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AR039564A1 - Derivados de carbonilamino como inhibidores de desacetilasa de histona, composiciones farmaceuticas y procesos de preparacion del compuesto y de las composiciones que lo contienen - Google Patents

Derivados de carbonilamino como inhibidores de desacetilasa de histona, composiciones farmaceuticas y procesos de preparacion del compuesto y de las composiciones que lo contienen

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Publication number
AR039564A1
AR039564A1 ARP030100852A ARP030100852A AR039564A1 AR 039564 A1 AR039564 A1 AR 039564A1 AR P030100852 A ARP030100852 A AR P030100852A AR P030100852 A ARP030100852 A AR P030100852A AR 039564 A1 AR039564 A1 AR 039564A1
Authority
AR
Argentina
Prior art keywords
alkyl
amino
alkyloxy
aminoalkyl
aminoc
Prior art date
Application number
ARP030100852A
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 AR039564A1 publication Critical patent/AR039564A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—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
    • C07D413/12—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 chain containing hetero atoms as chain links
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/402—1-aryl substituted, e.g. piretanide
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Abstract

Compuestos de la fórmula (1) que poseen actividad enzimática de inhibición de desacetilasa de histona; su proceso de preparación, composiciones que los contienen y una combinación de agentes anticancerosos. Estos compuestos pueden utilizarse como una medicina para inhibir condiciones proliferativas tales como cáncer y psoriasis. Reivindicación 1: Un compuesto de fórmula (1), las formas N-óxido, las sales de adición farmacéuticamente aceptables y las formas estereoquímicamente isoméricas de los mismos, en la cual n es 0,1, 2 o 3 y cuando n es 0 entonces se quiere significar un enlace directo; m es 0 o 1 y cuando m es 0 entonces se quiere significar un enlace directo; t es 0, 1, 2, 3 o 4 y cuando t es 0 entonces se quiere significar un enlace directo; cada Q es nitrógeno o carbono; cada X es nitrógeno o carbono; cada Y es nitrógeno o carbono; R1 es -C(O)NR8R9, -NHC(O)R10, -C(O)-C1-6alcanodiiloSR10, -NR11C(O)N(OH)R10, -NR11C(O)C1-6alcanodiiloSR10, -NR11C(O)C=N (OH)R10 u otro grupo quelante de cinc, en donde R8 y R9 se seleccionan cada uno independientemente de hidrógeno, hidroxi, alquilo C1-6, hidroxialquilo C1-6, aminoalquilo C1-6 o aminoarilo; R10 es hidrógeno, alquilo C1-6, alquil C1-6-carbonilo, arilalquilo C1-6, alquil C1-6-pirazinilo, piridinona, pirrolidinona o metilimidazolilo; R11 es hidrógeno o alquilo C1-6 ;R2 es hidrógeno, halo, hidroxi, amino, nitro, alquilo C1-6, alquiloxilo C1-6, trifluorometilo, di(alquil C1-6)-amino, hidroxiamino o naftalenilsulfonilpirazinilo; -L- es un enlace directo o un radical bivalente seleccionado de alcanodiilo C1-6, alcanodiiloxi C1-6, amino, carbonilo o aminocarbonilo; cada R3 representa independientemente un átomo de hidrógeno y un átomo de hidrógeno puede ser reemplazado por un substituyente seleccionado de arilo; R4 es hidrógeno, hidroxilo, amino, hidroxialquilo C1-6, alquilo C1-6, alquiloxilo C1-6, arilalquilo C1-6, aminocarbonilo, hidroxicarbonilo, aminoalquilo C1-6, aminocarbonilalquilo C1-6, hidroxicarbonilalquilo C1-6, hidroxiaminocarbonilo, alquiloxi C1-6-carbonilo, alquil C1-6-aminoalquilo C1-6 o di(alquil C1-6)aminoalquilo C1-6; R5 es hidrógeno, alquilo C1-6, cicloalquilo C3-10, hidroxialquilo C1-6, alquiloxi C1-6-alquilo C1-6, di(alquil C1-6)aminoalquilo C1-6 o arilo; la parte cíclica A es un radical seleccionado entre los restos de fórmula (a-1) a (a-51) en los cuales cada s es independientemente 0, 1, 2, 3, 4 o 5; cada R6 y R7 son independientemente seleccionados de hidrógeno; halo; hidroxilo; amino; nitro; trihaloalquilo C1-6; trihaloalquiloxilo C1-6; alquilo C1-6; alquilo C1-6 substituido con arilo y cicloalquilo C3-10; alquiloxilo C1-6; alquiloxi C1-6-alquiloxilo C1-6; alquil C1-6-carbonilo; alquiloxi C1-6-carbonilo; alquil C1-6-sulfonilo; cianoalquilo C1-6; hidroxialquilo C1-6 ; hidroxialquiloxilo C1-6; hidroxialquil C1-6-amino; aminoalquiloxilo C1-6; di(alquil C1-6)aminocarbonilo; di(hidroxialquil C1-6) amino; (aril)(alquil C1-6)amino; di(alquil C1-6)aminoalquiloxilo C1-6; di(alquil C1-6)aminoalquil C1-6amino; di(alquil C1-6)aminoalquil C1-6-aminoalquilo C1-6; arilsulfonilo; arilsulfonilamino; ariloxilo; ariloxialquilo C1-6 ;arilalquenodiilo C2-6; di(alquil C1-6)amino; di(alquil C1-6)aminoalquilo C1-6; di(alquil C1-6)amino(alquil C1-6)amino; di(alquil C1-6)amino(alquil C1-6)aminoalquilo C1-6; di(alquil C1-6)aminoalquilo C1-6(alquil C1-6)amino; di(alquil C1-6)aminoalquil C1-6(alquil C1-6)aminoalquilo C1-6; aminosulfonilamino(alquil C1-6)amino; aminosulfonilamino(alquil C1-6)aminoalquilo C1-6; di(alquil C1-6)aminosulfonilamino(alquil C1-6)amino; di(alquil C1-6)aminosulfonilamino(alquil C1-6)aminoalquilo C1-6; ciano; tiofenilo; tiofenilo substituido con di(alquil C1-6)aminoalquil C1-6(alquil C1-6)aminoalquilo C1-6, di(alquil C1-6)aminoalquilo C1-6, alquil C1-6-piperazinilalquilo C1-6, hidroxialquil C1-6-piperazinilalquilo C1-6, hidroxialquiloxi C1-6-alquil C1-6-piperazinilalquilo C1-6, di(alquil C1-6)aminosulfonilpiperazinilalquilo C1-6, alquiloxi C1-6-piperidinilo, alquiloxi C1-6-piperidinilalquilo C1-6, morfolinilalquilo C1-6, hidroxialquil C1-6(alquil C1-6)aminoalquilo C1-6, o di(hidroxialquil C1-6)aminoalquilo C1-6; furanilo; furanilo substituido con hidroxialquilo C1-6; benzofuranilo; imidazolilo; oxazolilo; oxazolilo substituido con arilo y alquilo C1-6 ; alquil C1-6-triazolilo; tetrazolilo; pirrolidinilo; pirrolilo; piperidinilalquiloxilo C1-6 ; morfolinilo; alquil C1-6-morfolinilo; morfolinilalquiloxilo C1-6; morfolinilalquilo C1-6; morfolinilalquil C1-6-amino; morfolinil C1-6-alquilaminoalquilo C1-6; piperazinilo; alquil C1-6-piperazinilo; alquil C1-6-piperazinilalquiloxilo C1-6; piperazinilalquilo C1-6; naftalenilsulfonilpiperazinilo; naftalenilsulfonilpiperidinilo; naftalenilsulfonilo; alquil C1-6-piperazinilalquilo C1-6; alquil C1-6-piperazinilalquil C1-6-amino; alquil C1-6-piperazinilalquil C1-6-aminoalquilo C1-6; alquil C1-6-piperazinilsulfonilo; aminosulfonilpiperazinilalquiloxilo C1-6; aminosulfonilpiperazinilo; aminosulfonilpiperazinilalquilo C1-6; di(alquilo C1-6)aminosulfonilpiperazinilo; di(alquil C1-6)aminosulfonilpiperazinilalquilo C1-6; hidroxialquil C1-6-piperazinilo; hidroxialquil C1-6-piperazinilalquilo C1-6; alquiloxi C1-6-piperidinilo; alquiloxi C1-6-piperidinilalquilo C1-6; piperidinilaminoalquil C1-6-amino; piperdinilaminoalquil C1-6-aminoalquilo C1-6; (alquil C1-6piperdinil)(hidroxialquil C1-6)aminoalquil C1-6-amino; (alquil C1-6-piperidinil)(hidroxialquil C1-6)aminoalquil C1-6-aminoalquilo C1-6; hidroxialquiloxi C1-6-alquil C1-6-piperazinilo; hidroxialquiloxi C1-6-alquil C1-6-piperazinilalquilo C1-6; (hidroxialquil C1-6)(alquil C1-6)amino; (hidroxialquil C1-6)(alquil C1-6)-aminoalquilo C1-6; hidroxialquil C1-6-aminoalquilo C1-6; di(hidroxialquil C1-6)aminoalquilo C1-6; pirrolidinilalquilo C1-6; pirrolidinilalquiloxilo C1-6; pirazolilo; tiopirazolilo; pirazolilo substituido con dos substituyentes seleccionados de alquilo C1-6 o trihaloalquilo C1-6; piridinilo; piridinilo substituido con alquiloxilo C1-6, ariloxilo o arilo; pirimidinilo; tetrahidropirimidinilpiperazinilo; tetrahidropirimidinilpiperazinilalquilo C1-6; quinolinilo; indol; fenilo; o fenilo substituido con uno, dos o tres substituyentes independientemente seleccionados de halo, amino, nitro, alquilo C1-6, alquiloxilo C1-6, hidroxialquilo C1-4, trifluorometilo, trifluorometiloxilo, hidroxialquiloxilo C1-4, alquil C1-4-sulfonilo, alquiloxi C1-4-alquiloxilo C1-4, alquiloxi C1-4-carbonilo, aminoalquiloxilo C1-4, di(alquil C1-4)-aminoalquiloxilo C1-4, di(alquil C1-4)amino, di(alquil C1-4)aminocarbonilo, di(alquil C1-4)aminoalquilo C1-4, di(alquil C1-4)aminoalquil C1-4-aminoalquilo C1-4, di(alquil C1-4)amino(alquil C1-4)amino, di(alquil C1-4)amino(alquil C1-4)aminoalquilo C1-4, di(alquil C1-4)aminoalquil C1-4(alquil C1-4)amino, di(alquil C1-4)aminoalquil C1-4(alquil C1-4)aminoalquilo C1-4, aminosulfonilamino(alquil C1-4)amino, aminosulfonilamino(alquil C1-4)aminoalquilo C1-4, di(alquil C1-4)aminosulfonilamino(alquil C1-4)amino, di(alquil C1-4)aminosulfonilamino(alquil C1-4)aminoalquilo C1-6, ciano, piperidinilalquiloxilo C1-4, pirrolidinilalquiloxilo C1-4, aminosulfonilpiperazinilo, aminosulfonilpiperazinilalquilo C1-4, di(alquil C1-4)aminosulfonilpiperazinilo, di(alquil C1-4)aminosulfonilpiperazinilalquilo C1-4, hidroxialquil C1-4-piperazinilo, hidroxialquil C1-4-piperazinilalquilo C1-4, alquiloxi C1-4-piperidinilo, alquiloxi C1-4-piperidinilalquilo C1-4, hidroxialquiloxi C1-4-alquil C1-4-piperazinilo, hidroxialquiloxi C1-4-alquil C1-4-piperaziniloalquilo C1-4, (hidroxialquil C1-4)(alquil C1-4)amino, (hidroxialquil C1-4)(alquil C1-4)aminoalquilo C1-4, di(hidroxialquil C1-4)amino, di(hidroxialquil C1-4)aminoalquilo C1-4, furanilo, furanilo substituido con -CH=CH-CH=CH-, pirrolidinilalquilo C1-4, pirrolidiniloalquiloxi C1-4, morfolinilo, morfolinilalquiloxilo C1-4, morfolinilalquilo C1-4, morfolinilalquil C1-4-amino, morfolinilalquil C1-4-aminoalquilo C1-4, piperazinilo, alquil C1-4-piperazinilo, alquil C1-4-piperazinilalquiloxilo C1-4, piperazinilalquilo C1-4, alquil C1-4-piperazinilalquilo C1-4, alquil C1-4-piperazinilalquil C1-4-amino, alquil C1-4-piperazinilalquil C1-4-aminoalquilo C1-6, tetrahidropirimidinilpiperazinilo, tetrahidropirimidinilpiperaziniloalquilo C1-4, piperidinilaminoalquil C1-4-amino, piperidinilaminoalquil C1-4-amino-C1-4alquilo, (alquil C1-4-piperidinilo)(hidroxialquil C1-4)aminoalquil C1-4-amino, (alquil C1-4-piperidinil)(hidroxialquil C1-4)aminoalquil C1-4-aminoalquil C1-4piridinilalquiloxilo C1-4, hidroxialquil C1-4-amino, hidroxialquil C1-4-aminoalquilo C1-4, di(alquil C1-4)aminoalquil C1-4-amino, aminotiadiazolilo, aminosulfonilpiperazinilalquiloxilo C1-4, o tiofenilalquil C1-4-amino; pudiendo cada R6 y R7 estar ubicado sobre el nitrógeno en reemplazo del hidrógeno; arilo en la anterior es fenilo, o fenilo substituido con uno o más substituyentes seleccionados cada uno independientemente de halo, alquilo C1-6, alquiloxi C1-6, trifluorometilo, ciano o hidroxicarbonilo. Reivindicación 11: Un procedimiento para la preparación de un compuesto de acuerdo con la reivindicación 1, caracterizado porque se hace reaccionar un intermediario de la fórmula (2) con un ácido apropiado, tal como por ejemplo, ácido trifluoroacético (CF3COOH), produciendo un ácido hidroxámico de la fórmula (3), en la cual R1 es -C(O)NH(OH).
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