AR087793A1 - Compuestos de benzofurano sustituido y metodos para el uso de los mismos en el tratamiento de enfermedades virales - Google Patents

Compuestos de benzofurano sustituido y metodos para el uso de los mismos en el tratamiento de enfermedades virales

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AR087793A1
AR087793A1 ARP120103286A ARP120103286A AR087793A1 AR 087793 A1 AR087793 A1 AR 087793A1 AR P120103286 A ARP120103286 A AR P120103286A AR P120103286 A ARP120103286 A AR P120103286A AR 087793 A1 AR087793 A1 AR 087793A1
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Argentina
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alkyl
membered monocyclic
group
haloalkyl
membered
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ARP120103286A
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Merck Sharp & Dohme
Istituto Di Recerche Di Biolog Molecolare P Angeletti S R L
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Publication of AR087793A1 publication Critical patent/AR087793A1/es

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
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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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4375—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A61K31/52—Purines, e.g. adenine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • 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
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
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    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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Abstract

Útiles como inhibidores de la NS5B polimerasa del virus de la hepatitis C (VHC), a la síntesis de tales compuestos, y al uso de tales compuestos para la inhibición de la actividad de la NS5B polimerasa del VHC, para el tratamiento o la prevención de infecciones por VHC y para la inhibición de la replicación viral del VHC y/o la producción viral en un sistema basado en células. Reivindicación 1: Un compuesto que tiene la fórmula (1) o una sal farmacéuticamente aceptable del mismo, en el que: A es un resto de formula (2) ó (3), en la que A puede estar unido al resto de benzofurano de fórmula (1) a través de cualquiera de los átomos de carbono en el anillo del grupo A; L es N o CH; M es N o CH; Q es -CH(R⁴ᵇ); U es -N(R⁵)-, O, S o -C(R⁴ᵇ)₂-; V es -N- o -C(R⁴ᵃ)-; W es -N- o -C(R⁴)-; o el grupo -W=V-U- es -NH-C(O)-N(R⁵)-; uno de Y¹ e Y² es -N- o -C(R¹⁰)-, y el otro de Y¹ e Y² es un átomo de carbono y representa el punto de unión del resto de benzofurano representado en la fórmula (1); X y Z son cada uno independientemente -N- o -C(R¹⁰)-; R¹ representa hasta 4 sustituyentes anulares opcionales, que pueden ser iguales o diferentes, y se seleccionan independientemente entre halo, alquilo C₁₋₆, haloalquilo C₁₋₆, fenilo, cicloalquilo monocíclico de 3 a 7 miembros, -O-(alquilo C₁₋₆), -O-(haloalquilo C₁₋₆) y -CN; R² es -C(O)N(R⁶)(R⁷); R³ es heterocicloalquilo de 5 ó 6 miembros o -N(R⁸)-S(O)ₙ-R⁹, en el que dicho heterocicloalquilo de 5 ó 6 miembros puede tener opcionalmente uno de sus átomos de carbono en el anillo reemplazados con un grupo carbonilo; R⁴ se selecciona entre H, halo, alquilo C₁₋₆, haloalquilo C₁₋₆, -O-(alquilo C₁₋₆), -O-(haloalquilo C₁₋₆), hidroxialquilo C₁₋₆, -C(O)O-(alquilo C₁₋₆), -(alquileno C₁₋₆)ʳ-arilo, -(alquileno C₁₋₆)ʳ-(cicloalquilo monocíclico de 3 a 7 miembros), -(alquileno C₁₋₆)ʳ-(heterocicloalquilo monocíclico de 4 a 7 miembros), -(alquileno C₁₋₆)ₙ-(heteroarilo monocíclico de 5 ó 6 miembros) y -(alquileno C₁₋₆)ʳ-(heteroarilo bicíclico de 9 ó 10 miembros), en el que dicho grupo arilo, dicho grupo cicloalquilo monocíclico de 3 a 7 miembros, dicho grupo heterocicloalquilo monocíclico de 4 a 7 miembros, dicho grupo heteroarilo monocíclico de 5 ó 6 miembros y dicho grupo heteroarilo bicíclico de 9 ó 10 miembros pueden estar opcionalmente sustituidos con hasta 3 grupos, que pueden ser iguales o diferentes, y se seleccionan entre halo, alquilo C₁₋₆, haloalquilo C₁₋₆, fenilo, cicloalquilo monocíclico de 3 a 7 miembros, -O-(alquilo C₁₋₆), -O-(haloalquilo C₁₋₆), -S(O)₂-(alquilo C₁₋₆), -C(O)O-(alquilo C₁₋₆), hidroxialquilo C₁₋₆ y -CN; R⁴ᵃ se selecciona entre H, alquilo C₁₋₆, cicloalquilo de 3 a 7 miembros, fenilo y heteroarilo monocíclico de 5 ó 6 miembros, en el que dicho grupo cicloalquilo de 3 a 7 miembros, dicho grupo fenilo y dicho grupo heteroarilo monocíclico de 5 ó 6 miembros pueden estar opcionalmente sustituidos con hasta 2 grupos, que pueden ser iguales o diferentes, y se seleccionan entre alquilo C₁₋₆, haloalquilo C₁₋₆, halo, -CN, -O-(alquilo C₁₋₆) y -O-(haloalquilo C₁₋₆); cada aparición de R⁴ᵇ se selecciona independientemente entre H, alquilo C₁₋₆, cicloalquilo de 3 a 7 miembros, fenilo y heteroarilo monocíclico de 5 ó 6 miembros, en el que dicho grupo cicloalquilo de 3 a 7 miembros, dicho grupo fenilo y dicho grupo heteroarilo monocíclico de 5 ó 6 miembros pueden estar opcionalmente sustituidos con hasta 2 grupos, que pueden ser iguales o diferentes, y se seleccionan entre alquilo C₁₋₆, haloalquilo C₁₋₆, halo, -CN, -O-(alquilo C₁₋₆) y -O-(haloalquilo C₁₋₆); cada aparición de R⁵ se selecciona independientemente entre H, alquilo C₁₋₆, hidroxialquilo C₁₋₆, -C(O)O-(alquilo C₁₋₆), -(alquileno C₁₋₆)ʳ-fenilo, -(alquileno C₁₋₆)ʳ-(cicloalquilo monocíclico de 3 a 7 miembros), -(alquileno C₁₋₆)ʳ-(heterocicloalquilo monocíclico de 4 a 7 miembros), -(alquileno C₁₋₆)ʳ-(heteroarilo monocíclico de 5 ó 6 miembros) y -(alquileno C₁₋₆)ʳ-(heteroarilo bicíclico de 9 ó 10 miembros), en el que dicho grupo fenilo, dicho grupo cicloalquilo monocíclico de 3 a 7 miembros, dicho grupo heterocicloalquilo monocíclico de 4 a 7 miembros, dicho grupo heteroarilo monocíclico de 5 ó 6 miembros y dicho grupo heteroarilo bicíclico de 9 ó 10 miembros puede estar opcionalmente sustituido con hasta 3 grupos, que pueden ser iguales o diferentes, y se seleccionan entre halo, alquilo C₁₋₆, haloalquilo C₁₋₆, fenilo, cicloalquilo monocíclico de 3 a 7 miembros, -O-(alquilo C₁₋₆), -O-(haloalquilo C₁₋₆), -S(O)₂-alquilo C₁₋₆, -C(O)O-(alquilo C₁₋₆), C₁₋₆ y -CN; R⁶ y R⁷ se seleccionan cada uno independientemente entre hidrógeno, alquilo C₁₋₆, fenilo, cicloalquilo monocíclico de 3 a 7 miembros, heterocicloalquilo monocíclico de 3 a 7 miembros y heteroarilo monocíclico de 5 ó 6 miembros; y R⁸ se selecciona entre H, alquilo C₁₋₆ y cicloalquilo monocíclico de 3 a 7 miembros; R⁹ se selecciona entre H, alquilo C₁₋₆, haloalquilo C₁₋₆, fenilo, cicloalquilo monocíclico de 3 a 7 miembros, heterocicloalquilo monocíclico de 3 a 7 miembros y heteroarilo monocíclico de 5 ó 6 miembros; cada aparición de R¹⁰ se selecciona independientemente entre H, halo, alquilo C₁₋₆, haloalquilo C₁₋₆, -O-(alquilo C₁₋₆), -O-(haloalquilo C₁₋₆) y -CN; cada aparición de n es independientemente 1 ó 2; y cada aparición de r es independientemente 0 ó 1.
ARP120103286A 2011-09-08 2012-09-06 Compuestos de benzofurano sustituido y metodos para el uso de los mismos en el tratamiento de enfermedades virales AR087793A1 (es)

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WO2013033901A1 (en) 2011-09-08 2013-03-14 Merck Sharp & Dohme Corp. Heterocyclic-substituted benzofuran derivatives and methods of use thereof for the treatment of viral diseases
WO2013033900A1 (en) 2011-09-08 2013-03-14 Merck Sharp & Dohme Corp. Tetracyclic heterocycle compounds and methods of use thereof for the treatment of viral diseases
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WO2014121416A1 (en) 2013-02-07 2014-08-14 Merck Sharp & Dohme Corp. Tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis c
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CN112912073B (zh) 2018-07-10 2023-11-28 环境光子学公司 用于基于铜氧化还原的染料敏化太阳能电池的太阳能电池染料及其组合
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