AR036597A1 - Derivados de 1h-imidazol que tienen actividad agonista de cb1, agonista parcial de cb1 o antagonista de cb1 - Google Patents

Derivados de 1h-imidazol que tienen actividad agonista de cb1, agonista parcial de cb1 o antagonista de cb1

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Publication number
AR036597A1
AR036597A1 ARP020103507A ARP020103507A AR036597A1 AR 036597 A1 AR036597 A1 AR 036597A1 AR P020103507 A ARP020103507 A AR P020103507A AR P020103507 A ARP020103507 A AR P020103507A AR 036597 A1 AR036597 A1 AR 036597A1
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Argentina
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group
whose
alkyl
substituted
cyano
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ARP020103507A
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English (en)
Inventor
Josephus H M Lange
Cornelis G Kruse
Jacobus Tipker
Arnoldus H J Herremans
Stuivenberg Herman H Van
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Solvay Pharm Bv
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Publication of AR036597A1 publication Critical patent/AR036597A1/es

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    • C07D295/22—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 with hetero atoms directly attached to ring nitrogen atoms
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    • C07D295/30—Nitrogen atoms non-acylated
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Abstract

Derivados de 1H-imidazol, métodos para la preparación de estos compuestos, y composiciones farmacéuticas que contienen uno o más de estos compuestos como un componente activo. Estos derivados de 1H-imidazol son potentes agonistas, agonistas parciales o antagonistas de receptores CB1 de cannabinoides con utilidad para el tratamiento de desórdenes psiquiátricos y neurológicos, así como otras enfermedades que involucran neurotransmisión cannabinoide. Los compuestos tienen la fórmula general (1), en donde: R representa fenilo, tienilo, 2-piridinilo, 3-piridinilo, 4-piridinilo, pirimidinilo, pirazinilo piridazinilo o triazinilo, cuyos grupos pueden estar sustituidos con 1, 2, 3 ó 4 sustituyentes Y, los cuales pueden ser iguales o diferentes, del grupo alquilo o alcoxi C1-3, hidroxi, halógeno, trifluorometilo, trifluorometiltio, trifluorometoxi, nitro, amino, mono- o dialquil C1-2-amino, mono o dialquil C1-2-amido, alcoxi C1-3-carbonilo, carboxilo, ciano, carbamoílo, y acetilo, o R representa naftilo, con la condición de que cuando R es 4-piridinilo, R4 representa un átomo de halógeno o un grupo ciano, carbamoílo, formilo, acetilo, trifluoroacetilo, fluoroacetilo, propionilo, sulfamoílo o alquilo C1-4 ramificado o no ramificado, cuyo grupo alquilo C1-4 puede estar sustituido con 1-3 átomos de flúor o con un grupo bromo, cloro, iodo, ciano o hidroxi; R1 representa fenilo o piridinilo cuyos grupos pueden estar sustituidos con 1-4 sustituyentes Y, los que pueden ser iguales o diferentes, en donde Y tiene el significado mencionado anteriormente, o R1 representa pirimidinilo, pirazinilo, piridazinilo o triazinilo, cuyos grupos pueden estar sustituidos con 1-2 sustituyentes Y, los cuales pueden ser iguales o diferentes o R1 representa un anillo heterocíclico aromático de 5 miembros que tiene uno o dos heteroátomos del grupo (N, O, S), cuyos heteroátomos pueden ser iguales o diferentes, cuyo anillo heterocíclico aromático de 5 miembros puede estar sustituido con 1-2 sustituyentes Y, los cuales pueden ser iguales o diferentes o R1 representa naftilo; R2 representa H, alquilo C1-8 ramificado o no ramificado, cicloalquilo C3-8, alquenilo C3-8, cicloalquenilo C5-8, cuyos grupos pueden contener un átomo de azufre, oxígeno o nitrógeno; R3 representa un grupo alquilo C2-8 ramificado o no ramificado, alcoxi C1-8, cicloalquiloxi C5-8, cicloalquilo C3-8, bicicloalquilo C3-10, tricicloalquilo C3-10, alquenilo C3-8, cicloalquenilo C5-8, cuyos grupos pueden opcionalmente contener uno o más heteroátomos del grupo (O, N, S) y cuyos grupos pueden estar sustituidos con un grupo hidroxi o 1-2 grupos alquilo C1-3 ó 1-3 átomos de flúor, o R3 representa un grupo bencilo o fenetilo cuyos anillos aromáticos pueden estar sustituidos con 1-5 sustituyentes Z, los cuales pueden ser iguales o diferentes, del grupo alquilo o alcoxi C1-3, hidroxi, halógeno, trifluorometilo, trifluorometiltio, trifluorometoxi, nitro, amino, mono- o dialquil C1-2-amino, mono o dialquil C1-2-amido, alquil C1-3 sulfonilo, dimetilsulfamido, alcoxi C1-3-carbonilo, carboxilo, trifluorometilsulfonilo, ciano, carbamoílo, sulfamoílo y acetilo, o R3 representa un grupo fenilo o piridinilo, cuyos grupos están sustituidos con 1-4 sustituyentes Z, en donde Z tiene el significado indicado anteriormente, o R3 representa un grupo piridinilo, o R3 representa un grupo fenilo, con la condición de que R4 representa un átomo de halógeno o un grupo ciano, carbamoílo, formilo, acetilo, trifluoroacetilo, fluoroacetilo, propionilo, sulfamoílo o alquilo C1-4, cuyo grupo alquilo C1-4 puede estar sustituido con 1-3 átomos de flúor o con un grupo bromo, cloro, iodo, ciano o hidroxi, o R3 representa un grupo NR5R6 con la condición que R2 representa un átomo de hidrógeno o un grupo metilo, en donde: R5 y R6 son iguales o diferentes y representan alquilo C1-4 ramificado o no ramificado, o R5 y R6 juntos con el átomo de nitrógeno al cual están ligados, forman un grupo heterocíclico monocíclico o bicíclico, saturado o no saturado, que tiene 4 a 10 átomos de anillo cuyo grupo heterocíclico contiene uno o dos heteroátomos del grupo (N, O, S), cuyos heteroátomos pueden ser iguales o diferentes, cuyo grupo heterocíclico puede estar sustituido con un grupo alquilo C1-3 o un grupo hidroxi, o R2 y R3 junto con el átomo de nitrógeno al cual están unidos, forman un grupo heterocíclico saturado o no saturado que tiene 4 a 10 átomos de anillo, cuyo grupo heterocíclico contiene uno o dos heteroátomos del grupo (N, O, S), cuyos heteroátomos pueden ser iguales o diferentes, cuyo grupo heterocíclico puede estar sustituido con un grupo alquilo C1-3 o un grupo hidroxi; R4 representa un átomo de hidrógeno o halógeno o un grupo ciano, carbamoílo, formilo, acetilo, trifluoroacetilo, fluoroacetilo, propionilo, sulfamoílo o alquilo C1-4 ramificado o no ramificado, cuyo grupo alquilo C1-4 puede estar sustituido con 1-3 átomos de flúor o con un grupo bromo, cloro, iodo, ciano o hidroxi; y prodrogas, estereoisómeros y sales del mismo.
ARP020103507A 2001-09-21 2002-09-18 Derivados de 1h-imidazol que tienen actividad agonista de cb1, agonista parcial de cb1 o antagonista de cb1 AR036597A1 (es)

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EP (1) EP1438296B1 (es)
JP (1) JP4393869B2 (es)
KR (1) KR100950431B1 (es)
CN (2) CN1556703A (es)
AR (1) AR036597A1 (es)
AT (1) ATE415391T1 (es)
AU (1) AU2002337106B2 (es)
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