AR073740A1 - Compuestos para el tratamiento de la hepatitis c - Google Patents

Compuestos para el tratamiento de la hepatitis c

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Publication number
AR073740A1
AR073740A1 ARP090103514A ARP090103514A AR073740A1 AR 073740 A1 AR073740 A1 AR 073740A1 AR P090103514 A ARP090103514 A AR P090103514A AR P090103514 A ARP090103514 A AR P090103514A AR 073740 A1 AR073740 A1 AR 073740A1
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AR
Argentina
Prior art keywords
alkyl
hydroxyalkyl
amino
phenyl
hydrogen
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ARP090103514A
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English (en)
Inventor
Ying Han
John F Kadow
John A Bender
Kap-Sun Yeung
Piyasena Hewawasam
Kyle E Parcella
Katharine A Grant-Young
Brett R Beno
Andrew Nickel
Original Assignee
Bristol Myers Squibb Co
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Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co
Publication of AR073740A1 publication Critical patent/AR073740A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
    • C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • 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
    • 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
    • C07D405/10—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 linked by a carbon chain containing aromatic 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
    • C07D405/02—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
    • C07D405/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
    • C07D413/02—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
    • C07D413/10—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 carbon chain containing aromatic 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
    • 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
    • C07D417/10—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 carbon chain containing aromatic 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
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—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
    • 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
    • C07D491/10—Spiro-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Virology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oncology (AREA)
  • Public Health (AREA)
  • Molecular Biology (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Furan Compounds (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Reivindicacion 1: Un compuesto caracterizado por tener la formula 1: R1 es R5R6N; alcoxi; (alcoxicarbonilamino)alcoxi; (alquilfenil)alcoxi; (carboxi)alquenilo; (alcoxicarbonil)alquenilo; (benciloxicarbonil)alquenilo; ((N-dimetilbencil)aminocarbonil)alquenilo; o fenilo donde dicho fenilo está sustituido con 1-2 sustituyentes que se seleccionan a partir del grupo constituido por halo, ciano, alquilo, haloalquilo, hidroxialquilo, alcoxialquilo, (carboxi)alquilo, alcoxi, hidroxialquiloxi, alcoxialquiloxi, benciloxi, tetrahidropiraniloxi, carboxi, alcoxicarbonilo, alquilsulfonilo, (carboxi)alquenilo, (alcoxicarbonil)alquenilo, alquilcarboxamido, alcoxicarboxamido, alquilsulfamido, (alquilsulfamido)alquilo, Ar5, SO2NR15R16, y CONR7R8: y donde dicho fenilo también está sustituido con 0-2 sustituyentes que se seleccionan a partir del grupo constituido por halo; nitro; alquilo; cicloalquilo; haloalquilo; aminoalquilo; hidroxialquilo; alcoxialquilo; hidroxi; alcoxi; OR17 cicloalcoxi; amino; alquilamino; dialquilamino; alquilcarboxamido; alcoxicarboxamido; alcoxialquilcarboxamido; furanilo, tienilo, o pirazolilo sustituido con 0-2 sustituyentes alquilo; piridinilo sustituido con 0-2 sustituyentes halo, ciano, alquilo, hidroxi, alcoxi, amino, o alquilaminocarbonilo; pirimidinilo; pirimidindionilo; aminopirimidinilo; indolilo; isoquinolinilo; y fenilo sustituido con 0-2 sustituyentes que se seleccionan a partir del grupo constituido por halo, alquilo, cianoalquilo, hidroxialquilo, alcoxialquilo, hidroxi, alcoxi, amino, carboxi, alcoxicarbonilo, aminocarbonilo, alquilaminocarbonilo, dialquilaminocarbonilo, alquilcarboxamido, carboxialquenilo, y fenilo; R2 es hidrogeno, halo, nitro, amino, fenilo, o R5R6N; R3 es ciano, alcoxicarbonilo, (cicloalquil)oxicarbonilo, (alquilsulfonil)aminocarbonilo, CONR11R12, (R11)(R12)NCONH, triazolilo, tiazolilo, o tetrazolilo; R4 es fenilo sustituido con 0-2 sustituyentes halo; R5 es hidrogeno, alquilo, o alquilsulfonilo; R6 es hidrogeno, alquilo, hidroxialquilo, alcoxialquilo, o alquilsulfonilo; R7 es hidrogeno, alquilo, alquenilo, alquinilo, cianoalquilo, haloalquilo, hidroxialquilo, dihidroxialquilo, alcoxialquilo, oxoalquilo, aminoalquilo, (alquilamino)alquilo, (dialquilamino)alquilo, (cicloalquil)alquilo, cicloalquilo, (alquil)cicloalquilo, (hidroxialquil)cicloalquilo, (tetrahidrofuranil)alquilo, (tetrahidropiranil)alquilo, (carboxi)alquilo, (alcoxicarbonil)alquilo, (alqueniloxicarbonil)alquilo, (alcoxicarbonil)hidroxialquilo, (CONR13R14)alquilo, (CONR1314)(hidroxialquil)alquilo, (CONR13R14)cicloalquilo, (alquilcarbonil)aminoalquilo, (fenil)alquilo, (piridinil)alquilo, alquilsulfonilo, fenilsulfonilo, Ar2, Ar3, y el grupo de formulas 2; R8 es hidrogeno, alquilo, hidroxialquilo, o alcoxialquilo; o R7R8N tomado conjuntamente es azetidinilo, pirrolidinilo, piperidinilo, piperazinilo, morfolinilo, dihidroindolilo, o isoindolinilo, y está sustituido con 0-2 sustituyentes que se seleccionan a partir de alquilo, hidroxialquilo, alcoxialquilo, hidroxi, alcoxi, carboxi, alcoxicarbonilo, dialquilcarboxamido, alquilcarbonilamino, alcoxicarbonilamino, piridinilo, y fenilo donde dicho fenilo está sustituido con 0-2 sustituyentes halo o alquilo; o donde R7R8N tomado conjuntamente es, la formula 3, (quinuclidinil)amino, (quinuclidinil)(alquil)amino, (metilpirrolidinil)(alquil)amino, ((imidazolil)alquil)(hidroxialquil)amino, (alquiltiazolil)amino, ((carboxamido)ciclopentanil)amino, ((halofenil)ciclopentanil)amino, 3H-espiro(isobenzofuranil)piperidinilo, (hidroxiindanil)amino, o la formula 4;R9 es hidrogeno, alquilo, hidroxialquilo, o alcoxialquilo; R10 es hidrogeno, alquilo, hidroxialquilo, o alcoxialquilo; o y R10 tomados conjuntamente son etileno, propileno, butileno, pentileno, o hexileno; R11 es hidrogeno, alquilo, o cicloalquilo; R12 es hidrogeno, alquilo, o cicloalquilo; o R11 y R12 tomados conjuntamente con el nitrogeno al que están unidos son azetidinilo, pirrolidinilo, piperidinilo, piperazinilo, o morfolinilo; R13 es hidrogeno, alquilo, cianoalquilo, haloalquilo, alquenilo, alquinilo, o tiazolilo; R14 es hidrogeno o alquilo; R15 es hidrogeno, alquilo, hidroxialquilo, cicloalquilo, o bencilo; R16 es hidrogeno o alquilo; o R15 y R16 tomados conjuntamente con el nitrogeno al que están unidos son azetidinilo, pirrolidinilo, piperidinilo, piperazinilo, o morfolinilo; R17 es haloalquilo, cianoalquilo, (cicloalquil)alquilo, hidroxialquilo, alcoxialquilo, aminoalquilo, (R18)alquilo, (Ar4)alquilo, alquinilo, o aminocicloalquilo; R18 es CONH2, H2NCONH, dibencilamino, ftalimido, amino, alquilamino, dialquilamino, azetidinilo, pirrolidinilo, piperidinilo, piperazinilo, o morfolinilo donde azetidinilo, pirrolidinilo, piperidinilo, piperazinilo, o morfolinilo están sustituidos con 0-3 sustituyentes alquilo o alcoxicarbonilo; R19 es ciano, hidroxialquilo, morfolinilalquilo, carboxi, alcoxicarbonilo, cicloalquilsulfoxamido, ((alquil)pirazolil)amino, ((alquil)isoxazolil)amino, (tiadiazolil)amino, (triazinil)amino, o alquinilaminocarbonilo; R20 es hidrogeno, halo, alquilo, o alcoxi; R21 es hidrogeno, halo, alquilo, o alcoxi; Ar1 es fenilo, naftalenilo, piridinilo, furanilo, tienilo, pirrolilo, pirazolilo, isoxazolilo, isotiazolilo, imidazolilo, oxazolilo, tiazolilo, oxadiazolilo, oxadiatiazolilo, triazolilo, tetrazolilo, pirazinilo, pirimidinilo, o benzotiazolilo, y está sustituido con 0-2 sustituyentes que se seleccionan a partir de halo, alquilo, cicloalquilo, haloalquilo, alcoxialquilo, hidroxi, alcoxi, amino, alquilamino, dialquilamino, aminocarbonilo, piridinilo, fenilo, halofenilo, alquilfenilo, y alcoxifenilo; Ar2 es fenilo. bifenilo, o piridinilo, y está sustituido con 0-2 sustituyentes que se seleccionan a partir de halo, alquilo, ciano, hidroxi, alcoxi, y carboxi; Ar3 es pirazolilo, isoxazolilo, isotiazolilo, imidazolilo, oxazolilo, tiazolilo, triazolilo, oxadiazolilo, oxatiadiazolilo, pirimidinilo, o pirizinilo, y está sustituido con 0-2 sustituyentes que se seleccionan a partir de hidroxi, alquilo, hidroxialquilo, y CONR13R14; Ar4 es furanilo, tienilo, pirrolilo, pirazolilo, isoxazolilo, isotiazolilo, imidazolilo, oxadiazolilo, tiadiazolilo, triazolilo, piridinilo, indolilo, o fenilo, y está sustituido con 0-2 sustituyentes que se seleccionan a partir de halo, alquilo, haloalquilo, hidroxilo, y alcoxi; y Ar5 es pirrozolilo, imidazolilo, u oxadiazolilo, y está sustituido con 0-2 sustituyentes que se seleccionan a partir de alquilo, carboxi, alcoxicarbonilo, bencilo, y fenilo; o una sal farmacéuticamente aceptable del mismo.
ARP090103514A 2008-09-11 2009-09-11 Compuestos para el tratamiento de la hepatitis c AR073740A1 (es)

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US (1) US8048887B2 (es)
EP (1) EP2326633B1 (es)
JP (1) JP5685191B2 (es)
KR (1) KR20110059875A (es)
CN (1) CN102209717B (es)
AR (1) AR073740A1 (es)
AU (1) AU2009291966B2 (es)
BR (1) BRPI0918174A2 (es)
CA (1) CA2736988A1 (es)
CL (2) CL2011000527A1 (es)
CO (1) CO6382110A2 (es)
EA (1) EA019185B1 (es)
IL (1) IL211509A0 (es)
MX (1) MX2011002410A (es)
NZ (1) NZ591172A (es)
PE (1) PE20110806A1 (es)
TW (2) TW201124403A (es)
WO (1) WO2010030592A1 (es)
ZA (2) ZA201101739B (es)

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