JP2013515692A5 - - Google Patents
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- JP2013515692A5 JP2013515692A5 JP2012545282A JP2012545282A JP2013515692A5 JP 2013515692 A5 JP2013515692 A5 JP 2013515692A5 JP 2012545282 A JP2012545282 A JP 2012545282A JP 2012545282 A JP2012545282 A JP 2012545282A JP 2013515692 A5 JP2013515692 A5 JP 2013515692A5
- Authority
- JP
- Japan
- Prior art keywords
- heterocycle
- pyrimidin
- methyl
- tert
- butyl
- 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.)
- Ceased
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- 125000003342 alkenyl group Chemical group 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- 125000000304 alkynyl group Chemical group 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 58
- 125000000623 heterocyclic group Chemical group 0.000 claims description 51
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 39
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 39
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- -1 cycloalkynyl Chemical group 0.000 claims description 18
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 208000036142 Viral infection Diseases 0.000 claims description 9
- 230000009385 viral infection Effects 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000005670 ethenylalkyl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 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
- 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 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
- 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 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
- 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 2
- 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 description 2
- 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 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
- 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 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
- 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 2
- 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 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
- 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 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
- 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 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
- 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 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
- 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 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
- 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 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
- 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 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
- 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 2
- 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 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
- 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 2
- 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 2
- SRXJZSZPHYRIDG-UHFFFAOYSA-N 2-[7-(2-amino-4-methylphenyl)-2-tert-butyl-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=C1N SRXJZSZPHYRIDG-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000000840 anti-viral effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 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 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
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- JKFXVQFXQKDNKW-ZQRQZVKFSA-N ethyl 2-[7-[(3s)-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-ZQRQZVKFSA-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
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 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 2
- 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 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 claims 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 claims 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 claims 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 claims 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 claims description 2
- 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 2
- 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 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 claims 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 claims description 2
- 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 2
- POANUONYZSKWGW-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]-3-methylpentanoate Chemical compound CCC(C)C(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 POANUONYZSKWGW-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 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 2
- 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 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 claims 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 claims 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 claims description 2
- 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 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims description 2
- JXATZROYLCCLHT-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2-methoxy-4-methylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]acetate Chemical compound COC(=O)CC=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1OC JXATZROYLCCLHT-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- JXEBNOLMYWUEIZ-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(3,4-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(C)=C1 JXEBNOLMYWUEIZ-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
- 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 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
- 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 2
- 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 2
- 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 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
- 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 2
- AMRVSNYZRMIGGJ-UHFFFAOYSA-N methyl 2-[7-(1-benzofuran-5-yl)-2-tert-butyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound C1=C2OC=CC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(=O)OC)CCC)C(C)(C)C)=C1 AMRVSNYZRMIGGJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
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- ASSTWJJRTFYMHG-UHFFFAOYSA-N C(C1=CC=CC=C1)C1=NN2C(N=C(C(=C2C2=CC=C(C=C2)C)C(C(=O)O)CCC)C)=N1 Chemical compound C(C1=CC=CC=C1)C1=NN2C(N=C(C(=C2C2=CC=C(C=C2)C)C(C(=O)O)CCC)C)=N1 ASSTWJJRTFYMHG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 1,2-dimethoxyethane;hydrate Chemical compound O.COCCOC ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 0.000 description 1
- JQLYKUPEQYNDFF-UHFFFAOYSA-N 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole Chemical compound C=1C=C2N(C)C=CC2=CC=1B1OC(C)(C)C(C)(C)O1 JQLYKUPEQYNDFF-UHFFFAOYSA-N 0.000 description 1
- 0 CC(CCNC)C1*=C(C)C(C(*)(*)O)=C(*)*1*(*)C(*)*I Chemical compound CC(CCNC)C1*=C(C)C(C(*)(*)O)=C(*)*1*(*)C(*)*I 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
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- 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 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
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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 |
| US9102614B2 (en) | 2010-07-02 | 2015-08-11 | Gilead Sciences, Inc. | Naphth-2-ylacetic acid derivatives to treat AIDS |
| WO2012003498A1 (en) | 2010-07-02 | 2012-01-05 | Gilead Sciences, Inc. | 2 -quinolinyl- acetic acid derivatives as hiv antiviral compounds |
| US8633200B2 (en) | 2010-09-08 | 2014-01-21 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| EP2640729B1 (en) | 2010-11-15 | 2016-12-21 | VIIV Healthcare UK Limited | Inhibitors of hiv replication |
| NZ610315A (en) | 2010-11-15 | 2015-08-28 | Univ Leuven Kath | Antiviral condensed heterocyclic compounds |
| ES2742261T3 (es) | 2011-04-15 | 2020-02-13 | Hivih | Inhibidores de la replicación viral, su proceso de preparación y sus usos terapéuticos |
| PE20141066A1 (es) | 2011-04-21 | 2014-09-05 | Gilead Sciences Inc | Compuestos de benzotiazol |
| US8791108B2 (en) | 2011-08-18 | 2014-07-29 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| WO2013062028A1 (ja) | 2011-10-25 | 2013-05-02 | 塩野義製薬株式会社 | Ｈｉｖ複製阻害剤 |
| EP2794611B1 (en) * | 2011-12-22 | 2017-10-11 | Gilead Sciences, Inc. | Pyrazolo[1,5-a]pyrimidines as antiviral agents |
| 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 |
| WO2013103738A1 (en) | 2012-01-04 | 2013-07-11 | Gilead Sciences, Inc. | Napthalene acetic acid derivatives against hiv infection |
| 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 |
| PH12014500842A1 (en) | 2012-04-20 | 2014-06-09 | Gilead Sciences Inc | Benzothiazol-6-yl acetic acid derivatives and their use for treating an hiv infection |
| 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 |
| TW201441197A (zh) | 2013-01-31 | 2014-11-01 | Shionogi & Co | Ｈｉｖ複製抑制劑 |
| WO2014164467A1 (en) | 2013-03-13 | 2014-10-09 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| ES2623777T3 (es) | 2013-03-13 | 2017-07-12 | VIIV Healthcare UK (No.5) Limited | Inhibidores de la replicación del virus de la inmunodeficiencia humana |
| WO2014164428A1 (en) | 2013-03-13 | 2014-10-09 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| ES2623904T3 (es) | 2013-03-14 | 2017-07-12 | VIIV Healthcare UK (No.5) Limited | Inhibidores de la replicación del virus de la inmunodeficiencia humana |
| EP2970297A1 (en) | 2013-03-14 | 2016-01-20 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| 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 |
| WO2015123182A1 (en) * | 2014-02-12 | 2015-08-20 | Bristol-Myers Squibb Company | Pyrazolopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
| US9944656B2 (en) | 2014-02-12 | 2018-04-17 | VIIV Healthcare UK (No.5) Limited | Benzothiazole macrocycles as inhibitors of human immunodeficiency virus replication |
| US9409922B2 (en) | 2014-02-18 | 2016-08-09 | Bristol-Myers Squibb Company | Imidazopyridine macrocycles as inhibitors of human immunodeficiency virus replication |
| US9834566B2 (en) | 2014-02-18 | 2017-12-05 | VIIV Healthcare UK (No.5) Limited | Pyrazolopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
| EP3116879A1 (en) | 2014-02-18 | 2017-01-18 | VIIV Healthcare UK (No.5) Limited | Imidazopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
| ES2687322T3 (es) | 2014-02-19 | 2018-10-24 | VIIV Healthcare UK (No.5) Limited | Inhibidores de la replicación del virus de inmunodeficiencia humana |
| US9273067B2 (en) | 2014-02-19 | 2016-03-01 | Bristol-Myers Squibb Company | Pyrazolopyrimidine 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 |
| EP3116880B1 (en) | 2014-02-20 | 2018-03-21 | VIIV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid macrocycles as inhibitors of human immunodeficiency virus replication |
| US9975906B2 (en) | 2014-05-16 | 2018-05-22 | Shionogi & Co., Ltd. | Tricyclic heterocycle derivatives having HIV replication inhibitory effect |
| KR101692478B1 (ko) | 2014-07-10 | 2017-01-05 | 계명대학교 산학협력단 | Ｓｙ０２９를 유효성분으로 함유하는 항바이러스 조성물 |
| CA2987384A1 (en) | 2015-05-29 | 2016-12-08 | Shionogi & Co., Ltd. | Nitrogen-containing tricyclic derivative 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 |
| KR20180025926A (ko) | 2015-07-08 | 2018-03-09 | 비브 헬스케어 유케이 (넘버5) 리미티드 | 인간 면역결핍 바이러스 복제의 억제제로서의 피리딘-3-일 아세트산 유도체 |
| AU2016290205A1 (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 |
| 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 |
| CN108137532A (zh) | 2015-08-07 | 2018-06-08 | 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 |
| BR112018002681A2 (pt) | 2015-08-10 | 2019-04-24 | Viiv Healthcare Uk No 5 Ltd | ?composto, composição, e, método para tratamento de infecção por hiv? |
| TWI657086B (zh) | 2015-08-11 | 2019-04-21 | 英商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５－（ｎ－苯甲基四氫異喹啉－６－基）吡啶－３－基乙酸衍生物 |
| 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 |
| CN108137553A (zh) | 2015-08-12 | 2018-06-08 | 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5-(n-[6,5]-稠合双环芳基四氢异喹啉-6-基)吡啶-3-基乙酸衍生物 |
| CN108137552A (zh) | 2015-08-12 | 2018-06-08 | 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5-(n-稠合三环芳基四氢异喹啉-6-基)吡啶-3-基乙酸衍生物 |
| JP2018523695A (ja) | 2015-08-20 | 2018-08-23 | 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 |
| WO2017195112A1 (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 |
| 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 |
| WO2017195111A1 (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 |
| TW201835068A (zh) | 2017-01-03 | 2018-10-01 | 英商Viiv醫療保健英國(No.5)有限公司 | 作為人類免疫缺乏病毒複製之抑制劑之吡啶-3-基乙酸衍生物 |
| WO2018127801A1 (en) | 2017-01-03 | 2018-07-12 | 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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| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
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| 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 |
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| NZ533413A (en) | 2001-12-12 | 2006-09-29 | Bristol Myers Squibb Co | 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 |
| US7279487B2 (en) | 2002-01-17 | 2007-10-09 | Merck & Co., Inc. | Hydroxynaphthyridinone carboxamides useful as HIV integrase inhibitors |
| TW200306192A (en) | 2002-01-18 | 2003-11-16 | Bristol Myers Squibb Co | Tricyclic 2-pyrimidone compounds useful as HIV reverse transcriptase inhibitors |
| US7449488B2 (en) | 2002-06-04 | 2008-11-11 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
| PA8586801A1 (es) | 2002-10-31 | 2005-02-04 | Pfizer | Inhibidores de hiv-integrasa, composiciones farmaceuticas y metodos para su uso |
| US8461180B2 (en) * | 2007-11-16 | 2013-06-11 | Gilead Sciences, Inc. | Inhibitors of human immunodeficiency virus replication |
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2010
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- 2010-12-20 US US13/518,434 patent/US20120316161A1/en not_active Abandoned
- 2010-12-20 KR KR1020127019420A patent/KR101483834B1/ko not_active Expired - Fee Related
- 2010-12-20 SG SG2012035002A patent/SG181423A1/en unknown
- 2010-12-20 CN CN201080064636.2A patent/CN102770181B/zh not_active Expired - Fee Related
- 2010-12-20 PT PT108014077T patent/PT2516008E/pt unknown
- 2010-12-20 AU AU2010334958A patent/AU2010334958B2/en not_active Ceased
- 2010-12-20 JP JP2012545282A patent/JP2013515692A/ja not_active Ceased
- 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
- 2010-12-20 MX MX2012007410A patent/MX2012007410A/es active IP Right Grant
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2012
- 2012-05-23 IL IL219965A patent/IL219965A0/en unknown
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