JP2009542697A5 - - Google Patents
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- JP2009542697A5 JP2009542697A5 JP2009518395A JP2009518395A JP2009542697A5 JP 2009542697 A5 JP2009542697 A5 JP 2009542697A5 JP 2009518395 A JP2009518395 A JP 2009518395A JP 2009518395 A JP2009518395 A JP 2009518395A JP 2009542697 A5 JP2009542697 A5 JP 2009542697A5
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- JP
- Japan
- Prior art keywords
- substituted
- alkylene
- alpha
- group
- hcv
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 157
- 125000002947 alkylene group Chemical group 0.000 claims description 156
- 239000003112 inhibitor Substances 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- 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 57
- 239000003814 drug Substances 0.000 claims description 56
- 125000000623 heterocyclic group Chemical group 0.000 claims description 56
- 229940090438 infergen Drugs 0.000 claims description 54
- 108010010648 interferon alfacon-1 Proteins 0.000 claims description 54
- 229940079593 drug Drugs 0.000 claims description 50
- 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 50
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 48
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 41
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 40
- 229940124771 HCV-NS3 protease inhibitor Drugs 0.000 claims description 39
- 102000014150 Interferons Human genes 0.000 claims description 39
- 108010050904 Interferons Proteins 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 39
- 239000002777 nucleoside Substances 0.000 claims description 39
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 39
- 101001023866 Arabidopsis thaliana Mannosyl-oligosaccharide glucosidase GCS1 Proteins 0.000 claims description 38
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 38
- 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 36
- 208000036142 Viral infection Diseases 0.000 claims description 36
- -1 XTL-2125 Chemical compound 0.000 claims description 36
- 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 36
- 108010080374 albuferon Proteins 0.000 claims description 36
- 229960000517 boceprevir Drugs 0.000 claims description 36
- LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical group O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 claims description 36
- 229950006081 taribavirin Drugs 0.000 claims description 36
- 230000009385 viral infection Effects 0.000 claims description 36
- 239000013543 active substance Substances 0.000 claims description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims description 32
- 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 31
- 150000002148 esters Chemical class 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 29
- 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 28
- JBPUGFODGPKTDW-SFHVURJKSA-N [(3s)-oxolan-3-yl] n-[[3-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoylamino]phenyl]methyl]carbamate Chemical compound C=1C=C(C=2OC=NC=2)C(OC)=CC=1NC(=O)NC(C=1)=CC=CC=1CNC(=O)O[C@H]1CCOC1 JBPUGFODGPKTDW-SFHVURJKSA-N 0.000 claims description 27
- 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 26
- 125000000732 arylene group Chemical group 0.000 claims description 26
- 229940079322 interferon Drugs 0.000 claims description 26
- 239000012453 solvate Substances 0.000 claims description 26
- 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 25
- GVZFUVXPTPGOQT-UHFFFAOYSA-M mitoq Chemical compound CS([O-])(=O)=O.O=C1C(OC)=C(OC)C(=O)C(CCCCCCCCCC[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C GVZFUVXPTPGOQT-UHFFFAOYSA-M 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 20
- 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 18
- PKYIOGUKISFMKN-WQAIZXKXSA-N (3s,4s,6ar,6bs,8ar,9r,12as,14br)-4-(hydroxymethyl)-9-methoxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol Chemical compound C([C@@]12C)C[C@H](O)[C@](C)(CO)C1CC[C@]1(C)C2CC=C2[C@@H]3CC(C)(C)C[C@@H](OC)[C@]3(C)CC[C@]21C PKYIOGUKISFMKN-WQAIZXKXSA-N 0.000 claims description 18
- 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 18
- JBSNALXXNTWUEC-SFQUDFHCSA-N (e)-3-[4-[[1-[(3-cyclopentyl-1-methyl-2-pyridin-2-ylindole-6-carbonyl)amino]cyclobutanecarbonyl]amino]phenyl]prop-2-enoic acid Chemical compound C12=CC=C(C(=O)NC3(CCC3)C(=O)NC=3C=CC(\C=C\C(O)=O)=CC=3)C=C2N(C)C(C=2N=CC=CC=2)=C1C1CCCC1 JBSNALXXNTWUEC-SFQUDFHCSA-N 0.000 claims description 18
- 108010030583 (melle-4)cyclosporin Proteins 0.000 claims description 18
- 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 18
- QRKDOAWSBBGNLE-UHFFFAOYSA-N 2h-1,2,4-benzothiadiazine Chemical class C1=CC=C2N=CNSC2=C1 QRKDOAWSBBGNLE-UHFFFAOYSA-N 0.000 claims description 18
- NYPIRLYMDJMKGW-VPCXQMTMSA-N 4-amino-1-[(2r,3r,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]pyrimidin-2-one Chemical compound C[C@@]1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N=C(N)C=C1 NYPIRLYMDJMKGW-VPCXQMTMSA-N 0.000 claims description 18
- 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 18
- WTDWVLJJJOTABN-UHFFFAOYSA-N 5-cyclopropyl-2-(4-fluorophenyl)-6-[(2-hydroxyethyl)(methylsulfonyl)amino]-n-methyl-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC(N(CCO)S(C)(=O)=O)=C1C1CC1 WTDWVLJJJOTABN-UHFFFAOYSA-N 0.000 claims description 18
- 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 18
- 102100026720 Interferon beta Human genes 0.000 claims description 18
- 108010047761 Interferon-alpha Proteins 0.000 claims description 18
- 102000006992 Interferon-alpha Human genes 0.000 claims description 18
- 108090000467 Interferon-beta Proteins 0.000 claims description 18
- 229940123066 Polymerase inhibitor Drugs 0.000 claims description 18
- 108010078233 Thymalfasin Proteins 0.000 claims description 18
- 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 18
- VKXWOLCNTHXCLF-DXEZIKHYSA-N [(2r,3s,4r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-2-azido-3,4-bis(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate Chemical compound CC(C)C(=O)O[C@@H]1[C@H](OC(=O)C(C)C)[C@](COC(=O)C(C)C)(N=[N+]=[N-])O[C@H]1N1C(=O)N=C(N)C=C1 VKXWOLCNTHXCLF-DXEZIKHYSA-N 0.000 claims description 18
- 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 18
- 108010058359 alisporivir Proteins 0.000 claims description 18
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 18
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 18
- 229950000234 emricasan Drugs 0.000 claims description 18
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 18
- 108010046177 locteron Proteins 0.000 claims description 18
- ZBJWWKFMHOAPNS-UHFFFAOYSA-N loretin Chemical compound C1=CN=C2C(O)=C(I)C=C(S(O)(=O)=O)C2=C1 ZBJWWKFMHOAPNS-UHFFFAOYSA-N 0.000 claims description 18
- 229950010248 loretin Drugs 0.000 claims description 18
- 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 18
- RPJPZDVUUKWPGT-FOIHOXPVSA-N nim811 Chemical compound CC[C@H](C)[C@@H]1N(C)C(=O)CN(C)C(=O)[C@H](CC)NC(=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)NC1=O RPJPZDVUUKWPGT-FOIHOXPVSA-N 0.000 claims description 18
- 229960002480 nitazoxanide Drugs 0.000 claims description 18
- 150000002993 phenylalanine derivatives Chemical class 0.000 claims description 18
- 229940053146 rebetol Drugs 0.000 claims description 18
- SSERCMQZZYTNBY-UHFFFAOYSA-M sodium;3-[(4-hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]-5-phenylthiophene-2-carboxylate Chemical compound [Na+].C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C([O-])=O)C1CCC(O)CC1 SSERCMQZZYTNBY-UHFFFAOYSA-M 0.000 claims description 18
- 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 claims description 18
- IYWRCNFZPNEADN-CXODAYGWSA-N tert-butyl n-[(2s)-1-[(2s,4r)-2-[[(1r,2s)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]carbamoyl]-4-(6-methoxyisoquinolin-1-yl)oxypyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC=1C2=CC=C(C=C2C=CN=1)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C IYWRCNFZPNEADN-CXODAYGWSA-N 0.000 claims description 18
- NZVYCXVTEHPMHE-ZSUJOUNUSA-N thymalfasin Chemical compound CC(=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@@H](C)O)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@@H](C)O)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)N[C@@H](CC(N)=O)C(O)=O NZVYCXVTEHPMHE-ZSUJOUNUSA-N 0.000 claims description 18
- 229960004231 thymalfasin Drugs 0.000 claims description 18
- 229950002810 valopicitabine Drugs 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 16
- 229940047124 interferons Drugs 0.000 claims description 13
- 125000003107 substituted aryl group Chemical group 0.000 claims description 13
- 125000004450 alkenylene group Chemical group 0.000 claims description 12
- 125000004419 alkynylene group Chemical group 0.000 claims description 12
- 102000008236 Toll-Like Receptor 7 Human genes 0.000 claims description 9
- 108010060825 Toll-Like Receptor 7 Proteins 0.000 claims description 9
- 230000003213 activating effect Effects 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 229950003168 merimepodib Drugs 0.000 claims 9
- 102100024295 Maltase-glucoamylase Human genes 0.000 claims 1
- 108010028144 alpha-Glucosidases Proteins 0.000 claims 1
- 229930182480 glucuronide Natural products 0.000 claims 1
- 150000008134 glucuronides Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 description 15
- OHXPGWPVLFPUSM-KLRNGDHRSA-N 3,7,12-trioxo-5beta-cholanic acid Chemical compound C1CC(=O)C[C@H]2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(O)=O)C)[C@@]4(C)C(=O)C[C@@H]3[C@]21C OHXPGWPVLFPUSM-KLRNGDHRSA-N 0.000 description 8
- 0 *c1nc2c(N)nc(*)nc2[n]1* Chemical compound *c1nc2c(N)nc(*)nc2[n]1* 0.000 description 4
- 230000002265 prevention Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RKYDOJARHFQKCG-UHFFFAOYSA-N CC(C)OP(COCC[n](c1n2)c(O)nc1c(N)nc2OCCOC)(O)=O Chemical compound CC(C)OP(COCC[n](c1n2)c(O)nc1c(N)nc2OCCOC)(O)=O RKYDOJARHFQKCG-UHFFFAOYSA-N 0.000 description 1
- IWRPONMEFXZEEJ-UHFFFAOYSA-N CC(C[n](c1n2)c(O)nc1c(N)nc2OCCOC)OCP(O)(O)=O Chemical compound CC(C[n](c1n2)c(O)nc1c(N)nc2OCCOC)OCP(O)(O)=O IWRPONMEFXZEEJ-UHFFFAOYSA-N 0.000 description 1
- VAFPVYIXWZFANO-UHFFFAOYSA-N CC1(N(CC(Cc2ccccc2)OCP(O)(O)=O)c2nc(OCCOC)nc(N)c2N1)[O-] Chemical compound CC1(N(CC(Cc2ccccc2)OCP(O)(O)=O)c2nc(OCCOC)nc(N)c2N1)[O-] VAFPVYIXWZFANO-UHFFFAOYSA-N 0.000 description 1
- XPHMBRJJGMLZMA-UHFFFAOYSA-N COCCOc(nc1[n]2CCCP(O)(O)=O)nc(N)c1nc2O Chemical compound COCCOc(nc1[n]2CCCP(O)(O)=O)nc(N)c1nc2O XPHMBRJJGMLZMA-UHFFFAOYSA-N 0.000 description 1
- YBMBLVLPVQOODD-UHFFFAOYSA-N COCCOc(nc1[n]2CCP(O)(O)=O)nc(N)c1nc2O Chemical compound COCCOc(nc1[n]2CCP(O)(O)=O)nc(N)c1nc2O YBMBLVLPVQOODD-UHFFFAOYSA-N 0.000 description 1
- BDZOGZROXBTBPY-UHFFFAOYSA-N COCCOc(nc1[n]2Cc3cccc(CPc(cccc4)c4O)c3)nc(N)c1nc2O Chemical compound COCCOc(nc1[n]2Cc3cccc(CPc(cccc4)c4O)c3)nc(N)c1nc2O BDZOGZROXBTBPY-UHFFFAOYSA-N 0.000 description 1
- SARANQRPXLLURF-UHFFFAOYSA-N COCCOc(nc1[n]2Cc3cccc(P(C)(O)=O)c3)nc(N)c1nc2O Chemical compound COCCOc(nc1[n]2Cc3cccc(P(C)(O)=O)c3)nc(N)c1nc2O SARANQRPXLLURF-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002443 hepatoprotective effect Effects 0.000 description 1
Applications Claiming Priority (5)
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| GB9020931D0 (en) | 1990-09-26 | 1990-11-07 | Wellcome Found | Heterocyclic compounds |
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| PT2038290E (pt) * | 2006-07-07 | 2013-12-10 | Gilead Sciences Inc | Moduladores de receptor do tipo toll 7 |
| WO2010093436A2 (en) * | 2009-02-11 | 2010-08-19 | Carson Dennis A | Toll-like receptor modulators and treatment of diseases |
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2007
- 2007-07-06 PT PT78360179T patent/PT2038290E/pt unknown
- 2007-07-06 EP EP07836017.9A patent/EP2038290B1/en active Active
- 2007-07-06 WO PCT/US2007/015615 patent/WO2008005555A1/en not_active Ceased
- 2007-07-06 JP JP2009518395A patent/JP5356228B2/ja active Active
- 2007-07-06 CA CA2656427A patent/CA2656427C/en active Active
- 2007-07-06 AR ARP070103030A patent/AR061839A1/es unknown
- 2007-07-06 SI SI200731368T patent/SI2038290T1/sl unknown
- 2007-07-06 DK DK07836017.9T patent/DK2038290T3/da active
- 2007-07-06 ES ES07836017.9T patent/ES2437871T3/es active Active
- 2007-07-06 US US11/825,377 patent/US20080008682A1/en not_active Abandoned
- 2007-07-06 US US12/303,214 patent/US8338593B2/en active Active
- 2007-07-06 NZ NZ572983A patent/NZ572983A/en unknown
- 2007-07-06 AU AU2007269557A patent/AU2007269557B2/en active Active
- 2007-07-06 TW TW096124724A patent/TWI399377B/zh active
- 2007-07-06 PL PL07836017T patent/PL2038290T3/pl unknown
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