JP2013526581A5 - - Google Patents
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- JP2013526581A5 JP2013526581A5 JP2013511379A JP2013511379A JP2013526581A5 JP 2013526581 A5 JP2013526581 A5 JP 2013526581A5 JP 2013511379 A JP2013511379 A JP 2013511379A JP 2013511379 A JP2013511379 A JP 2013511379A JP 2013526581 A5 JP2013526581 A5 JP 2013526581A5
- Authority
- JP
- Japan
- Prior art keywords
- aryl
- alkyl
- group
- alkenyl
- cycloalkyl
- 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.)
- Pending
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- 125000003118 aryl group Chemical group 0.000 claims description 96
- 150000001875 compounds Chemical class 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- -1 —NR 15 R 16 Chemical group 0.000 claims description 38
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 35
- 239000008194 pharmaceutical composition Substances 0.000 claims description 33
- 125000004414 alkyl thio group Chemical group 0.000 claims description 28
- 125000000304 alkynyl group Chemical group 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 28
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 27
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 26
- 125000005110 aryl thio group Chemical group 0.000 claims description 24
- 125000004104 aryloxy group Chemical group 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 229940124597 therapeutic agent Drugs 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 108010050904 Interferons Proteins 0.000 claims description 18
- 102000014150 Interferons Human genes 0.000 claims description 18
- 229940079322 interferon Drugs 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000005361 aryl sulfoxide group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 12
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000004450 alkenylene group Chemical group 0.000 claims description 10
- 125000004419 alkynylene group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- 239000002777 nucleoside Substances 0.000 claims description 9
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 8
- 125000005362 aryl sulfone group Chemical group 0.000 claims description 8
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 8
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 7
- 208000015181 infectious disease Diseases 0.000 claims description 7
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 7
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 6
- MAQDQJWCSSCURR-UHFFFAOYSA-N 4-[5-(cyclopropanecarbonylamino)-2-(trifluoromethoxy)phenyl]-n-[4-[(4-propylsulfonylpiperazin-1-yl)methyl]phenyl]benzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1CC(C=C1)=CC=C1NC(=O)C1=CC=C(C=2C(=CC=C(NC(=O)C3CC3)C=2)OC(F)(F)F)C=C1 MAQDQJWCSSCURR-UHFFFAOYSA-N 0.000 claims description 6
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical class 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 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- XBEQSQDCBSKCHJ-UHFFFAOYSA-N 5-[[6-[2,4-bis(trifluoromethyl)phenyl]pyridazin-3-yl]methyl]-2-(2-fluorophenyl)imidazo[4,5-c]pyridine Chemical compound FC1=CC=CC=C1C1=NC2=CN(CC=3N=NC(=CC=3)C=3C(=CC(=CC=3)C(F)(F)F)C(F)(F)F)C=CC2=N1 XBEQSQDCBSKCHJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 108010047761 Interferon-alpha Proteins 0.000 claims description 4
- 102000006992 Interferon-alpha Human genes 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000000539 amino acid group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- FEFIBEHSXLKJGI-UHFFFAOYSA-N methyl 2-[3-[[3-(6-amino-2-butoxy-8-oxo-7h-purin-9-yl)propyl-(3-morpholin-4-ylpropyl)amino]methyl]phenyl]acetate Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCN(CC=1C=C(CC(=O)OC)C=CC=1)CCCN1CCOCC1 FEFIBEHSXLKJGI-UHFFFAOYSA-N 0.000 claims description 4
- 229960003301 nivolumab Drugs 0.000 claims description 4
- 229960000329 ribavirin Drugs 0.000 claims description 4
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 4
- NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 claims description 4
- 229950006081 taribavirin Drugs 0.000 claims description 4
- 229950004886 tegobuvir Drugs 0.000 claims description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- DZRQMHSNVNTFAQ-IVGJVWKCSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;(2r,3s,4r,5s)-1-(6-ethoxyhexyl)-2-methylpiperidine-3,4,5-triol Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.CCOCCCCCCN1C[C@H](O)[C@@H](O)[C@@H](O)[C@H]1C DZRQMHSNVNTFAQ-IVGJVWKCSA-N 0.000 claims description 2
- HLQXYDHLDZTWDW-KAWPREARSA-N (2r,4s,5r)-1-(4-tert-butyl-3-methoxybenzoyl)-4-(methoxymethyl)-2-(pyrazol-1-ylmethyl)-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C([C@]1(C[C@@H]([C@@H](N1C(=O)C=1C=C(OC)C(=CC=1)C(C)(C)C)C=1SC=CN=1)COC)C(O)=O)N1C=CC=N1 HLQXYDHLDZTWDW-KAWPREARSA-N 0.000 claims description 2
- SCVHJVCATBPIHN-SJCJKPOMSA-N (3s)-3-[[(2s)-2-[[2-(2-tert-butylanilino)-2-oxoacetyl]amino]propanoyl]amino]-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic acid Chemical compound N([C@@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)COC=1C(=C(F)C=C(F)C=1F)F)C(=O)C(=O)NC1=CC=CC=C1C(C)(C)C SCVHJVCATBPIHN-SJCJKPOMSA-N 0.000 claims description 2
- AQHMBDAHQGYLIU-XNFHFXFQSA-N (3s,6s,9s,12r,15s,18s,21s,24s,27r,30s,33s)-27-[2-(dimethylamino)ethylsulfanyl]-30-ethyl-33-[(e,1r,2r)-1-hydroxy-2-methylhex-4-enyl]-24-(2-hydroxy-2-methylpropyl)-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18-tris(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10, 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)O)N(C)C(=O)[C@@H](SCCN(C)C)N(C)C1=O AQHMBDAHQGYLIU-XNFHFXFQSA-N 0.000 claims description 2
- VYFGDLGHHBUDTQ-ZLGUVYLKSA-N (5r)-n-[(2s,3s)-2-(fluoromethyl)-2-hydroxy-5-oxooxolan-3-yl]-3-isoquinolin-1-yl-5-propan-2-yl-4h-1,2-oxazole-5-carboxamide Chemical compound O=C([C@]1(ON=C(C1)C=1C2=CC=CC=C2C=CN=1)C(C)C)N[C@H]1CC(=O)O[C@]1(O)CF VYFGDLGHHBUDTQ-ZLGUVYLKSA-N 0.000 claims description 2
- RXZBMPWDPOLZGW-XMRMVWPWSA-N (E)-roxithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N/OCOCCOC)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 RXZBMPWDPOLZGW-XMRMVWPWSA-N 0.000 claims description 2
- 108010030583 (melle-4)cyclosporin Proteins 0.000 claims description 2
- VQFKFAKEUMHBLV-BYSUZVQFSA-N 1-O-(alpha-D-galactosyl)-N-hexacosanoylphytosphingosine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO[C@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQFKFAKEUMHBLV-BYSUZVQFSA-N 0.000 claims description 2
- IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims description 2
- WPMJNLCLKAKMLA-UHFFFAOYSA-N 5-(3,3-dimethylbut-1-ynyl)-3-[(4-hydroxycyclohexyl)-[(4-methylcyclohexyl)-oxomethyl]amino]-2-thiophenecarboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C#CC(C)(C)C)C(O)=O)C1CCC(O)CC1 WPMJNLCLKAKMLA-UHFFFAOYSA-N 0.000 claims description 2
- UPPWMBQIDFTBEQ-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-n-[4-(1,2,4-triazol-1-yl)phenyl]quinazolin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N=CN=C2NC=3C=CC(=CC=3)N3N=CN=C3)C2=C1 UPPWMBQIDFTBEQ-UHFFFAOYSA-N 0.000 claims description 2
- OLROWHGDTNFZBH-XEMWPYQTSA-N Alisporivir 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](C(C)C)N(CC)C(=O)[C@@H](C)N(C)C1=O OLROWHGDTNFZBH-XEMWPYQTSA-N 0.000 claims description 2
- 101001023866 Arabidopsis thaliana Mannosyl-oligosaccharide glucosidase GCS1 Proteins 0.000 claims description 2
- YQCVJBZPFAJZFJ-DVUQJCTJSA-N BI-1230 Chemical compound N([C@@H]1C(=O)N2[C@H](C(N[C@@]3(CC3\C=C/CCCCC1)C(O)=O)=O)C[C@H](C2)OC=1C2=CC=C(C(=C2N=C(C=1)C=1N=C(NC(=O)C(C)C)SC=1)C)OC)C(=O)OC1CCCC1 YQCVJBZPFAJZFJ-DVUQJCTJSA-N 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 229940122806 Cyclophilin inhibitor Drugs 0.000 claims description 2
- LLEUXCDZPQOJMY-AAEUAGOBSA-N Glu-Trp Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@H](CCC(O)=O)N)C(O)=O)=CNC2=C1 LLEUXCDZPQOJMY-AAEUAGOBSA-N 0.000 claims description 2
- 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 2
- 102100040018 Interferon alpha-2 Human genes 0.000 claims description 2
- 108010079944 Interferon-alpha2b Proteins 0.000 claims description 2
- 102000003996 Interferon-beta Human genes 0.000 claims description 2
- 108090000467 Interferon-beta Proteins 0.000 claims description 2
- IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 claims description 2
- 229940125977 NS4B inhibitor Drugs 0.000 claims description 2
- SEBFKMXJBCUCAI-UHFFFAOYSA-N NSC 227190 Natural products C1=C(O)C(OC)=CC(C2C(OC3=CC=C(C=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-UHFFFAOYSA-N 0.000 claims description 2
- 229940123066 Polymerase inhibitor Drugs 0.000 claims description 2
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 2
- 108010090287 SCY-635 Proteins 0.000 claims description 2
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims description 2
- 108010078233 Thymalfasin Proteins 0.000 claims description 2
- 102400000800 Thymosin alpha-1 Human genes 0.000 claims description 2
- HTJGLYIJVSDQAE-VWNXEWBOSA-N [(1s,6s,7s,8r,8ar)-1,7,8-trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl] butanoate Chemical compound O[C@H]1[C@H](O)[C@@H](OC(=O)CCC)CN2CC[C@H](O)[C@@H]21 HTJGLYIJVSDQAE-VWNXEWBOSA-N 0.000 claims description 2
- ZWELIJXAKMASLK-UGKPPGOTSA-N [(2r,3r,4r,5r)-4-acetyloxy-5-(5-amino-2-oxo-[1,3]thiazolo[4,5-d]pyrimidin-3-yl)-2-(hydroxymethyl)oxolan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@@H](CO)O[C@H]1N1C(=O)SC2=CN=C(N)N=C21 ZWELIJXAKMASLK-UGKPPGOTSA-N 0.000 claims description 2
- TVRCRTJYMVTEFS-ICGCPXGVSA-N [(2r,3r,4r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)-4-methyloxolan-3-yl] (2s)-2-amino-3-methylbutanoate Chemical compound C[C@@]1(O)[C@H](OC(=O)[C@@H](N)C(C)C)[C@@H](CO)O[C@H]1N1C(=O)N=C(N)C=C1 TVRCRTJYMVTEFS-ICGCPXGVSA-N 0.000 claims description 2
- HOOMGTNENMZAFP-NYNCVSEMSA-N [(2r,3r,5s)-2-(5-amino-2-oxo-[1,3]thiazolo[4,5-d]pyrimidin-3-yl)-5-(hydroxymethyl)oxolan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1C[C@@H](CO)O[C@H]1N1C(=O)SC2=CN=C(N)N=C21 HOOMGTNENMZAFP-NYNCVSEMSA-N 0.000 claims description 2
- YQNQNVDNTFHQSW-UHFFFAOYSA-N acetic acid [2-[[(5-nitro-2-thiazolyl)amino]-oxomethyl]phenyl] ester Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C([N+]([O-])=O)S1 YQNQNVDNTFHQSW-UHFFFAOYSA-N 0.000 claims description 2
- 108010058359 alisporivir Proteins 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- ZTTKEBYSXUCBSE-QDFUAKMASA-N beclabuvir Chemical compound C1([C@@H]2C[C@@]2(CN2C3=CC(=CC=C33)C(=O)NS(=O)(=O)N(C)C)C(=O)N4[C@@H]5CC[C@H]4CN(C)C5)=CC(OC)=CC=C1C2=C3C1CCCCC1 ZTTKEBYSXUCBSE-QDFUAKMASA-N 0.000 claims description 2
- 229950010541 beclabuvir Drugs 0.000 claims description 2
- WVROWPPEIMRGAB-UHFFFAOYSA-N bit225 Chemical compound C1=NN(C)C=C1C1=CC=CC2=CC(C(=O)NC(N)=N)=CC=C12 WVROWPPEIMRGAB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229950003414 celgosivir Drugs 0.000 claims description 2
- 239000000134 cyclophilin inhibitor Substances 0.000 claims description 2
- FKRSSPOQAMALKA-CUPIEXAXSA-N daclatasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N(CCC2)C(=O)[C@@H](NC(=O)OC)C(C)C)=CN1 FKRSSPOQAMALKA-CUPIEXAXSA-N 0.000 claims description 2
- 229960005449 daclatasvir Drugs 0.000 claims description 2
- ZVTDLPBHTSMEJZ-JSZLBQEHSA-N danoprevir Chemical compound O=C([C@@]12C[C@H]1\C=C/CCCCC[C@@H](C(N1C[C@@H](C[C@H]1C(=O)N2)OC(=O)N1CC2=C(F)C=CC=C2C1)=O)NC(=O)OC(C)(C)C)NS(=O)(=O)C1CC1 ZVTDLPBHTSMEJZ-JSZLBQEHSA-N 0.000 claims description 2
- CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 claims description 2
- 229960001418 dasabuvir Drugs 0.000 claims description 2
- NBRBXGKOEOGLOI-UHFFFAOYSA-N dasabuvir Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O NBRBXGKOEOGLOI-UHFFFAOYSA-N 0.000 claims description 2
- BMAIGAHXAJEULY-UKTHLTGXSA-N deleobuvir Chemical compound C12=CC=C(C(=O)NC3(CCC3)C=3N(C4=CC(\C=C\C(O)=O)=CC=C4N=3)C)C=C2N(C)C(C=2N=CC(Br)=CN=2)=C1C1CCCC1 BMAIGAHXAJEULY-UKTHLTGXSA-N 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229950000234 emricasan Drugs 0.000 claims description 2
- LLGDPTDZOVKFDU-XUHJSTDZSA-N faldaprevir Chemical compound N([C@H](C(=O)N1[C@@H](C[C@H](C1)OC=1C2=CC=C(C(=C2N=C(C=1)C=1N=C(NC(=O)C(C)C)SC=1)Br)OC)C(=O)N[C@]1([C@@H](C1)C=C)C(O)=O)C(C)(C)C)C(=O)OC1CCCC1 LLGDPTDZOVKFDU-XUHJSTDZSA-N 0.000 claims description 2
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims description 2
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims description 2
- 229960002751 imiquimod Drugs 0.000 claims description 2
- 229940090438 infergen Drugs 0.000 claims description 2
- 108010045648 interferon omega 1 Proteins 0.000 claims description 2
- 229960001388 interferon-beta Drugs 0.000 claims description 2
- 238000013160 medical therapy Methods 0.000 claims description 2
- VKHAHZOOUSRJNA-GCNJZUOMSA-N mifepristone Chemical compound C1([C@@H]2C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]3CC[C@@]([C@]3(C2)C)(O)C#CC)=CC=C(N(C)C)C=C1 VKHAHZOOUSRJNA-GCNJZUOMSA-N 0.000 claims description 2
- 229960001110 miglitol Drugs 0.000 claims description 2
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- XMZSTQYSBYEENY-RMKNXTFCSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 XMZSTQYSBYEENY-RMKNXTFCSA-N 0.000 claims description 2
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| US8580842B2 (en) | 2003-09-30 | 2013-11-12 | Abbott Gmbh & Co. Kg | Heteroaryl-substituted 1,3-dihydroindol-2-one derivatives and medicaments containing them |
| US20080167286A1 (en) | 2006-12-12 | 2008-07-10 | Abbott Laboratories | Pharmaceutical compositions and their methods of use |
| DK2094702T3 (en) | 2006-12-14 | 2015-12-07 | Gilead Sciences Inc | viral inhibitors |
| EP2231644B1 (de) | 2007-12-07 | 2014-01-15 | AbbVie Deutschland GmbH & Co KG | 5,6-Disubstitutierte Oxindol-Derivate und ihre Verwendung zur Herstellung eines Medikaments zur Behandlung von Vasopressin-abhängigen Erkrankungen |
| ES2398676T3 (es) * | 2007-12-07 | 2013-03-20 | Abbott Gmbh & Co. Kg | Derivados de oxindol sustituidos con amidometilo y su uso para la producción de un medicamento para el tratamiento de enfermedades dependientes de la vasopresina |
| NZ586651A (en) | 2007-12-07 | 2012-06-29 | Abbott Gmbh & Co Kg | 5-halogen-substituted oxindole derivatives and use thereof for treating vasopressine-dependent diseases |
| US8703774B2 (en) | 2007-12-07 | 2014-04-22 | AbbVie Deutschland GmbH & Co. KG | Carbamate-substituted oxindole derivatives and use thereof for the treatment of vasopressin-dependent diseases |
| SG176015A1 (en) | 2009-05-13 | 2011-12-29 | Gilead Sciences Inc | Antiviral compounds |
| US9040568B2 (en) | 2009-05-29 | 2015-05-26 | Abbvie Inc. | Pharmaceutical compositions for the treatment of pain |
| US9243025B2 (en) * | 2011-03-31 | 2016-01-26 | Idenix Pharmaceuticals, Llc | Compounds and pharmaceutical compositions for the treatment of viral infections |
| EP2950786B1 (en) | 2013-01-31 | 2019-11-27 | Gilead Pharmasset LLC | Combination formulation of two antiviral compounds |
| US20140309413A1 (en) * | 2013-03-11 | 2014-10-16 | Vertex Pharmaceuticals Incorporated | Methods of stereoselective synthesis of substituted nucleoside analogs |
| WO2014148451A1 (ja) * | 2013-03-19 | 2014-09-25 | 日本農薬株式会社 | 縮合複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法 |
| EA201690473A1 (ru) | 2013-08-27 | 2017-03-31 | ГАЙЛИД ФАРМАССЕТ ЭлЭлСи | Комбинированный состав двух противовирусных соединений |
| CN112898308B (zh) * | 2014-08-15 | 2026-08-07 | 正大天晴药业集团股份有限公司 | 作为tlr7激动剂的吡咯并嘧啶化合物 |
| WO2016106050A1 (en) | 2014-12-26 | 2016-06-30 | Emory University | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| BR112018015927A2 (pt) * | 2016-02-03 | 2018-12-26 | Quercegen Pharmaceuticals Llc | método para o tratamento da infecção pelo vírus zika com composições contendo quercetina |
| CN121974842A (zh) | 2016-05-10 | 2026-05-05 | C4医药公司 | 用于靶蛋白降解的胺连接的c3-戊二酰亚胺降解决定子体 |
| WO2017197046A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | C3-carbon linked glutarimide degronimers for target protein degradation |
| CN109562113A (zh) | 2016-05-10 | 2019-04-02 | C4医药公司 | 用于靶蛋白降解的螺环降解决定子体 |
| CN109562107A (zh) | 2016-05-10 | 2019-04-02 | C4医药公司 | 用于靶蛋白降解的杂环降解决定子体 |
| EP4717317A3 (en) | 2017-06-20 | 2026-06-03 | C4 Therapeutics, Inc. | N/o-linked degrons and degronimers for protein degradation |
| RU2020116571A (ru) | 2017-12-07 | 2021-11-22 | Эмори Юниверсити | N4-гидроксицитидин и производные и связанные с этим противовирусные применения |
| US20220324880A1 (en) * | 2019-06-10 | 2022-10-13 | Kymara Therapeutics, Inc. | Smarca inhibitors and uses thereof |
| AU2022279234B2 (en) | 2021-05-21 | 2025-08-28 | Gilead Sciences, Inc. | Pentacyclic derivatives as zika virus inhibitors |
| JP7723119B2 (ja) | 2021-05-21 | 2025-08-13 | ギリアード サイエンシーズ， インコーポレイテッド | ジカウイルス感染症の治療のための四環系化合物 |
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| US4968788A (en) | 1986-04-04 | 1990-11-06 | Board Of Regents, The University Of Texas System | Biologically reversible phosphate and phosphonate protective gruops |
| US5726302A (en) * | 1989-09-15 | 1998-03-10 | Gensia Inc. | Water soluble adenosine kinase inhibitors |
| US5248775A (en) * | 1989-12-11 | 1993-09-28 | The Trustees Of Princeton University | Pyrrolo(2,3-d)pyrimidines |
| US5028608A (en) | 1989-12-11 | 1991-07-02 | The Trustees Of Princeton University | N-(6-Amino-(pyrrolo(2,3-d)pyrimidin-3-ylacyl) )-glutamic acid derivatives |
| ES2083580T3 (es) | 1990-06-13 | 1996-04-16 | Arnold Glazier | Profarmacos de fosforo. |
| DK0481214T3 (da) | 1990-09-14 | 1999-02-22 | Acad Of Science Czech Republic | Prolægemidler af phosphonater |
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| ES2193839B1 (es) * | 2001-06-22 | 2005-02-16 | Almirall Prodesfarma, S.A. | Nuevos derivados de 6-fenildihidropirrolpirimidindiona. |
| GB0215293D0 (en) | 2002-07-03 | 2002-08-14 | Rega Foundation | Viral inhibitors |
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| DK2161273T3 (en) | 2003-12-22 | 2015-07-20 | Leuven K U Res & Dev | Imidazo [4,5-C] pyridine compounds and methods for antiviral therapy |
| CN101027303A (zh) * | 2004-07-27 | 2007-08-29 | 吉里德科学公司 | 咪唑并[4，5－d]嘧啶类、其应用和制备方法 |
| PT1841765E (pt) | 2004-12-21 | 2009-05-14 | Gilead Sciences Inc | Anticorpos para mcp-1 humano |
| WO2006135993A1 (en) | 2005-06-24 | 2006-12-28 | Gilead Sciences, Inc. | Pyrido(3,2-d)pyrimidines and pharmaceutical compositions useful for treating hepatitis c. |
| CN101384594A (zh) * | 2005-12-23 | 2009-03-11 | 诺瓦提斯公司 | 用作dpp-iv抑制剂的稠合杂环化合物 |
| US7754720B2 (en) | 2006-07-07 | 2010-07-13 | Gilead Sciences, Inc. | Pyridazine compound and use thereof |
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| US8673929B2 (en) | 2006-07-20 | 2014-03-18 | Gilead Sciences, Inc. | 4,6-di- and 2,4,6-trisubstituted quinazoline derivatives and pharmaceutical compositions useful for treating viral infections |
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| DK2094702T3 (en) | 2006-12-14 | 2015-12-07 | Gilead Sciences Inc | viral inhibitors |
| TW200840584A (en) | 2006-12-26 | 2008-10-16 | Gilead Sciences Inc | Pyrido(3,2-d)pyrimidines useful for treating viral infections |
| CL2008001631A1 (es) * | 2007-06-06 | 2009-01-02 | Smithkline Beecham Corp | Compuestos derivados de heterociclos sustituidos, con la presencia de un grupo fenoxi, inhibidores de transcriptasa inversa; composicion farmaceutica; y uso en el tratamiento de infecciones virales por vih. |
| UA99466C2 (en) | 2007-07-06 | 2012-08-27 | Гилиад Сайенсиз, Инк. | Crystalline pyridazine compound |
| UY31685A (es) * | 2008-03-04 | 2009-11-10 | Smithkline Beecham Corp | Compuestos antivirales, composiciones y metodos para usarlos |
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2011
- 2011-05-20 NZ NZ603310A patent/NZ603310A/en not_active IP Right Cessation
- 2011-05-20 EP EP11724336A patent/EP2571882A1/en not_active Withdrawn
- 2011-05-20 WO PCT/US2011/037305 patent/WO2011146817A1/en not_active Ceased
- 2011-05-20 US US13/699,142 patent/US8815858B2/en not_active Expired - Fee Related
- 2011-05-20 CA CA2797872A patent/CA2797872A1/en not_active Abandoned
- 2011-05-20 JP JP2013511379A patent/JP2013526581A/ja active Pending
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