AR064524A1 - Derivados de n-(amino-(hetero)aril)-1h-pirrolopiridin-2-carboxamidas, su preparacion, intermediarios para su sintesis, una composicion farmaceutica que los comprende y su uso en la fabricacion de medicamentos para el tratamiento de enfermedades mediadas por los receptores de tipo trpv1. - Google Patents
Derivados de n-(amino-(hetero)aril)-1h-pirrolopiridin-2-carboxamidas, su preparacion, intermediarios para su sintesis, una composicion farmaceutica que los comprende y su uso en la fabricacion de medicamentos para el tratamiento de enfermedades mediadas por los receptores de tipo trpv1.Info
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- AR064524A1 AR064524A1 ARP070105891A ARP070105891A AR064524A1 AR 064524 A1 AR064524 A1 AR 064524A1 AR P070105891 A ARP070105891 A AR P070105891A AR P070105891 A ARP070105891 A AR P070105891A AR 064524 A1 AR064524 A1 AR 064524A1
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Abstract
Procedimiento de preparacion y aplicacion en terapéutica contra enfermedades mediadas por los receptores de tipo TRPV1. Reivindicacion 1: Un compuesto que responde a la formula (1) en la que el nucleo de pirrolopiridina es un grupo pirrolo[3,2- b]piridina, un grupo pirrolo[3,2- c]piridina, un grupo pirrolo[2,3-c)piridina o un grupo pirrolo[2,3-b]piridina; estando el nucleo de pirrolopiridina eventualmente sustituido en los carbonos de posicion 4, 5, 6 y/o 7 con uno o varios sustituyentes X, idénticos o diferentes uno de otro, elegidos entre un átomo de hidrogeno o de halogeno o un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, cicloalcoxilo C3-7, cicloalquil C3-7-alquileno C1-6-O-, fluoroalcoxilo C1-6, ciano, tioalquilo C1-6, -S(O)-alquilo C1-6, -S(O)2alquilo C1-6, SF5, C(O)NR1R2, SO2NR1R2, nitro, NR1R2, OCONR1R2, NR3COR4, NR3CONR1R2, NR3SO2R5, NR3SO2NR1R2, aril-alquileno C1-6, heteroaril-alquileno C1-6, arilo o heteroarilo, estando el arilo y el heteroarilo eventualmente sustituidos con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, fluoroalcoxilo C1-6, nitro o ciano; n es igual a 0, 1, 2 o 3; Y representa un arilo o un heteroarilo, estando el arilo o el heteroarilo eventualmente sustituidos con uno o varios grupos elegidos entre un átomo de halogeno o un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, hidroxilo, alcoxilo C1-6, cicloalcoxilo C3-7, cicloalquil C3-7-alquileno C1-6-O-, fluoroalcoxilo C1-6, ciano, tioalquilo C1-6, tiol, -S(O)-alquilo C1-6, -S(O)2-alquilo C1-6, C(O)NR1R2, SO2NR1R2, SF5, nitro, OCONR1R2, NR3COR4, NR3CONR1R2, NR1R2, NR3SO2NR1R2, NR3COR4, NR3SO2R5, aril-alquileno C1-6, o arilo, estando el arilo y el aril-alquileno C1-6 eventualmente sustituidos con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, fluoroalcoxilo C1-6, nitro o ciano; Z1, Z2, Z3, Z4 representan, independientemente uno de otro, un átomo de nitrogeno o un grupo C(R6), correspondiendo uno al menos a un átomo de nitrogeno y correspondiendo uno al menos a un grupo C(R6); estando el átomo de nitrogeno o uno de los átomos de nitrogeno presentes en el ciclo, definido como nitrogeno de posicion 1, eventualmente sustituido con R7 cuando el átomo de carbono en posicion 2 o 4 con respecto a este nitrogeno de referencia está sustituido con un grupo oxo o tio; Z representa o bien una amina cíclica unida por el átomo de nitrogeno, de la formula (2) en la que A representa un grupo alquileno C1-7 eventualmente sustituido con uno o dos grupos R8; B representa un grupo alquileno C1-7 eventualmente sustituido con uno o dos grupos R9; L representa un enlace, un átomo de azufre, de oxígeno o de nitrogeno; estando el átomo de nitrogeno eventualmente sustituido con un grupo R10 o R11; estando los átomos de carbono de la amina cíclica Z eventualmente sustituidos con uno o varios grupos R12 idénticos o diferentes uno de otro; o bien una amina acílica, unida por el átomo de nitrogeno, de la formula NRaRb en la que Ra y Rb representan, independientemente uno de otro, un átomo de hidrogeno o un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, hidroxilo, alcoxilo C1-6, cicloalquil C3-7-alquileno C1-6-O-, fluoroalcoxilo C1-6, alquil C1-6-C(O)-, HO-C(O)-alquileno C1-6, alquil C1-6-O-C(O)-alquileno C1-6, arilo o heteroarilo, pudiendo estar Ra y Rb eventualmente sustituidos con uno o varios grupos Rc idénticos o diferentes uno de otro; Rc representa un átomo de halogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, cicloalquil C3-7- alquileno C1-6-O-, fluoroalcoxilo C1-6, tioalquilo C1-6, -S(O)-alquilo C1-6, -S(O)2-alquilo C1-6, ciano, C(O)NR1R2, NR1R2, SO2NR1R2, NR3COR4, NR3SO2R5, OC(O)NR1R2, NR3COOR5, NR3CONR1R2, NR3SO2NR1R2, hidroxilo, tiol, oxo, tio, aril-alquileno C1-6, arilo o heteroarilo, estando el arilo y el heteroarilo eventualmente sustituidos con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, fluoroalcoxilo C1-6, nitro o ciano; R1 y R2 representan, independientemente uno de otro, un átomo de hidrogeno o un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, aril-alquileno C1-6, arilo o heteroarilo, estando el arilo y el heteroarilo eventualmente sustituidos con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, fluoroalcoxilo C1-6, nitro o ciano; o R1 y R2 forman conjuntamente, con el átomo de nitrogeno que les lleva, un grupo azetidinilo, pirrolidinilo, piperidinilo, azepinilo, morfolinilo, tiomorfolinilo, piperazinilo, homopiperazinilo, estando este grupo eventualmente sustituido con un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, aril-alquileno C1-6, arilo o heteroarilo, estando el arilo y el heteroarilo eventualmente sustituidos con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, fluoroalcoxilo C1-6, nitro o ciano; R3 y R4 representan, independientemente uno de otro, un átomo de hidrogeno o un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, aril- alquileno C1-6, arilo o heteroarilo, estando el arilo y el heteroarilo eventualmente sustituidos con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1- 6, alcoxilo C1-6, fluoroalcoxilo C1-6, nitro o ciano; o R3 y R4 forman conjuntamente un grupo alquileno C2-6; o R1 y R3 forman conjuntamente un grupo alquileno C2-5; R5 representa un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, aril-alquileno C1-6, arilo o heteroarilo, estando el arilo y el heteroarilo eventualmente sustituidos con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, fluoroalcoxilo C1-6, nitro o ciano; o R3 y R5 forman conjuntamente un grupo alquileno C2-5; R6 representa un átomo de hidrogeno o de halogeno o un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, cicloalcoxilo C3-7, cicloalquil C3-7-alquileno C1-6-O-, fluoroalcoxilo C1-6, tioalquilo C1-6, -S(O)alquilo C1-6, -S(O)2-alquilo C1-6, hidroxilo, tiol, oxo, tio, arilo, aril-alquileno C1-6, heteroarilo, estando el arilo y el heteroarilo eventualmente sustituidos con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, fluoroalcoxilo C1-6, nitro o ciano; R7 representa un átomo de hidrogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, cicloalcoxilo C3-7, cicloalquil C3-7-alquileno C1-6-O-, fluoroalcoxilo C1-6, arilo, aril-alquileno C1-6 o heteroarilo, estando el arilo y el heteroarilo eventualmente sustituidos con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, fluoroalcoxilo C1-6, nitro o ciano; R8, R9 y R10 se definen de tal manera que: dos grupos R8 pueden formar conjuntamente un enlace o un grupo alquileno C1-6; dos grupos R9 pueden formar conjuntamente un enlace o un grupo alquileno C1- 6; R8 y R9 pueden formar conjuntamente un enlace o un grupo alquileno C1-6; R8 y R10 pueden formar conjuntamente un enlace o un grupo alquileno C1-6; R9 y R10 pueden formar conjuntamente un enlace o un grupo alquileno C1-6; R11 representa un átomo de hidrogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, cicloalcoxilo C3-7, cicloalquil C3-7-alquileno C1-6-O-, fluoroalcoxilo C1-6, hidroxilo, alquil C1-6-CO-, COOR5, C(O)NR1R2, aril-alquileno C1-6, arilo o heteroarilo, estando el arilo y el heteroarilo eventualmente sustituidos con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, cicloalcoxilo C3-7, fluoroalcoxilo C1-6, nitro o ciano; R12 representa un átomo de fluor, un grupo alquilo C1-6 eventualmente sustituido con un grupo R13, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, cicloalquil C1-6-1,1-diilo, heterocicloalquil C3-7-1,1-diilo eventualmente sustituido sobre un átomo de nitrogeno con un grupo R11, alcoxilo C1-6, cicloalcoxilo C3-7, cicloalquil C3-7-alquileno C1-6-O-, fluoroalcoxilo C1-6, CO2H, C(O)O-alquilo C1-6, C(O)NR1R2, NR1R2, NR3COR4, OC(O)NR1R2, NR3COOR5, NR3CONR1R2, hidroxilo, tiol, oxo, tio, aril-alquileno C1-6, arilo, estando el arilo eventualmente sustituido con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-6, fluoroalquilo C1-6, alcoxilo C1-6, cicloalcoxilo C3-7, fluoroalcoxilo C1-6, nitro o ciano; R13 representa un grupo alcoxilo C1-6, cicloalcoxilo C3-7, cicloalquil C3-7-alquileno C1-6-O-, C(O)NR1R2, NR1R2, NR3COR4, OC(O)NR1R2, NR3COOR5, hidroxilo; pudiendo estar el o los átomos de nitrogeno del compuesto de la formula general (1) en forma oxidada; en el estado de base o de sal de adicion a un ácido, así como en el estado de hidrato o de solvato. Reivindicacion 11: Un procedimiento de preparacion de un compuesto de la formula (1) de acuerdo con una cualquiera d
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US8716273B2 (en) | 2014-05-06 |
FR2910473A1 (fr) | 2008-06-27 |
JP2010514742A (ja) | 2010-05-06 |
PA8764301A1 (es) | 2008-11-19 |
US20120142669A1 (en) | 2012-06-07 |
US20100041634A1 (en) | 2010-02-18 |
WO2008093024A3 (fr) | 2008-10-02 |
UY30842A1 (es) | 2008-07-31 |
TW200835486A (en) | 2008-09-01 |
JP5284274B2 (ja) | 2013-09-11 |
PE20081549A1 (es) | 2008-12-14 |
EP2125811A2 (fr) | 2009-12-02 |
FR2910473B1 (fr) | 2009-02-13 |
CL2007003826A1 (es) | 2009-01-23 |
EP2125811B1 (fr) | 2013-05-29 |
US20120142670A1 (en) | 2012-06-07 |
US8153650B2 (en) | 2012-04-10 |
WO2008093024A2 (fr) | 2008-08-07 |
US8716272B2 (en) | 2014-05-06 |
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