CO5271658A1 - Antagonistas del factor liberador de corticotropina - Google Patents
Antagonistas del factor liberador de corticotropinaInfo
- Publication number
- CO5271658A1 CO5271658A1 CO01003117A CO01003117A CO5271658A1 CO 5271658 A1 CO5271658 A1 CO 5271658A1 CO 01003117 A CO01003117 A CO 01003117A CO 01003117 A CO01003117 A CO 01003117A CO 5271658 A1 CO5271658 A1 CO 5271658A1
- Authority
- CO
- Colombia
- Prior art keywords
- alkyl
- cycloalkyl
- alkylene
- cycloalkylene
- heterocycloalkyl
- Prior art date
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
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Abstract
Un compuesto de la fórmula <EMI FILE="01003117_1" ID="1" IMF=JPEG >o una de sus sales farmacéuticamente aceptables, donde las líneas de puntos representan dobles enlaces opcionales, con la condición de que cuando la línea de puntos en C --- G representa un doble enlace entonces la línea de puntos en N(R6) --- C no representa un doble enlace; y con la condición de que cuando la línea de puntos en N(R6) --- C representa un doble enlace, R6 está ausente de la fórmula III y la línea de puntos en C --- G no representa un doble enlace; A es -CR7 o N; B es -NR1R2, CR1R2R11, -C(=CR2R12)R1, -NHCHR1R2. -OCHR1R2, -SCHR1R2, -CHR2OR1, -CHR1OR2, -CHR2SR1, -C(S)R2, -C(O)R2, -CHR2NR1R2, -CHR1NHR2, -CHR1N(CH3)R2, o -NR12NR1R2; cuando la línea de puntos en C --- G representa un doble enlace, entonces G es hidrógeno, oxígeno, azufre, NH o N(alquilo C1-C4); cuando la línea de puntos en C --- G no representa un doble enlace, entonces es -C(H)(NH2), CH2, -C(H)(metoxi), -C(H)(etoxi), -C(H)(O(alquilo C3-C4)), -C(H)(halo), -C(H)(trifluorometoxi), -C(H)(metilo), -C(H)(etilo), -C(H)(alquilo C3-C4), -C(H)(S(alquilo C1-C4)), C(alquilo C1-C4)(alquilo C1-C4), ciclopropilo, -C(H)(ciclopropilo), tiometoxi, -C(H)(NH2), -C(H)(NHCH3), -C(H)(N(CH3)2) o -C(H)(trifluorometilo); donde dichos grupos ciclopropilo, metoxi, etoxi, alquilo C3-C4 y alquilo C1-C4 de C --- G pueden estar opcionalmente sustituidos con un OH, metoxi, o trifluorometoxi, o pueden estar opcionalmente sustituidos con uno a seis átomos de flúor; Y es CH o N; Z es NH, O, S, -N(alquilo C1-C2), -NC(O)CF3, o -C(R13R14), donde R13 y R14 son cada uno, independientemente, hidrógeno, trifluorometilo o metilo, o uno de R13 y R14 es ciano y el otro es hidrógeno o metilo, o -C(R13R14) es un - 2 -grupo ciclopropilo, o Z es nitrógeno o CH y forma un anillo heterocíclico de cinco o seis miembros condensado con R5, cuyo anillo comprende opcionalmente dos o tres miembros heterólogos adicionales seleccionados independientemente entre oxígeno, nitrógeno, NR12, y S(O)m, y opcionalmente comprende de uno a tres dobles enlaces, y está opcionalmente sustituido con halo, alquilo C1-C4, -O(alquilo C1-C4), NH2, NHCH3, N(CH3)2, CF3, o OCF3, con la condición de que dicho anillo no contiene ninguno de los enlaces -S-S-, -S-O-, -N-S-, o OO, y no comprende más de dos miembros heterológos oxígeno o S(O)m; R1 es C(O)H, C(O)(alquilo C1-C6), C(O)(alquileno C1-C6)(cicloalquilo C3-C8), C(O)(ciclo alquileno C3-C8)(cicloalquilo C3-C8), C(O)(alquileno C1-C6)(heterocicloalquilo C4-C8), -C(O)(cicloalquileno C3-C8)(heterocicloalquilo C4-C8), -alquilo C1-C6, cicloalquilo C3-C8, heterocicloalquilo C4-C8, -(alquileno C1-C6)(cicloalquilo C3-C8), -(cicloalquileno C3-C8)(cicloalquilo C3-C8), -(alquileno C1-C6)(heterocicloalquilo C4-C8), -(cicloalquileno C3-C8)(heterocicloalquilo C4-C8), o -O-arilo, o -O-(alquileno C1-C6)-arilo; donde dichos grupos arilo, heterocicloalquilo C4-C8, alquilo C1-C6, cicloalquilo C3-C8, cicloalquileno C3-C8, y alquileno C1-C6 pueden estar cada uno, independientemente, opcionalmente sustituidos con uno a seis flúor y pueden estar cada uno, independientemente. opcionalmente sustituidos con uno o dos sustituyentes R8 independientemente seleccionados del grupo constituido por alquilo C1-C4, -cicloalquilo C3-C8, hidroxi, cloro, bromo, yodo, CF3, -O-(alquilo C1-C6), -O-(cicloalquilo C3-C5), -O-CO-(alquilo C1-C4), -O-CO-NH(alquilo C1-C4), -O-CO-N(R24)(R25), -N(R24)(R25), -S(alquilo C1-C4), -S(cicloalquilo C3-C5), N(alquilo C1-C4)CO(alquilo C1-C4), -NHCO(alquilo C1-C4), -COO(alquilo C1-C4), CONH-(alquilo C1-C4), -CON(alquilo C1-C4)(alquilo C1-C2), CN, NO2, -OSO2(alquilo C1-C4), S (alquilo C1-C6)(alquilo C1-C2)l-, -SO(alquilo C1-C4) y -SO2(alquilo C1-C4); y donde los restos alquilo C1-C6, alquileno C1-C6, cicloalquilo C5-C8, cicloalquileno C5-C8, y heterocicloalquilo C5-C8 de R1 pueden contener independientemente opcionalmente de uno a tres dobles o triples enlaces; y donde los restos alquilo C1-C4 y los restos alquilo C1-C6 de R8 pueden estar independientemente opcionalmente sustituidos con hidroxi, amino, alquilo C1-C4, arilo, -CH2-arilo, cicloalquilo C3-C5, o -O-(alquilo C1-C4), y pueden estar independientemente opcionalmente sustituidos con uno a seis flúor, y pueden contener opcionalmente uno o dos dobles o triples enlaces; y donde cada uno de los grupos heterocicloalquilo de R1 contiene de uno a tres restos heterólogos seleccionados entre oxígeno, S(O)m, nitrógeno, y NR12; R2 es hidrógeno, alquilo C1-C12, cicloalquilo C3-C8, heterocicloalquilo C4-C8, -(alquileno C1-C6)(cicloalquilo C3-C8), -(cicloalquileno C3-C8)(cicloalquilo C3-C8), -(alquileno C1-C6)(heterocicloalquilo C4-C8), -(cicloalquileno C3-C8)(heterocicloalquilo C4-C8), arilo, -(alquileno C1-C6)arilo, o -(cicloalquileno C3-C8)(arilo); donde cada uno de los grupos R2 anteriores puede estar opcionalmente sustituido con uno a tres sustituyentes independientemente seleccionados entre cloro, flúor, y alquilo C1-C6, donde uno de dichos uno a tres sustituyentes puede ser seleccionado adicionalmente entre bromo, yodo, alcoxi C1-C6, -OH, -O-CO-(alquilo C1-C6), -O-CO-N(alquilo C1-C4)(alquilo C1-C2), -S(alquilo C1-C6), -S(O)(alquilo C1-C6), -S(O)2(alquilo C1-C6), S (alquilo C1-C6)(alquilo C1-C2)l-, CN, y NO2; y donde los restos alquilo C1-C12, -(alquileno C1-C6), -(cicloalquilo C5-C8), -(cicloalquileno C5-C8), y -(heterocicloalquilo C5-C8) de R2 pueden contener independientemente opcionalmente de uno a tres dobles o triples enlaces; y donde cada uno de los grupos heterocicloalquilo de R2 contiene de uno a tres restos heterólogos seleccionados entre oxígeno, S(O)m, nitrógeno, y NR12; o cuando R1 y R2 están como en -NHCHR1R2, -OCHR1R2, -SCHR1R2, -CHR1R2 o -NR1R2, R1 y R2 de B pueden formar un anillo saturado de 5 a 8 miembros que puede contener opcionalmente uno o dos dobles enlaces y en el cual uno o dos de los carbonos del anillo puede estar opcionalmente reemplazado por un oxígeno, S(O)m, nitrógeno o NR12; y cuyo anillo carbocíclico puede estar opcionalmente sustituido con 1 a 3 sustituyentes seleccionados del grupo constituido por hidroxi, alquilo C1-C4, flúor, cloro, bromo, yodo, CF3, -O-(alquilo C1-C4), -O-CO-(alquilo C1-C4), -O-CO-NH(alquilo C1-C4), -O-CO-N(alquilo C1-C4)(alquilo C1-C2), -NH(alquilo C1-C4), -N(alquilo C1-C2)(alquilo C1-C4), -S(alquilo C1-C4), -N(alquilo C1-C4)CO(alquilo C1-C4), -NHCO(alquilo C1-C4), -COO(alquilo C1-C4), -CONH(alquilo C1-C4), -CON(alquilo C1-C4)(alquilo C1-C2), CN, NO2, -OSO2(alquilo C1-C4), -SO(alquilo C1-C4) y -SO2(alquilo C1-C4) donde uno de dichos uno a tres sustituyentes puede ser adicionalmente seleccionado de fenilo; R3 es metilo, etilo, flúor, cloro, bromo, yodo, ciano, metoxi, OCF3, NH2, NH(alquilo C1-C2), N(CH3)2, -NHCOCF3, -NHCH2CF3, S(O)m(alquilo C1-C4), CONH2, -CONHCH3, CON(CH3)2, -CF3, o CH2OCH3;R4 es hidrógeno, alquilo C1-C4, cicloalquilo C3-C5, -(alquileno C1-C4)(cicloalquilo C3-C5), -(cicloalquileno C3-C5)(cicloalquilo C3-C5), ciano, flúor, cloro, bromo, yodo, -OR24, alcoxi C1-C6, -O-(cicloalquilo C3-C5), -O-(alquileno C1-C4)(cicloalquilo C3-C5), - 3 --O-(cicloalquileno C3-C5)(cicloalquilo C3-C5), -CH2SC(S)O(alquilo C1-C4), -CH2OCF3, -CF3, amino, nitro, -NR24R25, -(alquileno C1-C4)-OR24, -(alquileno C1-C4)Cl, -(alquileno C1-C4)NR24R25-NHCOR24, -NHCONR24R25, -C=NOR24, -NHNR24R25, -S(O)mR24, C(O)R24, -OC(O)R24, -C(O)CN, C(O)NR24R25, -C(O)NHNR24R25, y -COOR24, donde los grupos alquilo y alquileno de R4 pueden contener independientemente opcionalmente uno o dos dobles o triples enlaces y pueden estar independientemente opcionalmente sustituidos con uno o dos sustituyentes R10 independientemente seleccionados entre hidroxi, amino, -NHCOCH3, -NHCOCH2Cl, -NH(alquilo C1-C2), -N(alquilo C1-C2)(alquilo C1-C2), -COO(alquilo C1-C4), -COOH, -CO(alquilo C1-C4), alcoxi C1-C6, tioalquilo C1-C3, ciano y nitro, y con uno a cuatro sustituyentes seleccionados independientemente entre flúor y cloro; R5 es arilo o heteroarilo y está sustituido con uno a cuatro sustituyentes R27 indepen dientemente seleccionados entre halo, alquilo C1-C10, -(alquileno C1-C4)(cicloalquilo C3-C8), -(alquileno C1-C4)(heterocicloalquilo C4-C8), -(cicloalquilo C3-C8), -(heterocicloalquilo C4-C8), -(cicloalquileno C3-C8), -(cicloalquilo C3-C8), -(cicloalquileno C3-C8) (heterocicloalquilo C4-C8), haloalquilo C1-C4, haloalcoxi C1-C4, nitro, ciano, -NR24R25, -NR24COR25, -NR24CO2R26, -COR24, -OR25, -CONR24R25, -CO(NOR22)R23, -CO2R26, -C=N(OR22)R23, y -S(O)mR23; donde dichos grupos alquilo C1-C10, cicloalquilo C3-C8, (alquileno C1-C4), (cicloalquilo C3-C8), (cicloalquileno C3-C8), y (heterocicloalquilo C4-C8) pueden estar opcionalmente sustituidos con uno a tres sustituyentes independientemente seleccionados entre alquilo C1-C4, cicloalquilo C3-C8, (alquileno C1-C4) (cicloalquilo C3-C8), -(cicloalquileno C3-C8)(cicloalquillo C3-C8), haloalquilo C1-C4, hidroxi, alcoxi C1-C6, nitro, halo, ciano, -NR24R25, -NR24COR25, NR24CO2R26, -COR24, -OR25, -CONR24R25, CO2R26, -CON(OR22)R25, y -S(O)mR23; y donde dos sustituyentes adyacentes del grupo R5 pueden formar opcionalmente un anillo de 5-7 miembros, saturado o insaturado, condensado con R5, cuyo anillo puede contener opcionalmente uno, dos, o tres miembros heterólogos independientemente seleccionados entre O,S(O)m, y N, pero ninguno de los enlaces -S-S-, -O-O-, -S-O-, o -N-S-, y cuyo anillo está opcionalmente sustituido con alquilo C1-C4, cicloalquilo C3-C8, -(alquileno C1-C4) (cicloalquilo C3-C8), -(cicloalquileno C3-C8)(cicloalquilo C3-C8), haloalquilo C1-C4, nitro, halo, ciano, -NR24R25, NR24COR25, NR24CO2R26, -COR24, -OR25, -CONR24R25, CO2R26, -CON(OR26)R25, o -S(O)mR23; donde uno de dichos uno a cuatro sustituyentes opcionales R27 puede ser adicionalmente seleccionado entre -SO2NH(alquilo C1-C4), -SO2NH(alquileno C1-C4)(cicloalquilo C3-C8), -SO2NH(cicloalquilo C3-C8), -SO2NH(cicloalquileno C3-C8)(cicloalquilo C3-C8), -SO2N(alquilo C1-C4)(alquilo C1-C2), -SO2NH2, -NHSO2(alquilo C1-C4), -NHSO
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