CA2781780C - Novel antiviral compounds - Google Patents
Novel antiviral compounds Download PDFInfo
- Publication number
- CA2781780C CA2781780C CA2781780A CA2781780A CA2781780C CA 2781780 C CA2781780 C CA 2781780C CA 2781780 A CA2781780 A CA 2781780A CA 2781780 A CA2781780 A CA 2781780A CA 2781780 C CA2781780 C CA 2781780C
- Authority
- CA
- Canada
- Prior art keywords
- heterocycle
- pyrimidin
- methyl
- butyl
- tert
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 337
- 230000000840 anti-viral effect Effects 0.000 title claims abstract description 17
- 239000004480 active ingredient Substances 0.000 claims abstract description 41
- 239000003814 drug Substances 0.000 claims abstract description 35
- 238000011282 treatment Methods 0.000 claims abstract description 34
- 208000036142 Viral infection Diseases 0.000 claims abstract description 25
- 230000009385 viral infection Effects 0.000 claims abstract description 25
- 241001465754 Metazoa Species 0.000 claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- -1 cycloalkynyl Chemical group 0.000 claims description 175
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- 125000003118 aryl group Chemical group 0.000 claims description 92
- 125000003342 alkenyl group Chemical group 0.000 claims description 78
- 125000000304 alkynyl group Chemical group 0.000 claims description 75
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 71
- 125000000623 heterocyclic group Chemical group 0.000 claims description 68
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 60
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 46
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 42
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 33
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical compound CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 claims description 31
- 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 22
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 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 12
- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 241000282414 Homo sapiens Species 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 5
- POVQFRGZEOXEMF-UHFFFAOYSA-N methyl 2-[2-tert-butyl-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(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 POVQFRGZEOXEMF-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- QUSAOLLZLPDHEQ-UHFFFAOYSA-N ethyl 2-[3-bromo-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCOC(=O)C(CCC)C=1C(C)=NC2=C(Br)C=NN2C=1C1=CC=C(C)C=C1 QUSAOLLZLPDHEQ-UHFFFAOYSA-N 0.000 claims description 4
- JHVUPJUOIKNTPW-UHFFFAOYSA-N ethyl 2-[5-methyl-3,7-bis(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCOC(=O)C(CCC)C=1C(C)=NC2=C(C=3C=CC(C)=CC=3)C=NN2C=1C1=CC=C(C)C=C1 JHVUPJUOIKNTPW-UHFFFAOYSA-N 0.000 claims description 4
- YGQGTOXSJMHZIZ-UHFFFAOYSA-N methyl 2-(2-tert-butyl-5-methyl-7-phenylpyrazolo[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=CC=C1 YGQGTOXSJMHZIZ-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- GJXMOQMXFPCOQR-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-3,7-bis(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=C(C=3C=CC(C)=CC=3)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 GJXMOQMXFPCOQR-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- QXYMFGVVBYBHKT-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(1h-indol-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound C1=C2C=CNC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(=O)OC)CCC)C(C)(C)C)=C1 QXYMFGVVBYBHKT-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- AGVUOHNRUOYKDE-UHFFFAOYSA-N methyl 2-[3-bromo-2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=C(Br)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 AGVUOHNRUOYKDE-UHFFFAOYSA-N 0.000 claims description 4
- MAVKSWHJEIALLC-UHFFFAOYSA-N methyl 2-[5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC=NN2C=1C1=CC=C(C)C=C1 MAVKSWHJEIALLC-UHFFFAOYSA-N 0.000 claims description 4
- GTMLZIMJDIHAIS-UHFFFAOYSA-N methyl 2-[7-(1-benzothiophen-5-yl)-2-tert-butyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound C1=C2SC=CC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(=O)OC)CCC)C(C)(C)C)=C1 GTMLZIMJDIHAIS-UHFFFAOYSA-N 0.000 claims description 4
- GSEUORTVIRNJCF-UHFFFAOYSA-N 2-(2-tert-butyl-5-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-6-yl)pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=CC=C1 GSEUORTVIRNJCF-UHFFFAOYSA-N 0.000 claims description 3
- QTGMDJQPQJZPCJ-UHFFFAOYSA-N 2-[2-tert-butyl-5-methyl-7-(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CN1CCOC2=CC(C=3N4N=C(C=C4N=C(C)C=3C(C(O)=O)CCC)C(C)(C)C)=CC=C21 QTGMDJQPQJZPCJ-UHFFFAOYSA-N 0.000 claims description 3
- JIXSLXQANJHEQK-UHFFFAOYSA-N 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]-3-methylpentanoic acid Chemical compound CCC(C)C(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 JIXSLXQANJHEQK-UHFFFAOYSA-N 0.000 claims description 3
- BUGIZCIFXVQKGG-UHFFFAOYSA-N 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 BUGIZCIFXVQKGG-UHFFFAOYSA-N 0.000 claims description 3
- ZZZPSBBGMPEYKV-UHFFFAOYSA-N 2-[2-tert-butyl-7-(2,3-dihydro-1-benzofuran-5-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound C1=C2OCCC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(O)=O)CCC)C(C)(C)C)=C1 ZZZPSBBGMPEYKV-UHFFFAOYSA-N 0.000 claims description 3
- BMJLQTJBBNAFHT-UHFFFAOYSA-N 2-[2-tert-butyl-7-(3,4-dihydro-2h-1,5-benzodioxepin-7-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound O1CCCOC2=CC(C=3N4N=C(C=C4N=C(C)C=3C(C(O)=O)CCC)C(C)(C)C)=CC=C21 BMJLQTJBBNAFHT-UHFFFAOYSA-N 0.000 claims description 3
- WYDPKMYIIGPYBC-UHFFFAOYSA-N 2-[2-tert-butyl-7-(3-hydroxyphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=CC(O)=C1 WYDPKMYIIGPYBC-UHFFFAOYSA-N 0.000 claims description 3
- OHXRLTSMBAXVNE-UHFFFAOYSA-N 2-[2-tert-butyl-7-(4-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(Cl)C=C1 OHXRLTSMBAXVNE-UHFFFAOYSA-N 0.000 claims description 3
- ONQHPVAZJKYJAB-UHFFFAOYSA-N 2-[5-methyl-7-(4-methylphenyl)-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C=3C=CC=CC=3)=NN2C=1C1=CC=C(C)C=C1 ONQHPVAZJKYJAB-UHFFFAOYSA-N 0.000 claims description 3
- VKHOVVKPMJVDLH-UHFFFAOYSA-N 2-[5-methyl-7-(4-methylphenyl)-2-propylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(CCC)=NN2C=1C1=CC=C(C)C=C1 VKHOVVKPMJVDLH-UHFFFAOYSA-N 0.000 claims description 3
- KCIOXZSEIBKUGN-UHFFFAOYSA-N 2-[5-methyl-7-(4-methylphenyl)-3-phenylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=C(C=3C=CC=CC=3)C=NN2C=1C1=CC=C(C)C=C1 KCIOXZSEIBKUGN-UHFFFAOYSA-N 0.000 claims description 3
- HRSFZELFLSEJIW-UHFFFAOYSA-N 2-[7-(1-benzofuran-5-yl)-2-tert-butyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound C1=C2OC=CC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(O)=O)CCC)C(C)(C)C)=C1 HRSFZELFLSEJIW-UHFFFAOYSA-N 0.000 claims description 3
- KHSNRCXEWDCAGD-UHFFFAOYSA-N 2-[7-(1-benzothiophen-5-yl)-2-tert-butyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound C1=C2SC=CC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(O)=O)CCC)C(C)(C)C)=C1 KHSNRCXEWDCAGD-UHFFFAOYSA-N 0.000 claims description 3
- OUALAWJLSPGUJH-DUSLRRAJSA-N 2-[7-[(3r)-3-[(4-chlorophenyl)sulfonylamino]piperidin-1-yl]-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound N([C@@H]1CCCN(C1)C=1N2N=CC=C2N=C(C)C=1C(C(O)=O)CCC)S(=O)(=O)C1=CC=C(Cl)C=C1 OUALAWJLSPGUJH-DUSLRRAJSA-N 0.000 claims description 3
- MNWMIIKHZZIKGE-PYUWXLGESA-N 2-[7-[(3r)-3-[(4-chlorophenyl)sulfonylamino]pyrrolidin-1-yl]-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound N([C@@H]1CCN(C1)C=1N2N=CC=C2N=C(C)C=1C(C(O)=O)CCC)S(=O)(=O)C1=CC=C(Cl)C=C1 MNWMIIKHZZIKGE-PYUWXLGESA-N 0.000 claims description 3
- OUALAWJLSPGUJH-KKFHFHRHSA-N 2-[7-[(3s)-3-[(4-chlorophenyl)sulfonylamino]piperidin-1-yl]-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound N([C@H]1CCCN(C1)C=1N2N=CC=C2N=C(C)C=1C(C(O)=O)CCC)S(=O)(=O)C1=CC=C(Cl)C=C1 OUALAWJLSPGUJH-KKFHFHRHSA-N 0.000 claims description 3
- MNWMIIKHZZIKGE-ATNAJCNCSA-N 2-[7-[(3s)-3-[(4-chlorophenyl)sulfonylamino]pyrrolidin-1-yl]-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound N([C@H]1CCN(C1)C=1N2N=CC=C2N=C(C)C=1C(C(O)=O)CCC)S(=O)(=O)C1=CC=C(Cl)C=C1 MNWMIIKHZZIKGE-ATNAJCNCSA-N 0.000 claims description 3
- 125000005670 ethenylalkyl group Chemical group 0.000 claims description 3
- ROSSKBXAXYEMJD-UHFFFAOYSA-N ethyl 2-[1,2,5-trimethyl-7-(4-methylphenyl)imidazo[4,5-b]pyridin-6-yl]pentanoate Chemical compound CCOC(=O)C(CCC)C1=C(C)N=C2N=C(C)N(C)C2=C1C1=CC=C(C)C=C1 ROSSKBXAXYEMJD-UHFFFAOYSA-N 0.000 claims description 3
- RRWWKHFBSMLBIR-UHFFFAOYSA-N ethyl 2-[2-benzyl-5-methyl-7-(4-methylphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound N=1N2C(C=3C=CC(C)=CC=3)=C(C(C(=O)OCC)CCC)C(C)=NC2=NC=1CC1=CC=CC=C1 RRWWKHFBSMLBIR-UHFFFAOYSA-N 0.000 claims description 3
- GSMINQVJVGPMSC-UHFFFAOYSA-N ethyl 2-[5-methyl-7-(4-methylphenyl)-3-phenylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCOC(=O)C(CCC)C=1C(C)=NC2=C(C=3C=CC=CC=3)C=NN2C=1C1=CC=C(C)C=C1 GSMINQVJVGPMSC-UHFFFAOYSA-N 0.000 claims description 3
- JKFXVQFXQKDNKW-YMBRHYMPSA-N ethyl 2-[7-[(3r)-3-[(4-chlorophenyl)sulfonylamino]piperidin-1-yl]-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound N([C@@H]1CCCN(C1)C=1N2N=CC=C2N=C(C)C=1C(C(=O)OCC)CCC)S(=O)(=O)C1=CC=C(Cl)C=C1 JKFXVQFXQKDNKW-YMBRHYMPSA-N 0.000 claims description 3
- DDKFVKDOIDHQCA-QSVWIEALSA-N ethyl 2-[7-[(3r)-3-[(4-chlorophenyl)sulfonylamino]pyrrolidin-1-yl]-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound N([C@@H]1CCN(C1)C=1N2N=CC=C2N=C(C)C=1C(C(=O)OCC)CCC)S(=O)(=O)C1=CC=C(Cl)C=C1 DDKFVKDOIDHQCA-QSVWIEALSA-N 0.000 claims description 3
- ORQSSINLIKGDDH-UHFFFAOYSA-N methyl 2-(2-tert-butyl-5-methyl-7-naphthalen-2-ylpyrazolo[1,5-a]pyrimidin-6-yl)pentanoate Chemical compound C1=CC=CC2=CC(C=3N4N=C(C=C4N=C(C)C=3C(C(=O)OC)CCC)C(C)(C)C)=CC=C21 ORQSSINLIKGDDH-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- NIAGRZXECTZHFH-UHFFFAOYSA-N methyl 2-[2-tert-butyl-3-chloro-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=C(Cl)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 NIAGRZXECTZHFH-UHFFFAOYSA-N 0.000 claims description 3
- GBCHFNJXUAJZNA-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(1-methyl-2,3-dihydroindol-5-yl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound C1=C2N(C)CCC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(=O)OC)CCC)C(C)(C)C)=C1 GBCHFNJXUAJZNA-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 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 claims description 3
- RGNDRPXXEXTNOV-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)-3-phenylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=C(C=3C=CC=CC=3)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 RGNDRPXXEXTNOV-UHFFFAOYSA-N 0.000 claims description 3
- BUCSYAOPYLKVNH-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]-3-phenylpropanoate Chemical compound CC1=NC2=CC(C(C)(C)C)=NN2C(C=2C=CC(C)=CC=2)=C1C(C(=O)OC)CC1=CC=CC=C1 BUCSYAOPYLKVNH-UHFFFAOYSA-N 0.000 claims description 3
- KBFXQHJIUMUAKI-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]-6,6,6-trifluorohexanoate Chemical compound FC(F)(F)CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 KBFXQHJIUMUAKI-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- BFWQWDKJFRWADW-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(4-chloro-2-fluorophenyl)-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=C1F BFWQWDKJFRWADW-UHFFFAOYSA-N 0.000 claims description 3
- DMGWILUXVZJQQB-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(4-chlorophenyl)-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=C1 DMGWILUXVZJQQB-UHFFFAOYSA-N 0.000 claims description 3
- IUFRCEJOVVRYJS-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(4-ethylphenyl)-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(CC)C=C1 IUFRCEJOVVRYJS-UHFFFAOYSA-N 0.000 claims description 3
- WKDGJEIHWIZVNS-UHFFFAOYSA-N methyl 2-[7-(2-amino-4-methylphenyl)-2-tert-butyl-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=C1N WKDGJEIHWIZVNS-UHFFFAOYSA-N 0.000 claims description 3
- GZGMTIWBAHLYEK-UHFFFAOYSA-N 2-(2-tert-butyl-5-methyl-7-naphthalen-2-ylpyrazolo[1,5-a]pyrimidin-6-yl)pentanoic acid Chemical compound C1=CC=CC2=CC(C=3N4N=C(C=C4N=C(C)C=3C(C(O)=O)CCC)C(C)(C)C)=CC=C21 GZGMTIWBAHLYEK-UHFFFAOYSA-N 0.000 claims description 2
- GNXSAWJSKOMJBK-UHFFFAOYSA-N 2-(5-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-6-yl)pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC=NN2C=1C1=CC=CC=C1 GNXSAWJSKOMJBK-UHFFFAOYSA-N 0.000 claims description 2
- CVQAGXTYVWENLW-UHFFFAOYSA-N 2-[1,2,5-trimethyl-7-(4-methylphenyl)imidazo[4,5-b]pyridin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C1=C(C)N=C2N=C(C)N(C)C2=C1C1=CC=C(C)C=C1 CVQAGXTYVWENLW-UHFFFAOYSA-N 0.000 claims description 2
- DGOYWGFASFNQCE-UHFFFAOYSA-N 2-[2,3,5-trimethyl-7-(4-methylphenyl)imidazo[4,5-b]pyridin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C1=C(C)N=C2N(C)C(C)=NC2=C1C1=CC=C(C)C=C1 DGOYWGFASFNQCE-UHFFFAOYSA-N 0.000 claims description 2
- DDQUPFIECLJEGV-UHFFFAOYSA-N 2-[2-(furan-2-yl)-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C=3OC=CC=3)=NN2C=1C1=CC=C(C)C=C1 DDQUPFIECLJEGV-UHFFFAOYSA-N 0.000 claims description 2
- BBUITDOXUGTBNG-UHFFFAOYSA-N 2-[2-tert-butyl-3,5-dimethyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=C(C)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 BBUITDOXUGTBNG-UHFFFAOYSA-N 0.000 claims description 2
- RJEXULGSJPXLCR-UHFFFAOYSA-N 2-[2-tert-butyl-5-methyl-3,7-bis(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=C(C=3C=CC(C)=CC=3)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 RJEXULGSJPXLCR-UHFFFAOYSA-N 0.000 claims description 2
- KQCXTKPWKZAPHA-UHFFFAOYSA-N 2-[2-tert-butyl-5-methyl-7-(1-methyl-2,3-dihydroindol-5-yl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound C1=C2N(C)CCC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(O)=O)CCC)C(C)(C)C)=C1 KQCXTKPWKZAPHA-UHFFFAOYSA-N 0.000 claims description 2
- UGLMKGZIFJLZHE-UHFFFAOYSA-N 2-[2-tert-butyl-5-methyl-7-(1-methylindol-6-yl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound C1=C2C=CN(C)C2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(O)=O)CCC)C(C)(C)C)=C1 UGLMKGZIFJLZHE-UHFFFAOYSA-N 0.000 claims description 2
- LEUWCFUYOQXKOX-UHFFFAOYSA-N 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]-3-phenylpropanoic acid Chemical compound C1=CC(C)=CC=C1C(N1N=C(C=C1N=C1C)C(C)(C)C)=C1C(C(O)=O)CC1=CC=CC=C1 LEUWCFUYOQXKOX-UHFFFAOYSA-N 0.000 claims description 2
- QRHYISMQDPEYTF-UHFFFAOYSA-N 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]-4-methoxybutanoic acid Chemical compound COCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 QRHYISMQDPEYTF-UHFFFAOYSA-N 0.000 claims description 2
- WZKBMMYBXFIGIK-UHFFFAOYSA-N 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]-6,6,6-trifluorohexanoic acid Chemical compound C1=CC(C)=CC=C1C1=C(C(CCCC(F)(F)F)C(O)=O)C(C)=NC2=CC(C(C)(C)C)=NN12 WZKBMMYBXFIGIK-UHFFFAOYSA-N 0.000 claims description 2
- CBWBALVLITWLLN-UHFFFAOYSA-N 2-[2-tert-butyl-5-methyl-7-(4-propan-2-ylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C(C)C)C=C1 CBWBALVLITWLLN-UHFFFAOYSA-N 0.000 claims description 2
- GRYWSSFOZQTQEV-UHFFFAOYSA-N 2-[2-tert-butyl-5-methyl-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C(F)(F)F)C=C1 GRYWSSFOZQTQEV-UHFFFAOYSA-N 0.000 claims description 2
- MNESLVHOFYBTAA-UHFFFAOYSA-N 2-[2-tert-butyl-7-(1,2-dihydroacenaphthylen-5-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]acetic acid Chemical compound C1CC2=CC=CC3=C2C1=CC=C3C1=C(CC(O)=O)C(C)=NC2=CC(C(C)(C)C)=NN21 MNESLVHOFYBTAA-UHFFFAOYSA-N 0.000 claims description 2
- BYKOPFAEMORCED-UHFFFAOYSA-N 2-[2-tert-butyl-7-(1h-indol-5-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound C1=C2NC=CC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(O)=O)CCC)C(C)(C)C)=C1 BYKOPFAEMORCED-UHFFFAOYSA-N 0.000 claims description 2
- KAMYNKLLXNAGMG-UHFFFAOYSA-N 2-[2-tert-butyl-7-(1h-indol-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound C1=C2C=CNC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(O)=O)CCC)C(C)(C)C)=C1 KAMYNKLLXNAGMG-UHFFFAOYSA-N 0.000 claims description 2
- ZGLLCPSIATYDLQ-UHFFFAOYSA-N 2-[2-tert-butyl-7-(2,4-dimethylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1C ZGLLCPSIATYDLQ-UHFFFAOYSA-N 0.000 claims description 2
- GYVBXKLIUGICQL-UHFFFAOYSA-N 2-[2-tert-butyl-7-(2-fluoro-4-methoxyphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(OC)C=C1F GYVBXKLIUGICQL-UHFFFAOYSA-N 0.000 claims description 2
- AFAPKMJQVOGGRJ-UHFFFAOYSA-N 2-[2-tert-butyl-7-(2-hydroxy-4-methylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]acetic acid Chemical compound OC1=CC(C)=CC=C1C1=C(CC(O)=O)C(C)=NC2=CC(C(C)(C)C)=NN12 AFAPKMJQVOGGRJ-UHFFFAOYSA-N 0.000 claims description 2
- KPJDWJHAWQHSPJ-UHFFFAOYSA-N 2-[2-tert-butyl-7-(2-methoxy-4-methylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]acetic acid Chemical compound COC1=CC(C)=CC=C1C1=C(CC(O)=O)C(C)=NC2=CC(C(C)(C)C)=NN12 KPJDWJHAWQHSPJ-UHFFFAOYSA-N 0.000 claims description 2
- MKGWPXXQHZUFMS-UHFFFAOYSA-N 2-[2-tert-butyl-7-(3,4-dimethylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C(C)=C1 MKGWPXXQHZUFMS-UHFFFAOYSA-N 0.000 claims description 2
- LWILTRDMBGHKHS-UHFFFAOYSA-N 2-[2-tert-butyl-7-(4-chloro-2-fluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(Cl)C=C1F LWILTRDMBGHKHS-UHFFFAOYSA-N 0.000 claims description 2
- GRXLHNONMPEULL-UHFFFAOYSA-N 2-[2-tert-butyl-7-(4-chloro-2-methoxyphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(Cl)C=C1OC GRXLHNONMPEULL-UHFFFAOYSA-N 0.000 claims description 2
- DRQHXCKQRKDUBW-UHFFFAOYSA-N 2-[2-tert-butyl-7-(4-ethylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(CC)C=C1 DRQHXCKQRKDUBW-UHFFFAOYSA-N 0.000 claims description 2
- OCTWBBSWKFAZHN-UHFFFAOYSA-N 2-[3,5-dimethyl-7-(4-methylphenyl)-2-propylimidazo[4,5-b]pyridin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C1=C(C)N=C2N(C)C(CCC)=NC2=C1C1=CC=C(C)C=C1 OCTWBBSWKFAZHN-UHFFFAOYSA-N 0.000 claims description 2
- HQSJKODIBGNPGK-UHFFFAOYSA-N 2-[3-bromo-2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=C(Br)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 HQSJKODIBGNPGK-UHFFFAOYSA-N 0.000 claims description 2
- YQVIZNUKANANHG-UHFFFAOYSA-N 2-[5-methyl-3,7-bis(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=C(C=3C=CC(C)=CC=3)C=NN2C=1C1=CC=C(C)C=C1 YQVIZNUKANANHG-UHFFFAOYSA-N 0.000 claims description 2
- SCWQCJBHQCOGKH-UHFFFAOYSA-N 2-[5-methyl-7-(4-methylphenyl)-2-propan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]acetic acid Chemical compound N12N=C(C(C)C)N=C2N=C(C)C(CC(O)=O)=C1C1=CC=C(C)C=C1 SCWQCJBHQCOGKH-UHFFFAOYSA-N 0.000 claims description 2
- FIDWHXVEMALQMH-UHFFFAOYSA-N 2-[5-methyl-7-(4-methylphenyl)-2-propan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=NC(C(C)C)=NN2C=1C1=CC=C(C)C=C1 FIDWHXVEMALQMH-UHFFFAOYSA-N 0.000 claims description 2
- SAKPQHRGZSXUFU-UHFFFAOYSA-N 2-[5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC=NN2C=1C1=CC=C(C)C=C1 SAKPQHRGZSXUFU-UHFFFAOYSA-N 0.000 claims description 2
- RZNJTXWJNDWJFA-UHFFFAOYSA-N ethyl 2-[3,5-dimethyl-7-(4-methylphenyl)-2-propan-2-ylimidazo[4,5-b]pyridin-6-yl]pentanoate Chemical compound CCOC(=O)C(CCC)C1=C(C)N=C2N(C)C(C(C)C)=NC2=C1C1=CC=C(C)C=C1 RZNJTXWJNDWJFA-UHFFFAOYSA-N 0.000 claims description 2
- GGXVMLLGEZGECP-UHFFFAOYSA-N ethyl 2-[3,5-dimethyl-7-(4-methylphenyl)-2-propylimidazo[4,5-b]pyridin-6-yl]pentanoate Chemical compound CCOC(=O)C(CCC)C1=C(C)N=C2N(C)C(CCC)=NC2=C1C1=CC=C(C)C=C1 GGXVMLLGEZGECP-UHFFFAOYSA-N 0.000 claims description 2
- DDKFVKDOIDHQCA-LROBGIAVSA-N ethyl 2-[7-[(3s)-3-[(4-chlorophenyl)sulfonylamino]pyrrolidin-1-yl]-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound N([C@H]1CCN(C1)C=1N2N=CC=C2N=C(C)C=1C(C(=O)OCC)CCC)S(=O)(=O)C1=CC=C(Cl)C=C1 DDKFVKDOIDHQCA-LROBGIAVSA-N 0.000 claims 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 claims description 2
- FLUPVKLGCFLIJF-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(1,2-dihydroacenaphthylen-5-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]acetate Chemical compound C1CC2=CC=CC3=C2C1=CC=C3C1=C(CC(=O)OC)C(C)=NC2=CC(C(C)(C)C)=NN21 FLUPVKLGCFLIJF-UHFFFAOYSA-N 0.000 claims description 2
- WKLYXSMVNMHALN-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(3-hydroxyphenyl)-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=CC(O)=C1 WKLYXSMVNMHALN-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 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 claims description 2
- JIDYEBBOEJPLSX-UHFFFAOYSA-N methyl 2-[5-methyl-7-(4-methylphenyl)-2-propan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]acetate Chemical compound COC(=O)CC=1C(C)=NC2=NC(C(C)C)=NN2C=1C1=CC=C(C)C=C1 JIDYEBBOEJPLSX-UHFFFAOYSA-N 0.000 claims description 2
- SHRCFAYLXVCZGN-UHFFFAOYSA-N methyl 2-[5-methyl-7-(4-methylphenyl)-2-propan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=NC(C(C)C)=NN2C=1C1=CC=C(C)C=C1 SHRCFAYLXVCZGN-UHFFFAOYSA-N 0.000 claims description 2
- PUVBNHRJMRJVIF-UHFFFAOYSA-N methyl 2-[5-methyl-7-(4-methylphenyl)-2-propylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(CCC)=NN2C=1C1=CC=C(C)C=C1 PUVBNHRJMRJVIF-UHFFFAOYSA-N 0.000 claims description 2
- YQPKJLAEVDDFMC-UHFFFAOYSA-N 2-[2-tert-butyl-3-chloro-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=C(Cl)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 YQPKJLAEVDDFMC-UHFFFAOYSA-N 0.000 claims 1
- LJSRZBPBUXOLLV-UHFFFAOYSA-N 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)-3-phenylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=C(C=3C=CC=CC=3)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 LJSRZBPBUXOLLV-UHFFFAOYSA-N 0.000 claims 1
- MITIIKZWPJLHBT-UHFFFAOYSA-N 2-[2-tert-butyl-7-(2,4-difluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(F)C=C1F MITIIKZWPJLHBT-UHFFFAOYSA-N 0.000 claims 1
- YVWIITGMXHCAGH-UHFFFAOYSA-N 2-[2-tert-butyl-7-(2-chloro-4-methylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1Cl YVWIITGMXHCAGH-UHFFFAOYSA-N 0.000 claims 1
- AAERGJZADAXRHW-UHFFFAOYSA-N 2-[2-tert-butyl-7-(2-fluoro-4-methylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound CCCC(C(O)=O)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1F AAERGJZADAXRHW-UHFFFAOYSA-N 0.000 claims 1
- SDYQFWGBOZUKDT-UHFFFAOYSA-N 2-[2-tert-butyl-7-(3,4-dihydro-2h-chromen-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoic acid Chemical compound O1CCCC2=CC(C=3N4N=C(C=C4N=C(C)C=3C(C(O)=O)CCC)C(C)(C)C)=CC=C21 SDYQFWGBOZUKDT-UHFFFAOYSA-N 0.000 claims 1
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- WUOQXNWMYLFAHT-MRVPVSSYSA-N tert-butyl n-[(3r)-piperidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1CCCNC1 WUOQXNWMYLFAHT-MRVPVSSYSA-N 0.000 description 1
- DQQJBEAXSOOCPG-SSDOTTSWSA-N tert-butyl n-[(3r)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1CCNC1 DQQJBEAXSOOCPG-SSDOTTSWSA-N 0.000 description 1
- WUOQXNWMYLFAHT-QMMMGPOBSA-N tert-butyl n-[(3s)-piperidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCCNC1 WUOQXNWMYLFAHT-QMMMGPOBSA-N 0.000 description 1
- DQQJBEAXSOOCPG-ZETCQYMHSA-N tert-butyl n-[(3s)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCNC1 DQQJBEAXSOOCPG-ZETCQYMHSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
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- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
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- ZFEAMMNVDPDEGE-LGRGJMMZSA-N tifuvirtide Chemical compound C([C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(C)=O)[C@@H](C)CC)[C@@H](C)O)[C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)C1=CC=C(O)C=C1 ZFEAMMNVDPDEGE-LGRGJMMZSA-N 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 229960000838 tipranavir Drugs 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
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- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000440 toxicity profile Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- 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
- 229960001099 trimetrexate Drugs 0.000 description 1
- DFHAXXVZCFXGOQ-UHFFFAOYSA-K trisodium phosphonoformate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)P([O-])([O-])=O DFHAXXVZCFXGOQ-UHFFFAOYSA-K 0.000 description 1
- YFNGWGVTFYSJHE-UHFFFAOYSA-K trisodium;phosphonoformate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O YFNGWGVTFYSJHE-UHFFFAOYSA-K 0.000 description 1
- 229940111527 trizivir Drugs 0.000 description 1
- WVPSKSLAZQPAKQ-CDMJZVDBSA-N trovafloxacin Chemical compound C([C@H]1[C@@H]([C@H]1C1)N)N1C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=NC=1N2C1=CC=C(F)C=C1F WVPSKSLAZQPAKQ-CDMJZVDBSA-N 0.000 description 1
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- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
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Classifications
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0922520A GB0922520D0 (en) | 2009-12-23 | 2009-12-23 | Novel antiviral compounds |
| GB0922520.2 | 2009-12-23 | ||
| GB1001204.5 | 2010-01-26 | ||
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2781780A1 CA2781780A1 (en) | 2011-06-30 |
| CA2781780C true CA2781780C (en) | 2015-02-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2781780A Expired - Fee Related CA2781780C (en) | 2009-12-23 | 2010-12-20 | Novel antiviral compounds |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20120316161A1 (OSRAM) |
| EP (1) | EP2516008B1 (OSRAM) |
| JP (1) | JP2013515692A (OSRAM) |
| KR (1) | KR101483834B1 (OSRAM) |
| CN (1) | CN102770181B (OSRAM) |
| AU (1) | AU2010334958B2 (OSRAM) |
| CA (1) | CA2781780C (OSRAM) |
| ES (1) | ES2475970T3 (OSRAM) |
| IL (1) | IL219965A0 (OSRAM) |
| MX (1) | MX2012007410A (OSRAM) |
| PT (1) | PT2516008E (OSRAM) |
| SG (2) | SG10201408512RA (OSRAM) |
| WO (1) | WO2011076765A1 (OSRAM) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0908394D0 (en) | 2009-05-15 | 2009-06-24 | Univ Leuven Kath | Novel viral replication inhibitors |
| GB0913636D0 (en) | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| NZ604716A (en) | 2010-07-02 | 2014-12-24 | Gilead Sciences Inc | 2-quinolinyl-acetic acid derivatives as hiv antiviral compounds |
| PH12013500011A1 (en) | 2010-07-02 | 2013-02-18 | Gilead Sciences Inc | Napht-2-ylacetic acid derivatives to treat aids |
| US8633200B2 (en) | 2010-09-08 | 2014-01-21 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| EP2640705A2 (en) | 2010-11-15 | 2013-09-25 | Katholieke Universiteit Leuven | Novel antiviral compounds |
| CN105330675A (zh) | 2010-11-15 | 2016-02-17 | Viiv保健英国有限公司 | Hiv复制的抑制剂 |
| EP2511273B8 (en) | 2011-04-15 | 2019-06-26 | Hivih | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
| JP5918848B2 (ja) | 2011-04-21 | 2016-05-18 | ギリアード サイエンシーズ， インコーポレイテッド | ベンゾチアゾール化合物およびその薬学的使用 |
| US8791108B2 (en) | 2011-08-18 | 2014-07-29 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| US9199959B2 (en) | 2011-10-25 | 2015-12-01 | Shionogi & Co., Ltd. | HIV replication inhibitor |
| AU2012358805B2 (en) * | 2011-12-22 | 2017-07-20 | 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 |
| US9006235B2 (en) | 2012-03-06 | 2015-04-14 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| US8987250B2 (en) | 2012-04-20 | 2015-03-24 | Gilead Sciences, Inc. | Therapeutic compounds |
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| WO1992018504A1 (en) * | 1991-04-22 | 1992-10-29 | Otsuka Pharmaceutical Factory, Inc. | PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVE AND ANTI-INFLAMMATORY CONTAINING THE SAME |
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- 2010-12-20 US US13/518,434 patent/US20120316161A1/en not_active Abandoned
- 2010-12-20 WO PCT/EP2010/070306 patent/WO2011076765A1/en not_active Ceased
- 2010-12-20 EP EP10801407.7A patent/EP2516008B1/en not_active Not-in-force
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| CN102770181B (zh) | 2015-08-12 |
| CA2781780A1 (en) | 2011-06-30 |
| WO2011076765A1 (en) | 2011-06-30 |
| EP2516008A1 (en) | 2012-10-31 |
| CN102770181A (zh) | 2012-11-07 |
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| MX2012007410A (es) | 2012-07-17 |
| JP2013515692A (ja) | 2013-05-09 |
| KR20120106869A (ko) | 2012-09-26 |
| PT2516008E (pt) | 2014-07-16 |
| ES2475970T3 (es) | 2014-07-11 |
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| AU2010334958A1 (en) | 2012-06-07 |
| SG181423A1 (en) | 2012-07-30 |
| SG10201408512RA (en) | 2015-02-27 |
| AU2010334958B2 (en) | 2015-02-05 |
| KR101483834B1 (ko) | 2015-01-16 |
| EP2516008B1 (en) | 2014-04-16 |
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