JP2008540463A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008540463A5 JP2008540463A5 JP2008510379A JP2008510379A JP2008540463A5 JP 2008540463 A5 JP2008540463 A5 JP 2008540463A5 JP 2008510379 A JP2008510379 A JP 2008510379A JP 2008510379 A JP2008510379 A JP 2008510379A JP 2008540463 A5 JP2008540463 A5 JP 2008540463A5
- Authority
- JP
- Japan
- Prior art keywords
- trans
- methyl
- amino
- thiophene
- cyclohexyl
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims 61
- -1 substituted Chemical class 0.000 claims 46
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- 125000001072 heteroaryl group Chemical group 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims 16
- 239000012453 solvate Substances 0.000 claims 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 11
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 10
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 7
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 230000003612 virological effect Effects 0.000 claims 6
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims 5
- 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 5
- 238000000034 method Methods 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 230000009385 viral infection Effects 0.000 claims 5
- NRWYAVDHRVTITK-UPRSBDKSSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCC=1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCC=1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 NRWYAVDHRVTITK-UPRSBDKSSA-N 0.000 claims 4
- 241000710781 Flaviviridae Species 0.000 claims 4
- 108020004684 Internal Ribosome Entry Sites Proteins 0.000 claims 4
- 208000036142 Viral infection Diseases 0.000 claims 4
- 239000003443 antiviral agent Substances 0.000 claims 4
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- 150000002923 oximes Chemical class 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- JVSQRBKXYYHNAL-UHFFFAOYSA-N 3-[(4-hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]-5-(4-phenoxycyclohexen-1-yl)thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1CCC(CC=1)OC=1C=CC=CC=1)C(O)=O)C1CCC(O)CC1 JVSQRBKXYYHNAL-UHFFFAOYSA-N 0.000 claims 3
- HCTFEOYQHVJAEV-UAPYVXQJSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCN(C)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCN(C)CC1 HCTFEOYQHVJAEV-UAPYVXQJSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- AMOXNTAMLUCWJT-UHFFFAOYSA-N 5-(4,4-dimethylcyclohexyl)-3-[(4-methoxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(OC)CCC1N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)C(=O)C1CCC(C)CC1 AMOXNTAMLUCWJT-UHFFFAOYSA-N 0.000 claims 2
- OFOMFFOXKMZUIW-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-(n-(4-methylcyclohexanecarbonyl)anilino)thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C=1C=CC=CC=1)C1=C(C(O)=O)SC(C=2CCCCC=2)=C1 OFOMFFOXKMZUIW-UHFFFAOYSA-N 0.000 claims 2
- GJNZQSSHAVNWFW-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[(2,4-dichlorobenzoyl)-propan-2-ylamino]thiophene-2-carboxylic acid Chemical compound C1=C(C=2CCCCC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(Cl)C=C1Cl GJNZQSSHAVNWFW-UHFFFAOYSA-N 0.000 claims 2
- KQXCUMQUYNMNKA-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[(2,4-dimethylphenyl)sulfonylamino]thiophene-2-carboxylic acid Chemical compound CC1=CC(C)=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2CCCCC=2)=C1 KQXCUMQUYNMNKA-UHFFFAOYSA-N 0.000 claims 2
- OSZNFYRPACBWAD-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[(4-ethoxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(OCC)CCC1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)C1CCC(C)CC1 OSZNFYRPACBWAD-UHFFFAOYSA-N 0.000 claims 2
- MGIDOELNCIGRPO-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[(4-hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCC(O)CC1 MGIDOELNCIGRPO-UHFFFAOYSA-N 0.000 claims 2
- VQNVTTOMIYUAAT-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[(4-methylbenzoyl)-propan-2-ylamino]thiophene-2-carboxylic acid Chemical compound C1=C(C=2CCCCC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(C)C=C1 VQNVTTOMIYUAAT-UHFFFAOYSA-N 0.000 claims 2
- HQUCUQJOQOFEQW-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[(4-methylcyclohexanecarbonyl)-(4-oxocyclohexyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCC(=O)CC1 HQUCUQJOQOFEQW-UHFFFAOYSA-N 0.000 claims 2
- NHRHXDMGFVGNRU-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[1,3-dioxan-5-yl-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1COCOC1 NHRHXDMGFVGNRU-UHFFFAOYSA-N 0.000 claims 2
- SNHOCYVWFCETLM-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[[4-(methoxymethoxy)cyclohexyl]-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(OCOC)CCC1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)C1CCC(C)CC1 SNHOCYVWFCETLM-UHFFFAOYSA-N 0.000 claims 2
- VRCATWVIEHHTHZ-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[cyclohexyl-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCCCC1 VRCATWVIEHHTHZ-UHFFFAOYSA-N 0.000 claims 2
- CHSWOVCXLYDIIY-UHFFFAOYSA-N 5-(cyclopenten-1-yl)-3-[(2,4-dichlorobenzoyl)-propan-2-ylamino]thiophene-2-carboxylic acid Chemical compound C1=C(C=2CCCC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(Cl)C=C1Cl CHSWOVCXLYDIIY-UHFFFAOYSA-N 0.000 claims 2
- NRWYAVDHRVTITK-UHFFFAOYSA-N 5-(cyclopenten-1-yl)-3-[(4-hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1CCCC=1)C(O)=O)C1CCC(O)CC1 NRWYAVDHRVTITK-UHFFFAOYSA-N 0.000 claims 2
- VCJJWZOMFHUKMX-UHFFFAOYSA-N 5-cyclohexyl-3-[(4-hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C1CCCCC1)C(O)=O)C1CCC(O)CC1 VCJJWZOMFHUKMX-UHFFFAOYSA-N 0.000 claims 2
- HZCUBYGLTQHCPR-JCNLHEQBSA-N C1=C(C=2CCCCC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)[C@H]1CC[C@H](C)CC1 Chemical compound C1=C(C=2CCCCC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)[C@H]1CC[C@H](C)CC1 HZCUBYGLTQHCPR-JCNLHEQBSA-N 0.000 claims 2
- QHSXCGCAECGORC-LWLBLJAOSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1C=CC(C)CC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1C=CC(C)CC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 QHSXCGCAECGORC-LWLBLJAOSA-N 0.000 claims 2
- FPARYJXWWMDFFU-KQEUCTNFSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1C=CCCC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1C=CCCC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 FPARYJXWWMDFFU-KQEUCTNFSA-N 0.000 claims 2
- JZZHJWYJGBDGPG-BRWVVXTDSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CC=C(C)CC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CC=C(C)CC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 JZZHJWYJGBDGPG-BRWVVXTDSA-N 0.000 claims 2
- BVXHTXRVCMTCJW-LWLBLJAOSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)CC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)CC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 BVXHTXRVCMTCJW-LWLBLJAOSA-N 0.000 claims 2
- IUWYBOFGGDTQOR-KHBPEBPSSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(CC1)OC=1C=CC=CC=1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(CC1)OC=1C=CC=CC=1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 IUWYBOFGGDTQOR-KHBPEBPSSA-N 0.000 claims 2
- YIBUSNKWAYXYIB-YSXIEMCBSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCCCCC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCCCCC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 YIBUSNKWAYXYIB-YSXIEMCBSA-N 0.000 claims 2
- NINQOJCMYBIHMF-KCFDPAHWSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCC(C)CC=1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCC(C)CC=1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 NINQOJCMYBIHMF-KCFDPAHWSA-N 0.000 claims 2
- PAMOIOVTAUVDIT-PWZZDWAZSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCC(CC=1)C=1C=CC=CC=1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCC(CC=1)C=1C=CC=CC=1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 PAMOIOVTAUVDIT-PWZZDWAZSA-N 0.000 claims 2
- USXOSXKMNUPPNO-JOSYPBKRSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCC2CCCCC2C=1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCC2CCCCC2C=1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 USXOSXKMNUPPNO-JOSYPBKRSA-N 0.000 claims 2
- VRCATWVIEHHTHZ-UAPYVXQJSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCCCC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCCCC1 VRCATWVIEHHTHZ-UAPYVXQJSA-N 0.000 claims 2
- MGIDOELNCIGRPO-IXXJFMHHSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@H]1CC[C@@H](O)CC1 MGIDOELNCIGRPO-IXXJFMHHSA-N 0.000 claims 2
- OUUFVRBISAEUNT-YSXIEMCBSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCCC=1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCCC=1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 OUUFVRBISAEUNT-YSXIEMCBSA-N 0.000 claims 2
- LNYKGELUODVSNS-URYRSFGFSA-N C1C[C@@H](OC)CC[C@@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)C1CCC(C)CC1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)C1CCC(C)CC1 LNYKGELUODVSNS-URYRSFGFSA-N 0.000 claims 2
- LNYKGELUODVSNS-YSXIEMCBSA-N C1C[C@@H](OC)CC[C@@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 LNYKGELUODVSNS-YSXIEMCBSA-N 0.000 claims 2
- 102000053642 Catalytic RNA Human genes 0.000 claims 2
- 108090000994 Catalytic RNA Proteins 0.000 claims 2
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims 2
- 108010036949 Cyclosporine Proteins 0.000 claims 2
- 229940121759 Helicase inhibitor Drugs 0.000 claims 2
- 102000006992 Interferon-alpha Human genes 0.000 claims 2
- 108010047761 Interferon-alpha Proteins 0.000 claims 2
- 102000013462 Interleukin-12 Human genes 0.000 claims 2
- 108010065805 Interleukin-12 Proteins 0.000 claims 2
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims 2
- 108091005804 Peptidases Proteins 0.000 claims 2
- 229940123066 Polymerase inhibitor Drugs 0.000 claims 2
- 239000004365 Protease Substances 0.000 claims 2
- 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 2
- 229940122055 Serine protease inhibitor Drugs 0.000 claims 2
- 101710102218 Serine protease inhibitor Proteins 0.000 claims 2
- 241000320380 Silybum Species 0.000 claims 2
- 235000010841 Silybum marianum Nutrition 0.000 claims 2
- 102000007501 Thymosin Human genes 0.000 claims 2
- 108010046075 Thymosin Proteins 0.000 claims 2
- 229960004308 acetylcysteine Drugs 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
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 230000000692 anti-sense effect Effects 0.000 claims 2
- 239000003963 antioxidant agent Substances 0.000 claims 2
- 230000003078 antioxidant effect Effects 0.000 claims 2
- 229960001265 ciclosporin Drugs 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 229930182912 cyclosporin Natural products 0.000 claims 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000002955 immunomodulating agent Substances 0.000 claims 2
- 229940121354 immunomodulator Drugs 0.000 claims 2
- 230000002584 immunomodulator Effects 0.000 claims 2
- 229940117681 interleukin-12 Drugs 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 239000002445 liver protective agent Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- LHKVDVFVJMYULK-UHFFFAOYSA-N nitrosylazide Chemical compound [N-]=[N+]=NN=O LHKVDVFVJMYULK-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 229960000329 ribavirin Drugs 0.000 claims 2
- 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 2
- 108091092562 ribozyme Proteins 0.000 claims 2
- 239000003001 serine protease inhibitor Substances 0.000 claims 2
- 229940021747 therapeutic vaccine Drugs 0.000 claims 2
- LCJVIYPJPCBWKS-NXPQJCNCSA-N thymosin Chemical compound SC[C@@H](N)C(=O)N[C@H](CO)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CO)C(=O)N[C@H](CO)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@H](CCC(O)=O)C(O)=O LCJVIYPJPCBWKS-NXPQJCNCSA-N 0.000 claims 2
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 1
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims 1
- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 claims 1
- RNEQXUALSHFBCE-UHFFFAOYSA-N 3-[(4-hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]-5-(4-oxocyclohexen-1-yl)thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1CCC(=O)CC=1)C(O)=O)C1CCC(O)CC1 RNEQXUALSHFBCE-UHFFFAOYSA-N 0.000 claims 1
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims 1
- AQBYCVVVNOZWPR-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[(1-formylpiperidin-4-yl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCN(C=O)CC1 AQBYCVVVNOZWPR-UHFFFAOYSA-N 0.000 claims 1
- AHQGMPPSKUDUDL-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[(4-fluorocyclohexyl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCC(F)CC1 AHQGMPPSKUDUDL-UHFFFAOYSA-N 0.000 claims 1
- YZBWRCKPMKZIKM-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[(4-methylcyclohexanecarbonyl)-[1-(2-methylpropanoyl)piperidin-4-yl]amino]thiophene-2-carboxylic acid Chemical compound C1CN(C(=O)C(C)C)CCC1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)C1CCC(C)CC1 YZBWRCKPMKZIKM-UHFFFAOYSA-N 0.000 claims 1
- CRTSWZNSWSTMNV-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[(4-methylcyclohexanecarbonyl)-[1-(pyridin-3-ylmethyl)piperidin-4-yl]amino]thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCN(CC=2C=NC=CC=2)CC1 CRTSWZNSWSTMNV-UHFFFAOYSA-N 0.000 claims 1
- KSKQKUXDUAQBNC-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[[4-[(1-methoxy-2-methylpropyl)carbamoyloxy]cyclohexyl]-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(OC(=O)NC(OC)C(C)C)CCC1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)C1CCC(C)CC1 KSKQKUXDUAQBNC-UHFFFAOYSA-N 0.000 claims 1
- PFOHWPCBSUQTAS-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-3-[[4-[(1-methoxy-3-methyl-1-oxobutan-2-yl)carbamoyloxy]cyclohexyl]-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(OC(=O)NC(C(=O)OC)C(C)C)CCC1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)C1CCC(C)CC1 PFOHWPCBSUQTAS-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- GVYKMIALDJEPRQ-CPONINCNSA-N C1=C(C=2CCC(C)CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)[C@H]1CC[C@H](C)CC1 Chemical compound C1=C(C=2CCC(C)CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)[C@H]1CC[C@H](C)CC1 GVYKMIALDJEPRQ-CPONINCNSA-N 0.000 claims 1
- OHWPNFAZTZGNKZ-SAABIXHNSA-N C1=C(C=2CCCCC=2)SC(C(O)=O)=C1N(C(COC)COC)C(=O)[C@H]1CC[C@H](C)CC1 Chemical compound C1=C(C=2CCCCC=2)SC(C(O)=O)=C1N(C(COC)COC)C(=O)[C@H]1CC[C@H](C)CC1 OHWPNFAZTZGNKZ-SAABIXHNSA-N 0.000 claims 1
- XSKWKTVUQVYCKD-NHZVSXMUSA-N C1C(=N/OCC)\CCC(C=2SC(=C(N([C@@H]3CC[C@@H](O)CC3)C(=O)[C@@H]3CC[C@@H](C)CC3)C=2)C(O)=O)=C1 Chemical compound C1C(=N/OCC)\CCC(C=2SC(=C(N([C@@H]3CC[C@@H](O)CC3)C(=O)[C@@H]3CC[C@@H](C)CC3)C=2)C(O)=O)=C1 XSKWKTVUQVYCKD-NHZVSXMUSA-N 0.000 claims 1
- TVNILQLSTHSMLT-ZCYMVKBSSA-N C1CC(=NOCC)CCC1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 Chemical compound C1CC(=NOCC)CCC1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 TVNILQLSTHSMLT-ZCYMVKBSSA-N 0.000 claims 1
- UKRVVPIKBGFVNT-RPCDJPHFSA-N C1CC(N(C)C(=O)CC)CCC1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 Chemical compound C1CC(N(C)C(=O)CC)CCC1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 UKRVVPIKBGFVNT-RPCDJPHFSA-N 0.000 claims 1
- YBQKQVZAEDDNAU-CTYIDZIISA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C)C1=C(C(O)=O)SC(C=2CCCCC=2)=C1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C)C1=C(C(O)=O)SC(C=2CCCCC=2)=C1 YBQKQVZAEDDNAU-CTYIDZIISA-N 0.000 claims 1
- AIPXYNJQICQCPP-QFLLTADKSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1C2CCC(C2)C1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1C2CCC(C2)C1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 AIPXYNJQICQCPP-QFLLTADKSA-N 0.000 claims 1
- JFNVYOKGZLDNAH-KQEUCTNFSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CC=CCC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CC=CCC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 JFNVYOKGZLDNAH-KQEUCTNFSA-N 0.000 claims 1
- MMKZHFVOWJFVHI-KESTWPANSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)C1CCN(C)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)C1CCN(C)CC1 MMKZHFVOWJFVHI-KESTWPANSA-N 0.000 claims 1
- VSBSZSMJLXBCCV-SAABIXHNSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)C1COCOC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)C1COCOC1 VSBSZSMJLXBCCV-SAABIXHNSA-N 0.000 claims 1
- UUEBOGSQUVQIEE-YSXIEMCBSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)[C@@H]1CC[C@@H](F)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)[C@@H]1CC[C@@H](F)CC1 UUEBOGSQUVQIEE-YSXIEMCBSA-N 0.000 claims 1
- URPYXASENBMACD-GUJRETQESA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)[C@@H]1CC[C@@H](N2N=CN=C2)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)[C@@H]1CC[C@@H](N2N=CN=C2)CC1 URPYXASENBMACD-GUJRETQESA-N 0.000 claims 1
- GTZZCRIWNBVETM-GUJRETQESA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)[C@@H]1CC[C@@H](N2N=NC=C2)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)[C@@H]1CC[C@@H](N2N=NC=C2)CC1 GTZZCRIWNBVETM-GUJRETQESA-N 0.000 claims 1
- DRTQOSFDYDDNNA-YSXIEMCBSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 DRTQOSFDYDDNNA-YSXIEMCBSA-N 0.000 claims 1
- URPYXASENBMACD-FORLXOICSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)[C@@H]1CC[C@H](N2N=CN=C2)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)[C@@H]1CC[C@H](N2N=CN=C2)CC1 URPYXASENBMACD-FORLXOICSA-N 0.000 claims 1
- UFAKXAOJOPWWCD-GUJRETQESA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCC(C)(C)CC=1)C(O)=O)[C@@H]1CC[C@@H](N2N=CN=C2)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCC(C)(C)CC=1)C(O)=O)[C@@H]1CC[C@@H](N2N=CN=C2)CC1 UFAKXAOJOPWWCD-GUJRETQESA-N 0.000 claims 1
- XMHTZCKCUJIEIC-PPFQCUIHSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CC(C)CCC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CC(C)CCC1 XMHTZCKCUJIEIC-PPFQCUIHSA-N 0.000 claims 1
- QMKHTEOIBBSGKN-WHLIJDCNSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CC(C2)CCC2C1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CC(C2)CCC2C1 QMKHTEOIBBSGKN-WHLIJDCNSA-N 0.000 claims 1
- DTJARGIYIUHGII-KOMQPUFPSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CC1 DTJARGIYIUHGII-KOMQPUFPSA-N 0.000 claims 1
- CRLPSZXQCTYECG-KESTWPANSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCC(C)(C)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCC(C)(C)CC1 CRLPSZXQCTYECG-KESTWPANSA-N 0.000 claims 1
- OSJUSKYSFLVNJA-SAABIXHNSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCC(F)(F)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCC(F)(F)CC1 OSJUSKYSFLVNJA-SAABIXHNSA-N 0.000 claims 1
- HWWJOYSOQMFTFU-LMKRUTEGSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCC(OC(=O)N2CCOCC2)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCC(OC(=O)N2CCOCC2)CC1 HWWJOYSOQMFTFU-LMKRUTEGSA-N 0.000 claims 1
- QMPSPZPLWQPLNV-UAPYVXQJSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCN(CC(F)F)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCN(CC(F)F)CC1 QMPSPZPLWQPLNV-UAPYVXQJSA-N 0.000 claims 1
- AHIZAJIZSMUYKS-KESTWPANSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCN(CCF)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCN(CCF)CC1 AHIZAJIZSMUYKS-KESTWPANSA-N 0.000 claims 1
- NTQRCGGRNOJNJD-UAPYVXQJSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCN(S(C)(=O)=O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCN(S(C)(=O)=O)CC1 NTQRCGGRNOJNJD-UAPYVXQJSA-N 0.000 claims 1
- QJEOKVNLHVLDLL-SAABIXHNSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCOCC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCOCC1 QJEOKVNLHVLDLL-SAABIXHNSA-N 0.000 claims 1
- CEQRAOMBFIAWLT-SAABIXHNSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCSCC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1CCSCC1 CEQRAOMBFIAWLT-SAABIXHNSA-N 0.000 claims 1
- BWWCLVQZCHIZEF-BOYKGFJRSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1COC(C)OC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C1COC(C)OC1 BWWCLVQZCHIZEF-BOYKGFJRSA-N 0.000 claims 1
- SATLBJQBKFNRNL-VYUAXZJKSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@@H]1CC[C@@H](C#N)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@@H]1CC[C@@H](C#N)CC1 SATLBJQBKFNRNL-VYUAXZJKSA-N 0.000 claims 1
- KCFLNRBBFVETGB-VJVRBHMKSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@@H]1CC[C@@H](C=2NN=NN=2)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@@H]1CC[C@@H](C=2NN=NN=2)CC1 KCFLNRBBFVETGB-VJVRBHMKSA-N 0.000 claims 1
- AHQGMPPSKUDUDL-VJVRBHMKSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@@H]1CC[C@@H](F)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@@H]1CC[C@@H](F)CC1 AHQGMPPSKUDUDL-VJVRBHMKSA-N 0.000 claims 1
- BZOWKCOXOYJPPR-XHPGVBHPSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@@H]1CC[C@@H](N2N=NC=C2)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@@H]1CC[C@@H](N2N=NC=C2)CC1 BZOWKCOXOYJPPR-XHPGVBHPSA-N 0.000 claims 1
- QPTQPRHLMQYGHB-ZULOPVSISA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@@H]1CC[C@H](N2N=CN=C2)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@@H]1CC[C@H](N2N=CN=C2)CC1 QPTQPRHLMQYGHB-ZULOPVSISA-N 0.000 claims 1
- BZOWKCOXOYJPPR-ZULOPVSISA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@@H]1CC[C@H](N2N=NC=C2)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)[C@@H]1CC[C@H](N2N=NC=C2)CC1 BZOWKCOXOYJPPR-ZULOPVSISA-N 0.000 claims 1
- BVXHTXRVCMTCJW-XBFADQFBSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)[C@@H]1CC[C@@H](C)CC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)[C@@H]1CC[C@@H](C)CC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 BVXHTXRVCMTCJW-XBFADQFBSA-N 0.000 claims 1
- BVXHTXRVCMTCJW-GONJQHFYSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)[C@H]1CC[C@@H](C)CC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(=C1)[C@H]1CC[C@@H](C)CC1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 BVXHTXRVCMTCJW-GONJQHFYSA-N 0.000 claims 1
- LBFROQIFJOYWFA-HDRKRICHSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(Br)=C1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C1=C(SC(Br)=C1)C(O)=O)[C@@H]1CC[C@@H](O)CC1 LBFROQIFJOYWFA-HDRKRICHSA-N 0.000 claims 1
- VNDXSTNPMCDMEN-SAABIXHNSA-N C1C[C@@H](C)CC[C@@H]1C(=O)N(C=1C=C2OCOC2=CC=1)C1=C(C(O)=O)SC(C=2CCCCC=2)=C1 Chemical compound C1C[C@@H](C)CC[C@@H]1C(=O)N(C=1C=C2OCOC2=CC=1)C1=C(C(O)=O)SC(C=2CCCCC=2)=C1 VNDXSTNPMCDMEN-SAABIXHNSA-N 0.000 claims 1
- XLJOUVDPWPSXDM-VYUAXZJKSA-N C1C[C@@H](C)CC[C@@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 Chemical compound C1C[C@@H](C)CC[C@@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 XLJOUVDPWPSXDM-VYUAXZJKSA-N 0.000 claims 1
- XLJOUVDPWPSXDM-ICNBMTIMSA-N C1C[C@@H](C)CC[C@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 Chemical compound C1C[C@@H](C)CC[C@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 XLJOUVDPWPSXDM-ICNBMTIMSA-N 0.000 claims 1
- OVTIYPJPKHHYCK-GUJRETQESA-N C1C[C@@H](NC(=O)C(C)C)CC[C@@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 Chemical compound C1C[C@@H](NC(=O)C(C)C)CC[C@@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 OVTIYPJPKHHYCK-GUJRETQESA-N 0.000 claims 1
- QOIHGTCVBFQWJO-DRLVJGDXSA-N C1C[C@@H](OC)CC[C@@H]1N(C1=C(SC(=C1)C1CCC(CC1)C(F)(F)F)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N(C1=C(SC(=C1)C1CCC(CC1)C(F)(F)F)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 QOIHGTCVBFQWJO-DRLVJGDXSA-N 0.000 claims 1
- JFUHFSBVZUPBIF-IKYFGSHTSA-N C1C[C@@H](OC)CC[C@@H]1N(C1=C(SC(=C1)C=1CCC(CC=1)C(F)(F)F)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N(C1=C(SC(=C1)C=1CCC(CC=1)C(F)(F)F)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 JFUHFSBVZUPBIF-IKYFGSHTSA-N 0.000 claims 1
- GZPCNCMYPJUFCL-BIAGXBKMSA-N C1C[C@@H](OC)CC[C@@H]1N(C1=C(SC=C1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N(C1=C(SC=C1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 GZPCNCMYPJUFCL-BIAGXBKMSA-N 0.000 claims 1
- AMOXNTAMLUCWJT-ZULOPVSISA-N C1C[C@@H](OC)CC[C@H]1N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 Chemical compound C1C[C@@H](OC)CC[C@H]1N(C1=C(SC(=C1)C1CCC(C)(C)CC1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 AMOXNTAMLUCWJT-ZULOPVSISA-N 0.000 claims 1
- LNYKGELUODVSNS-HMYFDTNDSA-N C1C[C@@H](OC)CC[C@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)C1CCC(C)CC1 Chemical compound C1C[C@@H](OC)CC[C@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)C1CCC(C)CC1 LNYKGELUODVSNS-HMYFDTNDSA-N 0.000 claims 1
- ARGZTWUXBRUFQC-GUJRETQESA-N C1C[C@@H](OCOCC)CC[C@@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 Chemical compound C1C[C@@H](OCOCC)CC[C@@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 ARGZTWUXBRUFQC-GUJRETQESA-N 0.000 claims 1
- YUIXIDHCLFDQRR-XHPGVBHPSA-N C1C[C@@H](OCSC)CC[C@@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 Chemical compound C1C[C@@H](OCSC)CC[C@@H]1N(C1=C(SC(=C1)C=1CCCCC=1)C(O)=O)C(=O)[C@@H]1CC[C@@H](C)CC1 YUIXIDHCLFDQRR-XHPGVBHPSA-N 0.000 claims 1
- CYJOSVWUGBXIKT-KESTWPANSA-N C[C@H](CC1)CC[C@@H]1C(N(C1CCN(C)CC1)C1=C(C(OC)=O)SC(C2=CCCCC2)=C1)=O Chemical compound C[C@H](CC1)CC[C@@H]1C(N(C1CCN(C)CC1)C1=C(C(OC)=O)SC(C2=CCCCC2)=C1)=O CYJOSVWUGBXIKT-KESTWPANSA-N 0.000 claims 1
- QVBYCKAQILQSKF-KESTWPANSA-N C[C@H](CC1)CC[C@@H]1C(N(C1CC[N+](C)(C)CC1)C1=C(C([O-])=O)SC(C2=CCCCC2)=C1)=O Chemical compound C[C@H](CC1)CC[C@@H]1C(N(C1CC[N+](C)(C)CC1)C1=C(C([O-])=O)SC(C2=CCCCC2)=C1)=O QVBYCKAQILQSKF-KESTWPANSA-N 0.000 claims 1
- ODWKZJPLPDNWCA-FLISKEQISA-N C[C@H](CC1)CC[C@@H]1C(N([C@H](CC1)CC[C@@H]1OC)C1=C(C(O)=O)SC(C2CCC(C)(C)CC2)=C1)=O.NCCCC[C@@H](C(O)=O)N Chemical compound C[C@H](CC1)CC[C@@H]1C(N([C@H](CC1)CC[C@@H]1OC)C1=C(C(O)=O)SC(C2CCC(C)(C)CC2)=C1)=O.NCCCC[C@@H](C(O)=O)N ODWKZJPLPDNWCA-FLISKEQISA-N 0.000 claims 1
- REUHTKWWZIGQAT-FMMATFHQSA-M C[C@H](CC1)CC[C@@H]1C(N([C@H](CC1)CC[C@@H]1OC)C1=C(C([O-])=O)SC(C2CCC(C)(C)CC2)=C1)=O.C[N+](C)(C)CCO Chemical compound C[C@H](CC1)CC[C@@H]1C(N([C@H](CC1)CC[C@@H]1OC)C1=C(C([O-])=O)SC(C2CCC(C)(C)CC2)=C1)=O.C[N+](C)(C)CCO REUHTKWWZIGQAT-FMMATFHQSA-M 0.000 claims 1
- 102000035195 Peptidases Human genes 0.000 claims 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 1
- HLLIYDVPIGSIJX-AFFTWYSYSA-N [Cl-].CC(C)OC(=O)OCOC(=O)C=1SC(C=2CCCCC=2)=CC=1N(C(=O)[C@@H]1CC[C@@H](C)CC1)C1CC[NH+](C)CC1 Chemical compound [Cl-].CC(C)OC(=O)OCOC(=O)C=1SC(C=2CCCCC=2)=CC=1N(C(=O)[C@@H]1CC[C@@H](C)CC1)C1CC[NH+](C)CC1 HLLIYDVPIGSIJX-AFFTWYSYSA-N 0.000 claims 1
- 125000003725 azepanyl group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004069 aziridinyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims 1
- 125000004113 cyclononanyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004090 cyclononenyl group Chemical group C1(=CCCCCCCC1)* 0.000 claims 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 1
- 125000004188 dichlorophenyl group Chemical group 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68048205P | 2005-05-13 | 2005-05-13 | |
| US60/680,482 | 2005-05-13 | ||
| PCT/CA2006/000786 WO2006119646A1 (en) | 2005-05-13 | 2006-05-15 | Compounds and methods for the treatment or prevention of flavivirus infections |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008540463A JP2008540463A (ja) | 2008-11-20 |
| JP2008540463A5 true JP2008540463A5 (https=) | 2009-07-02 |
| JP5030947B2 JP5030947B2 (ja) | 2012-09-19 |
Family
ID=37396165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008510379A Expired - Fee Related JP5030947B2 (ja) | 2005-05-13 | 2006-05-15 | フラビウイルス感染の治療及び予防のための化合物及び方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US7569600B2 (https=) |
| EP (3) | EP1879879B1 (https=) |
| JP (1) | JP5030947B2 (https=) |
| KR (1) | KR20080016597A (https=) |
| CN (2) | CN101218224B (https=) |
| AP (1) | AP2007004245A0 (https=) |
| AU (1) | AU2006246227B2 (https=) |
| BR (1) | BRPI0610283A2 (https=) |
| CA (1) | CA2607359C (https=) |
| EA (1) | EA016071B1 (https=) |
| ES (1) | ES2415742T3 (https=) |
| MX (1) | MX2007014117A (https=) |
| NZ (1) | NZ563909A (https=) |
| SG (1) | SG161315A1 (https=) |
| WO (1) | WO2006119646A1 (https=) |
| ZA (1) | ZA200709727B (https=) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8329924B2 (en) * | 2001-06-11 | 2012-12-11 | Vertex Pharmaceuticals (Canada) Incorporated | Compounds and methods for the treatment or prevention of Flavivirus infections |
| CN101624391A (zh) * | 2001-06-11 | 2010-01-13 | 病毒化学医药公司 | 用作黄病毒感染抗病毒剂的噻吩衍生物 |
| BRPI0610283A2 (pt) * | 2005-05-13 | 2010-10-19 | Virochem Pharma Inc | composto, uso do mesmo na preparação de um medicamento para o tratamento ou prevenção de uma infecção por vìrus de hepatite c, composição farmacêutica e combinação farmacêutica |
| CA2670260A1 (en) | 2006-11-15 | 2008-05-22 | Virochem Pharma Inc. | Thiophene analogues for the treatment or prevention of flavivirus infections |
| JP2010521457A (ja) * | 2007-03-12 | 2010-06-24 | メルク・シャープ・エンド・ドーム・コーポレイション | 単環式アニリドスピロラクタムｃｇｒｐ受容体アンタゴニスト |
| DK2308514T3 (da) | 2007-03-23 | 2013-09-02 | To Bbb Holding B V | Konjugater til målrettet lægemiddeltransport gennem blod-hjerne barrieren |
| ES2381410T3 (es) | 2007-05-04 | 2012-05-28 | Vertex Pharmceuticals Incorporated | Terapia de combinación paa el tratamiento de infecciones por VHC |
| JP2010528051A (ja) | 2007-05-23 | 2010-08-19 | シガ・テクノロジーズ・インコーポレーテッド | デング感染症の治療または予防のための抗ウイルス薬 |
| GB0712393D0 (en) * | 2007-06-26 | 2007-08-01 | Smithkline Beecham Corp | Compounds |
| EP2234977A4 (en) | 2007-12-19 | 2011-04-13 | Boehringer Ingelheim Int | VIRAL POLYMERASE INHIBITORS |
| US20110212986A1 (en) * | 2008-08-21 | 2011-09-01 | Health Research, Inc. | Anti-flavivirus therapeutic |
| CN102271699A (zh) | 2009-01-07 | 2011-12-07 | 西尼克斯公司 | 用于治疗hcv和hiv感染的环孢菌素衍生物 |
| JP5327744B2 (ja) * | 2009-03-13 | 2013-10-30 | 国立大学法人 鹿児島大学 | ジフェニルメタン誘導体を有効成分とする抗ウイルス剤 |
| WO2011011303A1 (en) * | 2009-07-21 | 2011-01-27 | Gilead Sciences, Inc. | Inhibitors of flaviviridae viruses |
| ES2559437T3 (es) | 2009-09-09 | 2016-02-12 | Gilead Sciences, Inc. | Inhibidores de virus de la familia Flaviviridae |
| WO2011034962A2 (en) * | 2009-09-16 | 2011-03-24 | Calcimedica Inc. | Compounds that modulate intracellular calcium |
| JP2013512247A (ja) | 2009-11-25 | 2013-04-11 | バーテックス ファーマシューティカルズ インコーポレイテッド | フラビウイルス感染症の治療または予防のための５−アルキニル−チオフェン−２−カルボン酸誘導体およびそれらの使用 |
| CA2785563C (en) | 2010-01-15 | 2019-05-14 | Gilead Sciences, Inc. | Inhibitors of flaviviridae viruses |
| AP3576A (en) | 2010-01-15 | 2016-02-08 | Gilead Sciences Inc | Inhibitors of flaviviridae viruses |
| AU2011276526A1 (en) | 2010-06-28 | 2013-01-10 | Vertex Pharmaceuticals Incorporated | Compounds and methods for the treatment or prevention of Flavivirus infections |
| EP2585448A1 (en) * | 2010-06-28 | 2013-05-01 | Vertex Pharmaceuticals Incorporated | Compounds and methods for the treatment or prevention of flavivirus infections |
| AU2011292040A1 (en) | 2010-08-17 | 2013-03-07 | Vertex Pharmaceuticals Incorporated | Compounds and methods for the treatment or prevention of Flaviviridae viral infections |
| EP2651906A4 (en) | 2010-12-17 | 2014-06-25 | Cocrystal Discovery Inc | INHIBITORS OF HEPATITIS C VIRUS POLYMERASE |
| US20130203706A1 (en) * | 2011-06-28 | 2013-08-08 | Vertex Pharmaceuticals Incorporated | Compounds and methods for the treatment or prevention of flavivirus infections |
| AU2012280959B2 (en) * | 2011-07-13 | 2015-08-06 | Gilead Sciences, Inc. | Thiophen-2-carboxylic acid derivatives useful as inhibitors of Flaviviridae viruses |
| CN103059042B (zh) * | 2011-10-18 | 2015-10-07 | 银杏树药业(苏州)有限公司 | 噻吩类衍生物及其在药学中的用途 |
| US8466159B2 (en) | 2011-10-21 | 2013-06-18 | Abbvie Inc. | Methods for treating HCV |
| SE1450131A1 (sv) | 2011-10-21 | 2014-05-07 | Abbvie Inc | DAA-kombinationsbehandling (t.ex. med ABT-072 eller ABT-333)för användning vid behandling av HCV |
| US8492386B2 (en) | 2011-10-21 | 2013-07-23 | Abbvie Inc. | Methods for treating HCV |
| DE112012002748T5 (de) | 2011-10-21 | 2014-07-31 | Abbvie Inc. | Verfahren zur Behandlung von HCV umfassend mindestens zwei direkt wirkende antivirale Wirkstoffe, Ribavirin aber nicht Interferon |
| CN103087052A (zh) * | 2011-10-31 | 2013-05-08 | 上海壹志医药科技有限公司 | 噻吩衍生物及其药物用途 |
| WO2014055142A1 (en) | 2012-06-20 | 2014-04-10 | Cocrystal Discovery, Inc. | Inhibitors of hepatitis c virus polymerase |
| US8927741B2 (en) | 2012-08-17 | 2015-01-06 | Gilead Sciences, Inc. | Synthesis of an antiviral compound |
| US8759544B2 (en) | 2012-08-17 | 2014-06-24 | Gilead Sciences, Inc. | Synthesis of an antiviral compound |
| US8841340B2 (en) | 2012-08-17 | 2014-09-23 | Gilead Sciences, Inc. | Solid forms of an antiviral compound |
| TWI731854B (zh) | 2015-03-23 | 2021-07-01 | 美商共結晶製藥公司 | Ｃ型肝炎病毒聚合酶之抑制劑 |
| EA201892448A1 (ru) | 2016-04-28 | 2019-06-28 | Эмори Юниверсити | Алкинсодержащие нуклеотидные и нуклеозидные терапевтические композиции и связанные с ними способы применения |
| CN106467477A (zh) * | 2016-08-26 | 2017-03-01 | 天津雅奥科技发展有限公司 | 一种合成化合物（1‑环丙基‑1‑氰基‑4‑环己酮）的新方法 |
| MX2020011912A (es) | 2018-05-09 | 2021-01-29 | Cocrystal Pharma Inc | Terapia de combinacion para el tratamiento del virus de la hepatitis c (vhc). |
| BR112020025696A2 (pt) | 2018-06-19 | 2021-03-16 | Novartis Ag | Derivados de tetra-hidrotienopiridina n-substituída e usos dos mesmos |
| CN110592172B (zh) * | 2019-10-29 | 2021-05-28 | 华中农业大学 | 利用CRISPR/Cas9敲除文库技术筛选JEV抗性基因的方法与靶点 |
| CN111518015A (zh) * | 2020-05-20 | 2020-08-11 | 上海合全药物研发有限公司 | 一种叔丁基-8-氧亚基-2-氮杂螺[4.5]癸烷-2-甲酸基酯的制备方法 |
| CN113861176B (zh) * | 2021-09-28 | 2023-11-03 | 北京凯因格领生物技术有限公司 | 一种黄病毒抑制剂 |
| EP4282862A1 (en) * | 2022-05-25 | 2023-11-29 | Irbm S.P.A. | Flavivirus inhibitors |
| KR20260032992A (ko) * | 2023-06-05 | 2026-03-10 | 셀로람 인코포레이티드 | 지방산 결합 단백질(fabps) 억제제, 그 사용 방법, 및 제조 방법 |
Family Cites Families (92)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3076817A (en) * | 1963-02-05 | New j-amino-thiophene-z | ||
| DE1055007B (de) | 1957-08-29 | 1959-04-16 | Dr Hans Fiesselmann | Verfahren zur Herstellung von 3-Aminothiophen-2-carbonsaeureestern und den entsprechenden freien Carbonsaeuren |
| US3470151A (en) | 1966-05-17 | 1969-09-30 | Beecham Group Ltd | Furyl- and thienyl-penicillins and salts thereof |
| AU518216B2 (en) * | 1977-09-06 | 1981-09-17 | Hafslund Nycomed Pharma Aktiengesellschaft | Thienothiazine derivatives |
| GB8627698D0 (en) | 1986-11-20 | 1986-12-17 | Boots Co Plc | Therapeutic agents |
| US4962101A (en) | 1989-08-21 | 1990-10-09 | Merck & Co., Inc. | 2-(Heterocyclylalkyl)phenyl carbapenem antibacterial agents |
| JPH0748360A (ja) | 1993-05-31 | 1995-02-21 | Yoshitomi Pharmaceut Ind Ltd | ビフェニルテトラゾール誘導体 |
| AP1019A (en) | 1996-10-18 | 2001-10-16 | Vertex Pharma | Inhibitors of serinre proteases, particularly hepatitis C virus NS3 protease. |
| JP4000608B2 (ja) * | 1996-11-07 | 2007-10-31 | トヨタ自動車株式会社 | 水素製造充填装置および電気自動車 |
| TW523506B (en) * | 1996-12-18 | 2003-03-11 | Ono Pharmaceutical Co | Sulfonamide or carbamide derivatives and drugs containing the same as active ingredients |
| US6117911A (en) * | 1997-04-11 | 2000-09-12 | Neorx Corporation | Compounds and therapies for the prevention of vascular and non-vascular pathologies |
| AP9901643A0 (en) * | 1997-04-28 | 1999-10-02 | Texas Biotechnology Corp | Sulfonamides for treatment of endothelin-mediated disorders. |
| US5783705A (en) * | 1997-04-28 | 1998-07-21 | Texas Biotechnology Corporation | Process of preparing alkali metal salys of hydrophobic sulfonamides |
| ATE399007T1 (de) | 1997-05-23 | 2008-07-15 | Bayer Pharmaceuticals Corp | Raf kinase hemmer |
| WO1998052558A1 (en) | 1997-05-23 | 1998-11-26 | Bayer Corporation | INHIBITION OF p38 KINASE ACTIVITY BY ARYL UREAS |
| US6187799B1 (en) * | 1997-05-23 | 2001-02-13 | Onyx Pharmaceuticals | Inhibition of raf kinase activity using aryl ureas |
| EP1012180B1 (en) | 1997-08-11 | 2004-12-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor peptide analogues |
| ES2241157T3 (es) | 1997-08-11 | 2005-10-16 | Boehringer Ingelheim (Canada) Ltd. | Peptidos inhibidores de la hepatitis c. |
| ATE228119T1 (de) | 1998-04-15 | 2002-12-15 | Pfizer Prod Inc | Heterocyclische carboxamide |
| EP0960882A1 (en) * | 1998-05-19 | 1999-12-01 | Hoechst Marion Roussel Deutschland GmbH | Thienyl substituted acylguanidines as inhibitors of bone resorption and vitronectin receptor antagonists |
| US6858223B2 (en) * | 1998-06-23 | 2005-02-22 | Altana Pharma Ag | Compositions comprising phenylaminothiophenacetic acid derivatives for the treatment of acute or adult respiratory distress syndrome (ARDS) and infant respiratory distress syndrome (IRDS) |
| AU4385399A (en) * | 1998-06-29 | 2000-01-17 | Biochem Pharma Inc. | Thiophene and furan 2,5-dicarboxamides useful in the treatment of cancer |
| AU756627B2 (en) | 1998-07-27 | 2003-01-16 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Diketoacid-derivatives as inhibitors of polymerases |
| 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 |
| ATE291423T1 (de) | 1998-08-20 | 2005-04-15 | Agouron Pharma | Nicht-peptidische gnrh agentia, verfahren und zwischenverbindungen zur ihren herstellung |
| DE19903398A1 (de) | 1999-01-29 | 2000-08-10 | Hassan Jomaa | Verwendung von Thiadiazolderivaten zur prophylaktischen und therapeutischen Behandlung von Infektionen |
| NZ528846A (en) * | 1999-03-12 | 2005-05-27 | Boehringer Ingelheim Pharma | Compounds useful as anti-inflammatory agents |
| 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 |
| JP2001010957A (ja) | 1999-04-28 | 2001-01-16 | Sankyo Co Ltd | 肝障害の予防または抑制剤 |
| DE19920247A1 (de) | 1999-05-03 | 2000-11-16 | Hassan Jomaa | Arzneimittel mit einem Gehalt an Verbindungen mit einem Stickstoff-Sauerstoff-Heterocyclus als Wirkstoff und ihre Verwendung |
| HN2000000051A (es) * | 1999-05-19 | 2001-02-02 | Pfizer Prod Inc | Derivados heterociclicos utiles como agentes anticancerosos |
| CA2385972A1 (en) * | 1999-10-01 | 2001-04-12 | Haruhisa Ogita | Novel diarylamide derivatives and use thereof as medicines |
| KR20020058046A (ko) * | 1999-11-29 | 2002-07-12 | 한스 루돌프 하우스, 헨리테 브룬너, 베아트리체 귄터 | 살충성 ｎ-헤테로아릴 알파-알콕시미노-카르복사미드 |
| EP1162196A4 (en) | 1999-12-27 | 2003-04-16 | Japan Tobacco Inc | COMPOUNDS WITH JOINED CYCLES AND THEIR USE AS MEDICAMENTS |
| DE10002424A1 (de) * | 2000-01-20 | 2001-07-26 | Siemens Ag | Di(het)arylaminothiophen-Derivate |
| US20040034041A1 (en) | 2000-05-10 | 2004-02-19 | Dashyant Dhanak | Novel anti-infectives |
| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| US6414013B1 (en) * | 2000-06-19 | 2002-07-02 | Pharmacia & Upjohn S.P.A. | Thiophene compounds, process for preparing the same, and pharmaceutical compositions containing the same background of the invention |
| GB0017676D0 (en) | 2000-07-19 | 2000-09-06 | Angeletti P Ist Richerche Bio | Inhibitors of viral polymerase |
| SV2003000617A (es) | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| AU2002213048A1 (en) | 2000-10-05 | 2002-04-15 | Smith Kline Beecham Corporation | Phosphate transport inhibitors |
| ES2271109T3 (es) | 2000-11-08 | 2007-04-16 | Syngenta Participations Ag | Pirrocarboxamidas y pirrolcarbotioamidas y sus usos agroquimicos. |
| ES2263687T3 (es) | 2000-11-20 | 2006-12-16 | Bristol-Myers Squibb Company | Inhibidores tripeptidicos de la hepatitis c. |
| US6892279B2 (en) * | 2000-11-30 | 2005-05-10 | Mosaid Technologies Incorporated | Method and apparatus for accelerating retrieval of data from a memory system with cache by reducing latency |
| DE10061876A1 (de) * | 2000-12-12 | 2002-06-20 | Aventis Pharma Gmbh | Arylierte Furan- und Thiophencarbonsäureamide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| WO2002057425A2 (en) | 2001-01-22 | 2002-07-25 | Merck & Co., Inc. | Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase |
| AU2002252183A1 (en) | 2001-03-06 | 2002-09-19 | Biocryst Pharmaceuticals, Inc. | Nucleosides, preparation thereof and use as inhibitors of rna viral polymerases |
| US6734207B2 (en) * | 2001-04-20 | 2004-05-11 | Parker Hughes Institute | Cytotoxic compounds |
| EP1256628A3 (en) | 2001-05-10 | 2003-03-19 | Agouron Pharmaceuticals, Inc. | Hepatitis c virus (hcv) ns5b rna polymerase and mutants thereof |
| US6713638B2 (en) * | 2001-05-18 | 2004-03-30 | Joel M. Linden | 2-amino-3-aroyl-4,5 alkylthiophenes: agonist allosteric enhancers at human A1 adenosine receptors |
| AR036081A1 (es) | 2001-06-07 | 2004-08-11 | Smithkline Beecham Corp | Compuesto de 1,2-dihidroquinolina, su uso para preparar una composicion farmaceutica, metodos para prepararlo y compuestos del acido 2-aminobenzoico n-alquilado de utilidad como intermediarios en dichos metodos |
| CN101624391A (zh) * | 2001-06-11 | 2010-01-13 | 病毒化学医药公司 | 用作黄病毒感染抗病毒剂的噻吩衍生物 |
| US6887877B2 (en) * | 2001-06-11 | 2005-05-03 | Virochem Pharma Inc. | Compounds and methods for the treatment or prevention of Flavivirus infections |
| AR035543A1 (es) | 2001-06-26 | 2004-06-16 | Japan Tobacco Inc | Agente terapeutico para la hepatitis c que comprende un compuesto de anillo condensado, compuesto de anillo condensado, composicion farmaceutica que lo comprende, compuestos de benzimidazol, tiazol y bifenilo utiles como intermediarios para producir dichos compuestos, uso del compuesto de anillo con |
| EP2335700A1 (en) | 2001-07-25 | 2011-06-22 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis C virus polymerase inhibitors with a heterobicylic structure |
| SE0102617D0 (sv) * | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
| WO2003026587A2 (en) | 2001-09-26 | 2003-04-03 | Bristol-Myers Squibb Company | Compounds useful for treating hepatitus c virus |
| DE60229975D1 (de) * | 2001-10-04 | 2009-01-02 | Smithkline Beecham Corp | Nf-kb-inhibitoren |
| AU2002348414B2 (en) | 2001-10-24 | 2009-10-01 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine protease, particularly hepatitis C virus NS3-NS4A protease, incorporating a fused ring system |
| TWI281916B (en) * | 2001-10-25 | 2007-06-01 | Lilly Co Eli | Antitumor compounds and methods |
| WO2003055479A1 (en) * | 2001-12-21 | 2003-07-10 | Consejo Superior De Investigaciones Cientificas | Compounds and their therapeutic use related to the phosphorylating activity of the enzyme gsk-3 |
| US6835745B2 (en) * | 2002-01-15 | 2004-12-28 | Wyeth | Phenyl substituted thiophenes as estrogenic agents |
| DE10203122A1 (de) | 2002-01-25 | 2003-07-31 | Gruenenthal Gmbh | Verfahren zur Herstellung von substituierten Acrylsäureestern bzw. deren Einsatz zur Herstellung von substituierten gamma-Aminosäuren |
| AU2003223602B8 (en) | 2002-04-11 | 2010-05-27 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hepatitis C virus NS3-NS4 protease |
| AU2003232071A1 (en) | 2002-05-06 | 2003-11-17 | Genelabs Technologies, Inc. | Nucleoside derivatives for treating hepatitis c virus infection |
| HRP20041220A2 (hr) * | 2002-05-28 | 2006-04-30 | 3-Dimensional Pharmaceuticals | Novi tiofen amidini, njihovi pripravci i postupci liječenja komplementom posredovanih bolesti i stanja |
| US7179836B2 (en) * | 2002-09-20 | 2007-02-20 | Smithkline Beecham Corporation | Chemical compounds |
| JP4926403B2 (ja) * | 2002-12-10 | 2012-05-09 | ヴァイロケム ファーマ インコーポレイテッド | フラビウイルス感染の処置もしくは予防のための化合物および方法 |
| AU2003291886A1 (en) | 2002-12-10 | 2004-06-30 | Virochem Pharma Inc. | Thiophenederivatives for the treatment of flavivirus infections |
| US7402608B2 (en) | 2002-12-10 | 2008-07-22 | Virochem Pharma Inc. | Compounds and methods for the treatment or prevention of Flavivirus infections |
| US7098241B2 (en) * | 2002-12-16 | 2006-08-29 | Hoffmann-La Roche Inc. | Thiophene hydroxamic acid derivatives |
| WO2004092161A1 (en) | 2003-04-11 | 2004-10-28 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| EP1636208B1 (en) | 2003-04-11 | 2012-02-29 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| US20050113566A1 (en) | 2003-04-25 | 2005-05-26 | Player Mark R. | Inhibitors of C-FMS kinase |
| US20040242673A1 (en) | 2003-05-16 | 2004-12-02 | Ambit Biosciences Corporation | Heterocyclic compounds and uses thereof |
| US7345046B2 (en) | 2003-05-30 | 2008-03-18 | Chiron Corporation | Heteroaryl-fused pyrimidinyl compounds as anticancer agents |
| EP1646642A2 (en) | 2003-07-18 | 2006-04-19 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| UY28500A1 (es) | 2003-09-05 | 2005-04-29 | Vertex Pharma | Inhibidores de proteasas de serina, en particular proteasa ns3-ns4a del vhc. |
| WO2005028502A1 (en) | 2003-09-18 | 2005-03-31 | Vertex Pharmaceuticals, Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| GB0324653D0 (en) | 2003-10-22 | 2003-11-26 | Syngenta Participations Ag | Fungicides |
| DE10359791A1 (de) | 2003-12-19 | 2005-07-21 | Bayer Healthcare Ag | Substituierte Thiophene |
| WO2005077969A2 (en) | 2004-02-04 | 2005-08-25 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| WO2006093518A2 (en) | 2004-06-25 | 2006-09-08 | Apath, Llc | Thienyl compounds for treating virus-related conditions |
| EP1771169A1 (en) | 2004-07-14 | 2007-04-11 | PTC Therapeutics, Inc. | Methods for treating hepatitis c |
| FR2873692B1 (fr) | 2004-07-29 | 2006-12-01 | Univ Claude Bernard Lyon | COMPOSITIONS CONTENANT, EN ASSOCIATION AVEC UN AGENT ANTIMICROBIEN, UN COMPOSE THIOPHENIQUE OU BENZOTHIOPHENIQUE DE FORMULE(I)PRESENTANT UNE ACTIVITE INHIBITRICE DE POMPE NorA |
| RU2007116265A (ru) | 2004-10-01 | 2008-11-10 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Ингибирование протеазы ns3-ns4a вируса hcv |
| DE102004061746A1 (de) | 2004-12-22 | 2006-07-06 | Bayer Healthcare Ag | Alkinyl-substituierte Thiophene |
| DE102005028077A1 (de) | 2004-12-22 | 2006-07-13 | Aicuris Gmbh & Co. Kg | Alkinyl-substituierte Thiophene |
| BRPI0610283A2 (pt) * | 2005-05-13 | 2010-10-19 | Virochem Pharma Inc | composto, uso do mesmo na preparação de um medicamento para o tratamento ou prevenção de uma infecção por vìrus de hepatite c, composição farmacêutica e combinação farmacêutica |
| JP2006334109A (ja) | 2005-06-01 | 2006-12-14 | Matsushita Electric Works Ltd | ヘアセット装置 |
| CA2670260A1 (en) | 2006-11-15 | 2008-05-22 | Virochem Pharma Inc. | Thiophene analogues for the treatment or prevention of flavivirus infections |
-
2006
- 2006-05-15 BR BRPI0610283-2A patent/BRPI0610283A2/pt not_active IP Right Cessation
- 2006-05-15 CN CN2006800248617A patent/CN101218224B/zh not_active Expired - Fee Related
- 2006-05-15 EP EP06741500A patent/EP1879879B1/en active Active
- 2006-05-15 EP EP12004718.8A patent/EP2546246A3/en not_active Withdrawn
- 2006-05-15 CN CN2012101163717A patent/CN102718744A/zh active Pending
- 2006-05-15 CA CA2607359A patent/CA2607359C/en not_active Expired - Fee Related
- 2006-05-15 JP JP2008510379A patent/JP5030947B2/ja not_active Expired - Fee Related
- 2006-05-15 WO PCT/CA2006/000786 patent/WO2006119646A1/en not_active Ceased
- 2006-05-15 KR KR1020077028215A patent/KR20080016597A/ko not_active Ceased
- 2006-05-15 EA EA200702493A patent/EA016071B1/ru not_active IP Right Cessation
- 2006-05-15 US US11/433,749 patent/US7569600B2/en not_active Expired - Fee Related
- 2006-05-15 EP EP12004696A patent/EP2543664A1/en not_active Withdrawn
- 2006-05-15 NZ NZ563909A patent/NZ563909A/en not_active IP Right Cessation
- 2006-05-15 MX MX2007014117A patent/MX2007014117A/es active IP Right Grant
- 2006-05-15 AU AU2006246227A patent/AU2006246227B2/en not_active Ceased
- 2006-05-15 SG SG201002905-6A patent/SG161315A1/en unknown
- 2006-05-15 ES ES06741500T patent/ES2415742T3/es active Active
- 2006-05-15 AP AP2007004245A patent/AP2007004245A0/xx unknown
-
2007
- 2007-11-12 ZA ZA200709727A patent/ZA200709727B/xx unknown
-
2009
- 2009-07-24 US US12/508,893 patent/US8158675B2/en not_active Expired - Fee Related
-
2012
- 2012-03-09 US US13/416,565 patent/US8674118B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008540463A5 (https=) | ||
| CA2607359A1 (en) | Compounds and methods for the treatment or prevention of flavivirus infections | |
| JP4926403B2 (ja) | フラビウイルス感染の処置もしくは予防のための化合物および方法 | |
| ZA200309590B (en) | Thiophene derivatives as antiviral agents for flavivirus infection. | |
| JP2013512247A5 (https=) | ||
| US8357718B2 (en) | Compounds and methods for the treatment or prevention of flavivirus infections | |
| JP5774008B2 (ja) | Ｆｌａｖｉｖｉｒｉｄａｅウイルスの阻害剤 | |
| NZ600816A (en) | Inhibitors of flaviviridae viruses | |
| JP5080241B2 (ja) | Ｊｎｋ阻害剤およびスクロスポリンを含んでなる組成物 | |
| JP2016512825A5 (https=) | ||
| JP2005500288A5 (https=) | ||
| JP2012533630A (ja) | フラビウイルス科ウイルスの阻害剤 | |
| JP2009538882A (ja) | 皮膚疾患の治療のためのｊｎｋ阻害物質 | |
| CA2808291A1 (en) | Compounds and methods for the treatment or prevention of flaviviridae viral infections | |
| RU2011124960A (ru) | Ингибиторы гликогенсинтаза-киназы 3-бета, содержащие производные 7-гидроксибензоимидазол-4-илметанова | |
| HK1177453A (en) | Compounds and methods for the treatment or prevention of flavivirus infections | |
| HK1139944A (en) | Thiophene derivatives as antiviral agents for flavivirus infection |