EA007484B1 - Соединения и способы лечения или предупреждения инфекций flavivirus - Google Patents
Соединения и способы лечения или предупреждения инфекций flavivirus Download PDFInfo
- Publication number
- EA007484B1 EA007484B1 EA200400022A EA200400022A EA007484B1 EA 007484 B1 EA007484 B1 EA 007484B1 EA 200400022 A EA200400022 A EA 200400022A EA 200400022 A EA200400022 A EA 200400022A EA 007484 B1 EA007484 B1 EA 007484B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- compound
- carboxylic acid
- phenylthiophene
- amino
- thiophene
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 1751
- 238000000034 method Methods 0.000 title claims description 28
- 230000002265 prevention Effects 0.000 title claims description 3
- 206010054261 Flavivirus infection Diseases 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 230000009385 viral infection Effects 0.000 claims abstract description 15
- 208000036142 Viral infection Diseases 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 313
- 125000000623 heterocyclic group Chemical group 0.000 claims description 262
- 125000003118 aryl group Chemical group 0.000 claims description 227
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 222
- -1 cyano, azido, amidino Chemical group 0.000 claims description 208
- 125000003342 alkenyl group Chemical group 0.000 claims description 136
- 125000000304 alkynyl group Chemical group 0.000 claims description 135
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 105
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 102
- 229910052799 carbon Inorganic materials 0.000 claims description 100
- 229910052739 hydrogen Inorganic materials 0.000 claims description 95
- 229910052736 halogen Inorganic materials 0.000 claims description 93
- 150000002367 halogens Chemical class 0.000 claims description 93
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 89
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 58
- 230000003612 virological effect Effects 0.000 claims description 57
- 125000003545 alkoxy group Chemical group 0.000 claims description 56
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 52
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 50
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 50
- 125000004104 aryloxy group Chemical group 0.000 claims description 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 49
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 239000003795 chemical substances by application Substances 0.000 claims description 34
- 108060004795 Methyltransferase Proteins 0.000 claims description 29
- 230000000694 effects Effects 0.000 claims description 27
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 26
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 18
- 150000003536 tetrazoles Chemical class 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- 230000002401 inhibitory effect Effects 0.000 claims description 14
- 239000012634 fragment Substances 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229910052757 nitrogen Chemical group 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 208000015181 infectious disease Diseases 0.000 claims description 11
- 239000003112 inhibitor Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 10
- WUEPMEXUMQVEGN-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;2,2,2-trifluoro-n-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamide Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C(=O)NCCNCCNC(=O)C(F)(F)F WUEPMEXUMQVEGN-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000002837 carbocyclic group Chemical group 0.000 claims description 9
- 230000003247 decreasing effect Effects 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 125000003367 polycyclic group Chemical group 0.000 claims description 9
- 239000011593 sulfur Chemical group 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical group CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 claims description 9
- UKNZREOUDLFUFF-UHFFFAOYSA-N 3-[(2,4-dichlorobenzoyl)(isopropyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(Cl)C=C1Cl UKNZREOUDLFUFF-UHFFFAOYSA-N 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000003242 anti bacterial agent Substances 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 239000003001 serine protease inhibitor Substances 0.000 claims description 7
- IUADGPRSRYATIY-UHFFFAOYSA-N 2-[[3-[(4-methylphenyl)sulfonylamino]-5-phenylthiophene-2-carbonyl]amino]acetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=C(C(=O)NCC(O)=O)SC(C=2C=CC=CC=2)=C1 IUADGPRSRYATIY-UHFFFAOYSA-N 0.000 claims description 6
- NYYKDALOYDQKPA-UHFFFAOYSA-N 3-(n-(2,4-dichlorobenzoyl)anilino)-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C=1C=CC=CC=1)C(=O)C1=CC=C(Cl)C=C1Cl NYYKDALOYDQKPA-UHFFFAOYSA-N 0.000 claims description 6
- CORJOVCCNWIHJE-UHFFFAOYSA-N 3-[(2-chlorophenyl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NS(=O)(=O)C1=CC=CC=C1Cl CORJOVCCNWIHJE-UHFFFAOYSA-N 0.000 claims description 6
- TVZQQBXPOAOCMB-UHFFFAOYSA-N 3-[[3-(1-benzofuran-2-yl)phenyl]methyl-(4-chloro-2,5-dimethylphenyl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)N(CC=2C=C(C=CC=2)C=2OC3=CC=CC=C3C=2)C2=C(SC(=C2)C=2C=CC=CC=2)C(O)=O)=C1C TVZQQBXPOAOCMB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- FXOJQJBROSJRHW-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-3-[(2-methylphenyl)sulfonylamino]thiophene-2-carboxylic acid Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2C=C(Cl)C(F)=CC=2)=C1 FXOJQJBROSJRHW-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 230000002519 immonomodulatory effect Effects 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- LBRXWPRTCUVBRS-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)-propan-2-ylcarbamoyl]-5-phenylthiophene-2-carboxylic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1N(C(C)C)C(=O)C(=C(S1)C(O)=O)C=C1C1=CC=CC=C1 LBRXWPRTCUVBRS-UHFFFAOYSA-N 0.000 claims description 5
- WHIBBUNFHUZCSG-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)methylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NCC1=CC=C(Cl)C=C1Cl WHIBBUNFHUZCSG-UHFFFAOYSA-N 0.000 claims description 5
- BACMTCNFHNDMIM-UHFFFAOYSA-N 3-[(2-methylphenyl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2C=CC=CC=2)=C1 BACMTCNFHNDMIM-UHFFFAOYSA-N 0.000 claims description 5
- CDEZPEKCNFPDPF-UHFFFAOYSA-N 3-[(4-chloro-2,5-dimethylphenyl)sulfonylamino]-5-(4-chlorophenyl)thiophene-2-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)NC2=C(SC(=C2)C=2C=CC(Cl)=CC=2)C(O)=O)=C1C CDEZPEKCNFPDPF-UHFFFAOYSA-N 0.000 claims description 5
- NXUAAIVUPKHHNC-UHFFFAOYSA-N 3-[(4-chloro-2,5-dimethylphenyl)sulfonylamino]-5-[4-(2-methylpropyl)phenyl]thiophene-2-carboxylic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(C)C=2)C)=C(C(O)=O)S1 NXUAAIVUPKHHNC-UHFFFAOYSA-N 0.000 claims description 5
- ORGXXKHNNJNAPB-UHFFFAOYSA-N 3-[(4-chlorobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NC(=O)C1=CC=C(Cl)C=C1 ORGXXKHNNJNAPB-UHFFFAOYSA-N 0.000 claims description 5
- MBSKWYRXXJFYLY-UHFFFAOYSA-N 3-[(4-methylcyclohexanecarbonyl)-piperidin-4-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C1CCNCC1 MBSKWYRXXJFYLY-UHFFFAOYSA-N 0.000 claims description 5
- VVWRGFRAROIXHC-UHFFFAOYSA-N 3-[cyclopropyl-(2,4-dichlorobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C=1C(=CC(Cl)=CC=1)Cl)C1CC1 VVWRGFRAROIXHC-UHFFFAOYSA-N 0.000 claims description 5
- WLJQGIHPQWAMSH-UHFFFAOYSA-N 3-[tert-butyl-(2,4-dichlorobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)(C)C)C(=O)C1=CC=C(Cl)C=C1Cl WLJQGIHPQWAMSH-UHFFFAOYSA-N 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- DQIRFGSUYVNJGJ-UHFFFAOYSA-N 5-(1-benzothiophen-2-yl)-3-[(2-methylphenyl)sulfonylamino]thiophene-2-carboxylic acid Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2SC3=CC=CC=C3C=2)=C1 DQIRFGSUYVNJGJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- GKOAPPFBYCPZJX-UHFFFAOYSA-N 3-[(2,4-dichlorobenzoyl)-[[5-[3-(trifluoromethyl)phenyl]furan-2-yl]methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C=1C(=CC(Cl)=CC=1)Cl)CC(O1)=CC=C1C1=CC=CC(C(F)(F)F)=C1 GKOAPPFBYCPZJX-UHFFFAOYSA-N 0.000 claims description 4
- GZNQIZXDGFRFOT-UHFFFAOYSA-N 3-[(2-chloro-4-cyanophenyl)sulfonylamino]-5-[4-(2-methylpropyl)phenyl]thiophene-2-carboxylic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(NS(=O)(=O)C=2C(=CC(=CC=2)C#N)Cl)=C(C(O)=O)S1 GZNQIZXDGFRFOT-UHFFFAOYSA-N 0.000 claims description 4
- FBBNCVURFSVLFJ-UHFFFAOYSA-N 3-[(2-methylphenyl)sulfonylamino]thiophene-2-carboxylic acid Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC=C1 FBBNCVURFSVLFJ-UHFFFAOYSA-N 0.000 claims description 4
- WBYYVLDPSBBWFU-UHFFFAOYSA-N 3-[(3-methoxyphenyl)sulfonylamino]-5-[4-(2-methylpropyl)phenyl]thiophene-2-carboxylic acid Chemical compound COC1=CC=CC(S(=O)(=O)NC2=C(SC(=C2)C=2C=CC(CC(C)C)=CC=2)C(O)=O)=C1 WBYYVLDPSBBWFU-UHFFFAOYSA-N 0.000 claims description 4
- HNLKVRCRMCFRQW-UHFFFAOYSA-N 3-[(4-bromo-2-fluorophenyl)sulfonylamino]-5-[4-(2-methylpropyl)phenyl]thiophene-2-carboxylic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(NS(=O)(=O)C=2C(=CC(Br)=CC=2)F)=C(C(O)=O)S1 HNLKVRCRMCFRQW-UHFFFAOYSA-N 0.000 claims description 4
- HRSASDAMXLSXNA-UHFFFAOYSA-N 3-[(4-bromo-2-methylphenyl)sulfonylamino]-5-[4-(2-methylpropyl)phenyl]thiophene-2-carboxylic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(NS(=O)(=O)C=2C(=CC(Br)=CC=2)C)=C(C(O)=O)S1 HRSASDAMXLSXNA-UHFFFAOYSA-N 0.000 claims description 4
- BMWYCRYHUCPJQB-UHFFFAOYSA-N 3-[(4-chloro-2,5-dimethylphenyl)sulfonyl-[(3-iodophenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)N(CC=2C=C(I)C=CC=2)C2=C(SC(=C2)C=2C=CC=CC=2)C(O)=O)=C1C BMWYCRYHUCPJQB-UHFFFAOYSA-N 0.000 claims description 4
- LSCILVWEAWFOQC-UHFFFAOYSA-N 3-[(4-chlorobenzoyl)-propan-2-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(Cl)C=C1 LSCILVWEAWFOQC-UHFFFAOYSA-N 0.000 claims description 4
- NKWOBYOHBPWASF-UHFFFAOYSA-N 3-[[2,5-bis(2,2,2-trifluoroethoxy)phenyl]sulfonylamino]-5-[4-(2-methylpropyl)phenyl]thiophene-2-carboxylic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(NS(=O)(=O)C=2C(=CC=C(OCC(F)(F)F)C=2)OCC(F)(F)F)=C(C(O)=O)S1 NKWOBYOHBPWASF-UHFFFAOYSA-N 0.000 claims description 4
- IBUFNMKTIXHEFK-UHFFFAOYSA-N 3-[benzoyl(methyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C)C(=O)C1=CC=CC=C1 IBUFNMKTIXHEFK-UHFFFAOYSA-N 0.000 claims description 4
- HJBVUFKHFIPDAV-UHFFFAOYSA-N 3-[benzyl(cyclopropanecarbonyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C1CC1)CC1=CC=CC=C1 HJBVUFKHFIPDAV-UHFFFAOYSA-N 0.000 claims description 4
- UJFMCKASZXENEG-UHFFFAOYSA-N 5-[4-(2-methylpropyl)phenyl]-3-[(2,3,4-trifluorophenyl)sulfonylamino]thiophene-2-carboxylic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(NS(=O)(=O)C=2C(=C(F)C(F)=CC=2)F)=C(C(O)=O)S1 UJFMCKASZXENEG-UHFFFAOYSA-N 0.000 claims description 4
- 229940126214 compound 3 Drugs 0.000 claims description 4
- 150000002084 enol ethers Chemical class 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims description 3
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims description 3
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- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims description 3
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 3
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 claims description 3
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- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 claims description 3
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- IGPCFSATFFOOAW-UHFFFAOYSA-N 3-[(2-chlorobenzoyl)-propan-2-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=CC=C1Cl IGPCFSATFFOOAW-UHFFFAOYSA-N 0.000 claims 2
- XTCZVASLMQSYTG-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl-(2-methylpropanoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)C(C)C)CC1=CC=CC=C1Cl XTCZVASLMQSYTG-UHFFFAOYSA-N 0.000 claims 2
- LKXVEMXRUUEKND-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl-(3-methylbutanoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)CC(C)C)CC1=CC=CC=C1Cl LKXVEMXRUUEKND-UHFFFAOYSA-N 0.000 claims 2
- SHSKYMKVNOTZRL-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl-(cyclobutanecarbonyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C1CCC1)CC1=CC=CC=C1Cl SHSKYMKVNOTZRL-UHFFFAOYSA-N 0.000 claims 2
- XVMIFBMEPZRGDG-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl-(cyclopropanecarbonyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C1CC1)CC1=CC=CC=C1Cl XVMIFBMEPZRGDG-UHFFFAOYSA-N 0.000 claims 2
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- OMRAXNSXGUIYRC-UHFFFAOYSA-N 3-[(3-methylphenyl)methyl-(2-methylpropanoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)C(C)C)CC1=CC=CC(C)=C1 OMRAXNSXGUIYRC-UHFFFAOYSA-N 0.000 claims 2
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- RSOHIWMVEKWSLM-UHFFFAOYSA-N 3-[(4-methyl-2-phenylmethoxybenzoyl)-propan-2-ylamino]-5-[3-(trifluoromethyl)phenyl]thiophene-2-carboxylic acid Chemical compound C1=C(C=2C=C(C=CC=2)C(F)(F)F)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(C)C=C1OCC1=CC=CC=C1 RSOHIWMVEKWSLM-UHFFFAOYSA-N 0.000 claims 2
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- ZGZUBSLLNPYXFW-UHFFFAOYSA-N 3-[(4-methylbenzoyl)-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C1CCN(C(=O)OC(C)(C)C)CC1 ZGZUBSLLNPYXFW-UHFFFAOYSA-N 0.000 claims 2
- RPIJHSUWCVNLHD-UHFFFAOYSA-N 3-[(4-methylbenzoyl)-piperidin-4-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C1CCNCC1 RPIJHSUWCVNLHD-UHFFFAOYSA-N 0.000 claims 2
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- SWJXGQQNGOAZMB-UHFFFAOYSA-N 3-[(4-methylbenzoyl)-propan-2-ylamino]-5-(3-methylphenyl)thiophene-2-carboxylic acid Chemical compound C1=C(C=2C=C(C)C=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(C)C=C1 SWJXGQQNGOAZMB-UHFFFAOYSA-N 0.000 claims 2
- QXGHVQVSZPCCAM-UHFFFAOYSA-N 3-[(4-methylbenzoyl)-propan-2-ylamino]-5-[3-(trifluoromethyl)phenyl]thiophene-2-carboxylic acid Chemical compound C1=C(C=2C=C(C=CC=2)C(F)(F)F)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(C)C=C1 QXGHVQVSZPCCAM-UHFFFAOYSA-N 0.000 claims 2
- UBDSFDINSRPRGT-UHFFFAOYSA-N 3-[(4-methylcyclohexanecarbonyl)-(1-methylpiperidin-4-yl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C1CCN(C)CC1 UBDSFDINSRPRGT-UHFFFAOYSA-N 0.000 claims 2
- RBSSXGJWFHIKDF-UHFFFAOYSA-N 3-[(4-methylcyclohexanecarbonyl)-(oxan-4-yl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C1CCOCC1 RBSSXGJWFHIKDF-UHFFFAOYSA-N 0.000 claims 2
- DZVLKAJKYNNNNP-UHFFFAOYSA-N 3-[(4-methylcyclohexanecarbonyl)-(piperidin-4-ylmethyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)CC1CCNCC1 DZVLKAJKYNNNNP-UHFFFAOYSA-N 0.000 claims 2
- CIGUBKIZEHTQHS-UHFFFAOYSA-N 3-[(4-methylcyclohexanecarbonyl)-propan-2-ylamino]-5-(1-methylpiperidin-4-yl)thiophene-2-carboxylic acid Chemical compound C1=C(C2CCN(C)CC2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1CCC(C)CC1 CIGUBKIZEHTQHS-UHFFFAOYSA-N 0.000 claims 2
- CLSCAZUTKBJWAC-UHFFFAOYSA-N 3-[(4-methylcyclohexanecarbonyl)-propan-2-ylamino]-5-(1-phenylmethoxycarbonyl-3,6-dihydro-2h-pyridin-4-yl)thiophene-2-carboxylic acid Chemical compound C1=C(C=2CCN(CC=2)C(=O)OCC=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1CCC(C)CC1 CLSCAZUTKBJWAC-UHFFFAOYSA-N 0.000 claims 2
- HCFGJRXLTALWMP-UHFFFAOYSA-N 3-[(4-methylcyclohexanecarbonyl)-propan-2-ylamino]-5-(3-methylphenyl)thiophene-2-carboxylic acid Chemical compound C1=C(C=2C=C(C)C=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1CCC(C)CC1 HCFGJRXLTALWMP-UHFFFAOYSA-N 0.000 claims 2
- MSRUNTZECAKRGF-UHFFFAOYSA-N 3-[(4-methylcyclohexanecarbonyl)-propan-2-ylamino]-5-(3-nitrophenyl)thiophene-2-carboxylic acid Chemical compound C1=C(C=2C=C(C=CC=2)[N+]([O-])=O)SC(C(O)=O)=C1N(C(C)C)C(=O)C1CCC(C)CC1 MSRUNTZECAKRGF-UHFFFAOYSA-N 0.000 claims 2
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- NZTSRVXQZUZJAA-UHFFFAOYSA-N 3-[(4-methylcyclohexanecarbonyl)-pyridin-4-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C=1C=CN=CC=1)C1=C(C(O)=O)SC(C=2C=CC=CC=2)=C1 NZTSRVXQZUZJAA-UHFFFAOYSA-N 0.000 claims 2
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- HCWAVDVJWSEPGB-UHFFFAOYSA-N 3-[(4-nitrophenyl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 HCWAVDVJWSEPGB-UHFFFAOYSA-N 0.000 claims 2
- FAOVOPXOPFMDLA-UHFFFAOYSA-N 3-[(4-pentylphenyl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(CCCCC)=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2C=CC=CC=2)=C1 FAOVOPXOPFMDLA-UHFFFAOYSA-N 0.000 claims 2
- ZJYRMQQMBLQPFM-UHFFFAOYSA-N 3-[(4-tert-butylphenyl)methyl-(2-cyclopentylacetyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1CN(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C(=O)CC1CCCC1 ZJYRMQQMBLQPFM-UHFFFAOYSA-N 0.000 claims 2
- HUFOUGXKBTWWSS-UHFFFAOYSA-N 3-[(4-tert-butylphenyl)methyl-(2-methylpropanoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)C(C)C)CC1=CC=C(C(C)(C)C)C=C1 HUFOUGXKBTWWSS-UHFFFAOYSA-N 0.000 claims 2
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- CCNMTSFOHGMZLG-UHFFFAOYSA-N 3-[(4-tert-butylphenyl)methyl-(cyclohexanecarbonyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1CN(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C(=O)C1CCCCC1 CCNMTSFOHGMZLG-UHFFFAOYSA-N 0.000 claims 2
- FARXTSDCCGZXMY-UHFFFAOYSA-N 3-[(4-tert-butylphenyl)methyl-(cyclopropanecarbonyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1CN(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C(=O)C1CC1 FARXTSDCCGZXMY-UHFFFAOYSA-N 0.000 claims 2
- OFDSKMIBUWTRLA-UHFFFAOYSA-N 3-[(4-tert-butylphenyl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2C=CC=CC=2)=C1 OFDSKMIBUWTRLA-UHFFFAOYSA-N 0.000 claims 2
- DWLCWYANOKPLKD-UHFFFAOYSA-N 3-[(5-carboxy-4-chloro-2-fluorophenyl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NS(=O)(=O)C1=CC(C(O)=O)=C(Cl)C=C1F DWLCWYANOKPLKD-UHFFFAOYSA-N 0.000 claims 2
- GJBLAAADNHTUSY-UHFFFAOYSA-N 3-[(5-methyl-3-oxoisoindol-1-yl)-propan-2-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound N=1C(=O)C2=CC(C)=CC=C2C=1N(C(C)C)C(=C(S1)C(O)=O)C=C1C1=CC=CC=C1 GJBLAAADNHTUSY-UHFFFAOYSA-N 0.000 claims 2
- UMKOYEADQOBGPL-UHFFFAOYSA-N 3-[(6-chloropyridine-3-carbonyl)-propan-2-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(Cl)N=C1 UMKOYEADQOBGPL-UHFFFAOYSA-N 0.000 claims 2
- IRGNGIISDPYGHQ-UHFFFAOYSA-N 3-[1,3-dioxan-5-yl-(4-methylcyclohexanecarbonyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C1COCOC1 IRGNGIISDPYGHQ-UHFFFAOYSA-N 0.000 claims 2
- GVKCGTUDJDTYGI-UHFFFAOYSA-N 3-[1-carboxyethyl-(2,4-dichlorobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C(O)=O)C(=O)C1=CC=C(Cl)C=C1Cl GVKCGTUDJDTYGI-UHFFFAOYSA-N 0.000 claims 2
- RQFGVYRDVDMKEX-UHFFFAOYSA-N 3-[1-methoxypropan-2-yl-(4-methylcyclohexanecarbonyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)COC)C(=O)C1CCC(C)CC1 RQFGVYRDVDMKEX-UHFFFAOYSA-N 0.000 claims 2
- SELUYVFFCIPMKQ-UHFFFAOYSA-N 3-[2-hydroxyethyl-(4-methylbenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1C(=O)N(CCO)C1=C(C(O)=O)SC(C=2C=CC=CC=2)=C1 SELUYVFFCIPMKQ-UHFFFAOYSA-N 0.000 claims 2
- YHPRUAXIOANOPX-UHFFFAOYSA-N 3-[2-methylpropanoyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)C(C)C)CC1=CC=C(C(F)(F)F)C=C1 YHPRUAXIOANOPX-UHFFFAOYSA-N 0.000 claims 2
- JHIWSSLLWLBCIH-UHFFFAOYSA-N 3-[3-methylbutanoyl-[(4-nitrophenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)CC(C)C)CC1=CC=C([N+]([O-])=O)C=C1 JHIWSSLLWLBCIH-UHFFFAOYSA-N 0.000 claims 2
- QZQKZKQXLNZBPC-UHFFFAOYSA-N 3-[3-methylbutanoyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)CC(C)C)CC1=CC=C(C(F)(F)F)C=C1 QZQKZKQXLNZBPC-UHFFFAOYSA-N 0.000 claims 2
- NMIYLWWSHNJBRE-UHFFFAOYSA-N 3-[4-methylpentanoyl(prop-2-enyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(O)=O)=C(N(CC=C)C(=O)CCC(C)C)C=C1C1=CC=CC=C1 NMIYLWWSHNJBRE-UHFFFAOYSA-N 0.000 claims 2
- DLBRFNKHNQCTCE-UHFFFAOYSA-N 3-[[1-(4-methoxy-2,3,6-trimethylphenyl)sulfonyl-5-methyl-3,6-dihydro-2h-pyridine-2-carbonyl]-propan-2-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound CC1=C(C)C(OC)=CC(C)=C1S(=O)(=O)N1C(C(=O)N(C(C)C)C2=C(SC(=C2)C=2C=CC=CC=2)C(O)=O)CC=C(C)C1 DLBRFNKHNQCTCE-UHFFFAOYSA-N 0.000 claims 2
- XLXYLLVQQSLUQN-UHFFFAOYSA-N 3-[[2,5-bis(2,2,2-trifluoroethoxy)phenyl]sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NS(=O)(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F XLXYLLVQQSLUQN-UHFFFAOYSA-N 0.000 claims 2
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- QTOKUIQZTHGDQB-UHFFFAOYSA-N 3-[[2-(1-benzothiophen-2-yl)-2-oxoethyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C=1C(NCC(=O)C=2SC3=CC=CC=C3C=2)=C(C(=O)O)SC=1C1=CC=CC=C1 QTOKUIQZTHGDQB-UHFFFAOYSA-N 0.000 claims 2
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- HTEBSHNOINBWMY-UHFFFAOYSA-N 3-[[2-(2,4-difluorophenyl)acetyl]-prop-2-enylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(CC=C)C(=O)CC1=CC=C(F)C=C1F HTEBSHNOINBWMY-UHFFFAOYSA-N 0.000 claims 2
- NJCTZTAIMSGUIJ-UHFFFAOYSA-N 3-[[2-(2-chloro-4-fluorophenyl)acetyl]-prop-2-enylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(CC=C)C(=O)CC1=CC=C(F)C=C1Cl NJCTZTAIMSGUIJ-UHFFFAOYSA-N 0.000 claims 2
- BLEDEFLZKLPBEQ-UHFFFAOYSA-N 3-[[2-(3,4-dichlorophenyl)acetyl]-prop-2-enylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(CC=C)C(=O)CC1=CC=C(Cl)C(Cl)=C1 BLEDEFLZKLPBEQ-UHFFFAOYSA-N 0.000 claims 2
- OWOODTQNTSENFQ-UHFFFAOYSA-N 3-[[2-(3-chloro-1-benzothiophen-2-yl)-2-oxoethyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C=1C(NCC(=O)C2=C(C3=CC=CC=C3S2)Cl)=C(C(=O)O)SC=1C1=CC=CC=C1 OWOODTQNTSENFQ-UHFFFAOYSA-N 0.000 claims 2
- DAWJNPJPYFLXJD-UHFFFAOYSA-N 3-[[2-(4-chlorophenyl)-4-ethoxycarbonyl-5-methylfuran-3-yl]sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound CCOC(=O)C1=C(C)OC(C=2C=CC(Cl)=CC=2)=C1S(=O)(=O)NC(=C(S1)C(O)=O)C=C1C1=CC=CC=C1 DAWJNPJPYFLXJD-UHFFFAOYSA-N 0.000 claims 2
- NMCDOMMSRKVLFY-UHFFFAOYSA-N 3-[[2-(4-chlorophenyl)-5-ethoxycarbonyl-4-methyl-1-phenylpyrrol-3-yl]sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C=1C=CC=CC=1N1C(C(=O)OCC)=C(C)C(S(=O)(=O)NC2=C(SC(=C2)C=2C=CC=CC=2)C(O)=O)=C1C1=CC=C(Cl)C=C1 NMCDOMMSRKVLFY-UHFFFAOYSA-N 0.000 claims 2
- LDRYDPQNSLZMCF-UHFFFAOYSA-N 3-[[2-(4-chlorophenyl)acetyl]-prop-2-enylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(CC=C)C(=O)CC1=CC=C(Cl)C=C1 LDRYDPQNSLZMCF-UHFFFAOYSA-N 0.000 claims 2
- VDXBEXLYIUSHDV-UHFFFAOYSA-N 3-[[2-(4-fluorophenyl)acetyl]-methylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C)C(=O)CC1=CC=C(F)C=C1 VDXBEXLYIUSHDV-UHFFFAOYSA-N 0.000 claims 2
- XEBRMGWQOAMEJD-UHFFFAOYSA-N 3-[[2-(4-methoxyphenyl)acetyl]-prop-2-enylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1CC(=O)N(CC=C)C1=C(C(O)=O)SC(C=2C=CC=CC=2)=C1 XEBRMGWQOAMEJD-UHFFFAOYSA-N 0.000 claims 2
- TUKLPSOBBMNHDR-UHFFFAOYSA-N 3-[[2-(chloromethyl)phenyl]sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NS(=O)(=O)C1=CC=CC=C1CCl TUKLPSOBBMNHDR-UHFFFAOYSA-N 0.000 claims 2
- NJIMWAZVNPVZJO-UHFFFAOYSA-N 3-[[2-[2,3-difluoro-4-(trifluoromethyl)phenyl]-2-oxoethyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NCC(=O)C1=CC=C(C(F)(F)F)C(F)=C1F NJIMWAZVNPVZJO-UHFFFAOYSA-N 0.000 claims 2
- FWQDHFBNNXOXCT-UHFFFAOYSA-N 3-[[2-[3-fluoro-4-(trifluoromethyl)phenyl]-2-oxoethyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NCC(=O)C1=CC=C(C(F)(F)F)C(F)=C1 FWQDHFBNNXOXCT-UHFFFAOYSA-N 0.000 claims 2
- IRHZLNLSLIRJBD-UHFFFAOYSA-N 3-[[2-fluoro-4-(trifluoromethyl)benzoyl]-propan-2-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(C(F)(F)F)C=C1F IRHZLNLSLIRJBD-UHFFFAOYSA-N 0.000 claims 2
- WJDRCJKKPZLXQB-UHFFFAOYSA-N 3-[[4-(2,6-dimethylphenyl)piperazine-1-carbonyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound CC1=CC=CC(C)=C1N1CCN(C(=O)NC2=C(SC(=C2)C=2C=CC=CC=2)C(O)=O)CC1 WJDRCJKKPZLXQB-UHFFFAOYSA-N 0.000 claims 2
- INSHPAQZHIADPY-UHFFFAOYSA-N 3-[[4-(2-chlorophenyl)piperazine-1-carbonyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NC(=O)N(CC1)CCN1C1=CC=CC=C1Cl INSHPAQZHIADPY-UHFFFAOYSA-N 0.000 claims 2
- SFGJKHXPKGLQQB-UHFFFAOYSA-N 3-[[4-(3-chlorophenyl)piperazine-1-carbonyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NC(=O)N(CC1)CCN1C1=CC=CC(Cl)=C1 SFGJKHXPKGLQQB-UHFFFAOYSA-N 0.000 claims 2
- RJLMIFSIHQNKIY-UHFFFAOYSA-N 3-[[4-(4-fluorophenyl)piperazine-1-carbonyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NC(=O)N(CC1)CCN1C1=CC=C(F)C=C1 RJLMIFSIHQNKIY-UHFFFAOYSA-N 0.000 claims 2
- VTZBPZJLPDUCKK-UHFFFAOYSA-N 3-[[4-(4-methoxyphenyl)piperazine-1-carbonyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)NC2=C(SC(=C2)C=2C=CC=CC=2)C(O)=O)CC1 VTZBPZJLPDUCKK-UHFFFAOYSA-N 0.000 claims 2
- OETHKSLBGKXPAZ-UHFFFAOYSA-N 3-[[4-(6-methylpyridin-2-yl)piperazine-1-carbonyl]amino]-5-phenylthiophene-2-carboxylic acid;hydrochloride Chemical compound Cl.CC1=CC=CC(N2CCN(CC2)C(=O)NC2=C(SC(=C2)C=2C=CC=CC=2)C(O)=O)=N1 OETHKSLBGKXPAZ-UHFFFAOYSA-N 0.000 claims 2
- HCOZFMWWNGGHPB-UHFFFAOYSA-N 3-[[4-[(4-chlorophenyl)methyl]piperazine-1-carbonyl]amino]-5-phenylthiophene-2-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NC(=O)N(CC1)CCN1CC1=CC=C(Cl)C=C1 HCOZFMWWNGGHPB-UHFFFAOYSA-N 0.000 claims 2
- VNDHIIJYVXDSKW-UHFFFAOYSA-N 3-[[4-fluoro-2-(trifluoromethyl)phenyl]sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NS(=O)(=O)C1=CC=C(F)C=C1C(F)(F)F VNDHIIJYVXDSKW-UHFFFAOYSA-N 0.000 claims 2
- YYXLIDJMVYGKLC-UHFFFAOYSA-N 3-[[4-fluoro-3-(trifluoromethyl)phenyl]sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NS(=O)(=O)C1=CC=C(F)C(C(F)(F)F)=C1 YYXLIDJMVYGKLC-UHFFFAOYSA-N 0.000 claims 2
- XDUOXAFSRZCZJI-UHFFFAOYSA-N 3-[[5-(2-cyanophenyl)thiophen-2-yl]methyl-(2,4-dichlorobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C=1C(=CC(Cl)=CC=1)Cl)CC(S1)=CC=C1C1=CC=CC=C1C#N XDUOXAFSRZCZJI-UHFFFAOYSA-N 0.000 claims 2
- HNXVUHHNOWQZLR-UHFFFAOYSA-N 3-[acetyl(benzyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)C)CC1=CC=CC=C1 HNXVUHHNOWQZLR-UHFFFAOYSA-N 0.000 claims 2
- HZTPLHWWXZOKFZ-UHFFFAOYSA-N 3-[acetyl-[(2,4-difluorophenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)C)CC1=CC=C(F)C=C1F HZTPLHWWXZOKFZ-UHFFFAOYSA-N 0.000 claims 2
- LKWMMBTWAYSOTJ-UHFFFAOYSA-N 3-[acetyl-[(2-methylphenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)C)CC1=CC=CC=C1C LKWMMBTWAYSOTJ-UHFFFAOYSA-N 0.000 claims 2
- HMFDLWQQXACBDV-UHFFFAOYSA-N 3-[acetyl-[(3-methylphenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)C)CC1=CC=CC(C)=C1 HMFDLWQQXACBDV-UHFFFAOYSA-N 0.000 claims 2
- TVTBTXABDRDUES-UHFFFAOYSA-N 3-[acetyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)C)CC1=CC=C(C(F)(F)F)C=C1 TVTBTXABDRDUES-UHFFFAOYSA-N 0.000 claims 2
- CBNMTXJSDJJPAW-UHFFFAOYSA-N 3-[adamantane-1-carbonyl(propan-2-yl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)N(C(C)C)C(=C(S1)C(O)=O)C=C1C1=CC=CC=C1 CBNMTXJSDJJPAW-UHFFFAOYSA-N 0.000 claims 2
- HTWGXQYYFAYRBR-UHFFFAOYSA-N 3-[azepan-4-yl-(2,4-dichlorobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C=1C(=CC(Cl)=CC=1)Cl)C1CCCNCC1 HTWGXQYYFAYRBR-UHFFFAOYSA-N 0.000 claims 2
- XROZTIHRLRCGSU-UHFFFAOYSA-N 3-[benzyl(cyclobutanecarbonyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C1CCC1)CC1=CC=CC=C1 XROZTIHRLRCGSU-UHFFFAOYSA-N 0.000 claims 2
- ZOWIUACTUAUSQT-UHFFFAOYSA-N 3-[benzyl-(2,4-dichlorobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C=1C(=CC(Cl)=CC=1)Cl)CC1=CC=CC=C1 ZOWIUACTUAUSQT-UHFFFAOYSA-N 0.000 claims 2
- RSOWMXDODPAJPL-UHFFFAOYSA-N 3-[benzyl-(2-cyclopentylacetyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)CC1CCCC1)CC1=CC=CC=C1 RSOWMXDODPAJPL-UHFFFAOYSA-N 0.000 claims 2
- IVIPEIJIQJPIGS-UHFFFAOYSA-N 3-[benzyl-(2-methoxyacetyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)COC)CC1=CC=CC=C1 IVIPEIJIQJPIGS-UHFFFAOYSA-N 0.000 claims 2
- SIIMIVJATFOKHR-UHFFFAOYSA-N 3-[benzyl-(4-methylbenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)CC1=CC=CC=C1 SIIMIVJATFOKHR-UHFFFAOYSA-N 0.000 claims 2
- OMMRCJMTUFZTIB-UHFFFAOYSA-N 3-[but-2-enoyl(ethyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(O)=O)=C(N(C(=O)C=CC)CC)C=C1C1=CC=CC=C1 OMMRCJMTUFZTIB-UHFFFAOYSA-N 0.000 claims 2
- NGNARYDCMYVTTQ-UHFFFAOYSA-N 3-[butan-2-yl-(2,4-dichlorobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)CC)C(=O)C1=CC=C(Cl)C=C1Cl NGNARYDCMYVTTQ-UHFFFAOYSA-N 0.000 claims 2
- PWPCCXSZLFVANL-UHFFFAOYSA-N 3-[butanoyl(ethyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(O)=O)=C(N(CC)C(=O)CCC)C=C1C1=CC=CC=C1 PWPCCXSZLFVANL-UHFFFAOYSA-N 0.000 claims 2
- FZCWRHLIMUVHIE-UHFFFAOYSA-N 3-[butanoyl-[(2,4-difluorophenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)CCC)CC1=CC=C(F)C=C1F FZCWRHLIMUVHIE-UHFFFAOYSA-N 0.000 claims 2
- GGQAZFSCGFLISH-UHFFFAOYSA-N 3-[butanoyl-[(2-chlorophenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)CCC)CC1=CC=CC=C1Cl GGQAZFSCGFLISH-UHFFFAOYSA-N 0.000 claims 2
- ZKRAGJZIJANDHJ-UHFFFAOYSA-N 3-[butanoyl-[(2-methylphenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)CCC)CC1=CC=CC=C1C ZKRAGJZIJANDHJ-UHFFFAOYSA-N 0.000 claims 2
- HNWQICAGMFFVLZ-UHFFFAOYSA-N 3-[butanoyl-[(3-chlorophenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)CCC)CC1=CC=CC(Cl)=C1 HNWQICAGMFFVLZ-UHFFFAOYSA-N 0.000 claims 2
- ADVRSLHZOIHULA-UHFFFAOYSA-N 3-[butanoyl-[(3-methoxyphenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)CCC)CC1=CC=CC(OC)=C1 ADVRSLHZOIHULA-UHFFFAOYSA-N 0.000 claims 2
- BKKLZCFDGSSMIM-UHFFFAOYSA-N 3-[butanoyl-[(3-methylphenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)CCC)CC1=CC=CC(C)=C1 BKKLZCFDGSSMIM-UHFFFAOYSA-N 0.000 claims 2
- BURRXABGAUIEFL-UHFFFAOYSA-N 3-[butanoyl-[(4-chlorophenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)CCC)CC1=CC=C(Cl)C=C1 BURRXABGAUIEFL-UHFFFAOYSA-N 0.000 claims 2
- HDZOEJHUIYQKKL-UHFFFAOYSA-N 3-[butanoyl-[(4-methylphenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)CCC)CC1=CC=C(C)C=C1 HDZOEJHUIYQKKL-UHFFFAOYSA-N 0.000 claims 2
- FWVILIXPVUNYKV-UHFFFAOYSA-N 3-[butanoyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)CCC)CC1=CC=C(C(F)(F)F)C=C1 FWVILIXPVUNYKV-UHFFFAOYSA-N 0.000 claims 2
- IYWUNLSGBHHJMS-UHFFFAOYSA-N 3-[cyclobutanecarbonyl-[(2,4-difluorophenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C1CCC1)CC1=CC=C(F)C=C1F IYWUNLSGBHHJMS-UHFFFAOYSA-N 0.000 claims 2
- JPLAPBKPSYSENB-UHFFFAOYSA-N 3-[cyclobutanecarbonyl-[(2-methylphenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound CC1=CC=CC=C1CN(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C(=O)C1CCC1 JPLAPBKPSYSENB-UHFFFAOYSA-N 0.000 claims 2
- FQQRXTXEEOVEHM-UHFFFAOYSA-N 3-[cyclobutanecarbonyl-[(3-methoxyphenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound COC1=CC=CC(CN(C(=O)C2CCC2)C2=C(SC(=C2)C=2C=CC=CC=2)C(O)=O)=C1 FQQRXTXEEOVEHM-UHFFFAOYSA-N 0.000 claims 2
- ZXSGAJYIHJBVCN-UHFFFAOYSA-N 3-[cyclobutanecarbonyl-[(4-methylphenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1CN(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C(=O)C1CCC1 ZXSGAJYIHJBVCN-UHFFFAOYSA-N 0.000 claims 2
- VBYQSVUPQJXJAF-UHFFFAOYSA-N 3-[cyclobutanecarbonyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C1CCC1)CC1=CC=C(C(F)(F)F)C=C1 VBYQSVUPQJXJAF-UHFFFAOYSA-N 0.000 claims 2
- AREJGCOZUYGPKP-UHFFFAOYSA-N 3-[cycloheptanecarbonyl(propan-2-yl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1CCCCCC1 AREJGCOZUYGPKP-UHFFFAOYSA-N 0.000 claims 2
- OYBKJUNDOSLIET-UHFFFAOYSA-N 3-[cyclohex-3-ene-1-carbonyl(propan-2-yl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1CCC=CC1 OYBKJUNDOSLIET-UHFFFAOYSA-N 0.000 claims 2
- JODZOJIVVZXQBC-UHFFFAOYSA-N 3-[cyclohexanecarbonyl(propan-2-yl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1CCCCC1 JODZOJIVVZXQBC-UHFFFAOYSA-N 0.000 claims 2
- JNMLHKVIANKLAW-UHFFFAOYSA-N 3-[cyclohexanecarbonyl-[(2,4-difluorophenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C1CCCCC1)CC1=CC=C(F)C=C1F JNMLHKVIANKLAW-UHFFFAOYSA-N 0.000 claims 2
- KURHJUIVGOCUAP-UHFFFAOYSA-N 3-[cyclohexanecarbonyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C1CCCCC1)CC1=CC=C(C(F)(F)F)C=C1 KURHJUIVGOCUAP-UHFFFAOYSA-N 0.000 claims 2
- TWDZMJGHQPCAEZ-UHFFFAOYSA-N 3-[cyclohexyl-(2,4-dichlorobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C=1C(=CC(Cl)=CC=1)Cl)C1CCCCC1 TWDZMJGHQPCAEZ-UHFFFAOYSA-N 0.000 claims 2
- ARHDRKYFEBMWHM-UHFFFAOYSA-N 3-[cyclohexyl-(4-methylcyclohexanecarbonyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C1CCCCC1 ARHDRKYFEBMWHM-UHFFFAOYSA-N 0.000 claims 2
- TUEGEFDAJMKZMR-UHFFFAOYSA-N 3-[cyclopentyl-(2,4-dichlorobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C=1C(=CC(Cl)=CC=1)Cl)C1CCCC1 TUEGEFDAJMKZMR-UHFFFAOYSA-N 0.000 claims 2
- ZAPVRTUHFZSULH-UHFFFAOYSA-N 3-[cyclopropanecarbonyl-[(3-methylphenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound CC1=CC=CC(CN(C(=O)C2CC2)C2=C(SC(=C2)C=2C=CC=CC=2)C(O)=O)=C1 ZAPVRTUHFZSULH-UHFFFAOYSA-N 0.000 claims 2
- NYCOHEPYGFMHDT-UHFFFAOYSA-N 3-[cyclopropanecarbonyl-[(4-methylphenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1CN(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C(=O)C1CC1 NYCOHEPYGFMHDT-UHFFFAOYSA-N 0.000 claims 2
- REMMRALOHPLDGJ-UHFFFAOYSA-N 3-[cyclopropanecarbonyl-[(4-nitrophenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C1CC1)CC1=CC=C([N+]([O-])=O)C=C1 REMMRALOHPLDGJ-UHFFFAOYSA-N 0.000 claims 2
- OBTPVJJRQIGOEI-UHFFFAOYSA-N 3-[cyclopropanecarbonyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C1CC1)CC1=CC=C(C(F)(F)F)C=C1 OBTPVJJRQIGOEI-UHFFFAOYSA-N 0.000 claims 2
- NIOHTSZBTLGELK-UHFFFAOYSA-N 3-[ethyl(4-methylpentanoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(O)=O)=C(N(C(=O)CCC(C)C)CC)C=C1C1=CC=CC=C1 NIOHTSZBTLGELK-UHFFFAOYSA-N 0.000 claims 2
- JKZZIRPULQQELF-UHFFFAOYSA-N 3-[ethyl(hexanoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(O)=O)=C(N(CC)C(=O)CCCCC)C=C1C1=CC=CC=C1 JKZZIRPULQQELF-UHFFFAOYSA-N 0.000 claims 2
- IDKCAQJAGNTIHF-UHFFFAOYSA-N 3-[ethyl-(4-methylbenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(CC)C(=O)C1=CC=C(C)C=C1 IDKCAQJAGNTIHF-UHFFFAOYSA-N 0.000 claims 2
- LRHXIDOGMBZJFN-UHFFFAOYSA-N 3-[isopropyl(4-methylbenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(C)C=C1 LRHXIDOGMBZJFN-UHFFFAOYSA-N 0.000 claims 2
- ZITWCPNLBDEOGY-UHFFFAOYSA-N 3-[methyl(4-methylpentanoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(O)=O)=C(N(C)C(=O)CCC(C)C)C=C1C1=CC=CC=C1 ZITWCPNLBDEOGY-UHFFFAOYSA-N 0.000 claims 2
- UPXJOAWEWPTOJV-UHFFFAOYSA-N 3-[methyl(naphthalene-2-carbonyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)N(C)C(=C(S1)C(O)=O)C=C1C1=CC=CC=C1 UPXJOAWEWPTOJV-UHFFFAOYSA-N 0.000 claims 2
- NINFPMVAAVXRND-UHFFFAOYSA-N 3-[methyl(pent-4-enoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(O)=O)=C(N(C(=O)CCC=C)C)C=C1C1=CC=CC=C1 NINFPMVAAVXRND-UHFFFAOYSA-N 0.000 claims 2
- RWQSABWWSQCRRJ-UHFFFAOYSA-N 3-[methyl(pentanoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(O)=O)=C(N(C)C(=O)CCCC)C=C1C1=CC=CC=C1 RWQSABWWSQCRRJ-UHFFFAOYSA-N 0.000 claims 2
- OVULPYHHDRCPFX-UHFFFAOYSA-N 3-[methyl(thiophene-2-carbonyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C)C(=O)C1=CC=CS1 OVULPYHHDRCPFX-UHFFFAOYSA-N 0.000 claims 2
- JNWCUCLQFPDAPJ-UHFFFAOYSA-N 3-[methyl-(2,4,6-trifluorobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C)C(=O)C1=C(F)C=C(F)C=C1F JNWCUCLQFPDAPJ-UHFFFAOYSA-N 0.000 claims 2
- UAPOZRAWZJWLGO-UHFFFAOYSA-N 3-[methyl-(2-phenylacetyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C)C(=O)CC1=CC=CC=C1 UAPOZRAWZJWLGO-UHFFFAOYSA-N 0.000 claims 2
- MGBLEYRIOYMJIN-UHFFFAOYSA-N 3-[methyl-(4-methyl-3-nitrobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C)C(=O)C1=CC=C(C)C([N+]([O-])=O)=C1 MGBLEYRIOYMJIN-UHFFFAOYSA-N 0.000 claims 2
- DPQPHJGUMVATDP-UHFFFAOYSA-N 3-[methyl-(4-methylbenzoyl)amino]-5-(2-methylphenyl)thiophene-2-carboxylic acid Chemical compound C1=C(C=2C(=CC=CC=2)C)SC(C(O)=O)=C1N(C)C(=O)C1=CC=C(C)C=C1 DPQPHJGUMVATDP-UHFFFAOYSA-N 0.000 claims 2
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- 229940051021 yellow-fever virus Drugs 0.000 description 1
Classifications
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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
- C07D409/02—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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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
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- 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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- 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
- A61P31/14—Antivirals for RNA viruses
-
- 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
-
- 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
- C07D409/02—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
- C07D409/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D409/02—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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
- C07D419/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D471/10—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Gastroenterology & Hepatology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29673101P | 2001-06-11 | 2001-06-11 | |
| PCT/CA2002/000876 WO2002100851A2 (en) | 2001-06-11 | 2002-06-11 | Thiophene derivatives as antiviral agents for flavivirus infection |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200400022A1 EA200400022A1 (ru) | 2004-06-24 |
| EA007484B1 true EA007484B1 (ru) | 2006-10-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200400022A EA007484B1 (ru) | 2001-06-11 | 2002-06-11 | Соединения и способы лечения или предупреждения инфекций flavivirus |
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| EP (3) | EP2363396A1 (enExample) |
| JP (2) | JP4544857B2 (enExample) |
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| CY (1) | CY1109497T1 (enExample) |
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| PT (1) | PT1401825E (enExample) |
| SI (1) | SI1401825T1 (enExample) |
| SK (1) | SK288015B6 (enExample) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2472791C2 (ru) * | 2008-08-27 | 2013-01-20 | КалсиМедика Инк. | Соединения, модулирующие внутриклеточный кальций |
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| EA007484B1 (ru) * | 2001-06-11 | 2006-10-27 | Вирокем Фарма Инк. | Соединения и способы лечения или предупреждения инфекций flavivirus |
| US8329924B2 (en) * | 2001-06-11 | 2012-12-11 | Vertex Pharmaceuticals (Canada) Incorporated | Compounds and methods for the treatment or prevention of Flavivirus infections |
| EP2335700A1 (en) | 2001-07-25 | 2011-06-22 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis C virus polymerase inhibitors with a heterobicylic structure |
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| US7179836B2 (en) * | 2002-09-20 | 2007-02-20 | Smithkline Beecham Corporation | Chemical compounds |
| TW200418863A (en) * | 2002-10-17 | 2004-10-01 | Upjohn Co | Novel anthelmintic and insecticidal compositions |
| US20050075279A1 (en) | 2002-10-25 | 2005-04-07 | Boehringer Ingelheim International Gmbh | Macrocyclic peptides active against the hepatitis C virus |
| PT1569929E (pt) * | 2002-12-10 | 2010-06-18 | Virochem Pharma Inc | Compostos e métodos para o tratamento ou prevenção de infecções por flavivírus |
| US20040192707A1 (en) * | 2002-12-10 | 2004-09-30 | Laval Chan Chun Kong | Compounds and methods for the treatment or prevention of Flavivirus infections |
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| SE0300092D0 (sv) * | 2003-01-15 | 2003-01-15 | Astrazeneca Ab | Novel compounds |
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| DE10359791A1 (de) * | 2003-12-19 | 2005-07-21 | Bayer Healthcare Ag | Substituierte Thiophene |
| GB0500020D0 (en) | 2005-01-04 | 2005-02-09 | Novartis Ag | Organic compounds |
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| DE102004061746A1 (de) * | 2004-12-22 | 2006-07-06 | Bayer Healthcare Ag | Alkinyl-substituierte Thiophene |
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