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AR040407A1 - Compuestos heterociclicos inhibidores de la funcion del canal de potasio - Google Patents

Compuestos heterociclicos inhibidores de la funcion del canal de potasio

Info

Publication number
AR040407A1
AR040407A1 AR20030101347A ARP030101347A AR040407A1 AR 040407 A1 AR040407 A1 AR 040407A1 AR 20030101347 A AR20030101347 A AR 20030101347A AR P030101347 A ARP030101347 A AR P030101347A AR 040407 A1 AR040407 A1 AR 040407A1
Authority
AR
Argentina
Prior art keywords
alkyl
independently
aryl
groups
heteroaryl
Prior art date
Application number
AR20030101347A
Other languages
English (en)
Inventor
Adam Lloyd
Yoon T Jeon
Heather Finlay
Lin Yan
Serge Beaudoin
Michael F Gross
Original Assignee
Bristol Myers Squibb Co
Icagen Inc
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 Bristol Myers Squibb Co, Icagen Inc filed Critical Bristol Myers Squibb Co
Publication of AR040407A1 publication Critical patent/AR040407A1/es

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Abstract

Inhibidores de la función del canal de potasio (especialmente inhibidores de la subfamilia Kv1 de los canales de K+ que se abren con voltaje, especialmente los inhibidores Kv1.5 que se han ligado a la corriente Ikur- del rectificador K+ retrasada de activación ultrarrápida), métodos de uso de tales compuestos en la prevención y tratamiento de la arritmia y condiciones asociadas con Ikur-, y a composiciones farmacéuticas que contienen tales compuestos. Reivindicación 1: Un compuesto de la fórmula (1) enantiómeros, diastereómeros, sales y solvatos de los mismos donde m y p son independientemente 0, 1, 2 o 3 con la condición de que la suma de m y p es de al menos 2; Q es NR1, O, S, S(O) o S(O)2; R1 es un radical del grupo de fórmulas (2), -C(=NR8b)R8c, -SO2R8c, -OC(O)CCl3, -C(=S)R8c, arilo opcionalmente substituido, heteroarilo opcionalmente substituido, heterociclo opcionalmente substituido, perfluoroalquilo, ciano, hidroxi, alcoxi opcionalmente substituido, ariloxi opcionalmente substituido, heteroariloxi opcionalmente substituido, alquilo opcionalmente substituido, cicloalquilo opcionalmente substituido, alquenilo opcionalmente substituido, o alquinilo opcionalmente substituido; R2 es heteroarilo, (heteroaril)alquilo, arilo, (aril)alquilo, heterociclo, (heterociclo)alquilo, alquilo o cicloalquilo, cualquiera de los cuales puede estar opcionalmente substituido independientemente con uno o más grupos T1, T2 o T3; J es un enlace, alquileno C1-4 opcionalmente substituido independientemente con uno o más grupos T1a,T2a o T3a, o alquenileno C1-4 opcionalmente substituido independientemente con uno o más grupos T1a, T2a o T3a ; R3 es un radical del grupo de fórmulas (3); R4 es H, alquilo, haloalquilo, alquenilo, alquinilo, cicloalquilo, heterociclo, arilo, (aril)alquilo o heteroarilo cualquiera de los cuales puede estar opcionalmente substituido independientemente con uno o más grupos T1b, T2b o T3b ; R5 es (a) -NR6aR7a, ciano o (b) heteroarilo, (heteroaril)alquilo, arilo, (aril)alquilo, alquilo, cicloalquilo, (cicloalquil)alquilo, heterociclo, (heterociclo)alquilo, o alquilo cualquiera de los cuales puede estar opcionalmente substituido independientemente con uno o más grupos T1c, T2c o T3c; R6, R6a, R7, R7a, R8, R8a, R8a1, R8a2, y R8a3 son independientemente H, alquilo, hidroxi, alcoxi, ariloxi, heterociclooxi, heteroariloxi, (hidroxi)alquilo, (alcoxi)alquilo, (ariloxi)alquilo, (heterociclooxi)alquilo, (heteroariloxi)alquilo, (ciano)alquilo, (alquenil)alquilo, (alquinil)alquilo, cicloalquilo, (cicloalquil)alquilo, arilo, (aril)alquilo, heteroarilo, (heteroaril)alquilo, heterociclo, (heterociclo)alquilo, -C(O)R9, -CO2R9, -C(O)-NR9R10, o -NR9R10 cualquiera de los cuales puede estar opcionalmente substituido independientemente con uno o más grupos T1d, T2d o T3d; o R6 y R7, o R6a y R7a junto con el átomo de nitrógeno al cual se enlazan, pueden combinarse para formar un anillo heterociclo de 4 hasta 8 miembros opcionalmente substituido independientemente con uno o más grupos T1d, T2d o T3d; o uno de R6 o R7, puede combinarse con uno de R8, R8a o R9 pueden combinarse para formar un anillo de 5 hasta 8 miembros saturado o no saturado opcionalmente substituido independientemente con uno o más grupos T1d, T2d o T3d; o uno de R6a o R7a, pueden combinarse con R8a1 para formar un anillo de 5 hasta 8 miembros saturado o no saturado opcionalmente substituido independientemente con uno o más grupos T1d, T2d o T3d; R8b es independientemente H, alquilo, arilo, ciano, nitro, acilo o -SO2(alquilo) donde los grupos alquilo y arilo pueden estar opcionalmente substituido independientemente con uno o más grupos T1d, T2d o T3d; R8c es H, alquilo, cicloalquilo, alquenilo, alquinilo, arilo, arilalquilo, heterociclo, heteroarilo, alcoxi o ariloxi cualquiera de los cuales puede estar opcionalmente substituido independientemente con uno o más grupos T1d, T2d o T3d; R8d es R4, COR4, CO2R4, SO2R4, CONR6R7, o SO2NR6R7; R9 y R10 son independientemente H, alquilo, hidroxi, alcoxi, ariloxi, heterociclooxi, heteroariloxi, (hidroxi) alquilo, (alcoxi)alquilo, (ariloxi)alquilo, (heterocilooxi)alquilo, (heteroariloxi)alquilo, cicloalquilo, (cicloalquil)alquilo, arilo, (aril)alquilo, heteroarilo, (heteroaril)alquilo, heterociclo, o (heterociclo)alquilo cualquiera de los cuales puede estar opcionalmente substituido independientemente con uno o más grupos T1f, T2f o T3f o R9 y R10 juntos con el átomo de nitrógeno al cual se enlazan pueden combinarse para formar un anillo saturado o no saturado que puede estar opcionalmente substituido independientemente con uno o más grupos T1f, T2f o T3f; W es =NR8a1, =N-CO2R8a1, =N-COR8a1, =N-CN, =N-SO2R8a1, o =CHNO2; X1 es O, S, NR8a2 o CH2; Z, Z1 y Z2 son independientemente =O, =S, =NR8a3 o =N-CN; Rx es uno o más substituyentes opcionales, enlazados a cualquier átomo de carbono en el anillo disponible, independientemente seleccionado de T1g, T2g o T3g; T1-1g, T2-2g, y T3-3g son cada uno independientemente (1) hidrogeno o T6, donde T6 es (i) alquilo, (hidroxi)alquilo, (alcoxi)alquilo, alquenilo, alquinilo, cicloalquilo, (cicloalquil)alquilo, cicloalquenilo, (cicloalquenil)alquilo, arilo, (aril)alquilo, heterociclo, (heterociclo)alquilo, heteroarilo, o (heteroaril)alquilo; (ii) un grupo (i) que por si mismo está substituido por uno o más de los mismos o diferentes grupos (i); o (iii) un grupo (i) o (ii) que está independientemente substituido por uno o más (preferiblemente 1 a 3) de los siguientes grupos (2) hasta (13) de la definición de T1-1g, T2-2g y T3-3g, (2) -OH o -OT6, (3) -SH o -ST6, (4) -C(O)tH, -C(O)tT6, o -O-C(O)T, en donde t es 1 o 2; (5) -SO3H, -S(O)tT6, o S(O)tN(T9)T6, (6) halo, (7) ciano, (8) nitro, (9) -T4-NT7T8, (10) -T4-N(T9)-T5-NT7T8, (11) -T4-N(T10)-T5-T6, (12) -T4-N(T10)-T5-H, (13) oxo; T4 y T5 son cada uno independientemente (1) un enlace sencillo, (2) -T11S(O)t-T12 (3) -T11-C(O)-T12-, (4) -T11-C(S)-T12, (5) -T11-O-T12, (6) -T11-S-T12-, (7) -T11-O-C(O)-T12-, (8) -T11-C (O)-O-T12-, (9) -T11-C(=NT9a)-T12-, o (10) -T11-C(O)-C (O)-T12-; T7, T8, T9, T9a y T10 (1) son cada uno independientemente hidrogeno o un grupo proporcionado en la definición de T6, o (2) T7 y T8 pueden juntos ser alquileno o alquenileno, completando un anillo saturado o no saturado de 3 hasta 8 miembros juntos con los átomos a los cuales se enlazan, cuyo anillo está substituido o no substituido con uno o más grupos enlistados en la descripción de T1-1g, T2-2g y T3-3g; o (3) T7 o T8, junto con T9, puede ser alquileno o alquenileno completando un anillo saturado o no saturado de 3 hasta 8 miembros juntos con los átomos de nitrógeno a los cuales se enlazan, cuyo anillo está substituido o no substituido con uno o más grupos enlistados en la descripción de T1-1g, T2-2g y T3-3g; o (4) T7 y T8 o T9 y T10 junto con el átomo de nitrógeno al cual se enlazan, pueden combinarse para formar un grupo -N=CT13T14 donde T13 y T14 son cada uno independientemente H o un grupo proporcionado en la definición de T6; y T11 y T12 son cada uno independientemente (1) un enlace sencillo, (2) alquileno, (3) alquenileno, o (4) alquinileno; con la condición de que el compuesto es diferente a (i) un compuesto de fórmula (4) en donde R1i es H, alquilo, aralquilo, -C(O)alquilo, -C(O)arilo, -C(O)aralquilo, -C(O)alquileno -CO2alquilo, -CO2alquilo, -CO2alquenilo, -CO2aralquilo, o - SO2alquilo ; y R8i es H, o alquilo; (ii) un compuesto de fórmula iia, iib o iic en donde es 0, 1 o 2; y R1iib es H o -C(O)2alquilo; (c) en donde R1iic es H o alquilo; y R8iic es H o alquilo; (iii) un compuesto de fórmula iii en donde R1iii es -alquiIeno-C(O)-Ar en donde Ar es fenilo, alquilfenilo, xililo, halofenilo, metoxifenilo o tienilo; y R2iii es tienilo, fenilo, halofenilo, metoxifenilo, alquilfenilo, xililo, o trifluorometilfenilo; (iv) un compuesto de fórmula iv en donde R1iv es (5) ,donde T1h es alquilo, arilo, heteroarilo, (aril)alquilo, (heteroaril)alquilo, (cicloalquil)alquilo, -alquileno-M-alquilo, -alquileno-M-alquileno-arilo, -alquileno-M-alquileno-heteroarilo, -alquileno-M-alquileno-cicloalquilo en donde los grupos alquilo y alquileno pueden estar opcionalmente substituidos con 1 hasta 5 halo, -S(O)qH, -S(O)qalquilo, o 1 a 3 hidroxi, alcoxi, carboxilo o -C(O)Oalquilo, y en donde los grupos arilo y heteroarilo pueden estar opcionalmente substituidos con fenilo, fenoxi, (aril)alcoxi, (heteroaril)alcoxi, halofenilo, 1 hasta 3 halo o alquilo,1 hasta 3 metoxi, alcoxi, o cicloalcoxi, 1 hasta 3 trifluorometilo o trifluorometoxi, 1 hasta 2 metilendioxi, S(O)qR5b, nitro, -NR5bR5b, -NR5bC(O)R5b, -C(O)OR5b, -C(O)NR5bR5b, -SO2NR5bR5b, -NR5bSO2arilo, -NR5bSO2heteroarilo, o -NR5bSO2R5b ; M es O, SOq, NR5bC(O), C(O)NR5b, OC(O), C(O)O, -CR5b=CR5b-, o -C:::C-; T2h es H, alquilo, o cicloalquilo; o T1h y T2h se combinan para formar un anillo de 3 hasta 8 miembros que incluye opcionalmente heteroátomos; T3h es -LC(O)ANR6dR7d; L es NR5c, O o CH2, R5c es H, alquilo o R5c combinado con T2h forman un anillo de 3 hasta 8 miembros; R6d y R7d son independientemente H, alquilo, o alquilo substituido en donde los substituyentes se seleccionan de fenilo, fenoxi, 2-furilo, -C(O)Oalquilo, -S(O)qalquilo, 1 a 5 halo, 1 a 3 hidroxi, 1 a 3 -OC(O)alquilo, o 1 a 3 alcoxi, o R6d y R7d pueden combinarse para formar un anillo no saturado que contiene opcionalmente heteroátomos adicionales; A es un enlace o (6) en donde r y s son independientemente 0-3; Q1 es un enlace, NR5b o O; R15 y R15a son independientemente H, alquilo, trifluorometilo, fenilo o alquilo opcionalmente substituido en donde los substituyentes se seleccionan de imidazolilo, fenilo, indolilo, p-hidroxifenilo, OR, S(O)qR5b, C(O)OR5b, cicloalquilo, NR5bR5b, C(O)NR5bR5b, o R15 y R15a pueden independientemente unirse a uno o ambos de R6d y R7d para formar puentes alquileno entre el nitrógeno terminal y la porción alquilo del grupo R15 y R15a, o R15 y R15a pueden combinarse para formar un anillo de 3 hasta 7 miembros; R2iv es alquilo, cicloalquilo, arilo
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