AR092959A1 - Derivados de nucleosidos 2-metil sustituidos y metodos de uso de los mismos para el tratamiento de enfermedades virales - Google Patents

Derivados de nucleosidos 2-metil sustituidos y metodos de uso de los mismos para el tratamiento de enfermedades virales

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AR092959A1
AR092959A1 ARP130103665A ARP130103665A AR092959A1 AR 092959 A1 AR092959 A1 AR 092959A1 AR P130103665 A ARP130103665 A AR P130103665A AR P130103665 A ARP130103665 A AR P130103665A AR 092959 A1 AR092959 A1 AR 092959A1
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alkyl
alkylene
cycloalkyl
aryl
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Merck Sharp & Dohme
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
    • 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
    • A61P31/14—Antivirals for RNA viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/067—Pyrimidine radicals with ribosyl as the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
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  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Reivindicación 1: Un compuesto que tiene la fórmula (1), o una sal farmacéuticamente aceptable del mismo, en la que: B es un compuesto de fórmula (2) ó (3); X es O, N, S o CH₂; R¹ es H, o un compuesto de fórmula (4), (5), (6) ó (7); R² es H, -C(O)-(alquilo C₁₋₂₀), -C(O)-(cicloalquilo C₃₋₆), -C(O)O-(alquilo C₁₋₂₀), -C(O)O-(cicloalquilo C₃₋₆), -C(O)NH-(alquilo C₁₋₂₀), -C(O)NH-(cicloalquilo C₃₋₆) o el resto de fórmula (7), o R¹ y R² se unen para formar un grupo que tiene la fórmula (8); R³ es -CN, -N₃ o -CºCH; R⁴ es H, alquilo C₁₋₆, cicloalquilo C₃₋₇, fenilo o bencilo, en el que dicho alquilo C₁₋₆ puede estar opcionalmente sustituido con un grupo seleccionado entre halo, -OR¹², -SR¹², guanidino, -N(R¹²)₂, -C(O)OR¹², -C(O)N(R¹²)₂, -NHC(O)R¹², heteroarilo monocíclico de 5 ó 6 miembros y heteroarilo bicíclico de 9 ó 10 miembros, y en el que dicho grupo fenilo y dicho grupo bencilo pueden estar opcionalmente sustituidos con hasta 2 grupos, cada uno seleccionado independientemente entre alquilo C₁₋₆, halo y -OR¹²; R⁵ es H, alquilo C₁₋₆, cicloalquilo C₃₋₇, fenilo o bencilo, en el que dicho alquilo C₁₋₆ puede estar opcionalmente sustituido con un grupo seleccionado entre halo, -OR¹², -SR¹², guanidino, -N(R¹²)₂, -C(O)OR¹², -C(O)N(R¹²)₂, -NHC(O)R¹², heteroarilo monocíclico de 5 ó 6 miembros y heteroarilo bicíclico de 9 ó 10 miembros, y en el que dicho grupo fenilo y dicho grupo bencilo pueden estar opcionalmente sustituidos con hasta 2 grupos, cada uno seleccionado independientemente entre alquilo C₁₋₆, halo y -OR¹²; R⁶ es H, alquilo C₁₋₂₀, alquenilo C₂₋₂₀, -(alquileno C₁₋₃)ₘ-(cicloalquilo C₃₋₇), -(alquileno C₁₋₃)ₘ-(arilo C₆₋₁₀) o -(alquileno C₁₋₃)ₘ-adamantilo, en el que dicho grupo alquilo C₁₋₂₀, dicho grupo alquenilo C₂₋₂₀, dicho grupo arilo C₆₋₁₀ y dicho grupo adamantilo pueden estar opcionalmente sustituidos hasta con tres grupos, cada uno seleccionado independientemente entre halo, -OR¹², -C(O)OR¹², CN, NO₂, haloalquilo C₁₋₆, hidroxialquilo C₁₋₆, cicloalquilo C₃₋₇, arilo C₆₋₁₀, heteroarilo monocíclico de 5 ó 6 miembros, heteroarilo bicíclico de 9 ó 10 miembros, -N(R¹²)₂, -C(O)N(R¹²)₂ -SR¹², -S(O)R¹², -S(O)₂R¹², -S(O)₂N(R¹²)₂, -NHC(O)R¹², -NHC(O)OR¹² y -NC(O)N(R¹²)₂; R⁷ es H, arilo C₆₋₁₀, heteroarilo monocíclico de 5 ó 6 miembros, heteroarilo bicíclico de 9 ó 10 miembros, o -(alquileno C₁₋₃)-C(O)O-(alquilo C₁₋₆), en el que dicho grupo arilo C₆₋₁₀, dicho grupo heteroarilo monocíclico de 5 ó 6 miembros y dicho grupo heteroarilo bicíclico de 9 ó 10 miembros pueden estar opcionalmente sustituidos con R¹³; R⁸ es H o -C(O)-(alquilo C₁₋₂₀); R¹¹ es H, alquilo C₁₋₂₀, alquenilo C₂₋₂₀, -(alquileno C₁₋₃)ₘ-(cicloalquilo C₃₋₇), cicloalquilo C₃₋₇, -(alquileno C₁₋₃)ₘ-arilo C₆₋₁₀ o -(alquileno C₁₋₃)ₘ-adamantilo, heteroarilo monocíclico de 5 ó 6 miembros, heteroarilo bicíclico de 9 ó 10 miembros, en el que dicho grupo alquilo C₁₋₂₀, dicho grupo alquenilo C₂₋₂₀, dicho grupo arilo C₆₋₁₀, dicho grupo adamantilo, 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 cinco grupos, cada uno seleccionado independientemente entre alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇, arilo C₆₋₁₀, heteroarilo monocíclico de 5 ó 6 miembros, heteroarilo bicíclico de 9 ó 10 miembros, halo, -OR¹², -SR¹², -S(O)R¹², -S(O)₂R¹², -S(O)₂N(R¹²)₂, haloalquilo C₁₋₆, hidroxialquilo C₁₋₆, -O-(haloalquilo C₁₋₆), -CN, -NO₂, -N(R¹²)₂, -C(O)OR¹², -C(O)N(R¹²)₂ y -NHC(O)R¹², -NHC(O)OR¹² y -NHC(O)N(R¹²)₂; cada aparición de R¹² es independientemente H, alquilo C₁₋₁₀, haloalquilo C₁₋₆, hidroxialquilo C₁₋₆, -(alquileno C₁₋₃)ₘ-(cicloalquilo C₃₋₇), -(alquileno C₁₋₃)ₘ-(arilo C₆₋₁₀), -(alquileno C₁₋₃)ₘ-(heterocicloalquilo de 4 a 7 miembros), -(alquileno C₁₋₃)ₘ-(heteroarilo monocíclico de 5 ó 6 miembros) o -(alquileno C₁₋₃)ₘ-(heteroarilo bicíclico de 9 ó 10 miembros), en el que dicho grupo cicloalquilo C₃₋₇, dicho grupo arilo C₆₋₁₀, dicho grupo heterocicloalquilo de 4 a 7 miembros, dicho grupo heteroarilo monocíclico de 5 ó 6 miembros o dicho grupo heteroarilo bicíclico de 9 ó 10 miembros puede estar opcionalmente sustituido con R¹⁶; R¹³ representa de uno a cinco grupos sustituyentes, cada uno seleccionado independientemente entre alquilo C₁₋₆, halo, -OR¹², -SR¹², haloalquilo C₁₋₆, hidroxialquilo C₁₋₆, -O-(haloalquilo C₁₋₆), -CN, -NO₂, -N(R¹²)₂, -C(O)OR¹², -C(O)N(R¹²)₂ y -NHC(O)R¹², o dos grupos R¹³ cualesquiera en átomos de carbono adyacentes en el anillo se pueden combinar para formar -O-R¹⁴-O-; R¹⁴ es -[C(R¹⁵)₂]ₙ-; cada aparición de R¹⁵ es independientemente H o alquilo C₁₋₆; R¹⁶ representa de uno a cinco grupos sustituyentes, cada uno seleccionado independientemente entre alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, halo, -OR¹⁷, -SR¹⁷, haloalquilo C₁₋₆, hidroxialquilo C₁₋₆, -O-(haloalquilo C₁₋₆), -CN, -NO₂, -N(R¹⁷)₂, -C(O)OR¹⁷, -C(O)N(R¹⁷)₂ y -NHC(O)R¹⁷; cada aparición de R¹⁷ es independientemente H, alquilo C₁₋₆, haloalquilo C₁₋₆, hidroxialquilo C₁₋₆, -(alquileno C₁₋₃)ₘ-(cicloalquilo C₃₋₇), -(alquileno C₁₋₃)ₘ-(arilo C₆₋₁₀), -(alquileno C₁₋₃)ₘ-(heterocicloalquilo de 4 a 7 miembros), -(alquileno C₁₋₃)ₘ-(heteroarilo monocíclico de 5 ó 6 miembros) o -(alquileno C₁₋₃)ₘ-(heteroarilo bicíclico de 9 ó 10 miembros); cada aparición de m es independientemente 0 ó 1, y cada aparición de n es independientemente 1, 2 ó 3.
ARP130103665A 2012-10-17 2013-10-09 Derivados de nucleosidos 2-metil sustituidos y metodos de uso de los mismos para el tratamiento de enfermedades virales AR092959A1 (es)

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