JP2007531749A5 - - Google Patents
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- Publication number
- JP2007531749A5 JP2007531749A5 JP2007506466A JP2007506466A JP2007531749A5 JP 2007531749 A5 JP2007531749 A5 JP 2007531749A5 JP 2007506466 A JP2007506466 A JP 2007506466A JP 2007506466 A JP2007506466 A JP 2007506466A JP 2007531749 A5 JP2007531749 A5 JP 2007531749A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- optionally substituted
- hydroxy
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 1018
- 125000003545 alkoxy group Chemical group 0.000 claims description 502
- 125000001153 fluoro group Chemical group F* 0.000 claims description 462
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 402
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 370
- -1 nitro, hydroxy Chemical group 0.000 claims description 369
- 125000005843 halogen group Chemical group 0.000 claims description 345
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 315
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 248
- 229910052799 carbon Inorganic materials 0.000 claims description 164
- 229910052739 hydrogen Inorganic materials 0.000 claims description 163
- 125000003118 aryl group Chemical group 0.000 claims description 142
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 109
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 109
- 150000001875 compounds Chemical class 0.000 claims description 105
- 125000001424 substituent group Chemical group 0.000 claims description 99
- 125000003342 alkenyl group Chemical group 0.000 claims description 90
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 66
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 48
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 48
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 46
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 44
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 44
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 44
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 44
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 44
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 44
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 44
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 44
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 43
- 229910052717 sulfur Chemical group 0.000 claims description 43
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 40
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 125000002541 furyl group Chemical group 0.000 claims description 38
- 125000002971 oxazolyl group Chemical group 0.000 claims description 38
- 125000004076 pyridyl group Chemical group 0.000 claims description 38
- 125000000335 thiazolyl group Chemical group 0.000 claims description 38
- 125000001544 thienyl group Chemical group 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 33
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 32
- 150000001408 amides Chemical class 0.000 claims description 30
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 30
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 29
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 27
- 125000002757 morpholinyl group Chemical group 0.000 claims description 26
- 125000004193 piperazinyl group Chemical group 0.000 claims description 26
- 125000003386 piperidinyl group Chemical group 0.000 claims description 26
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 26
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 25
- 229910052721 tungsten Inorganic materials 0.000 claims description 24
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 23
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 23
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 23
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 23
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 23
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 23
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 23
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 23
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 22
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 22
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 22
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 22
- 125000001624 naphthyl group Chemical group 0.000 claims description 22
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 22
- 229930192474 thiophene Natural products 0.000 claims description 22
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 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 19
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
- 239000011593 sulfur Chemical group 0.000 claims description 11
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 229940002612 prodrug Drugs 0.000 claims description 8
- 239000000651 prodrug Substances 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 229930194542 Keto Natural products 0.000 claims description 7
- SCPFBFZSUQUSDM-UHFFFAOYSA-N O(C1=CC=CC=C1)NS(=O)(=O)SC1=CC=CC=C1 Chemical compound O(C1=CC=CC=C1)NS(=O)(=O)SC1=CC=CC=C1 SCPFBFZSUQUSDM-UHFFFAOYSA-N 0.000 claims description 7
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 7
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000000468 ketone group Chemical group 0.000 claims description 7
- 150000003457 sulfones Chemical class 0.000 claims description 7
- 150000003462 sulfoxides Chemical class 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 241000065675 Cyclops Species 0.000 claims description 2
- 206010056740 Genital discharge Diseases 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 141
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 48
- 108010047761 Interferon-alpha Proteins 0.000 claims 28
- 102000006992 Interferon-alpha Human genes 0.000 claims 28
- 239000002777 nucleoside Substances 0.000 claims 26
- 230000003908 liver function Effects 0.000 claims 24
- 208000019425 cirrhosis of liver Diseases 0.000 claims 21
- 230000002708 enhancing effect Effects 0.000 claims 21
- OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 claims 20
- 102100037850 Interferon gamma Human genes 0.000 claims 17
- 108010074328 Interferon-gamma Proteins 0.000 claims 17
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 17
- 108010010648 interferon alfacon-1 Proteins 0.000 claims 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 15
- 239000003937 drug carrier Substances 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 101800001530 Thymosin alpha Proteins 0.000 claims 10
- 125000004429 atom Chemical group 0.000 claims 10
- 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 9
- 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 9
- 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 9
- 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 9
- 229940121740 Inosine monophosphate dehydrogenase inhibitor Drugs 0.000 claims 9
- 101800001554 RNA-directed RNA polymerase Proteins 0.000 claims 9
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group 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 9
- 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 9
- 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 9
- 229960004748 abacavir Drugs 0.000 claims 9
- 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 9
- 229960001997 adefovir Drugs 0.000 claims 9
- 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 9
- 229960000724 cidofovir Drugs 0.000 claims 9
- 229940014461 combivir Drugs 0.000 claims 9
- 229940079593 drug Drugs 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 9
- 238000009472 formulation Methods 0.000 claims 9
- 239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- 229960000329 ribavirin Drugs 0.000 claims 9
- 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 9
- 239000003730 rna directed rna polymerase inhibitor Substances 0.000 claims 9
- 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 9
- 229950006081 taribavirin Drugs 0.000 claims 9
- 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 8
- 229960003130 interferon gamma Drugs 0.000 claims 8
- 229950003954 isatoribine Drugs 0.000 claims 8
- 229920001223 polyethylene glycol Polymers 0.000 claims 8
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 7
- 125000005647 linker group Chemical group 0.000 claims 7
- 239000013011 aqueous formulation Substances 0.000 claims 6
- 230000003993 interaction Effects 0.000 claims 5
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 4
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- 206010019668 Hepatic fibrosis Diseases 0.000 claims 3
- 239000007894 caplet Substances 0.000 claims 3
- 239000007963 capsule composition Substances 0.000 claims 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 229940090438 infergen Drugs 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 150000005846 sugar alcohols Chemical class 0.000 claims 3
- 230000002459 sustained effect Effects 0.000 claims 3
- 239000007916 tablet composition Substances 0.000 claims 3
- 150000007970 thio esters Chemical class 0.000 claims 3
- 150000003556 thioamides Chemical class 0.000 claims 3
- 230000004044 response Effects 0.000 claims 2
- 230000003612 virological effect Effects 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229940127073 nucleoside analogue Drugs 0.000 claims 1
- 230000008593 response to virus Effects 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 0 CC=CCCCCCC(*)C(N(CC(C1)NC(*)=*)[C@@]1C(NC1(*)CC1)=O)=O Chemical compound CC=CCCCCCC(*)C(N(CC(C1)NC(*)=*)[C@@]1C(NC1(*)CC1)=O)=O 0.000 description 6
- 238000000034 method Methods 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 description 1
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 1
- GGDYAKVUZMZKRV-UHFFFAOYSA-N 2-fluoroethanol Chemical compound OCCF GGDYAKVUZMZKRV-UHFFFAOYSA-N 0.000 description 1
- MIXUNNYDJUJFAB-UHFFFAOYSA-N 2-propylheptadec-5-enoic acid Chemical compound CCCCCCCCCCCC=CCCC(C(O)=O)CCC MIXUNNYDJUJFAB-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- ZPPXWZDJDIOJFP-UHFFFAOYSA-N OC(N(C1)Cc2c1cccc2)=O Chemical compound OC(N(C1)Cc2c1cccc2)=O ZPPXWZDJDIOJFP-UHFFFAOYSA-N 0.000 description 1
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55816104P | 2004-03-30 | 2004-03-30 | |
| US60/558,161 | 2004-03-30 | ||
| US56241804P | 2004-04-14 | 2004-04-14 | |
| US60/562,418 | 2004-04-14 | ||
| US61238104P | 2004-09-22 | 2004-09-22 | |
| US61246004P | 2004-09-22 | 2004-09-22 | |
| US60/612,381 | 2004-09-22 | ||
| US60/612,460 | 2004-09-22 | ||
| PCT/US2005/010494 WO2005095403A2 (en) | 2004-03-30 | 2005-03-29 | Macrocyclic compounds as inhibitors of viral replication |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007531749A JP2007531749A (ja) | 2007-11-08 |
| JP2007531749A5 true JP2007531749A5 (https=) | 2008-06-05 |
| JP4950026B2 JP4950026B2 (ja) | 2012-06-13 |
Family
ID=35005653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2007506466A Expired - Fee Related JP4950026B2 (ja) | 2004-03-30 | 2005-03-29 | ウイルス複製阻害剤としての大環状化合物 |
Country Status (16)
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| EP (1) | EP1749007A2 (https=) |
| JP (1) | JP4950026B2 (https=) |
| AP (1) | AP2006003763A0 (https=) |
| AR (1) | AR050321A1 (https=) |
| AU (1) | AU2005228894B9 (https=) |
| BR (1) | BRPI0509467A (https=) |
| CA (1) | CA2560897C (https=) |
| CU (1) | CU23787B7 (https=) |
| EA (1) | EA012389B1 (https=) |
| EC (1) | ECSP066959A (https=) |
| GE (1) | GEP20104926B (https=) |
| IL (1) | IL177917A0 (https=) |
| MA (1) | MA28548B1 (https=) |
| NO (1) | NO20064933L (https=) |
| NZ (1) | NZ549697A (https=) |
| WO (1) | WO2005095403A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR022061A1 (es) * | 1998-08-10 | 2002-09-04 | Boehringer Ingelheim Ca Ltd | Peptidos inhibidores de la hepatitis c, una composicion farmaceutica que los contiene, el uso de los mismos para preparar una composicion farmaceutica, el uso de un producto intermedio para la preparacion de estos peptidos y un procedimiento para la preparacion de un peptido analogo de los mismos. |
| US6323180B1 (en) * | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
| US6608027B1 (en) * | 1999-04-06 | 2003-08-19 | Boehringer Ingelheim (Canada) Ltd | Macrocyclic peptides active against the hepatitis C virus |
| UA74546C2 (en) * | 1999-04-06 | 2006-01-16 | Boehringer Ingelheim Ca Ltd | Macrocyclic peptides having activity relative to hepatitis c virus, a pharmaceutical composition and use of the pharmaceutical composition |
| DE60119968T2 (de) * | 2000-11-20 | 2007-01-18 | Bristol-Myers Squibb Co. | Hepatitis c tripeptid inhibitoren |
| US6867185B2 (en) * | 2001-12-20 | 2005-03-15 | Bristol-Myers Squibb Company | Inhibitors of hepatitis C virus |
| CA2369711A1 (en) * | 2002-01-30 | 2003-07-30 | Boehringer Ingelheim (Canada) Ltd. | Macrocyclic peptides active against the hepatitis c virus |
| CA2369970A1 (en) * | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| CA2370396A1 (en) * | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| US6828301B2 (en) * | 2002-02-07 | 2004-12-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for hepatitis C viral protease inhibitors |
| JP4312711B2 (ja) * | 2002-05-20 | 2009-08-12 | ブリストル−マイヤーズ スクイブ カンパニー | ヘテロ環式スルホンアミドｃ型肝炎ウイルス阻害剤 |
| MY140680A (en) * | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
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| JP4902361B2 (ja) * | 2004-01-30 | 2012-03-21 | メディヴィル・アクチエボラーグ | Ｈｃｖｎｓ−３セリンプロテアーゼインヒビター |
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2005
- 2005-03-29 AP AP2006003763A patent/AP2006003763A0/xx unknown
- 2005-03-29 EA EA200601467A patent/EA012389B1/ru not_active IP Right Cessation
- 2005-03-29 CA CA2560897A patent/CA2560897C/en not_active Expired - Fee Related
- 2005-03-29 WO PCT/US2005/010494 patent/WO2005095403A2/en not_active Ceased
- 2005-03-29 NZ NZ549697A patent/NZ549697A/en not_active IP Right Cessation
- 2005-03-29 BR BRPI0509467-4A patent/BRPI0509467A/pt not_active IP Right Cessation
- 2005-03-29 EP EP05757750A patent/EP1749007A2/en not_active Withdrawn
- 2005-03-29 JP JP2007506466A patent/JP4950026B2/ja not_active Expired - Fee Related
- 2005-03-29 AU AU2005228894A patent/AU2005228894B9/en not_active Ceased
- 2005-03-29 GE GEAP20059674A patent/GEP20104926B/en unknown
- 2005-03-30 AR ARP050101257A patent/AR050321A1/es not_active Application Discontinuation
-
2006
- 2006-09-06 IL IL177917A patent/IL177917A0/en unknown
- 2006-10-20 MA MA29407A patent/MA28548B1/fr unknown
- 2006-10-27 EC EC2006006959A patent/ECSP066959A/es unknown
- 2006-10-27 NO NO20064933A patent/NO20064933L/no not_active Application Discontinuation
-
2009
- 2009-12-08 CU CU20090209A patent/CU23787B7/es active IP Right Grant
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