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AR056187A1 - Derivados de imidazo[1,2-a)piridina: preparacion, composiciones farmaceuticas y uso para preparar medicamentos - Google Patents

Derivados de imidazo[1,2-a)piridina: preparacion, composiciones farmaceuticas y uso para preparar medicamentos

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Publication number
AR056187A1
AR056187A1 ARP060101088A ARP060101088A AR056187A1 AR 056187 A1 AR056187 A1 AR 056187A1 AR P060101088 A ARP060101088 A AR P060101088A AR P060101088 A ARP060101088 A AR P060101088A AR 056187 A1 AR056187 A1 AR 056187A1
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AR
Argentina
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group
alkyl
alkenyl
optionally substituted
heterocycloalkyl
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ARP060101088A
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S Bio Pte Ltd
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract

Los compuestos de hidroximato son inhibidores de histona deacetilasa. Se divulgan compuestos de imidazo[1,2-a]piridina y métodos para su preparacion. Estos compuestos pueden ser utiles como medicamentos para el tratamiento de trastornos proliferativos así como enfermedades relacionadas o asociadas con enzimas que tienen actividad de histona deacetilasa (HDAC). Reivindicacion 1: Un compuesto caracterizado porque tiene la formula (1), en donde R1 está seleccionado del grupo que consiste en H, halogeno, -CN, -NO2, -CF3, -OCF3, alquilo, alquenilo, alquinilo, haloalquilo, haloalquenilo, heteroalquilo, cicloalquilo, cicloalquenilo, heterocicloalquilo, heterocicloalquenilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo, arilalquenilo, cicloalquilheteroalquilo, arilheteroalquilo, heterocicloalquilheteroalquilo, heteroarilheteroalquilo, hidroxi, hidroxialquilo, alcoxi, alcoxialquilo, alcoxiarilo, alqueniloxi, alquiniloxi, cicloalquiloxi, heterocicloalquiloxi, ariloxi, heteroariloxi, arilalquiloxi, fenoxi, benciloxi, amino, alquilamino, aminoalquilo, acilamino, arilamino, sulfonilamino, sulfinilamino, -COOH, - COR5, -COOR5, -CONHR5, -NHCOR5, -NHCOOR5, - NHCONHR5, C(=NOH)R5, - alquilNCOR5, alcoxicarbonilo, alquilaminocarbonilo, sulfonilo, alquilsulfonilo, alquilsulfinilo, arilsulfonilo, arilsulfinilo, aminosulfonilo, SR6 y acilo, cada uno de los cuales puede estar opcionalmente substituido; o R1 = L; R2 está seleccionado del grupo que consiste en H, halogeno, -CN, -NO2, -CF3, -OCF3, alquilo, alquenilo, alquinilo, haloalquilo, haloalquenilo, heteroalquilo, cicloalquilo, cicloalquenilo, heterocicloalquilo, heterocicloalquenilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo, arilalquenilo, cicloalquilheteroalquilo, arilheteroalquilo, heterocicloalquilheteroalquilo, heteroarilheteroalquilo, hidroxi, hidroxialquilo, alcoxi, alcoxialquilo, alcoxiarilo, alqueniloxi, alquiniloxi, cicloalquiloxi, heterocicloalquiloxi, ariloxi, heteroariloxi, arilalquiloxi, fenoxi, benciloxi, amino, alquilamino, aminoalquilo, acilamino, arilamino, sulfonilamino, sulfinilamino, -COOH, - COR5, -COOR5, -CONHR5, -NHCOR5, -NHCOOR5, -NHCONHR5, C(=NOH)R5, - alquilNCOR5, alcoxicarbonilo, alquilaminocarbonilo, sulfonilo, alquilsulfonilo, alquilsulfinilo, arilsulfonilo, arilsulfinilo, aminosulfonilo, SR6 y acilo, cada uno de los cuales puede estar opcionalmente substituido; o R2 = L; R3 está seleccionado del grupo que consiste en H, alquilo, alquenilo, alquinilo, haloalquilo, heteroalquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo y acilo cada uno de los cuales puede estar opcionalmente substituido; R4 está seleccionado del grupo que consiste en H, alquilo, alquenilo, alquinilo, haloalquilo, heteroalquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo y acilo cada uno de los cuales puede estar opcionalmente substituido; cada Y está seleccionado de modo independiente del grupo que consiste en H, halogeno, -CN, -NO2, -CF3, -OCF3, alquilo, alquenilo, alquinilo, haloalquilo, haloalquenilo, haloalquinilo, heteroalquilo, cicloalquilo, cicloalquenilo, heterocicloalquilo, heterocicloalquenilo, arilo, heteroarilo, hidroxi, hidroxialquilo, alcoxi, alcoxialquilo, alcoxiarilo, alcoxiheteroarilo, alqueniloxi, alquiniloxi, cicloalquiloxi, cicloalqueniloxi, heterocicloalquiloxi, heterocicloalqueniloxi, ariloxi, heteroariloxi, arilalquilo, heteroarilalquilo, arilalquiloxi, amino, alquilamino, acilamino, aminoalquilo, arilamino, sulfonilo, alquilsulfonilo, arilsulfonilo, aminosulfonilo, aminoalquilo, alcoxialquilo, -COOH -C(O)OR6, -COR6, -SH, - SR7, -OR7, acilo y -NR8R9 cada uno de los cuales puede estar opcionalmente substituido; cada R5 está seleccionado de modo independiente del grupo que consiste en H, alquilo, alquenilo, alquinilo, haloalquilo, heteroalquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo y acilo cada uno de los cuales puede estar opcionalmente substituido; cada R6 está seleccionado de modo independiente del grupo que consiste en H, alquilo, alquenilo, alquinilo, haloalquilo, heteroalquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo y acilo cada uno de los cuales puede estar opcionalmente substituido; cada R7 está seleccionado de modo independiente del grupo que consiste en H, alquilo, alquenilo, alquinilo, haloalquilo, heteroalquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo y acilo cada uno de los cuales puede estar opcionalmente substituido; cada R8 y R9 está seleccionado de modo independiente del grupo que consiste en H, alquilo, alquenilo, alquinilo, haloalquilo, heteroalquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo y acilo cada uno de los cuales puede estar opcionalmente substituido; p es un entero seleccionado del grupo que consiste en 0, 1, 2 y 3; L está seleccionado del grupo que consiste en a) Cy-L1-W-; b) Cy-L1-W-L2-; c) Cy-(CH2)k-W-; d) L1-W-L2-; e) Cy-L1-; f) R12-W1-L1-W-; y g) -(CR20R21)m-(CR22R23)n-(CR24R25)o-NR26R27; en donde Cy está seleccionado del grupo que consiste en alquilo C1-15, aminoalquilo, heteroalquilo, heterocicloalquilo, cicloalquilo, arilo, ariloxi y heteroarilo, cada uno de los cuales puede estar opcionalmente substituido; L1 está seleccionado del grupo que consiste en un enlace, alquilo C1-5 y alquenilo C2-5, cada uno de los cuales puede estar opcionalmente substituido; L2 está seleccionado del grupo que consiste en alquilo C1-5 y alquenilo C2-5, cada uno de los cuales puede estar opcionalmente substituido; k es 0, 1, 2, 3, 4 o 5; W está seleccionado del grupo que consiste en un enlace, - O-, -S-, -S(O)-, -S(O)2-, -N(R10)-, -C(O)N(R10)-, -SO2N(R10)-, -N(R10)C(O)-, -N(R10)SO2-, -N(R10)C(O)N(R11)-, -C(O)N(R10)C(O)N(R11)- y -N(R10)C(O)N(R11)C(O)-; W1 está seleccionado del grupo que consiste en un enlace, -O-, -S-, -S(O)-, -S(O)2-, - N(R10)-, -C(O)N(R10)-, -SO2N(R10)-, -N(R10)C(O)-, -N(R10)SO2-, -N(R10)C(O)N(R11)-, -C(O)N(R10)C(O)N(R11)- y -N(R10)C(O)N(R11)C(O)-; cada R20, R21, R22, R23, R24 y R25 está seleccionado de modo independiente del grupo que consiste en H, halogeno, - CN, -NO2, -CF3, -OCF3, alquilo, alquenilo, alquinilo, haloalquilo, haloalquenilo, haloalquinilo, heteroalquilo, cicloalquilo, cicloalquenilo, heterocicloalquilo, heterocicloalquenilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo, arilalquenilo, cicloalquilheteroalquilo, heterocicloalquilheteroalquilo, heteroarilheteroalquilo, arilheteroalquilo, hidroxi, hidroxialquilo, alcoxi, alcoxialquilo, alcoxiarilo, alcoxiheteroarilo, alqueniloxi, alquiniloxi, cicloalquiloxi, heterocicloalquiloxi, ariloxi, arilalquiloxi, fenoxi, benciloxi heteroariloxi, amino, alquilamino, acilamino, aminoalquilo, arilamino, alcoxicarbonilo, alquilaminocarbonilo, sulfonilo, alquilsulfonilo, aminosulfonilo, arilsulfonilo, arilsulfinilo -COOH, -C(O)OR5, - COR5, -SH, -SR6, -OR6 y acilo, cada uno de los cuales puede estar opcionalmente substituido; o R20 y R21 cuando se toman juntos pueden formar un grupo de la formula =O o =S, y/o R22 y R23 cuando se toman juntos pueden formar un grupo de la formula =O o =S, y/o R24 y R25 cuando se toman juntos pueden formar un grupo de la formula =O o =S; cada R26 y R27 está seleccionado de modo independiente del grupo que consiste en H, halogeno, alquilo, alquenilo, alquinilo, haloalquilo, haloalquenilo, heteroalquilo, cicloalquilo, cicloalquenilo, heterocicloalquilo, heterocicloalquenilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo, arilalquenilo, cicloalquilheteroalquilo, heterocicloalquilheteroalquilo, heteroarilheteroalquilo, arilheteroalquilo, hidroxi, hidroxialquilo, alcoxi, alcoxialquilo, alcoxiarilo, alqueniloxi, alquiniloxi, cicloalquiloxi, heterocicloalquiloxi, ariloxi, arilalquiloxi, heteroariloxi, amino, alquilamino, aminoalquilo, acilamino, arilamino, fenoxi, benciloxi, COOH, alcoxicarbonilo, alquilaminocarbonilo, sulfonilo, alquilsulfonilo, alquilsulfinilo, arilsulfonilo, arilsulfinilo, aminosulfonilo, SR5, acilo y G, cada uno de los cuales puede estar opcionalmente substituido o R26 y R27 cuando se toman junto con el átomo de nitrogeno al que están unidos, forman un grupo heterocicloalquilo o heteroarilo, cada uno de los cuales puede estar opcionalmente substituido; m, n y o son cada uno enteros que están seleccionados de modo independiente del grupo que consiste en 0, 1, 2, 3 y 4; G es un grupo de formula -L3W3, en donde L3 está seleccionado del grupo que consiste en alquilo C1-5 y alquenilo C2-5, cada uno de los cuales puede estar opcionalmente substituido; W3 está seleccionado del grupo que consiste en un enlace, -OR12, -SR12, -S(O)R12, -S(O)2R12, -N(R12)2, -C(O)N(R12)2, -SO2N(R12)2, -NR12C(O)-, -NR12SO2R12, - NR12C(O)N(R12)2, -C(O)NR12C(O)N(R12) y -N(R12)C(O)N(R12)C(O)R12; R10 y R11 son iguales o diferentes y están está seleccionados de modo independiente de H, alquilo C1-6, alquenilo C1-6, heteroalquilo C1-10, cicloalquilo C4-9, heterocicloalquilo C4-9, arilo, heteroarilo, arilalquilo, y heteroarilalquilo y acilo cada uno de los cuales puede estar opcionalmente substituido; R12 está seleccionado del grupo que consiste en H, halogeno, -CN, -NO2, -CF3, -OCF3, alquilo, alquenilo, alquinilo, haloalquilo, haloalquenilo, heteroalquilo, cicloalquilo, cicloalquenilo, heterocicloalquilo, heterocicloalquenilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo, arilalque
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