JP2017503830A5 - - Google Patents
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- 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
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- 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
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- 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
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- 231100000062 no-observed-adverse-effect level Toxicity 0.000 description 1
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- 238000002560 therapeutic procedure Methods 0.000 description 1
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| PCT/EP2015/051177 WO2015110491A2 (en) | 2014-01-22 | 2015-01-21 | Pyrazolo[1,5-a]pyrimidin-7-amine derivatives useful in therapy |
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| CN110520424B (zh) * | 2017-04-05 | 2022-06-21 | 库洛维公司 | 用于疗法的杂芳族化合物 |
| TWI795510B (zh) * | 2018-01-17 | 2023-03-11 | 英商葛蘭素史密斯克藍智慧財產發展有限公司 | PI4KIIIβ抑制劑 |
| 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 |
| CN118084937A (zh) | 2018-08-21 | 2024-05-28 | 杏林制药株式会社 | 双环杂芳族环衍生物 |
| WO2020074160A1 (en) | 2018-10-10 | 2020-04-16 | Curovir Ab | Condensed pyrimidine or pyridazine derivatives as antiviral agents |
| US12319696B2 (en) * | 2018-10-10 | 2025-06-03 | 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 |
| WO2021032611A1 (en) | 2019-08-20 | 2021-02-25 | Curovir Ab | Heteroaromatic compounds useful in therapy |
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| 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 |
| CA2107479C (en) * | 1991-04-22 | 1997-12-16 | Makoto Inoue | Pyrazolo[1,5-a]pyrimidine derivatives and anti-inflammatory agent containing the same |
| US6313124B1 (en) | 1997-07-23 | 2001-11-06 | Dupont Pharmaceuticals Company | Tetrazine bicyclic compounds |
| US6372743B1 (en) * | 1999-09-30 | 2002-04-16 | Neurogen Corporation | Certain alkylene diamine-substituted pyrazlo (1,5-a)-1,5-pyrimidines and pyrazolo (1,5-a) 1,3,5-triazines |
| WO2003095455A2 (en) * | 2002-05-10 | 2003-11-20 | Smithkline Beecham Corporation | Substituted pyrazolopyrimidines |
| MY145332A (en) * | 2002-09-04 | 2012-01-31 | Schering Corp | Trisubstituted 4-aminopyrazolopyrimidines as cyclin dependent kinase inhibitors |
| 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 |
| CA2791166C (en) * | 2010-02-26 | 2014-12-30 | Mitsubishi Tanabe Pharma Corporation | Pyrazolopyrimidine compounds and their use as pde10 inhibitors |
| US8633198B1 (en) * | 2011-09-20 | 2014-01-21 | Nant Holdings Ip, Llc | Small molecule inhibitors of influenza A RNA-dependent RNA polymerase |
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