AR043055A1 - Derivados de 1-(4-benzil-piperazin-1-il)-3- fenil-propenona - Google Patents

Derivados de 1-(4-benzil-piperazin-1-il)-3- fenil-propenona

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Publication number
AR043055A1
AR043055A1 ARP030103870A ARP030103870A AR043055A1 AR 043055 A1 AR043055 A1 AR 043055A1 AR P030103870 A ARP030103870 A AR P030103870A AR P030103870 A ARP030103870 A AR P030103870A AR 043055 A1 AR043055 A1 AR 043055A1
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Argentina
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optionally substituted
cyano
hydrogen
group
heterocycloalkyl
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ARP030103870A
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Novartis Ag
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • 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
    • C07D215/16—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Rheumatology (AREA)
  • Transplantation (AREA)
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  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Compuesto que es antagonista de CCR-1, y que encuentra uso farmacéuticamente para el tratamiento de enfermedades y condiciones en donde esté implicado el CCR-1, por ejemplo enfermedades inflamatorias. Reivindicación 1: Un compuesto de la fórmula (1), o una sal o éster farmacéuticamente aceptable del mismo, en donde R, es -X-R10, -X-(R10)2 o -NR11R12; en donde X es un enlazador que comprende un átomo o una cadena que comprende 2, 3 o 4 átomos seleccionados a partir de N, C, O ó S, y en donde, cuando este enlazador comprende dos o más átomos de carbono, el enlazador puede comprender uno o más enlaces C=C o C:::C; en donde, cualquiera de estos átomos tiene hasta dos substituyentes opcionales seleccionados a partir de hidrógeno, oxo, ciano, halo, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, azufre amino; R10 es un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, ciano, halo, nitro o oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, cicloalquilo, heterocicloalquilo, arilo, heteroarilo; R11 y R12 cada uno representan un grupo alquilo inferior conectados entre sí, de tal manera que R1 es un grupo heterocicloalquilo o heteroarilo opcionalmente substituido; R2 y R7 representan uno o más substituyentes unidos al anillo fenilo seleccionados a partir del grupo que consiste en hidrógeno, ciano, halógeno, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo, heteroarilo o un substituyente que forme un sistema de anillo bicíclico del cual el anillo de fenilo con el que está unido forma parte del biciclo, por ejemplo naftilo formador de butadieno, o quinolinilo formador de heterobutadieno, quinoxalinilo o isoquinolinilo; R3 y R4 se seleccionan independientemente a partir del grupo que consiste en hidrógeno, ciano, halógeno, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, cicloalquilo, heterocicloalquilo, arilo; R5 y R6 se seleccionan a partir del grupo que consiste en hidrógeno, ciano, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, cicloalquilo, heterocicloalquilo, arilo; los substituyentes opcionales sobre X son uno o más substituyentes independientemente seleccionados a partir del grupo que consiste en hidrógeno, oxo, ciano, halo, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, amino, azufre, sulfinilo, sulfonilo; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro, oxilo, alquilo inferior, alquenilo inferior, alquinilo inferior, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; los substituyentes opcionales sobre R10 son uno o más substituyentes independientemente seleccionados a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro, oxilo, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; los substituyentes opcionales sobre R11 y R12 son uno o más substituyentes independientemente seleccionados a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro, oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; los substituyentes opcionales sobre R2 y R7 son uno o más substituyentes independientemente seleccionados a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro, oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro, oxilo, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; los substituyentes opcionales sobre R3 y R4 son uno o más substituyentes independientemente seleccionados a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro u oxilo, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; los substituyentes opcionales sobre R5 y R6 son uno o más substituyentes independientemente seleccionados a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, amino, azufre, cicloalquilo, heterocicloalquilo, arilo, imino, oxima; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, hidroxilo, ciano, halógeno, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro u oxilo opcionalmente substituido, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo; en donde los substituyentes opcionalmente substituidos están opcionalmente substituidos una o más veces por un substituyente independientemente seleccionado a partir del grupo que consiste en hidrógeno, oxo, ciano, halógeno, nitro u oxilo, alquilo inferior, alquenilo inferior, alquinilo inferior, carbonilo, amino, azufre, cicloalquilo, heterocicloalquilo, arilo.
ARP030103870A 2002-10-25 2003-10-23 Derivados de 1-(4-benzil-piperazin-1-il)-3- fenil-propenona AR043055A1 (es)

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