AR043052A1 - Tiadiazoldioxidos y tiadiazoloxidos como ligandos del receptor de cxc- y cc-quimiocina; composiciones farmaceuticas que los contienen y su uso en la preparacion de medicamentos - Google Patents

Tiadiazoldioxidos y tiadiazoloxidos como ligandos del receptor de cxc- y cc-quimiocina; composiciones farmaceuticas que los contienen y su uso en la preparacion de medicamentos

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Publication number
AR043052A1
AR043052A1 ARP030103663A ARP030103663A AR043052A1 AR 043052 A1 AR043052 A1 AR 043052A1 AR P030103663 A ARP030103663 A AR P030103663A AR P030103663 A ARP030103663 A AR P030103663A AR 043052 A1 AR043052 A1 AR 043052A1
Authority
AR
Argentina
Prior art keywords
substituted
group
unsubstituted
alkyl
independently selected
Prior art date
Application number
ARP030103663A
Other languages
English (en)
Original Assignee
Pharmacopeia Drug Discovery
Schering Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Pharmacopeia Drug Discovery, Schering Corp filed Critical Pharmacopeia Drug Discovery
Publication of AR043052A1 publication Critical patent/AR043052A1/es

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    • C07—ORGANIC CHEMISTRY
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    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
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Abstract

Uso del compuesto para la preparación de un medicamento útil en el tratamiento de una enfermedad mediada por quimiocinas, como, cáncer, angiogénesis, enfermedad angiogénica ocular, enfermedades pulmonares, esclerosis múltiple, artritis reumatoidea, osteopatía degenerativa, infarto y lesión por reperfusión cardíaca, dolor agudo, dolor por inflamación aguda y crónica y dolor neuropático usando un compuesto de la fórmula (1). Reivindicación 1: Un compuesto de la fórmula (1) y sus sales aceptables para uso farmacéutico y sus solvatos, donde: A se selecciona entre los radicales de los grupos de fórmulas (2) y (3), donde los anillos de estos grupos A están sustituidos con 1 a 6 sustituyentes seleccionados, cada uno en forma independiente, del grupo formado por: grupos R9; los radicales del grupo de fórmulas (4), donde uno o ambos anillos de los anillos de estos grupos A están sustituidos con 1 a 6 sustituyentes seleccionados, cada uno en forma independiente, del grupo formado por: grupos R9; los radicales del grupo de fórmulas (5), donde los anillos de fenilo de estos grupos A están sustituidos con 1 a 3 sustituyentes seleccionados, cada uno en forma independiente, del grupo formado por: grupos R9; y los radicales del grupo de fórmulas (6); B se selecciona entre los radicales del grupo de fórmulas (7); n es 0 a 6; p es 1 a 5; X es O, NR18, ó S; Z es 1 a 3; R2 se selecciona del grupo formado por: hidrógeno, OH, -C(O)OH, -SH, -SO2NR13R14, -NHC(O)R13, -NHSO2NR73R14, -NHSO2R13, -NR13R14, -C(O)NR13R14, -C(O)NHOR13, -C(O)NR13OH, -S(O2)OH, -OC(O)R13, un grupo funcional ácido heterocíclico no sustituido, y un grupo funcional ácido heterocíclico sustituido; donde hay 1 a 6 sustituyentes en dicho grupo funcional ácido heterocíclico sustituido cada sustituyente se selecciona en forma independiente del grupo formado por: grupo R9; cada R3 y R4 se selecciona en forma independiente del grupo formado por: hidrógeno, ciano, halógeno, alquilo, alcoxi, cicloalquilo sustituido con 1 a 4 grupos alquilo donde cada grupo alquilo se selecciona en forma independiente, cicloalquilo no sustituido, cicloalquilo sustituido con 1 a 4 grupos alquilo, -OH, -CF3, -OCF3, -NO2, -C(O)R13, -C(O)OR13, -C(O)NHR17, -C(O)NR13R14, -SO(t)NR13R14, -SO(t)R13, -C(O)NR13OR14, arilo sustituido ó no sustituido, heteroarilo sustituido ó no sustituido, -P(O)R31R31, -C(NR30)NR13R14 y -C(NOR13)R14, donde hay 1 a 6 sustituyentes en dicho grupo arilo sustituido y cada sustituyente se selecciona en forma independiente del grupo formado por: grupos R9; y donde hay 1 a 6 sustituyentes en dicho grupo heteroarilo sustituido y cada sustituyente se selecciona en forma independiente del grupo formado por: grupos R9; ó R3 es y R4 tomados junto con los átomos de carbono a los cuales están unidos en el sustituyente B del fenilo de fórmula (8), forman un anillo fusionado de la fórmula (9), donde Z1 o Z2 es un anillo heterocíclico saturado sustituido ó no sustituido (con preferencia un anillo heterocíclico de 4 a 7 miembros), dicho anillo Z1 ó Z2 contiene en forma opcional un heteroátomo adicional seleccionado del grupo formado por: O, S y NR18; donde hay 1 a 3 sustituyentes en dicho anillo Z1 ó Z2, y cada sustituyente se selecciona en forma independiente del grupo formado por: alquilo, arilo, hidroxi, hidroxialquilo, alcoxi, alcoxialquilo, arilalquilo, fluoroalquilo, cicloalquilo, cicloalquilalquilo, heteroarilo, heteroarilalquilo, amino, -C(O)OR15, -C(O)NR15R16, -SOtNR15R16, -C(O)R15, -SO2R15 siempre que R15 no sea H, -NHC(O)NR15R16, -NHC(O)OR15, halógeno, y un grupo heterocicloalquenilo; cada R5 y R6 son iguales o diferentes y se seleccionan en forma independiente del grupo formado por hidrógeno, halógeno, alquilo, alcoxi, -CF3, -OCF3, -NO2, -C(O)R13, -C(O)OR, -C(O)NR13R14, -SO(t)NR13R14, -C(O)NR13OR14, ciano, arilo sustituido ó no sustituido, y grupo heteroarilo sustituido ó no sustituido; donde hay 1 a 6 sustituyentes en dicho grupo arilo sustituido y cada sustituyente se selecciona en forma independiente del grupo formado por: grupos R9; y donde hay 1 a 6 sustituyentes en dicho grupo heteroarilo sustituido y cada sustituyente se selecciona en forma independiente del grupo formado por: grupos R9; cada R7 y R8 se selecciona en forma independiente del grupo formado por: H, alquilo sustituido ó no sustituido, arilo sustituido ó no sustituido, heteroarilo sustituido ó no sustituido, arilalquilo sustituido ó no sustituido, heteroarilalquilo sustituido ó no sustituido, cicloalquilo sustituido ó no sustituido, cicloalquilalquilo sustituido ó no sustituido, -CO2R13, -CONR13R14, alquinilo, alquenilo, y cicloalquenilo; y donde hay uno o más sustituyentes en dichos grupos R7 y R8 sustituidos, donde cada sustituyente se selecciona en forma independiente del grupo formado por: a) halógeno, b) -CF3, c) -COR13, d) -OR13, e) -NR13R14, f) -NO2, g)-CN, h) -SO2OR13, i) -Si(alquilo)3, donde cada alquilo se selecciona en forma independiente, j) -Si(arilo)3, donde cada alquilo se selecciona en forma independiente, k) -(R13)2R14Si, donde cada R13 se selecciona en forma independiente, l) -CO2R13, m) -C(O)NR13R14, n) -SO2NR13R14, o) -SO2R13, p) -OC(O)R13, q) -OC(O)NR13R14, r) -NR13C(O)R14, y s) -NR13CO2R14; (fluoroalquilo es un ejemplo no limitativo de un grupo alquilo que está sustituido con halógeno); R8a se selecciona del grupo formado por: hidrógeno, alquilo, cicloalquilo y cicloalquilalquilo; cada R9 se selecciona en forma independiente del grupo formado por: a) -R13, b) halógeno, c) -CF3, d) -COR13, e) -OR13, f) -NR13R14, g) -NO2, h) -CN, i) -SO2R13, j) -SO2NR13R14, k) -NR13COR14, l) -CONR13R14, m) -NR13CO2R14, n) -CO2R13, o) tetrazol-5-ilo, p) alquilo sustituido con uno o más grupos -OH, q) alquilo sustituido con uno o más grupos -NR13R14, y r) -N(R13)SO2R14; cada R10 y R11 se selecciona en forma independiente del grupo formado por R13, halógeno, -CF3, -OCF3, -NR13R14, -NR13C(O)NR13R14, -OH, -C(O)OR13, -SH, -SO(t)NR13R14, -SO2R13, -NHC(O)R13, -NHSO2NR13R14, -NHSO2R13, -C(O)NR13R14,- C(O)NR13OR14, -OC(O)R13 y ciano; R12 se selecciona del grupo formado por: hidrógeno, -C(O)OR13, grupo arilo sustituido ó no sustituido, heteroarilo sustituido ó no sustituido, arilalquilo sustituido ó no sustituido, cicloalquilo sustituido ó no sustituido, alquilo sustituido ó no sustituido, cicloalquilalquilo sustituido ó no sustituido, y heteroarilalquilo sustituido ó no sustituido; donde hay 1 a 6 sustituyentes en los grupos sustituidos R12 y cada sustituyente se selecciona en forma independiente del grupo formado por: grupos R9; cada R13 y R14 se selecciona en forma independiente del grupo formado por: H, alquilo sustituido ó no sustituido, arilo sustituido ó no sustituido, heteroarilo sustituido ó no sustituido, arilalquilo sustituido ó no sustituido, heteroarilalquilo sustituido ó no sustituido, cicloalquilo sustituido ó no sustituido, cicloalquilalquilo sustituido ó no sustituido, heterocíclico sustituido ó no sustituido, fluoroalquilo sustituido ó no sustituido, y heterocicloalquilalquilo sustituido ó no sustituido (donde "heterocicloalquilo" se refiere a heterocíclico); donde hay 1 a 6 sustituyentes en dichos grupos R13 y R14 sustituidos y cada sustituyente se selecciona en forma independiente del grupo formado por: alquilo, -CF3, -OH, alcoxi, arilo, arilalquilo, fluoroalquilo, cicloalquilo, cicloalquilalquilo, heteroarilo, heteroarilalquilo, -N(R40)2, -C(O)OR15, -C(O)NR15R16, -S(O)tNR15R16, -C(O)R15, -SO2R15 siempre que R15 no sea H, halógeno, y -NHC(O)NR15R16; ó R13 y R14 tomados junto con el nitrógeno al cual están unidos en los grupos -C(O)NR13R14 y -SO2NR13R14 forman un anillo heterocíclico saturado sustituido ó no sustituido, dicho anillo contiene en forma opcional un heteroátomo adicional seleccionado del grupo formado por: O, S y NR18; donde hay 1 a 3 sustituyentes en los grupos ciclizados sustituidos R13 y R14 y cada sustituyente se selecciona en forma independiente del grupo formado por: alquilo, arilo, hidroxi, hidroxialquilo, alcoxi, alcoxialquilo, arilalquilo, fluoroalquilo, cicloalquilo, cicloalquilalquilo, heteroarilo, heteroarilalquilo, amino, -C(O)OR15, -C(O)NR15R16, -SOtNR15R16, -C(O)R15, -SO2R15 siempre que R15 no sea H, -NHC(O)NR15R16, -NHC(O)OR15, halógeno, y un grupo heterocicloalquenilo; cada R15 y R16 se selecciona en forma independiente del grupo formado por: H, alquilo, arilo, arilalquilo, cicloalquilo y heteroarilo; R17 se selecciona del grupo formado por: -SO2alquilo, -SO2arilo, -SO2cicloalquilo, y -SO2heteroarilo; R18 se selecciona del grupo formado por: H, alquilo, arilo, heteroarilo, -C(O)R19, -SO2R19 y -C(O)NR19R20; cada R19 y R20 se selecciona en forma independiente del grupo formado por: alquilo, arilo y heteroarilo; R30 se selecciona del grupo formado por: alquilo, cicloalquilo, -CN, -NO2, ó -SO2R15 siempre que R15 no sea H; cada R31 se selecciona en forma independiente del grupo formado por: arilo insustituido, arilo sustituido ó no sustituido, heteroarilo sustituido ó no sustituido y cicloalquilo sustituido ó no sustituido; donde hay 1 a 6 sustituyentes en dichos grupos sustituidos R31 y cada sustituyente se selecciona en forma independiente del grupo formado por: alquilo, halógeno y -CF3; cada R40 se selecciona en forma independiente del grupo formado por: H, alquilo y cicloalquilo; g es 1 ó 2; y t es 0, 1 ó 2.
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US20040186142A1 (en) 2004-09-23
CN1720240A (zh) 2006-01-11
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DE60326080D1 (en) 2009-03-19
CA2501535A1 (en) 2004-04-22
US7691856B2 (en) 2010-04-06
US20070264230A1 (en) 2007-11-15
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HK1072432A1 (en) 2005-10-28
ES2321186T3 (es) 2009-06-03
PE20040570A1 (es) 2004-08-30
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WO2004033440A1 (en) 2004-04-22
WO2004033440A8 (en) 2005-06-02
EP1551818A1 (en) 2005-07-13
JP4664074B2 (ja) 2011-04-06
MXPA05003867A (es) 2005-11-23
CN1720240B (zh) 2010-10-27
AU2003288922A1 (en) 2004-05-04
JP2010270151A (ja) 2010-12-02

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