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AR047894A1 - Derivados de tiofeno como inhibidores de la proteina tirosina fosfatasa 1b (ptpasa 1b); metodos para su preparacion, composiciones farmaceuticas que los contienen y su uso en el tratamiento de enfermedades mediadas por ptpasa 1b - Google Patents

Derivados de tiofeno como inhibidores de la proteina tirosina fosfatasa 1b (ptpasa 1b); metodos para su preparacion, composiciones farmaceuticas que los contienen y su uso en el tratamiento de enfermedades mediadas por ptpasa 1b

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AR047894A1
AR047894A1 ARP050100660A ARP050100660A AR047894A1 AR 047894 A1 AR047894 A1 AR 047894A1 AR P050100660 A ARP050100660 A AR P050100660A AR P050100660 A ARP050100660 A AR P050100660A AR 047894 A1 AR047894 A1 AR 047894A1
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alkyl
halogen
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Wyeth Corp
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Abstract

Las proteínas tirosina fosfatasas (PTPasas) tal como las PTP1B pueden jugar un rol en la regulacion de una amplia variedad de respuestas celulares tales como las senales de insulina. Los compuestos de tiofeno sustituidos tales como, por ejemplo, tiofenos 2-carboxilo, 3-carboximetoxi, 5-arilo sustituidos, pueden inhibir PTP1B y de esa manera inducir una sensitividad mayor a la insulina. Consecuentemente, la inhibicion de la PTP1B puede proporcionar un tratamiento recíproco para los desordenes mediados por las PTPasa, tal como las diabetes. Asimismo, estos compuestos se utilizan para preparar composiciones farmacéuticas. Reivindicacion 1: Un compuesto de la formula (1), caracterizado porque R1 es R5, OR5, C(O)OR5, C(O)R5, o C(O)NR5R6; R2 es R5; X es -O-alquilenoC1-3, -NR8-alquilenoC1-3, -S-alquilenoC1-3, -SO-alquilenoC1-3, -SO2-alquilenoC1-3, -alquilenoC1-4, -alquenilenoC2-4, o -alquinilenoC2-4, cualquiera de los grupos alquileno, alquenileno o alquinileno pueden estar opcionalmente sustituidos con uno o más halogeno, oxo, imido, CN, OCF3, OH, NH2, NO2, o Q; Y está ausente, -O-, o -NR6-; R3 es H, halogeno, CN, CF3, OCF3, alquilo C1-3, cicloalquilo C3-4, alcoxi C1-3, o arilo; R4 es A-B-E-D, en donde A está ausente o es arileno, heteroarileno, alquileno C1-6, alquenilo C2-6, o alquinilo C2-6, cada A puede estar opcionalmente sustituido con uno o más de alquilo C1-6, alquenilo C2-6, alquinilo C2-6, halogeno, CN, OCF3, OH, NH2, CHO, NO2, o Q, donde cualquiera de los grupos alquilo, alquenilo o alquinilo está opcionalmente sustituido con uno o más halogeno, oxo, CN, OCF3, OH, NH2, NO2, N3 o Q; cada A puede estar opcionalmente terminado con uno o más arileno, alquileno, o alquenileno; B está ausente o es -NR5- , -NR7-, -N(R5)CH2-, -N(R7)CH2-, -N(R9)-, -N(R9)C(O)-, -N(R9)C(O)C(R11)(R12)-, -N(R9)C(O)C(O)-, -N(R9)C(O)N(R10)-, -N(R9)SO2-, -N(R9)SO2C(R10)(R11)-, -N(R9)(R10)C(R11)(R12)-, -N(R9)C(R11)(R12)C(R13)(R14)-, -O-, -O-C(R11)(R12), -O- C(R11)(R12)C(R13)(R14)-, -C(R11)(R12)-O-, -C(R11)(R12)-O-C(R13)(R14)-, -C(R11)(R12)N(R9)-, -C(R11)(R12)N(R9)C(R13)(R14)-, -C(R11)(R12)S-, -C(R11)(R12)SC(R13)(R14)-, o -C(R11)(R12)SO2C(R13)(R14)-; E está ausente o es cicloalquileno C3-12, heterociclilo de 3- a 12- miembros, arileno, alquileno C1-12, alquenileno C2-12, o alquileno C2-12, donde E está opcionalmente sustituido con uno o más alquilo C1-3, alcoxi C1-3, halogeno, CN, OH, NH2, o NO2; D es uno o más H, halogeno, OH, NH2, CHO, CN, NO2, CF3, o Q; con la condicion que cuando A, B y E están ausentes, R1 es C(O)OH o C(O)OCH3, R2 es H, y R3 es H o cloro, D es diferente de H o cloro; y cuando A, B, y E están ausentes, R1 es C(O)OH o C(O)OCH3, R2 es H, y R3 es H o bromo, D es diferente de H o bromo; cada Q, es independientemente, -R5, -R7, -OR5, -OR7, -NR5R6, -NR5R7, -N+R5R6R8, S(O)nR5, o -S(O)nR7, y n es 0, 1, o 2; cada R5, R6 y R8, es independientemente, H, alquilo C1-12, alquenilo C2-12, alquinilo C2-12, cicloalquilo C3-12, alcoxiC1-12alquiloC1-12, cicloalquil alquiloC1-6, heterociclilo de 3- a 8- miembros, heterociclil alquiloC1-6, arilo, aril alquilC1-6, aril alquenilo C2-6, o aril alquinilo C2-6, cada R5, R6 y R8 puede estar opcionalmente sustituido con uno o más R9, -OR9, -OC(O)OR9, -C(O)R9, -C(O)OR9, -C(O)NR9R10, -SR9, -S(O)R9, -S(O)2R9,-NR9R10, -N+R9R10R11, -NR9C(O)R10, -NC(O)NR9R10, -NR9S(O)2R10, oxo, halogeno, CN, OCF3, CF3, OH, o NO2; R7 es -C(O)R5, -C(O)OR5, -C(O)NR5R6, - S(O)2R5, -S(O)R5, o -S(O)2N5R6; cada R9, R10, R11, R12, R13 y R14 son, independientemente, H, alquilo C1-12, alquenilo C2-12, alquinilo C2-12, cicloalquilo C3-12, arilo, o aril alquilo C1-12; cualquiera de alquilo, alquenilo, alquinilo, cicloalquilo, arilo, o grupos arilalquilo está opcionalmente sustituido con uno o más halogeno, oxo, CN, OCF3, OH, NH2, o NO2; o una sal de los mismos. Reivindicacion 58: Un método para sintetizar un compuesto de la formula (1) para la inhibicion de la PTPasa, caracterizado porque dicho método comprende el paso de alquilar un compuesto de la formula (2) para formar un compuesto de la formula (3), siendo el compuesto de formula (1), en donde R1 es R5, OR5, C(O)OR5, C(O)R5, o C(O)NR5R6; R2 es R5; X es -O-alquilenoC1-3, -NR8-alquilenoC1-3, -S-alquilenoC1-3, -SO-alquilenoC1-3, -SO2-alquilenoC1-3, -alquilenoC1-4, -alquenilenoC2-4, -alquinilenoC2-4; en donde cualquiera de los grupos alquileno, alquenileno o alquinileno está opcionalmente sustituidos con uno o más halogeno, oxo, imido, CN, OCF3, OH, NH2, NO2, o Q; Y está ausente, -O-, o -NR6-; R3 es H, halogeno, CN, CF3, OCF3, alquilo C1-3, cicloalquilo C3-4, alcoxi C1-3, o arilo; R4 es A-B-E-D, en donde A está ausente o es arileno, heteroarileno, alquileno C1-6, alquenilo C2-6, o alquinilo C2-6, siendo cada A opcionalmente sustituido con uno o más de alquilo C1-6, alquenilo C2-6, alquinilo C2-6, halogeno, CN, OCF3, OH, NH2, CHO, NO2, o Q; en donde cualquiera de alquilo, alquenilo o alquinilo está opcionalmente sustituido con uno o más halogeno, oxo, CN, OCF3, OH, NH2, NO2, N3 o Q; y cada A siendo opcionalmente terminado con uno o más arileno, alquileno, o alquenileno; B está ausente o es -NR5-, -NR7-, -N(R5)CH2-, - N(R7)CH2-, -N(R9)-, -N(R9)C(O)-, -N(R9)C(O)C(R11)(R12)-, -N(R9)C(O)C(O)-, -N(R9)C(O)N(R10)-, -N(R9)SO2-, -N(R9)SO2C(R10)(R11)-, -N(R9)(R10)C(R11)(R12)-, -N(R9)C(R11)(R12)C(R13)(R14)-, -O-, -O-C(R11)(R12), -O-C(R11)(R12)C(R13)(R14)-, -C(R11)(R12)-O-, -C(R11)(R12)-O-C(R13)(R14)-, -C(R11)(R12)N(R9)-, -C(R11)(R12)N(R9)C(R13)(R14)-, -C(R11)(R12)S-, -C(R11)(R12)SC(R13)(R14)-, o -C(R11)(R12)SO2C(R13)(R14)-; E está ausente o es cicloalquileno C3-12, heterociclilo de 3- a 12- miembros, arileno, alquileno C1-12, alquenileno C2-12, o alquileno C2-12, en donde cada E está opcionalmente sustituido con uno o más alquilo C1-3, alcoxi C1-3, halogeno, CN, OH, NH2, o NO2; D es uno o más H, halogeno, OH, NH2, CHO, CN, NO2, CF3, o Q; cada Q, es independientemente -R5, -R7, -OR5, -OR7, -NR5R6, -NR5R7, -N+R5R6R8, S(O)nR5, o -S(O)nR7, donde n es 0, 1, o 2; cada R5, R6 y R8, es independientemente, H, alquilo C1-12, alquenilo C2-12, alquinilo C2-12, cicloalquilo C3-12, alcoxiC1-12alquiloC1-12, cicloalquil alquiloC1-6, heterociclilo de 3- a 8- miembros, heterociclil alquiloC1-6, arilo, aril alquilC1-6, aril alquenilo C2-6, o aril alquinilo C2-6, en donde cada R5, R6 y R8 está opcionalmente sustituido con uno o más R9, -OR9, -OC(O)OR9, - C(O)R9, -C(O)OR9, -C(O)NR9R10, -SR9, -S(O)R9, -S(O)2R9,-NR9R10, -N+R9R10R11, -NR9C(O)R10, -NC(O)NR9R10, -NR9S(O)2R10, oxo, halogeno, CN, OCF3, CF3, OH, o NO2; R7 es -C(O)R5, -C(O)OR5, -C(O)NR5R6, -S(O)2R5, -S(O)R5, o -S(O)2N5R6; y cada R9, R10, R11, R12, R13 y R14 son, independientemente, H, alquilo C1-12, alquenilo C2-12, alquinilo C2-12, cicloalquilo C3-12, arilo, o aril alquilo C1-12; en donde cualquiera de los grupos alquilo, alquenilo, alquinilo, cicloalquilo, arilo, o grupos arilalquilo está opcionalmente sustituido con uno o más halogeno, oxo, CN, OCF3, OH, NH2, o NO2; y donde el compuesto de formula (2), en donde R15 es como define para R1, R16, es como se define para R3, y R17 es como se define para R4 en el compuesto de formula (1); y F es OH, NH2, o S(O)2CF3; y en donde el compuesto de formula (3) es definido como el compuesto de formula (2) excepto que F ha sido alquilado para formar O(alquiloC1-3)C(O)YR2; NR5(alquiloC1-3)C(O)YR2, S(alquiloC1-3)C(O)YR2, SO(alquiloC1- 3)C(O)YR2 o SO2(alquiloC1-3)C(O)YR2, donde Y, R2, y R5 son definidos tal para el compuesto de formula (1).
ARP050100660A 2004-02-25 2005-02-23 Derivados de tiofeno como inhibidores de la proteina tirosina fosfatasa 1b (ptpasa 1b); metodos para su preparacion, composiciones farmaceuticas que los contienen y su uso en el tratamiento de enfermedades mediadas por ptpasa 1b AR047894A1 (es)

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