AR047754A1 - Derivados de indol inhibidores de las polimerasas virales - Google Patents

Derivados de indol inhibidores de las polimerasas virales

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Publication number
AR047754A1
AR047754A1 ARP040100155A ARP040100155A AR047754A1 AR 047754 A1 AR047754 A1 AR 047754A1 AR P040100155 A ARP040100155 A AR P040100155A AR P040100155 A ARP040100155 A AR P040100155A AR 047754 A1 AR047754 A1 AR 047754A1
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Argentina
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alkyl
cycloalkyl
optionally substituted
aryl
het
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ARP040100155A
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English (en)
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Pierre Beaulieu
Christian Brochu
Catherine Chabot
Eric Jolicoeur
Stephen Kawai
Marc-Andre Poupart
Youla S Tsantrizos
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Boehringer Ingelheim Int
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Publication of AR047754A1 publication Critical patent/AR047754A1/es

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    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D209/30—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D401/06—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D405/04—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
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—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
    • C07D417/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Virology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Communicable Diseases (AREA)
  • Engineering & Computer Science (AREA)
  • Oncology (AREA)
  • Molecular Biology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Hydrogenated Pyridines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Indole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Un isomero, enantiomero, diastereomero o tautomero de un compuesto, representado por la formula (1) en la que: bien A o B es N y el otro B o A es C, en la que ----entre dos átomos de C representa u doble enlace y ----- entre un átomo C y un átomo N representa un enlace sencillo, el grupo -C(=Y1)-Z se une covalentemente a cualquier M2 o M3, M1 es CR4a, M2 o M3, cuando no se unen a -C(=Y1)-Z, es CR5, M4 es CR4b, y además uno o dos de los grupos seleccionados entre M1, M2, M3 y M4 también puede ser N, con la condicion de que Sp es un grupo espaciador seleccionado entre -(CR51R52)k1-, en el que k1 es 1, 2 o 3; R51, R52 son independientemente H, alquilo C1-6, cicloalquilo C3-7 o alquil C1-3-cicloalquilo C3-7, o R51 y R52 están covalentemente unidos juntos y al átomo de C al que se unen para formar un sistema cíclico saturado de 3, 4, 5, 6 o 7 eslabones o insaturado de 5, 6 o 7 eslabones en los que el sistema cíclico saturado o insaturado de 5, 6 o 7 eslabones contiene opcionalmente 1 a 3 heteroátomos seleccionados entre N, O o S; dicho alquilo, cicloalquilo, alquil-cicloalquilo o sistema cíclico estando opcionalmente sustituido con halogeno, hidroxi, alcoxi C1-6, ciano, amino, -NH (alquil C1-4) y/o -N(alquil C1-4)2; Yo es O, S, NR11 o CR12R13, en los que R11, R12, R13 se definen cada uno de ellos independientemente como Ro; R13 también puede ser COORo o SO2Rc; en los que Rc y cada Ro está opcionalmente sustituido con R150; o tanto R12 como R13 están covalentemente unidos juntos y al átomo de C al que se unen para formar un sistema cíclico saturado de 3, 4, 5, 6 o 7 eslabones o insaturado de 5, 6 o 7 eslabones en los que el sistema cíclico saturado o insaturado de 5, 6 o 7 eslabones contiene opcionalmente 1 a 3 heteroátomos seleccionados entre N, O o S; dichos sistemas cíclicos estando opcionalmente sustituidos con R150; L es alquilo C1-6, cicloalquilo C3-6, alquil C1-6-cicloalquilo C3-6, alquenilo C2-6, arilo, alquilo C1-4-arilo, Het, alquil C1-6-Het, todos los cuales están sustituidos con R60; o Yo y L están covalentemente unidos para formar un grupo mono de 5, 6, 7 u 8 eslabones o un grupo bicíclico de 8, 9, 10 u 11 eslabones que puede ser opcionalmente insaturado o aromático y que puede contener 1, 2 o 3 heteroátomos seleccionados entre N, O o S, en los que el grupo mono o bicíclico está opcionalmente sustituido con R60; o si Yo es CR12R13, entonces L también puede ser H; o si Yo es O, entonces L también puede ser ORc; en el que Rc está opcionalmente sustituido con R60; o si Yo es O, S o NR11 entonces L también puede ser N(RN2)RN1, NRN3-N(RN2)RN1, NRN3-NRN2-CO-Rc, NRN4-NRN3-CO-N(RN2)RN1, NRN2-SO2-Rc, NRN2-CO-Rc, NRN3-CO-N(RN2)RN1 o N(RN1)ORo; dicho RN1, incluyendo cualquier heterociclo o heterobiciclo formado por RN1, RN2 y/o RN3, y Rc y Ro estando opcionalmente sustituido con R60; o si Yo es O o S, entonces L también puede ser OR6a o N(R5a)R6a, en el que R5a se define como RN2, y en el que R6a es como se muestra en formula (2) o R6a es como se muestra en formula (3), en las que R7a y R8a se definen cada uno de ellos independientemente como Ro, COORo o CON(RN2)RN1, en el que dicho Ro está opcionalmente sustituido con R60; o R7a y R8a están covalentemente unidos juntos para formar un cicloalquilo C3-7 o a un heterociclo de 4, 5 o 6 miembros que tiene entre 1 y 3 heteroátomos seleccionados entre O, N y S; y cuando L es N(R5a)R6a, cualquiera de R7a o R8a puede estar covalentemente unido a R5a para formar un heterociclo de 5 o 6 eslabones que contiene N, en el que dicho cicloalquilo o heterociclo está opcionalmente sustituido con R150; y W1 se selecciona entre a) un enlace sencillo; b) -CH2-; c) -CH2-CH2-; y d) -CH=CH-; en el que los grupos alquileno y alquenileno segun b), c) y d) se pueden sustituir con alquilo C1-3; Y2 es O o S; R9a se define como Ro, en el que dicho Ro se sustituye opcionalmente con R60; o R9a está covalentemente unido a R7a o R8a para formar un heterociclo de 5 o 6 eslabones; Q1 es arilo, Het, alquil C1-6-arilo, alquil C1-6-Het, alquil C1-6-CONH-arilo o alquil C1-6-CONH-Het, todos los cuales están sustituidos con R60; Y1 es O, S o NR14, en el que R14 es H o alquilo C1-6, Z se define como a) Oro; b) SO2Rc; c) N(RN2)RN1; d) NRN3-N(RN2)RN1; e) NRN3-NRN2-CO-Rc; f) NRN4-NRN3-CO-N(RN2)RN1; g) NRN2-SO2-Rc; h) NRN3-SO2-N(RN2)RN1; i) NRN2-CO-Rc; j) COORo; k) N(RN1)ORo; en los que Ro y Rc están opcionalmente sustituidos con R60, y dicho RN1, incluyendo cualquier heterociclo o heterobiciclo formado por RN1, RN2, y/o RN3, estando opcionalmente sustituido con R60; o Z es OR6b o N(R5b)R6b en el que R5b se define como RN2 y R6b es como se muestra en formula (4) o R6b es como se muestra en formula (5) en el que R7b, R8b, Y3, R9b, W2 se definen como R7a, R8a, Y2, R9a, W1 respectivamente; y Q2 es arilo, Het, alquil C1-6-arilo, alquil C1-6-Het, alquil C1-6-CONH-arilo o alquil C1-6-CONH-Het, todos los cuales están sustituidos con R60; o Q2 es R160 o Q2 se selecciona entre el grupo constituido por O-alquil C1-4, S-alquil C1-4, alquil C1-4, alquenil C2-4 y alquinil C2-4, todos los cuales están sustituidos con R160; y R2 se selecciona entre: halogeno o R21, en el que R21 es arilo o Het, dicho R21 está opcionalmente sustituido con R150; R3 se selecciona entre alquilo C1-6, cicloalquilo C3-7, alquil C1-3-cicloalquilo C3-7, cicloalquenilo C5-7, alquil C1-3-cicloalquenilo C5-7, bicicloalquilo C6-10, alquil C1-3-bicicloalquilo C6-10, bicicloalquenilo C6-10, alquil C1-3-bicicloalquenilo C6-10, HCy o alquil C1-3-HCy, en el que HCy es un grupo heterocíclico saturado o insaturado de 4 a 7 eslabones con 1 a 3 heteroátomos seleccionados entre O, S y N; dichos alquilo, cicloalquilo, cicloalquenilo, bicicloalquilo, bicicloalquenilo, HCy y alquil-HCy estando opcionalmente sustituidos con 1 a 4 sustituyentes seleccionados entre: a) halogeno; b)alquilo C1-6 sustituido opcionalmente con: 1 a 3 sustituyentes seleccionados entre halogeno; OR31 o SR31 en el que R31 es H, alquilo C1-6, cicloalquilo C3-7 o alquil C1-3-cicloalquilo C3-7; o -N(R32)2 en el que cada R32 es independientemente H, alquilo C1-6, cicloalquilo C3-7 o alquil C1-3-cicloalquilo C3-7; o ambos R32 están covalentemente unidos juntos y al N al que están unidos para formar un heterociclo saturado de 5, 6 o 7 eslabones; c) OR33 o SR33 en el que R33 es H, alquilo C1-6, cicloalquilo C3-7 o alquil C1-3-cicloalquilo C3-7; d) N(R35)2 en el que cada R35 es independientemente H, alquilo C1-6, cicloalquilo C3-7 o alquil C1-3-cicloalquilo C3-7; o ambos R35 están covalentemente unidos juntos y al N al que están unidos para formar un heterociclo saturado de 5, 6 o 7 eslabones; R4a, R4b, R5 son cada uno de ellos independientemente H o definidos como R150; R60 se define cada uno de ellos como 1 a 4 sustituyentes independientemente seleccionados entre: 1 a 3 sustituyentes seleccionados entre halogeno; uno de cada sustituyente seleccionado entre: OPO3H, NO2, ciano, azido, C(=NH)NH2, C(=NH)NH alquilo C1-6 o C(=NH)NHCO alquilo C1-6, SO3H; y 1 a 3 sustituyentes seleccionados entre: a) alquilo C1-6, cicloalquilo C3-7, espirocicloalquilo C3-7 que opcionalmente contiene 1 o 2 heteroátomos seleccionados entre N, O y S; alquenilo C2-6, alquinilo C2-8, alquil C1-6-cicloalquilo C3-7, todos los cuales están opcionalmente sustituidos con R150; b) ORo; c) OC(O)Ro; d) SRo, SO2Rc, SO2N(RN2)RN1, SO2N(RN2)C(O)Rc, CONRN3SO2N(RN2)RN1, o CONRN2SO2Rc; e) N(RN2)RN1, N(RN2)COORc, N(RN2)SO2Rc o N(RN1)Ro; f) N(RN2)CORc; g) N(RN3)CON(RN2)RN1; h) N(RN3)COCORc; N(RN3)COCOORo o N(RN3)COCON(RN2)RN1; i) CORo; j) COORo, k) CON(RN2)RN1; l) arilo, Het, alquilo C1-4-arilo o alquilo C1-4-Het, estando todos los cuales sustituidos con R150, en los que opcionalmente dichos RN1, Rc y Ro están cada uno de ellos independientemente sustituidos con R150 como se ha definido; R150 se define cada uno de ellos como 1 a 4 sustituyentes seleccionados independientemente entre halogeno; 1 a 3 sustituyentes seleccionados de entre los halogenos; uno de cada sustituyentes seleccionados entre OPO3H, NO2, ciano, azido, C(=NH)NH2, C(=NH)NH alquilo C1-6 o C(=NH)NHCO alquilo C1-6; y 1 a 3 sustituyentes seleccionados entre: a) alquilo C1-6, cicloalquilo C3-7, espirocicloalquilo C3-7, que opcionalmente contiene 1 o 2 heteroátomos seleccionados entre N, O y S; alquenilo C2-6, alquinilo C2-8, alquil C1-3-cicloalquilo C3-7, todos los cuales sustituidos opcionalmente con R160; b) ORo; c) OC(O)Ro; d) SRo, SO2Rc, SO2N(RN2)RN1, SO2N(RN2)C(O)Rc, o CON(RN2)SO2Rc; e) N(RN2)RN1, N(RN2)COORc, N(RN2)SO2Rc o N(RN1)Ro; f) N(RN2)CORc; g) N(RN3)CON(RN2)RN1; h) N(RN3)COCORc; N(RN3)COCOORo, N(RN3)COCON(RN2)OH, N(RN3)COCON(RN2) o alquil C1-4 o N(RN3)COCON(RN2)RN1; i) CORo; j) COORo; k) tetrazol, triazol, CONRN3-SO2N(RN2)RN1; o CON(RN2)RN1; en el que dichos RN1, Rc y/o Ro están opcionalmente sustituidos con R160 como se ha definido; R160 se define cada uno de ellos como 1, 2 o 3 sustituyentes seleccionados independientemente entre: 1, 2 o 3 sustituyentes de F, y uno de cada sustituyente seleccionado entre tetrazol, triazol, Cl, Br, I, CN, nitro, alquilo C1-4, CF3, COOR161, SO3H, SR161, SCF3, SO2R163, OR161, OCF3, N(R162)2, SO2N(R162)2, NR162SO2Rc, NR162COR162; CON(R162)2, -NR161-CO-COOR161, -NR161-CO-CO-(NR162)2, -CONR161SO2Rc, CONR161-SO2N(R162)2 o -SO2-NR161-CORc, en el que R161, R163 y cada R162 es independientemente alquilo C1-4, cicloalquilo C3-7 o alquil C1-3-cicloalquilo C3-7; y R161 y cada R162 también pueden ser cada uno independientemente H; o ambos R162 están covalentemente unidos juntos y al N al que están unidos para formar un heterociclo saturado de 5, 6 o 7 eslabones; Ro, Rc se definen independientemente como alquilo C1-6, cicloalquilo C3-6, alquil C1-4-cicloalquilo C3-6, alquenilo C2-6, arilo Het, alquil C1-4-arilo y alquil C1-4-Het y Ro también puede ser H; RN1 se selecciona independientemente entre h, alquilo C1-6, cicloalquilo C3-7, alquil C1-4-cicloalquilo C3-6, alquenilo C2-6, arilo, Het, alquil C1-4-arilo, alquil C1-4-Het, o RN2, RN3, RN4 son inde
ARP040100155A 2003-01-22 2004-01-21 Derivados de indol inhibidores de las polimerasas virales AR047754A1 (es)

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JP2010077139A (ja) 2010-04-08
PL378194A1 (pl) 2006-03-06
RS20050556A (en) 2007-06-04
AU2004205429A1 (en) 2004-08-05
EA009323B1 (ru) 2007-12-28
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WO2004065367A8 (en) 2006-07-13
US7888363B2 (en) 2011-02-15
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NO20053892L (no) 2005-10-05
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TW200418843A (en) 2004-10-01
BRPI0406926A (pt) 2006-01-03
ECSP055913A (es) 2006-03-01
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EP1587787A1 (en) 2005-10-26
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HRP20050662A2 (en) 2006-07-31
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CA2511307C (en) 2011-09-27
US20040171626A1 (en) 2004-09-02
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EA200501065A1 (ru) 2006-02-24

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