AR045082A1 - Compuestos de aminobenzofenona y su uso en tratamientos terapeuticos - Google Patents

Compuestos de aminobenzofenona y su uso en tratamientos terapeuticos

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Publication number
AR045082A1
AR045082A1 ARP040102611A ARP040102611A AR045082A1 AR 045082 A1 AR045082 A1 AR 045082A1 AR P040102611 A ARP040102611 A AR P040102611A AR P040102611 A ARP040102611 A AR P040102611A AR 045082 A1 AR045082 A1 AR 045082A1
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AR
Argentina
Prior art keywords
alkyl
alkenyl
alkynyl
heterocyclyl
nrac
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Application number
ARP040102611A
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English (en)
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Leo Pharma As
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Publication of AR045082A1 publication Critical patent/AR045082A1/es

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    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/136—Amines having aromatic rings, e.g. ketamine, nortriptyline having the amino group directly attached to the aromatic ring, e.g. benzeneamine
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    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/16—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
    • C07C235/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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    • 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
    • C07C235/58—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 with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/64—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 with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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    • 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D405/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Abstract

La presente conforme a la fórmula (1), cuyos dichos compuestos, son útiles, por ejemplo, en el tratamiento de enfermedades inflamatorias y oftálmicas, o de cáncer. Reivindicación 1: Un compuesto de la fórmula general (1), donde: R1 es halógeno, hidroxi, mercapto, trifluormetilo, amino, alquilo C1-4, alquenilo C2-4, alquinilo C2-4, alcoxi C1-4, alquiltio C1-4, alquilamino C1-6, alcoxicarbonilo C1-4, ciano, -CONH2 o nitro; R2 es halógeno, hidroxi, mercapto, trifluorometilo, amino, alquilo C1-4, alquenilo C2-4, alquinilo C2-4, alcoxi C1-4, alquiltio C1-4, alquilamino C1-6, alcoxicarbonilo C1-4, ciano, -CONH2, fenilo o nitro; R3 representa uno o más sustituyentes iguales o diferentes seleccionados entre el grupo que consiste en hidrógeno, halógeno, hidroxi, mercapto, trifluorometilo, ciano, carboxi, CONH2, nitro, alquilo C1-4, alquenilo C2-4, alquinilo C2-4, alcoxi C1-4, alquiltio C1-4, alcoxicarbonilo C1-4; R4 es hidrógeno, halógeno, R8 o Y1R8; Y1 es -O-, -S-, -S(O)-, -S(O)2-, -NRa-, -NRaC(O)NRb-, NRaC(O)-, -C(O)NRa-, -C(O)NRaO-, -C(O)-, -C(O)O-, -NRaC(O)O-, -S(O)2NRa-, -NRaS(O)2-; Ra y Rb son iguales o diferentes, y cada uno representa hidrógeno, alquilo C1-4, alquenilo C2-4, alquinilo C2-4, carbociclilo C3-8, heterociclilo o arilo; R8 es hidrógeno, alquilo(C1-10)-heterociclilo, alquilo(C1-10)-carbociclilo(C3-12), alquilo C1-10, alquenilo C2-10, alquinilo C2-10, carbociclilo C3-12 o heterociclilo, cada uno está opcionalmente sustituido con uno o más sustituyentes iguales o deferentes representados por R7; R7 es halógeno, hidroxi, mercapto, trifluorometilo, amino, alquilo C1-4, alcoxi C1-4, alquiltio C1-4, alquilamino C1-6, alcoxicarbonilo C1-4, trialquilamonio C1-9 unido a un anión, ciano, azido, nitro, -COOH, -CONH2, -CONHR' o -CONRR', en donde R y R' son iguales o diferentes, y cada uno representa hidrógeno o alquilo C1-3; uno de R5 y R6 es Y2R9, alquilo(C1-6)-Y2R9, alquenilo(C1-6)-Y2R9, alquilo(C1-10)-heterociclilo, alquilo(C1-10)-carbociclilo(C3-12), alquilo C1-10, alquenilo C2-10, alquinilo C2-10, carbociclilo C3-12 o heterociclilo C3-12, cada uno está opcionalmente sustituido con uno o más sustituyentes iguales o diferentes representados por R7; y el otro es hidrógeno, halógeno, hidroxi, mercapto, trifluorometilo, amino, alquilo C1-4, alquenilo C2-4, alquinilo C2-4, alcoxi C1-4, alquiltio C1-4, alquilamino C1-6, alcoxicarbonilo C1-4, ciano, -CONH2 o nitro; con la condición de que cuando R5 o R6 es fenilo, alquilo C1-5 o alquenilo C2-3, está sustituido con uno o más sustituyentes iguales o diferentes representados por R7 (excepto flúor cuando R5 o R6 es metilo); Y2, es -O-, -S-, -S(O)-, -S(O)2-, -NRa-, -NRaC(O)NRb-, -NRaC(O)-, -C(O)NRa-, -C(O)NRaO-, -C(O)-, -NRaC(O)O- o -NRaS(O)2-; R9 es alquilo(C1-10)-heterociclilo), alquilo(C1-10)-carbociclilo(C3-12), alquilo C1-10, alquenilo C2-10, alquinilo C2-10, carbociclilo C3-12, heterociclilo, cada uno está opcionalmente sustituido con uno o más sustituyentes iguales o diferentes representados por R7, con la condición de que cuando Y2 es -O-, NRa-, o -S-, y R9 es alquilo C1-6, está sustituido con uno o más sustituyentes iguales o diferentes representados por R7; o cuando uno de R5 o R6 es el grupo -C(O)NRaR9, Ra y R9 junto con el átomo de nitrógeno al cual están unidos forman un anillo heterocíclico que opcionalmente comprende uno o más heteroátomos adicionales seleccionados entre el grupo que consiste en O, S y N, opcionalmente sustituidos con uno o más sustituyentes representados por R7; o una sal o éster farmacéuticamente aceptables de dicho compuesto.
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