CO5150228A1 - Acidos oxamicos y derivados como ligandos de receptores tiroideos - Google Patents

Acidos oxamicos y derivados como ligandos de receptores tiroideos

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Publication number
CO5150228A1
CO5150228A1 CO00014839A CO00014839A CO5150228A1 CO 5150228 A1 CO5150228 A1 CO 5150228A1 CO 00014839 A CO00014839 A CO 00014839A CO 00014839 A CO00014839 A CO 00014839A CO 5150228 A1 CO5150228 A1 CO 5150228A1
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CO
Colombia
Prior art keywords
alkyl
optionally substituted
group
hydrogen
nr9r10
Prior art date
Application number
CO00014839A
Other languages
English (en)
Inventor
Ching Phoebe Chiang Yuang
Robert Lee Dow
Original Assignee
Pfizer Prod Inc
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Publication date
Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc
Publication of CO5150228A1 publication Critical patent/CO5150228A1/es

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    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
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  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Un compuesto de Fórmula<EMI FILE="00014839_1" ID="1" IMF=JPEG >un "profármaco" del mismo, un isómero geométrico u óptico del mismo o una sal farmacéuticamente aceptable de dicho compuesto, de dicho "profármaco" o de dicho isómero, en la que: cada uno de R1, R2 y R3 es independientemente hidrógeno, halógeno, alquilo C1-6, trifluorometilo, -CN, -OCF3 u -O-alquilo C1-6;R4 es hidrógeno, alquilo C1-12 opcionalmente sustituido con uno a tres sustituyentes seleccionados independientemente entre el Grupo Z, alquenilo C2-12, halógeno, -CN, arilo, heteroarilo, cicloalquilo C3-10, heterocicloalquilo, -S(O)2NR9R10, -C(O)NR9R10, -alquilo C1-6)-NR9R10, -NR9C(O)R10, -NR9C(O)NR9R10, -NR9S(O)2R10, -(alquilo C1-6)-OR11, -OR11 o -S(O)aR12, con la condición de que, cuando R5 no es flúor, R4 es -S(O)2NR9R10, -C(O)NR9R10, -(alquilo C1-6)-NR9R10, -NR9C(O)R10, -NR9C(O)NR9R10, -NR9S(O)2R10, -(alquilo C1-6)-OR11, -OR11 o -S(O)aR12;o R3 y R4 pueden tomarse conjuntamente para formar un anillo carbocíclico A de fórmula -(CH2)b- o un anillo heterocíclico A seleccionado entre el grupo compuesto por -Q-(CH2)c y -(CH2)j-Q-(CH2)k-, en los que Q es O, S o NR17, estando cada uno de dichos anillos carbocíclico A y heterocíclico A opcionalmente sustituido independientemente con uno o más sustituyentes seleccionados independientemente entre alquilo C1-4, haluro u oxo;R5 es flúor, hidroxi, alcoxi C1-4 o OC(O)R9;o R4 y R5 pueden tomarse conjuntamente para formar un anillo heterocíclico B seleccionado entre el grupo compuesto por -CR9=CR10-NH, -N=CR9-NH-, -CR9=CH-O- y -CR9=CH-S-;R6 es hidrógeno, halógeno, alquilo C1-4 o trifluorometilo;R7 es hidrógeno o alquilo C1-6;R8 es -OR9 o -NR19R20;R9 y R10, cada vez que aparecen, son independientemente (A) hidrógeno, (B) alquilo C1-12 opcionalmente sustituido con uno o más sustituyentes seleccionados independientemente entre el Grupo V, (C) alquenilo C2-12, (D) cicloalquilo C3-10 opcionalmente sustituido con uno o más sustituyentes seleccionados independientemente entre alquilo C1-6, alquinilo C2-5, cicloalquilo C3-10, -CN, -NR13R14, oxo, -OR18, -COOR18 o arilo opcionalmente sustituido con X e Y, (E) arilo opcionalmente sustituido con X e Y, o (F) het opcionalmente sustituido con X e Y;- 2 -o R9 y R10, cada vez que aparecen, pueden tomarse conjuntamente para formar un anillo heterocíclico C que además contiene opcionalmente un segundo heterogrupo seleccionado entre el grupo compuesto por -O-, -NR13- y -S-, y además está opcionalmente sustituido con uno o más sustituyentes seleccionados independientemente entre alquilo C1-5, oxo, -NR13R14, -OR18, -C(O)2R18, -CN, -C(O)R9, arilo opcionalmente sustituido con X e Y, het opcionalmente sustituido con X e Y, espirocicloalquilo C5-6 y un anillo carbocíclico B seleccionado entre el grupo compuesto por anillos carbocíclicos de 5, 6, 7 u 8 miembros, parcial y totalmente saturados, e insaturados, incluyendo cualquier grupo bicíclico en el que dicho anillo carbocíclico B esté condensado con un anillo carbocíclico C seleccionado entre el grupo compuesto por anillos carbocíclicos de 5, 6, 7 u 8 miembros parcial y totalmente saturados, e insaturados; R11 es alquilo C1-12 opcionalmente sustituido con uno o más sustituyentes seleccionados independientemente entre el Grupo V, alquenilo C2-12, cicloalquilo C3-10, trifluorometilo, difluorometilo, monofluorometilo, arilo opcionalmente sustituido con X e V, het opcionalmente sustituido con X e Y, -C(O)NR9R10 o -C(O)R9;R12 es alquilo C1-12 opcionalmente sustituido con uno o más sustituyentes seleccionados independientemente entre el Grupo V, alquenilo C2-12, cicloalquilo C3-10, arilo opcionalmente sustituido con X e Y, o het opcionalmente sustituido con X e Y;R13 y R14, cada vez que aparecen, son independientemente hidrógeno, alquilo C1-6, alquenilo C2-6, -(alquilo C1-6)-alcoxi C1-6, arilo opcionalmente sustituido con X e Y, het opcionalmente sustituido con X e Y, -(alquil C1-4)-arilo opcionalmente sustituido con X e Y, -(alquil C1-4)-heterociclo opcionalmente sustituido con X e Y, -(alquil C1-4)-hidroxi, -(alquil C1-4)-halo, -(alquil C1-4)-poli-halo, -(alquil C1-4)-CONR15R16 o cicloalquilo C3-10;R15 y R16, cada vez que aparecen, son independientemente hidrógeno, alquilo C1-6, cicloalquilo C3-10 o ari lo opcionalmente sustituido con X e Y;R17 es hidrógeno, alquilo C1-6, -COR9 o -S02R9;R18 es hidrógeno, alquilo C1-6, alquenilo C2-6, -(alquil C1-6)-alcoxi C1-6, arilo opcionalmente sustituido con X e Y, het opcionalmente sustituido con X e Y, -(alquil C1-4)-arilo opcionalmente sustituido con X e Y, -(alquil C1-4)-heterociclo opcionalmente sustituido con X e Y, -(alquil C1-4)-hidroxi, -(alquil C1-4)-halo, -(alquil C1-4)-poli-halo, -(alquil C1-4)-CONR15R16, -(alquil C1-4)-(alcoxi C1-4) o cicloalquilo C3-10;R19 es hidrógeno o alquilo C1-6;R20 es hidrógeno o alquilo C1-6;W es O, S(O)d, CH2 o NR9;El Grupo Z es alquenilo C2-6, alquinilo C2-6, halógeno, -CF3, -OCF3, hidroxi, oxo, -CN, arilo, heteroarilo, cicloalquilo C3-10, heterocicloalquilo, -S(O)aR12, -S(O)2NR9R10, -C(O)R9R10 y -NR9R10;El Grupo V es halógeno, -NR13R14, -OCF3, -OR9, oxo, trifluorometilo, -CN, cicloalquilo C3-10, arilo opcionalmente sustituido con X e Y, y het opcionalmente sustituido con X e Y;het, cada vez que aparece, es un anillo heterocíclico D seleccionado entre el grupo compuesto por anillos heterocíclicos de 4, 5, 6, 7 y 8 miembros parcial y totalmente saturados, e insaturados, que contiene de uno a cuatro heteroátomos seleccionados independientemente entre el grupo compuesto por N, O y S, y que incluye cualquier grupo bicíclico en el que dicho anillo heterocíclico D esté condensado con un anillo de benceno o un anillo heterocíclico E seleccionado entre el grupo compuesto por anillos heterocíclicos de 4, 5, 6, 7 y 8 miembros parcial y totalmente saturados, e insaturados, que contiene de uno a cuatro heteroátomos seleccionados independientemente entre el grupo compuesto por N, O y S;X e Y, cada vez que aparecen, son independientemente (A) hidrógeno, (B) halógeno, (C) trifluorometilo, (D) -OCF3, (E) -CN, (F) alquilo C1-6 opcionalmente sustituido con uno o más sustituyentes seleccionados independientemente entre el grupo compuesto por halógeno, -OCF3, -CF3 y fenilo, (G) alcoxi C1-6, (H) arilo opcionalmente sustituido con uno o más sustituyentes seleccionados independientemente entre el grupo compuesto por halógeno, -OCF3, -CF3, alquilo C1-4 y alcoxi C1-4, (I) -C(O)2R13, (J) -C(O)NR13R14, (K) -C(O)R13, (L) -NR13C(O)NR13R14 y (M) -NR13C(O)R14;o X e Y, cada vez que aparecen en la misma variable, pueden tomarse conjuntamente para formar (a) un anillo carbocíclico D de fórmula -(CH2)e- o (b) un anillo heterocíclico F seleccionado entre el grupo compuesto por -O(CH2)fO-, (CH2)gNH- y -CH=CHNH-;cada uno de a y d son independientemente 0, 1 ó 2;b es 3,4,5,6 ó 7;cada uno de c, f, g, j y k son independientemente 2, 3,4, 5, ó 6; ye es 3, 4, 5, 6 ó 7.
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