JP2016538306A5 - - Google Patents
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- Publication number
- JP2016538306A5 JP2016538306A5 JP2016534890A JP2016534890A JP2016538306A5 JP 2016538306 A5 JP2016538306 A5 JP 2016538306A5 JP 2016534890 A JP2016534890 A JP 2016534890A JP 2016534890 A JP2016534890 A JP 2016534890A JP 2016538306 A5 JP2016538306 A5 JP 2016538306A5
- Authority
- JP
- Japan
- Prior art keywords
- chlorophenyl
- stereoisomer
- alkyl
- aryl
- phenyl
- 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.)
- Abandoned
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- 125000000217 alkyl group Chemical group 0.000 claims description 80
- 125000003118 aryl group Chemical group 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 43
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 39
- -1 trideuteromethyl Chemical group 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 208000005176 Hepatitis C Diseases 0.000 claims description 13
- 241000124008 Mammalia Species 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 208000036142 Viral infection Diseases 0.000 claims description 9
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 9
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 9
- 230000009385 viral infection Effects 0.000 claims description 9
- 229960002118 asunaprevir Drugs 0.000 claims description 8
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 claims description 8
- 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 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 108010092851 peginterferon alfa-2b Proteins 0.000 claims description 8
- 229960002091 simeprevir Drugs 0.000 claims description 8
- JTZZSQYMACOLNN-VDWJNHBNSA-N simeprevir Chemical compound O=C([C@@]12C[C@H]1\C=C/CCCCN(C)C(=O)[C@H]1[C@H](C(N2)=O)C[C@H](C1)OC=1C2=CC=C(C(=C2N=C(C=1)C=1SC=C(N=1)C(C)C)C)OC)NS(=O)(=O)C1CC1 JTZZSQYMACOLNN-VDWJNHBNSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 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 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 5
- 125000006483 4-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1I)C([H])([H])* 0.000 claims description 5
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000006189 4-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 4
- RFGUWOCFYCYEDM-ZOMNBDOOSA-N 8v42y78hru Chemical compound OP([C@@]12C[C@H]1CCCCCCC[C@@H](C(=O)N1[C@H](C(N2)=O)C[C@H](C1)OC=1C2=CC=C(C(=C2N=C(C=1)C=1N=C(NC(C)C)SC=1)Cl)OC)NC(=O)OC1CCCC1)(=O)CC1=C(F)C=CC=C1F RFGUWOCFYCYEDM-ZOMNBDOOSA-N 0.000 claims description 4
- PVRFQJIRERYGTQ-DSQUMVBZSA-N 9-[(2s,4ar,6r,7r,7ar)-7-fluoro-7-methyl-2-oxo-2-propan-2-yloxy-4,4a,6,7a-tetrahydrofuro[3,2-d][1,3,2]dioxaphosphinin-6-yl]-6-ethoxypurin-2-amine Chemical compound C([C@H]1O2)O[P@@](=O)(OC(C)C)O[C@H]1[C@](F)(C)[C@@H]2N1C(N=C(N)N=C2OCC)=C2N=C1 PVRFQJIRERYGTQ-DSQUMVBZSA-N 0.000 claims description 4
- 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 4
- OTXAMWFYPMNDME-FQQWJMKMSA-N CC[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)O[C@@H]1C[C@@H]2C[C@@H]2C1)C(C)(C)C)Oc1cc(nc2c(Cl)c(OCCN3CCOCC3)ccc12)-c1csc(NC(C)C)n1)C(O)=O Chemical compound CC[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)O[C@@H]1C[C@@H]2C[C@@H]2C1)C(C)(C)C)Oc1cc(nc2c(Cl)c(OCCN3CCOCC3)ccc12)-c1csc(NC(C)C)n1)C(O)=O OTXAMWFYPMNDME-FQQWJMKMSA-N 0.000 claims description 4
- 229930105110 Cyclosporin A Natural products 0.000 claims description 4
- 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 description 4
- 108010036949 Cyclosporine Proteins 0.000 claims description 4
- 108010047761 Interferon-alpha Proteins 0.000 claims description 4
- 102000006992 Interferon-alpha Human genes 0.000 claims description 4
- 108010050904 Interferons Proteins 0.000 claims description 4
- 102000014150 Interferons Human genes 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
- MHFMTUBUVQZIRE-WINRQGAFSA-N Sovaprevir Chemical compound C([C@H](C(=O)N1[C@@H](C[C@H](C1)OC=1C2=CC=C(C=C2N=C(C=1)C=1C=CC=CC=1)OC)C(=O)N[C@]1([C@@H](C1)C=C)C(=O)NS(=O)(=O)C1CC1)C(C)(C)C)C(=O)N1CCCCC1 MHFMTUBUVQZIRE-WINRQGAFSA-N 0.000 claims description 4
- 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 4
- 229950010541 beclabuvir Drugs 0.000 claims description 4
- 229960000517 boceprevir Drugs 0.000 claims description 4
- LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical compound 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 4
- 229960001265 ciclosporin Drugs 0.000 claims description 4
- 229950002891 danoprevir Drugs 0.000 claims description 4
- 229960001418 dasabuvir Drugs 0.000 claims description 4
- 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 4
- 229960003777 faldaprevir Drugs 0.000 claims description 4
- 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 4
- OBMNJSNZOWALQB-NCQNOWPTSA-N grazoprevir Chemical compound O=C([C@@H]1C[C@@H]2CN1C(=O)[C@@H](NC(=O)O[C@@H]1C[C@H]1CCCCCC1=NC3=CC=C(C=C3N=C1O2)OC)C(C)(C)C)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C OBMNJSNZOWALQB-NCQNOWPTSA-N 0.000 claims description 4
- 229940079322 interferon Drugs 0.000 claims description 4
- YMCAVGXTSCNFDE-BBACVFHCSA-N methyl n-[(2s)-1-[(2s)-2-[5-[4-[4-[2-[(8s)-7-[(2s)-2-(methoxycarbonylamino)-3-methylbutanoyl]-1,4-dioxa-7-azaspiro[4.4]nonan-8-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CC3(C2)OCCO3)C(=O)[C@@H](NC(=O)OC)C(C)C)N1 YMCAVGXTSCNFDE-BBACVFHCSA-N 0.000 claims description 4
- JYLMWUZJMRNMDA-SPRBZRACSA-N methyl n-[(2s)-1-[(2s)-2-[5-[6-[2-[(2s)-1-[(2s)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidin-2-yl]-3h-benzimidazol-5-yl]naphthalen-2-yl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate;dihydrochloride Chemical compound Cl.Cl.COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=C3C=CC(=CC3=CC=2)C=2C=C3NC(=NC3=CC=2)[C@H]2N(CCC2)C(=O)[C@@H](NC(=O)OC)C(C)C)N1 JYLMWUZJMRNMDA-SPRBZRACSA-N 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- LSYBRGMTRKJATA-IVEWBXRVSA-N odalasvir Chemical compound C1=C2NC([C@H]3N([C@H]4CCCC[C@H]4C3)C(=O)[C@H](C(C)C)NC(=O)OC)=NC2=CC=C1C(C(CC1)=CC=2)=CC=2CCC2=CC=C1C=C2C1=CC=C(N=C(N2)[C@H]3N([C@H]4CCCC[C@H]4C3)C(=O)[C@@H](NC(=O)OC)C(C)C)C2=C1 LSYBRGMTRKJATA-IVEWBXRVSA-N 0.000 claims description 4
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 claims description 4
- 229960000518 ombitasvir Drugs 0.000 claims description 4
- 229960002754 paritaprevir Drugs 0.000 claims description 4
- UAUIUKWPKRJZJV-MDJGTQRPSA-N paritaprevir Chemical compound C1=NC(C)=CN=C1C(=O)N[C@@H]1C(=O)N2C[C@H](OC=3C4=CC=CC=C4C4=CC=CC=C4N=3)C[C@H]2C(=O)N[C@]2(C(=O)NS(=O)(=O)C3CC3)C[C@@H]2\C=C/CCCCC1 UAUIUKWPKRJZJV-MDJGTQRPSA-N 0.000 claims description 4
- 229960003931 peginterferon alfa-2b Drugs 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- FGHMGRXAHIXTBM-TWFJNEQDSA-N s-[2-[[(2r,3r,4r,5r)-5-(2-amino-6-oxo-3h-purin-9-yl)-3,4-dihydroxy-4-methyloxolan-2-yl]methoxy-(benzylamino)phosphoryl]oxyethyl] 3-hydroxy-2,2-dimethylpropanethioate Chemical compound C([C@@H]1[C@H]([C@@](C)(O)[C@H](N2C3=C(C(NC(N)=N3)=O)N=C2)O1)O)OP(=O)(OCCSC(=O)C(C)(CO)C)NCC1=CC=CC=C1 FGHMGRXAHIXTBM-TWFJNEQDSA-N 0.000 claims description 4
- DEKOYVOWOVJMPM-RLHIPHHXSA-N setrobuvir Chemical compound N1([C@H]2[C@@H]3CC[C@@H](C3)[C@H]2C(O)=C(C1=O)C=1NC2=CC=C(C=C2S(=O)(=O)N=1)NS(=O)(=O)C)CC1=CC=C(F)C=C1 DEKOYVOWOVJMPM-RLHIPHHXSA-N 0.000 claims description 4
- VPHXUNBMNWOYNQ-XLBCSPGISA-N setrobuvir Chemical compound N1([C@H]2[C@@H]3CC[C@@H](C3)[C@H]2C(=O)/C(C1=O)=C1/NC2=CC=C(C=C2S(=O)(=O)N1)NS(=O)(=O)C)CC1=CC=C(F)C=C1 VPHXUNBMNWOYNQ-XLBCSPGISA-N 0.000 claims description 4
- 229950004113 setrobuvir Drugs 0.000 claims description 4
- 229960002063 sofosbuvir Drugs 0.000 claims description 4
- TTZHDVOVKQGIBA-IQWMDFIBSA-N sofosbuvir Chemical compound N1([C@@H]2O[C@@H]([C@H]([C@]2(F)C)O)CO[P@@](=O)(N[C@@H](C)C(=O)OC(C)C)OC=2C=CC=CC=2)C=CC(=O)NC1=O TTZHDVOVKQGIBA-IQWMDFIBSA-N 0.000 claims description 4
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 230000000840 anti-viral effect Effects 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- 230000003796 beauty Effects 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 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 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims 1
- 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 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 229950004886 tegobuvir Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 description 35
- 125000001475 halogen functional group Chemical group 0.000 description 14
- 241000710781 Flaviviridae Species 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 2
- 241000725619 Dengue virus Species 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US201361909414P | 2013-11-27 | 2013-11-27 | |
| US61/909,414 | 2013-11-27 | ||
| PCT/US2014/066680 WO2015080949A1 (en) | 2013-11-27 | 2014-11-20 | Piperidine and piperazine derivatives and their use in treating viral infections and cancer |
Publications (2)
| Publication Number | Publication Date |
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| JP2016538306A JP2016538306A (ja) | 2016-12-08 |
| JP2016538306A5 true JP2016538306A5 (https=) | 2018-01-11 |
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| JP2016534890A Abandoned JP2016538306A (ja) | 2013-11-27 | 2014-11-20 | 複素環化合物及びその使用方法 |
Country Status (10)
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| US (1) | US20170001988A1 (https=) |
| EP (1) | EP3074001A1 (https=) |
| JP (1) | JP2016538306A (https=) |
| KR (1) | KR20160079846A (https=) |
| CN (1) | CN106029060A (https=) |
| AU (1) | AU2014354957A1 (https=) |
| CA (1) | CA2931804A1 (https=) |
| SG (1) | SG11201604301VA (https=) |
| TW (1) | TW201605813A (https=) |
| WO (1) | WO2015080949A1 (https=) |
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| SG11201503750YA (en) * | 2012-11-16 | 2015-06-29 | Univ Cardiff | Process for preparing nucleoside prodrugs |
| CN106727574B (zh) * | 2016-12-28 | 2019-05-03 | 中国科学院武汉病毒研究所 | 马尼地平在制备治疗黄病毒科病毒感染药物中的应用 |
| US12187687B2 (en) | 2017-06-26 | 2025-01-07 | University Of Virginia Patent Foundation | Compositions and uses thereof |
| AU2018354418B2 (en) * | 2017-10-27 | 2025-09-11 | Immunebridge Inc. | Compositions and methods of making expanded hematopoietic stem cells using derivatives of fluorene |
| WO2021213460A1 (zh) * | 2020-04-23 | 2021-10-28 | 山东轩竹医药科技有限公司 | 三并环类激酶抑制剂 |
| CN116023395B (zh) * | 2021-10-25 | 2025-07-15 | 山东轩竹医药科技有限公司 | 三环类激酶抑制剂的晶型 |
| US20250074907A1 (en) * | 2021-12-22 | 2025-03-06 | The Texas A&M University System | Inhibitors of sars-cov-2 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK154078C (da) * | 1981-02-06 | 1989-05-22 | Ucb Sa | Analogifremgangsmaade til fremstilling af 2-(2-(4-(diphenyl-methyl)-1-piperazinyl)ethoxy)-acetamider eller syreadditionssalte heraf |
| GB8914040D0 (en) * | 1989-06-19 | 1989-08-09 | Wellcome Found | Agents for potentiating the effects of antitumour agents and combating multiple drug resistance |
| CA2285264A1 (en) * | 1997-04-25 | 1998-11-05 | Michiyo Gyoten | Condensed pyridazine derivatives, their production and use |
| ES2278729T3 (es) * | 2000-03-06 | 2007-08-16 | Acadia Pharmaceuticals Inc. | Compuestos azaciclicos para usar en el tratamiento de enfermedades relacionadas con la serotonina. |
| US6977301B1 (en) * | 2001-05-29 | 2005-12-20 | Ucb, S.A. | Process for preparing (S) and (R)—2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide |
| TW200831105A (en) * | 2006-12-14 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| KR101561707B1 (ko) * | 2007-03-12 | 2015-10-19 | 넥타르 테라퓨틱스 | 올리고머―항히스타민제 컨주게이트 |
| WO2010046908A2 (en) * | 2008-09-17 | 2010-04-29 | Calyx Chemicals And Pharmaceuticals Pvt. Ltd. | Novel water based process for the preparation of substituted diphenylmethyl piperazines |
| WO2010101649A2 (en) * | 2009-03-05 | 2010-09-10 | Pablo Gastaminza | Sigma 1 receptor inhibition as a novel therapeutical approach against hepatitis c virus infection |
| EP2714081A4 (en) * | 2011-05-27 | 2015-09-09 | Cytocure Llc | METHODS, COMPOSITIONS AND KIT FOR CREAM TREATMENT |
| AU2014233757B2 (en) * | 2013-03-18 | 2017-12-21 | Genoscience Pharma | Quinolines derivatives as novel anticancer agents |
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2014
- 2014-11-20 EP EP14809235.6A patent/EP3074001A1/en not_active Withdrawn
- 2014-11-20 SG SG11201604301VA patent/SG11201604301VA/en unknown
- 2014-11-20 JP JP2016534890A patent/JP2016538306A/ja not_active Abandoned
- 2014-11-20 AU AU2014354957A patent/AU2014354957A1/en not_active Abandoned
- 2014-11-20 WO PCT/US2014/066680 patent/WO2015080949A1/en not_active Ceased
- 2014-11-20 CN CN201480074026.9A patent/CN106029060A/zh active Pending
- 2014-11-20 US US15/039,781 patent/US20170001988A1/en not_active Abandoned
- 2014-11-20 CA CA2931804A patent/CA2931804A1/en not_active Abandoned
- 2014-11-20 KR KR1020167014314A patent/KR20160079846A/ko not_active Withdrawn
- 2014-11-26 TW TW103141004A patent/TW201605813A/zh unknown
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