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AR035065A1 - Derivados de quinolina y quinolinona, uso de dichos compuestos en la fabricacion de medicamentos, composiciones farmaceuticas que comprenden dichos compuestos, proceso para preparar dichas composiciones y procedimiento para la preparacion de dichos compuestos - Google Patents

Derivados de quinolina y quinolinona, uso de dichos compuestos en la fabricacion de medicamentos, composiciones farmaceuticas que comprenden dichos compuestos, proceso para preparar dichas composiciones y procedimiento para la preparacion de dichos compuestos

Info

Publication number
AR035065A1
AR035065A1 ARP010104629A ARP010104629A AR035065A1 AR 035065 A1 AR035065 A1 AR 035065A1 AR P010104629 A ARP010104629 A AR P010104629A AR P010104629 A ARP010104629 A AR P010104629A AR 035065 A1 AR035065 A1 AR 035065A1
Authority
AR
Argentina
Prior art keywords
alkyl
amino
mono
alkyloxy
alkyloxycarbonyl
Prior art date
Application number
ARP010104629A
Other languages
English (en)
Original Assignee
Janssen Pharmaceutica Nv
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 Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv
Publication of AR035065A1 publication Critical patent/AR035065A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
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    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/18—Halogen atoms or nitro radicals
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    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
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    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/38—Nitrogen atoms
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Abstract

Derivados de quinolina y quinolinona que tienen las fórmulas (1-A) o (1B) respectivamente, formas N-óxido, sales de adición farmacéuticamente aceptables, aminas cuaternarias y formas estereoquímicamente isoméricas de los mismos, en donde: X representa O, C(R6)2 donde R6 es hidrógeno, arilo o alquilo C1-6, opcionalmente sustituido con amino o mono- o di(alquilo C1-6) amino, S o N-R7 donde R7 es amino o hidroxi; R1 representa alquilo C1-6, arilo, tienilo, quinolinilo, cicloalquilo C3-12 o (ciclo C3-12 alquilo) alquilo C1-6, donde la porción cicloalquilo C3-12 puede contener opcionalmente n doble enlace o donde un átomo de carbono en la porción cicloalquilo C3-12 puede estar reemplazada por un átomo de hidrógeno o una porción NR8, donde R8 es hidrógeno, bencilo o alquiloxicarbonilo C1-6; donde uno o más átomos de hidrógeno en una porción alquilo C1-6 o en una porción cicloalquilo C3-12 pueden estar opcionalmente reemplazados con alquilo C1-6, hidroxialquilo C1-6, haloalquilo C1-6, aminoalquilo C1-6, hidroxi, alquiloxi C1-6, arilalquiloxi C1-6, halo, alquiloxicarbonilo C1-6, arilo, amino, mono- o di(alquilo C1-6) amino, alquiloxicarbonilamino C1-6, halo, piperazinilo, piridinilo, morfolinilo, tienilo o un radical bivalente de fórmula -O-, -O-CH2-O o -O-CH2-CH2-O-; o un radical de fórmula (2) en la cual: Z1 es un enlace covalente simple, O, NH o CH2; Z2 es un enlace covalente simple, O, NH o CH2; n es un número entero de 0, 1, 2 o 3; y donde cada átomo de hidrógeno en el anillo fenilo puede estar independientemente reemplazado con halo, hidroxi, alquilo C1-6, alquiloxi C1-6 o hidroxialquilo C1-6; o X o R1 pueden tomarse conjuntamente con el átomo de carbono al cual X y R1 están unidos para formar un radical de fórmula (3), (4) o (5); R2 representa hidrógeno, halo, ciano, alquilo C1-6, alquiloxi C1-6, alquiltio C1-6, alquilcarbonilo, alquiloxicarbonilo C1-6, alquilcarboniloxi C1-6 alquilo C1-6, alquenilo C2-6, hidroxialquenilo C2-6, alquinilo C2-6, hidroxialquinilo C2-6, tri(alquilo C1-6) silanoalquinilo C2-6, mono- o di-(alquilo C1-6) amino, mono- o di(alquiloxi C1-6) alquilo C1-6 amino, mono- o di-(alquiltio C1-6 alquilo C1-6) amino, arilo, arilalquilo C1-6, arilalquinilo C2-6, alquiloxi C1-6, alquilamino C1-6 alquilo C1-6, aminocarbonilo opcionalmente sustituido con alquilo C1-6, alquiloxi C1-6 alquilo C1-6, alquiloxicarbonilo C1-6 alquilo C1-6 o piridinilo C1-6 alquilo, un heterociclo seleccionado entre tienilo, furanilo, pirrolilo, tiazolilo, oxazolilo, imidazolilo, isotiazolilo, isoxazolilo, pirazolilo, piridilo, pirazinilo, piridazinilo, pirimidinilo, piperidinilo y piperazinilo, opcionalmente N-sustituidos con alquiloxi C1-6 alquilo C1-6, morfolinilo, tiomorfolinilo, dioxanilo o ditianilo, un radical -NH-C(=O)R9 en el cual R9 representa alquilo C1-6 opcionalmente sustituido con cicloalquilo C3-12, alquiloxi C1-6, alquiloxicarbonilo C1-6, arilo, ariloxi, tienilo, piridinilo, mono- o di- (alquilo C1-6), amino, alquiltio C1-6, benciltio, piridiniltio o pirimidiniltio, cicloalquilo C3-12, ciclohexenilo, amino, arilcicloalquilamino C3-12, mono- o di (alquilo C1-6) di (alquilo C1-6), amino, mono- o di-alquiloxicarbonilo C1-6 (alquilo C1-6) amino, mono- o di (alquiloxicarbonilo C1-6) amino, mono- o di (alquenilo C2-6) amino, mono- o di (ariloalquilo C1-6) amino, mono- o di-arilamino, arilalquenilo C2-6, furanilalquenilo C2-6, piperidinilo, piperazinilo, indolilo, furilo, benzofurilo, tetrahidrofurilo, indonilo, adamantilo, piridinilo, piperazinilo, arilo, arilalquiltio C1-6 o un radical de fórmula (2), una sulfonamida -NH-SO2-R10 en la cual R10 representa alquilo C1-6, mono- o poli- haloalquilo C1-6, arilalquilo C1-6, arilalquenilo C2-6, arilo, quinolinilo, isoxazolil o di(alquilo C1-6) amino; R3 y R4 representan cada uno independientemente hidrógeno, halo, hidroxi, ciano, alquilo C1-6, alquiloxi C1-6, alquiloxi C1-6 alquilo C1-6, alquilcarbonilo C1-6, alquiloxicarbonilo C1-6, alquenilo C2-6, hidroxi alquenilo C2-6, alquinilo C2-6, hidroxi alquinilo C2-6, tri (alquilo C1-6) silano alquinilo C2-6, amino, mono- o di (alquilo C1-6) amino, mono- o di-(alquiloxi C1-6) alquilo C1-6, mono- o di (alquiltio C1-6 alquilo C1-6) amino, arilo, morfolinilalquilo C1-6 o piperidinilalquilo C1-6; o R2 y R3 pueden tomarse conjuntamente para formar -R2-R3-, que representa un enlace divalente de la fórmula -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -CH=CH-CH=CH-, -Z4-CH=CH-, -CH=CH-Z4-, -Z4-CH2-CH2-CH2-, -CH2-Z4-CH2-CH2-, CH2-CH2-Z4-CH2-, -CH2-CH2-CH2-Z4-, -Z4-CH2-CH2-, -CH2-Z4-CH2- o -CH2-CH2-Z4-, con Z4 siendo O, S, SO2 o NR11 donde R11 es hidrógeno, alquilo C1-6, bencilo o alquiloxicarbonilo C1-6, y donde cada radical divalente está opcionalmente sustituido con alquilo C1-6; o R3 y R4 pueden tomarse conjuntamente para formar un radical divalente de fórmula -CH=CH-CH=CH-o -CH2-CH2-CH2-CH2-; R5 representa hidrógeno, cicloalquilo C3-12, piperinilo, oxa-tienilo, tetrahidrotienilo, arilalquilo C1-6, alquiloxi C1-6 alquilo C1-6, alquiloxicarbonil C1-6 alquilo C1-6 o alquilo C1-6 opcionalmente sustituido con un radical C(=O)NRxRy, en el cual Rx y Ry, cada uno independientemente son hidrógeno, cicloalquilo C3-12, alquinilo C2-6, alquilo C1-6 opcionalmente sustituido con ciano, alquiloxi C1-6, alquiloxicarbonilo C1-6, furanilo, pirrolidinilo, benciltio, piridinilo pirrolilo y tienilo, Y representa O o S; o Y y R5 pueden tomarse conjuntamente para forma =Y-R5- que presenta un radical de fórmula: -CH=N-N= (c-1); -N=N-N= (c-2); o -N-CH=CH- (c-3); arilo representa fenilo o naftilo opcionalmente sustituido con uno o más sustituyentes seleccionados entre halo, hidroxi, alquilo C1-6, alquiloxi C1-6, feniloxi, nitro, amino, tio, alquiltio C1-6, haloalquilo C1-6, polihaloalquilo C1-6, polihaloalquiloxi C1-6, hidroxialquilo C1-6, alquiloxialquilo C1-6, aminoalquilo C1-6, mono o di (alquilo C1-6) amino, mono- o di(alquilo C1-6) amino alquilo C1-6, ciano, -CO-R12, -CO-OR13, -NR13SO2R12, -SO2R13R14, -NR13C(O)R12, -C(O)NR13R14, -SOR12, -SO2R12, donde cada R12, R13 y R14 independientemente representan alquilo C1-6, cicloalquilo C3-6, fenilo, fenilo sustituido con halo, hidroxi, alquilo C1-6, alquiloxi C1-6, haloalquilo C1-6, polihaloalquilo, furanilo, tienilo, pirrolilo, imidazolilo, tiazolilo u oxazolilo; y cuando la porción R1-C(=X) está ligado a otra posición distinta de la posición 7 u 8 entonces dicha posición 7 y 8 puede estar sustituida con R15 y R16 donde cualquiera o ambos de R15 y R16 representan alquilo C1-6, alquiloxi C1-6, o R15 y R16 tomados conjuntamente pueden formar un radical divalente de fórmula -CH=CH-CH=CH. Tales Derivados de quinolina y quinolina exhiben actividad antagonista del receptor metabotrópico de glutamato, y por lo tanto son útiles para tratar o prevenir enfermedades del sistema nervioso central inducidas por glutamato. También se dan a conocer: el uso de dichos compuestos en la fabricación de medicamentos, composiciones farmacéuticas que comprenden dichos compuestos, un proceso para preparar dichas composiciones y un procedimiento para la preparación de dichos compuestos.
ARP010104629A 2000-10-02 2001-10-01 Derivados de quinolina y quinolinona, uso de dichos compuestos en la fabricacion de medicamentos, composiciones farmaceuticas que comprenden dichos compuestos, proceso para preparar dichas composiciones y procedimiento para la preparacion de dichos compuestos AR035065A1 (es)

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