AR069543A1 - Derivados bis-(sulfonilamino), composiciones farmaceuticas que los contienen y su uso en terapia. - Google Patents

Derivados bis-(sulfonilamino), composiciones farmaceuticas que los contienen y su uso en terapia.

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Publication number
AR069543A1
AR069543A1 ARP080104976A ARP080104976A AR069543A1 AR 069543 A1 AR069543 A1 AR 069543A1 AR P080104976 A ARP080104976 A AR P080104976A AR P080104976 A ARP080104976 A AR P080104976A AR 069543 A1 AR069543 A1 AR 069543A1
Authority
AR
Argentina
Prior art keywords
alkyl
alkynyl
alkenyl
alkylheterocyclyl
alkylheteroaryl
Prior art date
Application number
ARP080104976A
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English (en)
Original Assignee
Astrazeneca Ab
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 Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of AR069543A1 publication Critical patent/AR069543A1/es

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    • 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
    • C07D405/04—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
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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
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/51—Y being a hydrogen or a carbon atom
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—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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    • 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
    • C07D213/24—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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    • 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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    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
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    • C07D307/18—Heterocyclic compounds containing five-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
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    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
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    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
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    • 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
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    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
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Abstract

Compuestos, e isomeros opticos, racematos y tautomeros de los mismos, y sales farmacéuticamente aceptables de los mismos; junto con procesos para su preparacion, composiciones farmacéuticas que las contienen y su uso en terapia, Los compuestos son inhibidores de la prostaglandina E sintasa-1 microsomal. Reivindicacion 1: Un compuesto de formula (1) o una sal farmacéuticamente aceptable del mismo donde: A es seleccionado de aril mono y bicíclico, heteroaril mono y bicíclico, cicloalquenil y heterociclil mono y bicíclico; R1 es independientemente seleccionado de halogeno, nitro, SF5, CHO, alquil C0-6CN, Oalquil C1-6CN, alquil C0-6OR5, Oalquil C2-6OR5, alquil C0-6NR5R6, Oalquil C2-6NR5R6, Oalquil C2-6Oalquil C2-6NR5R6, alquil C0-6CO2R5, Oalquil C1-6CO2R5, aIquil C0-6CON(R5)2, Oalquil C1-6CON(R5)2, Oalquil C2-6-NR5(CO)R6, alquil C0-6NR5(CO)R6, O(CO)NR5R6, NR5(CO)OR6, NR5(CO)NR5R6, O(CO)OR5, O(CO)R5, aIquil C0-6COR5, Oalquil C1-6COR5, NR5(CO)(CO)R5, NR5(CO)(CO)NR5R6, alquil C0-6SR5, alquil C0-6(SO2)NR5R6, oalquil C1-6NR5(SO2)R6, Oalquil C0-6(SO2)NR5R6, alquil C0-6(SO)NR5R6, Oalquil C1-6(SO)NR5R6, alquil C0-6OSO2R5, alquil C0-6NR5(SO2)NR5R6, alquil C0-6NR5(SO)R6, Oalquil C2-6NR5(SO)R6, Oalquil C1-6SO2R5, aIquil C0-6SO2R5, alquil C0-6SOR5, alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6 y alquilheterociclil C0-6, donde dicho alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6 y alquilheterociclil C0-6 es opcionalmente sustituido con uno o más B, y donde cualquiera de los grupos aril o heteroaril individuales pueden ser opcionalmente fusionados con un grupo cicloalquil, cicloalquenil o heterociclil de 4, 5, 6 o 7 miembros para formar un sistema de anillos bicíclicos donde el sistema de anillos bicíclicos es opcionalmente sustituido con uno o más B; R2 es -L1-G1-L2-G2; R3 hidrogeno; G1 es seleccionado de cicloalquil C3-10, cicloalquenil C4-12, cicloalquinil C7-12, aril, heteroaril, heterociclil, donde dicho cicloalquil C3-10, cicloalquenil C4-12, cicloalquinil C7-12, aril, heteroaril o heterociclil es opcionalmente sustituido con uno o más R10; G2 es seleccionado de hidrogeno, cicloalquil C3-8, cicloalquenil C4-12, cicloalquinil C7-12, aril, heteroaril, heterociclil, donde dicho cicloalquil C3-8, cicloalquenil C4-12, cicloalquinil C7-12, aril, heteroaril o heterociclil es opcionalmente sustituido con uno o más R10; en cada caso, R5 es independientemente seleccionado de hidrogeno, alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6 y alquilheterociclil C0-6, donde dicho alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6 o alquilheterociclil C0-6 es opcionalmente sustituido con uno o más B; en cada caso, R6 es seleccionado de hidrogeno, alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6OR5, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6 y alquilheterociclil C0-6, donde dicho alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6 o alquilheterociclil C0-6 es opcionalmente sustituido con uno o más B; o R5 y R6 pueden junto con el átomo o átomos de enlace a los cuales están enlazados formar un anillo heterocíclico de 4 a 6 miembros que contiene uno o más heteroátomos seleccionados de N, O o S que es opcionalmente sustituido con B; siempre que dos grupos R5 se encuentren en la estructura entonces pueden opcionalmente junto con el átomo o átomos de enlace a los cuales están enlazados formar un anillo heterocíclico de 5 o 6 miembros que contiene uno o más heteroátomos seleccionados de N, O o S, que es opcionalmente sustituido con uno o más B; L1 y L2 independientemente representan un enlace o un grupo de enlace no cíclico de 1-7 miembros que contiene 0-2 heteroátomos seleccionados de O, N, y S, dicho grupo de enlace opcionalmente conteniendo CO, S(O)n, C=C o un grupo acetilénico, y opcionalmente siendo sustituido con uno o más R8; R8 es seleccionado de halogeno, nitro, CHO, CN, OH, Oalquil C1-6, O-alquil C1-6Oalquil C1-6, alquil C1-6, alquenil C2-6, alquinil C2-6, Nalquil C1-6-alquil C1-6, NH2, NHalquil C1-6, S(O)nalquil C1-6, SO2Nalquil C1-6-alquil C1-6, SO2NH2, SO2NHalquil C1-6, CF3, CHF2, CFH2, C(O)alquil C1-6, C(O)Nalquil C1-6-alquil C1-6, C(O)NHalquil C1-6, C(O)NH2, Nalquil C1-6(CO)N-aIquil C1-6-alquil C1-6, NH(CO)N-alquil C1-6-aIquil C1-6, N-alquil C1-6-(CO)NH-alquil C1-6, NH(CO)NH2, N-alquil C1-6-(CO)NH2;.siempre que dos grupos R8 estén unidos al mismo átomo del grupo de enlace L1, pueden opcionalmente juntos formar un anillo no aromático, carbocíclico o heterocíclico (que contienen uno o más heteroátomos seleccionados de N, O o S) de 3 a 6 miembros, que es opcionalmente sustituido con uno o más R9; R9 es seleccionado de halogeno, nitro, CHO, CN, OH, OaIquil C1-6, OaIquil C1-6Oalquil C1-6, alquil C1-6, alquenil C2-6, alquinil C2-6, Nalquil C1-6-alquil C1-6, NH2, NHalquil C1-6, S(O)nalquil C1-6, SO2Nalquil C1-6-alquil C1-6, SO2NH2, SO2NHalquil C1-6, CF3, CHF2, CFH2, C(O)alquil C1-6, C(O)Nalquil C1-6-alquil C1-6, C(O)NHalquil C1-6, C(O)NH2, Nalquil C1-6(CO)N-aIquil C1-6-alquil C1-6, NH(CO)N-alquil C1-6-aIquil C1-6, N-alquil C1-6-(CO)NH-alquil C1-6, NH(CO)NH2, N-alquil C1-6-(CO)NH2; B es seleccionado de halogeno, nitro, SF5, OSF5, CN, Oalquil C2-6NR15R16, NR15R16, CONR15R16, NR15(CO)R16, O(CO)alquil C1-6, (CO)Oalquil C1-6, COR15, (SO2)NR15R16, NR15SO2R15, SO2R15, SOR15, (CO)alquil C1-6NR15R16, (SO2)alquil C1-6NR15R16, OSO2R15, alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6 y alquilheterociclil C0-6, R15 es seleccionado de hidrogeno, alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6 y alquilheterociclil C0-6, R16 es seleccionado de hidrogeno, alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6OR5, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6 y alquilheterociclil C0-6, o R15 y R16 pueden junto con el átomo o átomos de enlace a los cuales están enlazados formar un anillo heterocíclico de 4 a 6 miembros que contienen uno o más heteroátomos seleccionados de N, O o S; siempre que dos grupos R15 se encuentren en la estructura entonces pueden opcionalmente junto con el átomo o átomos de enlace a los cuales están enlazados formar un anillo heterocíclico de 5 o 6 miembros que contiene uno o más heteroátomos seleccionados de N, O o S; D es seleccionado de halogeno, nitro, SF5, OSF5, CN, OR13, Oalquil C2-6NR13R14, NR13R14, CONR13R14, NR13(CO)R14, O(CO)alquil C1-6; (CO)Oalquil C1-6, COR13, (SO2)NR13R14, NR13SO2R14, SO2R13, SOR13, (CO)alquil C1-6NR13R14, (SO2)alquil C1-6NR13R14, OSO2R13, alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, y alquilheterociclil C0-6; R10 es independientemente seleccionado de halogeno, nitro, SF5, OSF5, CN, OR11 C:::CR11, Oalquil C2-6NR11R12, NR11R12, CONR11R12, NR11(CO)R12, O(CO)alquil C1-6, (CO)Oalquil C1-6, COR11, (SO2)NR11R12, NR11SO2R11, SO2R11, SOR11, (CO)alquil C1-6NR11R12, (SO2)alquilC1-6NR11R12, OSO2R11, alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6, alquilheterociclil C0-6 y Oalquil C2-6alquilheterociclil, donde dicho alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6, alquilheterociclil C0-6 u Oalquil C2-6alquilheterociclil es opcionalmente sustituido con uno o más E, y donde cualquiera de los grupos aril o heteroaril individuales pueden ser opcionalmente fusionados con un grupo cicloalquil, cicloalquenil o heterociclil de 4, 5, 6 o 7 miembros para formar un sistema de anillos bicíclicos donde el sistema de anillos bicíclicos es opcionalmente sustituido con uno o más E; en cada caso, R11 es independientemente seleccionado de hidrogeno, alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6, y alquilheterociclil C0-6, donde cualquiera de los grupos alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6, y alquilheterociclil C0-6, individuales pueden ser opcionalmente sustituidos con uno o más E; R12 es seleccionado de hidrogeno, alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6, y alquilheterociclil C0-6, donde cualquiera de los grupos alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6, y alquilheterociclil C0-6, individuales pueden ser opcionalmente sustituidos con uno o más E; R11 y R12 pueden junto con el átomo o átomos de enlace a los cuales están enlazados formar un anillo heterocíclico de 4 a 6 miembros que contiene uno o más heteroátomos seleccionados de N, O o S que es opcionalmente sustituido con B; siempre que dos grupos R11 se encuentren en la estructura entonces pueden opcionalmente junto con el átomo o átomos de enlace a los cuales están enlazados formar un anillo heterocíclico de 5 o 6 miembros que contiene uno o más heteroátomos seleccionados de N, O o S, donde el sistema de anillos es opcionalmente sustituido con uno o más E; R13 es independientemente seleccionado de hidrogeno, alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6 y alquilheterociclil C0-6; R14 es seleccionado de hidrogeno, alquil C1-6, alquenil C2-6, alquinil C2-6, alquil C0-6OR5, alquil C0-6-cicloalquil C3-8, alquilaril C0-6, alquilheteroaril C0-6 y alquilheterociclil C0-6; o R13 y R14 pueden junto con el átomo o átomos de enlace a los cuales están enlazados formar un anillo heterocíclico de 4 a 6 miembros que contiene uno o más heteroátomos seleccionados de N, O o S; siempre que dos grupos R13 se encuen
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