ES2354569T3 - Antagonistas del receptor de histamina-3. - Google Patents

Antagonistas del receptor de histamina-3. Download PDF

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ES2354569T3
ES2354569T3 ES06765575T ES06765575T ES2354569T3 ES 2354569 T3 ES2354569 T3 ES 2354569T3 ES 06765575 T ES06765575 T ES 06765575T ES 06765575 T ES06765575 T ES 06765575T ES 2354569 T3 ES2354569 T3 ES 2354569T3
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Travis T. Wager
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Pfizer Products Inc
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Pfizer Products Inc
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    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring

Abstract

Un compuesto de fórmula Ia o Ib **Fórmula** o una sal farmacéuticamente aceptable del mismo, o el isómero cis, el isómero trans, o una mezcla de isómeros cis y trans, en las que: R1 se selecciona entre el grupo que consiste en OR4 y NR2R3; cada uno de R2 y R3 se selecciona independientemente entre el grupo que consiste en hidrógeno; alquilo C1-C8 opcionalmente sustituido con 1 a 4 halógenos; grupo alquilo C1-C4 opcionalmente sustituido con un sustituyente seleccionado entre el grupo que consiste en OH, de uno a cuatro alquilo C1-C4, cicloalquilo C3-C7, dialquilamino C1-C4, arilo C6-C14 opcionalmente sustituido con un halógeno o ariloxi C6-C10 opcionalmente sustituido con uno a dos halógenos, y heteroarilo de 5-10 miembros opcionalmente sustituido con un grupo arilo C6-C10 y opcionalmente sustituido con uno a tres grupos alquilo C1-C4; cicloalquilo C3-C7; arilo C6-C14; heterocicloalquilo de 3-8 miembros opcionalmente sustituido con uno o más grupos alquilcarbonilo C1-C4; arilsulfonilo C6-C10 opcionalmente sustituido con uno o más alquilo C1-C2; heteroarilo de 5-10 miembros; aril C6-C14-alquileno C0-C4-O-alquilo C0-C4, en el que cada alquilo C0-C4 y cada alquileno C0-C4 está opcionalmente sustituido con uno a cuatro alquilo C1-C4; -C(=O)R3, -S(O)2R3'; en el que R3' se selecciona entre el grupo que consiste en hidrógeno, alquilo (C1-C4), alquenilo (C1-C4), arilo, heteroarilo, cicloalquilo (C3-C7), cicloheteroalquilo (C3-C7), y en el que cada hidrógeno en R3' puede estar opcionalmente sustituido independientemente con halo, alquilo (C1-C4), alquenilo (C2-C4) y -S(O)2CH3; en el que R3 25 puede seleccionarse adicionalmente entre el grupo que consiste en arilcarbonil C6-C14-arilo C6-C14; arilcarbonil C6-C14-heterocicloalquilo de 3-8 miembros; cicloalquilcarbonil C3- C8-arilo C6-C14; cicloalquilcarbonil C3-C8-heterocicloalquilo de 3-8 miembros; heterocicloalquilcarbonilo de 3- 8 miembros-arilo C6-C14; y heterocicloalquilcarbonil de 3-8 miembros-heterocicloalquilo 3-8 miembros; o R3 y R2 junto con el nitrógeno del grupo NR2R3 forman un primer anillo alifático de 5, 6 ó 7 miembros, en el que uno de los carbonos en el primer anillo alifático de 5, 6 ó 7 miembros está reemplazado opcionalmente por O, S, NR2' o CO, y el primer anillo alifático de 5, 6 ó 7 miembros está condensado con un arileno C6-C10 y está opcionalmente sustituido en un carbono del anillo con un sustituyente seleccionado entre el grupo que consiste en heteroarilo de 5-10 miembros opcionalmente sustituido con uno o más halógenos y opcionalmente sustituido con uno o más alquilo C1-C2, alcoxi C1-C4 opcionalmente sustituido con uno o más alcoxi C1-C2 y opcionalmente sustituido con uno o más dialquilaminocarbonilo C1-C4, y uno o dos alquilo C1-C4 opcional e independientemente sustituidos con uno o más alcoxi C1-C2; en las que R2' es hidrógeno; alquilo C1-C8 opcionalmente sustituido con 1 a 4 halógenos; heteroarilo de 5-10 miembros opcionalmente sustituido con un sustituyente seleccionado entre el grupo qu5 e consiste en halógeno, alquilo C1-C4, alcoxi C1-C2, arilo C6-C10, alquilaminocarbonilo C1-C4, y ciano; grupo alquilo C1-C4 opcionalmente sustituido con un sustituyente seleccionado entre el grupo que consiste en alcoxi C1-C2-carbonilo, heteroarilo de 5-10 miembros opcionalmente sustituido con uno o más alquilo C1- C2, de uno a cuatro alquilo C1-C4, cicloalquilo C3-C7 y arilo C6-C14; arilo C6-C10 opcionalmente sustituido con uno o dos alquilo C1-C2; alquilcarbonilo C1-C4; o aril C6-C14-alquileno C0-C4-O-alquilo C0-C4, en el que cada alquilo C0-C4 y cada alquileno C0-C4 está opcionalmente sustituido con uno a cuatro alquilo C1-C4; alquilsulfonilo C1-C4 R4 es hidrógeno o metilo; cada uno de R5 y R6 se selecciona independientemente entre el grupo que consiste en hidrógeno; grupo alquilo C1-C4 opcionalmente sustituido con un sustituyente seleccionado entre el grupo que consiste en OH, alquilo C1-C3, alcoxi C1-C3; o R5 y R6 junto con el nitrógeno al que están unidos forman una amina cíclica de 3-7 miembros opcionalmente sustituida con uno o más alquilo C1-C4; R7 es independientemente hidrógeno o metilo; n es 1, 2 ó 3; m es 1, 2 ó 3; Z se selecciona independientemente entre el grupo que consiste en hidrógeno, halógeno, alquilo C1-C4, alcoxi C1-C4 y -C(H)=CH2; o en la que, cuando m es 2 y ambos Z son -C(H)=CH2, ambos Z junto con 2 carbonos adyacentes o el anillo de fenilo de fórmula I forman un anillo aromático de 6 miembros condensado con dicho anillo de fenilo.
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