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AR058180A1 - Indeno derivados, su preparacion y su uso como medicamentos - Google Patents

Indeno derivados, su preparacion y su uso como medicamentos

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Publication number
AR058180A1
AR058180A1 ARP060104876A ARP060104876A AR058180A1 AR 058180 A1 AR058180 A1 AR 058180A1 AR P060104876 A ARP060104876 A AR P060104876A AR P060104876 A ARP060104876 A AR P060104876A AR 058180 A1 AR058180 A1 AR 058180A1
Authority
AR
Argentina
Prior art keywords
alkyl
independently selected
substituted
phenyl
radical
Prior art date
Application number
ARP060104876A
Other languages
English (en)
Original Assignee
Esteve Labor Dr
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
Priority claimed from ES200502720A external-priority patent/ES2274725B1/es
Application filed by Esteve Labor Dr filed Critical Esteve Labor Dr
Publication of AR058180A1 publication Critical patent/AR058180A1/es

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    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups 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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    • C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
    • C07C311/44—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
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Abstract

La presente hace referencia a su procedimiento de preparacion, a su aplicacion como medicamento y a composiciones farmacéuticas que los comprenden. Los compuestos muestran afinidad por los receptores 5-HT6 por lo que se utilizan para el tratamiento de las enfermedades mediadas por estos receptores. Reivindicacion 1: Un indeno derivado de formula general (1) donde: n es 0, 1, 2, 3 o 4; R1 representa un radical cicloalifático saturado o insaturado, opcionalmente al menos monosustituido, opcionalmente al menos con un heteroátomo seleccionado entre N, O y S como miembro del anillo que puede estar condensado con un sistema anular mono o policíclico opcionalmente al menos monosustituido; un radical -NR8R9-; un radical -CONR8R9; -COOH; o -OH donde R8 y R9 representan, independientemente entre sí, un átomo de H; o un radical alifático C1-5 lineal o ramificado, saturado o insaturado, que puede estar sustituido con 1, 2, 3 sustituyentes seleccionados independientemente entre F, Cl, Br, -OH, -NH2, -SH, -O-CH3, -O-C2H5, -NO2, -CN, -NH-CH3 y -S-CH3; R8 y R9 conjuntamente con el N forman un anillo heterocíclico de 3 a 9 miembros saturado, insaturado o aromático, que puede estar sustituido con 1, 2 o 3 sustituyentes seleccionados independientemente entre C1-5 alquil, -O-C1-5 alquil, -S-C1-5-alquil, oxo (=O), tioxo (=S), -C(=O)-OH, -C(=O)-O-C1-5-alquil, -O-C(=O)-C1-5 alquil, F, Cl. Br, I, -CN, -CF3, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(C1-5 alquil), -N(C1-5 alquil)2, -NO2, -CHO, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH(C1-5 alquil), -C(=O)-N(C1-5 alquil)2, -S(=O)2-C1-5 alquil, -S(=O)2-fenil y que pueden contener 1, 2 o 3 heteroátomos adicionales independientemente seleccionados entre N, O y S como miembros del anillo; R2, R3, R4 y R5 representan, independientemente entre sí, un átomo de H, -NO2, -NH2, -SH, -OH, -CN, -C(=O)-H, -C(=O)-R10, -OR11, -SR12, -SOR13, -S(=O)2-E13, S(=O)2-N(R14)R15, -N(R16)-S(=O)2-R17, -NH-R18, -NR19R20, -N(R21)-CO-R22; F, Cl, BR, I, un radical alifático C1-6 lineal o ramificado, saturado o insaturado, que puede estar sustituido por 1, 2 o 3 sustituyentes independientemente seleccionados entre F, Cl, Br, -OH, -NH2, -SH, -O-CH3, -O-C2H5, -NO2, -CN, -NH-CH3 y -S-CH3; o un radical arilo o heteroarilo de 5 a 14 miembros, que puede estar sustituido con 1, 2 o 3 sustituyentes independientemente seleccionados entre -CF3, C1-5- alquil, -O-C1-5- alquil, -S-C1-5-alquil, -C(=O)-OH, -C(=O)-O-C1-5 alquil, -O-C(=O)-C1-5-alquil, F, Cl Br, I, - CN, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(C1-5 alquil), -N(C1-5 alquil)2, -NH-C(=O)-C1-5 alquil, -N(C1-5-alquil)-C(=O)-C1-5-alquil, -NO2, -CHO, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH(C1-5 alquil), -C(=O)-N(C1-5 alquil)2, -S(=O)2-C1-5 alquil, -S(=O)2-fenil, ciclopropil, ciclobutil, ciclopentil, ciclohexil, fenil, fenoxi, benciloxi y bencil y que pueden estar unidos a través de un grupo C1-6 alquileno lineal o ramificado y donde el radical heteroarilo contiene 1, 2 o 3 heteroátomos independientemente seleccionados entre N, O y S como miembros del anillo; con la condicion de que al menos uno de los sustituyentes R2, R3, R4 y R5 represente un radical -NO2, -SOR13, -S(=O)2-R13, -S(=O)2-N(R14)R15, -N(R16)-S(=O)2-R17, -N(R21)-CO-R22; A representa C=C(R6)R'6 o (R6)C-R'6 lo que significa, respectivamente, compuestos tipos (2) y (3); R6 y R'6, idénticos o diferentes, representan un átomo de H, -NO2, -NH2, -SH, -OH, -CN, -C(=O)-R10, -OR11, -SR12, F, Cl, BR, I, un radical alifático C1-10 lineal o ramificado, saturado o insaturado, que puede estar sustituido por 1, 2 o 3 sustituyentes independientemente seleccionados entre F, Cl, Br, -OH, -SH, -O-CH3, -O-C2H5, -NO2, -CN, y -S-CH3; o un radical arilo o heteroarilo de 5 a 14 miembros, que puede ser sustituido por 1, 2 o 3 sustituyentes independientemente seleccionado entre -CF3, C1-5- alquil, -O-C1-5- alquil, -S-C1-5-alquil, -C(=O)-OH, -C(=O)-O-C1-5 alquil, -O-C(=O)-C1-5-alquil, F, Cl Br, I, -CN, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(C1-5 alquil), -N(C1-5 alquil)2, -NH-C(=O)-C1-5 alquil, -N(C1-5-alquil)-C(=O)-C1-5-alquil, -NO2, -CHO, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH(C1-5 alquil), -C(=O)-N(C1-5 alquil)2, -S(=O)2-C1-5 alquil, -S(=O)2-fenil, ciclopropil, ciclobutil, ciclopentil, ciclohexil, fenil, fenoxi, benciloxi y bencil y que pueden estar unidos a través de un grupo C1-6 alquileno, C2-6 alquenileno o C1-6 ilideno lineales o ramificados y donde el radical heteroaril contiene 1, 2 o 3 heteroátomos independientemente seleccionados entre N, O y S como miembros del anillo; R7 representa un átomo de H, un radical alifático C1-6 lineal o ramificado que pude estar sustituido por 1, 2 o 3 sustituyentes independientemente seleccionados entre F, Cl, Br, -OH, -SH, -O- CH3, -O-C2H5, -NO2, -CN y -S-CH3; R10 a R22 representan, independientemente entre sí, un átomo de H, un radical alifático C1-5 lineal o ramificado, saturado o insaturado, que puede estar sustituido con 1, 2 o 3 sustituyentes independientemente seleccionados entre F, Cl, Br, -OH, NH2, -SH, -O-CH3, -O-C2H5, -NO2, -CN, -NH-CH3 y -S-CH3; un radical cicloalifático de 3 a 8 miembros saturado o insaturado, que puede estar sustituido con 1, 2 o 3 sustituyentes seleccionados entre C1-5-alquil, -O- C1-5-alquil, -S-C1-5-alquil, oxo (=O), tioxo (=S), -C(=O)-OH, -C(=O)-O-C1-5 alquil, -O-C(=O)-C1-5 alquil, F, Cl, Br, I, -CN, -CF3, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(C1-5 alquil), -N(C1-5 alquil)2, -NO2, -CHO, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)NH(C1-5 alquil), -C(=O)-NC1-5 alquil)2, -S(=O)2-C1-5 alquil, -S(=O)2-fenil, ciclopropil, ciclobutil, ciclopentil, ciclohexil, fenil, fenoxi, benciloxi y bencil y que opcionalmente puede contener 1, 2 o 3 heteroátomos independientemente seleccionados entre N, O y S como miembros del anillo y que pueden estar unidos a través de un grupo C1-6 alquileno lineal o ramificado; o un radical arilo o heteroarilo de 5 a 14 miembros que puede estar sustituidos con 1, 2 o 3 sustituyentes independientemente seleccionados entre -CF3, C1-5- alquil, -O-C1-5- alquil, -S-C1-5-alquil, -C(=O)-OH, -C(=O)-O-C1-5 alquil, -O-C(=O)-C1-5-alquil, F, Cl Br, I, -CN, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(C1-5 alquil), -N(C1-5 alquil)2, -NH-C(=O)-C1-5 alquil, -N(C1-5- alquil)-C(=O)-C1-5-alquil, -NO2, -CHO, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH(C1-5 alquil), -C(=O)-N(C1-5 alquil)2, -S(=O)2-C1-5 alquil, -S(=O)2-fenil, ciclopropil, ciclobutil, ciclopentil, ciclohexil, fenil, fenoxi, benciloxi y bencil y que pueden estar unidos a través de un grupo C1-6 alquileno, C2-6 alquenileno o C2-6 alquinileno lineales o ramificados y donde el radical heteroarilo contiene 1, 2 o 3 heteroátomos independientemente seleccionados entre N, O y S como miembros del anillo; con la condicion de que cuando R1 sea -COOH; R2, R3, R4 o R5 no sean -SOR13, -S(=O)2-R13 o -S(=O)2-N(R14)R15 y A no represente C=C(R6)R6' dándose la situacion conjunta en que R6 o R6' sean uno H y el otro un fenilo sustituido por -S(=O)2-C1-5 alquil, - NH2, -O-C1-5 alquil, F, Cl, Br, CN, -C(=O)-OH o -C(=O)-O-C1-5 alquil, o la situacion en que tanto R6 como R6' representen -OR11, y con la condicion de que cuando R1 sea -OH; R2, R3, R4 o R5 no sean -S(=O)2-R13 o -S(=O)2-N(R14)R15, y con la condicion de que cuando R1 sea -CONR8R9; R2, R3, R4 o R5 no sean -SOR13, -S(=O)2-R13 o -S(=O)2-N(R14)R15 y A no represente C=C(R6)R'6 dándose la situacion conjunta en que R6 o R'6 sean uno H y el otro un fenilo sustituido por -S(=O)2-C1-5 alquil, -NH2, -O-C1- 5 alquil, F, Cl, Br, CN, -C(=O)-OH o -C(=O)-O-C1-5 alquil, o una sal farmacéuticamente aceptable, un isomero, un profármaco o un solvato del mismo, opcionalmente en forma de uno de sus esteroisomeros, preferiblemente enantiomeros o diasteromeros, un racemato o en forma de una mezcla de al menos dos esteroisomeros, preferiblemente enantiomeros y/o diasteromeros, en cualquier proporcion de mezcla o una sal fisiologicamente aceptable de los mismos o el correspondiente solvato de los mismos.
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