AR046452A1 - Derivados de quinazolina, metodos para su preparacion, composiciones farmaceuticas que los contienen y su uso como medicamento con efecto antiproliferativo - Google Patents

Derivados de quinazolina, metodos para su preparacion, composiciones farmaceuticas que los contienen y su uso como medicamento con efecto antiproliferativo

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AR046452A1
AR046452A1 ARP040104181A ARP040104181A AR046452A1 AR 046452 A1 AR046452 A1 AR 046452A1 AR P040104181 A ARP040104181 A AR P040104181A AR P040104181 A ARP040104181 A AR P040104181A AR 046452 A1 AR046452 A1 AR 046452A1
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alkyl
amino
group
alkylamino
alkoxy
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Robert Bardbury
Jason Kettle
Laurent Hennequin
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Astrazeneca Ab
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    • C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
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    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
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    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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Abstract

La presente se refiere a derivados de quinazolina, composiciones farmacéuticas que los contienen y su uso como medicamento, para la producción de un efecto anti-proliferativo que se produce total o parcialmente por la inhibición de la tirosina quinasa del receptor erbB2 en un animal de sangre caliente tal como el hombre. Reivindicación 1: Un derivado de quinazolina caracterizado porque responde a la fórmula (1) en donde: m es 0, 1 ó 2; cada R1, que puede ser igual o diferente, se selecciona entre hidroxi C1-6-alcoxi, cicloalquil C3-7-oxi y cicloalquil C3-7-alcoxi C1-6, y en donde cualquier grupo CH2 o CH3 dentro de un sustituyente R1 lleva optativamente en cada uno de dichos grupos CH2 o CH3 uno o más sustituyentes halógeno o alquilo C1-6, o un sustituyente seleccionado entre hidroxi y alcoxi C1-6; R2 es H o alquilo C1-4; n es 0, 1, 2, 3 ó 4; cada R3, que puede ser igual o diferente, se selecciona entre ciano, halógeno, alquilo C1-4, trifluorometilo, alcoxi C1-4, alquenilo C2-4 y alquinilo C2-4; X1 se selecciona entre O, S, SO, SO2, N(R7), CH(OR7), CON(R7), N(R7)CO, SO2N(R7), N(R7)SO2, OC(R7)2, C(R)2O, SC(R7)2, C(R7)2S, CO, C(R7)2N(R7) y N(R7)C(R7)2, en donde cada R7, puede ser igual o diferente, es H o alquilo C1-6; Q1 es arilo, o heteroarilo; y en donde Q1 tiene optativamente uno o más sustituyentes, que pueden ser iguales o diferentes, seleccionados entre halógeno, ciano, nitro, hidroxi, amino, carboxi, carbamoilo, sulfamoilo, formilo, mercapto, alquilo C1-6, alquenilo C2-8, alquinilo C2-8, 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, alcanoilo C2-6, alquenoilo C3-6, alquinoilo C3-6, 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, y un grupo de la fórmula -X2-R8 en donde X2 es un enlace directo o se selecciona entre O, CO y N(R9), en donde R9 es H o alquilo C1-6, y R8 es halógeno-alquilo C1-6, hidroxi-alquilo C1-6, carboxi-alquilo C1-6, alcoxi C1-6-alquilo C1-6, ciano-alquilo C1-6, amino-alquilo C1-6, N-alquilamino C1-6-alquilo C1-6, N,N-di[alquil C1-6]amino-alquilo C1-6, alcanoilamino C2-6-alquilo C1-6, N-alquil C1-6-alcanoilamino C2-6-alquilo C1-6, alcoxicarbonilamino C1-6-alquilo C1-6, carbamoil-alquilo C1-6, N-alquilcarbamoil C1-6-alquilo C1-6, N,N-di-[alquil C1-6]carbamoil-alquilo C1-6, alquiltio C1-6-alquilo C1- 6, alquilsulfinil C1-6-alquilo C1-6, alquilsulfonil C1-6-alquilo C1-6, sulfamoil-alquilo C1-6, N-alquilsulfamoil C1-6-alquilo C1-6, N,N-di-alquilsulfamoil C1-6-alquilo C1-6, alcanoil C2-6-alquilo C1-6, alcanoiloxi C2-6-alquilo C1-6 o alcoxicarbonil C1-6-alquilo C1-6, y en donde cualquier grupo CH2 o CH3 dentro de -X1-Q1 lleva optativamente en cada uno de dichos grupos CH2 o CH3 uno o más sustituyentes halógeno o alquilo C1-6 o un sustituyente seleccionado entre hidroxi, ciano, amino, alcoxi C1- 4, alquilamino C1-4 y di-[alquilamino C1-4]; R4, R4a, R5 y R5a, que pueden ser iguales o diferentes, se seleccionan entre H y alquilo C1-6, o R4 y R4a junto con el átomo de C al cual están unidos forman un anillo cicloalquilo C3-7, o R5 y R5a junto con el átomo de C al cual están unidos forman un anillo cicloalquilo C3-7, y en donde cualquier CH2 o CH3 dentro de cualquiera de R4, R4a, R5 y R5a lleva optativamente en cada uno de dichos grupos CH2 o CH3 uno o más halógeno sustituyentes o un sustituyente seleccionado entre hidroxi, ciano, alcoxi C1-6, amino, alcanoilo C2-6, alquilamino C1-6, y di-[alquilamino C1-6]; R6 se selecciona entre H, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-6, cicloalquenilo C3-7, cicloalquenil C3-7-alquilo C1-6, heterociclilo y heterociclil-alquilo C1-6, y en donde cualquier grupo heterociclilo dentro de un sustituyente R6 tiene optativamente uno o más sustituyentes, que pueden ser iguales o diferentes, seleccionados entre halógeno, trifluorometilo, ciano, nitro, hidroxi, amino, formilo, mercapto, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alcoxi C1-6, alquiltio C1-6, alquilsulfinilo C1-6, alquilsulfonilo C1-6, alquilamino C1-6, di-[alquil C1- 6]amino, alcanoilo C2-6, alcanoiloxi C2-6, y entre un grupo de la fórmula: -X3-R10-, en donde X3 es un enlace directo o se selecciona entre O, CO, SO2 y N(R11), en donde R11 es H o alquilo C1-4, y R10 es halógeno-alquilo C1-4, hidroxi-alquilo C1-4, alcoxi C1-4-alquilo C1-4, ciano-alquilo C1-4, amino-alquilo C1-4, N-(alquilamino C1-4)-alquilo C1-4, y N,N-di-[alquil C1-4]amino-alquilo C1-4, y en donde cualquier grupo heterociclilo dentro de un sustituyente R6 tiene optativamente 1 o 2 sustituyentes oxo o tioxo; y en donde cualquier CH2 o CH3 dentro de un R6 sustituyente, distinto de un grupo CH2 dentro de un grupo heterociclilo, lleva optativamente en cada uno de dichos grupos CH2 o CH3 uno o más sustituyentes halógeno o alquilo C1-6 o un sustituyente seleccionado entre hidroxi, ciano, amino, carboxi, carbamoilo, sulfamoilo, alquenilo C2-6, alquinilo C2-6, alcoxi C1-6, alquiltio C1-6, alquilsulfinilo C1-6, alquilsulfonilo C1-6, alquilamino C1-6, di-[alquil C1-6]amino, N- alquilcarbamoilo C1-6, N,N-di-[alquil C1-6]carbamoilo, alcanoilo C2-6, alcanoiloxi C2-6, alcanoilamino C2-6, N-alquil C1-6-alcanoilamino C2-6, N-alquilsulfamoilo C1-6, N,N-di-[alquil C1-6]sulfamoilo, alcansulfonilamino C1-6 y N-alquil C1-6- alcansulfonilamino C1-6, A se selecciona entre H, un grupo de la fórmula Z-(CR12R13)p y R14, en donde p es 1, 2, 3 ó 4; cada R12 y R13, que puede ser igual o diferente, se selecciona entre H, alquilo C1-6, alquenilo C2-6 y alquinilo C2-6, o un grupo R12 y un grupo R13 unidos al mismo átomo de C forman un anillo cicloalquilo C3-7 o cicloalquenilo C3-7, y en donde cualquier CH2 o CH3 dentro de cualquiera de R12 y R13, lleva optativamente en cada uno de dichos grupos CH2 o CH3 uno o más sustituyentes halógeno o alquilo C1-6 o un sustituyente seleccionado entre hidroxi, ciano, alquilo C1-6, alcoxi C1-6, amino, alcanoilo C2-6, alquilamino C1-6 y di-[alquil C1-6]amino; Z se selecciona entre H, OR15, NR16R17, alquilsulfonilo C1-6, alcansulfonilamino C1-6 y N-alquil C1-6-alcansulfonilamino C1-6, en donde cada uno de R15, R16 y R17, que puede ser igual o diferente, se selecciona entre H, alquilo C1-6, alquenilo C2-6, alquinilo C2-6 y alcoxicarbonilo C1-6, o Z es un grupo de la fórmula: Q2-X4- en donde X4 se selecciona entre O, N(R18), SO2 y SO2N(R18), en donde R18 es H o alquilo C1-6, y Q es cicloalquilo C3-7, cicloalquenilo C3-7 o heterociclilo; R14 se selecciona entre H, OR19 y NR16R17, en donde R19 se selecciona entre alquilo C1-6, alquenilo C2-6 y alquinilo C2-6, y en donde R16 y R17 tienen los valores que se han definido, o R14 es un grupo de la fórmula: Q3-X5- en donde X5 se selecciona entre O y N(R20), en donde R20 es H o alquilo C1-6, y Q3 es cicloalquilo C3- 7, cicloalquil C3-7-alquilo C1-6, cicloalquenilo C3-7, cicloalquenil C3-7-alquilo C1-6, heterociclilo y heterociclil-alquilo C1-6 o R14 es Q4 en donde Q4 es cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-6, cicloalquenilo C3-7, cicloalquenil C3-7- alquilo C1-6, heterociclilo o heterociclil-alquilo C1-6, y en donde los átomos de C contiguos en cualquier cadena alquileno C2-6 dentro de un sustituyente Z o R14 se separan optativamente por la inserción en la cadena de un grupo seleccionado entre O, S, SO, SO2, N(R21), CO, -C=C- y -CsC-, en donde R21 es H o alquilo C1-6, y en donde cualquier grupo heterociclilo dentro de un sustituyente Z o R14 tiene optativamente uno o más sustituyentes, que pueden ser iguales o diferentes, seleccionados entre halógeno, trifluorometilo, ciano, nitro, hidroxi, amino, formilo, mercapto, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alcoxi C1-6, alquiltio C1-6, alquilsulfinilo C1-6, alquilsulfonilo C1-6, alquilamino C1-6, di-[alquil C1-4]amino, alcanoilo C2-6, alcanoiloxi C2-6 y entre un grupo de la fórmula: -X6-R22- en donde X6 es un enlace directo o se selecciona entre O, CO, SO2 y N(R23), en donde R23 es H o alquilo C1-4, y R22 es halógeno-alquilo C1-4, hidroxi-alquilo C1-4, alcoxi C1-4- alquilo C1-4, ciano-alquilo C1-4, amino-alquilo C1-4, N-alquilamino C1-4-alquilo C1-4 y N,N-di[alquil C1-4]amino-alquilo C1-4, y en donde cualquier grupo heterociclilo dentro de un sustituyente Z o R14 tiene optativamente 1 o 2 sustituyentes oxo o tioxo, y en donde cualquier grupo CH2 o CH3 dentro de un grupo Z o R14, distinto de un grupo CH2 dentro de un anillo heterociclilo, lleva optativamente en cada uno de dichos grupos CH2 o CH3 uno o más sustituyentes halógeno o alquilo C1-6 o un sustituyente seleccionado entre hidroxi, ciano, amino, carboxi, carbamoilo, sulfamoilo, alquenilo C2-6, alquinilo C2-6, alcoxi C1-6, alquiltio C1-6, alquilsulfinilo C1-6, alquilsulfonilo C1-6, alquilamino C1-6, di-[alquil C1-6]amino, N- alquilcarbamoilo C1-6, N,N-di[alquil C1-6]carbamoilo, alcanoilo C2-6, alcanoiloxi C2-6, alcanoilamino C2-6, N-alquil C1-6-alcanoilamino C2-6, N-alquilsulfamoilo C1-6, N,N-di-[alquil C1-6]sulfamoilo, alcansulfonilamino C1-6 y N-alquil C1-6- alcansulfonilamino C1-6; una sal aceptable para uso farmacéutico del mismo. Reivindicación 24: Un proceso para la preparación de un derivado de quinazolina de la fórmula (1), o una sal aceptable para uso farmacéutico del mismo, según se define en la reivindicación 1 caracterizado porque comprende: (a) el acoplamiento, convenientemente en la presencia de una base adecuada, de una quinazolina de la fórmula (2) en donde R1, R2, R3, R4, R4a, R5, R5a, R6, X1, Q1, m y n tienen cualquiera de los valores definidos en la reivindicación 1 salvo que si es necesario, los grupos funcionales están protegidos, con un ácido carboxílico de la fórmula A-
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UY28610A1 (es) 2005-06-30
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CN1906178A (zh) 2007-01-31
WO2005051923A1 (en) 2005-06-09
US7625908B2 (en) 2009-12-01
AU2004293250A1 (en) 2005-06-09
US20070244136A1 (en) 2007-10-18
CA2545262A1 (en) 2005-06-09
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