SG181423A1 - Novel antiviral compounds - Google Patents
Novel antiviral compounds Download PDFInfo
- Publication number
- SG181423A1 SG181423A1 SG2012035002A SG2012035002A SG181423A1 SG 181423 A1 SG181423 A1 SG 181423A1 SG 2012035002 A SG2012035002 A SG 2012035002A SG 2012035002 A SG2012035002 A SG 2012035002A SG 181423 A1 SG181423 A1 SG 181423A1
- Authority
- SG
- Singapore
- Prior art keywords
- heterocycle
- alkyl
- alkenyl
- alkynyl
- heteroalkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 345
- 230000000840 anti-viral effect Effects 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 129
- 239000004480 active ingredient Substances 0.000 claims abstract description 41
- 239000003814 drug Substances 0.000 claims abstract description 36
- 238000011282 treatment Methods 0.000 claims abstract description 36
- 208000036142 Viral infection Diseases 0.000 claims abstract description 26
- 230000009385 viral infection Effects 0.000 claims abstract description 26
- 241001465754 Metazoa Species 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- -1 cycloalkynyl Chemical group 0.000 claims description 167
- 125000000217 alkyl group Chemical group 0.000 claims description 102
- 125000003118 aryl group Chemical group 0.000 claims description 92
- 125000003342 alkenyl group Chemical group 0.000 claims description 77
- 125000000304 alkynyl group Chemical group 0.000 claims description 75
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 70
- 125000000623 heterocyclic group Chemical group 0.000 claims description 66
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 42
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 19
- 241000124008 Mammalia Species 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 230000002265 prevention Effects 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 208000015181 infectious disease Diseases 0.000 claims description 5
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- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000005670 ethenylalkyl group Chemical group 0.000 claims description 3
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- 230000010076 replication Effects 0.000 abstract description 8
- 230000001225 therapeutic effect Effects 0.000 abstract description 7
- 208000031886 HIV Infections Diseases 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 5
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- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 abstract description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 92
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 52
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- 239000012535 impurity Substances 0.000 description 38
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 26
- JIYXANPMCJRVKB-UHFFFAOYSA-N methyl 2-(2-tert-butyl-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)pentanoate Chemical compound ClC1=C(C(C(=O)OC)CCC)C(C)=NC2=CC(C(C)(C)C)=NN21 JIYXANPMCJRVKB-UHFFFAOYSA-N 0.000 description 25
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 229940002612 prodrug Drugs 0.000 description 18
- 239000000651 prodrug Substances 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 125000001183 hydrocarbyl group Chemical group 0.000 description 17
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 16
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- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 12
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- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
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- YAEFVUSJQYXMGL-UHFFFAOYSA-N methyl 2-(2-tert-butyl-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-3-phenylpropanoate Chemical compound CC1=NC2=CC(C(C)(C)C)=NN2C(Cl)=C1C(C(=O)OC)CC1=CC=CC=C1 YAEFVUSJQYXMGL-UHFFFAOYSA-N 0.000 description 2
- PAFJCJIARXBJOR-UHFFFAOYSA-N methyl 2-(2-tert-butyl-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-4-methoxybutanoate Chemical compound ClC1=C(C(C(=O)OC)CCOC)C(C)=NC2=CC(C(C)(C)C)=NN21 PAFJCJIARXBJOR-UHFFFAOYSA-N 0.000 description 2
- HINHPWLZFLHHNE-UHFFFAOYSA-N methyl 2-(2-tert-butyl-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate Chemical compound ClC1=C(CC(=O)OC)C(C)=NC2=CC(C(C)(C)C)=NN21 HINHPWLZFLHHNE-UHFFFAOYSA-N 0.000 description 2
- NWDKOIBKPJFCEA-UHFFFAOYSA-N methyl 2-(5-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-6-yl)pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC=NN2C=1C1=CC=CC=C1 NWDKOIBKPJFCEA-UHFFFAOYSA-N 0.000 description 2
- IIBYTDPCPGBVPV-UHFFFAOYSA-N methyl 2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetate Chemical compound N=1N2C(Cl)=C(CC(=O)OC)C(C)=NC2=CC=1C1=CC=CC=C1 IIBYTDPCPGBVPV-UHFFFAOYSA-N 0.000 description 2
- HAALVARHZCYMTB-UHFFFAOYSA-N methyl 2-(7-chloro-5-methyl-2-propan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate Chemical compound ClC1=C(CC(=O)OC)C(C)=NC2=NC(C(C)C)=NN21 HAALVARHZCYMTB-UHFFFAOYSA-N 0.000 description 2
- AYXLLICAKRTTTG-UHFFFAOYSA-N methyl 2-(7-chloro-5-methyl-2-propylpyrazolo[1,5-a]pyrimidin-6-yl)acetate Chemical compound N1=C(C)C(CC(=O)OC)=C(Cl)N2N=C(CCC)C=C21 AYXLLICAKRTTTG-UHFFFAOYSA-N 0.000 description 2
- VVABMSDTZMVZCJ-UHFFFAOYSA-N methyl 2-(7-chloro-5-methyl-2-propylpyrazolo[1,5-a]pyrimidin-6-yl)pentanoate Chemical compound ClC1=C(C(C(=O)OC)CCC)C(C)=NC2=CC(CCC)=NN21 VVABMSDTZMVZCJ-UHFFFAOYSA-N 0.000 description 2
- HDLZVBCVICISHZ-UHFFFAOYSA-N methyl 2-[2,3,5-trimethyl-7-(4-methylphenyl)imidazo[4,5-b]pyridin-6-yl]acetate Chemical compound COC(=O)CC1=C(C)N=C2N(C)C(C)=NC2=C1C1=CC=C(C)C=C1 HDLZVBCVICISHZ-UHFFFAOYSA-N 0.000 description 2
- HCBLVKLGYJFXNV-UHFFFAOYSA-N methyl 2-[2,3,5-trimethyl-7-(4-methylphenyl)imidazo[4,5-b]pyridin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C1=C(C)N=C2N(C)C(C)=NC2=C1C1=CC=C(C)C=C1 HCBLVKLGYJFXNV-UHFFFAOYSA-N 0.000 description 2
- DPGMIZSZOFBNHX-UHFFFAOYSA-N methyl 2-[2-(furan-2-yl)-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C=3OC=CC=3)=NN2C=1C1=CC=C(C)C=C1 DPGMIZSZOFBNHX-UHFFFAOYSA-N 0.000 description 2
- BGFPXTUNUQXKNS-UHFFFAOYSA-N methyl 2-[2-tert-butyl-3,5-dimethyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=C(C)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 BGFPXTUNUQXKNS-UHFFFAOYSA-N 0.000 description 2
- WWCVLBMDGVZPNV-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(1-methylindol-5-yl)pyrazolo[1,5-a]pyrimidin-6-yl]-3-phenylpropanoate Chemical compound CC1=NC2=CC(C(C)(C)C)=NN2C(C=2C=C3C=CN(C)C3=CC=2)=C1C(C(=O)OC)CC1=CC=CC=C1 WWCVLBMDGVZPNV-UHFFFAOYSA-N 0.000 description 2
- MYQHCKCFNXRNQN-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(1-methylindol-6-yl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound C1=C2C=CN(C)C2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(=O)OC)CCC)C(C)(C)C)=C1 MYQHCKCFNXRNQN-UHFFFAOYSA-N 0.000 description 2
- SUKUSZPNGOMXCX-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]-4-methoxybutanoate Chemical compound COCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 SUKUSZPNGOMXCX-UHFFFAOYSA-N 0.000 description 2
- LGHWMYXWYMFLPH-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(4-propan-2-ylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C(C)C)C=C1 LGHWMYXWYMFLPH-UHFFFAOYSA-N 0.000 description 2
- HBTXVKUHLOUXIR-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C(F)(F)F)C=C1 HBTXVKUHLOUXIR-UHFFFAOYSA-N 0.000 description 2
- ZAAZXLHULCOWAF-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(1h-indol-5-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound C1=C2NC=CC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(=O)OC)CCC)C(C)(C)C)=C1 ZAAZXLHULCOWAF-UHFFFAOYSA-N 0.000 description 2
- QIGJMKVCGDFVCF-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2,3-dihydro-1-benzofuran-5-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound C1=C2OCCC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(=O)OC)CCC)C(C)(C)C)=C1 QIGJMKVCGDFVCF-UHFFFAOYSA-N 0.000 description 2
- YIVMGSBHAMMRJM-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2,4-difluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(F)C=C1F YIVMGSBHAMMRJM-UHFFFAOYSA-N 0.000 description 2
- BYWLQYDDMNAOIO-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2,4-dimethylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1C BYWLQYDDMNAOIO-UHFFFAOYSA-N 0.000 description 2
- CZKGLBDANODSRF-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2-chloro-4-methylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1Cl CZKGLBDANODSRF-UHFFFAOYSA-N 0.000 description 2
- LALWJPNZMRVJGW-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2-fluoro-4-methoxyphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(OC)C=C1F LALWJPNZMRVJGW-UHFFFAOYSA-N 0.000 description 2
- XVFMHYAIDHRUNX-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2-fluoro-4-methylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1F XVFMHYAIDHRUNX-UHFFFAOYSA-N 0.000 description 2
- QATOMVKYNAQJHE-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(3,4-dihydro-2h-1,5-benzodioxepin-7-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound O1CCCOC2=CC(C=3N4N=C(C=C4N=C(C)C=3C(C(=O)OC)CCC)C(C)(C)C)=CC=C21 QATOMVKYNAQJHE-UHFFFAOYSA-N 0.000 description 2
- PBVUFXFSCIBPFM-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(3,4-dihydro-2h-chromen-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound O1CCCC2=CC(C=3N4N=C(C=C4N=C(C)C=3C(C(=O)OC)CCC)C(C)(C)C)=CC=C21 PBVUFXFSCIBPFM-UHFFFAOYSA-N 0.000 description 2
- ZVIIAYXMQYBWRR-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(4-chloro-2-methoxyphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(Cl)C=C1OC ZVIIAYXMQYBWRR-UHFFFAOYSA-N 0.000 description 2
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- MWZMBQOCFUAUJT-UHFFFAOYSA-N methyl 2-[5-methyl-7-(4-methylphenyl)-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C=3C=CC=CC=3)=NN2C=1C1=CC=C(C)C=C1 MWZMBQOCFUAUJT-UHFFFAOYSA-N 0.000 description 2
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- KKRYDPVDJYCEER-QEGGNFSNSA-N tert-butyl n-[(2s,3r)-3-hydroxy-4-[[(2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]amino]-1-phenylbutan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)[C@H](O)CNC[C@@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OC(C)(C)C)C1=CC=CC=C1 KKRYDPVDJYCEER-QEGGNFSNSA-N 0.000 description 1
- DZUIFTBFVIXAMZ-YHKVADFHSA-N tert-butyl n-[(2s,3s,5r)-3-hydroxy-5-[(4-methoxyphenyl)methyl]-6-[[(2s)-3-methyl-1-[[(2s)-1-morpholin-4-yl-1-oxo-3-phenylpropan-2-yl]amino]-1-oxobutan-2-yl]amino]-6-oxo-1-phenylhexan-2-yl]carbamate Chemical compound C1=CC(OC)=CC=C1C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1CCOCC1)C[C@H](O)[C@@H](NC(=O)OC(C)(C)C)CC1=CC=CC=C1 DZUIFTBFVIXAMZ-YHKVADFHSA-N 0.000 description 1
- NAJDZKGRZBLNON-RKGCBODKSA-N tert-butyl n-[(2s,3s,5r)-5-benzyl-3-hydroxy-6-[[(2s)-3-methyl-1-[[(2s)-1-morpholin-4-yl-1-oxo-3-phenylpropan-2-yl]amino]-1-oxobutan-2-yl]amino]-6-oxo-1-phenylhexan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C[C@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1CCOCC1)CC=1C=CC=CC=1)NC(=O)OC(C)(C)C)C1=CC=CC=C1 NAJDZKGRZBLNON-RKGCBODKSA-N 0.000 description 1
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- 229960000838 tipranavir Drugs 0.000 description 1
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- 231100000440 toxicity profile Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
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- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Public Health (AREA)
- General Health & Medical Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| GBGB1001204.5A GB201001204D0 (en) | 2010-01-26 | 2010-01-26 | Novel antiviral compounds |
| PCT/EP2010/070306 WO2011076765A1 (en) | 2009-12-23 | 2010-12-20 | Novel antiviral compounds |
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| GB0913636D0 (en) | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| EA201291300A1 (ru) | 2010-07-02 | 2013-06-28 | Джилид Сайэнс, Инк. | Производные нафт-2-илуксусной кислоты для лечения спида |
| JP5806735B2 (ja) | 2010-07-02 | 2015-11-10 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｉｖ抗ウイルス化合物としての２−キノリニル−酢酸誘導体 |
| US8633200B2 (en) | 2010-09-08 | 2014-01-21 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| WO2012066442A1 (en) | 2010-11-15 | 2012-05-24 | Pfizer Limited | Inhibitors of hiv replication |
| AU2011331301A1 (en) | 2010-11-15 | 2013-05-23 | Katholieke Universiteit Leuven | Antiviral condensed heterocyclic compounds |
| EP2511273B8 (en) | 2011-04-15 | 2019-06-26 | Hivih | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
| ES2615734T3 (es) | 2011-04-21 | 2017-06-08 | Gilead Sciences, Inc. | Compuestos de benzotiazol y su uso farmacéutico |
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| EP2772480B2 (en) | 2011-10-25 | 2020-12-09 | Shionogi & Co., Ltd. | Hiv replication inhibitor |
| CA2858096C (en) * | 2011-12-22 | 2020-06-23 | Gilead Sciences, Inc. | Pyrazolo[1,5-a]pyrimidines as antiviral agents |
| US9284323B2 (en) | 2012-01-04 | 2016-03-15 | Gilead Sciences, Inc. | Naphthalene acetic acid derivatives against HIV infection |
| US9376392B2 (en) | 2012-01-04 | 2016-06-28 | Gilead Sciences, Inc. | 2-(tert-butoxy)-2-(7-methylquinolin-6-yl) acetic acid derivatives for treating AIDS |
| US8629276B2 (en) | 2012-02-15 | 2014-01-14 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| US9034882B2 (en) * | 2012-03-05 | 2015-05-19 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
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| PE20141558A1 (es) | 2012-04-20 | 2014-11-06 | Gilead Sciences Inc | Derivados de acido benzotiazol-6-il acetico y su uso para tratar una infeccion por vih |
| US8906929B2 (en) | 2012-08-16 | 2014-12-09 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| EP2719685A1 (en) | 2012-10-11 | 2014-04-16 | Laboratoire Biodim | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
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| EP2970301B1 (en) | 2013-03-13 | 2017-01-11 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
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| WO2014164409A1 (en) | 2013-03-13 | 2014-10-09 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| JP2016512558A (ja) | 2013-03-14 | 2016-04-28 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | ヒト免疫不全ウイルス複製の阻害剤 |
| JP6268656B2 (ja) | 2013-03-14 | 2018-01-31 | ビーブ・ヘルスケア・ユーケイ・（ナンバー５）・リミテッドＶｉｉＶ Ｈｅａｌｔｈｃａｒｅ ＵＫ （Ｎｏ．５） Ｌｉｍｉｔｅｄ | ヒト免疫不全ウイルス複製の阻害剤 |
| EP2821082A1 (en) | 2013-07-05 | 2015-01-07 | Laboratoire Biodim | Method of producing an inactivated lentivirus, especially HIV, vaccine, kit and method of use |
| WO2015119249A1 (ja) | 2014-02-07 | 2015-08-13 | 国立大学法人東京医科歯科大学 | 筋形成促進剤、筋萎縮抑制剤、医薬組成物及びｔａｚ活性化剤 |
| US9932356B2 (en) | 2014-02-12 | 2018-04-03 | Viiv Healthcare Uk (No. 5) Limited | Pyrazolopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
| PT3105236T (pt) | 2014-02-12 | 2017-12-22 | Viiv Healthcare Uk (No 5) Ltd | Macrociclos de benzotiazole como inibidores da replicação do vírus da imunodeficiência humana |
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| ES2687322T3 (es) | 2014-02-19 | 2018-10-24 | VIIV Healthcare UK (No.5) Limited | Inhibidores de la replicación del virus de inmunodeficiencia humana |
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| WO2015127003A1 (en) | 2014-02-20 | 2015-08-27 | Bristol-Myers Squibb Company | Pyridin-3-yl acetic acid macrocycles as inhibitors of human immunodeficiency virus replication |
| US9193720B2 (en) | 2014-02-20 | 2015-11-24 | Bristol-Myers Squibb Company | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| EP3144311A4 (en) | 2014-05-16 | 2018-01-03 | Shionogi & Co., Ltd. | Tricyclic heterocyclic derivative having hiv replication-inhibiting effect |
| KR101692478B1 (ko) | 2014-07-10 | 2017-01-05 | 계명대학교 산학협력단 | Ｓｙ０２９를 유효성분으로 함유하는 항바이러스 조성물 |
| AU2016271762B2 (en) | 2015-05-29 | 2020-01-23 | Shionogi & Co., Ltd. | Nitrogen-containing tricyclic derivatives having HIV replication inhibitory activity |
| CN107820493A (zh) | 2015-07-06 | 2018-03-20 | Viiv保健英国第五有限公司 | 作为人类免疫缺陷性病毒复制的抑制剂的吡啶‑3‑基乙酸衍生物 |
| WO2017006260A1 (en) | 2015-07-08 | 2017-01-12 | VIIV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| AU2016290986A1 (en) | 2015-07-09 | 2018-01-18 | VIIV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| RU2018103031A (ru) | 2015-07-09 | 2019-08-09 | ВАЙВ ХЕЛТКЕР ЮКей (N5) ЛИМИТЕД | Производные пиридин-3-ил уксусной кислоты в качестве ингибиторов репликации вируса иммунодефицита человека |
| KR20180035910A (ko) | 2015-08-07 | 2018-04-06 | 비브 헬스케어 유케이 (넘버5) 리미티드 | 인간 면역결핍 바이러스 복제의 억제제로서 피리딘-3-일 아세트산 유도체 |
| CN108026113A (zh) | 2015-08-10 | 2018-05-11 | Viiv保健英国第五有限公司 | 作为人免疫缺陷病毒复制的抑制剂的咪唑并吡啶大环类化合物 |
| AR105653A1 (es) | 2015-08-11 | 2017-10-25 | VIIV HEALTHCARE UK (Nº 5) LTD | Derivados del ácido 5-(n-bencil-tetrahidroisoquinolin-6-il)-piridin-3-il acético como inhibidores de la replicación del virus de la inmunodeficiencia humana |
| TW201718537A (zh) | 2015-08-12 | 2017-06-01 | Ｖｉｉｖ醫療保健英國（Ｎｏ．５）有限公司 | 做為人類免疫缺陷病毒複製抑制劑之吡啶－３－基乙酸衍生物 |
| US10577353B2 (en) | 2015-08-12 | 2020-03-03 | VIIV Healthcare UK (No.5) Limited | 5-(n-[6,5]-fused bicyclic aryl tetrahydroisoquinolin-6-yl) pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| CA2995087A1 (en) | 2015-08-12 | 2017-02-16 | John F. Kadow | 5-(n-fused tricyclic aryl tetrahydroisoquinolin-6-yl) pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| CN108368093A (zh) | 2015-08-20 | 2018-08-03 | Viiv保健英国第五有限公司 | 作为人免疫缺陷病毒复制的抑制剂的吡啶-3-基乙酸衍生物 |
| WO2017195113A1 (en) | 2016-05-11 | 2017-11-16 | VIIV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| EP3455214A1 (en) | 2016-05-11 | 2019-03-20 | ViiV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| EP3455217A1 (en) | 2016-05-11 | 2019-03-20 | ViiV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| JP2020503348A (ja) | 2017-01-03 | 2020-01-30 | ヴィーブ ヘルスケア ユーケー（ナンバー５）リミテッド | ヒト免疫不全ウイルス複製の阻害剤としてのピリジン−３−イル酢酸誘導体 |
| US20200016136A1 (en) | 2017-01-03 | 2020-01-16 | Viiv Healthcare Uk (No. 5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| WO2019244066A2 (en) | 2018-06-19 | 2019-12-26 | VIIV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| WO2020003093A1 (en) | 2018-06-25 | 2020-01-02 | VIIV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
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| DE69130683T2 (de) * | 1991-04-22 | 1999-05-06 | Otsuka Pharmaceutical Factory, Inc., Naruto, Tokushima | PYRAZOLO[1,5-a]PYRIMIDINDERIVATE UND SIE ENTHALTENDE ANTIINFLAMMATORISCHE MITTEL |
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| CN1659143A (zh) * | 2001-03-01 | 2005-08-24 | 盐野义制药株式会社 | 具有hiv整合酶抑制活性的含氮杂芳基化合物 |
| JP2003171381A (ja) | 2001-09-25 | 2003-06-20 | Takeda Chem Ind Ltd | エントリー阻害剤 |
| JP2003119137A (ja) | 2001-10-10 | 2003-04-23 | Japan Tobacco Inc | Ｈｉｖ阻害剤 |
| CA2463975A1 (en) | 2001-10-26 | 2003-05-01 | Maria Emilia Di Francesco | Dihydroxypyrimidine carboxamide inhibitors of hiv integrase |
| JP4497347B2 (ja) | 2001-12-05 | 2010-07-07 | 塩野義製薬株式会社 | Ｈｉｖインテグラーゼ阻害活性を有する誘導体 |
| PL370664A1 (en) | 2001-12-12 | 2005-05-30 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| EA009556B1 (ru) | 2001-12-21 | 2008-02-28 | Тиботек Фармасьютикалз Лтд. | Гетероциклические замещённые фенилсодержащие сульфонамиды широкого спектра действия в качестве ингибиторов протеазы вич |
| ATE370948T1 (de) | 2002-01-17 | 2007-09-15 | Merck & Co Inc | Hydroxynaphthyridinoncarbonsäureamide, die sich als inhibitoren der hiv-integrase eignen |
| TW200306192A (en) | 2002-01-18 | 2003-11-16 | Bristol Myers Squibb Co | Tricyclic 2-pyrimidone compounds useful as HIV reverse transcriptase inhibitors |
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| PA8586801A1 (es) | 2002-10-31 | 2005-02-04 | Pfizer | Inhibidores de hiv-integrasa, composiciones farmaceuticas y metodos para su uso |
| ES2463720T3 (es) * | 2007-11-16 | 2014-05-29 | Gilead Sciences, Inc. | Inhibidores de la replicación del virus de inmunodeficiencia humana |
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2010
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- 2010-12-20 AU AU2010334958A patent/AU2010334958B2/en not_active Ceased
- 2010-12-20 US US13/518,434 patent/US20120316161A1/en not_active Abandoned
- 2010-12-20 SG SG2012035002A patent/SG181423A1/en unknown
- 2010-12-20 SG SG10201408512RA patent/SG10201408512RA/en unknown
- 2010-12-20 CN CN201080064636.2A patent/CN102770181B/zh not_active Expired - Fee Related
- 2010-12-20 KR KR1020127019420A patent/KR101483834B1/ko not_active Expired - Fee Related
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- 2010-12-20 CA CA2781780A patent/CA2781780C/en not_active Expired - Fee Related
- 2010-12-20 JP JP2012545282A patent/JP2013515692A/ja not_active Ceased
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- 2010-12-20 EP EP10801407.7A patent/EP2516008B1/en not_active Not-in-force
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2012
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| US20120316161A1 (en) | 2012-12-13 |
| SG10201408512RA (en) | 2015-02-27 |
| KR101483834B1 (ko) | 2015-01-16 |
| KR20120106869A (ko) | 2012-09-26 |
| MX2012007410A (es) | 2012-07-17 |
| AU2010334958A1 (en) | 2012-06-07 |
| ES2475970T3 (es) | 2014-07-11 |
| CN102770181B (zh) | 2015-08-12 |
| EP2516008B1 (en) | 2014-04-16 |
| WO2011076765A1 (en) | 2011-06-30 |
| IL219965A0 (en) | 2012-07-31 |
| CA2781780C (en) | 2015-02-17 |
| EP2516008A1 (en) | 2012-10-31 |
| JP2013515692A (ja) | 2013-05-09 |
| AU2010334958B2 (en) | 2015-02-05 |
| CA2781780A1 (en) | 2011-06-30 |
| CN102770181A (zh) | 2012-11-07 |
| PT2516008E (pt) | 2014-07-16 |
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