AR050364A1 - Derivados de sulfonamidas, su preparacion y su aplicacion en terapeutica - Google Patents

Derivados de sulfonamidas, su preparacion y su aplicacion en terapeutica

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Publication number
AR050364A1
AR050364A1 ARP050103194A ARP050103194A AR050364A1 AR 050364 A1 AR050364 A1 AR 050364A1 AR P050103194 A ARP050103194 A AR P050103194A AR P050103194 A ARP050103194 A AR P050103194A AR 050364 A1 AR050364 A1 AR 050364A1
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AR
Argentina
Prior art keywords
group
alkyl group
alkyl
optionally substituted
independently
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ARP050103194A
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English (en)
Inventor
Gilles Courtemanche
Pierre Despeyroux
Evelyne Fontaine
Pierrick Rochard
Claudine Serradeil-Legal
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Sanofi Aventis
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Application filed by Sanofi Aventis filed Critical Sanofi Aventis
Publication of AR050364A1 publication Critical patent/AR050364A1/es

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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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    • 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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    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
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Abstract

La presente se refiere a derivados de sulfonamidas, se refiere también al procedimiento de preparacion, así como a la utilizacion en terapéutica de los compuestos de formula (1) en diabetes, anorexia, bulimia, depresion, ansiedad, adicciones, esquizofrenia, y disfuncion del receptor orexina 2. Reivindicacion 1: Compuesto que responde a la formula general (1) en la cual: Ar1 representa: i) un grupo arilo tal como un grupo fenilo, eventualmente, substituido por uno o varios grupos elegidos, independientemente entre sí, entre los grupos siguientes: un átomo de halogeno, un grupo alquilo C1-4, un grupo alcoxi C1-4, un grupo fluoroalquilo C1-4, un grupo ciano, un grupo -CO-NRaRb, o un grupo -NRaRb, con Ra y Rb que son, independientemente entre sí, un átomo de hidrogeno o un grupo alquilo C1-4; ii) un grupo heterociclilo elegido entre piridinilo, pirimidinilo, tiazolilo, tienilo, y dichos grupos heterociclilos están substituidos, eventualmente, por un átomo de halogeno, un grupo alquilo C1-4 o un grupo alcoxi C1-4; o iii) un grupo cicloalquilo C3-6; T representa un grupo -(CH2)n- con n = 0, 1 o 2; un grupo >CH-R2 con R2 que es un grupo hidroxilo o alquilo C1-4; un grupo >N-R3 con R3 que es un grupo alquilo C1-4; o un grupo >C(OH)-R4 con R4 que es un grupo alquilo C1-4; Ar2 representa: i) un grupo arilo tal como fenilo, eventualmente substituido por uno o varios grupos elegidos, independientemente entre sí, entre los grupos siguientes; un átomo de halogeno, un grupo alquilo C1-4, un grupo alcoxi C1-4, un grupo fluoroalquilo C1-4, un grupo fluoroalcoxi C1-4, o bien por un grupo -NRcRd con Rc y Rd que son, independientemente entre sí, un átomo de hidrogeno o un grupo alquilo C1-4; o ii) un grupo heterociclilo tal como piridinilo, eventualmente substituido por un grupo alquilo C1-4 o un grupo alcoxi C1-4; Ar3 representa: i) un grupo arilo elegido entre fenilo y naftilo, y dichos grupos arilos están substituidos, eventualmente, por uno o varios grupos elegidos independientemente entre sí, entre los grupos siguientes: un átomo de halogeno, un grupo alquilo C1-4, un grupo alcoxi C1-4, un grupo fluoroalquilo C1-4, un grupo fluoroalcoxi C1-4, un grupo nitro, un grupo hidroxi, o bien por un grupo -NR5R6 con R5 y R6 que son, independientemente entre sí, un átomo de hidrogeno o un grupo alquilo C1-4; ii) un grupo heterociclilo tal como piridinilo, eventualmente substituido por un grupo alquilo C1-4 o un grupo alcoxi C1-4, o bien por un grupo -NRxRy con Rx y Ry que son, independientemente entre sí, un átomo de hidrogeno, un grupo alquilo C1-4 o un grupo alcoxi C1-4; o iii) un resto elegido del grupo de formulas (2); y R1 representa i) un grupo -C(O)-CF3; ii) un grupo de formula (3), en la cual: n = 0, 1, 2 o 3; R7 representa un átomo de hidrogeno, un grupo alquilo C1-4, un átomo de fluor, un grupo alcoxi C1-4 o un grupo -(CH2)m-arilo, con m = 1 o 2, y el grupo arilo es un grupo fenilo, eventualmente substituido por un átomo de halogeno, un grupo alquilo C1-4 o un grupo alcoxi C1-4; R8 representa un átomo de hidrogeno, un átomo de fluor o un grupo alquilo C1-4; R9 representa a) un átomo de hidrogeno, un grupo alquilo C1-4, un grupo hidroxilo, un grupo cicloalquilo C3-6, un grupo alcoxi C1-4, un grupo fluoroalquilo C1-4, un grupo -C:::CH, un grupo -C:::N, un grupo fenoxi o un grupo alquenilo C1-4; o b) un grupo -NR10R11 con R10 y R11 que son, independientemente entre sí, un átomo de hidrogeno, un grupo alquilo C1-4, un grupo alquilcarbonilo C1-4, un grupo alquilsulfonilo C1-4, un bencilo o un grupo -(CH2)2-N(CH3)2, o bien R10 y R11 forman junto con el átomo de nitrogeno que los lleva, una pirrolidina, una pirrolidinona, una morfolina o una piperidina; iii) un grupo -CO- NR12R13 con R12 y R13 que son, independientemente entre sí un átomo de hidrogeno o un grupo alquilo C1-4 eventualmente substituido por un grupo -C:::N, un grupo arilo, tal como fenilo, un grupo heterociclilo, tal como piridinilo, y dichos grupos arilo y heterociclilo están substituidos, eventualmente, por un grupo alquilo C1-4, un grupo hidroxilo, o bien R12 y R13 forman junto con el átomo de nitrogeno que los lleva, un grupo de formula (4); iv) un grupo -COOR14 con R14 que es un grupo alquilo C1-4; v) un grupo -NH-CO-NR15R16 con R15 y R16 que son, independientemente entre sí, un átomo de hidrogeno, un grupo alquilo C1-4, un grupo fenilo, un grupo bencilo, y dichos grupos fenil y bencilo están substituidos, eventualmente, por uno o varios substituyentes elegidos entre un átomo de halogeno, un grupo alquilo C1-4 y un grupo alcoxi C1-4; vi) un grupo -SO2-NR1R18 con R17 y R18 que son, independientemente entre sí, un átomo de hidrogeno o un grupo alquilo C1-4; vii) un grupo -SO2- R19 con R19 que es un grupo alquilo C1-4 o un grupo arilo tal como fenilo; viii) un grupo heterociclilo elegido entre 1,3-dioxolanilo, imidazolilo, tetrazolilo, triazolilo eventualmente substituido por un grupo alquilo C1- 4, tiazolilo, pirimidinilo, oxadiazolilo, piridinilo, el imidazolilo está eventualmente substituido sobre el átomo de nitrogeno por un grupo alquilo C1-4 o un bencilo, el tetrazolilo está eventualmente substituido por un grupo alquilo C1-4 o un bencilo, el oxadiazolilo está eventualmente substituido por un alquilo C1-4; o ix) un grupo -NH-CO-OR15, donde R15 responde a la definicion anterior; en estado de base, de sal de adicion con un ácido, de hidrato o de solvato, en forma de enantiomeros, de diastereoisomeros, de rotámeros, de atropoisomeros o de sus mezclas.
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