AR074691A1 - Derivados de tiazol como ligandos de receptores de cannabinoides - Google Patents

Derivados de tiazol como ligandos de receptores de cannabinoides

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AR074691A1
AR074691A1 ARP090104914A ARP090104914A AR074691A1 AR 074691 A1 AR074691 A1 AR 074691A1 AR P090104914 A ARP090104914 A AR P090104914A AR P090104914 A ARP090104914 A AR P090104914A AR 074691 A1 AR074691 A1 AR 074691A1
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cr1cr1d
alkyl
haloalkyl
orf
case
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Michael J Dart
Jennifer M Frost
William A Carroll
Tongmei Li
Steven P Latshaw
Teodozyj Kolasa
Xueqing Wang
Sridhar Peddi
Bo Lui
Meena Patel
Derek W Nelson
Arturo Perez-Medrano
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Abbott Lab
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
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    • C07D277/38—Nitrogen atoms
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    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

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Abstract

Composiciones que comprenden dichos compuestos y métodos para tratar condiciones y trastornos usando dichos compuestos y composiciones. Reivindicación 1: Un compuesto caracterizado porque responde a la fórmula (1), o una sal, solvato o sal de un solvato aceptable farmacéuticamente del mismo, donde L1 es O, S, S(O), S(O)2, o N(Rbx); donde Rbx es hidrógeno, alquilo, haloalquilo, alcoxialquilo, -C(O)O(alquilo), cicloalquilo monocíclico, -(CR1cR1d)q3- (cicloalquilo monocíclico), o haloalcoxialquilo; y A1 es -G1a-G1b, -(CR1aR1b)q1-G1c; -G1e, -(CR1aR1b)q1-A2, -N(Rb)C(O)Ra, -N(Rb)C(O)ORd, -N(Rb)C(O)N(Rb)(Rc), -N(Rb)(Rc), o -N=C(Rp)(Rq); o L1 y A1 juntos son N=N(Rcx); donde Rcx es alquilo, haloalquilo, -(CR1aR1b)q3-A3, G1d, o -(CR1aR1b)q3-G1d; Rp es hidrógeno, alquilo, haloalquilo, -(CR1aR1b)q3-A3, -C(O)ORd, -C(O)Rd, G1d, o -(CR1aR1b)q3-G1d; Rq es hidrógeno, alquilo, haloalquilo, -N(Rb)(Rc), -(CR1aR1b)q3-A3, G1d, o -(CR1aR1b)q3-G1d; o Rp y Rq, junto con el átomo de carbono al cual se encuentran unidos, forman un anillo de 5, 6, 7 u 8 miembros seleccionado entre el grupo que consiste en cicloalquilo monocíclico y heterociclo monocíclico, opcionalmente sustituido con 1, 2, 3, 4, o 5 sustituyentes seleccionados independientemente entre el grupo que consiste en oxo, alquilo, haloalquilo, y halógeno; A2 es -C(O)Ra, -S(O)2Rd, -C(O)N(Rb)Rc), -C(S)N(Rb)(Rc), -S(O)2N(Rb)(Rc), -C(=NORf)Ra, -CN, -N(Rc)C(O)Ra, -N(Rc)C(O)ORd, -N(Rc)S(O)2Rd, -N(Rc)C(O)N(Rb)(Rc), -N(Rc)S(O)2N(Rb)(Rc), -N(Rb)(Rc), -O-Rj, o -O-C(O)(alquilo); Ra y Rc, en cada caso, son independientemente entre sí hidrógeno, alquilo, haloalquilo, -(CR1aR1b)q2-A3, G1d, o -(CR1aR1b)q2-G1d; Rb, en cada caso, es independientemente hidrógeno, alquilo, haloalquilo, alcoxialquilo, cicloalquilo monocíclico, -(CR1cR1d)q2-(cicloalquilo monocíclico), o haloalcoxialquilo; Rd en cada caso, es independientemente alquilo, haloalquilo, -(CR1aR1b)q2-A3, G1d, o -(CR1aR1b)q2-G1d; Rj es hidrógeno, haloalquilo, -(CR1aR1b)q2-A3, G1d, o -(CR1aR1b)q2-G1d; A3 es C(O)Rh, -S(O)2Re, -C(O)N(Rh)2, -C(S)N(Rh)2, -S(O)2N(Rh)2, -C(=NORh)Rh, -N(Rh)C(O)Rh, -N(Rh)C(O)ORe, -N(Rh)S(O)2Re, -N(Rh)C(O)N(Rh)2, -N(Rh)S(O)2N(Rh)2, -CN, -ORh, o -N(Rh)2; G1a, G1b, y G1c, en cada caso, son independientemente entre sí cicloalquilo, cicloalquenilo, heterociclo, arilo, o heteroarilo; G1e es cicloalquilo, heterociclo, o heteroarilo; donde el anillo según se lo representa mediante G1a se sustituye opcionalmente con 1, 2, 3, 4 o 5 sustituyentes seleccionados independientemente entre el grupo que consiste en alquilo, alquenilo, alquinilo, halógeno, haloalquilo, =N-CN, =N-ORf, -CN, oxo, -ORf, -OC(O)Rf, -OC(O)N(Rf)2, -S(O)2Re, -S(O)2N(Rf)2, -C(O)Rf, -C(O)ORf, -C(O)N(Rf)2, -N(Rf)2, -N(Rf)C(O)Rf, -N(Rf)S(O)2Re, -N(Rf)C(O)O(Re), -N(Rf)C(O)N(Rf)2, -(CR1cR1d)q3-ORf, -(CR1cR1d)q3-OC(O)Rf, -(CR1cR1d)q3-OC(O)N(Rf)2, -(CR1cR1d)q3-S(O)2Re, -(CR1cR1d)q3-S(O)2N(Rf)2, -(CR1cR1d)q3-C(O)Rf, -(CR1cR1d)q3-C(O)ORf, -(CR1cR1d)q3-C(O)N(Rf)2, -(CR1cR1d)q3-N(Rf)2, -(CR1cR1d)q3-N(Rf)C(O)Rf, -(CR1cR1d)q3-N(Rf)S(O)2Re, -(CR1cR1d)q3-N(Rf)C(O)O(Re), -(CR1cR1d)q3-N(Rf)C(O)N(Rf)2 y -(CR1cR1d)q3-CN; donde los anillos según se los representa mediante G1b y G1c se sustituye cada uno opcionalmente con 1, 2, 3, 4, o 5 sustituyentes seleccionados independientemente entre el grupo que consiste en -G1d, -(CR1cR1d)q3-G1d, alquilo, alquenilo, alquinilo, halógeno, haloalquilo, =N-CN, =N-ORf , -CN, oxo, -ORf, -OC(O)Rf, -OC(O)N(Rf)2, -S(O)2Re, -S(O)2N(Rf)2, -C(O)Rf, -C(O)ORf, -C(O)N(Rf)2, -N(Rf)2, -N(Rf)C(O)Rf, -N(Rf)S(O)2Re, -N(Rf)C(O)O(Re), -N(Rf)C(O)N(Rf)2, -(CR1cR1d)q3-ORf, -(CR1cR1d)q3-OC(O)Rf, -(CR1cR1d)q3-OC(O)N(Rf)2, -(CR1cR1d)q3-S(O)2Re, -(CR1cR1d)q3-S(O)2N(Rf)2, -(CR1cR1d)q3-C(O)Rf, -(CR1cR1d)q3-C(O)ORf, -(CR1cR1d)q3-C(O)N(Rf)2, -(CR1cR1d)q3-N(Rf)2, -(CR1cR1d)q3-N(Rf)C(O)Rf, -(CR1cR1d)q3-N(Rf)S(O)2Re, -(CR1cR1d)q3-N(Rf)C(O)O(Re), -(CR1cR1d)q3-N(Rf)C(O)N(Rf)2 y -(CR1cR1d)q3-CN; donde el anillo según se lo representa mediante G1e se sustituye opcionalmente con 1, 2, 3, 4, o 5 sustituyentes seleccionados independientemente entre el grupo que consiste en -(CR1cR1d)q3-G1d, alquilo, alquenilo. alquinilo, halógeno, haloalquilo, =N-CN, =N-ORf , -CN, oxo, -ORf, -OC(O)Rf, -OC(O)N(Rf)2, -S(O)2Re, -S(O)2N(Rf)2, -C(O)Rf, -C(O)ORf, -C(O)N(Rf)2, -N(Rf)2, -N(Rf)C(O)Rf, -N(Rf)S(O)2Re, -N(Rf)C(O)O(Re), -N(Rf)C(O)N(Rf)2, -(CR1cR1d)q3-ORf, -(CR1cR1d)q3-OC(O)Rf, -(CR1cR1d)q3-OC(O)N(Rf)2, -(CR1cR1d)q3-S(O)2Re, -(CR1cR1d)q3-S(O)2N(Rf)2, -(CR1cR1d)q3-C(O)Rf, -(CR1cR1d)q3-C(O)ORf, -(CR1cR1d)q3-C(O)N(Rf)2, -(CR1cR1d)q3-N(Rf)2, -(CR1cR1d)q3-N(Rf)C(O)Rf, -(CR1cR1d)q3-N(Rf)S(O)2Re, -(CR1cR1d)q3-N(Rf)C(O)O(Re), -(CR1cR1d)q3-N(Rf)C(O)N(Rf)2 y -(CR1cR1d)q3-CN; G1d, en cada caso, es independientemente un heterociclo monocíclico, un heteroarilo monocíclico, un fenilo, un cicloalquilo monocíclico, o un cicloalquenilo monocíclico; cada uno de los cuales se sustituye opcionalmente con 1, 2, 3, o 4 sustituyentes seleccionados independientemente entre el grupo que consiste en -N(Rh)2, -CN, oxo, alquilo, haloalquilo, alcoxi, haloalcoxi, halógeno, y hidroxi; Re y Ri, en cada caso, son independientemente entre si alquilo C1-4, haloalquilo C1-4, cicloalquilo monocíclico, o -(CR1cR1d)q3-(cicloalquilo monocíclico); Rf en cada caso, es independientemente hidrógeno, alquilo C1-4, haloalquilo C1-4, -(CR1cR1d)q3-ORg, cicloalquilo monocíclico, o -(CR1cR1d)q3-(cicloalquilo monocíclico); Rg y Rh, en cada caso, son independientemente entre sí hidrógeno, alquilo C1-4, haloalquilo C1-4, cicloalquilo monocíclico, o -(CR1cR1d)q3-(cicloalquilo monocíclico); donde el cicloalquilo monocíclico, como un sustituyente o parte de un sustituyente, de Rbx, Rb, Re, Ri, Rf, Rg, y Rh, en cada caso, independientemente no se sustituye o se sustituye con 1, 2, 3, o 4 sustituyentes seleccionados independientemente entre el grupo que consiste en alquilo C1-4, halógeno, oxo, hidroxi, alcoxi, C1-4, haloalcoxi C1-4, y haloalquilo C1-4; R2 es alquilo C2-10, alquenilo, alquinilo, haloalquilo, -(CR2aR2b)q4-O-haloalquilo, -(CR2aR2b)q4-O-G2a, -(CR2aR2b)q4-O-(CR2cR2d)q5-G2a, -(CR2aR2b)q5-C(O)-Ra, -(CR2aR2b)q5-C(=N-ORe)Ra, -(CR2aR2b)q5-SO2-Rd, -(CR2aR2b)q5-G2b, -(CR2aR2b)q5-C(O)N(Rb)(Rc), -(CR2aR2b)q4-OC(O)N(Rb)(Rc), o -(CR2aR2b)q5-CN; G2a, en cada caso, es independientemente cicloalquilo, cicloalquenilo, heterociclo, arilo, o heteroarilo; G2b es cicloalquilo, cicloalquenilo, tien-2-ilo, o tien-3-ilo, donde los anillos según se los representa mediante G2a y G2b se sustituye cada uno opcionalmente con 1, 2, 3, 4, o 5 sustituyentes seleccionados independientemente entre el grupo que consiste en oxo, alquilo, halógeno, hidroxi, alcoxi, haloalcoxi, y haloalquilo; R3 y R4 son iguales o diferentes, y son independientemente entre sí G3, hidrógeno, alquilo, alquenilo, alquinilo, -NO2, -CN, halógeno, -ORh, -N(Rh)2, -C(O)Rh, -C(O)O(Rh), haloalquilo, -(CR3aR3b)q6-ORh, -(CR3aR3b)q6-N(Rh)2, -(CR3aR3b)q6-C(O)Rh, o -(CR3aR3b)q6-C(O)O(Rh); o R3 y R4, junto con los átomos de carbono a los cuales se encuentran unidos, forman un anillo monocíclico de 4, 5, 6 o 7 miembros que contiene cero, una, o dos uniones dobles adicionales, que contiene opcionalmente uno o dos átomos de nitrógeno como átomos del anillo, dos átomos no adyacentes del anillo monocíclico se unen opcionalmente mediante un puente alquenileno de 2, 3, o 4 átomos de carbono, o se unen opcionalmente mediante un puente alquileno de 1, 2, 3, o 4 átomos de carbono, el anillo monocíclico no se sustituye o se sustituye con 1, 2, 3, 4, o 5 sustituyentes seleccionados independientemente entre el grupo que consiste en oxo, alquilo, halógeno, hidroxi, alcoxi, haloalcoxi, y haloalquilo; dos sustituyentes sobre el mismo átomo de carbono de dicho anillo monocíclico, junto con el átomo de carbono al cual se encuentran unidos, forman opcionalmente un anillo cicloalquilo monocíclico de 3, 4, 5 o 6 miembros, donde el anillo cicloalquilo monocíclico se sustituye opcionalmente con 1, 2, 3, 4, 5, o 6 sustituyentes seleccionados independientemente entre el grupo que consiste en alquilo y haloalquilo; G3 es cicloalquilo, cicloalquenilo, arilo, heterociclo, o heteroarilo, cada uno de los cuales no se sustituye o se sustituye independientemente con 1, 2, 3, o 4 sustituyentes seleccionados independientemente entre el grupo que consiste en alquilo C1-4, alquenilo C2-4, alquinilo C2-4, halógeno, haloalquilo C1-4, =N-CN, =N-ORh, -CN, oxo, -ORh, -OC(O)Rh, -OC(O)N(Rh)2, -S(O)2Ri, -S(O)2N(Rh)2, -C(O)Rh, -C(O)ORh, -C(O)N(Rh)2, -N(Rh)2, -N(Rh)C(O)Rh, -N(Rh)S(O)2Ri, -N(Rh)C(O)O(Ri), y -N(Rh)C(O)N(Rh)2; R1a, R1c, R1d, R2a, R2b, R2c, R2d, R3a, y R3b, en cada caso, son independientemente entre sí hidrógeno, halógeno, alquilo C1-4, o haloalquilo C1-4; R1b, en cada caso, es independientemente hidrógeno, halógeno, alquilo C1-4, haloalquilo C1-4, -ORh, -N(Rh)2, -N(Rh)C(O)Rh, -N(Rh)C(O)ORe, o -N(Rh)S(O)2Re; R1g, en cada caso, es independientemente G1d, alquilo C1-4, alquenilo C2-4, alquinilo C2-4, halógeno, haloalquilo C1-4, -CN, -ORf, OC(O)Rf, -OC(O)N(Rf)2, -S(O)2Re, -S(O)2N(Rf)2, -C(O)Rf, -C(O)ORf, -C(O)N(Rf)2, -N(Rf)2, -N(Rf)C(O)Rf, -N(Rf)S(O)2Re, -N(Rf)C(O)O(Re), -N(Rf)C(O)N(Rf)2, -(CR1cR1d)q3-ORf, -(CR1cR1d)q3-OC(O)Rf, -(CR1cR1d)q3-OC(O)N(Rf)2, -(CR1cR1d)q3-S(O)2Re, -(CR1cR1d)q3-S(O)2N(Rf)2, -(CR1cR1d)q3-C(O)Rf, -(CR1cR1d)q3-C(O)ORf, -(CR1cR1d)q3-C(O)N(Rf)2, -(CR1cR1d)q3-N(Rf)2, -(CR1cR1d)q3-N(Rf)C(O)Rf, -(CR1cR1d)q3-N(Rf)S(O)2Re, -(CR1cR1d)q3-N(Rf)C(O)O(Re), -(CR1cR1d)q3-N(Rf)C(O)N(Rf)2 o -(CR1cR1d)q3-CN; q1 y q2, en cada caso, son independientemente entre sí 1, 2. 3, o 4; q3, en cada caso, es independientemente 1, 2 o, 3; q4, en cada caso, es independientemente 2, 3, 4, o 5; q5 y q6, en cada caso, son independientemente entre sí 1, 2, 3, 4, 5, o 6; y z es 0, 1, 2, 3, o 4; con la condición de que cuando L1 es N(Rbx) donde Rbx es hidrógeno, alquilo, o alcoxialquilo; y R2 alquilo C2-10, alquenilo, alquinilo, haloalquilo, -(CR2aR2b)q5-C(O)-Ra donde Ra es heterociclo, -(CR2aR2b)q5-C(O)N(Rb)(Rc) donde Rb y Rc son hidrógeno o alquilo, -
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