AR090411A1 - Compuestos terapeuticamente activos y sus metodos de uso - Google Patents

Compuestos terapeuticamente activos y sus metodos de uso

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Publication number
AR090411A1
AR090411A1 ARP130100062A ARP130100062A AR090411A1 AR 090411 A1 AR090411 A1 AR 090411A1 AR P130100062 A ARP130100062 A AR P130100062A AR P130100062 A ARP130100062 A AR P130100062A AR 090411 A1 AR090411 A1 AR 090411A1
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Argentina
Prior art keywords
alkylene
phenyl
ring
alkyl
optionally substituted
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ARP130100062A
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English (en)
Inventor
Dlbarre Byron
Travins Jeremy
Zhang Li
Yan Shunqi
Guo Tao
Cianchetta Giovanni
O Saunders Jeffrey
Popovici-Muller Janeta
G Salituro Francesco
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Agios Pharmaceuticals Inc
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Application filed by Agios Pharmaceuticals Inc filed Critical Agios Pharmaceuticals Inc
Publication of AR090411A1 publication Critical patent/AR090411A1/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
    • C07D401/14—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
    • 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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    • 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
    • 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
    • A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • 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
    • 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
    • C07D401/04—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
    • 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
    • C07D401/12—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—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
    • 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
    • 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
    • C07D405/12—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 chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
    • 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
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/02—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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Se proporcionan compuestos útiles para tratar cáncer y métodos para tratar cáncer que comprende administrarle a un sujeto que lo necesita un compuesto que se describe en la presente. Reivindicación 1: Un compuesto que tiene la fórmula (1) o una sal o hidrato farmacéuticamente aceptable de este, donde: el anillo A es un arilo monocíclico o heteroarilo monocíclico de 5 - 6 miembros opcionalmente sustituido; el anillo B es un arilo monocíclico o heteroarilo monocíclico de 5 - 6 miembros opcionalmente sustituido; R¹ y R³ se seleccionan cada uno independientemente de hidrógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, -O-alquilo C₁₋₄ y CN, donde una porción alquilo de R¹ está opcionalmente sustituida por -OH, NH₂, NH(alquilo C₁₋₄) o N(alquilo C₁₋₄)₂; R² se selecciona de: -(alquilo C₁₋₆), -(alquenilo o alquinilo C₂₋₆), -(alquileno C₁₋₆)-N(R⁶)-(alquileno C₁₋₆)-O-(alquilo C₁₋₆), -(alquileno C₁₋₆)-N(R⁶)-(alquileno C₀₋₆)-Q, -(alquileno C₁₋₆)-N(R⁶)(R⁶), -(alquileno C₁₋₆)-N(R⁶)-S(O)₁₋₂-(alquilo C₁₋₆), -(alquileno C₁₋₆)-N(R⁶)-S(O)₁₋₂-(alquilo C₀₋₆)-Q, -(alquileno C₁₋₆)-S(O)₁₋₂-N(R⁶)(R⁶), -(alquileno C₁₋₄)-S(O)₁₋₂-N(R⁶)-(alquileno C₁₋₆)-Q, -C(O)N(R⁶)-(alquileno C₁₋₆)-C(O)-(alquileno C₀₋₆)-O-(alquilo C₁₋₆), -C(O)N(R⁶)-(alquileno C₁₋₆)-C(O)-(alquileno C₀₋₆)-O-(alquileno C₀₋₆)-Q, -(alquileno C₁₋₆)-O-C(O)-(alquilo C₁₋₆), -(alquileno C₁₋₆)-O-C(O)-(alquilo C₀₋₆)-Q, -(alquileno C₁₋₆)-O-(alquilo C₁₋₆), -(alquileno C₁₋₆)-O-(alquileno C₁₋₆)-Q, -(alquileno C₀₋₆)-C(O)-(alquileno C₀₋₆)-O-(alquilo C₁₋₆), -(alquileno C₀₋₆)-C(O)-(alquileno C₀₋₆)-O-(alquileno C₁₋₆)-Q, -(alquileno C₁₋₆)-O-C(O)-(alquilo C₁₋₆), -(alquileno C₁₋₆)-O-C(O)-(alquileno C₀₋₆)-Q, -(alquileno C₀₋₆)-C(O)N(R⁶)-(alquilo C₁₋₆), -(alquileno C₀₋₆)-C(O)N(R⁶)-(alquileno C₀₋₆)-Q, -(alquileno C₁₋₆)-N(R⁶)C(O)-(alquilo C₁₋₆), -(alquileno C₁₋₆)-N(R⁶)C(O)-(alquileno C₀₋₆)-Q, -(alquileno C₀₋₆)-S(O)₀₋₂-(alquilo C₁₋₆), -(alquileno C₀₋₆)-S(O)₀₋₂-(alquileno C₀₋₆)-Q, -(alquileno C₁₋₆)-N(R⁶)-C(O)-N(R⁶)-(alquilo C₁₋₆), -(alquileno C₀₋₆)-Q, -(alquileno C₀₋₆)-C(O)-(alquilo C₁₋₆), -(alquileno C₀₋₆)-C(O)-(alquileno C₀₋₆)-Q, donde: cualquier resto alquilo o alquileno presente en R² está opcionalmente sustituido por uno o más -OH, -O(alquilo C₁₋₄) o halo; cualquier resto metilo terminal presente en R² está opcionalmente remplazado por -CH₂OH, CF₃, -CH₂F, -CH₂Cl, C(O)CH₃, C(O)CF₃, CN o CO₂H; cada R⁶ se selecciona independientemente de hidrógeno y alquilo C₁₋₆ y Q se selecciona de arilo, heteroarilo, carbociclilo y heterociclilo, cualquiera de los cuales está opcionalmente sustituido o R¹ y R³ se toman opcionalmente juntos con el átomo de carbono al que están unidos C(=O) o R¹ y R² se toman opcionalmente juntos para formar carbociclilo sustituido, heterociclilo opcionalmente sustituido o heteroarilo opcionalmente sustituido, donde: a) cuando el anillo A es fenilo no sustituido y el anillo B es fenilo sustituido por metoxi o etoxi; entonces dicho fenilo del anillo B no está sustituido adicionalmente por oxazolilo; b) cuando el anillo A es fenilo opcionalmente sustituido o piridilo opcionalmente sustituido y el anillo B es fenilo opcionalmente sustituido; entonces la porción del compuesto representada por -NH-C(R¹)(R²)(R³) no es -NH(CH₂)-arilo; c) cuando el anillo A es fenilo opcionalmente sustituido y el anillo B es fenilo o pirrolilo opcionalmente sustituido, entonces la porción del compuesto representada por -NH-C(R¹)(R²)(R³) no es -NH(CH₂)C(O)NH₂; d) cuando el anillo A es fenilo sustituido por 2 o más hidroxilo o metoxi y el anillo B es fenilo opcionalmente sustituido; entonces la porción del compuesto representada por -NH-C(R¹)(R²)(R³) no es -NH-cicloheptilo; e) cuando el anillo A es fenilo opcionalmente sustituido y el anillo B es fenilo opcionalmente sustituido; entonces R¹ y R³ no forman 2,2,6,6,-tetrametilpiperidin-4-ilo; f) cuando el anillo A y el anillo B son fenilo opcionalmente sustituido; entonces la porción del compuesto representada por -NH-C(R¹)(R²)(R³) no es cisteína, fenilalanina o leucina opcionalmente sustituida o un éster metílico de estas; g) cuando el anillo A es fenilo o piridin-3-ilo opcionalmente sustituido por uno o más sustituyentes que se seleccionan de halo, metilo o CF₃ y el anillo B es fenilo opcionalmente sustituido por uno o más sustituyentes que se seleccionan de halo, metilo, CF₃, metoxi o CH=C(fenilo)CN; entonces la porción del compuesto representada por –NH-C(R¹)(R²)(R³) es diferente de -NH(alquileno C₁₋₈)-N(Rᵃ)(Rᵃ), -NH-1-(aminometil)ciclopentilmetilo, -NH-4-(aminometil)ciclohexilmetilo, donde cada Rᵃ es hidrógeno, alquilo C₁₋₄ o dos Rᵃ se toman junto con el nitrógeno al que están unidos en común para formar un morfolin-4-ilo o piperidin-1-ilo; h) cuando el anillo A es fenilo, 4-clorofenilo o 4-metilfenilo y el anillo B es 4-clorofenilo o 3,4-diclorofenilo; entonces la porción del compuesto representada por -NH-C(R¹)(R²)(R³) no es -NH-isopropilo; i) cuando el anillo A es fenilo no sustituido y la porción del compuesto representada por –NH-C(R¹)(R²)(R³) es -NH-CH₂CH₂N(CH₃)₂, -NH-CH₂CH₂-morfolin-4-ilo o -NH-CH₂CH₂OH; entonces el anillo B es diferente de oxadiazol, imidazol, tiazol u oxazol cada uno de los cuales está sustituido por -C(O)NHRᵇ, donde Rᵇ es isopropilo, ciclopropilo o 2-cloro-6-metilfenilo; j) cuando el anillo A es fenilo sustituido por SO₂OH o SO₂Na, y el anillo B es fenilo, o cuando el anillo A es fenilo sustituido por SO₂OH y el anillo B es fenilo; entonces la porción del compuesto representada por -NH-C(R¹)(R²)(R³) no es -NH(CH₂)₂OH o -NH(CH₂)CH(OH)CH₃; y k) el compuesto es diferente de: (E)-3-(4-((4-((3-(dietilamino)propil)amino)-6-fenil-1,3,5-triazin-2-il)amino)-2-metoxifenil)-2-fenilacrilonitrilo, 4-((4-((furan-2-ilmetil)amino)-6-(piridin-4-il)-1,3,5-triazin-2-il)amino)fenol, 3-(4-((5-aminopentil)amino)-6-((3-fluorofenil)amino)-1,3,5-triazin-2-il)fenol, N²,6-bis(3-fluorofenil)-N⁴-(piperidin-3-il)-1,3,5-triazin-2,4-diamina, N²-butil-6-fenil-N⁴-(p-tolil)-1,3,5-triazin-2,4-diamina, N²-ciclohexil-N⁴,6-difenil-1,3,5-triazin-2,4-diamina, (R)-3-((4-(3-clorofenil)-6-(pirrolidin-3-ilamino)-1,3,5-triazin-2-il)amino)-4-metilbenzamida, 2-cloro-4-(metilsulfonil)-N-[4-(fenilamino)-6-(2-piridinil)-1,3,5-triazin-2-il]-benzamida, N²-(2-metoxietil)-N⁴-fenil-6-[5-[6-(2,2,2-trifluoroetoxi)-3-piridinil]-1,2,4-oxadiazol-3-il]-1,3,5-triazin-2,4-diamina, N²-(2-furanilmetil)-6-fenil-N⁴-[3-(trifluorometil)fenil]-1,3,5-triazin-2,4-diamina, 6-(3-metoxifenil)-N²-metil-N⁴-(3-nitrofenil)-1,3,5-triazin-2,4-diamina, N²-butil-N⁴-(4-metilfenil)-6-fenil-1,3,5-triazin-2,4-diamina y@@@4-[[4-(5-cloro-2-metilfenil)-6-(metilamino)]-1,3,5-triazin-2-il]amino-bencenometanol.
ARP130100062A 2012-01-06 2013-01-07 Compuestos terapeuticamente activos y sus metodos de uso AR090411A1 (es)

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