HRP20130063T1 - Inhibitori virusa hepatitisa c - Google Patents
Inhibitori virusa hepatitisa c Download PDFInfo
- 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
- Authority
- HR
- Croatia
- Prior art keywords
- pyrrolidinyl
- methyl
- benzimidazol
- imidazol
- methoxycarbonyl
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims 2
- 241000711549 Hepacivirus C Species 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 59
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 48
- 150000001875 compounds Chemical class 0.000 claims 33
- -1 (2S)-2-(8-(4-(2-((2S)-1-((2S)-2-((methoxycarbonyl)amino)-3 -methylbutanoyl)-2-pyrrolidinyl)-1Himidazol-4-yl)phenyl)-1,4,5,6-tetrahydrobenzo[3,4]cyclohepta[1,2-d]imidazol-2-yl)-1-pyrrolidinyl Chemical group 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 10
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims 9
- 108010047761 Interferon-alpha Proteins 0.000 claims 6
- 102000006992 Interferon-alpha Human genes 0.000 claims 6
- 108010050904 Interferons Proteins 0.000 claims 6
- 102000014150 Interferons Human genes 0.000 claims 6
- 229940079322 interferon Drugs 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229960000329 ribavirin Drugs 0.000 claims 4
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- VCAZJSQXGIMRDZ-SPUOKHKDSA-N (2r)-2-(diethylamino)-1-[(2s)-2-[4-[3-[2-[2-[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-3h-benzimidazol-5-yl]ethynyl]phenyl]-1h-imidazol-5-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(CC)CC)C(=O)N2CCC[C@H]2C=2N=CNC=2C=2C=CC=C(C=2)C#CC=2C=C3N=C(NC3=CC=2)[C@@H]2CCCN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=CC=CC=C1 VCAZJSQXGIMRDZ-SPUOKHKDSA-N 0.000 claims 2
- IZCGPYRQOMSTGW-ZPGRZCPFSA-N (2s)-1-(2-phenylacetyl)-n-[4-[2-[2-[(2s)-1-(2-phenylacetyl)pyrrolidin-2-yl]-3h-benzimidazol-5-yl]ethyl]phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CCC1)C(=O)NC=1C=CC(CCC=2C=C3NC(=NC3=CC=2)[C@H]2N(CCC2)C(=O)CC=2C=CC=CC=2)=CC=1)C(=O)CC1=CC=CC=C1 IZCGPYRQOMSTGW-ZPGRZCPFSA-N 0.000 claims 2
- HJAGWVHBOKXBAR-ZPGRZCPFSA-N (2s)-1-(2-phenylacetyl)-n-[4-[2-[2-[(2s)-1-(2-phenylacetyl)pyrrolidin-2-yl]-3h-benzimidazol-5-yl]ethynyl]phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CCC1)C(=O)NC=1C=CC(=CC=1)C#CC=1C=C2NC(=NC2=CC=1)[C@H]1N(CCC1)C(=O)CC=1C=CC=CC=1)C(=O)CC1=CC=CC=C1 HJAGWVHBOKXBAR-ZPGRZCPFSA-N 0.000 claims 2
- VPYPHRNGQLLTRN-CONSDPRKSA-N (2s)-1-acetyl-n-[4-[2-[2-[(2s)-1-(2-phenylacetyl)pyrrolidin-2-yl]-3h-benzimidazol-5-yl]ethyl]phenyl]pyrrolidine-2-carboxamide Chemical compound CC(=O)N1CCC[C@H]1C(=O)NC(C=C1)=CC=C1CCC1=CC=C(N=C(N2)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)C2=C1 VPYPHRNGQLLTRN-CONSDPRKSA-N 0.000 claims 2
- SNHCKLSBXJOYKR-CONSDPRKSA-N (2s)-1-acetyl-n-[4-[2-[2-[(2s)-1-(2-phenylacetyl)pyrrolidin-2-yl]-3h-benzimidazol-5-yl]ethynyl]phenyl]pyrrolidine-2-carboxamide Chemical compound CC(=O)N1CCC[C@H]1C(=O)NC1=CC=C(C#CC=2C=C3NC(=NC3=CC=2)[C@H]2N(CCC2)C(=O)CC=2C=CC=CC=2)C=C1 SNHCKLSBXJOYKR-CONSDPRKSA-N 0.000 claims 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 2
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 2
- 108020005544 Antisense RNA Proteins 0.000 claims 2
- 101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 claims 2
- 102100040018 Interferon alpha-2 Human genes 0.000 claims 2
- 108010079944 Interferon-alpha2b Proteins 0.000 claims 2
- 102000013462 Interleukin-12 Human genes 0.000 claims 2
- 108010065805 Interleukin-12 Proteins 0.000 claims 2
- 102000000588 Interleukin-2 Human genes 0.000 claims 2
- 108010002350 Interleukin-2 Proteins 0.000 claims 2
- 102000004889 Interleukin-6 Human genes 0.000 claims 2
- 108090001005 Interleukin-6 Proteins 0.000 claims 2
- 102000005741 Metalloproteases Human genes 0.000 claims 2
- 108010006035 Metalloproteases Proteins 0.000 claims 2
- 108060004795 Methyltransferase Proteins 0.000 claims 2
- 101800001019 Non-structural protein 4B Proteins 0.000 claims 2
- 101800001014 Non-structural protein 5A Proteins 0.000 claims 2
- 102000012479 Serine Proteases Human genes 0.000 claims 2
- 108010022999 Serine Proteases Proteins 0.000 claims 2
- 230000005867 T cell response Effects 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 2
- 229960003805 amantadine Drugs 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 239000003184 complementary RNA Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims 2
- 229960002751 imiquimod Drugs 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 230000002452 interceptive effect Effects 0.000 claims 2
- 229940117681 interleukin-12 Drugs 0.000 claims 2
- 229940100601 interleukin-6 Drugs 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Chemical group 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- 229960000888 rimantadine Drugs 0.000 claims 2
- YVBRVHHVXMEIRH-LZCGGXSTSA-N (2r)-2-(diethylamino)-1-[(2s)-2-[6-[2-[4-[2-[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]ethynyl]-1h-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(CC)CC)C(=O)N2CCC[C@H]2C=2NC3=CC=C(C=C3N=2)C#CC2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=CC=CC=C1 YVBRVHHVXMEIRH-LZCGGXSTSA-N 0.000 claims 1
- ICOHANMFASPHFD-IYTFMMMVSA-N (2r)-2-(diethylamino)-1-[(2s)-2-[6-[3-[2-[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]-1h-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(CC)CC)C(=O)N2CCC[C@H]2C=2NC3=CC=C(C=C3N=2)C=2C=CC=C(C=2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=CC=CC=C1 ICOHANMFASPHFD-IYTFMMMVSA-N 0.000 claims 1
- XSIMJIAOGYTKCF-IYTFMMMVSA-N (2r)-2-(diethylamino)-1-[(2s)-2-[6-[4-[2-[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]-1h-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(CC)CC)C(=O)N2CCC[C@H]2C=2NC3=CC=C(C=C3N=2)C2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=CC=CC=C1 XSIMJIAOGYTKCF-IYTFMMMVSA-N 0.000 claims 1
- FYMANEAIPMZKAM-JRTLPCBOSA-N (2r)-2-phenyl-1-[(2s)-2-[6-[4-[2-[2-[(2s)-1-[(2r)-2-phenyl-2-piperidin-1-ylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]ethynyl]phenyl]-1h-benzimidazol-2-yl]pyrrolidin-1-yl]-2-piperidin-1-ylethanone Chemical compound N1([C@@H](C(=O)N2[C@@H](CCC2)C=2NC=C(N=2)C#CC=2C=CC(=CC=2)C=2C=C3N=C(NC3=CC=2)[C@H]2N(CCC2)C(=O)[C@H](N2CCCCC2)C=2C=CC=CC=2)C=2C=CC=CC=2)CCCCC1 FYMANEAIPMZKAM-JRTLPCBOSA-N 0.000 claims 1
- 101710088194 Dehydrogenase Proteins 0.000 claims 1
- 229940124186 Dehydrogenase inhibitor Drugs 0.000 claims 1
- GRSZFWQUAKGDAV-KQYNXXCUSA-N IMP Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H]1N1C(NC=NC2=O)=C2N=C1 GRSZFWQUAKGDAV-KQYNXXCUSA-N 0.000 claims 1
- 229930010555 Inosine Natural products 0.000 claims 1
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 229960003786 inosine Drugs 0.000 claims 1
- RCCASXOCOJRZPA-CDBYGCFJSA-N methyl n-[(1r)-2-[(2s)-2-[5-[3-[2-[(2s)-1-[(2r)-2-(methoxycarbonylamino)-2-phenylacetyl]pyrrolidin-2-yl]-3h-benzimidazol-5-yl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound C1([C@@H](NC(=O)OC)C(=O)N2CCC[C@H]2C=2NC3=CC=C(C=C3N=2)C=2C=CC=C(C=2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](NC(=O)OC)C=2C=CC=CC=2)=CC=CC=C1 RCCASXOCOJRZPA-CDBYGCFJSA-N 0.000 claims 1
- QXLFJWJLUQIKQX-CDBYGCFJSA-N methyl n-[(1r)-2-[(2s)-2-[5-[4-[2-[(2s)-1-[(2r)-2-(methoxycarbonylamino)-2-phenylacetyl]pyrrolidin-2-yl]-3h-benzimidazol-5-yl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound C1([C@@H](NC(=O)OC)C(=O)N2CCC[C@H]2C=2NC3=CC=C(C=C3N=2)C2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](NC(=O)OC)C=2C=CC=CC=2)=CC=CC=C1 QXLFJWJLUQIKQX-CDBYGCFJSA-N 0.000 claims 1
Classifications
-
- 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
- C07D403/14—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 three or more hetero rings
-
- 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
- A61K31/41—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
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61K31/41—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
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
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- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/19—Cytokines; Lymphokines; Interferons
- A61K38/20—Interleukins [IL]
- A61K38/2013—IL-2
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- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/19—Cytokines; Lymphokines; Interferons
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- A61K38/204—IL-6
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- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/19—Cytokines; Lymphokines; Interferons
- A61K38/20—Interleukins [IL]
- A61K38/208—IL-12
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- A—HUMAN NECESSITIES
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- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
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- A61K38/19—Cytokines; Lymphokines; Interferons
- 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
- A61K38/19—Cytokines; Lymphokines; Interferons
- A61K38/21—Interferons [IFN]
- A61K38/212—IFN-alpha
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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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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