KR20080016597A - 플라비바이러스 감염의 예방 또는 치료용 화합물 및 그의예방 또는 치료 방법 - Google Patents
플라비바이러스 감염의 예방 또는 치료용 화합물 및 그의예방 또는 치료 방법 Download PDFInfo
- Publication number
- KR20080016597A KR20080016597A KR1020077028215A KR20077028215A KR20080016597A KR 20080016597 A KR20080016597 A KR 20080016597A KR 1020077028215 A KR1020077028215 A KR 1020077028215A KR 20077028215 A KR20077028215 A KR 20077028215A KR 20080016597 A KR20080016597 A KR 20080016597A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- trans
- methyl
- amino
- thiophene
- 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.)
- Ceased
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 290
- 238000000034 method Methods 0.000 title claims description 92
- 206010054261 Flavivirus infection Diseases 0.000 title description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 239000012453 solvate Substances 0.000 claims abstract description 21
- 241000710831 Flavivirus Species 0.000 claims abstract description 16
- 230000009385 viral infection Effects 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 741
- -1 substituted Chemical class 0.000 claims description 353
- 125000001072 heteroaryl group Chemical group 0.000 claims description 133
- 125000000623 heterocyclic group Chemical group 0.000 claims description 129
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 125
- 125000003118 aryl group Chemical group 0.000 claims description 108
- 229910052736 halogen Inorganic materials 0.000 claims description 74
- 150000002367 halogens Chemical class 0.000 claims description 74
- 125000003545 alkoxy group Chemical group 0.000 claims description 71
- 125000000304 alkynyl group Chemical group 0.000 claims description 63
- 239000002253 acid Substances 0.000 claims description 62
- 125000003342 alkenyl group Chemical group 0.000 claims description 62
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 60
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 59
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 57
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 56
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 53
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 49
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 45
- 229910052799 carbon Inorganic materials 0.000 claims description 44
- 241000711549 Hepacivirus C Species 0.000 claims description 43
- 230000003612 virological effect Effects 0.000 claims description 43
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 33
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 32
- 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 32
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 31
- 125000004104 aryloxy group Chemical group 0.000 claims description 30
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 239000003112 inhibitor Substances 0.000 claims description 23
- 125000004043 oxo group Chemical group O=* 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 108010050904 Interferons Proteins 0.000 claims description 21
- 102000014150 Interferons Human genes 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 150000002923 oximes Chemical class 0.000 claims description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
- 150000007513 acids Chemical class 0.000 claims description 16
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 14
- 229940079322 interferon Drugs 0.000 claims description 14
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
- 241000700605 Viruses Species 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 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 description 11
- 239000003001 serine protease inhibitor Substances 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims description 8
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 8
- 108060004795 Methyltransferase Proteins 0.000 claims description 8
- 229940123066 Polymerase inhibitor Drugs 0.000 claims description 8
- 229940122055 Serine protease inhibitor Drugs 0.000 claims description 8
- 101710102218 Serine protease inhibitor Proteins 0.000 claims description 8
- 239000002955 immunomodulating agent Substances 0.000 claims description 8
- 229940121354 immunomodulator Drugs 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 229940121759 Helicase inhibitor Drugs 0.000 claims description 7
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 7
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 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 description 6
- DHZRKGZVOWHWSR-UHFFFAOYSA-N 5-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-3-[(4-hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1CCC2(CC=1)OCCO2)C(O)=O)C1CCC(O)CC1 DHZRKGZVOWHWSR-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 108091005804 Peptidases Proteins 0.000 claims description 6
- 239000004365 Protease Substances 0.000 claims description 6
- 230000000692 anti-sense effect Effects 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims description 6
- 230000002584 immunomodulator Effects 0.000 claims description 6
- 235000012054 meals Nutrition 0.000 claims description 6
- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 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 description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 230000003078 antioxidant effect Effects 0.000 claims description 5
- 239000003443 antiviral agent Substances 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 5
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 5
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 5
- 229940021747 therapeutic vaccine Drugs 0.000 claims description 5
- OQJNOHVPDZQBCM-UHFFFAOYSA-N 5-(3-hydroxycyclohexen-1-yl)-3-[(4-methylcyclohexanecarbonyl)-[4-(oxan-2-yloxy)cyclohexyl]amino]thiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1CCCC(O)C=1)C(O)=O)C1CCC(OC2OCCCC2)CC1 OQJNOHVPDZQBCM-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
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- 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 description 4
- NYTDFZMGNVINAW-SAABIXHNSA-N C[C@H]1CC[C@@H](CC1)C(=O)N(C1CCNCC1)c1cc(sc1C(O)=O)C1=CCCCC1 Chemical compound C[C@H]1CC[C@@H](CC1)C(=O)N(C1CCNCC1)c1cc(sc1C(O)=O)C1=CCCCC1 NYTDFZMGNVINAW-SAABIXHNSA-N 0.000 claims description 4
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
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- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 4
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 4
- 229960003805 amantadine Drugs 0.000 claims description 4
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 4
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 4
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- 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 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- LCJVIYPJPCBWKS-NXPQJCNCSA-N thymosin Chemical group 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 description 4
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- OGBAPGFURAIVAC-UHFFFAOYSA-N 5-(3-hydroxycyclohexen-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(O)C=1)C(O)=O)C1CCC(O)CC1 OGBAPGFURAIVAC-UHFFFAOYSA-N 0.000 claims description 3
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- 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 description 3
- 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 description 3
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- BQQHXIZCAPCAQE-UHFFFAOYSA-N methyl 3-amino-5-(4,4-dimethylcyclohexen-1-yl)thiophene-2-carboxylate Chemical compound NC1=C(C(=O)OC)SC(C=2CCC(C)(C)CC=2)=C1 BQQHXIZCAPCAQE-UHFFFAOYSA-N 0.000 description 1
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- NKMNDFXAMGNIMF-UHFFFAOYSA-N methyl 3-bromo-5-(4,4-dimethylcyclohexen-1-yl)thiophene-2-carboxylate Chemical compound BrC1=C(C(=O)OC)SC(C=2CCC(C)(C)CC=2)=C1 NKMNDFXAMGNIMF-UHFFFAOYSA-N 0.000 description 1
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- XSKFBQUERIPAKH-UHFFFAOYSA-N methyl 5-(1,4-dioxaspiro[4.5]decan-8-yl)-3-[(4-methoxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylate Chemical compound C1CC(OC)CCC1N(C1=C(SC(=C1)C1CCC2(CC1)OCCO2)C(=O)OC)C(=O)C1CCC(C)CC1 XSKFBQUERIPAKH-UHFFFAOYSA-N 0.000 description 1
- SDBPCUBBQPSQIX-UHFFFAOYSA-N methyl 5-(4,4-dimethylcyclohexen-1-yl)-3-[(4-methylcyclohexanecarbonyl)-[4-(1,2,4-triazol-1-yl)cyclohexyl]amino]thiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C=2CCC(C)(C)CC=2)=CC=1N(C(=O)C1CCC(C)CC1)C(CC1)CCC1N1C=NC=N1 SDBPCUBBQPSQIX-UHFFFAOYSA-N 0.000 description 1
- TZUJJCSDLZTBCF-UHFFFAOYSA-N methyl 5-(4,4-dimethylcyclohexen-1-yl)-3-[[4-(1,2,4-triazol-1-yl)cyclohexyl]amino]thiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C=2CCC(C)(C)CC=2)=CC=1NC(CC1)CCC1N1C=NC=N1 TZUJJCSDLZTBCF-UHFFFAOYSA-N 0.000 description 1
- XHDJCEAGKSIJBB-UHFFFAOYSA-N methyl 5-(4,4-dimethylcyclohexen-1-yl)-3-[[4-(methoxymethoxy)cyclohexyl]-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylate Chemical compound C1CC(OCOC)CCC1N(C1=C(SC(=C1)C=1CCC(C)(C)CC=1)C(=O)OC)C(=O)C1CCC(C)CC1 XHDJCEAGKSIJBB-UHFFFAOYSA-N 0.000 description 1
- WLZHXIQKYJUIQZ-UHFFFAOYSA-N methyl 5-(4,4-dimethylcyclohexyl)-3-[(4-methylcyclohexanecarbonyl)-(4-methylsulfonyloxycyclohexyl)amino]thiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C2CCC(C)(C)CC2)=CC=1N(C(=O)C1CCC(C)CC1)C1CCC(OS(C)(=O)=O)CC1 WLZHXIQKYJUIQZ-UHFFFAOYSA-N 0.000 description 1
- PPNFNPIBVRLCFC-UHFFFAOYSA-N methyl 5-(4,4-dimethylcyclohexyl)-3-[(4-methylcyclohexanecarbonyl)-[4-(triazol-1-yl)cyclohexyl]amino]thiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C2CCC(C)(C)CC2)=CC=1N(C(=O)C1CCC(C)CC1)C(CC1)CCC1N1C=CN=N1 PPNFNPIBVRLCFC-UHFFFAOYSA-N 0.000 description 1
- ATEZBAUSRGJRTP-UHFFFAOYSA-N methyl 5-(cyclohexen-1-yl)-3-(n-(4-methylcyclohexanecarbonyl)anilino)thiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C=2CCCCC=2)=CC=1N(C=1C=CC=CC=1)C(=O)C1CCC(C)CC1 ATEZBAUSRGJRTP-UHFFFAOYSA-N 0.000 description 1
- XSKJQHJBKMWKSS-UHFFFAOYSA-N methyl 5-(cyclohexen-1-yl)-3-[(3-oxo-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl)amino]thiophene-2-carboxylate Chemical compound C=1C(NC2CC3N(C(CC3)=O)CC2)=C(C(=O)OC)SC=1C1=CCCCC1 XSKJQHJBKMWKSS-UHFFFAOYSA-N 0.000 description 1
- OSUVFWFEGCZXCD-UHFFFAOYSA-N methyl 5-(cyclohexen-1-yl)-3-[(4-methoxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylate Chemical compound C1CC(OC)CCC1N(C1=C(SC(=C1)C=1CCCCC=1)C(=O)OC)C(=O)C1CCC(C)CC1 OSUVFWFEGCZXCD-UHFFFAOYSA-N 0.000 description 1
- PYNHJVXZJFCQHI-UHFFFAOYSA-N methyl 5-(cyclohexen-1-yl)-3-[(4-methylcyclohexanecarbonyl)-(2-methyl-3-oxo-2-azaspiro[4.5]decan-8-yl)amino]thiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C=2CCCCC=2)=CC=1N(C(=O)C1CCC(C)CC1)C(CC1)CCC21CN(C)C(=O)C2 PYNHJVXZJFCQHI-UHFFFAOYSA-N 0.000 description 1
- PFVAJVRMWSPGKC-UHFFFAOYSA-N methyl 5-(cyclohexen-1-yl)-3-[(4-methylcyclohexanecarbonyl)-(3-oxo-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl)amino]thiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C=2CCCCC=2)=CC=1N(C1CC2N(C(CC2)=O)CC1)C(=O)C1CCC(C)CC1 PFVAJVRMWSPGKC-UHFFFAOYSA-N 0.000 description 1
- UJPXPQITBKABOQ-UHFFFAOYSA-N methyl 5-(cyclohexen-1-yl)-3-[(4-methylcyclohexanecarbonyl)-[1-(2-methylpropanoyl)piperidin-4-yl]amino]thiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C=2CCCCC=2)=CC=1N(C(=O)C1CCC(C)CC1)C1CCN(C(=O)C(C)C)CC1 UJPXPQITBKABOQ-UHFFFAOYSA-N 0.000 description 1
- SCTGGEQFOGRINW-UHFFFAOYSA-N methyl 5-(cyclohexen-1-yl)-3-[(4-methylcyclohexanecarbonyl)-[4-(1,2,4-triazol-1-yl)cyclohexyl]amino]thiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C=2CCCCC=2)=CC=1N(C(=O)C1CCC(C)CC1)C(CC1)CCC1N1C=NC=N1 SCTGGEQFOGRINW-UHFFFAOYSA-N 0.000 description 1
- HCPWLJURHZATCV-UHFFFAOYSA-N methyl 5-(cyclohexen-1-yl)-3-[(4-methylcyclohexanecarbonyl)-piperidin-4-ylamino]thiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C=2CCCCC=2)=CC=1N(C(=O)C1CCC(C)CC1)C1CCNCC1 HCPWLJURHZATCV-UHFFFAOYSA-N 0.000 description 1
- CKAFQCCNBSOGEI-UHFFFAOYSA-N methyl 5-(cyclohexen-1-yl)-3-[[4-(methoxymethoxy)cyclohexyl]-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylate Chemical compound C1CC(OCOC)CCC1N(C1=C(SC(=C1)C=1CCCCC=1)C(=O)OC)C(=O)C1CCC(C)CC1 CKAFQCCNBSOGEI-UHFFFAOYSA-N 0.000 description 1
- YBXCOOWWSWKENH-UHFFFAOYSA-N methyl 5-(cyclohexen-1-yl)-3-[cyclohex-3-en-1-yl-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C=2CCCCC=2)=CC=1N(C(=O)C1CCC(C)CC1)C1CCC=CC1 YBXCOOWWSWKENH-UHFFFAOYSA-N 0.000 description 1
- JWGYYGHNONYRSO-UHFFFAOYSA-N methyl 5-bromo-3-(1,4-dioxaspiro[4.5]decan-8-ylamino)thiophene-2-carboxylate Chemical compound S1C(Br)=CC(NC2CCC3(CC2)OCCO3)=C1C(=O)OC JWGYYGHNONYRSO-UHFFFAOYSA-N 0.000 description 1
- PYTFYQSPFFVGMA-UHFFFAOYSA-N methyl 5-bromo-3-[(2,2-dimethyl-1,3-dioxan-5-yl)amino]thiophene-2-carboxylate Chemical compound S1C(Br)=CC(NC2COC(C)(C)OC2)=C1C(=O)OC PYTFYQSPFFVGMA-UHFFFAOYSA-N 0.000 description 1
- MXZRZTHTXZXYIZ-UHFFFAOYSA-N methyl 5-bromo-3-[(4-hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylate Chemical compound S1C(Br)=CC(N(C2CCC(O)CC2)C(=O)C2CCC(C)CC2)=C1C(=O)OC MXZRZTHTXZXYIZ-UHFFFAOYSA-N 0.000 description 1
- IGJSQSPXSPMZLX-UHFFFAOYSA-N methyl 5-bromo-3-[1,3-dihydroxypropan-2-yl-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylate Chemical compound S1C(Br)=CC(N(C(CO)CO)C(=O)C2CCC(C)CC2)=C1C(=O)OC IGJSQSPXSPMZLX-UHFFFAOYSA-N 0.000 description 1
- QRHBBGITAUTBKO-UHFFFAOYSA-N methyl 5-bromo-3-[1,3-dioxan-5-yl-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylate Chemical compound S1C(Br)=CC(N(C2COCOC2)C(=O)C2CCC(C)CC2)=C1C(=O)OC QRHBBGITAUTBKO-UHFFFAOYSA-N 0.000 description 1
- YMZBNCXRVMHBHA-UHFFFAOYSA-N methyl 5-cyclohex-2-en-1-yl-3-[(4-hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C2C=CCCC2)=CC=1N(C(=O)C1CCC(C)CC1)C1CCC(O)CC1 YMZBNCXRVMHBHA-UHFFFAOYSA-N 0.000 description 1
- UODPHKFUTYRNDZ-UHFFFAOYSA-N methyl 5-cyclohex-2-en-1-yl-3-[(4-methylcyclohexanecarbonyl)-(4-oxocyclohexyl)amino]thiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C2C=CCCC2)=CC=1N(C(=O)C1CCC(C)CC1)C1CCC(=O)CC1 UODPHKFUTYRNDZ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XMWFMEYDRNJSOO-UHFFFAOYSA-N morpholine-4-carbonyl chloride Chemical compound ClC(=O)N1CCOCC1 XMWFMEYDRNJSOO-UHFFFAOYSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 description 1
- NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical group [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- WVULZDFWPQCPPJ-UHFFFAOYSA-N potassium;hydrochloride Chemical compound Cl.[K] WVULZDFWPQCPPJ-UHFFFAOYSA-N 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000003705 ribosome Anatomy 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012363 selectfluor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical group 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 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 description 1
- 229950006081 taribavirin Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960002935 telaprevir Drugs 0.000 description 1
- BBAWEDCPNXPBQM-GDEBMMAJSA-N telaprevir Chemical compound N([C@H](C(=O)N[C@H](C(=O)N1C[C@@H]2CCC[C@@H]2[C@H]1C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1)C(C)(C)C)C1CCCCC1)C(=O)C1=CN=CC=N1 BBAWEDCPNXPBQM-GDEBMMAJSA-N 0.000 description 1
- 108010017101 telaprevir Proteins 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000004525 thiadiazinyl group Chemical group S1NN=C(C=C1)* 0.000 description 1
- 125000005996 thiadiazolopyrimidinyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
- 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
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- 238000013519 translation Methods 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- DCGLONGLPGISNX-UHFFFAOYSA-N trimethyl(prop-1-ynyl)silane Chemical compound CC#C[Si](C)(C)C DCGLONGLPGISNX-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 229950002810 valopicitabine Drugs 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D333/40—Thiophene-2-carboxylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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| KR20080016597A true KR20080016597A (ko) | 2008-02-21 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010022238A3 (en) * | 2008-08-21 | 2010-06-10 | Health Research, Inc. | Anti-flavivirus therapeutic |
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| MX2007014117A (es) | 2008-02-05 |
| US20120164103A1 (en) | 2012-06-28 |
| EA016071B1 (ru) | 2012-01-30 |
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| EA200702493A1 (ru) | 2008-04-28 |
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| EP2546246A2 (en) | 2013-01-16 |
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| US20060276533A1 (en) | 2006-12-07 |
| ES2415742T3 (es) | 2013-07-26 |
| US7569600B2 (en) | 2009-08-04 |
| CN101218224B (zh) | 2013-05-08 |
| EP1879879A4 (en) | 2010-03-10 |
| SG161315A1 (en) | 2010-05-27 |
| CA2607359C (en) | 2011-08-09 |
| BRPI0610283A2 (pt) | 2010-10-19 |
| US8158675B2 (en) | 2012-04-17 |
| NZ563909A (en) | 2011-10-28 |
| CA2607359A1 (en) | 2006-11-16 |
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| ZA200709727B (en) | 2008-11-26 |
| AP2007004245A0 (en) | 2007-12-31 |
| US8674118B2 (en) | 2014-03-18 |
| EP2543664A1 (en) | 2013-01-09 |
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