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AR061132A1 - Compuestos de fenilalanina, alanina y tirosina, un proceso para su preparacion, una composicion farmaceutica que los comprende y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por la inhibicion de la integrina alfa5beta1. - Google Patents

Compuestos de fenilalanina, alanina y tirosina, un proceso para su preparacion, una composicion farmaceutica que los comprende y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por la inhibicion de la integrina alfa5beta1.

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Publication number
AR061132A1
AR061132A1 ARP070102260A ARP070102260A AR061132A1 AR 061132 A1 AR061132 A1 AR 061132A1 AR P070102260 A ARP070102260 A AR P070102260A AR P070102260 A ARP070102260 A AR P070102260A AR 061132 A1 AR061132 A1 AR 061132A1
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AR
Argentina
Prior art keywords
alkyl
group
heterocyclyl
optionally
heteroaryl
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Application number
ARP070102260A
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English (en)
Inventor
Jean-Claud Arnould
Benedicte Delouvrie
Richard Ducray
Van Der Brempt Christine Marie Paul Lambert
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Astrazeneca Ab
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Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of AR061132A1 publication Critical patent/AR061132A1/es

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    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
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    • 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
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    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical
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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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  • Quinoline Compounds (AREA)
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  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Compuestos inhibidores de la funcion a5b1, procesos para su preparacion, composiciones farmacéuticas que los contienen como ingrediente activo, su uso como medicamento y su uso en la elaboracion de medicamentos para usar en el tratamiento en animales de sangre caliente, tal como humanos, de enfermedades que tienen un componente significativo de angiogénesis o vascular, tal como para el tratamiento de tumores solidos. También se relaciona con antagonistas de a5b1 que también presentan un perfil o perfiles de selectividad apropiado/s contra otras integrinas. Reivindicacion 1: Un compuesto caracterizado porque responde a la formula 1: en donde: Xa se selecciona entre oxigeno o azufre; R1 se selecciona entre bromo, cloro, alquilo C1- 3, ciclopropilo, ciclobutilo, ciclopentilo, ciclopropilmetilo, ciclobutilmetilo, ciclopentilmetilo y halo-alquilo C1-3; R2 y cada R3, que pueden ser iguales o diferentes, se seleccionan entre hidrogeno, halo, trifluorometilo, ciano, isociano, nitro, hidroxi, mercapto, amino, formilo, carboxi, carbamoilo, sulfamoilo, 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-[(C1- 6)alquil]amino, alcoxicarbonilo C1-6, N-alquilcarbamoilo C1-6, N,N-di-[(C1-6)alquil]carbamoilo, alcanoilo 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, NN-di-[(C1-6)alquil]sulfamoilo, alcansulfonilamino C1-6 y N-aIquil C1-6-alcansulfonilamino C1-6, o entre un grupo de la formula: Q1-X1 en donde X1 es un enlace directo o se selecciona entre O, S, SO, SO2, N(R7), C(O), CH(OR7), C(O)N(R7), N(R7)C(O), SO2N(R7), N(R7)SO2, OC(R7)2, SC(R7)2 y N(R7)C(R7)2, en donde R7 es hidrogeno o alquilo C1-6, y Q1 es arilo, aril-alquilo C1-6, cicloalquilo C3-7, cicloaiquil C3-7- alquilo C1-6, cicloalquenilo C3-7, cicloalquenil C3-7-alquilo C1-6, heteroarilo, heteroaril-alquilo C1-6, heterociclilo o heterociclil-alquilo C1-6, y en donde R2 y algun R3 en forma independiente entre sí tienen opcionalmente en el carbono uno o más grupos R8, y en donde si algun grupo heteroarilo o heterociclilo dentro de R2 y algun R3 contiene una porcion -NH-, el nitrogeno de dicha porcion tiene opcionalmente un grupo seleccionado entre R9, y en donde cualquier grupo heterociclilo dentro de R2 y algun R3 tiene opcionalmente 1 o 2 sustituyentes oxo o tioxo; o R2 y un sustituyente R3 forman opcionalmente un grupo alquilendioxi C1-3; o dos sustituyentes R3 forman opcionalmente un grupo alquilendioxi C1-3; m es 0, 1, 2 o 3; R4 se selecciona entre hidrogeno, alquilo C1-6, heterociclilo, heterociclil-alquilo C1-6, arilo, aril-alquilo C1-6, heteroarilo y heteroaril-alquilo C1-6, que opcionalmente tiene en el carbono uno o más R21 sustituyentes, que pueden ser iguales o diferentes, y en donde si algun grupo heteroarilo o heterociclilo dentro de R4 contiene una porcion -NH- el nitrogeno de dicha porcion tiene opcionalmente un grupo seleccionado entre R22, y en donde si algun grupo heterociclilo dentro de R4 tiene opcionalmente 1 o 2 sustituyentes oxo o tioxo; el anillo A se selecciona entre fenilo, piridinilo y tiofenilo; n es 0, 1, 2, 3 o 4, con la salvedad de que cuando el anillo A es piridinilo, n es 0, 1, 2 o 3 y que cuando el anillo A es tiofenilo, n es 0, 1 o 2; cada R5, que pueden ser iguales o diferentes, se seleccionan entre halo, trifluorometilo, ciano, isociano, nitro, hidroxi, mercapto, amino, formilo, carboxi, carbamoilo, sulfamoilo, 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-[(C1-6)alquil]amino, alcoxicarbonilo C1-6, N-alquilcarbamoilo C1-6, N,N-di-[(C1-6)alquil]carbamoilo, alcanoilo 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-[(C1-6)alquil]sulfamoilo, alcansulfonilamino C1-6 y N-alquil C1-6-alcansulfonilamino C1-6, o entre un grupo de la formula: Q5-X7-, en donde X7 es un enlace directo o se selecciona entre O, S, SO, SO2, N(R23), C(O), CH(OR23), C(O)N(R23), N(R23)C(O), SO2N(R23), N(R23)SO2, OC(R23)2, SC(R23)2 y N(R23)C(R23)2, en donde R23 es hidrogeno o alquilo C1-6, y Q5 es arilo, aril-alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-6, cicloalquenilo C3-7, cicloalquenil C3-7-alquilo C1-6, heteroarilo, heteroaril-alquilo C1-6, heterociclilo o heterociclil-alquilo C1-6, y en donde R5 opcionalmente tiene en el carbono uno o más grupos R24, y en donde si algun grupo heteroarilo o heterociclilo cualquiera dentro de R5 contiene una porcion -NH-, el nitrogeno de dicha porcion tiene opcionalmente un grupo seleccionado entre R25, y en donde cualquier grupo heterociclilo dentro de R5 tiene opcionalmente 1 o 2 sustituyentes oxo o tioxo; o dos sustituyentes R5 forman opcionalmente un grupo alquilendioxi C1-3; X se selecciona entre un enlace directo, N(R26), O, S, SO, SO2, C(O), CH(OR26), C(O)N(R26), N(R26)C(O), SO2N(R26), N(R26)SO2, alquileno C1-6, CH=CH y C:::C, en donde R26 es hidrogeno, alquilo C1-6 o cicloalquilo C3-7; Y se selecciona entre alquileno C1-6, cicloalquileno C3-7, cicloalquenileno C3-7 y heterociclilo, Z se selecciona entre un enlace directo, N(R26), O, S, SO, SO2, C(O), CH(OR26), SO2N(R26), N(R26)SO2, alquileno C1-6, CH=CH y C:::C, en donde R26 es hidrogeno, alquilo C1-6 o cicloalquilo C3-7; y en donde átomos de carbono adyacentes en cualquier cadena alquileno C2-6, dentro de un sustituyente X, Y o Z están separados opcionalmente por la insercion en la cadena de un grupo seleccionado entre O, S, SO, SO2, N(R27), C(O), CH(OR27), C(O)N(R27), N(R27)C(O), SO2N(R27), N(R27)SO2, CH=CH y C:::C en donde R27 es hidrogeno, alquilo C1-6 o cicloalquilo C3-7; y en donde cualquier X, Y o Z opcionalmente tiene en el carbono uno o más sustituyentes R28, y en donde si algun grupo heterociclilo dentro de Y contiene una porcion -NH-, el nitrogeno de dicha porcion tiene opcionalmente un grupo seleccionado entre R29; con la salvedad de que cuando X es un enlace directo o O e Y es un heterociclilo que contiene un heteroátomo de nitrogeno, entonces el grupo R6-Z- está unido a un átomo de carbono en el heterociclilo que contiene el heteroátomo de nitrogeno; R6 es heteroarilo, en donde el heteroarilo contiene al menos un átomo de nitrogeno, y en donde R6 opcionalmente tiene en el carbono uno o más sustituyentes R31, y en donde si R6 contiene una porcion -NH-, el nitrogeno de dicha porcion tiene opcionalmente un grupo seleccionado entre R35; R8, R21, R24 y R28 se selecciona entre halo, trifluorometilo, ciano, nitro, hidroxi, amino, carboxi, carbamoilo, sulfamoilo, 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-[(C1-6)alquil]amino, alcoxicarbonilo C1-6, N- alquilcarbamoilo C1-6, N,N-di-[(C1-6)alquil]carbamoilo, alcanoilo C2-6, alcanoiloxi C2-6, alcanoilamino C2-6, N-alquil C1-6-alcanoilamino C2-6, N-alquilsulfamoilo C1-6, N,N-di-[(C1-6)alquil]sulfamoilo, alcansulfonilamino C1-6 y N-alquil C1-6- alcansulfonilamino C1-6, o entre un grupo de la formula: -X2-R10 en donde X2 es un enlace directo o se selecciona entre O, C(O) y N(R11), en donde R11 es hidrogeno o alquilo C1-6, y R10 es halo-alquilo C1-6, hidroxi-alquilo C1-6, alcoxi C1-6-alquilo C1-6, ciano-alquilo C1-6, amino-alquilo C1-6, alquilamino C1-6-alquilo C1-6, di-[(C1-6)alquil]amino-alquilo C1-6, alcanoilamino C2-6-alquilo C1-6 y alcoxicarbonilamino C1-6-alquilo C1-6, o entre un grupo de la formula -X3-Q2 en donde X3 es un enlace directo o se selecciona entre O, S, SO, SO2, N(R12), C(O), CH(OR12), C(O)N(R12), N(R12)C(O), SO2N(R12), N(R12)SO2, OC(R12)2, SC(R12)2 y N(R12)C(R12)2, en donde R12 es hidrogeno o alquilo C1-6, y Q2 es arilo, aril-alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-6, cicloalquenilo C3-7, cicloalquenil C3-7-alquilo C1-6, heteroarilo, heteroaril-alquilo C1-6, heterociclilo o heterociclil-alquilo C1-6, y en donde R8, R21, R24 y R28 en forma independiente entre sí tienen opcionalmente en el carbono uno o más R13, y en donde si algun grupo heteroarilo o heterociclilo cualquiera dentro de R8, R21, R24 y R28 contiene una porcion -NH- el nitrogeno de dicha porcion tiene opcionalmente un grupo seleccionado entre R14, y en donde cualquier grupo heterociclilo dentro de un sustituyente sobre R8, R21, R24 y R28 en forma independiente entre si tiene opcionalmente 1 o 2 sustituyentes oxo o tioxo; R9, R22, R25 y R29 se selecciona cada uno en forma independiente entre ciano, hidroxi, carboxi, carbamoilo, sulfamoilo, alquilo C1-6, alquenilo C2-8, alquinilo C2-8, alquilsulfonilo C1-6, alcoxicarbonilo C1-6, N-alquilcarbamoilo C1-6, N,N-di-[(C1-6)alquil]carbamoilo, alcanoilo C2-6, N-alquilsulfamoilo C1-6 y NN-di-[(C1- 6)alquil]sulfamoilo, o entre un grupo de la formula: -X4-R15 en donde X4 es un enlace directo o se selecciona entre C(O), SO2, C(O)N(R16) y SO2N(R16), en donde R16 es hidrogeno o alquilo C1-6, y R15 es halo-alquilo C1-6, hidroxi-alquilo C1-6, alcoxi C1-6-alquilo C1-6, ciano-alquilo C1-6, amino-alquilo C1-6, alquilamino C1-6-alquilo C1-6, di-[(C1-6)alquil]amino-alquilo C1-6, alcanoilamino C2-6-alquilo C1-6 y alcoxicarbonilamino C1-6-alquilo C1-6, o entre un grupo de la formula -X5-Q3 en donde X5 es un enlace directo o se selecciona entre C(O), SO2, C(O)N(R17) y SO2N(R17), en donde R17 es hidrogeno o alquilo C1-6, y Q3 es arilo, aril-alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-6, cicloalquenilo C3-7, cicloalquenil C3-7- alquilo C1-6, heteroarilo, heteroaril-alquilo C1-6, heterociclilo o heterociclil-alquilo C1-6, y en donde R9, R22, R25 y R
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