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AR046789A1 - Inhibidores de fosfodiesterasa 4, que incluyen analogos de diarilamina n-sustituidos - Google Patents

Inhibidores de fosfodiesterasa 4, que incluyen analogos de diarilamina n-sustituidos

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Publication number
AR046789A1
AR046789A1 ARP040104598A ARP040104598A AR046789A1 AR 046789 A1 AR046789 A1 AR 046789A1 AR P040104598 A ARP040104598 A AR P040104598A AR P040104598 A ARP040104598 A AR P040104598A AR 046789 A1 AR046789 A1 AR 046789A1
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AR
Argentina
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alkyl
halogen
substituted
combinations
cyano
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ARP040104598A
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Memory Pharm Corp
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    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract

Se logra la inhibición de la PDE4 utilizando compuestos, por ejemplo, análogos de diarilamina N-sustituidos. Reivindicación 1: Un compuesto de fórmula (1), donde A, B y D son cada uno N o CR5 donde al menos uno de A, B y D es N; R1 es halógeno, alquilo C1-4, alquilo halogenado C1-4, OR6, COR6, CONR6, o NR6COR10; R2 es halógeno, alquilo C1-4, alquilo halogenado C1-4 (por ejemplo, CH2F; CHF2, CF3), OR7, COR6, CONR6, o NR6COR10; R3 es alquilo C1-8 que es de cadena lineal o ramificada y que es insustituido o sustituido una o más veces por halógeno, ciano, alcoxi C1-4, o combinaciones de los mismos, un grupo alquilo carbocíclico parcialmente insaturado donde la porción carbocíclica tiene entre 5 y 14 átomos de C y la porción alquilo que es de cadena lineal o ramificada tiene entre 1 y 5 átomos de C, y que está insustituida, sustituida en la porción carbocíclica una o más veces por halógeno, alquilo, alcoxi, nitro, ciano, oxo, o combinaciones de los mismos, y/o sustituida en la porción alquilo una o más veces por halógeno, alcoxi C1-4, ciano o combinaciones de los mismos, arilalquilo con entre 7 y 19 átomos de C, donde la porción arilo tiene entre 6 y 14 átomos de C y la porción alquilo, que es de cadena lineal o ramificada, tiene entre 1 y 5 átomos de C, donde el radical arilalquilo es insustituido o sustituido, en la porción arilo, una o más veces por halógeno, trifluorometilo, CF3O, nitro, amino, alquilo, alcoxi, amino, alquilamino, dialquilamino, o combinaciones de los mismos, y/o sustituido en la porción alquilo por halógeno, ciano, alquilo C1-4, o combinaciones de los mismos, donde en la porción alquilo uno o más grupos -CH2CH2- se reemplazan cada uno optativamente por -CH=CH- o -C/C-, y/o uno o más grupos -CH2- se reemplazan cada uno optativamente por -O- o -NH-, o grupo heteroarilalquilo, donde la porción heteroarilo puede ser parcial o totalmente saturada y tiene entre 5 y 10 átomos en el anillo en donde al menos 1 átomo del anillo es un N, N-O, O o S, la porción alquilo, que es de cadena lineal o ramificada, tiene entre 1 y 5 átomos de C, el grupo heteroarilalquilo es insustituido, sustituido una o más veces en la porción heteroarilo por halógeno, alquilo, alcoxi, ciano, trifluorometilo, CF3O, nitro, oxo, amino, alquilamino, dialquilamino, o combinaciones de los mismos, y/o sustituido en la porción alquilo una o más veces por halógeno, ciano, alquilo C1-4, o combinaciones de los mismos, R4 es cicloalquilo C3-10, que es insustituido o sustituido una o más veces por halógeno, hidroxi, oxo, ciano, alquilo C1-4, alcoxi C1-4, o combinaciones de los mismos, arilo C6-14 y que es insustituido o sustituido una o más veces por halógeno, alquilo, alquenilo, alquinilo, hidroxi, alcoxi, alcoxialcoxi, nitro, metilendioxi, etilendioxi, trifluorometilo, OCF3, amino, aminoalquilo, aminoalcoxi, dialquilamino, hidroxialquilo, ácido hidroxámico, pirrolilo, tetrazol-5-ilo, 2-(-heterociclo)tetrazol-5-ilo, hidroxialcoxi, carboxi, alcoxicarbonilo, ciano, acilo, alquiltio, alquilsulfinilo, alquilsulfonilo, fenoxi, trialquilsililoxi, R8-L-, o combinaciones de los mismos; heteroarilo C5-10 en el anillo en donde al menos 1 átomo del anillo es un heteroátomo, que es insustituido o sustituido una o más veces por halógeno, alquilo, hidroxi, alcoxi, alcoxialcoxi, nitro, metilendioxi, etilendioxi, trifluorometilo, amino, aminometilo, aminoalquilo, aminoalcoxi, dialquilamino, hidroxialquilo, ácido hidroxámico, tetrazol-5-ilo, hidroxialcoxi, carboxi, alcoxicarbonilo, ciano, acilo, alquiltio, alquilsulfinilo, alquilsulfonilo, fenoxi, trialquilsililoxi, R8-L-, o combinaciones de los mismos, un grupo heterocíclico, que es saturado o parcialmente saturado, con entre 5 y 10 átomos en el anillo en donde al menos 1 átomo del anillo es un átomo de N, O o S, que es insustituido o sustituido una o más veces por halógeno, alquilo, hidroxi, alcoxi, alcoxialcoxi, nitro, oxo, metilendioxi, etilendioxi, trifluorometilo, OCF3, amino, aminometilo, aminoalquilo, aminoalcoxi, dialquilamino, hidroxialquilo, ácido hidroxámico, tetrazol-5-ilo, hidroxialcoxi, carboxi, alcoxicarbonilo, ciano, acilo, alquiltio, alquilsulfinilo, alquilsulfonilo, fenilsulfonilo, fenoxi, cicloalquilo, arilo, heteroarilo o combinaciones de los mismos, un grupo alquilo heterocíclico, donde la porción heterocíclica es saturada, parcialmente saturada o insaturada, y tiene entre 5 y 10 átomos en el anillo en donde al menos 1 átomo del anillo es un átomo de N, O o S, y la porción alquilo es de cadena lineal o ramificada y tiene entre 1 y 5 átomos de C, el grupo alquilo heterocíclico es insustituido, sustituido una o más veces en la porción heterocíclica por halógeno, alquilo, hidroxi, alcoxi, alcoxialcoxi, nitro, oxo, metilendioxi, etilendioxi, trifluorometilo, OCF3, amino, aminometilo, aminoalquilo, aminoalcoxi, dialquilamino, hidroxialquilo, ácido hidroxámico, tetrazol-5-ilo, hidroxialcoxi, carboxi, alcoxicarbonilo, ciano, acilo, alquiltio, alquilsulfinilo, alquilsulfonilo, fenilsulfonilo, fenoxi, cicloalquilo, arilo, heteroarilo o combinaciones de los mismos, y/o sustituida en la porción alquilo una o más veces por halógeno, oxo, hidroxi, ciano, o combinaciones de los mismos, y donde en la porción alquilo uno o más grupos -CH2CH2- se reemplazan cada uno optativamente por -CH=CH- o -C/C-, y uno o más grupos -CH2- se reemplazan cada uno optativamente por -O- o -NH; R5 es H, halógeno, alquilo C1- 4, alcoxi C1-4, o alquilo halogenado C1-4, alcoxi C1-4 o aloxi halogenado C1-4 ; R6 es H o alquilo C1-4, que es de cadena lineal o ramificada y que es insustituido o sustituido una o más veces por halógeno; R7 es H o alquilo C1-12 que es de cadena lineal o ramificada y que es insustituido o sustituido una o más veces por halógeno, hidroxi, ciano, alcoxi C1-4, oxo o combinaciones de los mismos, y donde optativamente uno o más grupos -CH2CH2- se reemplaza en cada caso por -CH=CH- o -C/C-, cicloalquilo C3-10 que es insustituido o sustituido una o más veces por halógeno, hidroxi, oxo, ciano, alquilo C1-4, alcoxi C1-4, o combinaciones de los mismos, cicloalquilalquilo C4-16 que es insustituido o sustituido en la porción cicloalquilo y/o la porción alquilo una o más veces por halógeno, oxo, ciano, hidroxi, alquilo C1-4, alcoxi C1-4 o combinaciones de los mismos; arilo C6-14 y que es insustituido o sustituido una o más veces por halógeno, CF3, OCF3, alquilo, hidroxi, alcoxi, nitro, metilendioxi, etilendioxi, ciano, o combinaciones de los mismos(por ejemplo metilfenilo, metoxifenilo, clorofenilo, etc); arilalquilo en donde la porción arilo tiene entre 6 y 14 átomos de C y la porción alquilo, que es de cadena lineal o ramificada, tiene entre 1 y 5 átomos de C, donde el radical arilalquilo es insustituido, sustituido, en la porción arilo una o más veces por halógeno, CF3, OCF3, alquilo, hidroxi, alcoxi, nitro, ciano, metilendioxi, etilendioxi, o combinaciones de los mismos, y/o sustituida en la porción alquilo una o más veces por halógeno, oxo, hidroxi, ciano, o combinaciones de los mismos, y donde en la porción alquilo uno o más grupos -CH2CH2- se reemplazan cada uno optativamente por -CH=CH- o -C/C-, y uno o más grupos -CH2-se reemplazan cada uno optativamente por -O- o -NH- , un grupo carbocíclico parcialmente insaturado con entre 5 y 14 átomos de C, que es insustituido o sustituido una o más veces por halógeno, alquilo, alcoxi, hidroxi, nitro, ciano, oxo, o combinaciones de los mismos, un grupo heterocíclico, que es saturado, parcialmente saturado o insaturado, con entre 5 y 10 átomos en el anillo en donde al menos 1 átomo del anillo es un átomo de N, O o S, que es insustituido o sustituido una o más veces por halógeno, hidroxi, arilo, alquilo, alcoxi, ciano, trifluorometilo, nitro, oxo, o combinaciones de los mismos, o un grupo alquilo heterocíclico, donde la porción heterocíclica es saturada, parcialmente saturada o insaturada, y tiene entre 5 y 10 átomos en el anillo en donde al menos 1 átomo del anillo es un átomo de N, O o S, y la porción alquilo es de cadena lineal o ramificada y tiene entre 1 y 5 átomos de C, el grupo alquilo heterocíclico es insustituido, sustituido una o más veces en la porción heterocíclica por halógeno, OCF3, hidroxi, arilo, alquilo, alcoxi, ciano, trifluorometilo, nitro, oxo, o combinaciones de los mismos, y/o sustituida en la porción alquilo una o más veces por halógeno, oxo, hidroxi, ciano, o combinaciones de los mismos, y donde en la porción alquilo uno o más grupos -CH2CH2- se reemplazan cada uno optativamente por -CH=CH- o -C/C-, y uno o más grupos -CH2- se reemplazan cada uno optativamente por -O- o -NH-; R8 es H, alquilo C1-8 que es insustituido o sustituido una o más veces por halógeno, alquilo C1-4, alcoxi C1-4, oxo, o combinaciones de los mismos, alquilamino o dialquilamino donde cada porción alquilo tiene en forma independiente entre 1 y 8; un grupo alquilo carbocíclico parcialmente insaturado donde la porción carbocíclica tiene entre 5 y 14 átomos de C y la porción alquilo tiene entre 1 y 5 átomos de C, y que es insustituido o sustituido una o más veces por halógeno, alquilo, alcoxi, nitro, ciano, oxo, o combinaciones de los mismos, cicloalquilo C3-10 que es insustituido o sustituido una o más veces por halógeno, hidroxi, oxo, ciano, alcoxi, alquilo C1-4, o combinaciones de los mismos, cicloalquilalquilo C4-16 que es insustituido o sustituido en la porción cicloalquilo y/o la porción alquilo una o más veces por halógeno, oxo, ciano, hidroxi, alquilo, alcoxi o combinaciones de los mismos, arilo C6-14 que es insustituido o sustituido una o más veces por halógeno, alquilo, hidroxi, alcoxi, alcoxialcoxi, nitro, metilendioxi, etilendioxi, trifluorometilo, amino, aminometilo, aminoalquilo, aminoalcoxi, dialquilamino, hidroxialquilo, ácido hidroxámico, tetrazol-5-ilo, hidroxialcoxi, carboxi, alcoxicarbonilo, ciano, acilo, alquiltio, alquilsulfinilo, alquilsulfonilo, fenoxi, cicloalquilo, arilo, heteroarilo o combinaciones de los mismos; arilalquilo C7-19, donde la porci
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