AR098723A1 - DERIVATIVES OF PIRAZOLOPIRIMIDIN-2-ILO AS JAK INHIBITORS - Google Patents

DERIVATIVES OF PIRAZOLOPIRIMIDIN-2-ILO AS JAK INHIBITORS

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Publication number
AR098723A1
AR098723A1 ARP140104622A ARP140104622A AR098723A1 AR 098723 A1 AR098723 A1 AR 098723A1 AR P140104622 A ARP140104622 A AR P140104622A AR P140104622 A ARP140104622 A AR P140104622A AR 098723 A1 AR098723 A1 AR 098723A1
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group
alkyl
linear
monocyclic
heteroaryl
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ARP140104622A
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Spanish (es)
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Llera Soldevila Oriol
Esteve Trias Cristina
Bach Taa Jordi
Perez Crespo Daniel
Taboada Martinez Lorena
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Almirall Sa
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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
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  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Rheumatology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Transplantation (AREA)
  • Pain & Pain Management (AREA)
  • Oncology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Hematology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Se describen derivados de pirazolopirimidin-2-ilo; así como un procedimiento para su preparación, composiciones farmacéuticas que los comprenden y su uso en terapia como inhibidores de quinasas Janus (JAK). Reivindicación 1: Un compuesto de fórmula (1), o una sal farmacéuticamente aceptable, o solvato, o N-óxido, o estereoisómero o derivado deuterado del mismo, en donde X se selecciona del grupo que consiste en -N- y grupo -CRᶜ-; G¹ se selecciona del grupo que consiste en un grupo arilo monocíclico C₅₋₈, un grupo cicloalquilo monocíclico C₃₋₈, un grupo heteroarilo monocíclico de 5 a 8 miembros que contiene al menos un heteroátomo seleccionado de O, S y N y un grupo heterocíclico monocíclico de 5 a 8 miembros que contiene al menos un heteroátomo seleccionado de O, S y N, en donde los grupos arilo, cicloalquilo, heteroarilo y heterocíclico están no sustituidos o sustituidos con uno o más sustituyentes seleccionados de un átomo de halógeno, un grupo hidroxi, un grupo -CHO, un grupo alquilo C₁₋₄, un grupo tioalquilo C₁₋₄, un grupo hidroxialquilo C₁₋₂, un grupo di(alquil C₁₋₂)amino-alquilo C₁₋₄ y un grupo -NR-SO₂;-R; L¹ se selecciona del grupo que consiste en un grupo -(CH₂)₍₀₋₁₎-, -O-, -NRˣ-(CH₂)₍₀₋₁₎-, en donde Rˣ se selecciona del grupo que consiste en un átomo de hidrógeno y un grupo alquilo C₁₋₂ opcionalmente sustituido con un grupo -(CH₂)₍₀₋₂₎NRR-; L² se selecciona del grupo que consiste en un grupo -(CH₂)ₚ-, -(CH₂)-NR-, -NR-(CH₂)-, -O-(CH₂)₍₀₋₂₎, -(CO)O-, -S- y -NR-, en donde R representa un átomo de hidrógeno o un grupo alquilo C₁₋₄ opcionalmente sustituido con un grupo seleccionado de un grupo -NRR- y un grupo fenilo en donde dicho grupo fenilo está opcionalmente sustituido con un grupo hidroxi; R¹ se selecciona del grupo que consiste en un átomo de hidrógeno, un grupo alquilo lineal o ramificado C₁₋₄ opcionalmente sustituido con un grupo -NRR, un grupo arilo monocíclico C₅₋₈, un grupo cicloalquilo monocíclico C₃₋₈, un grupo heteroarilo mono- o bi-cíclico de 5 a 14 miembros que contiene al menos un heteroátomo seleccionado de O, S y N y un grupo heterocíclico mono- o bicíclico de 5 a 14 miembros que contiene al menos un heteroátomo seleccionado de O, S y N, en donde los grupos arilo, cicloalquilo, heteroarilo y heterocíclico están no sustituidos o sustituidos con uno o más sustituyentes seleccionados del grupo que consiste en un átomo de halógeno, un grupo hidroxi, un grupo alquilo lineal o ramificado C₁₋₆, un grupo hidroxialquilo lineal o ramificado C₁₋₆, un grupo alcoxi lineal o ramificado C₁₋₄, un grupo -(O)₍₀₋₁₎(CH₂)₍₀₋₃₎-NRR, un grupo -CO-O-Rᵈ, un grupo -CH₂-Rᵉ, un grupo heterocíclico monocíclico de 5 a 8 miembros que contiene al menos un heteroátomo seleccionado de O, S y N y un grupo heteroarilo monocíclico de 5 a 8 miembros que contiene al menos un heteroátomo seleccionado de O, S y N en donde dichos grupos heterocíclicos y heteroarilo están opcionalmente sustituidos de manera independiente con uno o más sustituyentes seleccionados del grupo que consiste en un grupo alquilo C₁₋₂, grupo -C(O)O-(alquilo C₁₋₂) y un grupo -NRR; R² se selecciona del grupo que consiste en un átomo de hidrógeno, un átomo de halógeno y un grupo alquilo C₁₋₄; R³ se selecciona del grupo que consiste en un átomo de hidrógeno, un grupo alquilo C₁₋₄ y un grupo -(CH₂)₍₂₋₄₎NRR-; G² se selecciona del grupo que consiste en un grupo arilo monocíclico C₅₋₈, un grupo cicloalquilo monocíclico C₃₋₈, un grupo heteroarilo monocíclico de 5 a 8 miembros que contiene al menos un heteroátomo seleccionado de O, S y N y un grupo heterocíclico monocíclico de 5 a 8 miembros que contiene al menos un heteroátomo seleccionado de O, S y N, en donde los grupos arilo, cicloalquilo, heteroarilo y heterocíclico están no sustituidos o sustituidos con uno o más sustituyentes seleccionados de un átomo de halógeno, un grupo hidroxi, un grupo alquilo C₁₋₄, un grupo alcoxi C₁₋₄, un grupo hidroxialquilo C₁₋₂, un grupo -NRR y un grupo de fórmula (2), en donde L³ representa un enlace directo, grupo -CO-, o un grupo -C(O)O-; R⁴ se selecciona del grupo que consiste en un grupo hidroxi, un grupo -(CH₂)₍₀₋₁₎-CN, un grupo -CF₃, un grupo alquilo lineal o ramificado C₁₋₄, un grupo alcoxi lineal o ramificado C₁₋₄, un grupo hidroxialquilo C₁₋₄ lineal o ramificado y un grupo alquilamino C₁₋₄ en donde los grupos alquilo e hidroxialquilo están opcionalmente sustituidos con uno o más grupos metilo; Rᵃ y Rᵇ se seleccionan independientemente del grupo que consiste en un átomo de hidrógeno, un grupo hidroxi, un grupo alquilo C₁₋₄ o Rᵃ y Rᵇ junto con el átomo de carbono al que están unidos forman un grupo cicloalquilo C₃₋₆ o un grupo heterocíclico de 3 a 5 miembros que contiene al menos un heteroátomo seleccionado de N, O y S; R⁵ se selecciona del grupo que consiste en un átomo de hidrógeno y un grupo alquilo lineal o ramificado C₁₋₄; Rᶜ se selecciona del grupo que consiste en un átomo de hidrógeno, un grupo alquilo C₁₋₄, un grupo alcoxi C₁₋₄, un grupo arilo C₅₋₈, y un grupo heteroarilo de 5 a 8 miembros que contiene al menos un heteroátomo seleccionado de O, S y N y un grupo -NRR, en donde el grupo heteroarilo está opcionalmente sustituido con uno o más sustituyentes seleccionados del grupo formado por un átomo de halógeno y un grupo alquilo C₁₋₄; Rᵈ representa un grupo alquilo lineal o ramificado C₁₋₄ opcionalmente sustituido con uno o más sustituyentes seleccionados de un grupo fenilo, un grupo metilo y un -NRR, o Rᵈ representa un grupo heterocíclico monocíclico de 5 a 8 miembros que contiene al menos un heteroátomo seleccionado de O, S y N opcionalmente sustituido por un grupo alquilo C₁₋₂; Rᵉ se selecciona del grupo que consiste en un grupo arilo monocíclico C₅₋₈ y un grupo heteroarilo monocíclico de 5 a 8 miembros que contiene al menos un heteroátomo seleccionado de O, S y N, cuyo anillo cíclico está opcionalmente sustituido con uno o más sustituyentes seleccionados de un grupo hidroxi, un grupo alquilo lineal o ramificado C₁₋₄ y un grupo -CF₃; cada uno de R y R de manera independiente representa un átomo de hidrógeno, un grupo alquilo C₁₋₄ o un grupo cicloalquilo C₃₋₆, o R y R junto con el átomo de nitrógeno al que están unidos forman un grupo heterocíclico que contiene N, de 4 a 6 miembros, que contiene opcionalmente uno o más heteroátomos adicionales seleccionados de N, S y O, y opcionalmente sustituido con un grupo dimetilamino; n, m y q independientemente tienen un valor de 0 ó 1; p tiene un valor de o, 1 ó 2.Derivatives of pyrazolopyrimidin-2-yl are described; as well as a procedure for its preparation, pharmaceutical compositions comprising them and their use in therapy as Janus kinase inhibitors (JAK). Claim 1: A compound of formula (1), or a pharmaceutically acceptable salt, or solvate, or N-oxide, or stereoisomer or deuterated derivative thereof, wherein X is selected from the group consisting of -N- and group -CRᶜ -; G¹ is selected from the group consisting of a C₅₋₈ monocyclic aryl group, a C₃₋₈ monocyclic cycloalkyl group, a 5 to 8 membered monocyclic heteroaryl group containing at least one heteroatom selected from O, S and N and a heterocyclic group 5 to 8-membered monocyclic containing at least one heteroatom selected from O, S and N, wherein the aryl, cycloalkyl, heteroaryl and heterocyclic groups are unsubstituted or substituted with one or more substituents selected from a halogen atom, a group hydroxy, a -CHO group, a C₁₋₄ alkyl group, a C₁₋₄ thioalkyl group, a C₁₋₂ hydroxyalkyl group, a di (C₁₋₂ alkyl) amino-C alquilo alkyl group and a -NR-SO₂ group ; -R; L¹ is selected from the group consisting of a group - (CH₂) ₍₀₋₁₎-, -O-, -NRˣ- (CH₂) ₍₀₋₁₎-, where Rˣ is selected from the group consisting of an atom of hydrogen and a C₁₋₂ alkyl group optionally substituted with a group - (CH₂) ₍₀₋₂₎NRR-; L² is selected from the group consisting of a group - (CH₂) ₚ-, - (CH₂) -NR-, -NR- (CH₂) -, -O- (CH₂) ₍₀₋₂₎, - (CO) O -, -S- and -NR-, wherein R represents a hydrogen atom or a C₁₋₄ alkyl group optionally substituted with a group selected from a group -NRR- and a phenyl group wherein said phenyl group is optionally substituted with a hydroxy group; R¹ is selected from the group consisting of a hydrogen atom, a linear or branched C₁₋₄ alkyl group optionally substituted with a -NRR group, a C₅₋₈ monocyclic aryl group, a C₃₋₈ monocyclic cycloalkyl group, a mono heteroaryl group - or 5 to 14-membered bi-cyclic containing at least one heteroatom selected from O, S and N and a 5- to 14-membered mono- or bicyclic heterocyclic group containing at least one heteroatom selected from O, S and N, wherein the aryl, cycloalkyl, heteroaryl and heterocyclic groups are unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a linear or branched C₁₋₆ alkyl group, a linear hydroxyalkyl group or branched C₁₋₆, a linear or branched alkoxy group C₁₋₄, a group - (O) ₍₀₋₁₎ (CH₂) ₍₀₋₃₎-NRR, a group -CO-O-Rᵈ, a group - CH₂-Rᵉ, a monocyclic heterocyclic group 5 to 8-member lico containing at least one heteroatom selected from O, S and N and a monocyclic heteroaryl group of 5 to 8 members containing at least one heteroatom selected from O, S and N wherein said heterocyclic and heteroaryl groups are optionally independently substituted with one or more substituents selected from the group consisting of a C₁₋₂ alkyl group, -C (O) O- (C₁₋₂ alkyl) group and a -NRR group; R² is selected from the group consisting of a hydrogen atom, a halogen atom and a C₁₋₄ alkyl group; R³ is selected from the group consisting of a hydrogen atom, a C₁₋₄ alkyl group and a group - (CH₂) ₍₂₋₄₎NRR-; G² is selected from the group consisting of a C₅₋₈ monocyclic aryl group, a C₃₋₈ monocyclic cycloalkyl group, a 5 to 8 membered monocyclic heteroaryl group containing at least one heteroatom selected from O, S and N and a heterocyclic group 5 to 8-membered monocyclic containing at least one heteroatom selected from O, S and N, wherein the aryl, cycloalkyl, heteroaryl and heterocyclic groups are unsubstituted or substituted with one or more substituents selected from a halogen atom, a group hydroxy, a C₁₋₄ alkyl group, a C₁₋₄ alkoxy group, a C₁₋₂ hydroxyalkyl group, a -NRR group and a group of formula (2), wherein L³ represents a direct bond, -CO- group, or a group -C (O) O-; R⁴ is selected from the group consisting of a hydroxy group, a group - (CH₂) ₍₀₋₁₎-CN, a group -CF₃, a linear or branched alkyl group C₁₋₄, a linear or branched alkoxy group C₁₋₄ , a linear or branched C₁₋₄ hydroxyalkyl group and a C₁₋₄ alkylamino group wherein the alkyl and hydroxyalkyl groups are optionally substituted with one or more methyl groups; Rᵃ and Rᵇ are independently selected from the group consisting of a hydrogen atom, a hydroxy group, a C₁₋₄ or Rᵃ alkyl group and together with the carbon atom to which they are attached form a C₃₋₆ cycloalkyl group or a group 3 to 5 member heterocyclic containing at least one heteroatom selected from N, O and S; R⁵ is selected from the group consisting of a hydrogen atom and a linear or branched C₁₋₄ alkyl group; Rᶜ is selected from the group consisting of a hydrogen atom, a C₁₋₄ alkyl group, a C₁₋₄ alkoxy group, a C₅₋₈ aryl group, and a 5- to 8-membered heteroaryl group containing at least one selected heteroatom of O, S and N and a -NRR group, wherein the heteroaryl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a C₁₋₄ alkyl group; Rᵈ represents a linear or branched C₁₋₄ alkyl group optionally substituted with one or more substituents selected from a phenyl group, a methyl group and a -NRR, or Rᵈ represents a 5- to 8-membered monocyclic heterocyclic group containing at least one heteroatom selected from O, S and N optionally substituted by a C₁₋₂ alkyl group; Rᵉ is selected from the group consisting of a C₅₋₈ monocyclic aryl group and a 5- to 8-membered monocyclic heteroaryl group containing at least one heteroatom selected from O, S and N, whose cyclic ring is optionally substituted with one or more substituents selected from a hydroxy group, a linear or branched C₁₋₄ alkyl group and a -CF₃ group; each of R and R independently represents a hydrogen atom, a C₁₋₄ alkyl group or a C₃₋₆ cycloalkyl group, or R and R together with the nitrogen atom to which they are attached form a heterocyclic group containing N , 4 to 6 members, optionally containing one or more additional heteroatoms selected from N, S and O, and optionally substituted with a dimethylamino group; n, m and q independently have a value of 0 or 1; p has a value of o, 1 or 2.

ARP140104622A 2013-12-11 2014-12-11 DERIVATIVES OF PIRAZOLOPIRIMIDIN-2-ILO AS JAK INHIBITORS AR098723A1 (en)

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TW201705961A (en) * 2015-06-11 2017-02-16 阿爾米雷爾有限公司 2-(pyrazolopyridin-3-yl)pyrimidine derivatives as JAK inhibitors
UA119835C2 (en) 2016-02-24 2019-08-12 Пфайзер Інк. Pyrazolo[1,5-a]pyrazin-4-yl derivatives as jak-inhibitors
EP3668858A1 (en) 2017-08-14 2020-06-24 Pfizer Inc Pyrazolo[1,5-a]pyrazin-4-yl and related derivatives
CN107400087B (en) * 2017-09-15 2019-12-13 济南美高生物医药科技有限公司 preparation method of 1- (2- (4- (chloromethyl) phenoxy) ethyl) azepane hydrochloride
CN110305024B (en) * 2018-03-27 2021-09-28 鲁南制药集团股份有限公司 Synthetic method of Beloraib intermediate
JP2022518912A (en) * 2019-01-27 2022-03-17 ソル － ゲル テクノロジーズ リミテッド Treatment of skin disorders with topical tapinarov combination composition
IL292943A (en) * 2019-11-15 2022-07-01 Ildong Pharmaceutical Co Ltd Glp-1 receptor agonist and use thereof

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UY33213A (en) * 2010-02-18 2011-09-30 Almirall Sa PIRAZOL DERIVATIVES AS JAK INHIBITORS
WO2013025628A1 (en) * 2011-08-15 2013-02-21 Ligand Pharmaceuticals Incorporated Janus kinase inhibitor compounds and methods

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