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AR071920A1 - Compuestos derivados de piridina, proceso para su preparacion, una composicion farmaceutica que lo comprende , metodo para tratar un estado de enfermedad - Google Patents

Compuestos derivados de piridina, proceso para su preparacion, una composicion farmaceutica que lo comprende , metodo para tratar un estado de enfermedad

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Publication number
AR071920A1
AR071920A1 ARP090101896A ARP090101896A AR071920A1 AR 071920 A1 AR071920 A1 AR 071920A1 AR P090101896 A ARP090101896 A AR P090101896A AR P090101896 A ARP090101896 A AR P090101896A AR 071920 A1 AR071920 A1 AR 071920A1
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AR
Argentina
Prior art keywords
alkyl
alkoxy
heterocyclyl
optionally substituted
heteroaryl
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Application number
ARP090101896A
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English (en)
Inventor
Glen Andrews
Rhona Jane Cox
Hitesh Jayantilal Sanganee
Premji Meghani
Daniel Jon Warner
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Astrazeneca Ab
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Publication date
Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of AR071920A1 publication Critical patent/AR071920A1/es

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    • 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
    • A61P11/02—Nasal agents, e.g. decongestants
    • 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
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • 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
    • A61P37/08—Antiallergic agents
    • 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
    • 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
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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
    • 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
    • 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
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D417/02—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 two hetero rings
    • C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Dermatology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Otolaryngology (AREA)
  • Biomedical Technology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (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)

Abstract

Un proceso para preparar el compuesto, uso de un compuesto de este tipo en el tratamiento de un estado e enfermedad mediado por PDE4 y un producto farmaceutico. Estos compuestos son utiles en el tratamiento de trastornos inflamatorios e inmunes. Reivindicacion 1: Un compuesto car4cterizado porque es de la formula (1) donde: R1 es NR7C(O)R8, NR7S(O)2R8 o NR9R10; R2 es hidrogeno o alquil C1-6; R3 es hidrogeno, halogeno, alquil C1-4 o alcoxi C1-4; R4 es hidrogeno, halogeno, ciano, hidroxi, alquil C1-4, alcoxi C1-4, CF3, OCF3, alquiltio C1-4, S(O)(alquil C1-4), S(O)2(alquil C1-4), CO2H o CO2(alquil C1-4); R5 es alquil C1-6(sustituido por NR11R12 o heterociclil), alcoxi C1-6 (sustituido por NR11R12 o heterociclil), cicloalquil C3-6 (sustituido por NR11R12 o heterociclil) o heterociclil; a condicion de que si R5 incluye un heterociclil entonces dicho heterociclil comprende uno o m s  tomos de nitrogeno del anillo; y que si dicho heterociclil est  unido directamente a traves de un nitrogeno del anillo: al alquil, alcoxi o cicloalquil de R5, o al anillo de fenil de la formula (1) al cual R5 est  directamente unido, entonces dicho heterociclil tiene al menos dos hetero tomos del anillo, o tiene un sustituyente NR46R47; R6 es hidrogeno, halogeno, ciano, hidroxi, SH, alquil C1-4, alcoxi C1-4, CF3, OCF3, C(O)H, alquiltio C1-6, S(O)(alquil C1-6), S(O)2(alquil C1-6), CO2H, CO2(alquil C1-6), NR13R14, alquil C1-6 (opcionalmente sustituido por halogeno, OH, CO2H, NR15R16, NHC(O)O(alquil C1-6), OS(O)2(alquil C1-6) o heterociclil), alcoxi C1-6 (opcionalmente sustituido por halogeno, OH, CO2H, NR15R16 o heterociclil), cicloalquil C3-6 (opcionalmente sustituido por halogeno, OH. CO2H, NR15R16 o heterociclil) o heterociclil; R7 es hidrogeno o alquil C1-6 (opcionalmente sustituido por NR26R27); R8 es alquil C1-6 (opcionalmente sustituido por hidroxil, alcoxi C1-6, NR21R22, heterociclil {opcionalmente sustituido por oxo, hidroxi, alquil C1-6, CO2(alquil C1-6), aril, heteroaril, aril(alquil C1-4), heterociclil o C(O)(alquil C1-4)fenil}, aril, heteroaril, cicloalquil C3-7, cicloalquil C3-7(alquil C1-4), CO2H, CO2(alquil C1-4), aril(alcoxi C1-4), aril(alquiltio C1-4), S(O)2(alquil C1-6), NHC(O)heteroaril o NHC(O)R23}, alcoxi C1-6, cicloalquil C3-6 {opcionalmente sustituido por hidroxil, NR24R25 o alquil C1-6}, heterociclil {opcionalmente sustituido por oxo, hidroxi, alquil C1-6, amino, aril, heteroaril, aril(alquil C1-4), heteroaril(alquil C1-4), heterociclil o C(O)(alquil C1-4)fenil}, aril(alquil C1-4) {sustituido por amino(alquil C1-4)}, aril o heteroaril; R9 es hidrogeno, alquil C1-6 (opcionalmente sustituido por aril o heteroaril), R10 es hidrogeno, alquil C1-6 (opcionalmente sustituido por hidroxil, alcoxi C1-6, aril, ariloxi, fenil(alcoxi C1-6), heteroaril, cicloalquil C3-10, CO2H, CO2(alquil C1-6), NHC(O)O(alquil C1-6) o NHC(O)R23), alcoxi C1-6, cicloalquil C3-6 (opcionalmente sustituido por hidroxi, alquil C1-6, fenil, fenil(alquil C1-6), heteroaril o heteroaril(alquil C1-6)), heterociclil (opcionalmente sustituido por alquil C1-6, C(O)NH2 o fenil(alquil C1-6)), aril o heteroaril; R21 y R22 son, independientemente, hidrogeno, alquil C1-6 o fenil(alquil C1-4); R23 es alquil C1-6 o fenil; las mitades fenil, aril y heteroaril precedentes de R5, R8, R9, R10, R23, R21 y R22 son, independientemente, opcionalmente sustituidas por: halogeno, ciano, nitro, CF3, hidroxi, S(O)qR26, OC(O)NR27R28, NR29R30, NR31C(O)R32, NR33C(O)NR34R35, S(O)2NR36R37, NR38S(O)2R39, C(O)NR40R41, C(O)R42, CO2R43, NR44CO2R45, OC(O)(alquil C1-6), alquil C1-6, hidroxialquil C1-6, haloalquil C1-6, alcoxi C1-6-alquil C1-6, amino(alquil C1-4), di(alquilamino C1-6)-alquiI C1-6, alcoxi C1-6, haloalcoxi C1-6, hidroxil(C1-6 alcoxi), heterociclil(C1-6 alcoxi), alcoxi C1-6-alcoxi C1-6, amino(alcoxi C1-4), alquilamino C1-4-alcoxi C1-4 (este opcionalmente sustituido por fenil), di(aIquil C1-4)amino-alcoxi C1-4, alquiltio C1-6,alquenil C2-6, alquinil C2-6, cicloalquil C3-10 (este opcionalmente sustituido por alquil C1-4 u oxo), metilenodioxi, difluorometilenodioxi, heterociclil, heterociclil(alquil C1-4), fenil, fenil(alquil C1-4, fenoxi, feniltio, fenil(alcoxi C1-4), heteroaril, heteroaril(alquil C1-4), heteroariloxi o heteroaril(alcoxi C1-4); donde cualquiera de las mitades fenil y heteroaril inmediatamente precedentes son opcionalmente sustituidas con halogeno, hidroxi, nitro, S(O)r(alquil C1-4), S(O)2NH2, S(O)2NH(alquil C1-4), S(O)2N(alquil C1-4)2, ciano, alquil C1-4, alcoxi C1-4, C(O)NH2, C(O)NH(alquil C1-4), C(O)N(alquil C1-4)2, CO2H, CO2(alquilC1-4), NHC(O)(alquil C1-4), NH(O)2(alquil C1-4), C(O)(alquil C1-4), CF3 u OCF3; q y r son, independientemente, 0, 1 o 2; a menos que se declare lo contrario el heterociclil es opcionalmente sustituido por OH, alquil C1-6, cicloalquil C3-7, NR46R47, (alquil C1-6)OH o (alquil C1-6)NR48R49, NR50CO2(alquil C1-6), CO2(alquil C1-6), C(O)(alquil C1-6), C(O)heterociclil, heteroaril, (alquil C1-6)C(O)NR51 R52, (alquil C1-6)C(O)NR53R54, (alquil C1-6)C(O)heterociclil o heterociclil; R26, R27, R28, R29, R30, R31, R32, R33, R34, R35, R36, R37, R38, R39, R40, R41, R42, R43, R44 y R45 son, independientemente, alquil C1-6 {opcionalmente sustituido por halogeno, hidroxi o alcoxi C1-6}, CH2(alquenil C2-6), fenil {este opcionalmente sustituido por halogeno, hidroxi, nitro, NH2, NH(alquil C1-4), N(alquil C1-4)2, S(O)2(alquil C1-4), S(O)2NH2, S(O)2NH(alquil C1-4), S(O)2N(alquil C1-4)2, ciano, alquil C1-4, alcoxi C1-4, C(O)NH2, C(O)NH(alquil C1-4), C(O)N(alquil C1-4)2, CO2H, CO2(alquil C1-4), NHC(O)(alquil C1-4), NH(O)2(alquil C1-4), C(O)(alquil C1-4), CF3 u OCF3} o heteroaril {este opcionalmente sustituido por halogeno, hidroxi, nitro, NH2, NH(alquil C1-4), N(alquil C1-4)2, S(O)2(alquil C1-4), S(O)2NH2, S(O)2NH(alquil C1-4), S(O)2N(alquil C1-4)2, ciano, alquil C1-4, alcoxi C1-4, C(O)NH2, C(O)NH(alquil C1-4), C(O)N(alquil C1-4)2, CO2H, CO2(alquil C1-4), NHC(O)(alquil C1-4), NH(O)2(alquil C1-4), C(O)(alquil C1-4), CF3 u OCF3}; R27, R28, R29, R30, R31, R32, R33, R34, R35, R36, R37, R38, R40, R41, R42, R43, R44 y R45 tambien pueden ser hidrogeno; R12, R14, R15, R25, R47 y R49 son, independientemente, hidrogeno, alquil C1-6 (opcionalmente sustituido por hidroxi, alcoxi C1-6, alquiltio C1-6, cicloalquil C3-7 (opcionalmente sustituido por hidroxi) o NR55R56), cicloalquil C3-7 (opcionalmente sustituido por hidroxi(alquil C1-6)) o heterociclil (opcionalmente sustituido por alquil C1-6); R11, R13, R16, R24, R26, R27, R46, R48, R50, R51, R52, R53, R54, R55 y R56 son, independientemente. hidrogeno o alquil C1-6; o un N-oxido de este; o una sal farmaceuticamente aceptable de este.
ARP090101896A 2008-05-27 2009-05-27 Compuestos derivados de piridina, proceso para su preparacion, una composicion farmaceutica que lo comprende , metodo para tratar un estado de enfermedad AR071920A1 (es)

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