IL188693A - Macrocyclic inhibitor of hepatitis C virus multiplication - Google Patents
Macrocyclic inhibitor of hepatitis C virus multiplicationInfo
- Publication number
- IL188693A IL188693A IL188693A IL18869308A IL188693A IL 188693 A IL188693 A IL 188693A IL 188693 A IL188693 A IL 188693A IL 18869308 A IL18869308 A IL 18869308A IL 188693 A IL188693 A IL 188693A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- cycloalkyl
- substituted
- compound
- ifn
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 204
- 241000711549 Hepacivirus C Species 0.000 title description 90
- 230000029812 viral genome replication Effects 0.000 title description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 457
- 150000001875 compounds Chemical class 0.000 claims description 378
- 108010074328 Interferon-gamma Proteins 0.000 claims description 257
- 102100037850 Interferon gamma Human genes 0.000 claims description 239
- 238000000034 method Methods 0.000 claims description 207
- -1 chloropyridinyl Chemical group 0.000 claims description 199
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 190
- 239000003814 drug Substances 0.000 claims description 184
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 178
- 239000005557 antagonist Substances 0.000 claims description 173
- 125000003545 alkoxy group Chemical group 0.000 claims description 163
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 144
- 125000001153 fluoro group Chemical group F* 0.000 claims description 140
- 125000003118 aryl group Chemical group 0.000 claims description 118
- 125000005843 halogen group Chemical group 0.000 claims description 114
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 113
- 108010010648 interferon alfacon-1 Proteins 0.000 claims description 95
- 229910052739 hydrogen Inorganic materials 0.000 claims description 92
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 86
- 229940090438 infergen Drugs 0.000 claims description 64
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 62
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims description 58
- 230000003442 weekly effect Effects 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 49
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 48
- 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 description 45
- 125000004076 pyridyl group Chemical group 0.000 claims description 44
- 229960000329 ribavirin Drugs 0.000 claims description 43
- 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 description 43
- 150000003839 salts Chemical class 0.000 claims description 43
- 229910052760 oxygen Inorganic materials 0.000 claims description 42
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 41
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 39
- 150000002148 esters Chemical class 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 36
- 108010008165 Etanercept Proteins 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 239000000651 prodrug Substances 0.000 claims description 34
- 229940002612 prodrug Drugs 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 229960002964 adalimumab Drugs 0.000 claims description 28
- 125000003342 alkenyl group Chemical group 0.000 claims description 28
- 229960000403 etanercept Drugs 0.000 claims description 28
- 229960000598 infliximab Drugs 0.000 claims description 28
- 125000001624 naphthyl group Chemical group 0.000 claims description 28
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
- 125000002541 furyl group Chemical group 0.000 claims description 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- 102000014150 Interferons Human genes 0.000 claims description 19
- 108010050904 Interferons Proteins 0.000 claims description 19
- 229960003073 pirfenidone Drugs 0.000 claims description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000002757 morpholinyl group Chemical group 0.000 claims description 17
- 125000002971 oxazolyl group Chemical group 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 108091005804 Peptidases Proteins 0.000 claims description 16
- 239000004365 Protease Substances 0.000 claims description 16
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 16
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 16
- 125000004193 piperazinyl group Chemical group 0.000 claims description 16
- 125000003386 piperidinyl group Chemical group 0.000 claims description 16
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 16
- 125000001995 cyclobutyl group Chemical class [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- 125000000335 thiazolyl group Chemical group 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 230000003612 virological effect Effects 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 108010047761 Interferon-alpha Proteins 0.000 claims description 13
- 102000006992 Interferon-alpha Human genes 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 11
- 229940079322 interferon Drugs 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims description 10
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 230000004044 response Effects 0.000 claims description 10
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims description 10
- 229960000311 ritonavir Drugs 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000003368 amide group Chemical group 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 claims description 7
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 7
- 235000019000 fluorine Nutrition 0.000 claims description 7
- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 7
- 230000002459 sustained effect Effects 0.000 claims description 7
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 6
- 101100079984 Caenorhabditis elegans nhr-9 gene Proteins 0.000 claims description 6
- IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052721 tungsten Inorganic materials 0.000 claims description 5
- 208000005176 Hepatitis C Diseases 0.000 claims description 4
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 4
- 239000002777 nucleoside Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 claims description 4
- 229950006081 taribavirin Drugs 0.000 claims description 4
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 claims description 3
- 102000008070 Interferon-gamma Human genes 0.000 claims description 3
- 229930194542 Keto Natural products 0.000 claims description 3
- 101800001554 RNA-directed RNA polymerase Proteins 0.000 claims description 3
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229960003130 interferon gamma Drugs 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 3
- VWFCHDSQECPREK-LURJTMIESA-N Cidofovir Chemical compound NC=1C=CN(C[C@@H](CO)OCP(O)(O)=O)C(=O)N=1 VWFCHDSQECPREK-LURJTMIESA-N 0.000 claims description 2
- GLWHPRRGGYLLRV-XLPZGREQSA-N [[(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](N=[N+]=[N-])C1 GLWHPRRGGYLLRV-XLPZGREQSA-N 0.000 claims description 2
- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 claims description 2
- 229960004748 abacavir Drugs 0.000 claims description 2
- 229960001997 adefovir Drugs 0.000 claims description 2
- WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 229960000724 cidofovir Drugs 0.000 claims description 2
- 229940014461 combivir Drugs 0.000 claims description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 2
- 238000000338 in vitro Methods 0.000 claims description 2
- 150000003557 thiazoles Chemical class 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- UJQBOUAGWGVOTI-XSSZXYGBSA-N 1-[(2r,4s,5r)-4-azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@](O)(N=[N+]=[N-])C1 UJQBOUAGWGVOTI-XSSZXYGBSA-N 0.000 claims 1
- TZYVRXZQAWPIAB-FCLHUMLKSA-N 5-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4h-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione Chemical compound O=C1SC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TZYVRXZQAWPIAB-FCLHUMLKSA-N 0.000 claims 1
- 229940121759 Helicase inhibitor Drugs 0.000 claims 1
- 206010019670 Hepatic function abnormal Diseases 0.000 claims 1
- 229940121740 Inosine monophosphate dehydrogenase inhibitor Drugs 0.000 claims 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims 1
- 229940123066 Polymerase inhibitor Drugs 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 125000000033 alkoxyamino group Chemical group 0.000 claims 1
- 125000005157 alkyl carboxy group Chemical group 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims 1
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- 239000003730 rna directed rna polymerase inhibitor Substances 0.000 claims 1
- 125000001174 sulfone group Chemical group 0.000 claims 1
- VGUNCVGRXFWLAS-UHFFFAOYSA-N thiophen-2-yl N-[carbamoyl(phenoxy)amino]sulfamate Chemical compound O(C1=CC=CC=C1)N(C(=O)N)NS(=O)(=O)OC=1SC=CC1 VGUNCVGRXFWLAS-UHFFFAOYSA-N 0.000 claims 1
- 102000003390 tumor necrosis factor Human genes 0.000 claims 1
- 238000011282 treatment Methods 0.000 description 215
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- MRKKUGDWODATMF-SECBINFHSA-N (2R)-2-[[5-methoxy-2-(methylamino)pyrimidin-4-yl]amino]hexan-1-ol Chemical compound CCCC[C@H](CO)Nc1nc(NC)ncc1OC MRKKUGDWODATMF-SECBINFHSA-N 0.000 description 57
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- 125000004429 atom Chemical group 0.000 description 46
- 238000002648 combination therapy Methods 0.000 description 38
- 210000002966 serum Anatomy 0.000 description 37
- 238000002560 therapeutic procedure Methods 0.000 description 34
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 32
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 32
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 32
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 16
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- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 16
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 16
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- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 16
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
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- 238000009472 formulation Methods 0.000 description 15
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- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 14
- 108010092853 peginterferon alfa-2a Proteins 0.000 description 14
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 13
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Classifications
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- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/177—Receptors; Cell surface antigens; Cell surface determinants
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- A61K38/22—Hormones
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- 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
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- 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
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- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
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- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| PCT/US2006/027738 WO2007015824A2 (en) | 2005-07-25 | 2006-07-17 | Novel macrocyclic inhibitors of hepatitis c virus replication |
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| IL188693A0 IL188693A0 (en) | 2008-08-07 |
| IL188693A true IL188693A (en) | 2012-08-30 |
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| IL221361A IL221361A0 (en) | 2005-07-25 | 2012-08-08 | Novel macrocyclic inhibitors of hepatitis c virus replication |
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| IL221361A IL221361A0 (en) | 2005-07-25 | 2012-08-08 | Novel macrocyclic inhibitors of hepatitis c virus replication |
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| JP2003007697A (ja) * | 2001-06-21 | 2003-01-10 | Hitachi Kokusai Electric Inc | 半導体装置の製造方法、基板処理方法および基板処理装置 |
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| US7491794B2 (en) * | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
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| RU2008152171A (ru) * | 2006-07-05 | 2010-08-10 | Интермьюн, Инк. (Us) | Новые ингибиторы вирусной репликации гепатита с |
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- 2006-07-17 AU AU2006276246A patent/AU2006276246B2/en not_active Ceased
- 2006-07-17 US US11/996,902 patent/US20090148407A1/en not_active Abandoned
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