2-dimetilciclopropancarboxílico,ácido 2-(3-butil-5-(3-(2-fluorofenil)ureido)-4-propoxifenil) ciclopropancarboxílico,2-(1H-tetrazol-5-il)ciclopropil)-3-butil-2-propoxifenil)-3-(p-tolil)urea,2-(1H-tetrazol-5-il)ciclopropil)-3-butil-2-propoxifenil)-3-(2-fluorofenil)urea,ácido 2-(4-(ciclohexil(4,4,4-trifluoro-2-metilbutil)amino)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico, ácido 2-(4-(ciclohexil(4,4,4-trifluoro-2-metilbutil)amino)-3-(3-(pirimidin-5-il)ureido)fenil)ciclopropancarboxílico, ácido 2-(4-(ciclohexil(4,4,4-trifluoro-2-metilbutil)amino)-3-(3-(5-metilisoxazol-3-il)ureido)fenil)ciclopropancarboxílico,ácido 2-(4-(ciclohexil(4,4,4-trifluoro-2-metilbutil)amino)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico, ácido 2-(4-(ciclohexil(4,4,4-trifluoro-2-metilbutil)amino)-3-(3-(pirimidin-5-il)ureido)fenil)ciclopropancarboxílico, ácido 2-(4-(ciclohexil(4,4,4-trifluoro-2-metilbutil)amino)-3-(3-(5-metilisoxazol-3-il)ureido)fenil)ciclopropancarboxílico,ácido 2-(4-(ciclohexil(4,4,4-trifluoro-2-metilbutil)amino)-3-(2-(p-tolil)acetamido)fenil)ciclopropancarboxílico, ácido 2-(4-(ciclohexil(4,4,4-trifluoro-2-metilbutil)amino)-3-(2-(p-tolil)acetamido)fenil)ciclopropancarboxílico, ácido 2-(4-(diisobutilamino)-3-(3-o-tolilureido)fenil) ciclopropancarboxílico, ácido and 2-(4-(diisobutilamino)-3-(3-p-tolilureido)fenil)ciclopentancarboxílico,y los enantiómeros (1S, 2R) y (1R, 2S) de los mismos; o un compuesto seleccionado entre el grupo que consiste en:ácido (1R,2S)-2-(4-(diisobutilamino)-3-(3-(3-fenilisoxazol-5-il)ureido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(diisobutilamino)-3-(3-(3,4-dimetilisoxazol-5-il)ureido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(diisobutilamino)-3-(2-(p-tolil)acetamido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(diisobutilamino)-3-(2-(3-metilisoxazol-5il)acetamido)fenil) ciclopropancarboxílico,ácido (1S,2R)-2-(4-(diisobutilamino)-3-(2-(p-tolil)acetamido)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(diisobutilamino)-3-(2-(3-metilisoxazol-5-il)acetamido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(diisobutilamino)-3-(3-(pirimidin-5-il)ureido)fenil) ciclopropancarboxílico,ácido (1S,2R)-2-(4-(diisobutilamino)-3-(3-(pirimidin-5-il)ureido)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(diisobutilamino)-3-(3-(quinoxalin-6-il)ureido)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(diisobutilamino)-3-(3-(5-metilisoxazol-3-il)ureido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(diisobutilamino)-3-(3-(5-metilisoxazol-3-il)ureido)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(3-(3-(6-cianopiridin-3-il)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(3-(3-(benzo[c][1,2,5]oxadiazol-5-il)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(diisobutilamino)-3-(3-(4-((etoxicarbonil)amino)fenil)ureido)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(diisobutilamino)-3-(3-(4-(2,2,2-trifluoroetoxi)fenil)ureido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(ciclohexil(4,4,4-trifluorobutil)amino)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(ciclohexil(4,4,4-trifluorobutil)amino)-3-(3-(5-metilisoxazol-3-il)ureido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(ciclohexil(4,4,4-trifluorobutil)amino)-3-(3-pirimidina-5-il)ureido)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(ciclohexil(4,4,4-trifluorobutil)amino)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico,ácido (1 S,2R)-2-(4-(diisobutilamino)-3-(3-(2-metilpirimidin-5-il)ureido)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(3-(3-(2-cianopirimidin-5-il)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(3-(3-(2-cianopirimidin-5-il)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(ciclohexil(isobutil)amino)-3-(3-(5-metilisoxazol-3-il)ureido)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(ciclohexil(isobutil)amino)-3-(3-(5-metilisoxazol-3-il)ureido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(ciclohexyl(isobutil)amino)-3-(3-(pirimidin-5-il)ureido)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(ciclohexil(isobutil)amino)-3-(3-(pirimidin-5-il)ureido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-((1R,2R,4S)-biciclo[2.2.1]heptan-2-il(isobutil)amino)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-((1R,2R,4S)-biciclo[2.2.1]heptan-2-il(isobutil)amino)-3-(3-(pirimidin-5-il)ureido)fenil)ciclopropancarboxílico,(1R,2S)-2-(4-((1R,2R,4S)-biciclo[2.2.1]heptan-2-il(isobutil)amino)-3-(3-(5-metilisoxazol-3-il)ureido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(ciclohexil(3,3,3-trifluoropropil)amino)-3-(3-(pirimidin-5-il)ureido)fenil)ciclopropancarboxílico, ácido (1R,2S)-2-(4-(ciclohexil(3,3,3-trifluoropropil)amino)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico, ácido (1R,2S)-2-(3-(3-(2-cianopirimidin-5-il)ureido)-4-(ciclohexil(3,3,3-trifluoropropil)amino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(ciclohexil(3,3,3-trifluoropropil)amino)-3-(3-(5-metilisoxazol-3-il)ureido)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(ciclohexil(3,3,3-trifluoropropil)amino)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(ciclohexil(3,3,3-trifluoropropil)amino)-3-(3-(5-metilisoxazol-3-il)ureido)fenil)ciclopropancarboxílico,ácido (1 R,2S)-2-(3-(3-(2-cianopirimidin-5-il)ureido)-4-(ciclohexil(isobutil)amino)fenil)ciclopropancarboxílico,5101520253035404550556065ácido (1R,2S)-2-(4-(ciclohexil(isobutil)amino)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico, ácido (1S,2R)-2-(3-(3-(2-cianopirimidin-5-il)ureido)-4-(ciclohexil(isobutil)amino)fenil)ciclopropancarboxílico, ácido (1R,2S)-2-(4-(ciclohexil(isobutil)amino)-2-fluoro-5-(3-(5-metilisoxazol-3-il)ureido)fenil)ciclopropancarboxílico, ácido (1R,2S)-2-(4-(ciclohexil(isobutil)amino)-2-fluoro-5-(3-(3-metilisoxazol-5-il)ureido)fenil)ciclopropancarboxílico, ácido (1R,2S)-2-(4-(ciclohexil(isobutil)amino)-2-fluoro-5-(3-(pirimidin-5-il)ureido)fenil) ciclopropancarboxílico, ácido (1R,2S)-2-(4-(ciclohexil(isobutil)amino)-2-fluoro-5-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico, ácido (1R,2S)-2-(4-(ciclohexil(isobutil)amino)-5-(3-(4-etoxifenil)ureido)-2-fluorofenil)ciclopropancarboxílico, ácido (1R,2S)-2-(5-(3-(benzo[d][1,3]dioxol-5-il)ureido)-4-(ciclohexil-(isobutil)amino)-2-fluorofenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(ciclohexil(isobutil)amino)-2-fluoro-5-(3-(5-metilisoxazol-3-il)ureido)fenil)ciclopropancarboxílico, ácido (1S,2R)-2-(4-(ciclohexil(isobutil)amino)-2-fluoro-5-(3-(pirimidin-5-il)ureido)fenil)ciclopropancarboxílico, ácido (1S,2R)-2-(4-(ciclohexil(isobutil)amino)-2-fluoro-5-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico, ácido (1S,2R)-2-(4-(ciclohexil(isobutil)amino)-5-(3-(4-etoxifenil)ureido)-2-fluorofenil)ciclopropancarboxílico, ácido (1S,2R)-2-(5-(3-(benzo[d][1,3]dioxol-5-il)ureido)-4-(ciclohexil(isobutil)amino)-2-fluorofenil)ciclopropancarboxílico,ácido (1R,2S)-2-(3-(2-(4-cianofenil)acetamido)-4-(ciclohexil(3,3,3-trifluoropropil)amino)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(3-(2-(4-cianofenil)acetamido)-4-(ciclohexil(3,3,3-trifluoropropil)amino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(3-(2-(4-cianofenil)acetamido)-4-(ciclohexil(isobutil)amino)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(3-(2-(4-cianofenil)acetamido)-4-(ciclohexil(isobutil)amino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(diisobutilamino)-3-(2-(4-fluorofenil)acetamido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(diisobutilamino)-3-(2-(6-metilpiridin-3-il)acetamido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(3-(2-(4-clorofenil)acetamido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(3-(2-(4-cianofenil)acetamido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(diisobutilamino)-3-(2-(4-metoxifenil) acetamido)fenil)ciclopropancarboxílico,(1S,2R)-2-(4-(diisobutilamino)-3-(3-(p-tolil)ureido)fenil)-N-(metilsulfonil)ciclopropancarboxamida,(1S,2R)-N-(ciclopropilsulfonil)-2-(4-(diisobutilamino)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxamida,ácido (1R,2S)-2-(4-(ciclohexil(isobutil)amino)-3-(3-(3-metilisoxazol-5-il)ureido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(4-(diisobutilamino)-3-(3-(2-(trifluorometil)fenil)ureido)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(3-(3-(2,4-diclorofenil)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(3-(3-(3,4-diclorofenil)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(3-(3-(4-(difluorometoxi)fenil)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(3-(3-(2-clorofenil)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(3-(3-(4-cloro-2,6-difluorofenil)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(3-(3-(4-bromofenil)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(3-(3-(2-cloro-4-metilfenil)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1R,2S)-2-(3-(3-(4-(cianometil)fenil)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(diisobutilamino)-3-(3-(m-tolil)ureido)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(diisobutilamino)-3-(3-fenilureido)fenil)ciclopropancarboxílico,ácido (1S,2R)-2-(4-(diisobutilamino)-3-(3-(4-etoxifenil)ureido)fenil)ciclopropancarboxílico, yácido (1S,2R)-2-(3-(3-(4-cloro-2-fluorofenil)ureido)-4-(diisobutilamino)fenil)ciclopropancarboxílico. - 10. Un compuesto seleccionado entre el grupo que consiste en:ácido 2-(4-(1-fenilpropoxi)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico,ácido 2-(4-(1-(4-clorofenil)butoxi)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico,ácido 2-(4-(1-fenilbutoxi)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico,ácido 2-(3-butil-5-(3-(p-tolil)ureido)-4-(4,4,4-trifluorobutoxi)fenil)ciclopropancarboxílico,ácido 2-(3-butil-5-(3-(2-fluorofenil)ureido)-4-(4,4,4-trifluorobutoxi) fenil)ciclopropancarboxílicoy los enantiómeros (1S, 2R) y (1R, 2S) de los mismos; o un compuesto selecionado entre el grupo que consiste en:ácido (1S,2R)-2-(4-((S)-1-fenilpropoxi)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico y ácido (1R,2S)-2-(4-((R)-1- fenilpropoxi)-3-(3-(p-tolil)ureido)fenil)ciclopropancarboxílico.
- 11. El compuesto de conformidad con la Reivindicación 1, caracterizado porque el IC50 en el ensayo IDO-1 humano de HEK es < 10 nM.
- 12. Una composición farmacéutica caracterizada porque comprende uno o más compuestos y/o un estereoisómero, un tautómero o una sal del mismo farmacéuticamente aceptable de conformidad con cualquiera de las reivindicaciones 1-11, y un portador o un diluyente farmacéuticamente aceptables.
- 13. Un compuesto y/o un estereoisómero, un tautómero o una sal del mismo farmacéuticamente aceptable de conformidad con cualquiera de las reivindicaciones 1-11, para uso en terapia.
- 14. Un compuesto y/o un estereoisómero, un tautómero o una sal del mismo farmacéuticamente aceptable de conformidad con cualquiera de las reivindicaciones 1-11, para su uso en el tratamiento de cáncer, infecciones virales, depresión, rechazo al transplante de órgano o una enfermedad autoinmune.5 15. El compuesto y/o un estereoisómero, un tautómero o una sal del mismo farmacéuticamente aceptable para subuso en el tratamiento de la reivindicación 14, en donde tal cáncer se selecciona a partir de cáncer de colon, cáncer pancreático, cáncer de mama, cáncer de próstata, cáncer de pulmón, cáncer de ovario, cáncer cervical, cáncer renal, cáncer de cabeza y cuello, linfoma, leucemia y melanoma.
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FR2810979B1 (fr) * | 2000-06-29 | 2002-08-23 | Adir | Nouveaux derives de diphenyluree, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
WO2002046146A1 (fr) * | 2000-12-05 | 2002-06-13 | Kyorin Pharmaceutical Co., Ltd. | Derives d'acide carboxylique substitues |
JP5294874B2 (ja) * | 2005-12-20 | 2013-09-18 | インサイト・コーポレイション | インドールアミン2,3−ジオキシゲナーゼのモジュレーターとしてのn−ヒドロキシアミジノヘテロ環 |
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CN101429151B (zh) | 2008-12-04 | 2011-01-19 | 同济大学 | 一种含(E)-4-(β-溴乙烯基)苯氧酰基结构的IDO抑制剂及其制备方法 |
CN101812008A (zh) * | 2010-05-10 | 2010-08-25 | 苏州康正生物医药有限公司 | 一种含吡咯-2-甲酸芳香酯结构的ido抑制剂及制备方法 |
CN102532144B (zh) | 2012-01-20 | 2014-09-10 | 辽宁思百得医药科技有限公司 | 一种新型吲哚胺-2,3-双加氧酶抑制剂及其制备方法和用途 |
WO2014150646A1 (en) * | 2013-03-15 | 2014-09-25 | Bristol-Myers Squibb Company | Ido inhibitors |
EA029126B1 (ru) * | 2013-07-01 | 2018-02-28 | Бристол-Майерс Сквибб Компани | Ингибиторы ido |
JP6478991B2 (ja) * | 2013-07-11 | 2019-03-06 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | Ido阻害剤 |
CN105658643B (zh) * | 2013-08-27 | 2019-03-01 | 百时美施贵宝公司 | Ido抑制剂 |
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TR201810399T4 (tr) | 2018-08-27 |
WO2014150677A1 (en) | 2014-09-25 |
BR112015021999A2 (pt) | 2017-07-18 |
IL241322A0 (en) | 2015-11-30 |
JP2016519653A (ja) | 2016-07-07 |
AU2014235750B2 (en) | 2018-05-17 |
JP6313416B2 (ja) | 2018-04-18 |
EP2970155A1 (en) | 2016-01-20 |
US20160022619A1 (en) | 2016-01-28 |
CY1120361T1 (el) | 2019-07-10 |
LT2970155T (lt) | 2018-06-25 |
RS57462B1 (sr) | 2018-09-28 |
US9675571B2 (en) | 2017-06-13 |
CN105209443A (zh) | 2015-12-30 |
SG11201506918WA (en) | 2015-09-29 |
KR20150128891A (ko) | 2015-11-18 |
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