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AR110421A1 - Derivados de pirazol como inhibidores de malt1 - Google Patents

Derivados de pirazol como inhibidores de malt1

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Publication number
AR110421A1
AR110421A1 ARP170103626A ARP170103626A AR110421A1 AR 110421 A1 AR110421 A1 AR 110421A1 AR P170103626 A ARP170103626 A AR P170103626A AR P170103626 A ARP170103626 A AR P170103626A AR 110421 A1 AR110421 A1 AR 110421A1
Authority
AR
Argentina
Prior art keywords
methyl
trifluoromethyl
oxo
pyridin
hydrogen
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Application number
ARP170103626A
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English (en)
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Janssen Biotech Inc
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Publication date
Application filed by Janssen Biotech Inc filed Critical Janssen Biotech Inc
Publication of AR110421A1 publication Critical patent/AR110421A1/es

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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • 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
    • A61K31/435—Heterocyclic 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
    • A61K31/4353—Heterocyclic 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
    • A61K31/437—Heterocyclic 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
    • 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
    • A61K31/435—Heterocyclic 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/435—Heterocyclic 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • 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
    • A61K31/435—Heterocyclic 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic 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
    • A61K31/535—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
    • A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
    • A—HUMAN NECESSITIES
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    • 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
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    • 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
    • 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
    • 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
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    • 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
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    • 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
    • C07D413/14—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
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D417/14—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 three or more hetero rings
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    • 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
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    • 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
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    • C07D491/02—Heterocyclic 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
    • C07D491/04—Ortho-condensed systems
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Epidemiology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Se describen compuestos, composiciones y métodos para tratar enfermedades, síndromes, afecciones y trastornos afectados por la modulación de MALT1. Reivindicación 1: Un compuesto de la fórmula (1), en donde R¹ se selecciona del grupo que consiste en i) naftalen-1-ilo, opcionalmente sustituido con un sustituyente flúor o amino; y ii) un heteroarilo de nueve a diez miembros que contiene de uno a cuatro heteroátomos seleccionados del grupo que consiste en O, N, y S; de manera que no más de un heteroátomo es O ó S; en donde el heteroarilo de ii) es, opcionalmente, independientemente sustituido con uno o dos sustituyentes seleccionados de deuterio, metilo, etilo, propilo, isopropilo, trifluorometilo, ciclopropilo, metoximetilo, difluorometilo, 1,1-difluoroetilo, hidroximetilo, 1-hidroxietilo, 1-etoxietilo, hidroxi, metoxi, etoxi, flúor, cloro, bromo, metiltio, ciano, amino, metilamino, dimetilamino, 4-oxotetrahidrofuran-2-ilo, 5-oxopirrolidin-2-ilo, 1,4-dioxanilo, aminocarbonilo, metilcarbonilo, metilaminocarbonilo, oxo, 1-(t-butoxicarbonil)azetidin-2-ilo, N-(metil)formamidometilo, tetrahidrofuran-2-ilo, 3-hidroxi-pirrolidin-1-ilo, pirrolidin-2-ilo, 3-hidroxiazetidinilo, azetidin-3-ilo, o azetidin-2-ilo; R² se selecciona del grupo que consiste en alquilo C₁₋₄, 1-metoxi-etilo, difluorometilo, flúor, cloro, bromo, ciano, y trifluorometilo; G¹ es N o C(R⁴); G² es N o C(R³); de manera que solo uno de G¹ y G² es N en cualquier caso; R³ se selecciona independientemente del grupo que consiste en trifluorometilo, ciano, alquilo C₁₋₄, flúor, cloro, bromo, metilcarbonilo, metiltio, metilsulfinilo, y metanosulfonilo; o, cuando G¹ es N, R³ se selecciona además de alcoxicarbonilo C₁₋₄; R⁴ se selecciona del grupo que consiste en i) hidrógeno, cuando G² es N; ii) alcoxi C₁₋₄; iii) ciano; iv) ciclopropiloxi; v) un heteroarilo seleccionado del grupo que consiste en triazolilo, oxazolilo, isoxazolilo, pirazolilo, pirrolilo, tiazolilo, tetrazolilo, oxadiazolilo, imidazolilo, 2-amino-pirimidin-4-ilo, 2H-[1,2,3]triazolo[4,5-c]piridin-2-ilo, 2H-[1,2,3]triazolo[4,5-b]piridin-2-ilo, 3H-[1,2,3]triazolo[4,5-b]piridin-3-ilo, 1H-[1,2,3]triazolo[4,5-c]piridin-1-ilo, en donde el heteroarilo es opcionalmente sustituido con uno o dos sustituyentes independientemente seleccionados de oxo, alquilo C₁₋₄, carboxi, metoxicarbonilo, aminocarbonilo, hidroximetilo, aminometilo, (dimetilamino)metilo, amino, metoximetilo, trifluorometilo, amino(alquilo C₂₋₄) amino, o ciano; vi) 1-metil-piperidin-4-iloxi; vii) 4-metil-piperazin-1-ilcarbonilo; viii) (4-aminobutil)aminocarbonilo; ix) (4-amino)butoxi; x) 4-(4-aminobutil)-piperazin-1-ilcarbonilo; xi) metoxicarbonilo; xii) 5-cloro-6-(metoxicarbonil)piridin-3-il-aminocarbonilo; xiii) 1,1-dioxo-isotiazolidin-2-ilo; xiv) 3-metil-2-oxo-2,3-dihidro-1H-imidazol-1-ilo; xv) 2-oxopirrolidin-1-ilo; xvi) (E)-(4-aminobut-1-en-1-il)-aminocarbonilo; xvii) difluorometoxi; y xviii) morfolin-4-ilcarbonilo; R⁵ se selecciona independientemente del grupo que consiste en hidrógeno, cloro, flúor, bromo, metoxi, metilsulfonilo, ciano, alquilo C₁₋₄, etinilo, morfolin-4-ilo, trifluorometilo, hidroxietilo, metilcarbonilo, metilsulfinilo, 3-hidroxi-pirrolidin-1-ilo, pirrolidin-2-ilo, 3-hidroxiazetidinilo, azetidin-3-ilo, azetidin-2-ilo, metiltio, y 1,1-difluoroetilo; o R⁴ y R⁵ pueden tomarse juntos para formar 8-cloro-4-metil-3-oxo-3,4-dihidro-2H-benzo[b][1,4]oxazin-6-ilo, 8-cloro-3-oxo-3,4-dihidro-2H-benzo[b][1,4]oxazin-6-ilo, 2-metil-1-oxo-1,2,3,4-tetrahidroisoquinolin-7-ilo, 4-metil-3-oxo-3,4-dihidro-2H-benzo[b][1,4]oxazin-6-ilo, 3-oxo-3,4-dihidro-2H-benzo[b][1,4]oxazin-6-ilo, 1-metil-1H-pirazolo[3,4-b]piridin-5-ilo, 1H-pirazolo[3,4-b]piridin-5-ilo, 2,3-dihidro-[1,4]dioxino[2,3-b]piridin-5-ilo, 1,3-dioxolo[4,5]piridina-5-ilo, 1-oxo-1,3-dihidroisobenzofuran-5-ilo, 2,2-dimetilbenzo[d][1,3]dioxol-5-ilo, 2,3-dihidrobenzo[b][1,4]dioxin-6-ilo, 1-oxoisoindolin-5-ilo, o 2-metil-1-oxoisoindolin-5-ilo, 1H-indazol-5-ilo; R⁶ es hidrógeno, alquilo C₁₋₄, flúor, 2-metoxi-etoxi, cloro, ciano, o trifluorometilo; R⁷ es hidrógeno o flúor; siempre y cuando un compuesto de la fórmula (1) es distinto de: un compuesto en donde R¹ es isoquinolin-8-ilo, R² es trifluorometilo, G¹ es C(R⁴), en donde R⁴ es 2H-1,2,3,-triazol-2-ilo, G² es N, y R⁵ es hidrógeno; un compuesto en donde R¹ es isoquinolin-8-ilo, R² es trifluorometilo, G¹ es C(R⁴), en donde R⁴ es 1H-imidazol-1-ilo, G² es N, y R⁵ es cloro; un compuesto en donde R¹ es isoquinolin-8-ilo, R² es trifluorometilo, G¹ es C(R⁴), en donde R⁴ es 1H-1,2,3-triazol-1-ilo, G² es N, y R⁵ es hidrógeno; un compuesto en donde R¹ es isoquinolin-8-ilo, R² es trifluorometilo, G¹ es C(R⁴), en donde R⁴ es hidrógeno, G² es N, y R⁵ es fluoro; un compuesto en donde R¹ es quinolin-4-ilo, R² es hidrógeno, G¹ es C(R⁴), en donde R⁴ es (2H)-1,2,3-triazol-2-ilo, G² es N, y R⁵ es cloro; o un enantiómero, diastereómero, o forma de sal farmacéuticamente aceptable de estos.
ARP170103626A 2016-12-21 2017-12-21 Derivados de pirazol como inhibidores de malt1 AR110421A1 (es)

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EP (1) EP3558969B1 (es)
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KR (1) KR102583317B1 (es)
CN (1) CN110214136A (es)
AR (1) AR110421A1 (es)
AU (2) AU2017382185C1 (es)
BR (1) BR112019012355A2 (es)
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