AR066036A2 - Derivados de hidroxi-1- azobenceno, composiciones farmaceuticas que los comprenden, uso de dichos compuestos en la fabricacion de medicamentos, proceso para preparar dichas composiciones, proceso para preprar dichos compuestos, metodo in vitro o ex vivo para aumentar la estimulacion de la maduracion - Google Patents

Derivados de hidroxi-1- azobenceno, composiciones farmaceuticas que los comprenden, uso de dichos compuestos en la fabricacion de medicamentos, proceso para preparar dichas composiciones, proceso para preprar dichos compuestos, metodo in vitro o ex vivo para aumentar la estimulacion de la maduracion

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Publication number
AR066036A2
AR066036A2 ARP080101867A ARP080101867A AR066036A2 AR 066036 A2 AR066036 A2 AR 066036A2 AR P080101867 A ARP080101867 A AR P080101867A AR P080101867 A ARP080101867 A AR P080101867A AR 066036 A2 AR066036 A2 AR 066036A2
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AR
Argentina
Prior art keywords
chloro
hydroxy
carboxylic acid
acid
amino
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ARP080101867A
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Smithkline Beecham Corp
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Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp
Publication of AR066036A2 publication Critical patent/AR066036A2/es

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Abstract

Un derivado de hidroxi-1-azobenceno y sus sales, hidratos, solvatos y ésteres farmacéuticamente aceptables, donde dicho derivado está representado por la formula (1), en la que R, R1, R2 y R3 se seleccionan cada uno independientemente de hidrogeno, alquilo C1-6, -(CH2)pOR4, -C(O)OR4, formilo, nitro, ciano, halogeno, arilo, arilo sustituido, alquilo sustituido, -S(O)nR4, cicloalquilo, -NR5R6, -OH protegido, -CONR5R6, ácido fosfonico, ácido sulfonico, ácido fosfínico, -SO2NR5R6, y un sustituyente metilen-heterocíclico como se representa por la formula (2), en la que, p es 0-6, n es 0-2; V, W, X y Z se seleccionan cada uno independientemente de O, S y NR16, en el que R16 se selecciona de: hidrogeno, alquilo, cicloalquilo, arilo C1-12, alquilo sustituido, cicloalquilo sustituido y arilo C1-12 sustituido; R4 se selecciona de: hidrogeno, alquilo, cicloalquilo, arilo C1-12, alquilo sustituido, cicloalquilo sustituido y arilo C1-12 sustituido; y R5 y R6 se seleccionan cada uno independientemente de hidrogeno, alquilo, alquilo sustituido, cicloalquilo C3-6, y arilo, o R5 y R6 tomados junto con el átomo de nitrogeno al que están unidos representan un anillo saturado de 5 a 6 miembros que contiene hasta otro heteroátomo seleccionado de oxígeno y nitrogeno; m es 0-6; y AR es un anillo aromático cíclico o policíclico que contiene de 3 a 16 átomos de carbono y que contiene uno o más heteroátomos, con la condicion de que, cuando el numero de átomos de carbono es 3, el anillo aromático contiene al menos dos heteroátomos, y cuando el numero de átomos de carbono es 4 el anillo aromático contiene al menos un heteroátomo, y opcionalmente sustituido con uno o más sustituyentes seleccionados del grupo que consta de: alquilo, alquilo sustituido, arilo, cicloalquilo sustituido, arilo sustituido, ariloxi, oxo, hidroxi, alcoxi, cicloalquilo, aciloxi, amino, N-acilamino, nitro, ciano, halogeno, -C(O)OR4, -C(O)NR10R11, -S(O)2NR10R11, -S(O)nR4 y -OH protegido, en el que n es 0-2; R4 es hidrogeno, alquilo, cicloalquilo, arilo C1-12, alquilo sustituido, cicloalquilo sustituido y arilo C1-12 sustituido; y R10 y R11 son independientemente hidrogeno, cicloalquilo, arilo C1-12, cicloalquilo sustituido, arilo C1-12 sustituido, alquilo o alquilo sustituido con uno o más sustituyentes seleccionados del grupo que consta de: alcoxi, aciloxi, ariloxi, amino, N-acilamino, oxo, hidroxi, -C(O)OR4, -S(O)nR4, -C(O)NR4R4, -S(O)2NR4R4, nitro, ciano, cicloalquilo, cicloalquilo sustituido, halogeno, arilo, arilo sustituido y -OH protegido, o R10 y R11, tomados junto con el átomo de nitrogeno al que están unidos, representan un anillo saturado de 5 a 6 miembros que contiene hasta otro heteroátomo seleccionado de oxigeno y nitrogeno, en el que R4 es como se describe anteriormente y n es 0-2; con la condicion de que al menos uno de R, R1, R2 y R3 sea un grupo arilo sustituido o un sustituyente metilen-heterocíclico como se representa en la formula (2), y con la condicion de que no sea ninguno de los siguientes compuestos: ácido 3'-{N-[1-(3,4-dimetilfenil)-3-metil-5-oxo-1,5-dihidropirazol-4-iliden]hidrazino}-2'-hidroxibifenil-3-carboxílico; ácido 4'-{N'-[1-(3,4-dimetilfenil)-3-metil-5-oxo-1,5-dihidropirazol-4-iliden]hidrazino}-3'-hidroxibifenil-4-carboxílico; 3-{N'-[1-(3,4-dimetilfenil)-3-metil-5-oxo-1,5-dihidropirazol-4-iliden]hidrazino}-2-hidroxi-3'-(tetrazol-5-il)bifenilo; ácido 3'-{N'-[1-(4-ter-butilfenil)-3-metil-5-oxo-1,5-dihidropirazol-4-iliden]hidrazino}-2'-hidroxibifenil-3-carboxílico, ácido 3-aza-3'-{N'-[1-(4-ter-butilfenil)-3-metil-5-oxo-1,5-dihidropirazol-4-iliden]-hidrazino}-2'-hidroxibifenil-5-carboxílico. También se dan a conocer: composiciones farmacéuticas que los comprenden, uso de dichos compuestos en la fabricacion de medicamentos, proceso para preparar dichas composiciones, proceso para preparar dichos compuestos, método in vitro o ex vivo para aumentar la estimulacion de la maduracion de megacariocitos y/o produccion de trombocitos, método in vitro o ex vivo para aumentar la supervivencia y/o proliferacion de células madre, células de médula osea, células de sangre del cordon umbilical, células de sangre periférica u otros tipos de células que expresan el receptor de tpo en cultivo, método in vitro o ex vivo para aumentar la estimulacion de la produccion de neutrofilos, e intermediario usado en la preparacion de dichos compuestos. Reivindicacion 21: Un intermediario usado en la preparacion de compuestos de la reivindicacion 1, caracterizado porque está seleccionado de: ácido 4'-amino-3'-hidroxibifenil-4-carboxílico, ácido 4'-amino-3'-hidroxibifenil-3-carboxílico; ácido 3'-amino-2'-hidroxibifenil-3-carboxílico; ácido 3'-amino-2'-hidroxibifenil-4-carboxílico; 3-amino-2-hidroxi-3'-(1H-tetrazol-5-il)bifenilo; 3-amino-2-hidroxi-4'-(1H-tetrazol-5-il)bifenilo; 3-amino-5-cloro-2-hidroxi-4'-(1H-tetrazol-5-il)bifenilo; ácido 6-(3-amino-2-hidroxifenil)piridin-2-carboxílico; ácido 6-(3-amino-5-cloro-2-hidroxifenil)piridin-2-carboxílico; ácido 6-(3-amino-2-hidroxi-5-metiIfenil)piridin-2-carboxílico; ácido 5-(3-amino-2-hidroxifenil)nicotinico; ácido 5-(3-amino-2-hidroxi-5-metilfenil)nicotínico; ácido 2-(3-amino-2-hidroxifenil)isonicotínico; ácido 3'-amino-2'-hidroxi-5'-metilbifenil-3-carboxílico; ácido 3'-amino-5'-fluor-2'-hidroxibifenil-3-carboxílico, ácido 3'-amino-5'-cloro-2'-hidroxibifenil-3-carboxílico; ácido 3'-amino-2'-hidroxibifenil-3,5-carboxílico, N-[1-(3'-amino-2'-hidroxibifenil-3-il)metanoil]metanosulfonamida; N-(3'-amino-2'-hidroxibifenil-3-iI)-1,1,1-trifluorometanosulfonamida; ácido (3'-amino-2'-hidroxibifenil-3-il)fosfonico; ácido 3'-amino-2'-hidroxibifenil-3,4-dicarboxílico; ácido 3'-amino-4,2'-dihidroxibifenil-3-carboxílico; ácido 3'-amino-2'-hidroxibifenil-3-sulfonico; ácido 3'-hidroxi-4'-nitrobifenil-4-carboxílico; ácido 3'-hidroxi-4'-nitrobifenil-3-carboxílico; ácido 2'-hidroxi-3'-nitrobifenil-3-carboxílico; ácido 2'-hidroxi-3'-nitrobifenil-4-carboxílico; 5-cloro-2-hidroxi-3-nitro-3'-(1H-tetrazol-5-iI)bifenilo, 5-cloro-2-hidroxi-3-nitro-4'-(1H-tetrazol-5-il)bifenilo, ácido 6-(5-cloro-2-hidroxi-3-nitrofenil)piridin-2-carboxílico; ácido 6-(2-hidroxi-5-metil-3-nitrofenil)piridin-2-carboxílico; ácido 5-(5-cloro-2-hidroxi-3-nitrofenil)nicotinico; ácido 5-(5-cloro-2-hidroxi-5-metil-3-nitrofenil)nicotinico; ácido 2-(5-cloro-2-hidroxi-3-nitrofenil)isonicotínico; ácido 5'-cloro-2'-hidroxi-3'-nitrobifenil-3-carboxílico; ácido 5'-cloro-2'-hidroxi-3'-nitrobifenil-3,5-dicarboxílico; N-[1-(5'-cloro-2'-hidroxi-3'-nitrobifenil-3-il)metanoil]metanosulfonamida; 1,1,1-trifluoro-N-(2'-hidroxi-3'-nitrobifenil-3-il)metanosulfonamida; ácido (5'-cloro-2'-hidroxi-3'-nitrobifenil-3-il)fosfonico; ácido 5'-cloro-2'-hidroxi-3'-nitrobifenil-3,4-dicarboxílico; ácido 5'-cloro-4,2'-dihidroxi-3'-nitrobifenil-3-carboxílico; ácido 5'-cloro-2'-hidroxi-3'-nitrobifenil-3-sulfonico; ácido 2'-metoxi-3'-nitrobifenil-3-carboxílico; ácido 2'-metoxi-3'-nitrobifenil-4-carboxílico; 5-cloro-2-hidroxi-3'-(1H-tetrazol-5-iI)bifenilo; 5-cloro-2-hidroxi-4'-(1H-tetrazol-5-il)bifenilo; ácido 6-(5-cloro-2-hidroxifenil)piridin-2-carboxílico; ácido 6-(2-hidroxi-5-metilfenil)piridin-2-carboxílico, ácido 6-(2-hidroxi-5-metilfenil)piridin-2-carboxílico, ácido 5-(5-cloro-2-hidroxi-5-metilfenil)nicotínico; ácido 2-(5-cloro-2-hidroxifenil)isonicotínico; ácido 5'-cloro-2'-hidroxibifenil-3-carboxílico; ácido 5'-cloro-2'-hidroxibifenil-3,5-dicarboxílico; N-[1-(5'-cloro-2'-hidroxibifenil-3-iI)metanoil]metanosulfonamida; 3'-amino-3-nitrobifenil-2-ol; ácido (5'-cloro-2'-hidroxibifenil-3-il)fosfonico; ácido 5'-cloro-2'-hidroxibifenil-3,4-dicarboxílico; ácido 5'-cloro-4,2'-dihidroxibifenil-3-carboxílico; ácido 5'cloro-2'-hidroxibifenil-3-sulfonico; 5-cloro-2-metoxi-3'-(1H-tetrazol-5-iI)bifenilo; 5-cloro-2-metoxi-4'-(1H-tetrazol-5-il)bifenilo; ácido 6-(5-cloro-2-metoxifenil)piridin-2-carboxílico; ácido 6-(2-metoxi-5-metilfenil)piridin-2-carboxílico; ácido 6-(2-metoxi-5-metilfenil)piridin-2-carboxílico; ácido 5-(5-cloro-2-metoxi-5-metilfenil)nicotínico; ácido 2-(5-cloro-2-metoxifenil)isonicotínico; ácido 5'-cloro-2'-metoxibifenil-3-carboxílico; ácido 5'-cloro-2'-metoxibifenil-3,5-dicarboxílico; N-[1-(5'-cloro-2'-metoxibifenil-3-il)metanoil]metanosulfonamida; N-(2'-metoxi-3'-nitrofenil-3-il)acetamida; ácido (5'-cloro-2'-metoxibifenil-3-il)fosfonico; ácido 5'-cloro-2'-metoxibifenil-3,4-dicarboxílico; ácido 5'-cloro-4-hidroxi-2'-metoxibifenil-3-carboxílico; y ácido 5'-cloro-2'-metoxibifenil-3-sulfonico.
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