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AR062156A1 - Compuestos agonistas y selectivos del receptor s1p-1 - Google Patents

Compuestos agonistas y selectivos del receptor s1p-1

Info

Publication number
AR062156A1
AR062156A1 ARP070103371A ARP070103371A AR062156A1 AR 062156 A1 AR062156 A1 AR 062156A1 AR P070103371 A ARP070103371 A AR P070103371A AR P070103371 A ARP070103371 A AR P070103371A AR 062156 A1 AR062156 A1 AR 062156A1
Authority
AR
Argentina
Prior art keywords
alkyl
alkylene
co2h
aryl
alkylamino
Prior art date
Application number
ARP070103371A
Other languages
English (en)
Original Assignee
Praecis Pharm Inc
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 Praecis Pharm Inc filed Critical Praecis Pharm Inc
Publication of AR062156A1 publication Critical patent/AR062156A1/es

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    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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Abstract

Su preparacion y su uso como agentes inmunosupresivos farmacéuticamente activos para el tratamiento de los trastornos autoinmunes, el rechazo al transplante del organo, los trastornos asociados con el sistema activado inmune, tanto como otros desordenes modulados por la linfopenia o los receptores S1P. Reivindicacion 1: Un compuesto de la formula 1 o una sal farmacéuticamente aceptable de las mismas, donde R1 es hidrogeno, halogeno, ciano, alquilo, arilo, heteroarilo, cicloalquilo heterocicloalquilo, aralquilo, heteroalquilo, -O-alquilo, -O-arilo, -O-heteroarilo, -S-alquilo, alquileno-O-alquilo, alquileno-CO2H, alquileno-CO2alquilo, alquiloSO2, alquilenosulfonilo, alquileno-CO-amino, alquileno-CO-alquilamino, alquileno-CO- dialquil amino, alquileno-NH-CO2H, alquileno-NH-CO2alquilo-CO2alquilo, -OH, -C(O)-alquilo, -C(O)O-alquilo, -CONH2, -CO-alquilamino, -CO-dialquilamino, amino, alquilamino, o dialquilamino, cualquiera de los cuales puede estar opcionalmente substituido en carbono con los grupos 1, 2, o 3 seleccionados de halo, alquilo, haloalquilo, -CF3, arilo, -CN, -OH, o -O-alquilo; A es alquileno C1-20, alquenileno C2-20, o alquinileno C2-20, cada uno de los cuales puede estar opcionalmente substituido en carbono con los grupos 1, 2, o 3 seleccionados de OH, CO2H, CO2alquilo, halogeno, amino, alquilamino, dialquilamino, -O-alquilo, alquileno-O alquilo alquileno-OH, o alquileno-CO2H; X1 es una union o es CH2, O,-CH2O-, S, -S(O), -S(O)2, -C(O)-, -C(O)O-, o NRx, donde Rx es HI o alquilo C1-6; R' y Rö son cada uno independientemente hidrogeno, halogeno, alquilo opcionalmente substituido en carbono con halogeno, alquilo, o tomadas juntas con el carbono al cual están unidas forman C=O o un anillo de 3, 4, 5, o 6 miembros, que contienen opcionalmente 1 o 2 heteroátomos seleccionados de O NH, N-alquilo, SO, o SO2, cualquiera de los cuales puede estar opcionalmente substituido en carbono con alquilo o halogeno; R2 es ciano, alquilo, arilo, heteroarilo, cicloalquilo, heterocicloalquilo, aralquilo, heteroalquilo, -O-alquilo, -O-arilo, -O-heteroarilo, aralcoxi, heteroaralcoxi, -Salquilo, alquileno-O-alquilo, alquileno-CO2H, alquileno-CO2alquilo, alquiloSO2, alquilenosulfonilo, alquileno-CO-amino, alquileno-CO-alquilamino, alquileno-CO-dialquilamino, alquileno-NH-CO2H, alquileno-NH-CO2-alquilo -CO2alquilo, -OH, -C(O)-alquilo, -C(O)O-alquilo, -CONH2, -CO- alquilamino, -CO-dialquilamino, amino, alquilamino, y dialquilamino, cualquiera de los cuales puede estar opcionalmente substituido en carbono con los grupos 1, 2, o 3 seleccionados de halo, alquilo, OH, o -O-alquilo; R3 está ausente, hidrogeno, halogeno, ciano, alquilo, arilo, heteroarilo, cicloalquilo, heterocicloalquilo, aralquilo, heteroalquilo, -O-alquilo, -O-arilo, -O-heteroarilo, aralcoxi, heteroaralcoxi, -S-alquilo, alquileno-O-alquilo, alquileno-CO2H, alquileno-CO2alquilo, alquiloSO2, alquilenosulfonilo, alquileno-CO-amino, alquileno-CO- alquilamino, alquileno-CO-dialquilamino, alquileno-NH-CO2H, alquileno-NH-CO2alquilo -CO2alquilo, -OH, -C(O)-alquilo, -C(O)O-alquilo, -CONH2, -CO-alquilamino, CO-dialquilamino, amino, alquilamino, y dialquilamino, cualquiera de los cuales puede estar opcionalmente substituido en carbono con los grupos 1, 2, o 3 seleccionados de halo, alquilo, OH, o -O-alquilo; el anillo A es fenilo o piridilo; el anillo B es arilo, heteroarilo, heterociclo, o cicloalquilo, cualquiera de los cuales puede estar opcionalmente substituido en carbono con los grupos 1, 2, o 3 seleccionados del halogeno, alquilo, O-alquilo, CO2H, CO2alquilo, halogeno, amino, alquilamino, dialquilamino, -O-alquilo, alquileno-O-alquilo, alquileno-OH, o alquileno-CO2H, siempre que el anillo B no sea un compuesto de formula (2); R4 es hidrogeno, ciano, alquilo, arilo, heteroarilo, alquileno-O-alquilo, alquileno-OH, arilo, alquileno-O-alquilo, -CO2H, -CO2-alquilo, alquileno-CO2H, o alquileno-CO2-alquilo, alquileno- OC(O)R donde R es hidrogeno o alquilo; cicloalquilo, heterocicloalquilo, alquileno-NH2, alquileno-alquilamino, o alquileno-dialquilamino, cualquiera de los cuales puede estar opcionalmente substituido en carbono con los grupos 1, 2, o 3 seleccionados de OH, CO2H, CO2alquilo, halogeno, amino, alquilamino, dialquilamino, -O-alquilo, alquileno-Oalquilo, alquileno-OH, o alquileno-CO2H; R5 y R6 están cada uno independientemente seleccionados del grupo que consiste de hidrogeno, alquilo, alquileno-OH, arilo, alquileno-O-alquilo, -CO2H, CO2-alquilo, alquileno-OC(O)alquilo, cicloalquilo, heterociclo, -C(O)-alquilo, -C(O)-arilo, C(O)-aralquilo, -C(O)-Oalquilo, -C(O)-Oarilo, -C(O)-Oaralquilo, alquileno-amino, alquileno-alquilamino, y alquileno-dialquilamino, cualquiera de los cuales puede estar opcionalmente substituido en carbono con halogeno, alquilo, hidroxilo, CO2H, CO2alquilo o alcoxi; o R5 y R6, junto con el nitrogeno al cual están unidos, pueden formar un anillo de 3, 4, 5, o 6 miembros saturados o insaturados, que contienen opcionalmente 1 o 2 heteroátomos adicionales seleccionados de O, S, NH, o alquilo, y opcionalmente substituido en carbono con halogeno, alquilo, hidroxilo, o alcoxi; R7 está seleccionada del grupo que consiste de -OH, -O-alquilo, alquileno-OH, -CO2H, alquileno-CO2H, -C(O)O-alquilo, -alquileno-CO2-alquilo, -C(O)O-arilo, -CH2=CHCO2H, -CH2=CHC(O)O-alquilo, -CH2=CHC(O)O-arilo, -OPO2Rp1Rp2, OPO3Rp1Rp2, -CH2PO3Rp1Rp2, -OPO2(S)Rp1Rp2, y - C(Z')(Zö)PO3Rp1Rp2, cualquiera de los cuales puede estar opcionalmente substituido en carbono con halogeno, alquilo, hidroxilo, carboxi, o alcoxi; y donde Z' es hidroxilo o halogeno; Zö es H o halogeno; Rp1 y Rp2 son cada uno independientemente hidr6geno, alquilo C1-6, arilo, o uno de los grupos siguientes de las formulas (3); Y es heterociclo o heteroarilo.
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