AR043053A1 - Ligandos del receptor vaniloide, composiciones farmaceuticas que los contienen, y metodos de preparacion del compuesto - Google Patents
Ligandos del receptor vaniloide, composiciones farmaceuticas que los contienen, y metodos de preparacion del compuestoInfo
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- AR043053A1 AR043053A1 ARP030103783A ARP030103783A AR043053A1 AR 043053 A1 AR043053 A1 AR 043053A1 AR P030103783 A ARP030103783 A AR P030103783A AR P030103783 A ARP030103783 A AR P030103783A AR 043053 A1 AR043053 A1 AR 043053A1
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Abstract
Bencimidazoles terapéuticos y composiciones que los contengan, son útiles para el tratamiento de dolores agudos, inflamatorios o neuropáticos, dolores dentales, dolores de cabeza en general, migrana, dolor de cabeza "en racimo" (cluster headache), síndromes mixtos vasculares y no vasculares, dolor de cabeza por tensión, inflamación general, artritis, enfermedades reumáticas, osteoartritis, enfermedad inflamatoria intestinal, trastornos oculares inflamatorios, trastornos vesiculares inflamatorios o inestables, psoriasis, molestias de la piel con componentes inflamatorios, patologías inflamatorias crónicas, dolor inflamatorio e hiperalgesia y alodinia asociadas, dolor neuropático e hiperalgesia y alodinia asociadas, dolor neuropático diabético, causalgia, dolor mantenido por el simpático, síndromes de deaferenciación, asma, danos o disfunciones de tejidos epiteliales, herpes simplex, trastornos de motilidad visceral en las regiones respiratoria, genitourinaria, gastrointestinal o vascular, heridas, quemaduras, reacciones alérgicas de la piel, prurito, vitiligo, trastornos gastrointestinales generales, úlceras gástricas, úlceras duodenales, diarrea, lesiones gástricas inducidas por agentes necrotizantes, crecimiento del cabello, rinitis vasomotora o alérgica, trastornos bronquiales o trastornos de la vesícula. Reivindicación 1: Un compuesto que tiene la estructura de la fórmula (1) o cualquiera de sus sales farmacéuticamente aceptables, donde L1 es una cadena saturada, insaturada o parcialmente saturada de 1, 2 ó 3 átomos de carbono sustituida en cada posición abierta por R2; L2 es una cadena saturada, insaturada o parcialmente saturada de 1, 2 ó 3 átomos de carbono sustituida en cada posición abierta por R2'; donde la cantidad combinada de átomos de carbono en las cadenas L1 y L2 es 4 ó 5; donde, cuando L1 es una cadena de un carbono y tanto Q1 como Q2 son N, L1 es carbonilo, y cuando L2 es una cadena de un carbono y tanto Q1 como Q2 son N, L2 es carbonilo; m es independientemente en cada instancia 0, 1 ó 2; Q1 es N ó C(R2); Q2 es N ó C(R2); donde al menos uno de Q1 y Q2 es N; Q3 es N ó C(R5); Q4 es N ó C(R6); Q5 es N ó C(R6'); Q6 es N ó C(R5'); R1 es H ó -(C(R2)(R2))m-Rg; R2 es, independientemente, en cada instancia, H, alquilo C1-8, haloalquilo C1-4, -O(alquilo C1-7), -N(alquilo C1-7)Ra, ó un alquilo C1 6 sustituido por 1, 2 ó 3 sustituyentes seleccionados de halo, ciano, -ORa, -OC(=O)Rb, -SRa, -S(=O)Rb, -S(=O)2Rb, -S(=O)2NRaRa, -NRaRa, -N(Ra)C(=O)Rb, -N(Ra)C(=O)ORb, -N(Ra)C(=O)NRaRa, -N(Ra)C(=NRa)NRaRa, -N(Ra)S(=O)2Rb, -NRaalquil C2-6-NRaRa y -NRaalquil C2-6-ORa; donde cualesquiera dos grupos R2 geminales pueden ser, adicionalmente, oxo; R2' es, independientemente, en cada instancia, H, alquilo C1-8, haloalquilo C1-4, -O(alquilo C1-7), -N(alquilo C1-7)Ra, ó un alquilo C1-6 sustituido por 1, 2 ó 3 sustituyentes seleccionados de halo, ciano, -ORa, -OC(=O)Rb, -SRa, -S(=O)Rb, -S(=O)2Rb, -S(=O)2NRaRa, -NRaRa, -N(Ra)C(=O)Rb, -N(Ra)C(=O)ORb, -N(Ra)C(=O)NRaRa, -N(Ra)C(=NRa)NRaRa, -N(Ra)S(=O)2Rb, -NRaalquil C2-6NRaRa y -NRaalquil C2-6ORa; donde cualesquiera dos grupos R2' geminales pueden ser, adicionalmente, oxo; R4 es fenilo ó naftilo, donde el fenilo y el naftilo son sustituidos por 1, 2, 3 ó 4 sustituyentes seleccionados de Rc, Re, halo, haloalquilo C1-4, ciano, nitro, -C(=O)Re, -C(=O)ORh, -C(=O)NRaRh, -C(=NRa)NRaRh, -ORh, -OC(=O)Re, -OC(=O)NRaRh, -OC(=O)N(Ra)S(=O)2Re, -Oalquil C2-6NRaRh, -Oalquil C2-6ORh, -SRe, -S(=O)Re, -S(=O)2Re, -S(=O)2NRaRh, -S(=O)2N(Ra)C(=O)Re, -S(=O)2N(Ra)C(=O)ORh, -S(=O)2n(Ra)C(=O)NRaRh, -NRaRh, -N(Ra)C(=O)Re, -N(Ra)C(=O)ORh, -N(Ra)C(=O)NRaRh, -N(Ra)C(=NRa)NRaRh, -N(Ra)S(=O)2Re, -N(Ra)S(=O)2NRaRh, -NRaalquil C2-6NRaRh, -NRaalquil C2-6ORh, -C(=O)Rg, -C(=O)ORg, -C(=O)NRaRg, -C(=NRa)NRaRg, -ORg, -OC(=O)Rg, -OC(=O)NRaRg, -OC(=O)N(Ra)S(=O)2Rg, -OC(=O)N(Rg)S(=O)2Re, -Oalquil C2-6NRaRg, -Oalquil C2-6ORg, -SRg, -S(=O)Rg, -S(=O)2Rg, -S(=O)2NRaRg, -S(=O)2N(Rg)C(=O)Re, -S(=O)2N(Ra)C(=O)Rg, -S(=O2)N(Rg)C(=O)ORh, -S(=O)2N(Ra)C(=O)Rg, -S(=O)2N(Rg)C(=O)NRaRh, -S(=O2)N(Ra)C(=O)NRaRg, -NRaRg, -N(Rg)C(=O)Re, -N(Ra)C(=O)Rg, -N(Rg)C(=O)ORh, -N(Ra)C(=O)ORg, -N(Rg)C(=O)NRaRh, -N(Ra)C(=O)NRaRg, -N(Rg)C(=NRa)NRaRh, -N(Ra)C(=NRa)NRaRg, -N(Rg)S(=O)2Re, -N(Ra)S(=O)2Rg, -N(Rg)S(=O2)NRaRh, -N(Ra)S(=O)2NRaRg, -NRhalquil C2-6NRaRg, -NRaalquil C2-6NRaRg, -NRgalquil C2-6ORh y -NRaalquil C2-6ORg; ó bien R4 es Rc sustituido por 0, 1, 2, 3 ó 4 sustituyentes que se seleccionan de Rc, Re, halo, haloalquilo C1-4, ciano, nitro, -C(=O)Re, -C(=O)ORh, -C(=O)NRaRh, -C(=NRa)NRaRh, -ORh, -OC(=O)Re, -OC(=O)NRaRh, -OC(=O)N(Ra)S(=O)2Re, -Oalquil C2-6NRaRh, -Oalquil C2-6ORh, -SRe, -S(=O)Re, -S(=O)2Re, -S(=O)2NRaRh, -S(=O)2N(Ra)C(=O)Re, -S(=O)2N(Ra)C(=O)ORh, -S(=O)2N(Ra)C(=O)NRaRh, -NRaRh, -N(Ra)C(=O)Re, -N(Ra)C(=O)ORh, -N(Ra)C(=O)NRaRh, -N(Ra)C(=NRa)NRaRh, -N(Ra)S(=O)2Re, -N(Ra)S(=O)2NRaRh, -NRaalquil C2-6NRaRh, -NRaalquil C2-6ORh, -C(=O)Rg, -C(=O)ORg, -C(=O)NRaRg, -C(=NRa)NRaRg, -ORg, -OC(=O)Rg, -OC(=O)NRaRg, -OC(=O)N(Ra)S(=O)2Rg, -OC(=O)N(Rg)S(=O)2Re, -Oalquil C2-6NRaRg, -Oalquil C2-6ORg, -SRg, -S(=O)Rg, -S(=O)2Rg, -S(=O2)NRaRg, - S(=O)2N(Rg)C(=O)Re, -S(=O)2N(Ra)C(=O)Rg, -S(=O2)N(Rg)C(=O)ORh, -S(=O)2N(Ra)C(=O)ORg, -S(=O)2N(Rg)C(=O)NRaRh, -S(=O)2N(Ra)C(=O)NRaRg, -NRaRg, -N(Rg)C(=O)Re, -N(Ra)C(=O)Rg, -N(Rg)C(=O)ORh, -N(Ra)C(=O)ORg, -N(Rg)C(=O)NRaRh, -N(Ra)C(=O)NRaRg, -N(Rg)C(=NRa)NRaRh, -N(Ra)C(=NRa)NRaRg, -N(Rg)S(=O)2Re, -N(Ra)S(=O)2Rg, -N(Rg)S(=O)2NRaRh, -N(Ra)S(=O)2NRaRg, -NRhalquil C2-6NRaRg, -NRaalquil C2-6NRaRg, -NRgalquil C2-6ORh y -NRaalquil C2-6ORg; R5 es H, Re, haloalquilo C1-4, halo, ciano, -C(=O)Re, -C(=O)ORe, -C(=O)NReRa, -C(=NRa)NRhRa, -ORh, -OC(=O)Re, -OC(=O)NRaRh, -OC(=O)N(Ra)S(=O)2Re, -Oalquil C2-6NRaRh, -Oalquil C2-6ORh, -SRh, -S(=O)Re, -S(=O)2Re, -S(=O2)NRaRh, -S(=O)2N(Ra)C(=O)Re, -S(=O)2N(Ra)C(=O)OR3, -S(=O)2N(Ra)C(=O)NRaRh, -NRaRh, -N(Ra)C(=O)Re, -N(Ra)C(=O)ORe, -N(Ra)C(=O)NRaRh, -N(Ra)C(=NRa)NRaRh, -N(Ra)S(=O)2Re, -N(Ra)S(=O)2NRaRh, -NRaalquil C2-6NRaRh, -NRaalquil C2-6ORh, -C(=O)Rg, -C(=O)ORg, -C(=O)NRgRa, -C(=NRa)NRaRg, -ORg, -OC(=O)Rg, -OC(=O)NRaRg, -OC(=O)N(Ra)S(=O)2Rg, -Oalquil C2-6NRaRg, -Oalquil C2-6ORg, -SRg, -S(=O)Rg, -S(=O)2Rg, -S(=O)2NRaRg, -S(=O)2N(Ra)C(=O)Rg, -S(=O)2N(Ra)C(=O)ORg, -S(=O)2N(Ra)C(=O)NRaRg, -NRaRg, -N(Ra)C(=O)Rg, -N(Ra)C(=O)ORg, -N(Ra)C(=O)NRaRg, -N(Ra)C(=NRa)NRaRg, -N(Ra)S(=O)2Rg, -N(Ra)S(=O)2NRaRg, -NRaalquil C2-6NRaRg ó -NRaalquil C2-6ORg; ó bien R5 es una cadena cerrada, saturada o insaturada, monocíclica de 5, 6 ó 7 miembros o bicíclica de 6, 7, 8, 9, 10 u 11 miembros que contiene 0, 1, 2, 3 ó 4 átomos seleccionados de N, O y S, donde los átomos de carbono de la cadena cerrada son sustituidos por 0, 1 ó 2 grupos oxo y la cadena cerrada es sustituida por 0, 1, 2, 3 ó 4 sustituyentes seleccionados de Re, haloalquilo C1-4, halo, ciano, nitro, -C(=O)Re, -C(=O)ORe, -C(=O)NReRa, -C(=NRa)NRhRa, -ORh, -OC(=O)Re, -OC(=O)NRaRh, -OC(=O)N(Ra)S(=O)2Re, -Oalquil C2-6NRaRh, -Oalquil C2-6ORh, -SRh, -S(=O)Re, -S(=O)2Re, -S(=O)2NRaRh, -S(=O)2N(Ra)C(=O)Re, -S(=O)2N(Ra)C(=O)ORe, -S(=O)2N(Ra)C(=O)NRaRh, -NRaRh, -N(Ra)C(=O)Re, -N(Ra)C(=O)ORe, -N(Ra)C(=O)NRaRh, -N(Ra)C(=NRa)NRaRh, -N(Ra)S(=O)2Re, -N(Ra)S(=O)2NRaRh, -NRaalquil C2-6NRaRh, -NRaalquil C2-6ORh, -C(=O)Rg, -C(=O)ORg, -C(=O)NRgRa, -C(=NRa)NRaRg, -ORg, -OC(=O)Rg, -OC(=O)NRaRg, -OC(=O)N(Ra)S(=O)2Rg, -Oalquil C2-6NRaRg, -Oalquil C2-6ORg, -SRg, -S(=O)Rg, -S(=O2)Rg, -S(=O)2NRaRg, -S(=O)2N(Ra)C(=O)Rg, -S(=O)2N(Ra)C(=O)ORg, -S(=O)2N(Ra)C(=O)NRaRg, -NRaRg, -N(Ra)C(=O)Rg, -N(Ra)C(=O)ORg, -N(Ra)C(=O)NRaRg, -N(Ra)C(=NRa)NRaRg, -N(Ra)S(=O)2Rg, -N(Ra)S(=O)2NRaRg, -NRaalquil C2-6NRaRg y -NRaalquil C2-6ORg; R5' es H, Re, haloalquilo C1-4, halo, ciano, -C(=O)Re, -C(=O)ORe, -C(=O)NReRa, -C(=NRa)NRhRa, -ORh, -OC(=O)Re, -OC(=O)NRaRh, -OC(=O)N(Ra)S(=O)2Re, -Oalquil C2-6NRaRh, -Oalquil C2-6ORh, -SRh, -S(=O)Re, -S(=O)2Re, -S(=O2)NRaRh, -S(=O)2N(Ra)C(=O)Re, -S(=O)2N(Ra)C(=O)ORe, -S(=O)2N(Ra)C(=O)NRaRh, -NRaRh, -N(Ra)C(=O)Re, -N(Ra)C(=O)ORe, -N(Ra)C(=O)NRaRh, -N(Ra)C(=NRa)NRaRh, -N(Ra)S(=O)2Re, -N(Ra)S(=O)2NRaRh, -NRaalquil C2-6NRaRh, -NRaalquil C2-6ORh, -C(=O)Rg, -C(=O)ORg, -C(=O)NRgRa, -C(=NRa)NRaRg, -ORg, -OC(=O)Rg, -OC(=O)NRaRg, -OC(=O)N(Ra)S(=O)2Rg, -Oalquil C2-6NRaRg, -Oalquil C2-6ORg, -SRg, -S(=O)Rg, -S(=O)2Rg, -S(=O)2NRaRg, -S(=O)2N(Ra)C(=O)Rg, -S(=O)2N(Ra)C(=O)ORg, -S(=O)2N(Ra)C(=O)NRaRg, -NRaRg, -N(Ra)C(=O)Rg, -N(Ra)C(=O)ORg, -N(Ra)C(=O)NRaRg, -N(Ra)C(=NRa)NRaRg, -N(Ra)S(=O)2Rg, -N(Ra)S(=O)2NRaRg, -NRaalquil C2-6NRaRg ó -NRaalquil C2-6ORg; ó bien R5' es una cadena cerrada, saturada o insaturada, monocíclica de 5, 6 ó 7 miembros o bicíclica de 6, 7, 8, 9, 10 u 11 miembros que contiene 0, 1, 2, 3 ó 4 átomos seleccionados de N, O y S, donde los átomos de carbono de la cadena cerrada son sustituidos por 0, 1 ó 2 grupos oxo y la cadena cerrada es sustituida por 0, 1, 2, 3 ó 4 sustituyentes que se seleccionan de Re, haloalquilo C1-4, halo, ciano, nitro, -C(=O)Re, -C(=O)ORe, -C(=O)NReRa, -C(=NRa)NRhRa, -ORh, -OC(=O)Re, -OC(=O)NRaRh, -OC(=O)N(Ra)S(=O)2Re, -Oalquil C2-6NRaRh, -Oalquil C2-6ORh, -SRh, -S(=O)Re, -S(=O)2Re, -S(=O)2NRaRh, -S(=O)2N(Ra)C(=O)Re, -S(=O)2N(Ra)C(=O)ORe, -S(=O)2N(Ra)C(=O)NRaRh, -NRaRh, -N(Ra)C(=O)Re, -N(Ra)C(=O)ORe, -N(Ra)C(=O)NRaRh, -N(Ra)C(=NRa)NRaRh, -N(Ra)S(=O)2Re, -N(Ra)S(=O)2NRaRh, -NRaalquil C2-6NRaRh, -NRaalquil C2-6ORh, -C(=O)Rg, -C(=O)ORg, -C(=O)NRgRa, -C(=NRa)NRaRg, -ORg, -OC(=O)Rg, -OC(=O)NRaRg, -OC(=O)N(Ra)S(=O)2Rg, -Oalquil C2-6NRaRg, -Oalquil C2-6ORg, -SRg, -S(=O)Rg, -S(=O)2Rg, -S(=O)2NRaRg, -S(=O)2N(Ra)C(=O)Rg, -S(=O)2N(Ra)C(=O)ORg, -S(=O2)N(Ra)C(=O)NRaRg, -NRaRg, -N(Ra)C(=O)Rg, -N(Ra)C(=O)ORg, -N(Ra)C(=O)NRaRg, -N(Ra)C(=NRa)NRaRg, -N(Ra)S(=O)2Rg, -N(Ra)S(=O)2NRaRg, -NRaalquil C2-6NRaRg y -NRaalquil C2-6ORg; R6 es H, haloalquilo C1-4, halo, ciano, -C(=O)Rb, -C(=O)ORb, -C(=O)NRaRa, -C(=NRa)NRaRa, -OH, -Oalquilo C2-6, -OC(=O)Rb, -OC(=O)NRaRa, -OC(=O)N(Ra)S(=O)2Rb, -Oalquil C2-6NRaRa, -Oalquil C2-6Ra, -SRa, -S(=O)Rb, -S(=O)2Rb, -S(=O)2NRaRa, -S(=O)2n(Ra)C(=O)Rb, -S(=O)2N(Ra)C(=O)ORb, -S(=O)2N(Ra)C(=O)NRaRa, -NRaRb, -N(Ra)C(=O)Rb, -N(Ra)
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- 2003-10-16 US US10/688,246 patent/US7582761B2/en not_active Expired - Fee Related
- 2003-10-16 EP EP03809075A patent/EP1551811A1/en not_active Withdrawn
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US7582761B2 (en) | 2009-09-01 |
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JP2006505570A (ja) | 2006-02-16 |
AU2003301436A1 (en) | 2004-05-04 |
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MXPA05003948A (es) | 2005-06-17 |
TW200418807A (en) | 2004-10-01 |
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