AR036034A1 - Compuestos de pirazol fusionado, de aplicacion en el tratamiento de cancer y de enfermedades medidas por la superproduccion de factores tgf-beta; formulaciones farmaceuticas que incluyen dichos compuestos de pirazol fusionado como agente activo; uso de los compuestos mencionados para preparar medica - Google Patents

Compuestos de pirazol fusionado, de aplicacion en el tratamiento de cancer y de enfermedades medidas por la superproduccion de factores tgf-beta; formulaciones farmaceuticas que incluyen dichos compuestos de pirazol fusionado como agente activo; uso de los compuestos mencionados para preparar medica

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AR036034A1
AR036034A1 ARP020101974A ARP020101974A AR036034A1 AR 036034 A1 AR036034 A1 AR 036034A1 AR P020101974 A ARP020101974 A AR P020101974A AR P020101974 A ARP020101974 A AR P020101974A AR 036034 A1 AR036034 A1 AR 036034A1
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alkyl
substituted
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hydrogen
compounds
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Abstract

Compuestos de pirazol y, respectivamente, de pirazol fusionado de fórmula (1) en donde el grupo de fórmula (2) es un anillo saturado de cuatro, cinco o seis miembros y X es C, O ó S; R1 es fenilo sustituido o no sustituido; piridina sustituida o no sustituida; N-óxido de piridina; N-óxido de piridina sustituido o no sustituido; quinolina sustituida o no sustituida; N-óxido de quinolina; N-óxido de quinolina sustituido o no sustituido; naftiridina sustituida o no sustituida; pirazina sustituida o no sustituida; furilo; tiazolilo; imidazolilo sustituido o no sustituido; pirazolilo sustituido o no sustituido; o tiofenilo sustituido o no sustituido; en donde la sustitución puede ser una o más de las siguientes: alquilo C1-6; alquenilo C2-6; alquinilo C2-6; alcoxi C1-6; alqueniloxi C2-6; alquiniloxi C2-6; alquiltio C1-6; alquilsulfinilo C1-6; alquilsulfonilo C1-6; alquilamino C1-6, di-[alquil C1-6]amino; alcoxicarbonilo C1-6; N-alquil C1-6-carbamoilo; N,N-di-[alquil C1-6]carbamoilo; alcanoílo C2-6; alcanoiloxi C2-6; alcanoilamino C2-6; N-alquil C1-6-alcanoilamino C2-6; alquenoilamino C3-6; N-alquil C1-6-alquenoilamino C3-6; alquinoilamino C3-6; N-alquil C1-6-alquinoilamino C3-6; N-alquilsulfamoilo C1-6; N,N-di-[alquil C1-6]sulfamoilo; alcansulfonilamino C1-6; N-alquil C1-6-alcansulfonilamino C1-6; carboxamida; etileno; tiofenilo; aminofenilo; trifluorometilo; halo; trifluorometoxi; hidroximetilo; N-pirrolidino; N-morfolino; feniltio; dialquilaminometilo C1-4; metoxifenilo; amino; hidroxi; carboxilo; fenilo; arilalquilo; R2 es quinolina sustituida o no sustituida; N-óxido de quinolina sustituido o no sustituido; fenilo sustituido o no sustituido; naftaleno sustituido o no sustituido; piridina sustituida o no sustituida; N-óxido de piridina sustituido o no sustituido; quinazolina sustituida o no sustituida; cinolina sustituida o no sustituida; benzodioxol sustituido o no sustituido; benzodioxano sustituido o no sustituido; pirimidina sustituida o no sustituida; benzotiofeno sustituido o no sustituido; o fenantroleno sustituido o no sustituido; en donde la sustitución puede ser en forma independiente uno o más de los siguientes: hidrógeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alquilhaluro C1-6, alcoxi C1-6,alqueniloxi C2-6, alquiniloxi C2-6, alquiltio C1-6, alquilsulfinilo C1-6, alquilsulfonilo C1-6, alquilamino C1-6, di[alquil C1-6]amino, alcoxicarbonilo C1-6, N-alquilcarbamoilo C1-6, N,N-di[alquil C1-6]carbamoilo, aminooxi, N-alquil C1-6-aminooxi, N,N-di[alquil C1-6]aminooxi, alcanoílo C2-6, alcanoiloxi C2-6, alcanoilamino C2-6, N-alquil C1-6-alcanoilamino C2-6, alquenoilamino C3-6, N-alquil C1-6-alquenoilamino C3-6, alquinoilamino C3-6, N-alquil C1-6-alquinoilamino C3-6, sulfamoilo, N-alquilsulfamoilo C1-6, N,N-di[alquil C1-6]sulfamoilo, alcansulfonilamino C1-6, N-alquil C1-6-alcansulfonilamino C1-6, carboxamida, etileno, fenilo, tiofenilo, aminofenilo, feniltio, halo, ciano, piridinilo, arilalquilo, hidroxi, N-pirrolidino, N-morfolino, carboxilo, [5-fenil-1,2,4-oxadiazol-3-il]metoxi, 6-metil-piridazin-3-iloxi, (5-oxo-2-pirrolidinil)metoxi, 2-(4,5-dihidro-1H-imidazolilo), N,N-dialquilcarbamoiloxi, 1-hidroxi-1-metiletilo, 4-fluorofenilo, 3,4-metilendioxifenilo, trifluorometilo, trifluorometoxi, o un grupo de la fórmula X1-(CH2)n(CR10R16)(CH2)m-Q1, en donde: X1 es O, N, S, SO2, NR13, C(O), ó enlace; Q1 es hidrógeno, fenilo, 5-(2,2-difluoro-1,3-benzodioxolilo), C(O)Q5, ó piridilo cuando m y n son independientemente 0-2, excepto cuando uno de ellos es cero, el otro no puede ser 0; Q1 es OR11, NR11R12, halo, N-morfolino, N-piperazino-N'R13, N-imidazolilo, N-pirazolilo, N-triazolilo, N-(4-piperidinilpiperidina), SO2R14, SOR14, NHSO2R15, acetamido, N-ftalimido, N-oxazolidino, N-imidazolino, N-benzoxazolidino, N-pirrolidinonilo, N(N'-metilbencimidazolino), N,N-dialquilamino C1-4-alcoxi C1-4, N-bencimidazolino; cuando m y n son independientemente 0-2, pero uno o el otro de m ó n no es 0; Q5 es hidroxi, metoxi, amino, dietilamino, dimetilamino; R10 es hidrógeno, halo, alquilo C1-6; R11 y R12 son independientemente hidrógeno, alquilo C1-6, alcoxi C1-6, arilalquilo, cicloalquilo C3-8, cicloalquilmetilo C3-8, 4-(N-metilpiperidinilo), piridilo, ó R11 y R10 pueden tomarse juntos para formar un anillo de 4, 5, 6 ó 7 miembros, ó R11 y R12 pueden tomarse juntos para formar un anillo de 3, 4, 5, 6 ó 7 miembros; R13 es hidrógeno, alquilo C1-6, 2-metoxifenilo, 2-piridimidinilo; R14 es 2-pirimidinilo, N-metil-2-imidazolilo, 4-clorofenilo, 2-piridilmetilo; R15 es alquilo C1-6, N-metil-4-imidazolilo; R16 es hidrógeno, halo, arilalquilo, arilo o un grupo de fórmula -C(O)-NR20-(CH2)o(CR21R22)(CH2)p-Q2, donde: Q2 es hidrógeno, 4-imidazolilo, ó C(O)NR24R25 cuando o y p son independientemente 0-2; Q2 es OR23, NR24R25 ó N-morfolino, cuando o y p son independientemente 0-2, pero uno o el otro de o ó p no es 0; R20 es hidrógeno o alquilo C1-6; R21 es hidrógeno, alquilo C1-6, ó R21 y R20 pueden tomarse juntos para formar un anillo de 4, 5, 6 ó 7 miembros; R22 es hidrógeno, alquilo C1-6, arilalquilo, arilo, ó R21 y R22 pueden tomarse juntos para ser un anillo de 3, 4, 5, 6, 7 miembros; R23 es hidrógeno o alquilo C1-6; R24 es hidrógeno, alquilo C1-6, ó R24 y R25 pueden tomarse juntos para formar un anillo de 3, 4, 5, 6 ó 7 miembros, ó R24 y R20 pueden tomarse juntos para formar un anillo de 6 ó 7 miembros; R25 es hidrógeno, alquilo C1-6, o acetilo, o un grupo de la fórmula -C(O)NR30R31, en donde: R30 es hidrógeno, o alquilo C1-6; R31 es hidrógeno, alquilo C1-6, 2-piridilo, piridilmetilo, amino, o hidroxi, o un grupo de la fórmula -NR32R33, en donde: R32 y R33 son cada uno en forma independiente hidrógeno, alquilo C1-6, acetilo, alquilsulfonilo C1-4, ó R32 y R33 pueden tomarse juntos para formar un anillo de 4, 5, 6 ó 7 miembros, o un grupo de fórmula -NR35C(O)X2(CH2)q-Q3, en donde: X2 es CH2, O ó N; q es 2-3 excepto cuando Q3 es un enlace, q es 0-3; Q3 es NR36R37 u OR38, y R35 es hidrógeno, o R35 y Q3 pueden tomarse juntos para formar un anillo de 5 miembros; R36, R37 y R38 son cada uno en forma independiente hidrógeno, o alquilo C1-6 o un fenoxi sustituido con X3, en donde X3 es ciano, carboxamida, N,N-dimetilcarboxamida, N,N-dimetiltiocarboxamida, N,N-dimetilaminometilo, 4-metilpiperazin-1-il-metilo o carboxilato, o un grupo de la fórmula -O-CH2-C(O)NR40-(CH2)r-Q6, en donde: Q6 es NR41R42; r es 2-3; R40 es hidrógeno, o alquilo C1-6; R41 y R42 son hidrógeno, alquilo C1-6, ó R41 y R40 pueden tomarse juntos para formar un anillo de 6 ó 7 miembros, o un grupo de la fórmula -CH=CH-C(O)Q7 en donde: Q7 es hidroxi, metoxi, dimetilamino, o N-piperidinilo; con la condición que cuando uno de R1 ó R2 es fenilo sustituido o no sustituido, el otro no puede ser fenilo sustituido o no sustituido o tiofen-2-ilo, y con la condición que cuando R2 es quinolin-4-ilo, la sustitución en la posición 7 de quinolina no puede incluir arilo, heteroarilo, arilo fusionado, o heteroarilo fusionado; k es 1-8; R3 es uno o más de los siguientes: hidrógeno, alquilo C1-4; alquilhidroxi C1-4, hidroxi, N,N-dialquilamino C1-4-alcoxi C1-4; benciloximetilo; feniloximetilo; oxo; carboxilo; alquilarilo C1-4; benciloxi; acetoxi; aminoalquilo C1-4; alquenilo C2-4; halo; -O-alquilo C1-4. clorofenetilo; acetonitrilo; fenilo sustituido o no sustituido; en donde la sustitución puede ser uno o más de los siguientes: alcoxi C1-6, halo, carboxi o alcoxicarbonilo C1-6; y las sales, ésteres y profármacos farmacéuticamente aceptables de los mismos. Los compuestos tienen aplicación en el tratamiento del cáncer y de enfermedades mediadas por la superproducción de factores TGF-beta. Formulaciones farmacéuticas que incluyen dichos compuestos como agente activo, uso de los compuestos mencionados para preparar medicamentos para el tratamiento de cáncer y métodos para tratar cáncer utilizando dichos compuestos, sus sales ésteres y sus profármacos.
ARP020101974A 2001-05-24 2002-05-27 Compuestos de pirazol fusionado, de aplicacion en el tratamiento de cancer y de enfermedades medidas por la superproduccion de factores tgf-beta; formulaciones farmaceuticas que incluyen dichos compuestos de pirazol fusionado como agente activo; uso de los compuestos mencionados para preparar medica AR036034A1 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US29346401P 2001-05-24 2001-05-24
PCT/US2002/011884 WO2002094833A1 (en) 2001-05-24 2002-05-13 Novel pyrrole derivatives as pharmaceutical agents

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AR036034A1 true AR036034A1 (es) 2004-08-04

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