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AR085489A1 - Derivados de triazolopiridinas, composiciones farmaceuticas que los contienen, proceso para prepararlos, intermediarios de dicho proceso y uso de los mismos para el tratamiento de enfermedades autoinmunes e inflamatorias - Google Patents

Derivados de triazolopiridinas, composiciones farmaceuticas que los contienen, proceso para prepararlos, intermediarios de dicho proceso y uso de los mismos para el tratamiento de enfermedades autoinmunes e inflamatorias

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Publication number
AR085489A1
AR085489A1 ARP120100626A ARP120100626A AR085489A1 AR 085489 A1 AR085489 A1 AR 085489A1 AR P120100626 A ARP120100626 A AR P120100626A AR P120100626 A ARP120100626 A AR P120100626A AR 085489 A1 AR085489 A1 AR 085489A1
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AR
Argentina
Prior art keywords
alkyl
alkoxy
optionally substituted
ring
halogen
Prior art date
Application number
ARP120100626A
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English (en)
Inventor
James M Graham
Yvan Le Heurou
Michael Lyon
John E Robinson
Eli M Wallace
Bin Wang
Rui Xu
James F Blake
Robert Kirk Dlisle
Lisa A Dmeese
Original Assignee
Array Biopharma Inc
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Publication of AR085489A1 publication Critical patent/AR085489A1/es

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic 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
    • C07D471/02Heterocyclic 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
    • C07D471/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/4353Heterocyclic 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
    • A61K31/437Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/02Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/06Heterocyclic 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 carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic 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
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic 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
    • C07D487/10Spiro-condensed systems
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04Ortho-condensed systems
    • C07D491/044Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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    • C07DHETEROCYCLIC COMPOUNDS
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  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
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  • Immunology (AREA)
  • Rheumatology (AREA)
  • Dermatology (AREA)
  • Biomedical Technology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Transplantation (AREA)
  • Pulmonology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Reivindicación 1: Un compuesto de la fórmula general (1) y estereoisómeros, sales y solvatos farmacéuticamente aceptables de los mismos, donde: R1 es H, halógeno, CN, OH, alquilo C1-6, fluoroalquilo C1-6, difluoroalquilo C1-6, trifluoroalquilo C1-6, hidroxialquilo C1-6, cianoalquilo C1-6, (alcoxi C1-3)alquilo C1-6 (opcionalmente sustituido por hidroxi), di(alcoxi C1-3)alquilo C1-6, alcoxi C1-6, fluoroalcoxi C1-6, difluoroalcoxi C1-6, trifluoroalcoxi C1-6, hidroxialcoxi C2-6, cianoalcoxi C1-6, (alcoxi C1-3)alcoxi C2-6, di(alcoxi C1-3)alcoxi C2-6, (cicloalquil C3-6)metoxi, oxetanilmetoxi (opcionalmente sustituido por metilo), (alquilo C1-6)sulfanilo, -C(=O)NRaRb, -CH2C(=O)NRcRd o cicloalquilo C3-6 opcionalmente sustituido por -CH2OH o -CH2O(alquilo C1-4); Ra, Rb, Rc y Rd se seleccionan independientemente de H y alquilo C1-4; R2 es H, halógeno, CN, O, alquilo C1-6, fluoroalquilo C1-6, difluoroalquilo C1-6, trifluoroalquilo C1-6, hidroxialquilo C1-6, (alcoxi C1-3)alquilo C1-6, alcoxi C1-6 (opcionalmente sustituido por (alquilo C1-6)C(=O)O-, amino(alquilo C1-6)C(=O)O-, o fenil(C=O)O-), fluoroalcoxi C1-6, difluoroalcoxi C1-6, trifluoroalcoxi C1-6, hidroxialcoxi C2-6, (alcoxi C1-3)alcoxi C2-6, (cicloalquil C3-6)metoxi, cicloalcoxi C3-6 (opcionalmente sustituido por OH), oxetanilmetoxi (opcionalmente sustituido por metilo), tetrahidropiraniloxi, (alquil C1-6)sulfanilo, hidroxi(alquil C2-6)sulfanilo, (alquil C1-3sulfanil)alcoxi C2-6, -COOH, hetAr1, -C(=O)NReRf, -NReC(=O)Rf, oxetanilo o ciclopropilo opcionalmente sustituido por -CH2OH o -CH2O(alquilo C1-6); o R1 y R2 junto con los átomos a los que están unidos forman un anillo heterocíclico de 5 - 6 miembros que tiene 1 - 2 heteroátomos del anillo que se seleccionan independientemente de O y N donde dicho anillo se sustituye opcionalmente por alquilo C1-4; hetAr1 es un anillo heteroarilo de 5 - 6 miembros que tiene uno o dos átomos de nitrógeno del anillo y que está opcionalmente sustituido por uno o más grupos seleccionados de alquilo C1-6; Re y Rf son independientemente H, alquilo C1-6 o ciclopropilo opcionalmente sustituido por alquilo C1-4; R3 es H, halógeno o alquilo C1-6; R4 es un compuesto de fórmula (2); R5 es CF3, CH2F, CHF2, metilo o etilo; R5a es H o metilo; o R5 y R5a, junto con el átomo al cual están unidos forman un anillo ciclopropilo; R6 es H, NH2, OH, (alquilo C1-6)NH-, fluoro(alquilo C1-6)NH-, hidroxi(alquilo C1-6)NH-, (cicloalquilo C3-6)CH2NH-, (alquilo C1-6)C(=O)NH-, (alquilo C1-6)OC(=O)NH- (opcionalmente sustituido por 5-metil-2-oxo-1,3-dioxol-4-ilo) o aminoalquilo C1-6-; R7 es H, hidroxialquilo C1-6; o R6 y R7 junto con el átomo al que están unido forman un heterociclo espirocíclico de 5 - 6 miembros que tiene un átomo de nitrógeno en el anillo; R8 es H, halógeno, OH o alcoxi C1-6; o R6 y R8 junto con los átomos de carbono a los que están unidos forman un anillo ciclopropilo opcionalmente sustituido por NH2; R9 es H; o R6 y R9 juntos forman un grupo de enlace que tiene la fórmula -CH2NH- que une los átomos de carbono a los que están unidos; y R10 es H o halógeno.
ARP120100626A 2011-02-25 2012-02-24 Derivados de triazolopiridinas, composiciones farmaceuticas que los contienen, proceso para prepararlos, intermediarios de dicho proceso y uso de los mismos para el tratamiento de enfermedades autoinmunes e inflamatorias AR085489A1 (es)

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US (1) US8889704B2 (es)
EP (1) EP2678329B1 (es)
JP (2) JP6039585B2 (es)
KR (1) KR101940338B1 (es)
CN (1) CN103492377B (es)
AR (1) AR085489A1 (es)
AU (1) AU2012254082B2 (es)
BR (1) BR112013021675A2 (es)
CA (1) CA2828269C (es)
CL (1) CL2013002446A1 (es)
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