AR050967A1 - Derivados de bencimidazol utiles como moduladores de los receptores androgenicos (sarms) - Google Patents

Derivados de bencimidazol utiles como moduladores de los receptores androgenicos (sarms)

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AR050967A1
AR050967A1 ARP050104118A ARP050104118A AR050967A1 AR 050967 A1 AR050967 A1 AR 050967A1 AR P050104118 A ARP050104118 A AR P050104118A AR P050104118 A ARP050104118 A AR P050104118A AR 050967 A1 AR050967 A1 AR 050967A1
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alkyl
halogen
substituted
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heteroaryl
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Janssen Pharmaceutica Nv
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Abstract

La presente se refiere a composiciones farmacéuticas que los contienen y su uso en el tratamiento de los trastornos y las afecciones moduladas por el receptor androgénico. Reivindicacion 1: Un compuesto de la formula (1) donde R1 está seleccionado del grupo que consta de H, alquilo C1-4, -alquil C1-4-OH, -alquilo C1-4-CN, -alquilo C1-4-NO2, -alquilo C1-4-N(RARB), -alquilo C1-4-CO2H, -(alquilo C1-4)-X-R7, -CH2-arilo y -CH2-heteroarilo; donde el grupo arilo o heteroarilo (en el grupo -CH2-arilo y -CH2-heteroarilo) está opcionalmente sustituido con uno o más sustituyentes seleccionados, independientemente de halogeno, alquilo C1-4, alquiloC1-4halogeno sustituido, alcoxi C1-4, alcoxi C1-4halogeno sustituido, -alquilo C1-4-CN, -alquilo C1-4- OH, ciano, nitro, amino, alquilamino C1-4, di(alquil C1-4)amino, -S-alquilo C1-4, -S-(alquilo C1-4halogeno sustituido), -SO-alquilo C1-4, -SO2-alquilo C1-4, -O-aralquilo, -C(O)O-alquilo C1-4, -CO2H, -C(O)H, heteroarilo o heterocicloalquilo; donde RA y RB están seleccionados independientemente de H o alquilo C1-4; como alternativa, RA y RB se toman juntos con el átomo de N al cual están ligados para formar una estructura de anillo aromático parcialmente insaturada o saturada de 5 a 7 miembros, que contenga opcionalmente de 1 a 2 heteroátomos adicionales seleccionados de O, S o N; y donde la estructura de anillo está opcionalmente sustituida con alquilo C1-4; donde X está seleccionado del grupo que consiste en -S-, -SO-, -SO2-, -O-SO2-, - O-, -C(OH)-, -C(=N(OH))-, -C(O)-, -C(O)-O-, -NRc-, -NRc-C(O)-, -C(O)-NRc-, -NRc-SO2- y -SO2-NRc-; donde Rc está seleccionado de H o alquilo C1-4; donde R7 está seleccionado del grupo que consta de alquilo C1-4, alquilo C1-4halogeno sustituido, alquenilo C2-4, arilo, aralquilo, bifenilo, cicloalquilo, cicloalquil-(alquilo C1-4)-, heteroarilo, heteroaril-(alquilo C1-4)-, heterocicloalquilo y heterocicloaquil-(alquilo C1-4)-; donde el grupo cicloalquilo, arilo, heteroarilo o heterocicloalquilo, ya sea solo o como parte de un grupo sustituyente, está opcionalmente sustituido con 1 o más sustituyentes seleccionados, independientemente de halogeno, hidroxi, carboxi, alquilo C1-4, alquilo C1-4halogeno sustituido, alcoxi C1- 4, alcoxi C1-4halogeno sustituido, ciano, nitro, amino, alquilamino C1-4, di(alquil C1-4)amino, -S(O)0-2-(alquilo C1-4), -SO2-N(RD)2, arilo, heteroarilo o heterocicloalquilo; donde cada RD está seleccionado independientemente de H o alquilo C1-4; siempre que cuando X sea O o NRc, entonces R6 sea diferente de alquenilo C2-4; R2 está seleccionado del grupo que consta en H, halogeno, alquilo C1-4, alquilo C1-4 halogeno sustituido, ciano, nitro, amino, alquilamino C1-4, di(alquil C1-4)amino, -O- alquilo C1-4, -S-alquilo C1-4, -SO-alquilo C1-4, -SO2-alquilo C1-4 y -NRE-C(O)-alquilo C1-4; donde RE está seleccionado de H o alquilo C1-4; R3 está seleccionado del grupo que consta de H, halogeno, alquilo C1-4, alquilo C1-4 halogeno sustituido, ciano, nitro, amino, alquilamino C1-4, di(alquil C1-4)amino, -O-alquilo C1-4, -S-alquilo C1-4, -SO-alquilo C1-4, -SO2-alquilo C1-4 y -NRF-C(O)-alquilo C1-4; donde RF está seleccionado de H o alquilo C1-4; siempre que por lo meno uno de R2 o R3 sea diferente de H; a es un numero entero de 0 a 1; R10 está seleccionado del grupo que consta en H, halogeno, alquilo C1-4, alquilo C1-4 halogeno sustituido y -O-C(O)-R8; donde R8 está seleccionado del grupo que consta de alquilo C1-4, cicloalquilo, cicloalquil-(alquilo C1-4)-, arilo, aralquilo, heteroarilo, heteroaril-(alquilo C1-4)-, heterocicloalquilo y heterocicloalquil-(alquilo C1-4)-, donde el grupo alquilo, cicloalquilo, arilo, heteroarilo o heterocicloalquilo, ya sea solo o como parte de un grupo sustituyente está opcionalmente sustituido con uno o más sustituyentes seleccionados independientemente de halogeno, hidroxi, carboxi, alquilo C1-4, alquilo C1-4 halogeno sustituido, alcoxi C1-4, alcoxi C1-4 halogeno sustituido, ciano, nitro, amino, alquilamino C1-4 o di(alquil C1-4)amino; R11 está seleccionado del grupo que consta de H y halogeno; como alternativa R10 y R11 se toman juntos con el átomo de C al que están ligados para formar -C(O)-, C=N(OH) o -C=N(O-alquilo C1-4); R12 está seleccionado el grupo que consta de alquilo C1-4, alquilo C1-4 halogeno sustituido, -alquilo C1-4-OH, -alquilo C1-4-CN, -alquilo C1-4-NO2, -alquilo C1-4-N(RGRH), alquilo C1-4-CO2H, -(alquilo C1-4)-Y-R9, -CH2-arilo y -CH2-heteroarilo; donde el arilo o heteroarilo (en el grupo -CH2-arilo o -CH2-heteroarilo) está opcionalmente sustituido con uno o más sustituyentes seleccionados independientemente de halogeno, hidroxi, alquilo C1-4, alquilo C1-4 halogeno sustituido, alcoxi C1-4, alcoxi C1-4 halogeno sustituido, ciano, nitro, amino, alquilamino C1-4, di(alquil C1-4)amino, -S(O)0-2-alquilo C1-4 o -SO2-N(RJ)2; donde cada RJ está seleccionado independientemente de H o alquilo C1-4; donde RG y RH están seleccionados independientemente de H o alquilo C1-4; como alternativa RG y RH se toman juntos con el átomo de N al que están ligados para formar una estructura de anillo aromático parcialmente insaturada o saturada de 5 a 7 miembros, que contenga opcionalmente 1 a 2 heteroátomos adicionales seleccionados de O, S o N; y donde la estructura de anillo está opcionalmente sustituida con alquilo C1-4; donde Y está seleccionada del grupo que consta de -S-, -SO-, SO2-, -O-SO2-, -O-, -C(OH)-, -C(=N(OH))-, -C(O)-, -C(O)-O-, -NRk-, - NRk-C(O)-, -C(O)-NRk-, -NRk-SO2- y -SO2-NRk-; donde Rk está seleccionado de H o alquilo C1-4; donde R9 está seleccionado del grupo que consta de alquilo C1-4, alquilo C1-4 halogeno sustituido, alquenilo C2-4, arilo, aralquilo, bifenilo, cicloalquilo, cicloalquil-(alquilo C1-4)-, heteroarilo, heteroaril-(alquilo C1-4)-, heterocicloalquilo y heterocicloaquil-(alquilo C1-4)-; donde el grupo cicloalquilo, arilo, heteroarilo o heterocicloalquilo, ya sea solo o como parte de un grupo sustituyente, está opcionalmente sustituido con 1 o más sustituyentes seleccionados independientemente de halogeno, hidroxi, carboxi, alquilo C1-4, alquilo C1-4 halogeno sustituido, alcoxi C1-4, alcoxi C1-4 halogeno sustituido, ciano, nitro, amino, alquilamino C1-4, di(alquil C1-4)amino, -S(O)0-2-(alquilo C1-4), -SO2-N(RL)2 o -NRM-C(O)-alquilo C1-4; donde cada RL está seleccionado independientemente de H o alquilo C1-4; y donde RM está seleccionado de H o alquilo C1-4;siempre que cuando Y sea O o NRk, entonces R9 sea diferente de alquenilo C2-4; siempre que cuando R1 es -CH2-fenilo donde l fenilo está sustituido con -C(O)O-alquilo C1-4 o -CO2H; R2 es metilo; a es 0; R10 es H; y R11 es H; entonces R12 sea diferente de -CH2-fenilo; siempre que además cuando R1 es -CH2-fenilo donde el fenilo está sustituido con -C(O)O-alquilo C1-4 o -CO2H; R2 y R3 están seleccionados para ser (H y F),(F y H), (metilo, metilo) o (H y trifluormetilo); a es un numero entero de 0 a 1; R10 es H; y R11 es H; entonces R12 sea diferente de alquilo C1-4; siempre que además cuando R1 es H o alquilo C1-4; a es 0; R10 y R11 se toman juntos con el átomo de C al que están ligados para formar -C(O)-, uno de R2 o R3 es H y el otro de R2 o R3 está seleccionado de halogeno, alquilo C1-4, -O-alquilo C1-4 o nitro, entonces R12 sea diferente de alquilo C1-4, alquilo C1-4 sustituido con un halogeno o bencilo; siempre que además cuando R1 es -CH2-fenilo; a es 0; R120 y R11 se toman juntos con el átomo de C al que están ligados para formar -C(O)-, R2 es H; y R3 es nitro, entonces R12 sea diferente de alquilo C1-4; siempre que además cuando R1 es H; a es 0; R2 es -O-alquilo C1-4; R3 es -O-alquilo C1-4; y R10 y R11 se toman juntos con el átomo de C al que están ligados para formar -C(O)-; entonces R12 sea diferente de bencilo; siempre que además R1 es -alquilo C1-4-N-(alquilo C1-4)2; a es 0; R2 es -O-alquilo C1-4; R3 es -O-alquilo C1-4; y R10 y R11 se toman juntos con el átomo de C al que están ligados para formar -C(O)-, entonces R12 sea diferente de bencilo, donde el bencilo está sustituido con un halogeno; o una sal farmacéuticamente aceptable del mismo.
ARP050104118A 2004-09-30 2005-09-29 Derivados de bencimidazol utiles como moduladores de los receptores androgenicos (sarms) AR050967A1 (es)

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CA2582347A1 (en) 2006-04-13
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US7348438B2 (en) 2008-03-25
WO2006039215A2 (en) 2006-04-13
AU2005292317A1 (en) 2006-04-13
EP1812406A2 (en) 2007-08-01
CN101133036A (zh) 2008-02-27
US20100298383A1 (en) 2010-11-25
AU2005292317B2 (en) 2011-09-08
CA2582347C (en) 2014-09-23
US20080119522A1 (en) 2008-05-22
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