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
- 230000002265 prevention Effects 0.000 claims 2
- 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
- 239000000543 intermediate Substances 0.000 description 1
- 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
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
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| GB0913636D0 (en) | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| MA34397B1 (fr) | 2010-07-02 | 2013-07-03 | Gilead Sciences Inc | Dérivés d'acide napht-2-ylacétique dans le traitement du sida |
| NZ604716A (en) | 2010-07-02 | 2014-12-24 | 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 |
| MX2013005478A (es) | 2010-11-15 | 2013-08-29 | Univ Leuven Kath | Compuestos heterociclicos condensados antivirales. |
| AU2011330850B2 (en) | 2010-11-15 | 2016-01-28 | Viiv Healthcare Uk Limited | Inhibitors of HIV replication |
| ES2742261T3 (es) | 2011-04-15 | 2020-02-13 | Hivih | Inhibidores de la replicación viral, su proceso de preparación y sus usos terapéuticos |
| AP2013007249A0 (en) | 2011-04-21 | 2013-11-30 | Gilead Sciences Inc | Benzothiazole compounds and their pharmaceutical use |
| US8791108B2 (en) | 2011-08-18 | 2014-07-29 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| JP6099149B2 (ja) | 2011-10-25 | 2017-03-22 | 塩野義製薬株式会社 | Ｈｉｖ複製阻害剤 |
| CA2858096C (en) * | 2011-12-22 | 2020-06-23 | Gilead Sciences, Inc. | Pyrazolo[1,5-a]pyrimidines as antiviral agents |
| WO2013103738A1 (en) | 2012-01-04 | 2013-07-11 | Gilead Sciences, Inc. | Napthalene acetic acid derivatives against hiv infection |
| WO2013103724A1 (en) | 2012-01-04 | 2013-07-11 | 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 |
| SG11201401189WA (en) | 2012-04-20 | 2014-09-26 | 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 |
| US9655889B2 (en) | 2013-03-13 | 2017-05-23 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| WO2014164428A1 (en) | 2013-03-13 | 2014-10-09 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| US9580431B2 (en) * | 2013-03-13 | 2017-02-28 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| EP2970297A1 (en) | 2013-03-14 | 2016-01-20 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| EP2970274B1 (en) | 2013-03-14 | 2017-03-01 | VIIV Healthcare UK (No.5) Limited | 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 |
| WO2015123230A1 (en) | 2014-02-12 | 2015-08-20 | Bristol-Myers Squibb Company | Benzothiazole macrocycles as inhibitors of human immunodeficiency virus replication |
| WO2015123182A1 (en) * | 2014-02-12 | 2015-08-20 | Bristol-Myers Squibb Company | 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 |
| EP3152215A1 (en) | 2014-02-18 | 2017-04-12 | ViiV Healthcare UK (No.5) Limited | Pyrazolopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
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| US9273067B2 (en) | 2014-02-19 | 2016-03-01 | Bristol-Myers Squibb Company | Pyrazolopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
| WO2015126765A1 (en) | 2014-02-19 | 2015-08-27 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| US9637501B2 (en) | 2014-02-20 | 2017-05-02 | Viiv Healthcare Uk (No. 5) Limited | 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 |
| JP6579549B2 (ja) | 2014-05-16 | 2019-09-25 | 塩野義製薬株式会社 | Ｈｉｖ複製阻害作用を有する３環性複素環誘導体 |
| KR101692478B1 (ko) | 2014-07-10 | 2017-01-05 | 계명대학교 산학협력단 | Ｓｙ０２９를 유효성분으로 함유하는 항바이러스 조성물 |
| WO2016194806A1 (ja) | 2015-05-29 | 2016-12-08 | 塩野義製薬株式会社 | Ｈｉｖ複製阻害作用を有する含窒素３環性誘導体 |
| WO2017006261A1 (en) | 2015-07-06 | 2017-01-12 | VIIV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| KR20180025926A (ko) | 2015-07-08 | 2018-03-09 | 비브 헬스케어 유케이 (넘버5) 리미티드 | 인간 면역결핍 바이러스 복제의 억제제로서의 피리딘-3-일 아세트산 유도체 |
| BR112018000253A2 (pt) | 2015-07-09 | 2018-09-04 | Viiv Healthcare Uk No 5 Ltd | composto, composição, e, método para tratar a infecção pelo hiv. |
| EP3319954A1 (en) | 2015-07-09 | 2018-05-16 | VIIV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| AU2016306065A1 (en) | 2015-08-07 | 2018-03-01 | VIIV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| JP2018522924A (ja) | 2015-08-10 | 2018-08-16 | 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イミダゾピリジン大環状化合物 |
| 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 |
| AU2016305339A1 (en) | 2015-08-12 | 2018-03-01 | VIIV Healthcare UK (No.5) Limited | 5-(n-fused tricyclic Aryl tetrahydroisoquinolin-6-yl) pyridin-3- yl acetic acid derivatives as inhibitors of Human Immunodeficiency Virus replication |
| 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 |
| RU2018107928A (ru) | 2015-08-20 | 2019-09-20 | ВАЙВ ХЕЛТКЕР ЮКей (N5) ЛИМИТЕД | Производные пиридин-3-ил уксусной кислоты в качестве ингибиторов репликации вируса иммунодефицита человека |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
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| CA2107479C (en) * | 1991-04-22 | 1997-12-16 | Makoto Inoue | Pyrazolo[1,5-a]pyrimidine derivatives and anti-inflammatory agent containing the same |
| 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 |
| CA2463975A1 (en) | 2001-10-26 | 2003-05-01 | Maria Emilia Di Francesco | Dihydroxypyrimidine carboxamide inhibitors of hiv integrase |
| AU2002349675A1 (en) | 2001-12-05 | 2003-06-17 | Shionogi And Co., Ltd. | Derivative having hiv integrase inhibitory activity |
| WO2003049690A2 (en) | 2001-12-12 | 2003-06-19 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| PL216539B1 (pl) | 2001-12-21 | 2014-04-30 | Tibotec Pharm Ltd | Związki fenylosulfonylowe i zastosowanie związków fenylosulfonylowych |
| AU2003216049B2 (en) | 2002-01-17 | 2008-07-17 | Merck Sharp & Dohme Corp. | 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 |
| CA2705338A1 (en) * | 2007-11-16 | 2009-05-22 | Boehringer Ingelheim International Gmbh | Inhibitors of human immunodeficiency virus replication |
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- 2010-12-20 AU AU2010334958A patent/AU2010334958B2/en not_active Ceased
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- 2010-12-20 KR KR1020127019420A patent/KR101483834B1/ko not_active Expired - Fee Related
- 2010-12-20 PT PT108014077T patent/PT2516008E/pt unknown
- 2010-12-20 ES ES10801407.7T patent/ES2475970T3/es active Active
- 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 MX MX2012007410A patent/MX2012007410A/es active IP Right Grant
- 2010-12-20 EP EP10801407.7A patent/EP2516008B1/en not_active Not-in-force
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2012
- 2012-05-23 IL IL219965A patent/IL219965A0/en unknown
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