AR085013A1 - Derivados de acido 3-heteroaroilamino-propionico sustituidos y su uso como sustancias farmaceuticas - Google Patents

Derivados de acido 3-heteroaroilamino-propionico sustituidos y su uso como sustancias farmaceuticas

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Publication number
AR085013A1
AR085013A1 ARP120100225A AR085013A1 AR 085013 A1 AR085013 A1 AR 085013A1 AR P120100225 A ARP120100225 A AR P120100225A AR 085013 A1 AR085013 A1 AR 085013A1
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Argentina
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Sanofi Aventis
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    • C07D213/00—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
    • C07D213/02—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
    • C07D213/04—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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
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    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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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

Derivados de ácido 3-heteroaroilamino-propiónico sustituidos y su uso como sustancias farmacéuticas, que son compuestos farmacéuticos activos valiosos. Son inhibidores de la proteasa catepsina A, y son útiles, por ejemplo, para el tratamiento de enfermedades tales como aterosclerosis, insuficiencia cardiaca, enfermedades renales, enfermedades hepáticas o enfermedades inflamatorias. La presente se refiere además a procedimientos para preparar los compuestos de fórmula (1), a su uso y a composiciones farmacéuticas que los comprenden.Reivindicación 1: Un compuesto de fórmula (1), en cualquiera de sus formas estereoisoméricas o una mezcla de formas estereoisoméricas en cualquier relación, o una sal fisiológicamente aceptable del mismo, o un solvato fisiológicamente aceptable de cualquiera de ellos, en la que A se elige entre la serie que consiste en C(R1) y N; D se elige entre la serie que consiste en C(R2) y N; E se elige entre la serie que consiste en C(R3) y N; L se elige entre la serie que consiste en C(R4) y N; donde al menos uno, y como máximo dos, de A, D, E o L son N; G se elige entre la serie que consiste en R71-O-C(O)-, R72-N(R73)-C(O)- y tetrazol-5-ilo; R1 se elige entre la serie que consiste en hidrógeno, halógeno, alquilo C1-6, HO-, alquil C1-6-O-, alquil C1-6-S(O)m y NC-; R2 se elige entre la serie que consiste en hidrógeno, halógeno, alquilo C1-7, alquil C1-6-O-, alquil C1-6-CO-, alquil C1-6-CO-HN-, -NR12R13, Het2, cicloalquil C3-7-CsH2s- y Ar-CsH2s-, donde s es un número entero elegido entre la serie que consiste en 0, 1, 2 y 3; R3 se elige entre la serie que consiste en hidrógeno, halógeno, alquilo C1-6, alquil C1-6S(O)m, Het4-(O)t-, -NR12R13, Het2, R11-O-, R12-N(R13)-C(O)-O- y Het2-C(O)-O- y NC-, donde s es un número entero elegido entre la serie que consiste en 0, 1, 2 y 3 y donde t es un número entero elegido entre la serie que consiste en 0 y 1; R4 se elige entre la serie que consiste en hidrógeno, halógeno, alquilo C1-6, alquil C1-6-O-, HO-, NR12R13, Het2; R10 se elige entre la serie que consiste en hidrógeno, halógeno, alquilo C1-6, alquil C1-6-O-, alquil C1-6S(O)m, HO-, -NR12R13, Het2, fenil-CsH2s-(O)t-, donde s es un número entero elegido entre la serie que consiste en 0, 1, 2 y 3 y donde t es un número entero elegido entre la serie que consiste en 0 y 1; o R1 y R2 o R2 y R3 o forman piridilo; o R1 y R2 son -C(alquil C1-3)=N-N(alquil C1-3)-; o R2 y R3 son -NH-CH=N-; con la condición de que uno de R1, R2, R3, R4 o R10 sea un sustituyente cíclico; R11 se elige entre la serie que consiste en hidrógeno, R14, cicloalquilo C3-7, Ar y Het3; R12 y R13 se eligen, independientemente entre sí, entre la serie que consiste en hidrógeno y R15; R14 es alquilo C1-10 que está opcionalmente sustituido con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en halógeno, HO-, R16-O-, oxo, cicloalquilo C3-7, Ar, Het1, Het3, NC-, H2N-C(O)-, alquil C1-4-NH-C(O)-, di(alquil C1-4)N-C(O)-, Het1-C(O)-, alquil C1-4-C(O)-NH- y alquil C1-4S(O)m; R15 es alquilo C1-6 que está opcionalmente sustituido con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en halógeno, HO- y alquil C1-6-O-; R16 es alquilo C1-6 que está opcionalmente sustituido con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en HO-, alquil C1-4-O- y NC-; R30 se elige entre la serie que consiste en R31, cicloalquilo C3-7, R32-CuH2u- y Het3-CuH2u-, donde u es un número entero elegido entre la serie que consiste en 0, 1, 2 y 3; R31 es alquilo C1-10 que está opcionalmente sustituido con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en halógeno, cicloalquilo C3-7, HO-, alquil C1-6-O-, alquil C1-6S(O)m- y NC-; R32 se elige entre la serie que consiste en fenilo y un heterociclo monocíclico, aromático, de 5 o de 6 miembros, que comprende uno, dos o tres heteroátomos iguales o diferentes en el anillo elegidos entre la serie que consiste en nitrógeno, oxígeno y azufre, y está unido a través de un átomo de carbono del anillo, donde el fenilo y el heterociclo están opcionalmente sustituidos con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en halógeno, alquilo C1-6, cicloalquilo C3-7, R33, HO-, alquil C1-6-O-, R33-O-, R33-alquil C1-4-O-, -O-CH2-O-, -O-CF2-O-, alquil C1-6S(O)m, H2N-S(O)2-, alquil C1-4-NH-S(O)2-, di(alquil C1-4)N-S(O)2-, H2N-, alquil C1-6-NH-, di(alquil C1-6)N-, Het1, alquil C1-4-C(O)-NH-, Ar-C(O)-NH-, alquil C1-4-S(O)2-NH- y NC-; R33 se elige entre la serie que consiste en fenilo y un heterociclo monocíclico, aromático, de 5 o de 6 miembros, que comprende uno, dos o tres heteroátomos iguales o diferentes en el anillo elegidos entre la serie que consiste en nitrógeno, oxígeno y azufre, y está unido a través de un átomo de carbono del anillo, donde el fenilo y el heterociclo están opcionalmente sustituidos con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en halógeno, alquilo C1-6, cicloalquilo C3-7, HO-, alquil C1-6-O-, alquil C1-6S(O)m-, H2N-S(O)2-, alquil C1-4-NH-S(O)2-, di(alquil C1-4)N-S(O)2- y NC-; R40 se elige entre la serie que consiste en hidrógeno y alquilo C1-4; o R30 y R40 juntos son (CH2)x que está opcionalmente sustituido con uno o más sustituyentes alquilo C1-4 iguales o diferentes, donde x es un número entero elegido entre la serie que consiste en 2, 3, 4 y 5; R50 se elige entre la serie que consiste en hidrógeno, alquilo C1-6, HO- y alquil C1-6-O-; R60 se elige entre la serie que consiste en hidrógeno y alquilo C1-6; o R50 y R60 juntos son (CH2) que está opcionalmente sustituido con uno o más sustituyentes alquilo C1-4 iguales o diferentes, donde y es un número entero elegido entre la serie que consiste en 2, 3, 4 y 5; R71 se elige entre la serie que consiste en hidrógeno y alquilo C1-8 que está opcionalmente sustituido con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en alquil C1-6-O- y alquil C1-6-C(O)-O-; R72 se elige entre la serie que consiste en hidrógeno, alquilo C1-6, cicloalquilo C3-6, -CH2-(CH2)b-cicloalquilo C3-6, Het4 y -(CH2)b-Het4, donde el alquilo o cicloalquilo está opcionalmente sustituido con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en halógeno, HO-, HOOC-, alquil C1-6-O- y alquil C1-6-C(O)-O-, NC-, N(alquilo C1-4)2 y b es 0, 1 ó 2; R73 se elige entre la serie que consiste en hidrógeno y alquilo (C1-6); o R72 y R73 junto con el átomo de nitrógeno al que están unidos forman un heterociclo monocíclico, saturado, de 4 a 7 miembros, que contiene opcionalmente un heteroátomo más en el anillo elegido entre la serie que consiste en nitrógeno, oxígeno y azufre, que está opcionalmente sustituido con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en halógeno, alquilo C1-4, HO- y alquil C1-4-O-; Ar, independientemente de cada uno de los otros grupos Ar, se elige entre la serie que consiste en fenilo y un heterociclo monocíclico aromático de 5 o de 6 miembros que comprende uno, dos o tres heteroátomos de anillo iguales o diferentes elegidos entre la serie que consiste en nitrógeno, oxígeno y azufre, y está unido a través de un átomo de carbono del anillo, donde el fenilo y el heterociclo están opcionalmente sustituidos con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en halógeno, alquilo C1-6, HO-alquilo C1-6, Het4, -(CH2)x-fenilo, alquil C1-6-O-, cicloalquil C3-7-(CH2)x-O-, -CF3, -CO-alquilo C1-6, -NR12R13, Het2, -CO-NR12R13, CO-Het2, alquil C1-6S(O)m, H2N-S(O)2- y NC-; y donde el fenilo puede estar sustituido con -CH=CH-CH=CH-, -O-CH2-O-, -O-CH2-CH2-O-, -O-CF2-O- o -N(alquil C1-3)-CH=CH-; Het1, independientemente de cualquier otro grupo Het1, es un heterociclo monocíclico, saturado o insaturado, de 4 a 8 miembros, que comprende un átomo de nitrógeno a través del cual está unido Het1 y opcionalmente uno o dos heteroátomos adicionales iguales o diferentes en el anillo elegidos entre la serie que consiste en nitrógeno, oxígeno y azufre, que está opcionalmente sustituido con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en halógeno, alquilo C1-4, HO-, alquil C1-4-O-, oxo y NC-; Het2 es un heterociclo monocíclico, saturado, de 4 a 7 miembros, que comprende un átomo de nitrógeno a través del cual está unido Het2 y opcionalmente un heteroátomo más en el anillo elegido entre la serie que consiste en nitrógeno, oxígeno y azufre, que está opcionalmente sustituido con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en halógeno, alquilo C1-4, HO- y alquil C1-4-O-; Het3, independientemente de cualquier otro grupo Het3, es un heterociclo monocíclico, saturado, de 4 miembros a 7 miembros, que comprende uno o dos heteroátomos iguales o diferentes en el anillo elegidos entre la serie que consiste en nitrógeno, oxígeno y azufre, y está unido a través de un átomo de carbono del anillo, que está opcionalmente sustituido con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en flúor, alquilo C1-4 y oxo; Het4, independientemente de cualquier otro grupo Het4, es un heterociclo monocíclico, saturado o insaturado, de 4 a 8 miembros, que comprende de uno a cuatro heteroátomos en el anillo elegidos entre la serie que consiste en nitrógeno, oxígeno y azufre que está opcionalmente sustituido con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en halógeno, alquilo C1-4, HO-, alquil C1-4-O-, oxo y NC-; m, independientemente de cualquier otro número m, es un número entero elegido entre la serie que consiste en 0, 1 y 2; donde todos los grupos cicloalquilo, independientemente entre sí, están opcionalmente sustituidos con uno o más sustituyentes iguales o diferentes elegidos entre la serie que consiste en flúor y alquilo C1-4; donde todos los grupos alquilo, CsH2s, CuH2u, (CH2)x
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