AR039567A1 - Derivados de sulfonilamino como nuevos inhibidores de histona deacetilasa, composicion farmaceutica y procedimiento de preparacion del compuesto - Google Patents

Derivados de sulfonilamino como nuevos inhibidores de histona deacetilasa, composicion farmaceutica y procedimiento de preparacion del compuesto

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Publication number
AR039567A1
AR039567A1 ARP030100855A ARP030100855A AR039567A1 AR 039567 A1 AR039567 A1 AR 039567A1 AR P030100855 A ARP030100855 A AR P030100855A AR P030100855 A ARP030100855 A AR P030100855A AR 039567 A1 AR039567 A1 AR 039567A1
Authority
AR
Argentina
Prior art keywords
alkyl
amino
4alkyl
aminoalkyl
aminoc
Prior art date
Application number
ARP030100855A
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 AR039567A1 publication Critical patent/AR039567A1/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 inhibitoria de histona desacetilasa; su proceso de preparación, composiciones que contienen los mismos y el uso del compuesto para la elaboración de un medicamento para el tratamiento de enfermedades proliferativas. Estos compuestos usados como medicamentos producen inhibiciones proliferativas, tales como cáncer y psoriasis. Reivindicación 1: Un compuesto de formula (1), las formas N-óxido, las sales farmacéuticamente aceptables, o sus formas estereoquímicamente isoméricas del mismo en donde n vale 0,1, 2 o 3 y cuando n es 0 entonces se propone un enlace directo; t vale 0, 1, 2, 3 ó 4 y cuando t es 0 entonces se propone un enlace directo; cada uno de los Q es nitrógeno o carbono; cada uno de los X es nitrógeno o carbono; cada uno de los Y es nitrógeno o carbono; cada uno de los Z es nitrógeno o -CH<; R1 es -C(O)NR8R9, -NHC(O)R10, -C(O)- alcanodiil C1-6SR10, -NR11C(O)N(OH)R10, -NR11C(O)alcanodiil C1-6SR10, -NR11C(O)C=N (OH)R10 u otro grupo quelante de Zn, en donde R8 y R9 se seleccionan de manera independiente entre hidrógeno, hidroxi, alquilo C1-6, hidroxialquilo C1-6, aminoalquilo C1-6 o aminoarilo; R10 se selecciona de forma independiente entre hidrógeno, alquilo C1-6, alquil C1-6carbonilo, arilalquilo C1-6, alquil C1-6pirazinilo, piridinona, pirrolidinona o metilimidazolilo; R11 se selecciona de forma independiente entre hidrógeno o alquilo C1-6; R2 es hidrógeno, halo, hidroxi, amino, nitro, alquilo C1-6, alquiloxi C1-6, trifluorometilo, di (alquil C1-6)-amino, hidroxiamino o naftalensulfonilpirazinilo; cada R3 representa en forma independiente un átomo de hidrógeno y un átomo de hidrógeno puede estar substituido por un substituyente seleccionado entre 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 C1-6carbonilo, alquil C1-6aminoalquilo C1-6 o di (alquil C1-6)aminoalquilo C1-6; la parte cíclica A es un radical seleccionado entre (a-1), a (a-51) en donde cada s es en forma independiente 0,1, 2,3, 4 o 5; cada R6 y R7 se seleccionan en forma independiente entre 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 C1-6alquiloxilo C1-6; alquil C1-6carbonilo; alquiloxi C1-6carbonilo; alquil C1-6sulfonilo; cianoalquilo C1-6; hidroxialquilo C1-6; hidroxialquiloxilo C1-6; hidroxialquil C1-6amino; 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)aminoalquilaminoC1-6; di (alquil C1-6)aminoalquilaminoC1-6 alquilo 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) alquilo 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 alquilo(C1-6)aminoalquilo C1-6, di (alquil C1-6)aminoalquilo C1-6, alquil C1-6piperazinilalquilo C1-6, hidroxialquil C1-6piperazinilalquilo C1-6, hidroxialquiloxi C1-6alquil C1-6piperazinilalquilo C1-6, di(alquil C1-6) aminosulfonilpiperazinilalquilo C1-6, alquiloxi C1-6piperidinilo, alquiloxi C1-6piperidinilalquilo 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 C1-6triazolilo; tetrazolilo; pirrolidinilo; pirrolilo; piperidinilalquiloxilo C1-6; morfolinilo; alquilo C1-6morfolinilo; morfolinilalquiloxilo C1-6; morfolinilalquilo C1-6; morfolinilalquil C1-6amino; morfolinil C1-6alquilaminoalquilo C1-6; piperazinilo; alquil C1-6piperazinilo; alquil C1-6piperazinilalquiloxiloc1-6; piperazinilalquilo C1-6; naftalenilsulfonilpiperazinilo; naftalenilsulfonilpiperidinilo; naftalenilsulfonilo; alquil C1-6piperazinilalquilo C1-6; alquil C1-6piperazinilalquilc1-6amino; alquil C1-6piperazinilalquil C1-6aminoalquilo C1-6; alquil C1-6piperazinilsulfonilo; aminosulfonilpiperazinilalquiloxilo C1-6; aminosulfonilpiperazinilo; aminosulfonilpiperazinilalquilo C1-6; di(alquilo C1-6) aminosulfonilpiperazinilo; di (alquil C1-6)aminosulfonilpiperazinilalquilo C1-6; hidroxialquil C1-6piperazinilo; hidroxialquil C1-6piperazinilalquilo C1-6; alquiloxi C1-6piperidinilo; alquiloxi C1-6piperidinilalquiloc1-6; piperidinilaminoalquil C1-6amino; piperdinilaminoalquil C1-6aminoalquilo C1-6; (alquil C1-6piperidinil)(hidroxialquil C1-6)aminoalquilaminoC1-6; (alquil C1-6piperidinil)(hidroxialquilo C1-6) aminoalquilaminoC1-6 alquilo C1-6; hidroxialquiloxi C1-6alquil C1-6piperazinilo; (hidroxialquil C1-6)piperidinilalquilo C1-6; (hidroxialquil C1-6)amino alquilo 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; tetrahidropiridinilpiperazinilo; 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 C1-4sulfonilo, alquiloxi C1-4alquiloxilo C1-4, alquiloxi C1-4carbonilo, 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, (alquil C1-4)aminoalquil C1-4aminoalquilo C1-4, di (alquil C1-4)aminoalquil C1-4 amino, di (alquil C1-4)aminoalquil C1-4aminoalquilo C1-4, di (alquil C1-4)aminoalquil C1-4amino alquilo 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 C1-4, ciano, piperidinilalquiloxilo C1-4, pirrolidinilalquiloxilo C1-4, aminosulfonilpiperazinilo, aminosulfonilpiperazinilalquilo C1-4, di(alquil C1-4) aminosulfonilpiperazinilo, di (alquil C1-4)aminosulfonilpiperazinilalquilo C1-4, hidroxialquil C1-4piperazinilo, hidroxialquil C1-4piperazinilalquilo C1-4, alquiloxi C1-4piperidinilo, alquiloxi C1-4piperidinilalquilo C1-4, hidroxialquiloxi C1-4alquil C1-4piperazinilo, hidroxialquiloxi C1-4alquil C1-4piperaziniloalquilo C1-4, (hidroxialquil C1-4)(alquil C1-4) amino, (hidroxialquil C1-4)(alquil C1-4)aminoalquilo C1-4, di(hidroxialquil C1-4) arnino, di(hidroxialquil C1-4) aminoalquilo C1-4, furanilo, furanilo substituido con -CH=CH-CH=CH-, pirrolidinilalquilo C1-4, pirrolidiniloalquiloxilo C1-4, morfolinilo, morfolinilalquiloxilo C1-4, morfolinilalquilo C1-4, morfolinilalquil C1-4amino, morfolinilalquil C1-4aminoalquilo C1-4, piperazinilo, alquil C1-4piperazinilo, alquil C1-4piperazinilalquiloxilo C1-4, piperazinilalquilo C1-4, alquil C1-4piperazinilalquilo C1-4, alquil C1-4piperazinilalquil C1-4amino, alquil C1-4piperazinilalquil C1-4aminoalquilo C1-4, tetrahidropirimidinilpiperazinilo, tetrahidropirimidinilpiperazinilalquilo C1-4, piperidinilaminoalquil C1-4amino, piperidinilaminoalquil C1-4aminoC1-4alquilo, (alquil C1-4piperidinil)(hidroxialquil C1-4)amino, (alquil C1-4piperidinil)(hidroxialquil C1-4)aminoalquil C1-4aminoalquilo C1-4, piridinilalquiloxilo C1-4, hidroxialquil C1-4amino, (hidroxialquil C1-4)aminoalquilo C1-4, di (alquil C1-4)aminoalquil C1-4amino, aminotiadiazolilo, aminosulfonilpiperazinilalquiloxilo C1-4, o tiofenilalquil C1-4amino ; pudiendo cada R6 y R7 estar ubicado sobre el nitrógeno en reemplazo del hidrógeno; arilo en lo anterior es fenilo, o fenilo substituido con uno o más substituyentes seleccionados cada uno independientemente de halo, alquilo C1-6, alquiloxilo C1-6, trifluorometilo, ciano o hidroxicarbonilo. Reivindicación 11: Un procedimiento para la preparación de un compuesto como se reivindica en la reivindicación 1, caracterizado por la reacción un intermediario de la fórmula (2) con un ácido apropiado, tal como por ejemplo, ácido trifluoroacético, proporcionando un rendimiento de un ácido hidroxámico de la fórmula (1-a), en la cual R1 es -C(O)NH(OH).
ARP030100855A 2002-03-13 2003-03-12 Derivados de sulfonilamino como nuevos inhibidores de histona deacetilasa, composicion farmaceutica y procedimiento de preparacion del compuesto AR039567A1 (es)

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