AR039257A1 - Derivados de benzamida - Google Patents
Derivados de benzamidaInfo
- Publication number
- AR039257A1 AR039257A1 ARP030101185A ARP030101185A AR039257A1 AR 039257 A1 AR039257 A1 AR 039257A1 AR P030101185 A ARP030101185 A AR P030101185A AR P030101185 A ARP030101185 A AR P030101185A AR 039257 A1 AR039257 A1 AR 039257A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- carbamoyl
- amino
- sulfamoyl
- optionally substituted
- Prior art date
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—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
- C07D239/26—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A61P35/00—Antineoplastic agents
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by 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
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
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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
- C07D213/60—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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D239/24—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
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/20—Nitrogen atoms
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- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
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- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by 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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- C07D295/04—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 substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- 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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- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- C07D401/12—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 linked by a chain containing hetero atoms as chain links
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- C07D403/12—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 linked by a chain containing hetero atoms as chain links
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- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
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- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Abstract
Derivados de benzamida, procesos para su preparación, composiciones farmacéuticas que los contienen y su uso en el tratamiento de enfermedades y trastornos clínicos mediados por la histona deacetilasa. Reivindicación 1: Un compuesto caracterizado porque responde a la fórmula (1) donde el anillo A es un heterociclilo, donde si dicho heterociclilo contiene una porción -NH- dicho N puede ser opcionalmente sustituido por un grupo seleccionado entre K; R1 es un sustituyente sobre C y se selecciona entre halo, nitro, ciano, hidroxi, trifluorometilo, trifluorometoxi, amino, carboxi, carbamoilo, mercapto, sulfamoilo, (C1-6) alquilo, (C2-6) alquenilo, (C2-6) alquinilo, (C1-6) alcoxi, (C1-6) alcanoilo, (C1-6) alcanoiloxi, N-(C1-6 alquil) amino, N,N-(C1-6 alquil)2amino, C1-6 alcanoilamino, N-(C1-6alquil)carbamoilo, N,N-(C1-6alquil)2carbamoilo, (C1-6) alquilS(O)a donde a es entre 0 y 2, C1-6 alcoxicarbonilo, N-(C1-6 alquil)sulfamoilo, N,N-(C1-6 alquil)2sulfamoilo, arilo, ariloxi, aril(C1-6)alquilo, grupo heterocíclico, (grupo heterocíclico) C1-6 alquilo, o un grupo (B-E); donde R1, incluyendo el grupo (B-E), puede ser opcionalmente sustituido sobre C por uno o más W; y donde si dicho grupo heterocíclico contiene una porción -NH- dicho N puede ser opcionalmente sustituido por J; W es halo, nitro, ciano, hidroxi, trifluorometilo, trifluorometoxi, amino, carboxi, carbamoilo, mercapto, sulfamoilo, C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C1-6 alcoxi, C1-6 alcanoilo, C1-6 alcanoiloxi, N-(C1-6 alquil)amino, N,N-(C1-6alquil)2amino, C1-6 alcanoilamino, N-(C1-6alquil)carbamoilo, N,N-(C1-6alquil)2carbamoilo, C1-6 alquilS(O)a donde a es entre 0 y 2, C1-6 alcoxicarbonilo, N-(C1-6alquil)sulfamoilo, N,N-(C1-6alquil)2sulfamoilo, o un grupo (B'-E'-); donde W, incluyendo el grupo (B'-E'-), puede ser opcionalmente sustituido sobre C por uno o más Y; Y y Z se seleccionan en forma independiente entre halo, nitro, ciano, hidroxi, trifluorometilo, trifluorometoxi, amino, carboxi, carbamoilo, mercapto, sulfamoilo, C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C1-6 alcoxi, C1-6 alcanoilo, C1-6 alcanoiloxi, N-(C1-6 alquil) amino, N,N-(C1-6 alquil)2amino, C1-6 alcanoilamino, N-(C1-6 alquil)carbamoilo, N,N-(C1-6 alquil)2carbamoilo, C1-6 alquilS(O)a, donde a es entre 0 y 2, C1-6 alcoxicarbonilo, N-(C1-6alquil)sulfamoilo o N,N-(C1-6 alquil)2 sulfamoilo; G, J, y K se seleccionan en forma independiente entre C1-8 alquilo, C2-8 alquenilo, C1-8 alcanoilo, C1-8 alquilsulfonilo, C1-8 alcoxicarbonilo, carbamoilo, N-(C1-8 alquil) carbamoilo, N,N-(C1-8 alquil)carbamoilo, benciloxicarbonilo, benzoilo, fenilsulfonilo, arilo, aril(C1-6)alquilo o (grupo heterocíclico)C1-6 alquilo; donde G, J y K pueden ser opcionalmente sustituidos sobre C por uno o más Q; y donde si dicho grupo heterocíclico contiene una porción -NH- dicho N puede ser opcionalmente sustituido por H o C1-6 alquilo; Q es halo, nitro, ciano, hidroxi, trifluorometilo, trifluorometoxi, amino, carboxi, carbamoilo, mercapto, sulfamoilo, C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C1-6 alcoxi, C1-6 alcanoilo, C1-6 alcanoiloxi, N-(C1-6 alquil)amino, N,N-(C1-6 alquil)2amino, C1-6 alcanoilamino, N-(C1-6 alquil)carbamoilo, N,N-(C1-6 alquil)2carbamoilo, C1-6 alquil S(O)a donde a es entre 0 y 2, C1-6 alcoxicarbonilo, C1-6 alcoxicarbonilamino, N-(C1-6 alquil)sulfamoilo, N,N-(C1-6 alquil)2sulfamoilo, arilo, ariloxi, arilo C1-6 alquilo, aril C1-6alcoxi, grupo heterocíclico, (grupo heterocíclico)C1-6 alquilo, (grupo heterocíclico)C1-6 alcoxi o un grupo (B"-E"-); donde Q, incluyendo el grupo (B"-E"-), puede ser opcionalmente sustituido sobre C por uno o más Z; B, B' y B" se seleccionan en forma independiente entre C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C3-8 cicloalquilo, C3-8cicloalquil(C1-6)alquilo, arilo, aril C1-6 alquilo, grupo heterocíclico, (grupo heterocíclico)C1-6 alquilo, fenilo o fenil C1-6 alquilo; donde B, B', y B" pueden ser opcionalmente sustituidos sobre C por uno o más D; y donde si dicho grupo heterocíclico contiene una porción -NH- dicho N puede ser opcionalmente sustituido por un grupo seleccionado entre G; E, E', y E" se seleccionan en forma independiente entre -N(Ra)-, -O-, -C(O)O-, -OC(O)-, -C(O)-, -N(Ra)C(O)-, -N(Ra)C(O)N(Rb)-, -N(Ra)C(O)O-,-OC(O)N(Ra)-, -C(O)N(Ra), -S(O)r-, SO2N(Ra)-, -N(Ra)SO2-, donde Ra y Rb se seleccionan en forma independiente entre H o alquilo C1-6 opcionalmente sustituido por uno o más F y r es 0-2; D y F se seleccionan en forma independiente entre halo, nitro, ciano, hidroxi, trifluorometilo, trifluorometoxi, amino, carboxi, carbamoilo, mercapto, sulfamoilo, C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C1-6 alcoxi, C1-6 alcanoilo, C1-6 alcanoiloxi, N-(C1-6 alquil)amino, N,N-(C1-6 alquil)2amino, C1-6 alcanoilamino, N-(C1-6 alquil)carbamoilo, N,N-(C1-6 alquil)2 carbamoilo, C1-6 alquil S(O)a donde a es entre 0 y 2, C1-6 alcoxicarbonilo, N-(C1-6 alquil)sulfamoilo o N,N-(C1-6alquil)2sulfamoilo; m es 0, 1, 2, 3 o 4; donde los valores de R1 pueden ser iguales o diferentes; R2 es halo; n es 0, 1 o 2; donde los valores de R2 pueden ser iguales o diferentes; R3 es amino o hidroxi; R4 es halo, nitro, ciano, hidroxi, trifluorometilo, trifluorometoxi, amino, carboxi, carbamoilo, mercapto, sulfamoilo, C1-3 alquilo, C2-3 alquenilo, C2-3 alquinilo, C1-3alcoxi, C1-3alcanoilo, C1-3 alcanoiloxi, N-(C1-3 alquil)amino, N,N-(C1-3 alquil)2 amino, C1-3 alcanoilamino, N-(C1-3 alquil)carbamoilo, N,N-(C1-3 alquil)2carbamoilo, C1-3 alquil S(O)a donde a es entre 0 y 2, C1-3 alcoxicarbonilo, N-(C1-3 alquil)sulfamoilo, N,N-(C1-3 alquil)2sulfamoilo; p es 0, 1 o 2; donde los valores de R4 pueden ser iguales o diferentes; o una sal aceptable para uso farmacéutico o éster hidrolizable in vivo o amida del mismo; con la salvedad de que dicho compuesto no es N-(2-amino-6-hidroxifenil)-4-(1-metilhomopiperazin-4-il)benzamida; N-(2-amino-6-metilfenil)-4-(1-metilhomopiperazin-4-il)benzamida; N-(2-aminofenil)-4-(1-t-butoxicarbonilhomopiperazin-4-il)benzamida, o N-(2-aminofenil)-4-(1-metilhomopiperazin-4-il)benzamida.
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