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AR046411A1 - Derivados de bencimidazol. aplicaciones farmaceuticas - Google Patents

Derivados de bencimidazol. aplicaciones farmaceuticas

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Publication number
AR046411A1
AR046411A1 ARP040103390A AR046411A1 AR 046411 A1 AR046411 A1 AR 046411A1 AR P040103390 A ARP040103390 A AR P040103390A AR 046411 A1 AR046411 A1 AR 046411A1
Authority
AR
Argentina
Prior art keywords
alkyl
group
aminoalkyl
heterocycloalkyl
heteroaryl
Prior art date
Application number
Other languages
English (en)
Original Assignee
S Bio Pte Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by S Bio Pte Ltd filed Critical S Bio Pte Ltd
Publication of AR046411A1 publication Critical patent/AR046411A1/es

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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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Abstract

Estos compuestos pueden ser útiles como medicamentos para el tratamiento de trastornos proliferativos, así como otras enfermedades que comprenden, están relacionadas o asociadas con una desregulación de la historia desacetilasa (HDAC). Reivindicación 1: Un compuesto de la fórmula (1), en donde: R1 se selecciona del grupo integrado por; H, 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, amino, alquilamino, aminoalquilo, acilamino, arilamino, fenoxi, benciloxi, COOH, alcoxicarbonilo, alquilaminocarbonilo, sulfonilo, alquilsulfonilo, alquilsulfinilo, arilsulfonilo, arilsulfinilo, aminosulfonilo, SR4 y acilo, cada uno de los cuales puede estar insustituido o sustituido con uno o varios sustituyentes seleccionados de modo independiente del grupo integrado por: halógeno, =O, =S, -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, arilsulfinilo, aminosulfonilo, aminoalquilo, alcoxialquilo, -COOH, -C(O)OR5, -COR5, -SH, -SR6, -OR6, y acilo; o R1 = L; R2 se selecciona del grupo integrado por; H, halógeno, 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, heteroariloxi, arilalquiloxi, amino, alquilamino, aminoalquilo, acilamino, arilamino, fenoxi, benciloxi, COOH, alcoxicarbonilo, alquilaminocarbonilo, sulfonilo, alquilsulfonilo, alquilsulfinilo, arilsulfonilo, arilsulfinilo, aminosulfonilo, SR4 y acilo, cada uno de los cuales puede estar insustituido o sustituido con uno o varios sustituyentes seleccionados de modo independiente del grupo integrado por: halógeno, =O, =S, - 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, -COR5, -C(O)OR5, -SH, -SR5, -OR6, y acilo; o R2 = L; R3 se selecciona del grupo integrado por H, alquilo C1-6 y acilo; o un ión metálico seleccionado de sodio, calcio, magnesio; X e Y son iguales o diferentes y están seleccionados de modo independiente del grupo integrado por: H, halógeno, -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)OR5, -COR5, -SH, -SR6, -OR6, acilo y -NR7R8; cada R4 se selecciona del grupo integrado por: H, alquilo, alquenilo, alquinilo, haloalquilo, heteroalquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo y acilo; cada R5 está seleccionado de modo independientemente del grupo integrado por: alquilo, alquenilo, alquinilo, haloalquilo, heteroalquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo y acilo; cada R6 está seleccionado de modo independiente del grupo integrado por: alquilo, alquenilo, alquinilo, haloalquilo, heteroalquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo y acilo; cada R7 y R8 están seleccionados cada uno de modo independiente del grupo integrado por: H, alquilo, alquenilo, alquinilo, haloalquilo, heteroalquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, cicloalquilalquilo, heterocicloalquilalquilo, arilalquilo, heteroarilalquilo y acilo; L se selecciona del grupo integrado por: a) L=Cy-L1-W-, en donde: Cy es alquilo C1-5, aminoalquilo, heterocicloalquilo, cicloalquilo, arilo, ariloxi o heteroarilo, cada uno de los cuales puede estar opcionalmente sustituido con uno o varios sustituyentes seleccionados de modo independiente del grupo integrado por: halógeno, =O, =S, -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, -COR5, -C(O)OR5, -SH, -SR6, -OR6, y acilo; L1 se selecciona del grupo integrado por alquilo C1-5, que puede estar opcionalmente sustituido con uno o varios sustituyentes seleccionados de modo independiente del grupo integrado por: halógeno, =O; =S; -CN; -NO2; alquilo, alcoxi, acilamino y alquilamino; W se selecciona del grupo integrado por un enlace simple, -O-, -S-, -S(O)-, -S(O)2-, -N(R9)-, -C(O)N(R9)-, -SO2N(R9)-, N(R9)C(O)-, N(R9)SO2- y -N(R9)-C(O)-N(R10)-; b) L=Cy-L1-W-L2, en donde: Cy es alquilo C1-5, aminoalquilo, heterocicloalquilo, cicloalquilo, arilo, ariloxi o heteroarilo, cada uno de los cuales puede estar opcionalmente sustituido con uno o varios sustituyentes seleccionados de modo independiente del grupo integrado por: halógeno, =O, =S, -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)OR5, -COR5, -SH, -SR5, -OR6, y acilo; L1 y L2 son iguales o diferentes, y son, de modo independiente, alquilo C1-5, que puede estar opcionalmente sustituido con uno o varios sustituyentes seleccionados de modo independiente del grupo integrado por: halógeno, =O, =S, -CN, -NO2, -CF3, -COF3, alquilo, alcoxi, acilamino y alquilamino; W se selecciona del grupo integrado por un enlace simple, -O-, -S-, -S(O)-, -S(O)2-, -N(R9)-, -C(O)N(R9)-, -SO2N(R9)-, N(R9)C(O)-, N(R9)SO2- y -N(R9)-C(O)-N(R10)-; c) L=Cy-L1-W-, en donde: en donde: Cy es alquilo C1-5, aminoalquilo, heterocicloalquilo, cicloalquilo, arilo, ariloxi o heteroarilo, cada uno de los cuales puede estar opcionalmente sustituido con uno o varios sustituyentes seleccionados de modo independiente del grupo integrado por: halógeno, =O, =S, -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)OR5, -COR5, -SH, -SR5, -OR6, y acilo; m es 0, 1, 2, 3, 4 ó 5; W se selecciona del grupo integrado por un enlace simple, -O-, -S-, -S(O)-, -S(O)2-, -N(R9)-, -C(O)N(R9)-, - SO2N(R9)-, N(R9)C(O)-, N(R9)SO2- y -N(R9)-C(O)-N(R10)-; d) L=L1-W-L2, donde L1 y L2 son iguales o diferentes, y está seleccionados, de modo independiente, de alquilo C1-5, que puede estar opcionalmente sustituido con uno o varios sustituyentes seleccionados de modo independiente del grupo integrado por: halógeno, =O, =S, -CN, -NO2, -CF3, -OCF3, alquilo, alcoxi, acilamino y alquilamino; W se selecciona del grupo integrado por un enlace simple, -O-, -S-, -S(O)-, -S(O)2-, -N(R9)-, -C(O)N(R9)- , -SO2N(R9)-,
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