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HRP20130063T1 - Inhibitori virusa hepatitisa c - Google Patents

Inhibitori virusa hepatitisa c Download PDF

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Publication number
HRP20130063T1
HRP20130063T1 HRP20130063AT HRP20130063T HRP20130063T1 HR P20130063 T1 HRP20130063 T1 HR P20130063T1 HR P20130063A T HRP20130063A T HR P20130063AT HR P20130063 T HRP20130063 T HR P20130063T HR P20130063 T1 HRP20130063 T1 HR P20130063T1
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Croatia
Prior art keywords
pyrrolidinyl
methyl
benzimidazol
imidazol
methoxycarbonyl
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HRP20130063AT
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English (en)
Inventor
Jeffrey Lee Romine
Denis R. St. Laurent
Makonen Belema
Lawrence B. Snyder
Lawrence G. Hamann
John F. Kadow
Jayne Kapur
Andrew C. Good
Omar D. Lopez
Rico Lavoie
John A. Bender
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Bristol-Myers Squibb Company
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Publication of HRP20130063T1 publication Critical patent/HRP20130063T1/hr

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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
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    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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    • A61K38/20—Interleukins [IL]
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    • A61K38/19—Cytokines; Lymphokines; Interferons
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    • A61K38/21—Interferons [IFN]
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    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
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    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
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    • 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
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    • 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
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    • 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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  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Claims (27)

1. Spoj Formule (I) [image] ili njegova farmaceutski prihvatljiva sol, gdje svaki m je nezavisno 0 ili 1; svaki n je nezavisno 0 ili 1; L je veza ili se izabire između [image] i [image] gdje je svaka skupina prikazana s lijevim krajem spojenim za benzimidazol i desnim krajem spojenim s R1; R1 se izabire između [image] svaki R2 je nezavisno izabran između alkila i halogena; svaki R3 je nezavisno izabran između vodika i -C(O)R7; R4 je alkil; R5 i R6 su nezavisno izabrani između vodika, alkila, cijanoalkila, i halogena, ili R5 i R6, zajedno s atomom ugljika s kojim su spojeni, formiraju šesteročlani ili sedmeročlani prsten koji po izboru sadrži jedan heteroatom izabran između dušika i kisika i po izboru sadrži dodatnu dvostruku vezu; i svaki R7 je nezavisno izabran između alkoksi, alkil, arilalkoksi, arilalkil, cikloalkil, (cikloalkil)alkil, heterociklil, heterociklilalkil, (NRcRd)alkenil, i (NRcRd)alkil.
2. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, gdje L je veza.
3. Spoj prema zahtjevu 2, ili njegova farmaceutski prihvatljiva sol, gdje je R1 [image]
4. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, gdje je L [image]
5. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, gdje je L [image]
6. Spoj prema zahtjevu 5, ili njegova farmaceutski prihvatljiva sol, gdje se R1 izabire između [image] i [image]
7. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, gdje je L [image]
8. Spoj prema zahtjevu 7, ili njegova farmaceutski prihvatljiva sol, gdje se L izabire između [image] i [image]
9. Spoj prema zahtjevu 8, ili njegova farmaceutski prihvatljiva sol, gdje je R1 [image]
10. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, gdje je L [image]
11. Spoj prema zahtjevu 10, ili njegova farmaceutski prihvatljiva sol, gdje je R1 [image]
12. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, gdje se L izabire između [image] i [image] gdje je svaka skupina prikazana s lijevim krajem spojenim za benzimidazol i desnim krajem spojenim s R1.
13. Spoj prema zahtjevu 12, ili njegova farmaceutski prihvatljiva sol, gdje je R1 [image]
14. Spoj Formule (II) [image] ili njegova farmaceutski prihvatljiva sol, gdje svaki m je nezavisno 0 ili 1; svaki n je nezavisno 0 ili 1; L je veza ili se izabire između [image] i [image] R1 se izabire između [image] i [image] svaki R2 je nezavisno izabran između alkila i halogena; svaki R3 je nezavisno izabran između vodika i -C(O)R7; R4 je alkil; R5 i R6 su nezavisno vodik ili halogen, ili R5 i R6, zajedno s atomom ugljika s kojim su spojeni, formiraju šesteročlani ili sedmeročlani prsten koji po izboru sadrži jedan heteroatom izabran između dušika i kisika i po izboru sadrži dodatnu dvostruku vezu; i svaki R7 je nezavisno izabran između alkoksi, alkil, arilalkil, cikloalkil, heterociklil, heterociklilalkil, (NRcRd) alkenil, i (NRcRd)alkil.
15. Spoj izabran između metil ((1S)-1-(((2S)-2-(8-(4-(2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1Himidazol-4-il)fenil)-1,4,5,6-tetrahidrobenzo[3,4]ciklohepta[1,2-d]imidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; (1R)-2-((2S)-2-(8-(2-((2S)-1-((2R)-2-(dietilamino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)-1,4,5,6-tetrahidrobenzo[3,4]ciklohepta[1,2-d]imidazol-2-il)-1-pirolidinil)-N,N-dietil-2-okso-1-feniletanamin; metil ((1S)-1-(((2S)-2-(5-(4-(2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1Himidazol-4-il)fenil)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; (1R)-2-((2S)-2-(4-(4-(2-((2S)-1-((2R)-2-(dietilamino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)fenil)-1H-imidazol-2-il)-1-pirolidinil)-N,N-dietil-2-okso-I-feniletanamin; metil ((1R)-2-((2S)-2-(4-(4-(2-((2S)-1-((2R)-2-((metoksikarbonil)amino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)fenil)-1H-imidazol-2-il)-1-pirolidinil)-2-okso-1-feniletil)karbamat; metil ((1S)-1-(((2S)-2-(5-(3-(2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1Himidazol-4-il)fenil)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; (1R)-2-((2S)-2-(4-(3-(2-((2S)-1-((2R)-2-(dietilamino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)fenil)-1H-imidazol-2-il)-1-pirolidinil)-N,N-dietil-2-okso-1-feniletanamin; metil ((1R)-2-((2S)-2-(4-(3-(2-((2S)-1-((2R)-2-((metoksikarbonil)amino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)fenil)-1H-imidazol-2-il)-1-pirolidinil)-2-okso-1-feniletil)karbamat; metil ((1S)-1-(((1R,3S,5R)-3-(8-(2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]hex-3-il)-1H-benzimidazol-5-il)-1,4,5,6-tetrahidrobenzo[3,4]ciklohepta[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((2S)-2-(5-(2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-4,5-dihidro-3H-nafto[1,2-d]imidazol-7-il)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((2S)-2-(5-(4’-(2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1Himidazol-4-il)-4-bifenilil)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((2S)-2-(5-(2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-3Hnafto[1,2-d]imidazol-7-il)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; (1R)-2-((2R)-2-(7-(2-((2S)-1-((2R)-2-(dietilamino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)-1Hnafto[1,2-d]imidazol-2-il)-1-pirolidinil)-N,N-dietil-2-okso-1-feniletanamin; metil ((1S)-1-(((2S)-2-(5-(4-(2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1Hnafto[1,2-d]imidazol-7-il)fenil)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; metil ((1R)-2-((2S)-2-(7-(4-(2-((2S)-1-((2R)-2-((metoksikarbonil)amino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)fenil)-1H-nafto[1,2-d]imidazol-2-il)-1-pirolidinil)-2-okso-1-feniletil)karbamat; metil ((1S)-1-(((2S)-2-(5-((4-(2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1Himidazol-4-il)fenil)ethynil)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; (1R)-2-((2S)-2-(4-(4-((2-((2S)-1-((2R)-2-(dietilamino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)etinil)fenil)-1H-imidazol-2-il)-1-pirolidinil)-N,N-dietil-2-okso-1-feniletanamin; metil ((1S)-1-(((2S)-2-(5-((4-(4-etil-2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1H-imidazol-5-il)fenil)etinil)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((2S)-2-(4-(cijanometil)-5-(4-((2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1H-benzimidazol-5-il)etinil)fenil)-1H-imidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((1R,3S,5R)-3-(5-((4-(2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-imidazol-4-il)fenil)etinil)-1H-benzimidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((1R,3S,5R)-3-(4-(4-((4-fluoro-2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)- H-benzimidazol-6-il)etinil)fenil)-1H-imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((1R,3S,5R)-3-(4-(2-fluoro-4-((2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etinil)fenil)-1H-imidazol-2-il)-2-azabiciklo [3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((2S)-2-(5-((2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-4,5-dihidro-3H-nafto[1,2-d]imidazol-7-il)etinil)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; metil ((1R)-2-((2S)-2-(7-((2-((2S)-1-((2R)-2-((metoksikarbonil)amino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)etinil)-4,5-dihidro-1H-nafto[1,2-d]imidazol-2-il)-1-pirolidinil)-2-okso-1-feniletil)karbamat; metil ((1S)-1-(((2S)-2-(5-((2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-3Hnafto[1,2-d]imidazol-7-il)etinil)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; metil ((1R)-2-((2S)-2-(7-((2-((2S)-1-((2R)-2-((metoksikarbonil)amino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)etinil)- 1H-nafto[ 1,2-d] imidazol-2-il)-1-pirolidinil)-2-okso-1-feniletil)karbamat; metil ((1S)-1-(((2S)-2-(4-fluoro-6-((2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-4,5-dihidro-1H-nafto[1,2-d]imidazol-7-il)etinil)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((2S)-2-(4-fluoro-6-((2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1H-nafto[1,2-d]imidazol-7-il)etinil)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((1R,3S,5R)-3-(5-((2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-4,5-dihidro-1 1H-nafto[1,2-d]imidazol-7-il)etinil)-1H-benzimidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; metil ((1R)-2-((1R,3S,5R)-3-(7-((2-((1R,3S,5R)-2-((2R)-2-((metoksikarbonil)amino)-2-fenilacetil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etinil)-4,5-dihidro-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)-2-okso-1-feniletil)karbamat; metil ((1S)-1-(((1R,3S,5R)-3-(5-((2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-nafto[1,2-d]imidazol-7-il)etinil)-1H-benzimidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; metil ((1R)-2-((1R,3S,5R)-3-(7-((2-((1R,3S,5R)-2-((2R)-2-((metoksikarbonil)amino)-2-fenilacetil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etinil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)-2-okso-1-feniletil)karbamat; metil ((1S)-1-(4,4-difluorocikloheksil)-2-((1R,3S,5R)-3-(7-((2-((1R,3S,5R)-2-((2S)-2-(4,4-difluorocikloheksil)-2-((metoksikarbonil)amino)acetil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etinil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)-2-oksoetil)karbamat; metil ((1S)-2-((1R,3S,5R)-3-(7-((2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-2-(tetrahidro-2H-piran-4-il)acetil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etinil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)-2-okso-1-(tetrahidro-2H-piran-4-il)etil)karbamat; metil ((1S)-2-((1R,3S,5R)-3-(7-((2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etinil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)-2-okso-1-(tetrahidro-2H-piran-4-il)etil)karbamat; metil ((1S)-1-(((1R,3S,5R)-3-(4-fluoro-6-((2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-4,5-dihidro-1H-nafto [1,2-d]imidazol-7-il)etinil)-1H-benzimidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((1R,3S,5R)-3-(4-fluoro-6-((2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-nafto[1,2-d]imidazol-7-il)etinil)-1H-benzimidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; benzil (1R,3S,55R)-3-(7-((2-((1R,3S,5R)-2-(N-(metoksikarbonil)-L-valil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etinil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heksane-2-karboksilat; metil ((1S)-1-(((2S)-2-(5-(3-((2-((2S)-1-((2R)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1Hbenzimidazol-5-il)etinil)fenil)-1H-imidazol-4-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; (1R)-2-((2S)-2-(5-(3-((2-((2S)-1-((2R)-2-(dietilamino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)etinil)fenil)-1H-imidazol-4-il)-1-pirolidinil)-N,N-dietil-2-okso- 1-feniletanamin; metil ((1S)-1-(((2S)-2-(5-((4-(4-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1Himidazol-5-il)fenil)etinil)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((2S,5S)-2-(5-((2-((2S,5S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-5-metil-2-pirolidinil)-1H-nafto[1,2-d]imidazol-7-il)etinil)-1H-benzimidazol-2-il)-5-metil-1-pirolidinil)karbonil)-2-metilpropil)karbamat; metil ((1S)-2-((2S,5S)-2-(7-((2-((2S,5S)-1-((2S)-2-((metoksikarbonil)amino)-2-(tetrahidro-2H-piran-4-il)acetil)-5-metil-2-pirolidinil)-1H-benzimidazol-5-il)etinil)-1H-nafto[1,2-d]imidazol-2-il)-5-metil-1-pirolidinil)-2-okso-1-(tetrahidro-2H-piran-4-il)etil)karbamat; metil ((1S)-1-(((1R,3S,5R)-3-(7-(2-(2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; metil ((1S)-2-((1R,3S,5R)-3-(7-(2-(2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)-2-okso-1-(tetrahidro-2H-piran-4-il)etil)karbamat; (S)-1-acetil-N-(4-((2-((S)-1-(2-fenilacetil)pirolidin-2-il)-1H-benzo[d]imidazol-6-il)etinil)fenil)pirolidin-2-karboksamid; (S)-1-(2-fenilacetil)-N-(4-((2-((S)-1-(2-fenilacetil)pirolidin-2-il)-1H-benzo[d]imidazol-6-il)etinil)fenil)pirolidin-2-karboksamid; (S)-1-acetil-N-(4-(2-(2-((S)-1-(2-fenilacetil)pirolidin-2-il)-1H-benzo[d]imidazol-6-il)etil)fenil)pirolidin-2-karboksamid; (S)-1-(2-fenilacetil)-N-(4-(2-(2-((S)-1-(2-fenilacetil)pirolidin-2-il)-1H-benzo[d]imidazol-6-il)etil)fenil)pirolidin-2-karboksamid; metil ((1R)-2-((2S)-2-((5-(2-(2-((2S)-1-((2R)-2-((metoksikarbonil)amino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)-1,3-oxazol-5-il)-2-metilfenil)karbamoil)-1-pirolidinil)-2-okso-1-feniletil)karbamat; metil (R)-2-((S)-2-(S-(2-(2-((S)-1-((R)-2-(dimetilamino)-2-fenilacetil)pirolidin-2-il)-1H-benzo[d]imidazol-5-il)oxazol-5-il)-2-metilfenilkarbamoil)pirolidin-1-il)-2-okso-1-feniletilkarbamat; metil ((1R)-2-((2S)-2-((3-(2-(2-((2S)-1-((2R)-2-((metoksikarbonil)amino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)-1,3-oksazol-5-il)fenil)karbamoil)-1-pirolidinil)-2-okso-1-feniletil)karbamat; metil ((1R)-2-((1R,3S,5R)-3-(7-((2-((1R,3S,5R)-2-((2R)-2-((metoksikarbonil)amino)-2-fenilacetil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etinil)-4,5-dihidro-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)-2-okso-1-feniletil)karbamat; metil ((1S)-1-(((1R,3S,5R)-3-(5-((2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-nafto[1,2-d]imidazol-7-il)etinil)-1H-benzimidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; metil ((1R)-2-((1R,3S,5R)-3-(7-((2-((1R,3S,5R)-2-((2R)-2-((metoksikarbonil)amino)-2-fenilacetil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etinil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)-2-okso-1-feniletil)karbamat; metil ((1S)-1-(4,4-difluorocikloheksil)-2-((1R,3S,5R)-3-(7-((2-((1R,3S,5R)-2-((2S)-2-(4,4-difluorocikloheksil)-2-((metoksikarbonil)amino)acetil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etinil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)-2-oksoetil)karbamat; metil ((1S)-2-((1R,3S,5R)-3-(7-((2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-2-(tetrahidro-2H-piran-4-il)acetil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etinil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)-2-okso-1-(tetrahidro-2H-piran-4-il)etil)karbamat; metil ((1S)-2-((1R,3S,5R)-3-(7-((2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etinil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)-2-okso-1-(tetrahidro-2H-piran-4-il)etil)karbamat; metil ((1S)-1-(((1R,3S,5R)-3-(4-fluoro-6-((2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-4,5-dihidro-1H-nafto [1,2-d]imidazol-7-il)etinil)-1H-benzimidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((1R,3S,5R)-3-(4-fluoro-6-((2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-nafto[1,2-d]imidazol-7-il)etinil)-1H-benzimidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; benzil (1R,3S,55R)-3-(7-((2-((1R,3S,5R)-2-(N-(metoksikarbonil)-L-valil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etinil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heksane-2-karboksilat; metil ((1S)-1-(((2S)-2-(5-(3-((2-((2S)-1-((2R)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1Hbenzimidazol-5-il)etinil)fenil)-1H-imidazol-4-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; (1R)-2-((2S)-2-(5-(3-((2-((2S)-1-((2R)-2-(dietilamino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)etinil)fenil)-1H-imidazol-4-il)-1-pirolidinil)-N,N-dietil-2-okso- 1-feniletanamin; metil ((1S)-1-(((2S)-2-(5-((4-(4-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1Himidazol-5-il)fenil)etinil)-1H-benzimidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; metil ((1S)-1-(((2S,5S)-2-(5-((2-((2S,5S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-5-metil-2-pirolidinil)-1H-nafto[1,2-d]imidazol-7-il)etinil)-1H-benzimidazol-2-il)-5-metil-1-pirolidinil)karbonil)-2-metilpropil)karbamat; metil ((1S)-2-((2S,5S)-2-(7-((2-((2S,5S)-1-((2S)-2-((metoksikarbonil)amino)-2-(tetrahidro-2H-piran-4-il)acetil)-5-metil-2-pirolidinil)-1H-benzimidazol-5-il)etinil)-1H-nafto[1,2-d]imidazol-2-il)-5-metil-1-pirolidinil)-2-okso-1-(tetrahidro-2H-piran-4-il)etil)karbamat; metil ((1S)-1-(((1R,3S,5R)-3-(7-(2-(2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; metil ((1S)-2-((1R,3S,5R)-3-(7-(2-(2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)-2-okso-1-(tetrahidro-2H-piran-4-il)etil)karbamat; (S)-1-acetil-N-(4-((2-((S)-1-(2-fenilacetil)pirolidin-2-il)-1H-benzo[d]imidazol-6-il)etinil)fenil)pirolidin-2-karboksamid; (S)-1-(2-fenilacetil)-N-(4-((2-((S)-1-(2-fenilacetil)pirolidin-2-il)-1H-benzo[d]imidazol-6-il)etinil)fenil)pirolidin-2-karboksamid; (S)-1-acetil-N-(4-(2-(2-((S)-1-(2-fenilacetil)pirolidin-2-il)-1H-benzo[d]imidazol-6-il)etil)fenil)pirolidin-2-karboksamid; (S)-1-(2-fenilacetil)-N-(4-(2-(2-((S)-1-(2-fenilacetil)pirolidin-2-il)-1H-benzo[d]imidazol-6-il)etil)fenil)pirolidin-2-karboksamid; metil ((1R)-2-((2S)-2-((5-(2-(2-((2S)-1-((2R)-2-((metoksikarbonil)amino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)-1,3-oksazol-5-il)-2-metilfenil)karbamoil)-1-pirolidinil)-2-okso-1-feniletil)karbamat; metil (R)-2-((S)-2-(S-(2-(2-((S)-1-((R)-2-(dimetilamino)-2-fenilacetil)pirolidin-2-il)-1H-benzo[d]imidazol-5-il)oksazol-5-il)-2-metilfenilkarbamoil)pirolidin-1-il)-2-okso-1-feniletilkarbamat; metil ((1R)-2-((2S)-2-((3-(2-(2-((2S)-1-((2R)-2-((metoksikarbonil)amino)-2-fenilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)-1,3-oksazol-5-il)fenil)karbamoil)-1-pirolidinil)-2-okso-1-feniletil)karbamat; 2-((2S)-1-((2R)-2-fenil-2-(1-piperidinil)acetil)-2-pirolidinil)-5-(4-((2-((2S)-1-((2R)-2-fenil-2-(1-piperidinil)acetil)-2-pirolidinil)-1H-imidazol-4-il)etinil)fenil)-1H-benzimidazole; metil ((1S)-1-(((1R,3S,5R)-3-(7-(2-(2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)karbonil)-2-metilpropil)karbamat; metil ((1S)-2-((1R,3S,5R)-3-(7-(2-(2-((1R,3S,5R)-2-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-azabiciklo[3.1.0]heks-3-il)-1H-benzimidazol-5-il)etil)-1H-nafto[1,2-d]imidazol-2-il)-2-azabiciklo[3.1.0]heks-2-il)-2-okso-1-(tetrahidro-2H-piran-4-il)etil)karbamat; metil ((1S)-1-(((2S)-2-(4-(2-(4-(2-((2S)-1-((2S)-2-((metoksikarbonil)amino)-3-metilbutanoil)-2-pirolidinil)-1H-benzimidazol-5-il)fenil)etil)-1H-imidazol-2-il)-1-pirolidinil)karbonil)-2-metilpropil)karbamat; 1-(ciklopropilacetil)-N-(3-(5-(2-((2S)-1-(ciklopropilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)-1,3-oksazol-2-il)fenil)-L-prolinamide; i 1-(ciklopropilacetil)-N-(3-(2-(2-((2S)-1-(ciklopropilacetil)-2-pirolidinil)-1H-benzimidazol-5-il)-1,3-oksazol-5-il)fenil)-L-prolinamid; ili njegova farmaceutski prihvatljiva sol.
16. Smjesa koja sadrži spoj prema bilo kojem od zahtjeva 1 do 15, ili njegova farmaceutski prihvatljiva sol, i farmaceutski prihvatljiv nosač.
17. Smjesa prema zahtjevu 16 koja dalje sadrži jedan ili dva dodatna spoja s anti-HCV aktivnošću.
18. Smjesa prema zahtjevu 17 gdje je barem jedan od dodatnih spojeva interferon ili ribavirin.
19. Smjesa prema zahtjevu 18 gdje se interferon izabire između interferona alfa 2B, pegiliranog interferona alfa, konsenzus interferona, interferona alfa 2A, i limfoblastoidnog interferona tau.
20. Smjesa prema zahtjevu 17 gdje se barem jedan od dodatnih spojeva izabire između interleukina 2, interleukina 6, interleukina 12, spoja koji potiče razvoj odgovora pomoćnih T stanica tipa 1, interferirajuće RNA, anti-sense RNA, imikvimoda, ribavirina, inhibitora dehidrogenaze inozin 5’-monofosfata, amantadina, i rimantadina.
21. Smjesa prema zahtjevu 17 gdje je barem jedan od dodatnih spojeva učinkovit u inhibiciji funkcije cilja izabranog između HCV metaloproteaze, HCV serin proteaze, HCV polimeraze, HCV helikaze, HCV NS4B proteina, HCV ulaza, HCV sastavljanja, HCV izlaza, HCV NS5A proteina, i IMPDH za liječenje HCV infekcije.
22. Spoj prema bilo kojem od zahtjeva 1 do 15 ili njegova farmaceutski prihvatljiva sol za uporabu u postupku liječenja HCV infekcije.
23. Spoj za uporabu prema zahtjevu 22 koja dalje obuhvaća primjenu jednog ili dva dodatna spoja s anti-HCV aktivnošću prije, nakon ili istodobno sa spojem iz zahtjeva 1, ili njegova farmaceutski prihvatljiva sol.
24. Spoj za uporabu prema zahtjevu 23 gdje je barem jedan od dodatnih spojeva interferon ili ribavirin.
25. Spoj za uporabu prema zahtjevu 24 gdje se interferon izabire između interferona alfa 2B, pegiliranog interferona alfa, konsenzus interferoan, interferona alfa 2A, i limfoblastoidnog interferona tau.
26. Spoj za uporabu prema zahtjevu 23 gdje se barem jedan od dodatnih spojeva izabire između interleukina 2, interleukina 6, interleukina 12, spoja koji potiče razvoj odgovora pomoćnih T stanica tipa 1, interferirajuće RNA, anti-sense RNA, imikvimoda, ribavirina, inhibitora dehidrogenaze inozin 5’-monofosfata, amantadina, i rimantadina.
27. Spoj za uporabu prema zahtjevu 23 gdje je barem jedan od dodatnih spojeva učinkovit u inhibiciji funkcije cilja izabranog između HCV metaloproteaze, HCV serin proteaze, HCV polimeraze, HCV helikaze, HCV NS4B proteina, HCV ulaza, HCV sastavljanja, HCV izlaza, HCV NS5A proteina, i IMPDH za liječenje HCV infekcije.
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