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AR043694A1 - Derivados ciclicos como moduladores de la actividad del receptor de quimiocina - Google Patents

Derivados ciclicos como moduladores de la actividad del receptor de quimiocina

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Publication number
AR043694A1
AR043694A1 ARP040100419A ARP040100419A AR043694A1 AR 043694 A1 AR043694 A1 AR 043694A1 AR P040100419 A ARP040100419 A AR P040100419A AR P040100419 A ARP040100419 A AR P040100419A AR 043694 A1 AR043694 A1 AR 043694A1
Authority
AR
Argentina
Prior art keywords
substituted
crr
alkyl
alkynyl
alkenyl
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Application number
ARP040100419A
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English (en)
Inventor
R J Cherney
P H Carter
Original Assignee
Bristol Myers Squibb Co
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Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co
Publication of AR043694A1 publication Critical patent/AR043694A1/es

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    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
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    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
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Abstract

Un compuesto cíclico de la fórmula (1) o un estereoisómero o una sal farmacéuticamente aceptable de los mismos, en donde el anillo B es un grupo cicloalquilo de 3 hasta 8 átomos de carbono en donde el grupo cicloalquilo está saturado o parcialmente insaturado; o un heterociclo de 3 hasta 7 átomos en donde el heterociclo está saturado o parcialmente insaturado, el heterociclo contiene un heteroátomo seleccionado de -O-, -S-, -S(=O)-, -S(=O)2-, y -N(R4)-, el heterociclo contiene opcionalmente un -C(O)-; el anillo B está substituido con 0-2 R5; X se selecciona de O ó S; Z se selecciona de un enlace, -C(O)-, y -C(O)NR8-, NR8C(S)-, NR8C(O)NH-, NR8C(S)NH-, NR8SO2-, NR8SO2NH-, -C(O)NR8-, -OC(O)NR8-, -NR8C(O)O-, -(CR15R15)-, -CR14=CR14-, -CR15R15C(O)-, -C(O)R15R15-, -CR15R15C(=N-OR16)-, -O-CR14R14-, -CR14R14-O-, -O-, _NR9-, -NR9-CR14R14-, -CR14R14-NR9-, -S(O)p-, -S(O)p-CR14R14-, -CR14R14-S(O)p-, y -S(O)p-NR9; en donde ni Z ni R13 se conectan al átomo de carbono etiquetado (b); el enlace (a) es un enlace sencillo o doble; alternativamente, cuando n es igual a 2, dos átomos etiquetados (b) pueden unirse a través de un enlace doble; E se selecciona de -S(O)pCHRe-, -CHReNRe-, -C(O)-NRe-, -NReC(O)NRe-, -SO2-NRe-, y -NReSO2NRe ;Re se selecciona independientemente de H y alquilo C1-3; R1 se selecciona de un grupo arilo C6-10 substituido con 0-5 R6 y un sistema heteroarilo de 5-10 miembros que contiene 1-4 heteroátomos seleccionado de N, O, y S, substituido con 0-3 R6 ;R2 se selecciona de un grupo C6-10 arilo substituido con 0-5 R7 y un sistema heteroarilo de 5-10 miembros que contiene 1-4 heteroátomos seleccionados de N, O, y S, substituido con 0-3 R7; R4 se selecciona de H, alquilo C1-6, alquenilo C3-8, alquinilo C3-8, (CRR)tOH, (CRR)tSH, (CRR)tOR4d, (CHR)tSR4d, (CRR)tNR4aR4a, (CRR)qC(O)OH, (CRR)rC(O)R4b, (CRR)rC(O)NR4aR4a, (CRR)tOC(O)NR4aR4a, (CRR)tNR4aC(O)OR4d, (CRR)tNR4aC(O)R4b, (CRR)rC(O)OR4d, (CRR)tOC(O)R4b, (CRR)rS(O)pR4b, (CRR)rS(O)2NR4aR4a, (CRR)tNR4aS(O)2R4b, haloalquilo C1-6, un residuo carbocíclico (CRR)r-C3-10 substituido con 0-3 R4e, y un sistema heterocíclico (CHR)r- de 4-10 miembros que contiene 1-4 heteroátomos seleccionado de N, O, y S, substituido con 0-2 R4e ; R4a, cada vez que se presenta, se selecciona independientemente de H, metilo substituido con 0-1R4C, alquilo C2-6 substituido con 0-3 R4e, alquenilo C3-8 substituido con 0-3 R4e, alquinilo C3-8 substituido con 0-3 R4e, un residuo carbocíclico(CH2)r- C3-10 substituido con 0-4 R4e, y un sistema heterocíclico (CHR)r- de 4-10 miembros que contiene 1-4 heteroátomos seleccionado de N, O, y S, substituido con 0-2 R4e ; R4b, cada vez que se presenta, se selecciona de H, alquilo C1-6 substituido con 0-3R4e, alquenilo C3-8 substituido con 0-3 R4e, alquinilo C3-8 substituido con 0-3 R4e, un residuo carbocíclico (CH2)r- C3-6 substituido con 0-2 R4e, y un sistema heterocíclico (CHR)r- de 4-10 miembros que contiene 1-4 heteroátomos seleccionado de N, O, y S, substituido con 0-2 R4e; R4c se selecciona independientemente de -C(O)R4b, -C(O)OR4d, -C(O)NR4fR4f, y (CH2)rfenilo; R4d, cada vez que se presenta, se selecciona de metilo, CF3, alquilo C2-6 substituido con 0-3R4e, alquenilo C3-8 substituido con 0-3R4e, alquinilo C3-8 substituido con 0-3 R4e, y un residuo carbocíclico C3-10 substituido con 0-3 R4e ; R4e, cada vez que se presenta, se selecciona de alquilo C1-6, alquenilo C2-8, alquinilo C2-8, cicloalquilo (CH2)rC3-6, Cl, F, Br, I, CN, NO2, (CF2)rCF3, (CH2)rOalquilo C1-5, OH, SH, (CH2)rSalquilo C1-5, (CH2)rNR4fR4f, -C(O)R4i, -C(O)OR4j, -C(O)NR4hR4h, -OC(O)NR4hR4h, -NR4hC(O)NR4hR4h, -NR4hC(O)OR4h, y (CH2)rfenilo; R4f cada vez que se presenta, se selecciona de H, alquilo C1-6, cicloalquilo C3-6 y fenilo; R4h cada vez que se presenta, se selecciona independientemente de H, alquilo C1-6, alquenilo C3-8, alquinilo C3-8 y un carbociclo (CH2)r C3-10; R4i cada vez que se presenta, se selecciona de H, alquilo C1-6, alquenilo C3-8, alquinilo C3-8 y un carbociclo (CH2)r C3-10; R4j cada vez que se presenta, se selecciona de CF3, alquilo C1-6, alquenilo C3-8, alquinilo C3-8 y un residuo carbocíclico C3-10; R5, cada vez que se presenta, se selecciona independientemente H, =O, alquilo C1-6, alquenilo C2-8, alquinilo C2-8, (CRR)rOH, (CRR)rSH, (CRR)rOR5d, (CRR)rSR5d, (CRR)rNR5aR5a, (CRR)rN(->O)R5aR5a, N3, (CRR)rC(O)OH, (CRR)rC(O)R5b, (CRR)rC(O)NR5aR5a, (CRR)rNR5aC(O)R5b, (CRR)rOC(O)NR5aR5a, (CRR)rNR5aC(O)OR5d, (CRR)rNR5aC(O)NR5aR5a, (CRR)rNR5aC(O)H, (CRR)rC(O)OR5d, (CRR)rOC(O)R5b, (CRR)rS(O)pR5b, (CRR)rS(O)2NR5aR5a, (CRR)rNR5aS(O)2R5b, (CRR)rNR5aS(O)2NR5aR5a, haloalquilo C1-6, un residuo carbocíclico (CRR)r- C3-10 substituido con 0-3 R5c, y un sistema heterocíclico (CRR)r de 5-10 miembros que contiene 1-4 heteroátomos seleccionado de N, O, y S, substituido con 0-2 R5c; R5a, cada vez que se presenta, se selecciona independientemente de H, metilo substituido con 0-1 R5g, alquilo C2-6 substituido con 0-2 R5e, alquenilo C3-8 substituido con 0-2 R5e, alquinilo C3-8 substituido con 0-2 R5e, un residuo carbocíclico (CH2)r- C3-10 substituido con 0-5 R5e, un sistema heterocíclico (CH2)r de 5-10 miembros que contiene 1-4 heteroátomos seleccionado de N, O, y S, substituido con 0-3R5e; R5b cada vez que se presenta, se selecciona de alquilo C1-6 substituido con 0-3 R5e, alquenilo C3-8 substituido con 0-2 R5e, alquinilo C3-8 substituido con 0-2 R5e, un residuo carbocíclico(CH2)r- substituido con 0-2 R5e y un sistema heterocíclico(CH2)r de 5-6 miembros que contiene 1-4 heteroátomos seleccionado de N, O, y S, substituido con 0-3 R5e; R5c, cada vez que se presenta, se selecciona de alquilo C1-6, alquenilo C2-8, alquinilo C2-8, cicloalquilo(CH2)r C3-6, Cl, Br, I, F, (CF2)rCF3, NO2, CN, (CH2)rNR5fR5f, (CH2)rOH, (CH2)rOalquilo C1-4, (CH2)rSalquilo C1-4, (CH2)rC(O)OH, (CH2)rC(O)R5b, (CH2)rC(O)NR5fR5f, (CH2)rOC(O)NR5fR5f, (CH2)rNR5fC(O)R5b, (CH2)rC(O)Oalquilo C1-4, (CH2)rNR5fC(O)Oalquilo C1-4, (CH2)rOC(O)R5b, (CH2)C(=NR5f)R5fR5f, (CH2)rS(O)pR5b, (CH2)rNHC(=NR5f)NR5fR5f, (CH2)rS(O)2NR5fR5f, (CH2)NR5fS(O)2R5b y (CH2)rfenilo substituido con 0-3 R5e; R5d cada vez que se presenta, se selecciona de metilo, CF3, alquilo C2-6 substituido con 0-2 R5e, alquenilo C3-8 substituido con 0-2 R5e, alquinilo C3-8 substituido con 0-2 R5e, un residuo carbocíclico C3-10 substituido con 0-3 R5e; R5e cada vez que se presenta, se selecciona de alquilo C1-6, alquenilo C2-8, alquinilo C2-8,cicloalquilo C3-6, Cl, F, Br, I, CN, NO2, (CF2)rCF3, (CH2)rOalquilo C1-5, OH, SH, (CH2)rSalquilo C1-5, (CH2)rNR5fR5f, y (CH2)rfenilo; R5f, cada vez que se presenta, se selecciona de H, alquilo, y cicloalquilo ; R5g se selecciona independientemente de -C(O)R5b, -C(O)OR5d, - C(O)NR5fR5f, CN, y (CH2)rfenilo ; R, cada vez que se presenta, se selecciona de H, alquilo C1-6 substituido con R5e, alquenilo C2-8, alquinilo C2-8, cicloalquilo(CH2)r C3-6, y (CH2)rfenilo substituido con R5e ;R6, cada vez que se presenta, se selecciona de alquilo C1-8, alquenilo, alquinilo, cicloalquilo(CH2)r C3-6, Cl, Br, I, F, NO2, CN, (CR'R')rNR6aR6a, (CR'R')rOH, (CR'R')rO(CR'R')rR6d, (CR'R')rSH, (CR'R')rC(O)H, (CR'R')rS(CR'R')rR6d, (CR'R')rSC(O)(CR'R')rR6b, (CR'R')rC(O)OH, (CR'R')rC(O)(CR'R')rR6b, (CR'R')rNR6aR6a, (CR'R')rC(O)NR6aR6a, (CR'R')rNR6fC(O)(CR'R')rR6b, (CR'R')rC(O)O(CR'R')rR6d, (CR'R')rOC(O)(CR'R')rR6b, (CR'R')rOC(O)NR6a(CR'R')rR6d, (CR'R')rNR6aC(O)NR6a(CR'R')rR6d, (CR'R')rNR6aC(S)NR6a(CR'R')rR6d, (CR'R')rNR6fC(O)O(CR'R')rR6b, (CR'R')rC(=NR6f)NR6aR6a, (CR'R')rNHC(=NR6f)NR6fR6f, (CR'R')rS(O)p(CR'R')rR6b, (CR'R')rS(O)2NR6aR6a, (CR'R')rNR6fS(O)2NR6aR6a, (CR'R')rNR6fS(O)2(CR'R')rR6b, haloalquilo, alquenilo substituido con 0-3 R', alquinilo substituido con 0-3 R', (CR'R')rfenilo substituido con 0-3 R6e, y un sistema heterocíclico(CH2)r de 5-6 miembros que contiene 1-2 heteroátomos seleccionado de N, O, y S, substituido con 0-2 R6e ; alternativamente, dos R6 en los átomos adyacentes en R1 pueden unirse para formar un acetal cíclico; R6a, cada vez que se presenta, se selecciona de H, metilo substituido con 0-1 R6g,alquilo substituido con 0-2 R6e, alquenilo substituido con 0-2 R6e, alquinilo substituido con 0-2 R6e, un residuo carbocíclico (CH2)r- C3-10 substituido con 0-5 R5e, un sistema heterocíclico(CH2)r de 5-10 miembros que contiene 1-4 heteroátomos seleccionado de N, O, y S, substituido con 0-2 R6e ; R6b, cada vez que se presenta, se selecciona de H, alquilo C1-6 substituido con 0-2 R6e, alquenilo C3-8 substituido con 0-2 R6e, alquinilo C3-8 substituido con 0-2 R6e, un residuo carbocíclico(CH2)r- C3-6 substituido con 0-3 R6e, un sistema heterocíclico(CH2)r de 5-6 miembros que contiene 1-4 heteroátomos seleccionado de N, O, y S, substituido con 0-2 R6e ; R6d cada vez que se presenta, se selecciona de alquenilo C3-8 substituido con 0-2 R6e, alquinilo C3-8 substituido con 0-2 R6e, metilo, CF3, alquilo C2-6 substituido con R6e, haloalquilo C2-4, un residuo carbocíclico(CH2)r- C3-10 substituido con 0-3 R6e, un sistema heterocíclico(CH2)r de 5-6 miembros que contiene 1-4 heteroátomos seleccionado de N, O, y S, substituido con 0-3 R6e; R6e, cada vez que se presenta, se selecciona de alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo(CH2)r C3-6, Cl, F, Br, I, CN, NO2, (CF2)rCFu, alquilo(CH2)rO C1-6OH, SH, alquilo (CH2)rS C1-6, (CH2)rNR6fR6f, y (CH2)rfenilo; R6f, cada vez que se presenta, se selecciona de H, alquilo C1-5, y cicloalquilo C3-6, y fenilo; R6g se selecciona independientemente de -C(O)R6b, -C(O)OR6d, -C(O)NR6fR6f, y (CH2)rfenilo; R7, cada vez que se presenta, se selecciona de alquilo C1-6, alquenilo C2-8, alquinilo C2-8, cicloalquilo(CH2)r C3-6, Cl, Br, I, F, NO2, CN, (CR'R')rNR7aR7a, (CR'R')rOH, (CR'R')rO(CR'R')rR7d, (CR'R')rSH, (CR'R')rC(O)H, (CR'R')rS(CR'R')rR7d, (CR'R')rC(O)OH, (CR'R')rC(O)(CR'R')rR7b, (CR'R')rC(O)NR7aR7a, (CR'R')rNR7fC(O)(CR'R')rR7b, (CR'R')rC(O)O(CR'R')rR7d, (CR'R')rOC(O)(CR'R') rR7b, (CR'R')rOC(O)NR7a(CR'R')rR7a, (CR'R')rNR7aC(O)NR7a(CR'R')rR7a, (CR'R')rNR7fC(O)O(CR'R')rR7d, (CR'R')rC(=NR7f)NR7aR7a, (CR'R')rNHC(=NR7f)NR7f
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