AR062881A1 - N-hidroxiamidinoheterociclos como moduladores de indolamina-2,3-dioxigenasa - Google Patents
N-hidroxiamidinoheterociclos como moduladores de indolamina-2,3-dioxigenasaInfo
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- AR062881A1 AR062881A1 ARP070104118A ARP070104118A AR062881A1 AR 062881 A1 AR062881 A1 AR 062881A1 AR P070104118 A ARP070104118 A AR P070104118A AR P070104118 A ARP070104118 A AR P070104118A AR 062881 A1 AR062881 A1 AR 062881A1
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Abstract
Composiciones y métodos farmacéuticos. Moduladores de indolamina-2,3-dioxigenasa (IDO), para tratar cáncer, infecciones virales, depresion, trastorno neurodegenerativo, trauma, cataratas, rechazo de trasplantes, enfermedad autoinmune. Reivindicacion 1: Un compuesto de la formula 1: o una de sus sales farmacéuticamente aceptables, caracterizado porque: W es O, S o NR1; U es N o CR3: X es N o CR4; Q es H, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, arilo, heteroarilo, cicloalquilo o heterocicloalquilo, en donde dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6, arilo, heteroarilo, cicloalquilo o heterocicloalquilo está opcionalmente sustituido con 1, 2, 3, 4 o 5 sustituyentes seleccionados, de modo independiente, de halo, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, hidroxialquilo C1-6, cianoalquilo C1-6, pentahalosulfanilo, Cy4, -alquil C1-4-Cy4, CN, NO2, ORa4, -alquil C1-4-ORa4, SRa4, -alquil C1-4-SRa4, C(O)Rb4, -alquil C1- 4-C(O)Rb4, C(O)NRc4Rd4, -alquil C1-4-C(O)NRc4Rd4, C(O)ORa4, -alquil C1-4-C(O)ORa4, OC(O)Rb4, -alquil C1-4-OC(O)Rb4, OC(O)NRc4Rd4, -alquil C1-4-OC(O)NRc4Rd4, NRc4Rd4, NRc4C(O)Rb4, -alquil C1-4-NRc4CORb4, NRc4C(O)NRc4Rd4 -alquil C1-4-NRc4C(O)NRc4Rd4, NRc4C(O)ORa4, -alquil C1-4-NRc4C(O)ORa4, C(=NRi4)NRc4Rd4, NRc4C(=NRi4)NRc4Rd4, P(Rf4)2, P(ORe4)2, P(O)Re4Rf4, P(O)ORe4ORf4, S(O)Rb4, -(alquil C1-4-S(O)Rb4, S(O)NRc4Rd4, -alquil C1-4-S(O)NRc4Rd4, S(O)2Rb4, -alquil C1-4-S(O)2Rb4, NRc4S(O)2Rb4, -alquil C1-4-NRc4S(O)2Rb4, S(O)2NRc4Rd4 y -alquil C1-4-S(O)2NRc4Rd4; R1 es H, alquilo C1-10, alquenilo C2-6 o alquinilo C2-6; R2 es halo, alquilo C1-10, alquenilo C2-10, alquinilo C2-10, haloalquilo C1-6, hidroxialquilo C1-6, cianoalquilo C1-6, pentahalosulfanilo, Cy3, CN, NO2, ORa3, SRa3, C(O)Rb3, C(O)NRc3Rd3, C(O)ORa3, OC(O)Rb3, OC(O)NRc3Rd3, NRc3Rd3, NRc3C(O)Rb3, NRc3C(O)NRc3Rd3, NRc3C(O)ORa3, C(=NRi3)NRc3Rd3, NRc3C(=NRi3)NRc3Rd3, P(Rf3)2, P(ORe3)2, P(O)Re3Rf3, P(O)ORe3ORf3, S(O)Rb3, S(O)NRc3Rd3, S(O)2Rb3, NRc3S(O)2Rb3 o S(O)2NRc3Rd3 en donde dicho alquilo C1-10, alquenilo C2-10, o alquinilo C2-10, está opcionalmente sustituido con 1, 2, 3, 4 o 5 sustituyentes seleccionados, de modo independiente, de halo, alquilo C1-10, alquenilo C2-10, alquinilo C2-10, haloalquilo C1-10, hidroxialquilo C1-10, cianoalquilo C1-10, pentahalosulfanilo, Cy3, CN, NO2, ORa3, SRa3, C(O)Rb3, C(O)NRc3Rd3, C(O)ORa3, OC(O)Rb3, OC(O)NRc3Rd3, NRc3Rd3, NRc3C(O)Rb3, NRc3C(O)NRc3Rd3, NRc3C(O)ORa3, C(=NRi3)NRc3Rd3, NRc3C(=NRi3)NRc3Rd3, P(Rf3)2, P(ORe3)2, P(O)Re3Rf3, P(O)ORe3ORf3, S(O)Rb3, S(O)NRc3Rd3, S(O)2Rb3, NRc3S(O)2Rb3 y S(O)2NRc3Rd3; R3 y R4 están seleccionados, de modo independiente, de H, halo, alquilo C1-4, alquenilo C2-6 y alquinilo C2-6; R5 es H, C(O)R6, C(O)OR7 o C(O)NR8NR9; R6 y R7 están seleccionados, de modo independiente, de H, alquilo C1-8, arilo, heteroarilo, cicloalquilo, heterocicloalquilo, arilalquilo, heteroarilalquilo, cicloalquilalquilo y heterocicloalquilalquilo, cada uno opcionalmente sustituido con 1, 2, 3 sustituyentes seleccionados, de modo independiente, de halo, CN, NO2, OH, alcoxi C1-4, haloalcoxi C1-4, amino, alquil C1-4-amino, dialquil C2-8-amino, alquilo C1-6, alquenilo C2-6 y alquinilo C2-6; R8 y R9 están seleccionados, de modo independiente, de H, alquilo C1-8, arilo, heteroarilo, cicloalquilo, heterocicloalquilo, arilalquilo, heteroarilalquilo, cicloalquilalquilo y heterocicloalquilalquilo, cada uno opcionalmente sustituido con 1, 2 o 3 sustituyentes seleccionados, de modo independiente, de halo, CN, NO2, OH, alcoxi C1-4, haloalcoxi C1-4, amino, alquil C1-4-amino, dialquil C2-8-amino, alquilo C1-6, alquenilo C2-6 y alquinilo C2-6; o R1 y R3 junto con los átomos a los que están unidos forman un heteroarilo o un anillo heterocicloalquilo de 4-20 miembros, en donde dicho heteroarilo o anillo heterocicloalquilo de 4-20 miembros está opcionalmente sustituido con 1, 2, 3, 4 o 5 sustituyentes seleccionados, de modo independiente, de halo, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, hidroxialquilo C1-6, cianoalquilo C1-6, Cy, CN, NO2, ORa, SRa, C(O)Rb, C(O)NRcRd, C(O)ORa, OC(O)Rb, OC(O)NRcRd, NRcRd, NRcC(O)Rb, NRcC(O)NRcRd, NRcC(O)ORa, C(=NRi)NRcRd, NRcC(=NRi)NRcRd, P(Rf)2, P(ORe)2, P(O)ReRf, P(O)OReORf, S(O)Rb, S(O)NRcRd, S(O)2Rb, NRcS(O)2Rb y S(O)2NRcRd, en donde dicho alquilo C1-6, alquenilo C2-6, o alquinilo C2-6, está sustituido con 1, 2, o 3 sustituyentes seleccionados, de modo independiente, de Cy, CN, NO2, ORa, SRa, C(O)Rb, C(O)NRcRd, C(O)ORa, OC(O)Rb, OC(O)NRcRd, NRcRd, NRcC(O)Rb, NRcC(O)NRcRd, NRcC(O)ORa, C(=NRi)NRcRd, NRcC(=NRi)NRcRd, P(Rf)2, P(ORe)2, P(O)ReRf, P(O)OReORf, S(O)Rb, S(O)NRcRd, S(O)2Rb, NRcS(O)2Rb y S(O)2NRcRd; o R2 y R3 junto con los átomos a los que están unidos forman un arilo, cicloalquilo, heteroarilo o anillo heterocicloalquilo de 4-20 miembros, en donde dicho arilo, cicloalquilo, heteroarilo o anillo heterocicloalquilo de 4-20 miembros está opcionalmente sustituido con 1, 2, 3, 4 o 5 sustituyentes seleccionados, de modo independiente, de halo, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, hidroxialquilo C1-6, cianoalquilo C1-6, Cy1, CN, NO2, ORa1, SRa1, C(O)Rb1, C(O)NRc1Rd1, C(O)ORa1, OC(O)Rb1, OC(O)NRc1Rd1, NRc1Rd1, NRc1C(O)Rb1, NRc1C(O)NRc1Rd1, NRc1C(O)ORa1, C(=NRi1)NRc1Rd1, NRc1C(=NRi1)NRc1Rd1, P(Rf1)2, P(ORe1)2, P(O)Re1Rf1, P(O)ORe1ORf1, S(O)Rb1, S(O)NRc1Rd1, S(O)2Rb1, NRc1S(O)2Rb1 y S(O)2NRc1Rd1, en donde dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6, está opcionalmente sustituido con 1, 2, o 3 sustituyentes seleccionados, de modo independiente, Cy1, CN, NO2, ORa1, SRa1, C(O)Rb1, C(O)NRc1Rd1, C(O)ORa1, OC(O)Rb1, OC(O)NRc1Rd1, NRc1Rd1, NRc1C(O)Rb1, NRc1C(O)NRc1Rd1, NRc1C(O)ORa1, C(=NRi1)NRc1Rd1, NRc1C(=NRi1)NRc1Rd1, P(Rf1)2, P(ORe1)2, P(O)Re1Rf1, P(O)ORe1ORf1, S(O)Rb1, S(O)NRc1Rd1, S(O)2Rb1, NRc1S(O)2Rb1 y S(O)2NRc1Rd1, o R2 y R4 junto con los átomos a los que están unidos forman un arilo, cicloalquilo, heteroarilo o anillo heterocicloalquilo de 4-20 miembros, en donde dicho arilo, cicloalquilo, heteroarilo o anillo heterocicloalquilo de 4-20 miembros está opcionalmente sustituido con 1, 2, 3, 4 o 5 sustituyentes seleccionados, de modo independiente, de halo, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, hidroxialquilo C1-6, cianoalquilo C1-6, Cy2, CN, NO2, ORa2, SRa2, C(O)Rb2, C(O)NRc2Rd2, C(O)ORa2, OC(O)Rb2, OC(O)NRc2Rd2, NRc2Rd2, NRc2C(O)Rb2, NRc2C(O)NRc2Rd2, NRc2C(O)ORa2, C(=NRi2)NRc2Rd2, NRc2C(=NRi2)NRc2Rd2, P(Rf2)2, P(ORe2)2, P(O)Re2Rf2, P(O)ORe2ORf2, S(O)Rb2, S(O)NRc2Rd2, S(O)2Rb2, NRc2S(O)2Rb2 y S(O)2NRc2Rd2, en donde dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6, está opcionalmente sustituido con 1, 2, o 3 sustituyentes seleccionados, de modo independiente, Cy2, CN, NO2, ORa2, SRa2, C(O)Rb2, C(O)NRc2Rd2, C(O)ORa2, OC(O)Rb2, OC(O)NRc2Rd2, NRc2Rd2, NRc2C(O)Rb2, NRc2C(O)NRc2Rd2, NRc2C(O)ORa2, C(=NRi2)NRc2Rd2, NRc2C(=NRi2)NRc2Rd2, P(Rf2)2, P(ORe2)2, P(O)Re2Rf2, P(O)ORe2ORf2, S(O)Rb2, S(O)NRc2Rd2, S(O)2Rb2, NRc2S(O)2Rb2 y S(O)2NRc2Rd2, Ra3 y Ra4 están seleccionados, de modo independiente, de H, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, alquinilo C2- 6, Cy5 y Cy-alquilo C1-6-, en donde dicho alquilo C1-6, alquenilo C2-6 o alquinilo C2-6 está opcionalmente sustituido con 1, 2, 3, 4 o 5 sustituyentes seleccionados, de modo independiente, de halo, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, hidroxialquilo C1-6, cianoalquilo C1-6, Cy5, CN, NO2, ORa5 SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(=NRi5)NRc5Rd5, NRc5C(=NRi5)NRc5Rd5, P(Rf5)2, P(ORe5)2, P(O)Re5Rf5, P(O)ORe5ORf5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, NRc5S(O)2Rb5 y S(O)2NRc5Rd5, Rb3 y Rb4 están seleccionados, de modo independiente de H, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, alquinilo C2-6, Cy5 y Cy5-alquilo C1-6-, en donde dicho alquilo C1-6, alquenilo C2-6 o alquinilo C2-6 está opcionalmente sustituido con 1, 2, 3, 4 o 5 sustituyentes seleccionados, de modo independiente, de halo, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, hidroxialquilo C1-6, cianoalquilo C1-6, Cy5, CN, NO2, ORa5, SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(=NRi5)NRc5Rd5, NRc5C(=NRi5)NRc5Rd5, P(Rf5)2, P(ORe5)2, P(O)Re5Rf5, P(O)ORe5ORf5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, NRc5S(O)2Rb5 y S(O)2NRc5Rd5, Rc3 y Rc4 están seleccionados, de modo independiente, de H, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, alquinilo C2-6, C(O)Rb5, C(O)NRc5Rd5, C(=NRi5)NRc5Rd5, Cy5 y Cy5-alquilo C1-6-, en donde dicho alquilo C1-6, alquenilo C2-6 o alquinilo C2-6 está opcionalmente sustituido con 1, 2, 3, 4 o 5 sustituyentes seleccionados, de modo independiente, de halo, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, hidroxialquilo C1-6, cianoalquilo C1-6, Cy5, CN, NO2, ORa5, SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(=NRi5)NRc5Rd5, NRc5C(=NRi5)NRc5Rd5, P(Rf5)2, P(ORe5)2, P(O)Re5Rf5, P(O)ORe5ORf5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, NRc5S(O)2Rb5 y S(O)2NRc5Rd5, Rd3 y Rd4 están seleccionados, de modo independiente, de H, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, alquinilo C2-6, C(O)Rb5, C(O)NRc5Rd5, C(=NRi5)NRc5Rd5, Cy5 y Cy5-alquilo C1-6-, en donde dicho alquilo C1-6, alquenilo C2-6 o alquinilo C2-6 está opcionalmente sustituido con 1, 2, 3, 4 o 5 sustituyentes seleccionados, de modo independiente, de halo, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, hidroxialquilo C1-6, cianoalquilo C1-6, Cy5, CN, NO2, ORa5, SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(=NRi5)NRc5Rd5, NRc5C(=NRi5)NRc5Rd5, P(Rf5)2, P(ORe5)2, P(O)Re5Rf5, P(O)ORe5ORf5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, NRc5S(O)2Rb5 y S(O)2NRc5Rd5, o Rc3 y Rd3 junto con el átomo de N al que están unidos forman un grupo heteroarilo o heterocicloalquilo de 4, 5, 6 o
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TW200819445A (en) | 2008-05-01 |
US8507541B2 (en) | 2013-08-13 |
WO2008036653A3 (en) | 2008-07-31 |
JP2010504347A (ja) | 2010-02-12 |
ES2704641T3 (es) | 2019-03-19 |
US20080214546A1 (en) | 2008-09-04 |
WO2008036653A2 (en) | 2008-03-27 |
CL2007002650A1 (es) | 2008-02-08 |
EP2064194A2 (en) | 2009-06-03 |
JP5432715B2 (ja) | 2014-03-05 |
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