AR033791A1 - Compuestos de acidos oxamicos y derivados como ligandos de receptores tiroideos,su uso. composicion y estuche que lo contiene - Google Patents
Compuestos de acidos oxamicos y derivados como ligandos de receptores tiroideos,su uso. composicion y estuche que lo contieneInfo
- Publication number
- AR033791A1 AR033791A1 ARP000100869A ARP000100869A AR033791A1 AR 033791 A1 AR033791 A1 AR 033791A1 AR P000100869 A ARP000100869 A AR P000100869A AR P000100869 A ARP000100869 A AR P000100869A AR 033791 A1 AR033791 A1 AR 033791A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- optionally substituted
- group
- hydrogen
- cycloalkyl
- Prior art date
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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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- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
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- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D211/10—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
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- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Abstract
Compuestos de la fórmula (1) y profármacos de los mismos, isómeros geométricos y ópticos de los mismos y sales farmacéuticamente aceptables de tales compuestos, profármacos e isómeros en los 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; 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 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 Y, 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, -(alquilo 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 arilo opcionalmente sustituido con X e Y; R17 es hidrógeno, alquilo C1-6, -COR9 o -SO2R9; 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 o 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 anillo 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 contienen 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 o 2; b es 3, 4, 5, 6 o 7; cada uno de c, f, g, j y k son independientemente 2, 3, 4, 5 o 6; y e es 3, 4, 5, 6 o 7. También se proporcionan composiciones farmacéuticas que contienen tales compuestos, profármacos, isómeros o sales farmacéuticamente aceptables de los mismos, y usos para la fabricación de medicamentos, composiciones farmacéuticas y estuches para el tratamiento de la obesidad, hiperlipidemia, glaucoma, arritmia cardíaca, trastornos cutáneos, enfermedad del tiroides, hipotiroidismo y trastornos y enfermedades relacionadas tales como diabetes mellitus, aterosclerosis, hipertensión, enfermedad cardíaca coronaria, hipercolesterolemia, depresión y osteoporosis.
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