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AR065081A1 - FUSIONATED QUINAZOLINONA AND PIRIMIDONA COMPOUNDS AND PHARMACEUTICAL COMPOSITION - Google Patents

FUSIONATED QUINAZOLINONA AND PIRIMIDONA COMPOUNDS AND PHARMACEUTICAL COMPOSITION

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Publication number
AR065081A1
AR065081A1 ARP080100362A ARP080100362A AR065081A1 AR 065081 A1 AR065081 A1 AR 065081A1 AR P080100362 A ARP080100362 A AR P080100362A AR P080100362 A ARP080100362 A AR P080100362A AR 065081 A1 AR065081 A1 AR 065081A1
Authority
AR
Argentina
Prior art keywords
optionally substituted
heterocyclyl
cycloalkylalkyl
heteroaryl
heteroarylalkyl
Prior art date
Application number
ARP080100362A
Other languages
Spanish (es)
Inventor
Qun Sun
Jianmin Fu
Duanjie Hou
Rajender Kamboj
Serguei Sviridov
Robert Fraser
Shifeng Liu
Original Assignee
Xenon Pharmaceuticals Inc
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Publication date
Application filed by Xenon Pharmaceuticals Inc filed Critical Xenon Pharmaceuticals Inc
Publication of AR065081A1 publication Critical patent/AR065081A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/88—Oxygen atoms
    • C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
    • 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
    • A61P23/00—Anaesthetics
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • 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
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • 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)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Cardiology (AREA)
  • Biomedical Technology (AREA)
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  • Heart & Thoracic Surgery (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Anesthesiology (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Estos compuestos, sus estereoisomeros, enantiomeros, tautomeros o sus mezclas; una de sus sales, solvatos o profármacos farmacéuticamente aceptables son utiles para el tratamiento y/o la prevencion de enfermedades o condiciones patologicas mediadas por el canal de sodio, tales como dolor. Reivindicacion 1: Un compuesto de la formula (1), caracterizado porque: n es 1 a 4; el anillo A es un arilo fusionado o un heteroarilo fusionado; cada R1 está seleccionado, de modo independiente, del grupo que consiste en hidrogeno, alquilo, alquenilo, alquinilo, halo, haloalquilo, haloalquenilo, haloalquinilo, cicloalquilo, cicloalquilalquilo, cicloalquilalquenilo, cicloalquilalquinilo, arilo, aralquilo, aralquenilo, aralquinilo, heterociclilo, heterocicliIalquilo, heterociclilalquenilo, heterociclilalquinilo, heteroarilo, heteroarilalquilo, heteroarilalquenilo, heteroarilalquinilo,-R6-CN, -R6-NO2, -R6-OR5, -R6-N(R4)R5, -R6-S(O)pR4, -R6-C(O)R4, -R6-C(S)R4, -R6-C(R4)2C(O)R5, -R6-C(O)OR4, - R6-OC(O)R4, -R6-C(S)OR4, -R6-C(O)N(R4)R5, -R-C(S)N(R4)R5, -R6-N(R5)C(O)R4, -R6-N(R5)C(S)R4, -R6-N(R5)C(O)OR4, -R6-N(R5)C(S)OR4, -R6-N(R5)C(O)N(R4)R5, -R6-N(R5)C(S)N(R4)R5, -R6-N(R5)S(O)tR4, -R6-N(R5)S(O)tN(R4)R5, -R6-S(O)tN(R4)R5, -R6- N(R5)C(=NR5)N(R4)R5, y -R6-N(R5)C(N=C(R4)R5)N(R4)R5, en donde cada p es, de modo independiente, 0, 1 o 2 y cada t es, de modo independiente, 1 o 2, o dos grupos adyacentes R1, junto con los átomos de carbono o heteroanillos a los que están directamente unidos, pueden formar un anillo fusionado seleccionado de cicloalquilo, arilo, heterociclilo o heteroarilo, y los grupos R1 restantes, de estar presentes son como se describieron con anterioridad; R2 es hidrogeno, alquilo, alquenilo, alquinilo, haloalquilo, haloalquenilo, haloalquinilo, cicloalquilo, cicloalquilalquilo, cicloalquilalquenilo, arilo, aralquilo, aralquenilo, aralquinilo, heterociclilo, heterociclilalquilo, heterociclilalquenilo, heterociclilalquinilo, heteroarilo, heteroarilalquilo, heteroarilalquenilo o heteroarilalquinilo; R3 es hidrogeno, alquilo, alquenilo, alquinilo, haloalquilo, haloalquenilo, haloalquinilo, hidroxialquilo, cicloalquilo, cicloalquilalquilo, cicloalquilalquenilo, cicloalquilalquinilo, arilo, aralquilo, aralquenilo, aralquinilo, heterociclilo, heterociclilalquilo, heterociclilalquenilo, heterociclilalquinilo, heteroarilo, heteroarilalquilo, heteroarilalquenilo, heteroarilalquinilo, -R7-N(R4)R5 o -R7-N(R4)C(O)OR4; en donde el grupo cicloalquilo, cicloalquilalquilo, cicloalquilalquenilo, cicloalquilalquinilo, arilo, aralquilo, aralquenilo, aralquinilo, heterociclilo, heterociclilalquilo, heterociclilalquenilo, heterociclilalquinilo, heteroarilo, heteroarilalquilo, heteroarilalquenilo o heteroarilalquinilo puede estar opcionalmente sustituido con uno o varios sustituyentes seleccionados del grupo que consiste en alquilo, alquenilo, alquenilo, alquinilo, halo, haloalquilo, haloalquenilo, haloalquinilo, cicloalquilo opcionalmente sustituido, cicloalquilalquilo opcionalmente sustituido, cicloalquilalquenilo opcionalmente sustituido, cicloalquilalquinilo opcionalmente sustituido, arilo opcionalmente sustituido, aralquilo opcionalmente sustituido, aralquenilo opcionalmente sustituido, aralquinilo opcionalmente sustituido, heterociclilo opcionalmente sustituido, heterociclilalquilo opcionalmente sustituido, heterociclilalquenilo opcionalmente sustituido, heterociclilalquinilo opcionalmente sustituido, heteroarilo opcionalmente sustituido, heteroarilalquilo opcionalmente sustituido, heteroarilalquenilo opcionalmente sustituido, heteroarilalquinilo opcionalmente sustituido, R6-CN, -R6-NO2, -R6-OR5, -R6-OC(O)R4, -R6-OS(O)2R4, -R6-C(O)R4, -R6-C(O)OR4, -R6-C(O)N(R4)R5, -R6-N(R4)R5, -R6-N(R5)C(O)R4, -R6-N(R5)C(O)OR4, -R6-N(R5)C(O)N(R4)R5, -R6-N(R5)S(O)tR4, -R6-N[S(O)tR4]2, -R6-N(R5)C(=NR5)N(R4)R5, -R6-N(R5)C(=NR5)N(R4)CN, -R6-N(R5)C[=NC(O)OR4]-N(R4)-C(O)OR4, -R6-N(R5)-R7-N(R4)R5, -R6- N=C(OR4)R5, -R6-N=C(R4)R5, -R6-N(R5)-, -R6-OR5, -R6-S(O)pR4, y -R6-S(O)tN(R4)R5, en donde cada p es, de modo independiente, 0, 1 o 2 y cada t es, de modo independiente, 1 o 2, cada R4 y R5 está seleccionado, de modo independiente, del grupo que consiste en hidrogeno, alquilo, alquenilo, alquinilo, haloalquilo, hidroxialquilo, alcoxialquilo, cicloalquilo opcionalmente sustituido, cicloalquilalquilo opcionalmente sustituido, arilo opcionalmente sustituido, aralquilo opcionalmente sustituido, heterociclilo opcionalmente sustituido, heterociclilalquilo opcionalmente sustituido, heteroarilo opcionalmente sustituido y heteroarilalquilo opcionalmente sustituido; o R4 y R5, junto con el nitrogeno al que están unidos ambos, forman un N- heterociclilo opcionalmente sustituido o un N-heteroarilo opcionalmente suslituido; cada R6 es un enlace directo, una cadena de alquileno lineal o ramificada opcionalmente sustituida, una cadena de alquenileno lineal o ramificada opcionalmente sustituida o una cadena de alquinileno lineal o ramificada opcionalmente sustituida; y R7 es una cadena de alquileno lineal o ramificada, una cadena de alquenileno lineal o ramificada o una cadena de alquinileno lineal o ramificada; corno uno de sus estereoisomeros, enantiomeros, tautomeros o sus mezclas: o una de sus sales, solvatos o profármacos farmacéuticamente aceptables.These compounds, their stereoisomers, enantiomers, tautomers or mixtures thereof; one of its pharmaceutically acceptable salts, solvates or prodrugs are useful for the treatment and / or prevention of diseases or pathological conditions mediated by the sodium channel, such as pain. Claim 1: A compound of the formula (1), characterized in that: n is 1 to 4; ring A is a fused aryl or a fused heteroaryl; each R1 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, halo, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkyl, cycloalkylalkyl, aryl, aralkyl, aralkenyl, aralkynyl, heterocyclyl, heterocyclyl, heterocyclyl, heterocyclyl, heterocyclyl, heterocyclyl heterocyclylalkenyl, heterocyclylalkyl, heteroaryl, heteroarylalkyl, heteroarylalkyl, heteroarylalkyl, -R6-CN, -R6-NO2, -R6-OR5, -R6-N (R4) R5, -R6-S (O) pR4, -R6-C ( O) R4, -R6-C (S) R4, -R6-C (R4) 2C (O) R5, -R6-C (O) OR4, - R6-OC (O) R4, -R6-C (S ) OR4, -R6-C (O) N (R4) R5, -RC (S) N (R4) R5, -R6-N (R5) C (O) R4, -R6-N (R5) C (S ) R4, -R6-N (R5) C (O) OR4, -R6-N (R5) C (S) OR4, -R6-N (R5) C (O) N (R4) R5, -R6-N (R5) C (S) N (R4) R5, -R6-N (R5) S (O) tR4, -R6-N (R5) S (O) tN (R4) R5, -R6-S (O) tN (R4) R5, -R6- N (R5) C (= NR5) N (R4) R5, and -R6-N (R5) C (N = C (R4) R5) N (R4) R5, where each p is, independently, 0, 1 or 2 and each t is, independently, 1 or 2, or two adjacent groups R1, together with the carbon atoms or heteroanillos to which they are directly attached, can form a fused ring selected from cycloalkyl, aryl, heterocyclyl or heteroaryl, and the remaining R1 groups, if present are as described above; R2 is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, aryl, aralkyl, aralkenyl, aralkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl or heteroarylalkynyl; R3 is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, aryl, aralkyl, aralkenyl, aralkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, -R7-N (R4) R5 or -R7-N (R4) C (O) OR4; wherein the cycloalkyl, cycloalkylalkyl, cycloalkylalkyl, cycloalkylalkyl, aryl, aralkyl, aralkenyl, aralkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkyl, heteroarylalkyl or heteroaryl group may be substituted by one or several of which may be selected from one heteroaryl or alkyl group alkyl, alkenyl, alkenyl, alkynyl, halo, haloalkyl, haloalkenyl, haloalkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted cycloalkylalkenyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkyl, optionally substituted heterocyclyl substituted, optionally substituted heterocyclylalkyl, optionally substituted heterocyclylalkenyl, optionally substituted heterocyclylalkyl, h optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted heteroarylalkyl, optionally substituted heteroarylalkyl, R6-CN, -R6-NO2, -R6-OR5, -R6-OC (O) R4, -R6-OS (O) 2R4, -R6 -C (O) R4, -R6-C (O) OR4, -R6-C (O) N (R4) R5, -R6-N (R4) R5, -R6-N (R5) C (O) R4 , -R6-N (R5) C (O) OR4, -R6-N (R5) C (O) N (R4) R5, -R6-N (R5) S (O) tR4, -R6-N [S (O) tR4] 2, -R6-N (R5) C (= NR5) N (R4) R5, -R6-N (R5) C (= NR5) N (R4) CN, -R6-N (R5) C [= NC (O) OR4] -N (R4) -C (O) OR4, -R6-N (R5) -R7-N (R4) R5, -R6- N = C (OR4) R5, -R6 -N = C (R4) R5, -R6-N (R5) -, -R6-OR5, -R6-S (O) pR4, and -R6-S (O) tN (R4) R5, where each p it is, independently, 0, 1 or 2 and each t is, independently, 1 or 2, each R4 and R5 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aryl, optionally substituted aralkyl, heterocyclyl opci optionally substituted, optionally substituted heterocyclyl alkyl, optionally substituted heteroaryl and optionally substituted heteroarylalkyl; or R4 and R5, together with the nitrogen to which both are attached, form an optionally substituted N-heterocyclyl or an optionally substituted N-heteroaryl; each R6 is a direct bond, an optionally substituted linear or branched alkylene chain, an optionally substituted linear or branched alkenylene chain or an optionally substituted linear or branched alkynylene chain; and R7 is a linear or branched alkylene chain, a linear or branched alkenylene chain or a linear or branched alkynylene chain; as one of its stereoisomers, enantiomers, tautomers or mixtures thereof: or one of its pharmaceutically acceptable salts, solvates or prodrugs.

ARP080100362A 2007-01-29 2008-01-29 FUSIONATED QUINAZOLINONA AND PIRIMIDONA COMPOUNDS AND PHARMACEUTICAL COMPOSITION AR065081A1 (en)

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