JP2017503830A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017503830A5 JP2017503830A5 JP2016548033A JP2016548033A JP2017503830A5 JP 2017503830 A5 JP2017503830 A5 JP 2017503830A5 JP 2016548033 A JP2016548033 A JP 2016548033A JP 2016548033 A JP2016548033 A JP 2016548033A JP 2017503830 A5 JP2017503830 A5 JP 2017503830A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolo
- pyrimidin
- dimethyl
- amine
- methyl
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 13
- -1 methylenedioxy Chemical group 0.000 claims description 9
- 208000036142 Viral infection Diseases 0.000 claims description 8
- WPFZGADUIUVTCF-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=CC=NC2=CC=NN12 WPFZGADUIUVTCF-UHFFFAOYSA-N 0.000 claims description 8
- 230000009385 viral infection Effects 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- PLNYJRAFJKJYPQ-UHFFFAOYSA-N 1-[4-[[[3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]amino]methyl]phenyl]ethanone Chemical compound COC=1C=C(C=CC1OC)C=1C(=NN2C1N=C(C=C2NCC2=CC=C(C=C2)C(C)=O)C)C PLNYJRAFJKJYPQ-UHFFFAOYSA-N 0.000 claims description 6
- YRVKNWLYBSGXOD-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-N-[(4-fluorophenyl)methyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound O1COC2=C1C=CC(=C2)C=2C(=NN1C2N=C(C=C1NCC1=CC=C(C=C1)F)C)C YRVKNWLYBSGXOD-UHFFFAOYSA-N 0.000 claims description 6
- XYFMFPXJQDECRL-UHFFFAOYSA-N 3-(3,4-diethoxyphenyl)-N-[(4-fluorophenyl)methyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C(C)OC=1C=C(C=CC=1OCC)C=1C(=NN2C=1N=C(C=C2NCC1=CC=C(C=C1)F)C)C XYFMFPXJQDECRL-UHFFFAOYSA-N 0.000 claims description 6
- LDVXDXWUCHNADR-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-N-[(4-fluorophenyl)methyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound FC=1C=C(C=CC=1F)C=1C(=NN2C=1N=C(C=C2NCC1=CC=C(C=C1)F)C)C LDVXDXWUCHNADR-UHFFFAOYSA-N 0.000 claims description 6
- RZNHUVAFKGHHQT-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-(naphthalen-1-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NCC3=CC=CC4=CC=CC=C34)N2N=C1C RZNHUVAFKGHHQT-UHFFFAOYSA-N 0.000 claims description 6
- WSKROKBJLCOYIR-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-(pyridin-4-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NCC3=CC=NC=C3)N2N=C1C WSKROKBJLCOYIR-UHFFFAOYSA-N 0.000 claims description 6
- HHJZAOCYINMJSK-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-[(2-methylpyrimidin-4-yl)methyl]pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC=1C=C(C=CC1OC)C=1C(=NN2C1N=C(C=C2NCC2=NC(=NC=C2)C)C)C HHJZAOCYINMJSK-UHFFFAOYSA-N 0.000 claims description 6
- JBKQNEDBXTWVCM-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-[(3-methylsulfonylphenyl)methyl]pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NCC3=CC(=CC=C3)S(C)(=O)=O)N2N=C1C JBKQNEDBXTWVCM-UHFFFAOYSA-N 0.000 claims description 6
- XYZQGIPODNTXIL-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-[(4-methylsulfonylphenyl)methyl]pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NCC3=CC=C(C=C3)S(C)(=O)=O)N2N=C1C XYZQGIPODNTXIL-UHFFFAOYSA-N 0.000 claims description 6
- LSKFDIAWFVSIIE-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-[(6-methylpyridin-3-yl)methyl]pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NCC3=CC=C(C)N=C3)N2N=C1C LSKFDIAWFVSIIE-UHFFFAOYSA-N 0.000 claims description 6
- TXNBLAIOWIQZOL-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-[[4-(trifluoromethoxy)phenyl]methyl]pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NCC3=CC=C(OC(F)(F)F)C=C3)N2N=C1C TXNBLAIOWIQZOL-UHFFFAOYSA-N 0.000 claims description 6
- KZNLFTCAGUPSBF-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-n-(pyridin-2-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NCC=3N=CC=CC=3)N2N=C1C KZNLFTCAGUPSBF-UHFFFAOYSA-N 0.000 claims description 6
- OBSBKQPPLHSZBU-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-n-[(4-methylphenyl)methyl]pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NCC=3C=CC(C)=CC=3)N2N=C1C OBSBKQPPLHSZBU-UHFFFAOYSA-N 0.000 claims description 6
- YZNYXPQMGPQDKU-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-5-methyl-N-(pyridin-4-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NCC3=CC=NC=C3)N2N=C1 YZNYXPQMGPQDKU-UHFFFAOYSA-N 0.000 claims description 6
- ASZGXGJTXVZMTQ-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-5-methyl-N-[(3-methylsulfonylphenyl)methyl]pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC=1C=C(C=CC1OC)C=1C=NN2C1N=C(C=C2NCC2=CC(=CC=C2)S(=O)(=O)C)C ASZGXGJTXVZMTQ-UHFFFAOYSA-N 0.000 claims description 6
- PJVBPZOSKYBCLZ-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-N-[(6-methoxypyridin-3-yl)methyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC=1C=C(C=CC=1OC)C=1C(=NN2C=1N=C(C=C2NCC=1C=NC(=CC=1)OC)C)C PJVBPZOSKYBCLZ-UHFFFAOYSA-N 0.000 claims description 6
- XNOGISXLVUBYCR-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-N-[[4-(dimethylamino)phenyl]methyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC=1C=C(C=CC=1OC)C=1C(=NN2C=1N=C(C=C2NCC1=CC=C(C=C1)N(C)C)C)C XNOGISXLVUBYCR-UHFFFAOYSA-N 0.000 claims description 6
- CHFHLLRPKVPRKX-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-[(4-fluorophenyl)methyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NCC=3C=CC(F)=CC=3)N2N=C1C CHFHLLRPKVPRKX-UHFFFAOYSA-N 0.000 claims description 6
- TWCYMPJYRKTZKP-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-[(4-methoxyphenyl)methyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1CNC1=CC(C)=NC2=C(C=3C=C(OC)C(OC)=CC=3)C(C)=NN12 TWCYMPJYRKTZKP-UHFFFAOYSA-N 0.000 claims description 6
- OQFGORVPLHVXLZ-UHFFFAOYSA-N 3-(3-fluoro-4-methoxyphenyl)-2,5-dimethyl-N-[(4-methylphenyl)methyl]pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(F)C=C(C=C1)C1=C2N=C(C)C=C(NCC3=CC=C(C)C=C3)N2N=C1C OQFGORVPLHVXLZ-UHFFFAOYSA-N 0.000 claims description 6
- NYBPLWUILHDZPU-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2,5-dimethyl-n-(pyridin-3-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=C2N=C(C)C=C(NCC=3C=NC=CC=3)N2N=C1C NYBPLWUILHDZPU-UHFFFAOYSA-N 0.000 claims description 6
- XPASZNRYTKGLNL-UHFFFAOYSA-N 4-[2,5-dimethyl-7-[(4-methylphenyl)methylamino]pyrazolo[1,5-a]pyrimidin-3-yl]benzene-1,2-diol Chemical compound CC1=NN2C(N=C(C)C=C2NCC2=CC=C(C)C=C2)=C1C1=CC(O)=C(O)C=C1 XPASZNRYTKGLNL-UHFFFAOYSA-N 0.000 claims description 6
- SBUYZGHVERCOOC-UHFFFAOYSA-N 4-[[[3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]amino]methyl]benzenesulfonamide Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NCC3=CC=C(C=C3)S(N)(=O)=O)N2N=C1C SBUYZGHVERCOOC-UHFFFAOYSA-N 0.000 claims description 6
- VYBBORGOFHDGFX-UHFFFAOYSA-N N-[(4-tert-butylphenyl)methyl]-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C(C)(C)(C)C1=CC=C(C=C1)CNC1=CC(=NC=2N1N=C(C=2C1=CC(=C(C=C1)OC)OC)C)C VYBBORGOFHDGFX-UHFFFAOYSA-N 0.000 claims description 6
- FCLOWALYHPZNNC-UHFFFAOYSA-N N-[4-[[[3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]amino]methyl]phenyl]acetamide Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NCC3=CC=C(NC(C)=O)C=C3)N2N=C1C FCLOWALYHPZNNC-UHFFFAOYSA-N 0.000 claims description 6
- UNPTYLLVISAIOS-UHFFFAOYSA-N N-[4-[[[3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]amino]methyl]phenyl]methanesulfonamide Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NCC3=CC=C(NS(C)(=O)=O)C=C3)N2N=C1C UNPTYLLVISAIOS-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- GVNJISSYDZPTMJ-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NCC=3C=C4OCOC4=CC=3)N2N=C1C GVNJISSYDZPTMJ-UHFFFAOYSA-N 0.000 claims description 6
- DKLSLBVMZJPYMK-UHFFFAOYSA-N n-benzyl-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NCC=3C=CC=CC=3)N2N=C1C DKLSLBVMZJPYMK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- UTRCFKVNFNKJSD-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-N-[(4-fluorophenyl)methyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC=1C=C(C=CC=1Cl)C=1C(=NN2C=1N=C(C=C2NCC1=CC=C(C=C1)F)C)C UTRCFKVNFNKJSD-UHFFFAOYSA-N 0.000 claims description 5
- YVAZHGJQDDGRFS-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-[[4-(trifluoromethyl)phenyl]methyl]pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NCC3=CC=C(C=C3)C(F)(F)F)N2N=C1C YVAZHGJQDDGRFS-UHFFFAOYSA-N 0.000 claims description 5
- LLWABBJTBHVXBO-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-2-methyl-5-propan-2-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC=1C=C(C=CC=1OC)C=1C(=NN2C=1N=C(C=C2NCC1=CC=C(C=C1)F)C(C)C)C LLWABBJTBHVXBO-UHFFFAOYSA-N 0.000 claims description 5
- IAWYQMLLMLBWJL-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2,5-dimethyl-n-(pyridin-4-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=C2N=C(C)C=C(NCC=3C=CN=CC=3)N2N=C1C IAWYQMLLMLBWJL-UHFFFAOYSA-N 0.000 claims description 5
- HBVPEDQMSBLKBA-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NCC=3C=CC(Cl)=CC=3)N2N=C1C HBVPEDQMSBLKBA-UHFFFAOYSA-N 0.000 claims description 5
- KJIVTWLYHQWWEI-UHFFFAOYSA-N n-benzyl-2,5-dimethyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(C)=CC=3)C(C)=NN2C=1NCC1=CC=CC=C1 KJIVTWLYHQWWEI-UHFFFAOYSA-N 0.000 claims description 5
- BLORPCXLWMVVJW-UHFFFAOYSA-N 2,5-dimethyl-3-(4-methylphenyl)-n-(pyridin-2-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(C)=CC=3)C(C)=NN2C=1NCC1=CC=CC=N1 BLORPCXLWMVVJW-UHFFFAOYSA-N 0.000 claims description 4
- HTFBQOOCCCCUIM-UHFFFAOYSA-N 2,5-dimethyl-3-(4-methylphenyl)-n-(pyridin-3-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(C)=CC=3)C(C)=NN2C=1NCC1=CC=CN=C1 HTFBQOOCCCCUIM-UHFFFAOYSA-N 0.000 claims description 4
- LHENGJOOEQGAQL-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-(1-pyridin-4-ylethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NC(C)C3=CC=NC=C3)N2N=C1C LHENGJOOEQGAQL-UHFFFAOYSA-N 0.000 claims description 4
- TZPLIZAIMLZYFK-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-5-methylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC=1C=C(C=CC=1OC)C=1C=NN2C=1N=C(C=C2NCC1=CC=C(C=C1)F)C TZPLIZAIMLZYFK-UHFFFAOYSA-N 0.000 claims description 4
- GGELKXVVOOVMHD-UHFFFAOYSA-N 3-(4-chlorophenyl)-2,5-dimethyl-n-(pyridin-2-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(Cl)=CC=3)C(C)=NN2C=1NCC1=CC=CC=N1 GGELKXVVOOVMHD-UHFFFAOYSA-N 0.000 claims description 4
- GABZCFOSPNLXNR-UHFFFAOYSA-N 3-(4-chlorophenyl)-2,5-dimethyl-n-(pyridin-3-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(Cl)=CC=3)C(C)=NN2C=1NCC1=CC=CN=C1 GABZCFOSPNLXNR-UHFFFAOYSA-N 0.000 claims description 4
- OYHJVHZXPNKLBE-UHFFFAOYSA-N 3-(4-fluorophenyl)-2,5-dimethyl-n-(pyridin-2-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(F)=CC=3)C(C)=NN2C=1NCC1=CC=CC=N1 OYHJVHZXPNKLBE-UHFFFAOYSA-N 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- ZMJVVFIXHBZQRZ-UHFFFAOYSA-N N-[(4-fluorophenyl)methyl]-2,5-dimethyl-3-(3,4,5-trimethoxyphenyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=CC(=CC(OC)=C1OC)C1=C2N=C(C)C=C(NCC3=CC=C(F)C=C3)N2N=C1C ZMJVVFIXHBZQRZ-UHFFFAOYSA-N 0.000 claims description 4
- SNQBEMBVRUDSML-UHFFFAOYSA-N N-[(4-fluorophenyl)methyl]-2,5-dimethyl-3-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC=C(C=C1)CNC1=CC(=NC=2N1N=C(C2C2=CC=NC=C2)C)C SNQBEMBVRUDSML-UHFFFAOYSA-N 0.000 claims description 4
- VNTMFBJNUXCTBD-UHFFFAOYSA-N methyl 4-[7-[(4-fluorophenyl)methylamino]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-3-yl]benzoate Chemical compound FC1=CC=C(C=C1)CNC1=CC(=NC=2N1N=C(C=2C1=CC=C(C(=O)OC)C=C1)C)C VNTMFBJNUXCTBD-UHFFFAOYSA-N 0.000 claims description 4
- UPIMPCRSIJLSHJ-UHFFFAOYSA-N n-benzyl-3-(4-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound N12N=CC(C=3C=CC(Cl)=CC=3)=C2N=C(C)C=C1NCC1=CC=CC=C1 UPIMPCRSIJLSHJ-UHFFFAOYSA-N 0.000 claims description 4
- ZWGSTFWTZFHNGQ-UHFFFAOYSA-N n-benzyl-3-(4-fluorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(F)=CC=3)C(C)=NN2C=1NCC1=CC=CC=C1 ZWGSTFWTZFHNGQ-UHFFFAOYSA-N 0.000 claims description 4
- YKUISZTZWQZJHL-UHFFFAOYSA-N n-benzyl-3-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound N12N=CC(C=3C=CC(F)=CC=3)=C2N=C(C)C=C1NCC1=CC=CC=C1 YKUISZTZWQZJHL-UHFFFAOYSA-N 0.000 claims description 4
- NHJLQMHGLNWRDN-UHFFFAOYSA-N 3-(4-fluorophenyl)-2,5-dimethyl-n-(pyridin-3-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(F)=CC=3)C(C)=NN2C=1NCC1=CC=CN=C1 NHJLQMHGLNWRDN-UHFFFAOYSA-N 0.000 claims description 3
- DMYXIGXUOWRJHK-UHFFFAOYSA-N N-[(4-fluorophenyl)methyl]-2,5-dimethyl-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC=C(C=C1)CNC1=CC(=NC=2N1N=C(C=2C1=CC=C(C=C1)C(F)(F)F)C)C DMYXIGXUOWRJHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- UKZLNCVELPIRDJ-UHFFFAOYSA-N 2,5-dimethyl-3-phenyl-n-(pyridin-3-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC=CC=3)C(C)=NN2C=1NCC1=CC=CN=C1 UKZLNCVELPIRDJ-UHFFFAOYSA-N 0.000 claims description 2
- XFGHBFSTNAEDGA-UHFFFAOYSA-N 2,5-dimethyl-N-(pyridin-3-ylmethyl)-3-thiophen-2-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(N=C(C=C2NCC=2C=NC=CC2)C)=C1C=1SC=CC1 XFGHBFSTNAEDGA-UHFFFAOYSA-N 0.000 claims description 2
- FYVLQCVXOQASEQ-UHFFFAOYSA-N 2,5-dimethyl-N-(pyridin-4-ylmethyl)-3-thiophen-2-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(N=C(C)C=C2NCC2=CC=NC=C2)=C1C1=CC=CS1 FYVLQCVXOQASEQ-UHFFFAOYSA-N 0.000 claims description 2
- QZLVKBACEAGELW-UHFFFAOYSA-N n-benzyl-3-phenyl-5-propan-2-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound N12N=CC(C=3C=CC=CC=3)=C2N=C(C(C)C)C=C1NCC1=CC=CC=C1 QZLVKBACEAGELW-UHFFFAOYSA-N 0.000 claims description 2
- IMBYBEIFZUYXOL-UHFFFAOYSA-N n-benzyl-5-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound N12N=CC(C=3C=CC=CC=3)=C2N=C(C)C=C1NCC1=CC=CC=C1 IMBYBEIFZUYXOL-UHFFFAOYSA-N 0.000 claims description 2
- 208000009341 RNA Virus Infections Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- SKYYVIAKGNSFKA-UHFFFAOYSA-N 2,5-dimethyl-3-(4-methylphenyl)-n-(2-phenylethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(C)=CC=3)C(C)=NN2C=1NCCC1=CC=CC=C1 SKYYVIAKGNSFKA-UHFFFAOYSA-N 0.000 description 2
- VVZNUWXJECAIEH-UHFFFAOYSA-N 2,5-dimethyl-3-(4-methylphenyl)-n-phenylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(C)=CC=3)C(C)=NN2C=1NC1=CC=CC=C1 VVZNUWXJECAIEH-UHFFFAOYSA-N 0.000 description 2
- NUXISAACSNJHDF-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-(2-pyridin-2-ylethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NCCC3=NC=CC=C3)N2N=C1C NUXISAACSNJHDF-UHFFFAOYSA-N 0.000 description 2
- UYKJTCZRJQLMPM-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-(2-pyridin-4-ylethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NCCC3=CC=NC=C3)N2N=C1C UYKJTCZRJQLMPM-UHFFFAOYSA-N 0.000 description 2
- WNOYEXOJDPSFNS-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-(2-thiophen-2-ylethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC=1C=C(C=CC=1OC)C=1C(=NN2C=1N=C(C=C2NCCC=1SC=CC=1)C)C WNOYEXOJDPSFNS-UHFFFAOYSA-N 0.000 description 2
- YXAVJYGWTURGOX-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NC3=CC=C(C=C3)C(F)(F)F)N2N=C1C YXAVJYGWTURGOX-UHFFFAOYSA-N 0.000 description 2
- UXUUDVCETRUBID-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-pyrazin-2-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC=1C=C(C=CC=1OC)C=1C(=NN2C=1N=C(C=C2NC1=NC=CN=C1)C)C UXUUDVCETRUBID-UHFFFAOYSA-N 0.000 description 2
- RFEVLOIMXCNHAD-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NC3=CC=NC=C3)N2N=C1C RFEVLOIMXCNHAD-UHFFFAOYSA-N 0.000 description 2
- VURZCMNIVDQORF-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-n-(2-phenylpropyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NCC(C)C=3C=CC=CC=3)N2N=C1C VURZCMNIVDQORF-UHFFFAOYSA-N 0.000 description 2
- AMXUFPMAXHKBSH-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-n-(3-methylphenyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=C(C)C=CC=3)N2N=C1C AMXUFPMAXHKBSH-UHFFFAOYSA-N 0.000 description 2
- QUKFLFWESGWQKA-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-n-(3-phenylpropyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NCCCC=3C=CC=CC=3)N2N=C1C QUKFLFWESGWQKA-UHFFFAOYSA-N 0.000 description 2
- WBVXWINDSWNHNL-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-n-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=CC(C)=CC=3)N2N=C1C WBVXWINDSWNHNL-UHFFFAOYSA-N 0.000 description 2
- XGABPXXGNNEMGY-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-n-(4-propan-2-ylphenyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=CC(=CC=3)C(C)C)N2N=C1C XGABPXXGNNEMGY-UHFFFAOYSA-N 0.000 description 2
- BIPGDOIEJKNLQD-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-n-phenylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=CC=CC=3)N2N=C1C BIPGDOIEJKNLQD-UHFFFAOYSA-N 0.000 description 2
- KFRGNTUBXJOJQC-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(3,4-dimethylphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=C(C)C(C)=CC=3)N2N=C1C KFRGNTUBXJOJQC-UHFFFAOYSA-N 0.000 description 2
- VLFYYEYZYXGPIK-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(3,5-dimethylphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=C(C)C=C(C)C=3)N2N=C1C VLFYYEYZYXGPIK-UHFFFAOYSA-N 0.000 description 2
- FJANPTMLIPPULK-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(3-methoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=CC=CC(NC=2N3N=C(C)C(=C3N=C(C)C=2)C=2C=C(OC)C(OC)=CC=2)=C1 FJANPTMLIPPULK-UHFFFAOYSA-N 0.000 description 2
- AXJVIXIZTRFBNY-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(4-ethylphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(CC)=CC=C1NC1=CC(C)=NC2=C(C=3C=C(OC)C(OC)=CC=3)C(C)=NN12 AXJVIXIZTRFBNY-UHFFFAOYSA-N 0.000 description 2
- WYBXCNZPEDEADV-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(4-fluorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=CC(F)=CC=3)N2N=C1C WYBXCNZPEDEADV-UHFFFAOYSA-N 0.000 description 2
- YNZJWBWAYQSWFE-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(4-methoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1NC1=CC(C)=NC2=C(C=3C=C(OC)C(OC)=CC=3)C(C)=NN12 YNZJWBWAYQSWFE-UHFFFAOYSA-N 0.000 description 2
- BYFQRXUYXJTOOQ-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-[2-(2,4-dimethoxyphenyl)ethyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=CC(OC)=CC=C1CCNC1=CC(C)=NC2=C(C=3C=C(OC)C(OC)=CC=3)C(C)=NN12 BYFQRXUYXJTOOQ-UHFFFAOYSA-N 0.000 description 2
- JPTMOJSVZSQATI-UHFFFAOYSA-N 3-(4-fluorophenyl)-2,5-dimethyl-n-(1-phenylethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C=CC=CC=1C(C)NC(N1N=C2C)=CC(C)=NC1=C2C1=CC=C(F)C=C1 JPTMOJSVZSQATI-UHFFFAOYSA-N 0.000 description 2
- JPGIHFSUHQXYTM-UHFFFAOYSA-N N-(2,3-dihydro-1H-inden-2-yl)-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound COC=1C=C(C=CC=1OC)C=1C(=NN2C=1N=C(C=C2NC1CC2=CC=CC=C2C1)C)C JPGIHFSUHQXYTM-UHFFFAOYSA-N 0.000 description 2
- LOJCFSSIILNXRK-UHFFFAOYSA-N N-[3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]-1,2-oxazol-3-amine Chemical compound COC1=C(OC)C=C(C=C1)C1=C2N=C(C)C=C(NC3=NOC=C3)N2N=C1C LOJCFSSIILNXRK-UHFFFAOYSA-N 0.000 description 2
- SOXFTPBZGLOGOV-UHFFFAOYSA-N N-[3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]-5-methyl-1,3-thiazol-2-amine Chemical compound COC=1C=C(C=CC1OC)C=1C(=NN2C1N=C(C=C2NC=2SC(=CN2)C)C)C SOXFTPBZGLOGOV-UHFFFAOYSA-N 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- VHTGBNJQGWEEEP-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=C(Cl)C(Cl)=CC=3)N2N=C1C VHTGBNJQGWEEEP-UHFFFAOYSA-N 0.000 description 2
- XRCMLCVAHXBRPZ-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=C(Cl)C=C(Cl)C=3)N2N=C1C XRCMLCVAHXBRPZ-UHFFFAOYSA-N 0.000 description 2
- TUMVOTSAGZKCJT-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=C(Cl)C(C)=CC=3)N2N=C1C TUMVOTSAGZKCJT-UHFFFAOYSA-N 0.000 description 2
- DOVMGZAJTAWKCN-UHFFFAOYSA-N n-(3-chlorophenyl)-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=C(Cl)C=CC=3)N2N=C1C DOVMGZAJTAWKCN-UHFFFAOYSA-N 0.000 description 2
- OAAPHHPKGFASTQ-UHFFFAOYSA-N n-(4-bromophenyl)-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=CC(Br)=CC=3)N2N=C1C OAAPHHPKGFASTQ-UHFFFAOYSA-N 0.000 description 2
- XFOOMXSKXZHVLR-UHFFFAOYSA-N n-(4-butylphenyl)-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=CC(C)=NC2=C(C=3C=C(OC)C(OC)=CC=3)C(C)=NN12 XFOOMXSKXZHVLR-UHFFFAOYSA-N 0.000 description 2
- KRFPJLOHLFQHKZ-UHFFFAOYSA-N n-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=CC(Cl)=CC=3)N2N=C1C KRFPJLOHLFQHKZ-UHFFFAOYSA-N 0.000 description 2
- NHUVQGZBVRTXKR-UHFFFAOYSA-N n-(cyclohexylmethyl)-2,5-dimethyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(C)=CC=3)C(C)=NN2C=1NCC1CCCCC1 NHUVQGZBVRTXKR-UHFFFAOYSA-N 0.000 description 2
- WRRUEZHGAFDWSR-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NCCC=3C=CC(Cl)=CC=3)N2N=C1C WRRUEZHGAFDWSR-UHFFFAOYSA-N 0.000 description 2
- UKOIBYZSDJFSMN-UHFFFAOYSA-N n-[4-[[3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]amino]phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC=3C=CC(NC(C)=O)=CC=3)N2N=C1C UKOIBYZSDJFSMN-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- OTDVQWJNYFFJJP-UHFFFAOYSA-N 2-ethyl-n-(3-imidazol-1-ylpropyl)-5-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC=CC=3)C(CC)=NN2C=1NCCCN1C=CN=C1 OTDVQWJNYFFJJP-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- MPODYFBBTCNTCO-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(4-ethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(OCC)=CC=C1NC1=CC(C)=NC2=C(C=3C=C(OC)C(OC)=CC=3)C(C)=NN12 MPODYFBBTCNTCO-UHFFFAOYSA-N 0.000 description 1
- VRLKUMSJTXBEKD-UHFFFAOYSA-N 3-(4-chlorophenyl)-2,5-dimethyl-n-[2-(4-methylphenyl)ethyl]pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(Cl)=CC=3)C(C)=NN2C=1NCCC1=CC=C(C)C=C1 VRLKUMSJTXBEKD-UHFFFAOYSA-N 0.000 description 1
- BBYXGWXBMARCIX-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-methyl-n-(2-phenylethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound N12N=CC(C=3C=CC(Cl)=CC=3)=C2N=C(C)C=C1NCCC1=CC=CC=C1 BBYXGWXBMARCIX-UHFFFAOYSA-N 0.000 description 1
- WOTGUOGOEKRSLA-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(3-imidazol-1-ylpropyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(Cl)=CC=3)C(C)=NN2C=1NCCCN1C=CN=C1 WOTGUOGOEKRSLA-UHFFFAOYSA-N 0.000 description 1
- SLWUMZKNTLKMGT-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(3-imidazol-1-ylpropyl)-5-methylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound N12N=CC(C=3C=CC(Cl)=CC=3)=C2N=C(C)C=C1NCCCN1C=CN=C1 SLWUMZKNTLKMGT-UHFFFAOYSA-N 0.000 description 1
- BRXPVKGPZXCGLH-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(4-methoxyphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1NC1=CC(C)=NC2=C(C=3C=CC(Cl)=CC=3)C=NN12 BRXPVKGPZXCGLH-UHFFFAOYSA-N 0.000 description 1
- FOXNLHOBRSPHSJ-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[2-(3,4-dimethoxyphenyl)ethyl]-5-methylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=CC(C)=NC2=C(C=3C=CC(Cl)=CC=3)C=NN12 FOXNLHOBRSPHSJ-UHFFFAOYSA-N 0.000 description 1
- JFLIPBNGOBISKB-UHFFFAOYSA-N 3-(4-fluorophenyl)-2,5-dimethyl-n-(2-phenylethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(F)=CC=3)C(C)=NN2C=1NCCC1=CC=CC=C1 JFLIPBNGOBISKB-UHFFFAOYSA-N 0.000 description 1
- QOJUCMRVQZWAJF-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2,5-dimethyl-n-(2-pyridin-2-ylethyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=C2N=C(C)C=C(NCCC=3N=CC=CC=3)N2N=C1C QOJUCMRVQZWAJF-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- YPKOXFCWPQFTJD-UHFFFAOYSA-N 5-tert-butyl-n-(3-imidazol-1-ylpropyl)-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound N12N=CC(C=3C=CC=CC=3)=C2N=C(C(C)(C)C)C=C1NCCCN1C=CN=C1 YPKOXFCWPQFTJD-UHFFFAOYSA-N 0.000 description 1
- MYYIODNSPPABMS-UHFFFAOYSA-N 5-tert-butyl-n-[2-(cyclohexen-1-yl)ethyl]-3-(4-fluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C(C)(C)C)=NC2=C(C=3C=CC(F)=CC=3)C(C)=NN2C=1NCCC1=CCCCC1 MYYIODNSPPABMS-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- PLMVAJXVRLYYRQ-UHFFFAOYSA-N N-(3-imidazol-1-ylpropyl)-2,5-dimethyl-3-thiophen-2-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound N1(C=NC=C1)CCCNC1=CC(=NC=2N1N=C(C2C=2SC=CC2)C)C PLMVAJXVRLYYRQ-UHFFFAOYSA-N 0.000 description 1
- DGRPYNIHNJXTIL-UHFFFAOYSA-N N-[3-(1-imidazolyl)propyl]-2-methyl-3-phenyl-5-propyl-7-pyrazolo[1,5-a]pyrimidinamine Chemical compound N12N=C(C)C(C=3C=CC=CC=3)=C2N=C(CCC)C=C1NCCCN1C=CN=C1 DGRPYNIHNJXTIL-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- SJJHQXJYOLFETN-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-3-(4-methoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=C2N=C(C)C=C(NCCCN3C=NC=C3)N2N=C1C SJJHQXJYOLFETN-UHFFFAOYSA-N 0.000 description 1
- BWTLVTYHAQFLLX-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-ethyl-5-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC=CC=3)C(CC)=NN2C=1NCCC1=CC=C(OC)C(OC)=C1 BWTLVTYHAQFLLX-UHFFFAOYSA-N 0.000 description 1
- HCJZQRLQYLEHMC-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-fluorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=CC(C)=NC2=C(C=3C=CC(F)=CC=3)C(C)=NN12 HCJZQRLQYLEHMC-UHFFFAOYSA-N 0.000 description 1
- JJJOKNIGXHDIEJ-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=CC(C)=NC2=C(C=3C=CC(F)=CC=3)C=NN12 JJJOKNIGXHDIEJ-UHFFFAOYSA-N 0.000 description 1
- VAAZCMVTJRHATC-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-5-methyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=CC(C)=NC2=C(C=3C=CC(C)=CC=3)C=NN12 VAAZCMVTJRHATC-UHFFFAOYSA-N 0.000 description 1
- AITOBCAVQXSDET-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-5-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=CC(C)=NC2=C(C=3C=CC=CC=3)C=NN12 AITOBCAVQXSDET-UHFFFAOYSA-N 0.000 description 1
- VJLVGUSKMUQSMR-UHFFFAOYSA-N n-[2-(cyclohexen-1-yl)ethyl]-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NCCC=3CCCCC=3)N2N=C1C VJLVGUSKMUQSMR-UHFFFAOYSA-N 0.000 description 1
- RYFDSPQOWOQUQX-UHFFFAOYSA-N n-[2-(cyclohexen-1-yl)ethyl]-3-(4-fluorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(F)=CC=3)C(C)=NN2C=1NCCC1=CCCCC1 RYFDSPQOWOQUQX-UHFFFAOYSA-N 0.000 description 1
- UXTCUWPLWOZTCW-UHFFFAOYSA-N n-cyclohexyl-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC3CCCCC3)N2N=C1C UXTCUWPLWOZTCW-UHFFFAOYSA-N 0.000 description 1
- BOUDAPBUAGZQPU-UHFFFAOYSA-N n-cyclopentyl-3-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C2N=C(C)C=C(NC3CCCC3)N2N=C1C BOUDAPBUAGZQPU-UHFFFAOYSA-N 0.000 description 1
- INDNKTRXQUYXNL-UHFFFAOYSA-N n-cyclopentyl-3-(4-fluorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C=CC(F)=CC=3)C(C)=NN2C=1NC1CCCC1 INDNKTRXQUYXNL-UHFFFAOYSA-N 0.000 description 1
- 231100000062 no-observed-adverse-effect level Toxicity 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14152202 | 2014-01-22 | ||
| EP14152202.9 | 2014-01-22 | ||
| PCT/EP2015/051177 WO2015110491A2 (en) | 2014-01-22 | 2015-01-21 | Pyrazolo[1,5-a]pyrimidin-7-amine derivatives useful in therapy |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017503830A JP2017503830A (ja) | 2017-02-02 |
| JP2017503830A5 true JP2017503830A5 (OSRAM) | 2018-02-22 |
| JP6509238B2 JP6509238B2 (ja) | 2019-05-08 |
Family
ID=49989585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016548033A Active JP6509238B2 (ja) | 2014-01-22 | 2015-01-21 | 治療に有用なピラゾロ［１，５−ａ］ピリミジン−７−アミン誘導体 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9963455B2 (OSRAM) |
| EP (1) | EP3096762B1 (OSRAM) |
| JP (1) | JP6509238B2 (OSRAM) |
| CN (1) | CN106061975B (OSRAM) |
| AU (1) | AU2015208205B2 (OSRAM) |
| BR (1) | BR112016016798B1 (OSRAM) |
| CA (1) | CA2935658C (OSRAM) |
| ES (1) | ES2954126T3 (OSRAM) |
| RU (1) | RU2689788C2 (OSRAM) |
| WO (1) | WO2015110491A2 (OSRAM) |
| ZA (1) | ZA201605666B (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3057408A1 (en) * | 2017-04-05 | 2018-10-11 | Curovir Ab | Heteroaromatic compounds useful in therapy |
| BR112020014431A2 (pt) * | 2018-01-17 | 2020-12-01 | Glaxosmithkline Intellectual Property Development Limited | inibidores de pl4kiiibeta |
| CN108727386A (zh) * | 2018-07-16 | 2018-11-02 | 广州医科大学 | 一种吡唑并嘧啶类化合物及其制备方法和用途 |
| TWI811428B (zh) | 2018-08-21 | 2023-08-11 | 日商杏林製藥股份有限公司 | 雙環雜芳香環衍生物 |
| WO2020074160A1 (en) | 2018-10-10 | 2020-04-16 | Curovir Ab | Condensed pyrimidine or pyridazine derivatives as antiviral agents |
| WO2020074159A1 (en) * | 2018-10-10 | 2020-04-16 | Curovir Ab | 2,6-dimethyl-n-((pyridin-4-yl)methyl)imidazo[1,2-b]pyridazin-8-amine and 2,5-dimethyl-n-[(pyridin-4-yl)methyl]pyrazolo[1,5-a]pyrimidin-7-amine derivatives for treating viral infections |
| CN109988172B (zh) * | 2019-01-10 | 2020-09-29 | 石家庄学院 | 一种吡唑并[1,5-a]嘧啶类杂环化合物及衍生物的合成方法 |
| EP4028131B1 (en) | 2019-08-20 | 2023-11-22 | Curovir Ab | Heteroaromatic compounds useful in therapy |
| WO2024184442A1 (en) | 2023-03-09 | 2024-09-12 | Curovir Ab | Compound and formulation for systemic therapy by oral transmucosal administration |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2585462B2 (ja) * | 1989-10-25 | 1997-02-26 | 株式会社大塚製薬工場 | ピラゾロ［１，５―ａ］ピリミジン誘導体 |
| AU651986B2 (en) * | 1991-04-22 | 1994-08-11 | Otsuka Pharmaceutical Factory, Inc. | Pyrazolo{1,5-a}pyrimidine derivative and anti-inflammatory containing the same |
| US6313124B1 (en) | 1997-07-23 | 2001-11-06 | Dupont Pharmaceuticals Company | Tetrazine bicyclic compounds |
| AU7738100A (en) * | 1999-09-30 | 2001-04-30 | Neurogen Corporation | Certain alkylene diamine-substituted pyrazolo(1,5,-a)-1,5-pyrimidines and pyrazolo(1,5-a)-1,3,5-triazines |
| ATE365740T1 (de) * | 2002-05-10 | 2007-07-15 | Smithkline Beecham Corp | Substituierte pyrazolopyrimidine |
| MXPA05002572A (es) * | 2002-09-04 | 2005-09-08 | Schering Corp | Compuestos pirazolo[1,5-a]pirimidinas como inhibidores de cinasa depentes de ciclina. |
| US7601724B2 (en) * | 2002-09-04 | 2009-10-13 | Schering Corporation | Substituted pyrazolo[1,5-a]pyrimidines as protein kinase inhibitors |
| GB0519957D0 (en) * | 2005-09-30 | 2005-11-09 | Sb Pharmco Inc | Chemical compound |
| WO2010086040A1 (en) * | 2009-01-29 | 2010-08-05 | Biomarin Iga, Ltd. | Pyrazolo-pyrimidines for treatment of duchenne muscular dystrophy |
| KR101478889B1 (ko) * | 2010-02-26 | 2015-01-02 | 미쓰비시 타나베 파마 코퍼레이션 | 피라졸로피리미딘 화합물 및 ｐｄｅ10 억제제로서의 그의 용도 |
| US8633198B1 (en) * | 2011-09-20 | 2014-01-21 | Nant Holdings Ip, Llc | Small molecule inhibitors of influenza A RNA-dependent RNA polymerase |
-
2015
- 2015-01-21 AU AU2015208205A patent/AU2015208205B2/en active Active
- 2015-01-21 BR BR112016016798-8A patent/BR112016016798B1/pt active IP Right Grant
- 2015-01-21 RU RU2016134130A patent/RU2689788C2/ru active
- 2015-01-21 EP EP15702990.1A patent/EP3096762B1/en active Active
- 2015-01-21 US US15/107,930 patent/US9963455B2/en active Active
- 2015-01-21 WO PCT/EP2015/051177 patent/WO2015110491A2/en not_active Ceased
- 2015-01-21 ES ES15702990T patent/ES2954126T3/es active Active
- 2015-01-21 CN CN201580005612.2A patent/CN106061975B/zh active Active
- 2015-01-21 JP JP2016548033A patent/JP6509238B2/ja active Active
- 2015-01-21 CA CA2935658A patent/CA2935658C/en active Active
-
2016
- 2016-08-16 ZA ZA2016/05666A patent/ZA201605666B/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017503830A5 (OSRAM) | ||
| RU2016134130A (ru) | ПИРАЗОЛО[1,5-а]ПИРИМИДИНЫ В КАЧЕСТВЕ ПРОТИВОВИРУСНЫХ СОЕДИНЕНИЙ | |
| JP2018522861A5 (OSRAM) | ||
| RU2018102449A (ru) | Производные пиразоло[1,5-a]триазин-4-амина, применимые в терапии | |
| AU2021246118B2 (en) | Methods of treating coronavirus | |
| JP2008516986A5 (OSRAM) | ||
| JP2021503458A5 (OSRAM) | ||
| JP2018521092A5 (OSRAM) | ||
| JP2013209405A5 (OSRAM) | ||
| JP2007529421A5 (OSRAM) | ||
| JP2019501879A5 (OSRAM) | ||
| JP2017522273A5 (OSRAM) | ||
| JP2019505529A5 (OSRAM) | ||
| JP2020516599A5 (OSRAM) | ||
| RU2011117927A (ru) | Карбаматное соединение или его соль | |
| JP2015521156A5 (OSRAM) | ||
| RU2014139825A (ru) | Производные ингенола для реактивации латентного вируса вич | |
| RU2018123714A (ru) | 1,3,4-тиадиазольные соединения и их применение в лечении рака | |
| JP2015522592A5 (OSRAM) | ||
| RU2006138606A (ru) | Ингибиторы киназы | |
| RU2015136817A (ru) | N-гетероарилзамещенные производные анилина в качестве антивирусных препаратов против вируса гепатита с | |
| JP2015526504A5 (OSRAM) | ||
| RU2007122450A (ru) | Применение агониста рецептора 5-нт6 для лечения и профилактики нейродегенеративных заболеваний | |
| FI3947384T3 (fi) | Isokromeenijohdannaisia fosfoinositidi-3-kinaasien estäjinä | |
| RU2009128186A (ru) | Производные трициклических аминов в качестве ингибиторов тирозинкиназы |