AR098846A1 - Inhibidores del transporte de glucosa - Google Patents

Inhibidores del transporte de glucosa

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Publication number
AR098846A1
AR098846A1 ARP140104777A ARP140104777A AR098846A1 AR 098846 A1 AR098846 A1 AR 098846A1 AR P140104777 A ARP140104777 A AR P140104777A AR P140104777 A ARP140104777 A AR P140104777A AR 098846 A1 AR098846 A1 AR 098846A1
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Argentina
Prior art keywords
alkyl
group
heteroaryl
halo
phenyl
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ARP140104777A
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English (en)
Inventor
Dr Heisler Iring
Dr Mller Thomas
Dr Siebeneicher Holger
Dr Buchmann Bernd
Dr Cleve Arwed
Dr Gnther Judith
Dr Koppitz Marcus
Dr Heroult Melanie
Dr Neuhaus Roland
Dr Petrul Heike
Dr Quanz-Schffel Maria
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Bayer Pharma AG
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Publication of AR098846A1 publication Critical patent/AR098846A1/es

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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
    • C07D401/02—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
    • 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
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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    • 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
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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    • 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
    • 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
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    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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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
    • 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
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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    • 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
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    • 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
    • C07D417/14—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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D495/10—Spiro-condensed systems

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  • Pain & Pain Management (AREA)
  • Rheumatology (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

Compuestos químicos que inhiben al transportador de glucosa 1 (GLUT1); métodos para preparar dichos compuestos; composiciones farmacéuticas y combinaciones que comprenden dichos compuestos; uso de dichos compuestos para fabricar una composición farmacéutica para el tratamiento o profilaxis de una enfermedad; y compuestos intermediarios que son útiles en la preparación de dichos compuestos. Reivindicación 1: Un compuesto de fórmula general (1), donde: R¹ representa un grupo C₁₋₃-alquilo, halo-C₁₋₃-alquilo, ciano, -C(=O)O-R¹⁰ o -C(=O)N(R¹⁰ᵃ)R¹⁰ᵇ; R² representa un grupo C₁₋₃-alquilo, halo-C₁₋₃-alquilo, ciano, -C(=O)O-R¹⁰ o -C(=O)N(R¹⁰ᵃ)R¹⁰ᵇ; R³ representa un grupo seleccionado entre: arilo, heteroarilo, C₅₋₆-cicloalquilo, y heterocicloalquilo de 5 ó 6 miembros; donde dicho grupo heterocicloalquilo de 5 ó 6 miembros está opcionalmente benzocondensado; donde dicho grupo arilo, heteroarilo, C₅₋₆-cicloalquilo, y heterocicloalquilo de 5 ó 6 miembros está opcionalmente sustituido, una o más veces, en forma idéntica o diferente, con -(L²)ₚ-R⁷; y donde dos grupos -(L²)ₚ-R⁷, en el caso de estar presentes en posición orto entre si en un grupo arilo o heteroarilo opcionalmente forman un puente seleccionado entre: *-C₃₋₈-alquilen-*, *-O(CH₂)₂O-*, *-O(CH₂)O-*, *-O(CF₂)O-*, *-CH₂C(R¹⁰ᵃ)(R¹⁰ᵇ)O-*, *-C(=O)N(R¹⁰ᵃ)CH₂-*, *-N(R¹⁰ᵃ)C(=O)CH₂O-*, *-NHC(=O)NH-*; donde cada * representa el punto de unión a dicho grupo arilo o heteroarilo; R⁴ᵃ representa un átomo de hidrógeno o un átomo de halógeno o un grupo seleccionado entre: ciano, hidroxi, C₁₋₃-alquilo, halo-C₁₋₃-alquilo, C₁₋₃-alcoxi, halo-C₁₋₃-alcoxi, C₃₋₇-cicloalquilo, heterocicloalquilo de entre 4 y 7 miembros, -C(=O)-OR¹⁰, -C(=O)N(R¹⁰ᵃ)R¹⁰ᵇ, -C(=O)-N(R¹⁰ᵃ)-S(=O)₂-R¹⁰, -SR¹⁰, -S(=O)-R¹⁰, -S(=NR¹¹)-R¹⁰, -S(=O)₂-R¹⁰, -S(=O)₂-N(R¹⁰ᵃ)R¹⁰ᵇ, -S(=O)(=NR¹¹)-R¹⁰, -N(R¹⁰ᵃ)R¹⁰ᵇ; R⁴ᵇ representa un átomo de hidrógeno o un grupo seleccionado entre: C₁₋₃-alcoxi, C₁₋₃-alquilo, ciano; o R⁴ᵃ y R⁴ᵇ forman juntos un grupo -C₃₋₅-alquileno; R⁵ᵃ, R⁵ᵇ, R⁵ᶜ, R⁵ᵈ en forma independiente entre sí representan un átomo de hidrógeno, un átomo de halógeno o un grupo seleccionado entre: ciano, -NO₂, C₁₋₃-alquilo, halo-C₁₋₃-alquilo, C₁₋₃-alcoxi, halo-C₁₋₃-alcoxi, fenilo, heteroarilo, -C(=O)R¹⁰, -C(=O)N(H)R¹⁰, -C(=O)N(R¹⁰ᵃ)R¹⁰ᵇ, -C(=O)O-R¹⁰, -N(R¹⁰ᵃ)R¹⁰ᵇ, -N(H)C(=O)R¹⁰, -N(R¹⁰ᵃ)C(=O)R¹⁰ᵇ, -N(H)C(=O)N(R¹⁰ᵃ)R¹⁰ᵇ, -N(R¹⁰ᵃ)C(=O)N(R¹⁰ᵇ)R¹⁰ᶜ, -N(R¹⁰ᵃ)C(=O)C(=O)N(R¹⁰ᵇ)R¹⁰ᶜ, -N(H)C(=O)OR¹⁰, -N(R¹⁰ᵃ)C(=O)OR¹⁰ᵇ, -N(H)S(=O)₂R¹⁰, -N(R¹⁰ᵃ)S(=O)₂R¹⁰ᵇ, -OR¹⁰, -O(C=O)R¹⁰, -O(C=O)N(R¹⁰ᵃ)R¹⁰ᵇ, -O(C=O)OR¹⁰, -SR¹⁰, -S(=O)R¹⁰, -S(=O)₂R¹⁰, -S(=O)₂N(H)R¹⁰, -S(=O)₂N(R¹⁰ᵃ)R¹⁰ᵇ o -S(=O)(=NR¹⁰ᵃ)R¹⁰ᵇ, donde dicho grupo fenilo o heteroarilo está opcionalmente sustituido una o más veces, en forma idéntica o diferente, con un grupo seleccionado entre: halo, ciano, C₁₋₃-alquilo, halo-C₁₋₃-alquilo, C₁₋₃-alcoxi; R⁶ representa un átomo de hidrógeno o un grupo seleccionado entre: C₁₋₃-alquilo, C₁₋₃-alcoxi-(L²)-, hidroxi-C₁₋₃-alquilo, aril-(L²)-, heteroaril-(L²)-; R⁷ representa un grupo seleccionado entre: oxo, C₁₋₆-alquilo, C₃₋₇-cicloalquilo, heterocicloalquilo de entre 4 y 7 miembros, halo-C₁₋₄-alquilo, hidroxi-C₁₋₄-alquilo, ciano-C₁₋₄-alquilo, C₂₋₄-alquenilo, C₂₋₄-alquinilo, C₁₋₄-alcoxi, halo-C₁₋₄-alcoxi, -OH, -CN, halo, -C(=O)R⁸, -C(=O)-O-R⁸, -C(=O)N(R⁸ᵃ)R⁸ᵇ, -N(R¹⁰ᵃ)R¹⁰ᵇ, -S(=O)₂R⁸, -S(=O)(=NR¹¹)-R¹⁰, fenilo, heteroarilo de 5 ó 6 miembros; R⁸ representa un átomo de hidrógeno o un grupo C₁₋₆-alquilo, halo-C₁₋₃-alquilo, ciano-C₁₋₄-alquilo, C₁₋₃-alcoxi-C₁₋₃-alquilo, C₃₋₇-cicloalquilo, fenilo, heteroarilo de 5 ó 6 miembros o bencilo; R⁸ᵃ, R⁸ᵇ representan, en forma independiente entre sí, un átomo de hidrógeno, o un grupo C₁₋₁₀-alquilo, C₃₋₇-cicloalquilo, (C₃₋₇-cicloalquil)-(L³)-, C₃₋₆-alquenilo, C₃₋₆-alquinilo, heterocicloalquilo de entre 4 y 10 miembros, (heterocicloalquilo de entre 4 y 10 miembros)-(L³)-, fenilo, heteroarilo, fenil-(L³)-, (fenil)-O-(L³)-, heteroaril-(L³)-, o (aril)-(heterocicloalquilo de entre 4 y 10 miembros)-; donde dicho grupo C₁₋₁₀-alquilo, C₃₋₇-cicloalquilo, (C₃₋₇-cicloalquil)-(L³)-, C₃₋₆-alquenilo, C₃₋₆-alquinilo, heterocicloalquilo de entre 4 y 10 miembros, (heterocicloalquilo de entre 14 y 10 miembros)-(L³)-, fenilo, heteroarilo, fenil-(L³)-, (fenil)-O-(L³)-, heteroaril-(L³)-, y (aril)-(heterocicloalquilo de entre 4 y 10 miembros)- está opcionalmente sustituido una o más veces, en forma idéntica o diferente, con R⁹; o R⁸ᵃ y R⁸ᵇ, junto con el átomo de nitrógeno al cual se unen, representan un grupo heterocicloalquilo de entre 4 y 10 miembros, donde dicho grupo heterocicloalquilo de entre 4 y 10 miembros está opcionalmente sustituido una o más veces, en forma idéntica o diferente, con R⁹; R⁹ representa un átomo de halógeno, o un grupo oxo, C₁₋₃-alquilo, halo-C₁₋₃-alquilo, hidroxi-C₁₋₃-alquilo, -CN, -C(=O)R¹⁰, -C(=O)N(H)R¹⁰, -C(=O)N(R¹⁰ᵃ)R¹⁰ᵇ, -C(=O)O-R¹⁰, -N(R¹⁰ᵃ)R¹⁰ᵇ, -NO₂, -N(H)C(=O)R¹⁰, -N(R¹⁰ᵃ)C(=O)R¹⁰ᵇ, -N(H)C(=O)N(R¹⁰ᵃ)R¹⁰ᵇ, -N(R¹⁰ᵃ)C(=O)N(R¹⁰ᵇ)R¹⁰ᶜ, -N(H)C(=O)OR¹⁰, -N(R¹⁰ᵃ)C(=O)OR¹⁰ᵇ, -N(H)S(=O)₂R¹⁰, -N(R¹⁰ᵃ)S(=O)₂R¹⁰ᵇ, -OR¹⁰, -O(C=O)R¹⁰, -O(C=O)N(R¹⁰ᵃ)R¹⁰ᵇ, -O(C=O)OR¹⁰, -SR¹⁰, -S(=O)R¹⁰, -S(=O)₂R¹⁰, -S(=O)₂N(H)R¹⁰, -S(=O)₂N(R¹⁰ᵃ)R¹⁰ᵇ, -S(=O)(=NR¹⁰ᵃ)R¹⁰ᵇ o tetrazolilo; o dos grupos R⁹ presentes en posición orto entre sí en un anillo fenilo o heteroarilo forman un puente seleccionado entre: *-C₃₋₅-alquilen-*, *-O(CH₂)₂O-*, *-O(CH₂)O-*, *-O(CF₂)O-*, *-CH₂C(R¹⁰ᵃ)(R¹⁰ᵇ)O-*, *-C(=O)N(R¹⁰ᵃ)CH₂-*, *-N(R¹⁰ᵃ)C(=O)CH₂O-*, *-NHC(=O)NH-*; donde cada * representa el punto de unión a dicho anillo fenilo o heteroarilo; R¹⁰, R¹⁰ᵃ, R¹⁰ᵇ, R¹⁰ᶜ representan, en forma independiente entre si, un átomo de hidrógeno o un grupo seleccionado entre: C₁₋₃-alquilo, halo-C₁₋₃-alquilo, hidroxi-C₁₋₃-alquilo, C₁₋₃-alcoxi-C₁₋₃-alquilo, C₃₋₇-cicloalquilo, donde dicho grupo C₁₋₃-alquilo está opcionalmente sustituido una vez con -N(R¹²)R¹²ᵃ; o R¹⁰ᵃ y R¹⁰ᵇ, junto con el átomo de nitrógeno al cual se unen, representan un grupo heterocicloalquilo de entre 4 y 7 miembros, donde dicho grupo heterocicloalquilo de entre 4 y 7 miembros está opcionalmente sustituido una o más veces, en forma idéntica o diferente, con R¹³; R¹¹ representa un átomo de hidrógeno o un grupo ciano, C₁₋₃-alquilo, -C(=O)R¹⁰, -C(=O)N(H)R¹⁰, -C(=O)N(R¹⁰ᵃ)R¹⁰ᵇ o -C(=O)O-R¹⁰; R¹², R¹²ᵃ representan, en forma independiente entre sí, un átomo de hidrógeno o un grupo C₁₋₃-alquilo, o, R¹², R¹²ᵃ junto con el átomo de nitrógeno al cual se unen, representan un grupo heterocicloalquilo de entre 4 y 7 miembros; R¹³ representa un átomo de halógeno o un grupo ciano, hidroxi, oxo, C₁₋₃-alquilo, trifluorometilo, -C(=O)R¹⁰ o -C(=O)O-R¹⁰; L¹ representa un grupo seleccionado entre: -C₁₋₄-alquileno, -CH₂-CH=CH-, -C(fenil)(H)-, -CH₂-CH₂-O-, -CH₂-C(=O)-N(H)-, -CH₂-C(=O)-N(R¹⁰ᵃ)-; L² representa un grupo seleccionado entre: -CH₂-, -CH₂-CH₂-, -CH₂-CH₂-CH₂-; L³ representa un grupo -C₁₋₆-alquileno; p es el número entero 0 ó 1; o un tautómero, un estereoisómero, un N-óxido, un hidrato, un solvato, o una sal del mismo, o una mezcla de los mismos.
ARP140104777A 2013-12-20 2014-12-19 Inhibidores del transporte de glucosa AR098846A1 (es)

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US (1) US20170037028A1 (es)
EP (1) EP3083598A1 (es)
JP (1) JP2017500333A (es)
CN (1) CN106029647A (es)
AR (1) AR098846A1 (es)
CA (1) CA2934391A1 (es)
UY (1) UY35905A (es)
WO (1) WO2015091428A1 (es)

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