AR066386A1 - Compuestos heterociclicos condensados, metodos e intermediarios para su preparacion, una composicion farmaceutica que los comprende y su uso en el tratamiento de enfermedades mediadas por la inhibicion de la pde-4 - Google Patents

Compuestos heterociclicos condensados, metodos e intermediarios para su preparacion, una composicion farmaceutica que los comprende y su uso en el tratamiento de enfermedades mediadas por la inhibicion de la pde-4

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Publication number
AR066386A1
AR066386A1 ARP050105281A ARP050105281A AR066386A1 AR 066386 A1 AR066386 A1 AR 066386A1 AR P050105281 A ARP050105281 A AR P050105281A AR P050105281 A ARP050105281 A AR P050105281A AR 066386 A1 AR066386 A1 AR 066386A1
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Argentina
Prior art keywords
substituted
unsubstituted
carboxylate
methoxy
furan
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ARP050105281A
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English (en)
Inventor
Atmaram Gharat Laxmikant
Gopalan Balasubramanian
Khairatkar-Joshi Neelima
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Glenmark Pharmaceuticals Sa
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Publication of AR066386A1 publication Critical patent/AR066386A1/es

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    • C07D495/04—Ortho-condensed systems

Abstract

Composiciones farmacéuticas que los contengan, que son utiles en el tratamiento de enfermedades alérgicas e inflamatorias incluyendo asma, bronquitis cronica, dermatitis atopica, urticaria, rinitis alérgica, conjuntivitis alérgica, conjuntivitis vernal, granuloma eosinofílico, psoriasis, artritis reumatoide, shock séptico, colitis ulcerante, enfermedad de Crohn, dano del miocardio por reperfusion, dano del cerebro por reperfusion, glomerulonefritis cronica, shock endotoxico y síndrome de dificultad respiratoria en adultos. Reivindicacion 1: Un compuesto de formula (1) en la cual; en cada caso R1, R2 y R3 pueden ser idénticos o diferentes, y son, independientemente, hidrogeno, alquilo substituido o no substituido, alquenilo substituido o no substituido, alquinilo substituido o no substituido, cicloalquilo substituido o no substituido, cicloalquilalquilo substituido o no substituido, cicloalquenilo substituido o no substituido, cicloalquenilalquilo substituido o no substituido, arilo substituido o no substituido, arilalquilo substituido o no substituido, heteroarilo substituido á no substituido, heteroarilalquilo substituido o no substituido, un grupo heterocíclico substituido o no substituido, heterociclilalquilo substituido o no substituido, -NR5R6, -C(=L)-R5, -C(O)-R5, -C(O)O-R5, -C(O)NR5R6, -S(O)m-R5, -S(O)m-NR5R6, nitro, -OH, ciano, oxo, formilo, acetilo, halogeno, -OR5, -SR5, o un grupo protector, o cuando dos substituyentes R2 o dos substituyentes R3 se encuentran en posicion orto entre sí, los dos substituyentes pueden estar unidos para formar un anillo cíclico de 3-7 miembros opcionalmente substituido, saturado o no saturado, que de manera opcional puede incluir hasta dos heteroátomos seleccionados de entre O, NR5 o S; en cada caso, R5 y R6 pueden ser idénticos o diferentes y son, de manera independiente, hidrogeno, alquilo substituido o no substituido, alquenilo substituido o no substituido, alquinilo substituido o no substituido, cicloalquilo substituido o no substituido, cicloalquilalquilo substituido o no substituido, cicloalquenilo substituido o no substituido, cicloalquenilalquilo substituido o no substituido, arilo substituido o no substituido, arilalquilo substituido o no substituido, heteroarilo substituido o no substituido, heteroarilalquilo substituido o no substituido, un grupo heterocíclico substituido o no substituido, heterociclilalquilo substituido o no substituido, nitro, halo, -OH, ciano, -C(O)-Ra, -C(O)O-Ra, -C(O)NRaRb, -S(O)m-Ra, -S(O)m-NRaRb, -C(=NRa)-Rb, -C(=NRa)-NRaRb, -C(=S)-NRaRb, -C(=S)-Ra, -N=C(RaRb), -NRaRb, -ORa, -SRa, o un grupo protector, o R5 y R6 pueden estar unidos entre sí junto con el átomo al cual están enlazados para formar un anillo cíclico de 3-7 miembros opcionalmente substituido, saturado o no saturado, que de manera opcional puede incluir hasta dos heteroátomos seleccionados de entre O, NRa o S; en cada caso, Ra y Rb pueden ser idénticos o diferentes, y son, de manera independiente, hidrogeno, alquilo substituido o no substituido, alquenilo substituido o no substituido, alquinilo substituido o no substituido, cicloalquilo substituido o no substituido, cicloalquilalquilo substituido o no substituido, cicloalquenilo substituido o no substituido, cicloalquenilalquilo substituido o no substituido, arilo substituido o no substituido, arilalquilo substituido o no substituido, heteroarilo substituido o no substituido, heteroarilalquilo substituido o no substituido, un grupo heterocíclico substituido o no substituido, heterociclilalquilo substituido o no substituido, nitro, -OH, ciano, formilo, acetilo, halogeno, un grupo protector, -C(O)-Ra, -C(O)O-Ra, -C(O)NRaRb, -S(O)m-Ra, -S(O)m-NRaRb, NRaRb, -ORa, o -SRa; Ar es arilo substituido o no substituido, arilalquilo substituido o no substituido, anillo heterocíclico substituido o no substituido, heterocicloalquilo substituido o no substituido, un anillo heteroarilo substituido o no substituido, o heteroarilalquilo substituido o no substituido; L es O, S o NRa, en donde Ra es tal como se define anteriormente; n es un entero desde 0 a 2; p es un entero desde 0 a 8; T, U, V y W son cada uno, de manera independiente, C, C=O, N, NRa, O o S, siempre que al menos uno de T, U, V y W sea N, NRa, O o S, y en donde Ra es tal como se define anteriormente; cada línea entrecortada [-----] en el anillo representa un enlace opcionalmente doble; X es O, S(O)m o NRb, en donde Rb es tal como se define anteriormente; en cada caso, m es independientemente 0, 1 o 2; Y es -C(O)NR4-, -NR4SO2-, -SO2NR4- o -NR4C(O)-; R4 es hidrogeno, alquilo substituido o no substituido, hidroxilo, -ORa (en donde Ra es tal como se define anteriormente) , cicloalquilo substituido o no substituido, cicloalquilalquilo substituido o no substituido, arilo substituido o no substituido, arilalquilo substituido o no substituido, un anillo heterocíclico substituido o no substituido, heterocicloalquilo substituido o no substituido, un anillo heteroarilo substituido o no substituido o heteroarilalquilo substituido o no substituido, o un análogo, tautomero, regioisomero, estereoisomero, enantiomero, diasteromero, polimorfo, sal farmacéuticamente aceptable, N-oxido, o un solvato farmacéuticamente aceptable de los mismos. Reivindicacion 56: Un compuesto que es: etil 4-formil-7-metoxi-3-metilbenzo[b] furan-2-carboxilato; ácido 2-etoxicarbonil-7-metoxi-3-metilbenzo[b] furan-4-carboxílico; 2-etil-4-metil-7-metoxi-3-metilbenzo [b] furan-2,4-dicarboxilato; 2-etil-4-metil-3-bromometil-7-metoxibenzo [b] furan-2,4-dicarboxilato; 2-etil-4-metil 3-formil-7-metilbenzo[b)furan-2,4-dicarboxilato; metil-7-metoxi-2-metilbenzo [b] furan-4-carboxilato; metil-2-bromometil-7-metoxibenzo [b] furan-4-carboxilato; metil-2-formil-7-metoxibenzo [b] furan-4-carboxilato; ácido (Z)-3-(7-metoxi-4-metiloxicarbonilbenzo [b] furan-2-il)-2-propenoico; metil-2-[(Z)-2-azidocarbonil)-1-etenil]-7-metoxibenzo [b] furan-4-carboxilato; ácido 2-etoxicarbonil-7-hidroxi-3-metilbenzo [b] furan-4-carboxílico; 2,4-dietil-7-hidroxi-3-metilbenzo[b]furan-2,4-dicarboxilato, 2,4-dietil-7-difluorometoxi-3-metilbenzo [b] furan-2,4-dicarboxilato; dietil 3-bromometil-7-difluorometoxibenzo [b] furan-2,4-dicarboxilato; dietil 7-difluorometoxi-3-formilbenzo [b] furan-2,4-dicarboxilato; 2-(7-metoxi-1-benzofuran-2-il) etanamina; etil 2-(7-metoxi-1-benzofuran-2-il) etilcarbamato; 7-hidroxi-2-metilbenzo [b] furan-4-carbaldehido; 7-ciclopentiloxi-2-metilbenzo [b) furan-4-carboxaldehído; ácido 7-ciclopentiloxi-2-metilbenzo [b] furan-4-carboxílico; metil-7-ciclopentiloxi-2-metilbenzo [b] furan-4-carboxilato; metil-7-ciclopentiloxi-2-bromometilbenzo [b] furan-4-carboxilato; metil-2-formil-7-ciclopentiloxibenzo [b] furan-4-carboxilato; ácido (Z)-3-(7-ciclopentiloxi-4-metiloxicarbonilbenzo [b] furan-2-il)-2-propenoico; metil-2-[(Z)-2-azidocarbonil)-1-etenil]-7-metoxibenzo [b] furan-4-carboxilato; 2-(7-metoxibenceno [b] tiofen-3-il) acetamida; 2-(7-metoxibenceno [b] tiofen-3-il) etilamina; etil 2-(7-metoxibenceno [b] tiofen-3-il) etilcarbamato; etil-2-(7-metoxi-1-benzofuran-3-il)etilcarbamato; o 1-metil-3-(2-metoxi-5-carbmetoxi-fenil-hidrazono)-piperidin-2-ona. Reivindicacion 57 Un compuesto que es metil(6-metoxi-4-oxo-3,4-dihidrobenzo[4,5] furo[2,3-d]piridazin-9-carboxilato; metil(4-cloro-6-metoxibenzo [4,5] furo[2,3-d] piridazin)-9-carboxilato; metil (6-metoxibenzo [4,5]furo[2,3-d]piridazin)-9-carboxilato; 6-metoxibenzo [4,5] furo [2,3-d] piridazin-9-carboxílico ácido; 4-nitrofenil 6-metoxibenzo [4,5] furo [2,3-d] piridazin-9-carboxilato, 6-metoxi-3,4-dihidrobenzo [4,5] furo [3,2-d] pirimidin-4-ona; 6-metoxibenzo [4,5] furo [3,2-d] pirimidina; 9-bromo-6-metoxibenzo [4,5] furo [3,2-d] pirimidina; 6-metoxibenzo [4,5] furo [3,2-d] pirimidin-9-il cianida; ácido 6-metoxibenzo [4,5] furo [3,2-d]pirimidin-9-carboxílico; 4-nitrofenil 6-metoxibenzo [4,5] furo [3,2-d]pirimidin-9-carboxilato; etil-8-metoxi-1,2,3,4-tetrahidrobenzo [4,5] tieno [2,3-c]piridin-2-carboxilato; etil-5-formil-8-metoxi-1,2,3,4-tetrahidrobenzo [4,5] tieno[2,3-c]piridin-2-carboxilato; ácido 2-etoxicarbonil-8-metoxi-1,2,3,4-tetrahidrobenzo [4,5] tieno [2,3-] piridin-5-carboxílico; 2-etil-5-(4-nitrofenil)-8-metoxi-1,2,3,4-tetrahidrobenzo[4, 5] tieno [2,3-c] piridin-2,5-dicarboxilato; 2-etil-5-(4-nitrofenil)-8-metoxi-1,2,3,4-tetrahidrobenzo [4,5] tieno [2,3-c] piridin-2,5-dicarboxilato; etil-6-difluorometoxi-4-oxo-3,4-dihidrobenzo [4,5] furo [2,3-d]piridazin-9-carboxilato; etil-4-cloro-6-difluorometoxibenzo [4,5] furo [2,3-d] piridazin-9-carboxilato; etil-6-difluorometoxibenzo [4,5] furo [2,3-d]piridazin-9-carboxilato; ácido 6-Difluorometoxibenzo [4,5] furo [2,3-d] piridazin-9-carboxílico; 4-nitrofenil 6-difluorometoxibenzo [4,5] furo [2,3-d]piridazin-9-carboxilato; ácido 2-tert-butiloxicarbonil-8-metoxi-1,2,3,4-tetrahidrobenzo[4,5]tieno[2,3-c] piridin-5-carboxílico; 2(tert-butil)-5-(4-nitrofenil)-8-metoxi-1,2,3,4-tetrahidrobenzo [4,5]tieno [2,3-c] piridin-2,5-dicarboxilato; tert-butil-5-(3,5-dicloro-4-piridilcarbamoil)-8-metoxi-1,2,3,4-tetrahidrobenzo [4,5] tieno[2,3-c)piridin-2-carboxilato; 2-etoxicarbonil-6-metoxi-1,2,3,4-tetrahidro[1]benzofuro[3,2-c]piridina; 2-etoxicarbonil-6-metoxi-1,2,3,4-tetrahidro [1]benzofuro(3,2-c]piridin-9-carbaldehído; ácido 2-etoxicarbonil-6-metoxi-1,2,3,4-tetrahidro[12]benzofuro(3,2-c]piridin-9-carboxílico; 4-nitrofenil-(2-etoxicarbonil]-6-metoxi-1,2,3,4-tetrahidro[1]benzofuro[3,2-c]piridin)-9-carboxilato; metil-1-hidroxi-6-metoxibenzo[4,5]furo[3,2-c] piridin-9-carboxilato; metil-1-cloro-6-metoxibenzo[4,5]furo[3,2-c]piridin-9-carboxilato; meti6-metoxibenzo[4,5]furo[3,2-c)piridin-9-carboxilato; 6-metoxibenzo[4,5]furo[3,2-c]piridin-9-carboxílico ácido; 4-nitrofenil-6-metoxibenzo[4.5] furo[3,2-c]piridin-9-carboxilato; etil 8-metoxi-3,4-dihidro[1]benzofuro[2,3-c]piridin-2(1H)-carboxilato; etil 5-formil-8-metoxi-3,4-dihidro[1]-benzofuro[2,3-c]piridin-2(1H)-carboxilato; ácido 2-(etoxicarbonil)-8-metoxi-1,2,3,4-tetrahidro[1]benzofuro [2,3-c] piridin-5-carbox
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