AR035624A1 - Compuesto derivado de sulfonilo y su uso en la fabricacion de medicamentos para inhibir la actividad de metaloproteinasas de matriz - Google Patents

Compuesto derivado de sulfonilo y su uso en la fabricacion de medicamentos para inhibir la actividad de metaloproteinasas de matriz

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Publication number
AR035624A1
AR035624A1 ARP000102311A ARP000102311A AR035624A1 AR 035624 A1 AR035624 A1 AR 035624A1 AR P000102311 A ARP000102311 A AR P000102311A AR P000102311 A ARP000102311 A AR P000102311A AR 035624 A1 AR035624 A1 AR 035624A1
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AR
Argentina
Prior art keywords
group
alkyl
aryl
hydride
amino
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ARP000102311A
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English (en)
Inventor
Joseph J Mcdonald
Thomas E Barta
Robert Becker
Shashidhar RAO
John N Freskos
Brent Mischke
Daniel P Getman
Gary A Decrescenzo
Clara Villamil
Luis Bedell
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Searle & Co
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Publication date
Application filed by Searle & Co filed Critical Searle & Co
Publication of AR035624A1 publication Critical patent/AR035624A1/es

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Abstract

Un compuesto derivado de sulfonilo que corresponde a la fórmula (1), o una sal aceptable para uso farmacéutico del mismo: donde y y z son cada uno 0 o 1 y la suma de z + y es 0 o 1; la estructura del anillo W es un anillo aromático o heteroaromático de 5 o 6 miembros; X es -CH2- o -NR9-, donde R9 se selecciona del grupo formado por un sustituyente hidruro, arilo, alquilo o arilalquilo; R1 es (i) un sustituyente que contiene un radical ciclohidrocarbilo, heterociclo, arilo o heteroarilo de 5 o 6 miembros unido directamente al grupo SO2 representado y que tiene una longitud mayor que aproximadamente la de un grupo hexilo e inferior que la de un grupo eicosilo, donde dicho R1 define un volumen tridimensional, cuando rota alrededor de un eje trazado a través de la posición 1 unida a SO2 y la posición 4 de un radical de anillo de 6 miembros o trazado a través de la posición 1 unida a SO2 y el centro de enlace 3,4 de un radical de un anillo de 5 miembros, cuya dimensión más ancha en una dirección transversal al eje de rotación es aproximadamente la de un anillo furanilo hasta aproximadamente la de dos anillos fenilo; o (ii) un grupo -NR7R8 donde R7 y R8 se seleccionan independientemente del grupo formado por hidruro, hidrocarbilo, arilo, arilo sustituido, arilhidrocarbilo, y arilhidrocarbilo sustituido; R2 y R3 se seleccionan independientemente del grupo formado por hidruro, alquilo, alquenilo, alquinilo, hidroxialquilo, Ra oxialquilo, hidroxilo, tiol, Ra tioalquilo, haloalquilo, amino, Rb Rc amino, Rb Rc aminoalquilo, RdRe aminoalcanoilo (Rb) aminoalquilo, RbRc aminoalquiloxi, RbRc aminoalquiloxialquilo, heterociclo, heterocicloalquilo, heterocicloxi, heterociclotio, heteroarilo, heteroarilalquilo, heteroariloxi, heteroariltio, o R2 y R3 junto con el átomo de carbono al cual están unidos forman un anillo carbocíclico o heterocíclico de 4 a 8 miembros, que es preferentemente un anillo de 5 o 6 miembros, donde el heteroátomo es oxígeno, azufre o nitrógeno, donde dicho heteroátomo es opcionalmente sustituido con uno o dos oxígenos cuando es azufre y es opcionalmente sustituido con una porción seleccionada del grupo formado por un grupo hidrocarbilo C1-4, ciclohidrocarbilo C3-6, hidrocarbilocarbonilo C1-4, y sulfonilo hidrocarbilo C1-4 cuando es nitrógeno; R5 y R6 se seleccionan independientemente del grupo formado por un hidruro, alquilo, cicloalquilo, acilalquilo, halo, nitro, hidroxilo, ciano, alcoxi, haloalquilo, haloalquiloxi, hidroxialquilo, un sustituyente RbRc aminoalquilo, tiol, alquiltio, ariltio, cicloalquiltio, cicloalcoxi, alcoxialcoxi, perfluoroalquilo, haloalquilo, heterocicloxi y un sustituyente RbRc aminoalquiloxi; o R5 y R6 junto con los átomos a los cuales están unidos forman otro anillo carbocíclico o heterocíclico alifático o aromático de 5 o 7 miembros; y R20 es (a) -O-R21, donde R21 se selecciona del grupo formado por un grupo hidruro, alquilo C1-6, arilo, ar-alquilo C1-6 y un catión aceptable para uso farmacéutico; (b) -NR13-O-R22 donde R22 es un grupo protector selectivamente removible y R13 es un hidruro, alquilo C1-6 o grupo bencilo; (c) -NR13-O-R14, donde R13 tiene los valores definidos anteriormente y R14 es hidruro, un catión aceptable para uso farmacéutico o C(V)R15 donde V es O o S y R15 se selecciona del grupo formado por alquilo C1-6, arilo, alcoxi C1-6, heteroaril-alquilo C1-6, cicloalquil C3-8-alquilo C1-6, ariloxi, ar -alcoxi C1-6, ar-alquilo C1-6, heteroarilo y un grupo amino alquilo C1-6 donde el nitrógeno del amino alquilo C1-6 es (i) insustituido o (ii) sustituido con uno o dos sustituyentes independientemente seleccionados del grupo formado por un radical alquilo C1-6, arilo, ar-alquilo C1-6, cicloalquil C3-8-alquilo C1-6, ar-alcoxicarbonilo C1-6, alcoxicarbonilo C1-6, y alcanoílo C1-6, o (iii) donde el nitrógeno del amino alquilo C1-6 y dos sustituyentes unidos al mismo forman un anillo heterociclo o heteroarilo de 5 a 8 miembros, o (d) -NR23R24, donde R23 y R24 se seleccionan independientemente del grupo formado por un grupo hidruro, alquilo C1-6, amino-alquilo C1-6, hidroxi-alquilo C1-6, arilo, y un grupo ar-alquilo C1-6, o R23 y R24 junto con el átomo de nitrógeno representado forman un anillo de 5 a 8 miembros que contiene 0 o un heteroátomo adicional que es oxígeno, nitrógeno o azufre; donde: Ra se selecciona del grupo formado por un hidruro, alquilo, alquenilo, alquinilo, arilalquilo, arilo, alcanoílo, aroílo, arilalquilcarbonilo, RbRc aminoalquilo, alcoxialquilo, haloalquilo y un grupo arilalquiloxi; Rb y Rc se seleccionan independientemente del grupo formado por un hidruro, alcanoílo, arilalquilo, aroílo, bisalcoxialquilo, alquilo, haloalquilo, perfluoroalquilo, trifluorometilalquilo, perfluoroalcoxialquilo, alcoxialquilo, cicloalquilo, heterocicloalquilo, heterocicloalquilcarbonilo, arilo, heterociclo, heteroarilo, cicloalquilalquilo, ariloxialquilo, heteroariloxialquilo, heteroarilalcoxialquilo, heteroariltioalquilo, arilsulfonilo, aralcanoílo, alquilsulfonilo, heteroarilsulfonilo, carboxialquilo, alcoxicarbonilalquilo, aminocarbonilo, alquiliminocarbonilo, ariliminocarbonilo, heterocicloiminocarbonilo, ariltioalquilo, alquiltioalquilo, ariltioalquenilo, alquiltioalquenilo, heteroarilalquilo, haloalcanoílo, hidroxialcanoílo, tioalcanoílo, alquenilo, alquinilo, alcoxialquilo, alcoxicarbonilo, ariloxicarbonilo, aminoalquilcarbonilo, hidroxialquilo, aminoalquilo, aminoalquilsulfonilo, aminosulfonilo donde el nitrógeno del amino es (i) insustituido o (ii) sustituido independientemente con uno o dos radicales Rd, o los sustituyentes en el grupo amino tomados junto con el nitrógeno del amino forman un grupo heterociclo saturado o parcialmente insaturado opcionalmente sustituido con 1, 2 o 3 grupos seleccionados independientemente entre sustituyentes Rd o un grupo heteroarilo opcionalmente sustituido con 1, 2 o 3 grupos seleccionados independientemente entre sustituyentes Rf; Rc y Re se seleccionan independientemente del grupo formado por un hidruro, alquilo, alquenilo, alquinilo, arilalquilo, arilo, alcanoílo, aroílo, arilalquilcarbonilo, alcoxicarbonilo y un grupo arilalquiloxicarbonilo; y Rf se selecciona del grupo formado por un grupo nitro, hidroxi, alquilo, halógeno, arilo, alcoxi, ciano, y un RdRe amino. Estos compuestos se usan en la fabricación de medicamentos para inhibir la actividad de metaloproteinasas de matriz en un huésped que padece una afección relacionada con la actividad patológica de metaloproteinasas de matriz.
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