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AR042423A1 - Diaril eteres como antagonistas del receptor opioide - Google Patents

Diaril eteres como antagonistas del receptor opioide

Info

Publication number
AR042423A1
AR042423A1 ARP030103376A ARP030103376A AR042423A1 AR 042423 A1 AR042423 A1 AR 042423A1 AR P030103376 A ARP030103376 A AR P030103376A AR P030103376 A ARP030103376 A AR P030103376A AR 042423 A1 AR042423 A1 AR 042423A1
Authority
AR
Argentina
Prior art keywords
alkyl
aryl
alkenyl
cycloalkyl
nitrogen
Prior art date
Application number
ARP030103376A
Other languages
English (en)
Original Assignee
Lilly Co Eli
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
Application filed by Lilly Co Eli filed Critical Lilly Co Eli
Publication of AR042423A1 publication Critical patent/AR042423A1/es

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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • C07D213/02—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
    • 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
    • C07D213/60—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 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07D213/02—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
    • 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
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
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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
    • C07D213/60—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 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
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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
    • C07D213/60—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 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
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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
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    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
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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
    • C07D213/60—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 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
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Abstract

Compuestos que son útiles para el tratamiento, prevención o mejora de la obesidad y las enfermedades relacionadas con la misma. Reivindicación 1: Un compuesto de fórmula (1), en la que: cada X1, X2, X3, X4, X5, X6, X7, X8, X9 y X10, es C, CH o N; con tal que cada anillo A o B no tenga más de 2 átomos de nitrógeno; E es O o NH; v es 1, 2 ó 3; R1 y R2 se seleccionan independientemente entre hidrógeno, alquilo C1-8, alquenilo C2-8, alquinilo C2-8, arilo, cicloalquilo C3-8, -(alquil C1-10)arilo, heterociclilo, -(alquil C1-10)heterocíclico, -arilheterociclilo, -(cicloalquil C3-8)heterociclilo, -(alquil C1-8)C(O)alquilo C1-8, arilC(O)(alquil C1-8)-, (cicloalquil C3-8)C(O)(CH2)n-, -(alquil C2-8)CH(OH)arilo, -(alquil C2-8)CH(OH)cicloalquilo, -(alquil C2-8)CH(OH)heterociclilo, (alquil C2-8)CH(OH)arilo, -(alquil C1-8)C(O)heterocíclico, -(alquil C1-8)C(O)arilo, (ariloxialquil C1-8)-, benzhidrilo, bicíclico, condensado, alquil (C1-8) bicíclico condensado, fenilC(O)-, fenilC(O)(alquil C1-8)-, alcoxi(C1-8)-alquil(C1-8)-, -CO(O)alquilo C1-8, -SO2alquilo C1-8, -SO2alquilarilo C1-10, -SO2(alquilC1-8)heterocíclico, -(alquil C1-8)cicloalquilo, -(CH2)nC(O)OR8, -(CH2)nC(O)R8, -(CH2)mC(O)NR8R8, y -(CH2)mNSO2R8; en la que cada grupo alquilo, alquenilo, cicloalquilo, heterocíclico, y arilo están opcionalmente sustituidos con de uno a cinco grupos seleccionados independientemente entre halo, haloalquilo C1-8, tioalquilo C1-8, alquilo C1-8, alquenilo C2-8, arilo, -(alquil C1-8)arilo, -C(O)alquilo C1-8, -SO2alquilo C1-8, -SO2(alquil C1-8)arilo, -SO2(alquil C1-8)heterocíclico, -(alquil C1-8)cicloalquilo, -(CH2)nC(O)OR8, -(CH2)nC(O)R8; y en el que R1 y R2 se pueden combinar entre sí opcionalmente o con 1 a 2 átomos adyacentes al átomo de nitrógeno para formar un heterociclo que contiene nitrógeno de 4, 5, 6 ó 7 miembros; dicho heterociclo que contiene nitrógeno puede tener también sustituyentes seleccionados del grupo constituido por amino, alquilo C1-8, alquenilo C2-8, alquinilo C2-8, arilo, (alquil C1-8)arilo, -C(O)alquilo C1-8, -CO(O)alquilo C1-8, halo, oxo, haloalquilo C1-8; y en la que R1 y R2 se pueden unir, independientemente, al anillo A para formar un heterociclo bicíclico que contiene nitrógeno de 4, 5, 6 ó 7 miembros; dicho heterociclo bicíclico que contiene nitrógeno puede tener también sustituyentes seleccionados del grupo constituido por oxo, amino, -alquil C1-8, -alquenil C2-8, -alquinil C2-8, arilo, -(alquil C1-8)arilo, -C(O)alquilo C1-8, -CO(O)alquilo C1-8, halo, y haloalquilo C1-8; y en la que R1 y R2 no son, simultáneamente, hidrógeno; y con tal que cuando v es 2, y R3 y R3' son ambos hidrógeno o CH3, y ambos anillos A y B son fenilo, entonces el grupo -NR1R2 no es igual a -NHCH2fenilo; y además con tal que cuando uno de R1 o R2 es -CH2CH2-fenilo opcionalmente sustituido o -CH2CH2-naftilo opcionalmente sustituido o -CH2CH2- aromático heterocíclico monocíclico opcionalmente sustituido de 5 ó 6 miembros, y v es 1, y ambos anillos A y B son fenilo, entonces R6 y R7 no son, simultáneamente, hidrógeno; R3 y R3' se seleccionan, cada uno independientemente, entre hidrógeno, alquilo C1-8, alquenilo C2-8, alquinilo C2-8, arilo, -(alquil C1-8)cicloalquilo, y -(alquil C1-8)arilo; R4 y R5 se seleccionan, cada uno independientemente, entre hidrógeno, alquilo C1-8, alquenilo C2-8, -alquinil C2-8, -(alcoxi C1-8)alquilo, tioalquilo C1-8, halo, haloalquilo C1-8, -(alcoxi C1-8)haloalquilo, arilo, -(alquil C1-8)arilo, -C(O)alquilo C1-8 o -C(O)Oalquilo C1-8, -(alquil C1-8)amino, -(alquil C1-8)cicloalquilo, -(CH2)mC(O)alquilo C1-8, y (CH2)NR8R8, en la que cada R4 o R5 se une a su anillo respectivo sólo por átomos de carbono, y en la que y es 0, 1, 2 ó 3; y en la que z es 0, 1, 2 ó 3; R6 y R7 se seleccionan, cada uno independientemente, entre hidrógeno, alquilo C1-8, alquenilo C2-8, alquinilo C2-8, -C(O)alquilo C1-8, hidroxi, alcoxi C1-8, -SO2alquilo C1-8, SO2(alquil C1-8)arilo, -SO2(alquil C1-8)heterocíclico, arilo, -(alquil C1-8)arilo, cicloalquilo C3-7, -(alquil C1-6)cicloalquilo, -(CH2)nC(O)R8, -(CH2)mC(O)NR8R8, y -(CH2)mNSO2R8; en la que cada grupo alquilo, alquenilo, y arilo están opcionalmente sustituidos con de uno a cinco grupos seleccionados independientemente entre alquilo C1-8, alquenilo C2-8, arilo, y (alquil C1-8)arilo; y en el que R6 y R7 se pueden combinar, independientemente, entre sí y con el átomo de nitrógeno al que están unidos o con 1 a 2 átomos adyacentes al átomo de nitrógeno para formar un heterociclo que contiene nitrógeno de 4, 5, 6 ó 7 miembros; dicho heterociclo que contiene nitrógeno puede tener, opcionalmente, sustituyentes del grupo constituido por oxo, alquilo C1-8, alquenilo C2-8, alquinilo C2-8, arilo, (alquil C1-8)arilo, -C(O)alquilo C1-8, -CO(O)alquilo C1-8, hidroxi, alcoxi C1-8, -(alquil C1-8)amina, halo, y haloalquilo; R8 es hidrógeno, alquilo C1-8, alquenilo C2-8, (alquil C1-8)arilo, -C(O)alquilo C1-8 o -C(O)Oalquilo C1-8; y en la que n es 0, 1, 2, 3 ó 4 y m es 1, 2 ó 3; o una sal, solvato, enantiómero, racemato, diasterómero o mezcla de diasterómeros del mismo farmacéuticamente aceptable.
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