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AR051215A1 - Derivados de quinazolina - Google Patents

Derivados de quinazolina

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Publication number
AR051215A1
AR051215A1 ARP050104277A ARP050104277A AR051215A1 AR 051215 A1 AR051215 A1 AR 051215A1 AR P050104277 A ARP050104277 A AR P050104277A AR P050104277 A ARP050104277 A AR P050104277A AR 051215 A1 AR051215 A1 AR 051215A1
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AR
Argentina
Prior art keywords
6alkyl
alkyl
group
ureido
amino
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ARP050104277A
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English (en)
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Astrazeneca Ab
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Publication of AR051215A1 publication Critical patent/AR051215A1/es

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    • C07D239/72—Quinazolines; Hydrogenated quinazolines
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Abstract

Derivados de quinazolina o una sal aceptable para uso farmacéutico, solvato o prodroga de los mismos, procesos para su preparacion, composiciones farmacéuticas que los contienen y su uso en la elaboracion de un medicamento para usar en el tratamiento de los trastornos de proliferacion celular o en el tratamiento de estados de enfermedad asociados con la angiogénesis y/o la permeabilidad vascular. Reivindicacion 1: Un derivado de quinazolina caracterizado porque responde a la formula (1) en donde X1 es O o N(R7) donde R7 es H o C1-8 alquilo; p es 0, 1, 2 o 3; cada grupo R1, que pueden ser iguales o diferentes, se seleccionan entre halogeno, trifluorometilo, ciano, hidroxi, mercapto, amino, C1-8 alquilo, C2-8 alquenilo, C2-8 alquinilo, C1-6 alcoxi., C2-6 alqueniloxi, C2-6 alquiniloxi, C1-6 alquiltio, C1-6 alquilsulfinilo, C1-6 alquilsulfonilo, C1-6 alquilamino y di[(C1-6)alquil]amino, o entre un grupo de la formula Q1-X2-, en donde X2 es un enlace directo o se selecciona entre O, S, SO, SO2, N(R8), CO, CON(R8), N(R8)CO, OC(R8)2 y N(R8)C(R8)2, en donde cada R8 es H o alquilo C1-8, y Q1 es arilo, aril-C1-6 alquilo, C3-8 cicloalquilo, C3-8 cicloalquil-C1-6alquilo, C3-8 cicloalquenilo, C3-8 cicloalquenil-C1- 6alquilo, heteroarilo, heteroaril-C1-6 alquilo, heterociclilo o heterociclil-C1-6 alquilo; y en donde cualquier grupo arilo, C3-8 cicloalquilo, C3-8 cicloalquenilo, heteroarilo o heterociclilo dentro de un sustituyente R1 tiene opcionalmente 1, 2 o 3 sustituyentes, que pueden ser iguales o diferentes, seleccionados entre halogeno, trifluorometilo, ciano, nitro, hidroxi, amino, carboxi, carbamoílo, ureido, C1-8 alquilo, C2-8 alquenilo, C2-8 alquinilo, C1-6 alcoxi, C2-6 alqueniloxi, C2-6 alquiniloxi, C1-6 alquiltio, C1-6 alquilsulfinilo, C1-6 alquilsulfonilo, C1-6 alquilamino, di-[(C1-6)alquil]amino, C1-6 alcoxicarbonilo, C2-6 alcanoilo, C2-6 alcanoiloxi, N-(C1-6) alquilcarbamoilo, N,N-di-[(C1-6)alquil]carbamoílo, C2-6 alcanoilamino, N-C1-6alquil-C2-6 alcanoilamino., N-C1-6alquilureido,. N'-C1-6 alquilureido, N',N'-di-[(C1-6)alquil]ureido, N,N'-di-[(C1-6)alquil]ureido, N, N', N'-tri-[(C1-6)alquil]ureido, N-C1-6 alquilsulfamoilo, N,N-di[(C1-6)alquil]sulfamoilo, C1- 6 alcansulfonilamino y N-C1-6alquil-C1-6alcansulfonilamino, o entre un grupo de formula -X3-R9 en donde X3 es un enlace directo o se selecciona entre O y N(R10), en donde R10 es H o C1-8 alquilo, y R9 es halogeno-C1-6alquilo, hidroxi-C1-6alquilo, mercapto-C1-6alquilo, C1-6alcoxi-C1-6alquilo, C1-6alquiltio-C1-6alquilo, C1-6alquilsulfinil-C1-6alquilo, C1-6alquilsulfonil-C1-6alquilo, ciano-C1-6alquilo, amino-C1-6alquilo, C1-6lquilamino-C1-6alquilo, di-[(C1-6)alquil]amino-C1-6alquilo, C2- 6alcanoilamino-C1-6alquilo, N-C1-6alquil-C1-6alcanoilamino-C1-6alquilo, C1-6alcoxicarbonilamino-C1-6alquilo, ureido-C1-6alquilo, N-C1-6alquilureido-C1-6alquilo, N'-C1-6alquilureido-C1-6alquilo, N',N'-di-[(C1-6)alquil]ureido-C1-6alquilo, N,N'-di[(C1- 6)alquil]ureido-C1-6alquilo o N,N',N'-tri[(C1-6)alquilureido-C1-6alquilo o entre un grupo de la formula -X4-Q2 en donde X4 es un enlace directo o se selecciona entre O, CO y N(R11), en donde R11 es H o alquilo C1-8, y Q2 es arilo, aril-C1-6 alquilo, heteroarilo, heteroaril-C1-6 alquilo, heterociclilo o heterociclil-C1-6 alquilo que tiene opcionalmente 1 o 2 sustituyentes, que pueden ser iguales o diferentes, seleccionados entre halogeno, hidroxi, C1-8 alquilo y C1-6 alcoxi, y en donde cualquier grupo arilo, heteroarilo o heterociclilo dentro de un sustituyente R1 tiene opcionalmente un grupo C1-3 alquilendioxi, y en donde cualquier grupo heterociclilo dentro de un sustituyente R1 tiene opcionalmente 1 o 2 sustituyentes oxo o tioxo, y en donde cualquier grupo CH, CH2 o CH3 dentro de un sustituyente R1 tiene opcionalmente en cada uno de dichos grupos CH, CH2 o CH3 uno o más sustituyentes halogeno o C1-8 alquilo y/o un sustituyente seleccionado entre hidroxi, mercapto, amino, ciano, carboxi, carbamoílo, ureido, C1-6 alcoxi, C1-6 alquiltio, C1-6 alquilsulfinilo, C1-6 alquilsulfonilo, C1-6 alquilamino, di-[(C1-6)alquil]amino, C1-6 alcoxicarbonilo, N-(C1-6) alquilcarbamoilo, N,N-di-[(C1-6)alquil]carbamoilo, C2-6 alcanoilo, C2-6 alcanoiloxi, C2-6 alcanoilamino, N-C1-6alquil-C2-6 alcanoilamino, N-C1-6alquilureido, N'-C1-6 alquilureido, N',N'-di-[(C1-6)alquil]ureido, N,N'-di-[(C1-6)alquil]ureido, N, N', N'-tri-[(C1-6)alquil]ureido, N-C1-6 alquilsulfamoilo, N,N-di[(C1- 6)alquil]sulfamoilo, C1-6 alcansulfonilamino y N-C1-6alquil-C1-6alcansulfonilamino, y en donde los carbonos adyacentes en cualquier cadena C2-6 alquileno dentro de un sustituyente R1 están opcionalmente separados por la insercion en la cadena de un grupo seleccionado entre O, S, SO, SO2, N(R12), CO, CH(OR12), CON(R12), N(R12)CO, N(R12)CON(R12), SO2N(R12), N(R12)SO2, CH=CH y C:::C en donde R12 es H o C1-8 alquilo, o cuando el grupo insertado es N(R12), R12 también puede ser C2-6 alcanoilo, q es 0, 1 o 2; cada grupo R2, que pueden ser iguales o diferentes, se selecciona entre halogeno, trifluorometilo, ciano, hidroxi, amino, C1-8 alquilo, C2-8 alquenilo, C2-8 alquinilo, C1-6 alcoxi, C1-6 alquilamino y di-[(C1-6)alquil]amino; R3 es H, alquilo C1-8, C2-8 alquenilo o C2-8 alquinilo; R4 es H, hidroxi, C1-8 alquilo, C2-8 alquenilo o C2-8 alquinilo o un grupo de la formula -X5-R13- en donde X5 es un enlace directo o se selecciona entre O y N(R14), en donde R14 es H o C1-8 alquilo, y R13 es H, C1-8 alquilo, halogeno-C1-6alquilo, hidroxi-C1-6alquilo, C1-6alcoxi-C1-6alquilo, ciano-C1-6alquilo, carboxi-C1-6alquilo, amino-C1-6alquilo, C1-6alquilamino-C1-6alquilo, di-[(C1-6)alquil]amino-C1-6alquilo, carbamoil-C1-6alquilo, N,N-di- [(C16)alquil]carbamoil-C1-6alquilo, C1-6alcoxicarbonil-C1-6alquil, C2-6 alcanoilamino-C1-6alquilo o N-C1-6lquil-C2-6alcanoilamino-C1-6alquilo; o R3 y R4 junto con el átomo de C al cual están unidos forman un grupo C3-8 cicloalquilo; R5 es H, C1-8 alquilo, C2-8 alquenilo o C2-8 alquinilo o un grupo de la formula -X6-R15 en donde X6 es un enlace directo o se selecciona entre O y N(R16), en donde R16 es H o alquilo C1-8, y R15 es halogeno-C1-6alquilo, hidroxi-C1-6alquilo, C1-6alcoxi-C1-6alquilo o ciano-C1-6alquilo; el anillo A es un anillo arilo bicíclico de 10 miembros o monocíclico de 6 miembros o un anillo heteroarilo bicíclico de 9-10 miembros o monocíclico de 5 o 6 miembros con hasta tres heteroátomos en el anillo seleccionados entre O, N y S; r es 0, 1, 2 o 3; y cada grupo R6, que pueden ser iguales o diferentes, se selecciona entre halogeno, trifluorometilo, ciano, hidroxi, mercapto, amino, carboxi, carbamoilo, sulfamoilo, ureido, C1-8 alquilo, C2-8 alquenilo, C2-8 alquinilo, C1-6 alcoxi, C1-6 alquiltio, C1-6 alquilsulfinilo, C1-6 alquilsulfonilo, C1-6 alquilamino, di-[(C1-6)alquil]amino, C1-6 alcoxicarbonilo, C2-6 alcanoilo, C2-6 alcanoiloxi, N-C1-6alquilcarbamoilo, N,N-di[(C1-)alquil]carbamoilo, C2-6 alcanoilamino, N- (C1-6)alquil-C2-6alcanoilamino, N'-C1-6alquilureido, N',N'-di-[(C1-6)alquil]ureido, N-C1-6 alquilsulfamoilo, N,N-di[(C1-6)alquil]sulfamoilo, C1-6 alcansulfonilamino y N-C1-6alquil-C1-6alcansulfonilamino, o entre un grupo de la formula -X7-R17 en donde X7 es un enlace directo o se selecciona entre O y N(R18), en donde R18 es H o alquilo C1-8, y R17 es halogeno-C1-6alquilo, hidroxi-C1-6alquilo, mercapto-C1-6alquilo, C1-6alcoxi-C1-6alquilo, C1-6alquiltio-C1-6alquilo, C1-6alquilsulfinil-C1- 6alquilo, C1-6alquilsulfonil-C1-6alquilo, ciano-C1-6alquilo, amino-C1-6alquilo, C1-6alquilamino-C1-6alquilo, di-[(C1-6)alquil]amino-C1-6alquilo, C2-6alcanoilamino-C1-6alquilo, N-C1-6alquil-C2-6alcanoilamino-C1-6alquilo, carboxi-C1-6alquilo, C1- 6alcoxicarboni-C1-6alquilo, carbamoil-C1-6alquilo, N-C1-6alquilcarbonil-c1-6alquilo, N,N-di-[(C16)alquil]carbamoil-C1-6alquilo, sulfamoil-C1-6lquilo, N-C1-6alquilsulfamoil-c1-6alquilo, N,N-di[(C1-6)alquil]sulfamoil-C1-6alquilo, ureido-C1-6alquilo, N- C1-6alquilureido-C1-6alquilo, N'-C1-6alquilureido-C1-6alquilo, N',N'-di-[(C1-6)alquil]ureido-C1-6alquilo, N,N'-di-[(C1-6)alquil]ureido-C1-6alquilo, N,N',N'-tri-[(C1-6)alquil]ureido-C1-6alquilo, C1-6alcansulfonilamino-C1-6alquilo o N-C1-6alquil-C1- 6alcansulfonilamino-C1-6alquilo, o entre un grupo de la formula -X8-Q3 en donde X8 es un enlace directo o se selecciona entre O, S, SO, SO2, N(R19), CO, CH(OR19), CON(R19), N(R19)CO, N(R19)CON(R19), SO2N(R19), N(R19)SO2, C(R19)2O, C(R19)2S y C(R19)2N(R19), en donde cada R19 es H o C1-8 alquilo, y Q3 es arilo, aril-C1-6alquilo, C3-8 cicloalquilo, C3-8 cicloalquil-C1-6alquilo, C3-8cicloalquenilo, C3-8cicloalquenil-C1-6alquilo, heteroarilo, heteroaril-C1-6alquilo, heterociclilo o heterociclil-C1-6alquilo, o dos grupos R6 forman juntos un grupo bivalente que se extiende sobre posiciones adyacentes en el anillo A seleccionado entre OC(R20)2O, OC(R20)2C(R20)2O; OC(R20)2C(R20)2, C(R20)2OC(R20)2, C(R20)2C(R20)2C(R20)2, C(R20)2C(R20)2C(R20)2C(R20)2, OC(R20)2N(R21), N(R21)c(R20)2N(R21), N(R21)C(R20)2C(R20)2, N(R21)C(R20)2C(R20)2C(R20)2, OC(R20)2C(R20)2N(R21), C(R20)2N(R21)C(R20)2, CO.N(R20)C(R20)2, N(R20)CO.C(R20)2, N(R21)C(R20)2CO, CO.N(R20)CO, N(R21)N(R20)CO, N(R20)CO.N(R20), O.CO.N(R20), O.CO.C(R20)2 y CO.OC(R20)2 en donde cada R20 es H, alquilo C1-8, alquenilo C2-8 o C2-8 alquinilo, y en donde R21 es H, alquilo C1-8, alquenilo C2-8, alquinilo C2-8 o C2-6alcanoilo, y en donde cualquier grupo arilo, C3-8 cicloalquilo, C3-8cicloalquenilo, heteroarilo o heterociclilo dentro de un grupo R6 tiene opcionalmente 1, 2 o 3 sustituyentes, que pueden ser iguales o diferentes, seleccionados entre halogeno, trifluorometilo, ciano, nitro, hidroxi, amino, carboxi, carbamoílo, ureido, C1-8 alquilo, C2-8 alquenilo, C2-8 alquinilo, C1-6 alcoxi, C2-6 alqueniloxi, C2-6 alquiniloxi, C1-6 alquiltio, C1-6 alquilsulfinilo, C1-6 alquilsulfonilo, C1-6 alquilamino, di-[(C1-6)alquil]amino, C1-6 alcoxicarbonilo, C2-6 alcanoilo, C2-6 alcanoiloxi, N-(C1-6) alquilcarbamoilo, N,N-di-[(C1-6)alquil]carbamoílo, C2-6 alcanoilamino, N-C1-6alquil-C2-6 alcanoilamino., N'-C1-6
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JP2008515959A (ja) 2008-05-15
CN101072758A (zh) 2007-11-14
EP1802591B1 (en) 2012-01-11
ES2378772T3 (es) 2012-04-17
AU2005293336A1 (en) 2006-04-20
BRPI0516093A (pt) 2008-08-19
IL182094A0 (en) 2007-07-24
EP1802591A1 (en) 2007-07-04
JP4237242B2 (ja) 2009-03-11
WO2006040520A1 (en) 2006-04-20
TW200630347A (en) 2006-09-01
CA2581516C (en) 2013-06-11
CA2581516A1 (en) 2006-04-20
US8153643B2 (en) 2012-04-10
ATE540935T1 (de) 2012-01-15
NZ554017A (en) 2010-06-25
ZA200702877B (en) 2008-09-25
US20090233924A1 (en) 2009-09-17
KR20070084172A (ko) 2007-08-24
MX2007004403A (es) 2007-04-27
CN101072758B (zh) 2013-07-31
NO20071703L (no) 2007-07-04
HK1107339A1 (en) 2008-04-03

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