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AR094797A1 - PIRROLOTRIAZINE DERIVATIVES AS PI3K INHIBITORS - Google Patents

PIRROLOTRIAZINE DERIVATIVES AS PI3K INHIBITORS

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Publication number
AR094797A1
AR094797A1 ARP140100477A ARP140100477A AR094797A1 AR 094797 A1 AR094797 A1 AR 094797A1 AR P140100477 A ARP140100477 A AR P140100477A AR P140100477 A ARP140100477 A AR P140100477A AR 094797 A1 AR094797 A1 AR 094797A1
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Argentina
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group
linear
branched
alkyl
phenyl
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ARP140100477A
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Spanish (es)
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Erra Sola Montserrat
Taltavull Moll Joan
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Almirall Sa
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    • C—CHEMISTRY; METALLURGY
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
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  • General Chemical & Material Sciences (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Reivindicación 1: Un compuesto de fórmula (1), o una sal farmacéuticamente aceptable, o N-óxido, o derivado isotópicamente marcado del mismo, en donde, W representa un enlace directo o un enlazador seleccionado de un grupo -O-(CH₂)₀₋₃-, un grupo -S-(CH₂)₀₋₃-, un grupo -(CH₂)₁₋₄-, un grupo -(CH₂)₀₋₃-NRᵃ-(CH₂)₀₋₃-, un grupo -(CH₂)₀₋₃-NRᵃ-C(O)-(CH₂)₀₋₃-, un grupo -O-(CH₂)₂₋₄-N(*)Rᵃ, un grupo -(CH₂)₀₋₃,-N(*)-(CH₂)₂₋₄-N(Rᵃ)Rᵇ, un grupo -(CH₂)₀₋₃-NRᵃ-CH[C(*)H₂]-(CH₂)₀₋₃-C(O)-N(Rᵃ)Rᵇ, un grupo -(CH₂)₀₋₃-N[C(*)H₂]-(CH₂)₂₋₄N(Rᵃ)Rᵇ, un grupo -(CH₂)₀₋₃-N(*)-(CH₂)₀₋₃-Rᶜ o un grupo -(CH₂)₀₋₃-N[C(*)H₂]-(CH₂)₀₋₃-Rᶜ; en donde cada uno de Rᵃ y Rᵇ independientemente representa hidrógeno, un grupo alquilo lineal o ramificado C₁₋₄ o un grupo -(CH₂)₀₋₃-O-(alquilo lineal o ramificado C₁₋₄); y en donde (*) representa el punto de unión a R¹; Rᶜ representa un grupo cicloalquilo C₃₋₁₀, un grupo fenilo, un grupo heteroarilo de 5 a 7 miembros que contiene al menos un heteroátomo seleccionado de O, S y N, un grupo heterocíclico de 5 a 7 miembros, monocíclico o bicíclico, que contiene al menos un heteroátomo seleccionado de O, S y N; en donde los grupos cicloalquilo, fenilo, heteroarilo y heterocíclico están no sustituidos o sustituidos con uno o más sustituyentes seleccionados de un átomo de halógeno, un grupo hidroxilo, un grupo ciano, un grupo -NH₂, un grupo -CHF₂, un grupo -CF₃, o un grupo alquilo lineal o ramificado C₁₋₄; X representa un átomo de nitrógeno o un grupo -CR⁶; R¹ representa un grupo alquilo lineal o ramificado C₁₋₆, un grupo hidroxialquilo lineal o ramificado C₁₋₆, un grupo -(CH₂)₀₋₃N(Rᵈ)Rᵉ, un grupo haloalquilo lineal o ramificado C₁₋₆, un grupo cicloalquilo C₃₋₁₀, un grupo cicloalquenilo C₃₋₁₀, un grupo fenilo, un grupo heteroarilo de 5 a 14 miembros que contiene al menos un heteroátomo seleccionado de O, S y N, o un grupo heterocíclico de 5 a 14 miembros, monocíclico o bicíclico, que contiene al menos un heteroátomo seleccionado de O, S y N; en donde cada uno de Rᵈ y Rᵉ representa independientemente un átomo de hidrógeno o un grupo alquilo lineal o ramificado C₁₋₄; y en donde los grupos cicloalquilo, cicloalquenilo, fenilo, heteroarilo y heterocíclico están no sustituidos o sustituidos con uno o más sustituyentes seleccionados de un átomo de halógeno, un grupo hidroxilo, un grupo ciano, un grupo alquilo lineal o ramificado C₁₋₄, un grupo haloalquilo C₁₋₄, un grupo hidroxialquilo lineal o ramificado C₁₋₄, un grupo cicloalquilo C₃₋₄, un grupo -(CH₂)₁₋₃CN, un grupo -(CH₂)₀₋₃-O-(CH₂)₀₋₃-O-R⁷, un grupo -(CH₂)₀₋₃-O-(alquilo lineal o ramificado C₁₋₄), un grupo -(CH₂)₀₋₃-O-(CH₂)₂₋₄-NR⁷R⁸, un grupo -(CH₂)₀₋₃NR⁷R⁸, un grupo -(CH₂)₀₋₃-NH-(CH₂)₂₋₄NR⁷R⁸, un grupo -C(O)-(CH₂)₁₋₃CN, un grupo -C(O)-O-(alquilo lineal o ramificado C₁₋₄), un grupo -C(O)-OH, un grupo -C(O), un grupo -C(O)-(CH₂)₀₋₃-(alquilo lineal o ramificado C₁₋₄), un grupo -C(O)-(CH₂)₀₋₃-(fenilo), un grupo -C(O)-O-(CH₂)₀₋₃-(fenilo), un grupo -C(O)-(CH₂)₀₋₃-(heterocíclico de 5 a 9 miembros, monocíclico o bicíclico, que contiene al menos un heteroátomo seleccionado de O, S y N), un grupo -C(O)-(CH₂)₀₋₃-(heteroarilo de 5 a 7 miembros que contiene al menos un heteroátomo seleccionado de O, S y N), un grupo -C(O)-(CH₂)₀₋₃-NR⁷[CH(alquil C₁₋₂)]₀₋₃-(fenilo), un grupo -C(O)-(CH₂)₀₋₃-NR¹(CH₂)₀₋₃-(fenilo), un grupo -C(O)-(CH₂)₀₋₃-NR⁷(CH₂)₀₋₃-(heteroarilo de 5 a 7 miembros que contiene al menos un heteroátomo seleccionado de O, S y N), un grupo -C(O)-(CH₂)₀₋₃-NR⁷(CH₂)₀₋₃-(heterocíclico de 5 a 9 miembros, monocíclico o bicíclico, que contiene al menos un heteroátomo seleccionado de O, S y N), un grupo -C(O)-(CH₂)₀₋₃-NR⁷R⁸, un grupo -C(O)-(CH₂)₀₋₃-NR⁷-(CH₂)₂₋₆-NR⁷R⁸, un grupo -C(O)-(CH₂)₀₋₃-NR⁷-(CH₂)₁₋₆-NR⁷-(CH₂)₁₋₆-NR⁷R⁸, un grupo -NR⁷-S(O)₂(CH₂)₀₋₃R⁸, un grupo -S(O)₂(CH₂)₀₋₃-R⁸, un grupo -S(O)₂(CH₂)₀₋₃NR⁷R⁸, un grupo -S(O)₂(CH₂)₀₋₃-NR⁷(CH₂)₀₋₃-(fenilo), un grupo -(CH₂)₀₋₃-(heteroarilo de 5 a 7 miembros que contiene al menos un heteroátomo seleccionado de O, S y N), un grupo -(CH₂)₀₋₃-(heterocíclico de 5 a 7 miembros, monocíclico o bicíclico, que contiene al menos un heteroátomo seleccionado de O, S y N), un grupo -(CH₂)₀₋₃-(fenilo) o un grupo -(CH₂)₀₋₃-O-(CH₂)₀₋₃-(fenilo); en donde cada grupo fenilo, heteroarilo y heterocíclico está no sustituido o sustituido con uno o más sustituyentes seleccionados de un grupo hidroxilo, un grupo alquilo lineal o ramificado C₁₋₄, un grupo hidroxialquilo lineal o ramificado C₁₋₄, un grupo -(CH₂)₀₋₃-O-(alquilo lineal o ramificado C₁₋₄), un grupo -C(O)-O-(alquilo lineal o ramificado C₁₋₄), un grupo -C(O)-OH, un grupo -C(O)-(CH₂)₀₋₃-(alquilo lineal o ramificado C₁₋₄), un grupo -C(O)-(CH₂)₀₋₃-NRᶠRᵍ, un grupo -(CH₂)₀₋₃N(Rᶠ)Rᵍ, un grupo -S(O)₂(CH₂)₀₋₃(alquilo lineal o ramificado C₁₋₄), un grupo -S(O)₂(CH₂)₀₋₃NRᶠRᵍ, un grupo -NRᶠ-S(O)₂(CH₂)₀₋₃NRᶠRᵍ, un grupo -NRᶠ-S(O)₂(CH₂)₀₋₃Rᵍ, un grupo -(CH₂)₀₋₃-O-(CH₂)₂₋₄-NRᶠRᵍ o un grupo -(CH₂)₀₋₃-(heteroarilo de 5 a 7 miembros que contiene al menos un heteroátomo seleccionado de O, S y N); en donde el grupo heteroarilo está no sustituido o sustituido con uno o más sustituyentes seleccionados de un grupo alquilo lineal o ramificado C₁₋₃ o un grupo -(CH₂)₀₋₃NRᶠRᵍ; y en donde Rᶠ y Rᵍ independientemente representa hidrógeno, un grupo alquilo lineal o ramificado C₁₋₄ o un grupo hidroxialquilo lineal o ramificado C₁₋₄; cada uno de R² y R³ representa independientemente un átomo de hidrógeno, un átomo de halógeno, un grupo hidroxilo, un grupo ciano, un grupo alquilo C₁₋₄ lineal o ramificado, un grupo haloalquilo C₁₋₄, un grupo hidroxialquilo lineal o ramificado C₁₋₄, un grupo cicloalquilo C₁₋₄, un grupo alcoxi C₁₋₄, un grupo -NH₂, un grupo -N(CH₃)H, o un grupo -N(CH₃)₂; R⁴ representa un átomo de hidrógeno, un grupo alquilo lineal o ramificado C₁₋₄, un grupo haloalquilo C₁₋₄, un grupo hidroxialquilo lineal o ramificado C₁₋₄, un grupo cicloalquilo C₃₋₇, un grupo -(CH₂)₀₋₃-S-(CH₂)₀₋₃-(fenilo), un grupo -(CH₂)₀₋₃-S-(CH₂)₀₋₃-(heteroarilo de 5 a 7 miembros que contiene al menos un heteroátomo seleccionado de O, S y N), un grupo -(CH₂)₀₋₃-O-(CH₂)₀₋₃-(fenilo), un grupo -(CH₂)₀₋₃-O-(CH₂)₀₋₃-(heteroarilo de 5 a 7 miembros que contiene al menos un heteroátomo seleccionado de O, S y N), un grupo -(CH₂)₀₋₃-(fenilo), un grupo -(CH₂)₀₋₃-(heteroarilo de 5 a 7 miembros que contiene al menos un heteroátomo seleccionado de O, S y N), en donde los grupos fenilo y heterociclilo están no sustituidos o sustituClaim 1: A compound of formula (1), or a pharmaceutically acceptable salt, or N-oxide, or isotopically labeled derivative thereof, wherein, W represents a direct bond or a linker selected from a group -O- (CH₂) ₀₋₃-, a group -S- (CH₂) ₀₋₃-, a group - (CH₂) ₁₋₄-, a group - (CH₂) ₀₋₃-NRᵃ- (CH₂) ₀₋₃-, a group - (CH₂) ₀₋₃-NRᵃ-C (O) - (CH₂) ₀₋₃-, a group -O- (CH₂) ₂₋₄-N (*) Rᵃ, a group - (CH₂) ₀₋ ₃, -N (*) - (CH₂) ₂₋₄-N (Rᵃ) Rᵇ, a group - (CH₂) ₀₋₃-NRᵃ-CH [C (*) H₂] - (CH₂) ₀₋₃-C (O) -N (Rᵃ) Rᵇ, a group - (CH₂) ₀₋₃-N [C (*) H₂] - (CH₂) ₂₋₄N (Rᵃ) Rᵇ, a group - (CH₂) ₀₋₃- N (*) - (CH₂) ₀₋₃-Rᶜ or a group - (CH₂) ₀₋₃-N [C (*) H₂] - (CH₂) ₀₋₃-Rᶜ; wherein each of Rᵃ and Rᵇ independently represents hydrogen, a linear or branched C₁₋₄ alkyl group or a group - (CH₂) ₀₋₃-O- (linear or branched C₁₋₄ alkyl); and where (*) represents the point of attachment to R¹; Rᶜ represents a C₃₋₁₀ cycloalkyl group, a phenyl group, a 5-7 membered heteroaryl group containing at least one heteroatom selected from O, S and N, a 5-7 membered heterocyclic group, monocyclic or bicyclic, containing at least one heteroatom selected from O, S and N; wherein the cycloalkyl, phenyl, heteroaryl and heterocyclic groups are unsubstituted or substituted with one or more substituents selected from a halogen atom, a hydroxyl group, a cyano group, a -NH₂ group, a -CHF₂ group, a -CF₃ group , or a linear or branched C₁₋₄ alkyl group; X represents a nitrogen atom or a -CR⁶ group; R¹ represents a linear or branched alkyl group C₁₋₆, a linear or branched hydroxyalkyl group C₁₋₆, a group - (CH₂) ₀₋₃N (Rᵈ) Rᵉ, a linear or branched haloalkyl group C₁₋₆, a C₃ cycloalkyl group ₋₁₀, a C₃₋₁₀ cycloalkenyl group, a phenyl group, a 5-14 membered heteroaryl group containing at least one heteroatom selected from O, S and N, or a 5 to 14 membered heterocyclic group, monocyclic or bicyclic, containing at least one heteroatom selected from O, S and N; wherein each of Rᵈ and Rᵉ independently represents a hydrogen atom or a linear or branched C₁₋₄ alkyl group; and wherein the cycloalkyl, cycloalkenyl, phenyl, heteroaryl and heterocyclic groups are unsubstituted or substituted with one or more substituents selected from a halogen atom, a hydroxyl group, a cyano group, a linear or branched C₁₋₄ alkyl group, a C₁₋₄ haloalkyl group, a C₁₋₄ linear or branched hydroxyalkyl group, a C₃₋₄ cycloalkyl group, a group - (CH₂) ₁₋₃CN, a group - (CH₂) ₀₋₃-O- (CH₂) ₀₋ ₃-O-R⁷, a group - (CH₂) ₀₋₃-O- (linear or branched C₁₋₄ alkyl), a group - (CH₂) ₀₋₃-O- (CH₂) ₂₋₄-NR⁷R⁸, a group - (CH₂) ₀₋₃NR⁷R⁸, a group - (CH₂) ₀₋₃-NH- (CH₂) ₂₋₄NR⁷R⁸, a group -C (O) - (CH₂) ₁₋₃CN, a group -C (O) -O- (linear or branched C₁₋₄ alkyl), a group -C (O) -OH, a group -C (O), a group -C (O) - (CH₂) ₀₋₃- (linear alkyl or branched C₁₋₄), a group -C (O) - (CH₂) ₀₋₃- (phenyl), a group -C (O) -O- (CH₂) ₀₋₃- (phenyl), a group -C (O) - (CH₂) ₀₋₃- (5 to 9-membered heterocyclic, monocyclic or bicyclic, containing at least one heteroatom selected from O, S and N), a group -C (O) - ( CH₂) ₀₋₃- (5-7 membered heteroaryl containing at least one heteroatom selected from O, S and N), a group -C (O) - (CH₂) ₀₋₃-NR⁷ [CH (C₁₋ alkyl ₂)] ₀₋₃- (phenyl), a group -C (O) - (CH₂) ₀₋₃-NR¹ (CH₂) ₀₋₃- (phenyl), a group -C (O) - (CH₂) ₀ ₋₃-NR⁷ (CH₂) ₀₋₃- (5-7 membered heteroaryl containing at least one heteroatom selected from O, S and N), a group -C (O) - (CH₂) ₀₋₃-NR⁷ ( CH₂) ₀₋₃- (5 to 9-membered heterocyclic, monocyclic or bicyclic, containing at least one heteroatom selected from O, S and N), a group -C (O) - (CH₂) ₀₋₃-NR⁷R⁸, a group -C (O) - (CH₂) ₀₋₃-NR⁷- (CH₂) ₂₋₆-NR⁷R⁸, a group -C (O) - (CH₂) ₀₋₃-NR⁷- (CH₂) ₁₋₆- NR⁷- (CH₂) ₁₋₆-NR⁷R⁸, a group -NR⁷-S (O) ₂ (CH₂) ₀₋₃R⁸ , a group -S (O) ₂ (CH₂) ₀₋₃-R⁸, a group -S (O) ₂ (CH₂) ₀₋₃NR⁷R⁸, a group -S (O) ₂ (CH₂) ₀₋₃-NR⁷ ( CH₂) ₀₋₃- (phenyl), a group - (CH₂) ₀₋₃- (5-7 membered heteroaryl containing at least one heteroatom selected from O, S and N), a group - (CH₂) ₀₋ ₃- (5-7 membered heterocyclic, monocyclic or bicyclic, containing at least one heteroatom selected from O, S and N), a group - (CH₂) ₀₋₃- (phenyl) or a group - (CH₂) ₀ ₋₃-O- (CH₂) ₀₋₃- (phenyl); wherein each phenyl, heteroaryl and heterocyclic group is unsubstituted or substituted with one or more substituents selected from a hydroxyl group, a linear or branched C₁₋₄ alkyl group, a linear or branched C₁₋₄ hydroxyalkyl group, a group - (CH₂ ) ₀₋₃-O- (linear or branched C₁₋₄ alkyl), a group -C (O) -O- (linear or branched C₁₋₄ alkyl), a group -C (O) -OH, a group - C (O) - (CH₂) ₀₋₃- (linear or branched C₁₋₄ alkyl), a group -C (O) - (CH₂) ₀₋₃-NRᶠRᵍ, a group - (CH₂) ₀₋₃N (Rᶠ ) Rᵍ, a group -S (O) ₂ (CH₂) ₀₋₃ (linear or branched C₁₋₄ alkyl), a group -S (O) ₂ (CH₂) ₀₋₃NRᶠRᵍ, a group -NRᶠ-S (O ) ₂ (CH₂) ₀₋₃NRᶠRᵍ, a group -NRᶠ-S (O) ₂ (CH₂) ₀₋₃Rᵍ, a group - (CH₂) ₀₋₃-O- (CH₂) ₂₋₄-NRᶠRᵍ or a group - (CH₂) ₀₋₃- (5-7 membered heteroaryl containing at least one heteroatom selected from O, S and N); wherein the heteroaryl group is unsubstituted or substituted with one or more substituents selected from a linear or branched C₁₋₃ alkyl group or a group - (CH₂) ₀₋₃NRᶠRᵍ; and wherein Rᶠ and Rᵍ independently represents hydrogen, a linear or branched C₁₋₄ alkyl group or a linear or branched C₁₋₄ hydroxyalkyl group; each of R² and R³ independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a linear or branched C₁₋₄ alkyl group, a C₁₋₄ haloalkyl group, a C₁ linear or branched hydroxyalkyl group ₋₄, a C₁₋₄ cycloalkyl group, a C₁₋₄ alkoxy group, a -NH₂ group, a -N (CH₃) H group, or a -N (CH₃) ₂ group; R⁴ represents a hydrogen atom, a linear or branched C grupo alkyl group, a C₁₋₄ haloalkyl group, a C₁₋₄ linear or branched hydroxyalkyl group, a C₃₋₇ cycloalkyl group, a group - (CH₂) ₀₋₃ -S- (CH₂) ₀₋₃- (phenyl), a group - (CH₂) ₀₋₃-S- (CH₂) ₀₋₃- (5 to 7-membered heteroaryl containing at least one heteroatom selected from O, S and N), a group - (CH₂) ₀₋₃-O- (CH₂) ₀₋₃- (phenyl), a group - (CH₂) ₀₋₃-O- (CH₂) ₀₋₃- (heteroaryl of 5 to 7 members containing at least one heteroatom selected from O, S and N), a group - (CH₂) ₀₋₃- (phenyl), a group - (CH₂) ₀₋₃- (5 to 7 member heteroaryl containing at least one heteroatom selected from O, S and N), wherein the phenyl and heterocyclyl groups are unsubstituted or substituted

ARP140100477A 2013-02-15 2014-02-14 PIRROLOTRIAZINE DERIVATIVES AS PI3K INHIBITORS AR094797A1 (en)

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