AR059716A1 - Derivados de quinolina - Google Patents

Derivados de quinolina

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Publication number
AR059716A1
AR059716A1 ARP070100874A ARP070100874A AR059716A1 AR 059716 A1 AR059716 A1 AR 059716A1 AR P070100874 A ARP070100874 A AR P070100874A AR P070100874 A ARP070100874 A AR P070100874A AR 059716 A1 AR059716 A1 AR 059716A1
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Argentina
Prior art keywords
alkyl
ureido
amino
alkanoylamino
carbamoyl
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ARP070100874A
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English (en)
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Frederic Henri Jung
Patrick Ple
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Astrazeneca Ab
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Publication of AR059716A1 publication Critical patent/AR059716A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4

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  • Quinoline Compounds (AREA)

Abstract

Procesos para su preparacion, composiciones farmacéuticas que los contienen y su uso en la elaboracion de un medicamento para usar en el tratamiento de trastornos de proliferacion celular. Reivindicacion 1: Un derivado de quinolina caracterizado porque responde a la formula (1) en donde X1 es O o N(R7) donde R7 es hidrogeno o alquilo C1-8; p es 0, 1,2 o 3; cada grupo R1, que pueden ser iguales o diferentes, se selecciona entre halogeno, trifluorometilo, ciano, hidroxi, mercapto, amino, carboxi, alcoxicarbonilo C16, carbamoilo, alquilo C1-8, 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-[(C1-6 alquil]amino, N-(C1- 6)alquilcarbamoilo, N,N-di-[(C1-6)alquil]carbamoilo, N(C1-6)alquilsulfamoilo, N,N-di-[(C1-6)alquil]sulfamoilo, alcanoilo C2-6, alcanoilamino C2-6 y N-(C1-6)alquil-alcanoilamino C2-6, o entre un grupo de la formula: Q1-X2- en donde X2 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 hidrogeno o alquilo C1-8, y Q1 es arilo, aril-(C1-6)alquilo, cicloalquilo C3-8, cicloalquil C3-8-alquilo C1-6, cicloalquenilo C3-8, cicloalquenil C3-8- alquilo C1-6, heteroarilo, heteroaril-(C1-6)alquilo, heterociclilo o heterociclil-(C1-6)alquilo, y en donde cualquier grupo arilo, cicloalquilo C3-8, cicloalquenilo C3-8, heteroarilo o heterociclilo dentro de un sustituyente R1 lleva opcionalmente 1, 2 o 3 sustituyentes, que pueden ser iguales o diferentes, seleccionados entre halogeno, trifluorometilo, ciano, nitro, hidroxi, amino, carboxi, carbamoilo, ureido, alquilo C1-8, 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-[(C1-6 alquil]amino, alcoxicarbonilo C1-6, alcanoilo C2-6, alcanoiloxi C2-6, N-(C1-6)alquilcarbamoilo, N,N-di-[(C1-6)alquil]carbamoilo, alcanoilamino C2-6, N-(C1-6)alquil-alcanoilamino C2-6, N-(C1-6)alquil]ureido, N'-(C1-6)alquil]ureido, 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, alcansulfonilamino C1-6, N-(C1-6)alquil-alcansulfonilamino C1-6 o entre un grupo de la formula: -X3-R9 en donde X3 es un enlace directo o se selecciona entre O y N(R10), en donde R10 es hidrogeno o alquilo C1-8, y R9 es halogeno-(C1-6)alquilo, hidroxi-(C1-6)alquilo, mercapto-(1-6)alquilo, alcoxi C1-6-alquilo C1-6, alquiltio C1-6-alquilo C1-6, alquilsulfinil C1-6-alquilo C1-6, alquilsulfonil C1-6-alquilo C1-6, ciano-(C1-6)alquilo, amino-(C1-6)alquilo, alquilamino C1-6-alquilo C1-6, di-[(C1- 6)alquil]amino-alquilo C1-6, alcanoilamino C2-6-alquilo C1-6, N-(C1-6)alquil-(C2-6)alcanoilamino-(C1-6)alquilo, alcoxicarbonilamino C1-6-alquilo C1-6, ureido-(C1-6)alquilo, N-(C1-6)alquilureido-alquilo C1-6, N'-(C1-6)alquilureido-alquilo C1-6, N',N'- di-[(C1-6)alquil]ureido-alquilo C1-6, N,N'-di-[(C1-6)alquil]ureido, o N,N',N'-tri-[(C1-6)alquil]ureido-alquilo C1-6, 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 hidrogeno o alquilo C1-8, y Q2 es arilo, aril-(C1-6)alquilo, heteroarilo, heteroaril-(C1-6)alquilo, heterociclilo o heterociclil-(C1-6)alquilo que lleva opcionalmente 1 o 2 sustituyentes, que pueden ser iguales o diferentes, seleccionados entre halogeno, hidroxi, alquilo C1-8 y alcoxi C1-6, y en donde cualquier grupo arilo, heteroarilo o heterociclilo dentro de un sustituyente en R1 lleva opcionalmente un grupo alquilendioxi C1-3, y en donde cualquier heterociclilo dentro de un sustituyente R1 lleva opcionalmente 1 o 2 sustituyentes oxo o tioxo, y en donde cualquier CH, CH2 o CH3 dentro de un sustituyente R1 lleva opcionalmente en cada uno de dichos grupos CH, CH2 o CH3 uno o más sustituyentes halogeno o alquilo C1-8 y/o un sustituyente seleccionado entre hidroxi, mercapto, amino, ciano, carboxi, carbamoilo, ureido, alcoxi C1-6, alquiltio C1-6, alquilsulfinilo C1-6, alquilsulfonilo C1-6, alquilamino C1-6, di-[(C1-6)alquil]amino, alcoxicarbonilo C1-6, N-(C1- 6)alquilcarbamoilo, N,N-di-[(C1-6)alquil]carbamoilo, alcanoilo C2-6, alcanoiloxi C2-6, alcanoilamino C2-6, N-(C1-6)alquil-alcanoilamino C2-6, N-(C1-6)alquilureido, N'-(C1-6)alquil]ureido, 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, alcansulfonilamino C1-6 y N-(C1-6)alquil-alcansulfonilamino C1-6, y en donde los átomos de carbono adyacentes en cualquier cadena alquileno C2-6 dentro de un sustituyente R1 se separan opcionalmente 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 hidrogeno o alquilo C1- 8, o, cuando el grupo insertado es N(R12), R12 también puede ser alcanoilo C2-6, q es 0, 1 o 2; cada grupo R2, que pueden ser iguales o diferentes, se selecciona entre halogeno, trifluorometilo, ciano, carboxi, hidroxi, amino, carbamoilo, alquilo C1- 8, alquenilo C2-8, alquinilo C2-8, alcoxi C1-6, alquilamino C1-6, di-[(C1-6 alquil]amino, N-(C1-6)alquilcarbamoilo, N,N-di-[(C1-6)alquil]carbamoilo, halogeno-(C1-6)alquilo, hidroxi-(C1-6)alquilo, alcoxi C1-6-alquilo C1-6, ciano-(C1-6)alquilo, carboxi-(C1-6)alquilo, alcoxicarbonil(C1-6)-alquilo C1-6, amino-(C1-6)alquilo, alquilamino C1-6-alquilo C1-6, di-[(C1-6)alquil]amino-alquilo C1-6, carbamoil-(C1-6)alquilo, N-(C1-6)alquilcarbamoil-alquilo C1-6, N,N-di-[(C1-6)alquil]carbamoil-(C1- 6)alquilo, alcanoilamino C2-6-alquilo C1-6 y N-(C1-6)alquil-(C2-6)alcanoilamino-(C1-6)alquilo; R3 es H, alquilo C1-8, alquenilo C2-8 o alquinilo C2-8, R4 es H, alquilo C1-8, alquenilo C2-8, alquinilo C2-8, halogeno-(C1-6)alquilo, hidroxi-(C1- 6)alquilo, alcoxi C1-6-alquilo C1-6, ciano-(C1-6)alquilo, carboxi-(C1-6)alquilo, amino-(C1-6)alquilo, alquilamino C1-6-alquilo C1-6, di-[(C1-6)alquil]amino-alquilo C1-6, carbamoil-(C1-6)alquilo, N-(C1-6)alquilcarbamoil-alquilo C1-6, N,N-di-[(C1- 6)alquil]carbamoil-alquilo C1-6, alcoxicarbonil C1-6-alquilo C1-6, alcanoilamino C2-6-alquilo C1-6, o N-(C1-6)alquil-(C2-6)alcanoilamino-(C1-6)alquilo, o R3 y R4 junto con el átomo de carbono al cual están unidos forman un grupo cicloalquilo C3-8; R5 es hidrogeno, alquilo C1-8, alquenilo C2-8 o alquinilo C2-8 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 hidrogeno o alquilo C1-8, y R13 es halogeno-(C1-6)alquilo, hidroxi- (C1-6)alquilo, alcoxi C1-6-alquilo C1-6 o ciano-(C1-6)alquilo; el Anillo A es un anillo arilo monocíclico de 6 miembros o bicíclico de 10 miembros o un anillo heteroarilo monocíclico de 5 o 6 miembros o bicíclico de 9 o 10 miembros con hasta tres heteroátomos en el anillo seleccionados entre oxígeno, nitrogeno y azufre; r es 0, 1, 2 o3;y cada grupo R6, que pueden ser iguales o diferentes, se selecciona entre halogeno, trifluorometilo, ciano, hidroxi, mercapto, amino, carboxi, carbamoilo, sulfamoilo, ureido, alquilo C1-8, alquenilo C2-8, alquinilo C2-8, alcoxi C1-6, alquiltio C1-6, alquilsulfinilo C1-6, alquilsulfonilo C1-6, alquilamino C1-6, di-[(C1-6 alquil]amino, alcoxicarbonilo C1-6, alcanoilo C2-6, alcanoiloxi C2-6, N-(C1- 6)alquilcarbamoilo, N,N-di-[(C1-6)alquil]carbamoilo, alcanoilamino C2-6, N-(C1-6)alquil-alcanoilamino C2-6, N-(C1-6)alquilureido, N',N'-di-[(C1-6)alquil]ureido, N-(C1-6)alquilsulfamoilo, N,N-di-[(C1-6)alquil]sulfamoilo, alcansulfonilamino C1-6 y N- (C1-6)alquil-(C1-6)alcansulfonilamino, o entre un grupo de la formula: -X6-R15en donde X6 es un enlace directo o se selecciona entre O y N(R16), en donde R16 es hidrogeno o alquilo C1-8, y R15 es halogeno-(C1-6)alquilo, hidroxi-(C1-6)alquilo, mercapto-(C1-6)alquilo, alcoxi C1-6-alquilo C1-6, alquiltio C1-6-alquilo C1-6, alquilsulfinil-C1-6-alquilo C1-6, alquilsulfonil C1-6-alquilo C1-6, ciano-(C1-6)alquilo, amino-(C1-6)alquilo, alquilamino C1-6-alquilo C1-6, di-[(C1-6)alquil]amino-(C1- 6)alquilo, alcanoilamino C2-6-alquilo C1-6, N-(C1-6)alquil-(C2-6)alcanoilamino-(C1-6)alquilo, carboxi-(C1-6)alquilo, alcoxicarbonil C1-6-alquilo C1-6, carbamoil-(C1-6)alquilo, N-(C1-6)alquilcarbamoil-(C1-6)alquilo, N,N-di-[(C1-6)alquil]carbamoil-(C1- 6)alquilo, sulfamoil-(C1-6)alquilo, N-(C1-6)alquilsulfamoil-(C1-6)alquilo, N,N-di-[(C1-6)alquil]sulfamoil-(C1-6)alquilo, ureido-(C1-6)alquilo, N-(C1-6)alquilureido-(C1-6)alquilo, N'-(C1-6)alquilureido-(C1-6)alquilo, N',N'-di-[(C1-6)alquil]ureido-(C1- 6)alquilo, N,N'-di-[(C1-6)alquil]ureido-(C1-6)alquilo, N,N',N'-tri-[(C1-6)alquil]ureido-(C1-6)alquilo, alcansulfonilamino C1-6-alquilo C1-6 o N-(C1-6)alquil-(C1-6)alcansulfonilamino-(C1-6)alquilo, o entre un grupo de la formula: -X7-Q3 en donde X7 es un enlace directo o se selecciona entre O, S, SO, SO2, N(R17), CO, CH(OR17), CON(R17), N(R17)CO, N(R17)CON(R17), SO2N(R17), N(R17)SO2, C(R17)2O, C(R17)2S y C(R17)2N(R17), en donde cada R17 es hidrogeno o alquilo C1-8, y Q3 es arilo, aril-(C1- 6)alquilo, cicloalquilo C3-8, cicloalquil C3-8-alquilo C1-6, cicloalquenilo C3-8, cicloalquenil C3-8-alquilo C1-6, heteroarilo, heteroaril-(C1-6)alquilo, heterociclilo o heterociclil-(C1-6)alquilo, o dos grupos R6 forman juntos un grupo bivalente que abarca posiciones adyacentes en el Anillo A seleccionado entre OC(R18)2O, OC(R18)2C(R18)2O, OC(R18)2C(R18)2, C(R18)2OC(R18)2, C(R18)2C(R18)2C(R18)2, C(R18)2C(R18)2C(R18)2C(R18)2, OC(R18)2N(R19), N(R19)C(R18)2N(R19), N(R19)C(R18)2C(R18)2, N(R19)C(R18)2C(R18)2C(R18)2, o C(R18)2C(R18)2N(R19), C(R18)2N(R19)C(R18)2, CO.N(R18)C(R18)2, N(R18)CO.C(R18)2, N(R19)C(R18)2CO, CO.N(R18)CO, N(R19)N(R18)CO, N(R18)CO.N(R18), O.CO.N(R18), O.CO.C(R18)2 y CO.OC(R18)2 en donde cada R18 es hidrogeno, alquilo C1-8, alquenilo C2-8 o alquinilo C2-8, y en donde R19 es hidrogeno, alquilo C1-8, alquenilo C2-8, alquinilo C2-8 o alcanoilo C2-6, y en d
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US20090076074A1 (en) 2009-03-19
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US7973164B2 (en) 2011-07-05
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CA2642973A1 (en) 2007-09-07
UY30183A1 (es) 2007-10-31
WO2007099326A1 (en) 2007-09-07
AU2007220285A1 (en) 2007-09-07
JP2009529002A (ja) 2009-08-13
RU2454411C2 (ru) 2012-06-27
BRPI0708431A2 (pt) 2011-05-31
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AU2007220285B2 (en) 2011-05-19

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