JP2013534233A5 - - Google Patents
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- JP2013534233A5 JP2013534233A5 JP2013524421A JP2013524421A JP2013534233A5 JP 2013534233 A5 JP2013534233 A5 JP 2013534233A5 JP 2013524421 A JP2013524421 A JP 2013524421A JP 2013524421 A JP2013524421 A JP 2013524421A JP 2013534233 A5 JP2013534233 A5 JP 2013534233A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolo
- methyl
- pyrazol
- pyrimidin
- amino
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 30
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 26
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- -1 heterocyclyl compound Chemical class 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000002207 metabolite Substances 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- UQPXYEYBUROSJF-UHFFFAOYSA-N 1,6-diazaspiro[3.3]heptane Chemical compound N1CCC11CNC1 UQPXYEYBUROSJF-UHFFFAOYSA-N 0.000 claims 1
- WIAQVEOZEVXBLK-UHFFFAOYSA-N 1-(dimethylamino)-3-[4-[[1-[(3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]propan-2-ol Chemical compound C1=NN(CC(O)CN(C)C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCOCC3)C2=N1 WIAQVEOZEVXBLK-UHFFFAOYSA-N 0.000 claims 1
- AIPWKMARVVQHIZ-UHFFFAOYSA-N 1-[(2,3-difluoro-5-morpholin-4-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=C(C=3)N3CCOCC3)F)C2=N1 AIPWKMARVVQHIZ-UHFFFAOYSA-N 0.000 claims 1
- IOHPHOVOIWXLOQ-UHFFFAOYSA-N 1-[(2,3-difluoro-5-piperazin-1-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=C(C=3)N3CCNCC3)F)C2=N1 IOHPHOVOIWXLOQ-UHFFFAOYSA-N 0.000 claims 1
- ZEGGSAUHKBOSRB-UHFFFAOYSA-N 1-[(2,5-difluoro-3-piperazin-1-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCNCC4)C=C(F)C=3)F)C2=N1 ZEGGSAUHKBOSRB-UHFFFAOYSA-N 0.000 claims 1
- IBJINTQEVNSIPA-UHFFFAOYSA-N 1-[(2,6-difluoro-3-morpholin-4-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCOCC4)C=CC=3F)F)C2=N1 IBJINTQEVNSIPA-UHFFFAOYSA-N 0.000 claims 1
- YFDUXROIWMDICD-UHFFFAOYSA-N 1-[(2-chloro-3-morpholin-4-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCOCC4)C=CC=3)Cl)C2=N1 YFDUXROIWMDICD-UHFFFAOYSA-N 0.000 claims 1
- TTXQDRDDHYSWCG-UHFFFAOYSA-N 1-[(2-fluoro-3-morpholin-4-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCOCC4)C=CC=3)F)C2=N1 TTXQDRDDHYSWCG-UHFFFAOYSA-N 0.000 claims 1
- LCLFUUUFFSKKRQ-UHFFFAOYSA-N 1-[(2-fluoro-3-piperazin-1-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCNCC4)C=CC=3)F)C2=N1 LCLFUUUFFSKKRQ-UHFFFAOYSA-N 0.000 claims 1
- DXJLNSJZOYPILI-UHFFFAOYSA-N 1-[(2-fluoro-5-morpholin-4-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=CC=C(C=3)N3CCOCC3)F)C2=N1 DXJLNSJZOYPILI-UHFFFAOYSA-N 0.000 claims 1
- XPNKQYYVMWJGIP-UHFFFAOYSA-N 1-[(2-methyl-3-morpholin-4-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC=C(N2CCOCC2)C(C)=C1CN(C1=N2)N=CC1=CN=C2NC=1C=NN(C)C=1 XPNKQYYVMWJGIP-UHFFFAOYSA-N 0.000 claims 1
- UTOMTFZIGBUZJC-UHFFFAOYSA-N 1-[(3-fluoro-5-morpholin-4-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=C(F)C=3)N3CCOCC3)C2=N1 UTOMTFZIGBUZJC-UHFFFAOYSA-N 0.000 claims 1
- AFJQMCYSUWEOLJ-UHFFFAOYSA-N 1-[(3-fluoro-5-piperazin-1-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=C(F)C=3)N3CCNCC3)C2=N1 AFJQMCYSUWEOLJ-UHFFFAOYSA-N 0.000 claims 1
- KQFDSKUATBKDQT-UHFFFAOYSA-N 1-[(3-morpholin-4-ylphenyl)methyl]-n-[1-(piperidin-3-ylmethyl)pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(NC=2N=C3N(CC=4C=C(C=CC=4)N4CCOCC4)N=CC3=CN=2)C=NN1CC1CCCNC1 KQFDSKUATBKDQT-UHFFFAOYSA-N 0.000 claims 1
- JMLXWLDQGXMEHE-UHFFFAOYSA-N 1-[(3-morpholin-4-ylphenyl)methyl]-n-[1-(pyrrolidin-3-ylmethyl)pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(NC=2N=C3N(CC=4C=C(C=CC=4)N4CCOCC4)N=CC3=CN=2)C=NN1CC1CCNC1 JMLXWLDQGXMEHE-UHFFFAOYSA-N 0.000 claims 1
- QJIWPIMERUHTCJ-UHFFFAOYSA-N 1-[2,4-difluoro-3-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4C(CNCC4)=O)C=CC=3F)F)C2=N1 QJIWPIMERUHTCJ-UHFFFAOYSA-N 0.000 claims 1
- WXELJEBIOJRVCJ-UHFFFAOYSA-N 1-[2-fluoro-3-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4C(CNCC4)=O)C=CC=3)F)C2=N1 WXELJEBIOJRVCJ-UHFFFAOYSA-N 0.000 claims 1
- BTVOZQZBAOSNOE-UHFFFAOYSA-N 1-[2-fluoro-3-[[6-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4C(CNCC4)=O)C=CC=3)F)C2=N1 BTVOZQZBAOSNOE-UHFFFAOYSA-N 0.000 claims 1
- JQUASVYSBGGPMN-UHFFFAOYSA-N 1-[3,4-difluoro-5-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=C(C=3)N3C(CNCC3)=O)F)C2=N1 JQUASVYSBGGPMN-UHFFFAOYSA-N 0.000 claims 1
- RDBOBWQYTXNMOO-UHFFFAOYSA-N 1-[3,4-difluoro-5-[[6-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=C(C=3)N3C(CNCC3)=O)F)C2=N1 RDBOBWQYTXNMOO-UHFFFAOYSA-N 0.000 claims 1
- SPYBDNGMYOLKKT-UHFFFAOYSA-N 1-[3-[4-[[1-[(3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]propyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCCN1N=CC(NC=2N=C3N(CC=4C=C(C=CC=4)N4CCOCC4)N=CC3=CN=2)=C1 SPYBDNGMYOLKKT-UHFFFAOYSA-N 0.000 claims 1
- BNTKLVFPGMSLPS-UHFFFAOYSA-N 1-[3-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3C(CNCC3)=O)C2=N1 BNTKLVFPGMSLPS-UHFFFAOYSA-N 0.000 claims 1
- AZMWRRAPMUJHLW-UHFFFAOYSA-N 1-[3-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperidin-4-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCC(=O)CC3)C2=N1 AZMWRRAPMUJHLW-UHFFFAOYSA-N 0.000 claims 1
- WRQWPHAULJEKEJ-UHFFFAOYSA-N 1-[3-[[6-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3C(CNCC3)=O)C2=N1 WRQWPHAULJEKEJ-UHFFFAOYSA-N 0.000 claims 1
- HLHPEQUSUXNOGX-UHFFFAOYSA-N 1-[3-fluoro-5-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=C(F)C=3)N3C(CNCC3)=O)C2=N1 HLHPEQUSUXNOGX-UHFFFAOYSA-N 0.000 claims 1
- RQAUXJQYPZFDHH-UHFFFAOYSA-N 1-[3-fluoro-5-[[6-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C=C(C=C(F)C=3)N3C(CNCC3)=O)C2=N1 RQAUXJQYPZFDHH-UHFFFAOYSA-N 0.000 claims 1
- OJFIRFVBSDGLRA-UHFFFAOYSA-N 1-[[2-fluoro-3-(2-oxa-6-azaspiro[3.3]heptan-6-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CC5(COC5)C4)C=CC=3)F)C2=N1 OJFIRFVBSDGLRA-UHFFFAOYSA-N 0.000 claims 1
- WFJVTASXQBMCIJ-UHFFFAOYSA-N 1-[[3-(1,1-dioxo-1,4-thiazinan-4-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCS(=O)(=O)CC3)C2=N1 WFJVTASXQBMCIJ-UHFFFAOYSA-N 0.000 claims 1
- DLEKHBZBTGJFAS-UHFFFAOYSA-N 1-[[3-(3-methoxyazetidin-1-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1C(OC)CN1C1=CC=CC(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1 DLEKHBZBTGJFAS-UHFFFAOYSA-N 0.000 claims 1
- DLTRTXBWIQHSTB-UHFFFAOYSA-N 1-[[3-(4,4-difluoropiperidin-1-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical class C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCC(F)(F)CC3)C2=N1 DLTRTXBWIQHSTB-UHFFFAOYSA-N 0.000 claims 1
- FSMNQKHHJYPTFO-UHFFFAOYSA-N 1-[[3-(4-methoxypiperidin-1-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CC(OC)CCN1C1=CC=CC(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1 FSMNQKHHJYPTFO-UHFFFAOYSA-N 0.000 claims 1
- UEBQTSPICQTRGC-UHFFFAOYSA-N 1-[[3-(4-methylpiperazin-1-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1C1=CC=CC(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1 UEBQTSPICQTRGC-UHFFFAOYSA-N 0.000 claims 1
- AJOWICGTADKWML-OAHLLOKOSA-N 1-[[3-[(3r)-3-methylmorpholin-4-yl]phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C[C@@H]1COCCN1C1=CC=CC(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1 AJOWICGTADKWML-OAHLLOKOSA-N 0.000 claims 1
- AJOWICGTADKWML-HNNXBMFYSA-N 1-[[3-[(3s)-3-methylmorpholin-4-yl]phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C[C@H]1COCCN1C1=CC=CC(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1 AJOWICGTADKWML-HNNXBMFYSA-N 0.000 claims 1
- NKSBPJOOITYGIE-UHFFFAOYSA-N 1-[[3-fluoro-5-(2-oxa-6-azaspiro[3.3]heptan-6-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=C(F)C=3)N3CC4(COC4)C3)C2=N1 NKSBPJOOITYGIE-UHFFFAOYSA-N 0.000 claims 1
- GFQVJTJYTXUIJL-CQSZACIVSA-N 1-[[6-[(3r)-3-methylmorpholin-4-yl]pyridin-2-yl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C[C@@H]1COCCN1C1=CC=CC(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=N1 GFQVJTJYTXUIJL-CQSZACIVSA-N 0.000 claims 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
- KVSYZIDXSXHKCJ-UHFFFAOYSA-N 2-[4-(1h-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2)C2=N1 KVSYZIDXSXHKCJ-UHFFFAOYSA-N 0.000 claims 1
- JKNQFZHGPWIFAG-UHFFFAOYSA-N 2-[4-[[1-[(2,3,6-trifluoro-5-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCOCC4)C=C(F)C=3F)F)C2=N1 JKNQFZHGPWIFAG-UHFFFAOYSA-N 0.000 claims 1
- IDHAVUSUUCAQSL-UHFFFAOYSA-N 2-[4-[[1-[(2,3-difluoro-5-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=C(C=3)N3CCOCC3)F)C2=N1 IDHAVUSUUCAQSL-UHFFFAOYSA-N 0.000 claims 1
- PLMVRZSABYUHTI-UHFFFAOYSA-N 2-[4-[[1-[(2,3-difluoro-5-piperazin-1-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=C(C=3)N3CCNCC3)F)C2=N1 PLMVRZSABYUHTI-UHFFFAOYSA-N 0.000 claims 1
- JCKFUFCNHPKBBX-UHFFFAOYSA-N 2-[4-[[1-[(2,5-difluoro-3-piperazin-1-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCNCC4)C=C(F)C=3)F)C2=N1 JCKFUFCNHPKBBX-UHFFFAOYSA-N 0.000 claims 1
- LBZVZBGLGGAFIE-UHFFFAOYSA-N 2-[4-[[1-[(2,6-difluoro-3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCOCC4)C=CC=3F)F)C2=N1 LBZVZBGLGGAFIE-UHFFFAOYSA-N 0.000 claims 1
- XVEQQWBZJQGFSC-UHFFFAOYSA-N 2-[4-[[1-[(2-fluoro-3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCOCC4)C=CC=3)F)C2=N1 XVEQQWBZJQGFSC-UHFFFAOYSA-N 0.000 claims 1
- ZGAOSRYKXSUHCS-UHFFFAOYSA-N 2-[4-[[1-[(2-fluoro-3-piperazin-1-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCNCC4)C=CC=3)F)C2=N1 ZGAOSRYKXSUHCS-UHFFFAOYSA-N 0.000 claims 1
- AMLWWPHPIOSFIP-UHFFFAOYSA-N 2-[4-[[1-[(2-fluoro-5-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=CC=C(C=3)N3CCOCC3)F)C2=N1 AMLWWPHPIOSFIP-UHFFFAOYSA-N 0.000 claims 1
- IVFMRWYEJNNOSL-UHFFFAOYSA-N 2-[4-[[1-[(3-fluoro-5-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C=C(C=C(F)C=3)N3CCOCC3)C2=N1 IVFMRWYEJNNOSL-UHFFFAOYSA-N 0.000 claims 1
- JRBOTIHEEGZUOK-UHFFFAOYSA-N 2-[4-[[1-[(3-fluoro-5-piperazin-1-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C=C(C=C(F)C=3)N3CCNCC3)C2=N1 JRBOTIHEEGZUOK-UHFFFAOYSA-N 0.000 claims 1
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- KAVSGWIDFBJIDL-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[[3-(oxan-4-yl)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)C3CCOCC3)C2=N1 KAVSGWIDFBJIDL-UHFFFAOYSA-N 0.000 claims 1
- AJYRPZYDWPZPSX-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[[3-(oxetan-3-ylamino)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(NC4COC4)C=CC=3)C2=N1 AJYRPZYDWPZPSX-UHFFFAOYSA-N 0.000 claims 1
- WQIPBIRAHKZDDD-UHFFFAOYSA-N n-(1h-pyrazol-4-yl)-1-[(2,3,6-trifluoro-5-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound FC=1C(CN2C3=NC(NC4=CNN=C4)=NC=C3C=N2)=C(F)C(F)=CC=1N1CCOCC1 WQIPBIRAHKZDDD-UHFFFAOYSA-N 0.000 claims 1
- VGLSHXRZKTWKBX-UHFFFAOYSA-N n-[1-(2,2-difluoroethyl)pyrazol-4-yl]-1-[(3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCOCC3)C2=N1 VGLSHXRZKTWKBX-UHFFFAOYSA-N 0.000 claims 1
- TZKSLWHYQMWGAH-UHFFFAOYSA-N n-[1-(3-aminopropyl)pyrazol-4-yl]-1-[(3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CCCN)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCOCC3)C2=N1 TZKSLWHYQMWGAH-UHFFFAOYSA-N 0.000 claims 1
- KPNNIUGCCUHQCN-UHFFFAOYSA-N n-[1-(pyrrolidin-3-ylmethyl)pyrazol-4-yl]-1-[(2,3,6-trifluoro-5-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound FC=1C(CN2C3=NC(NC4=CN(CC5CNCC5)N=C4)=NC=C3C=N2)=C(F)C(F)=CC=1N1CCOCC1 KPNNIUGCCUHQCN-UHFFFAOYSA-N 0.000 claims 1
- COLAKVWAWPDBMW-UHFFFAOYSA-N n-[1-[3-(dimethylamino)-2-methylpropyl]pyrazol-4-yl]-1-[(3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CC(CN(C)C)C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCOCC3)C2=N1 COLAKVWAWPDBMW-UHFFFAOYSA-N 0.000 claims 1
- YQXJKGGMDCZQLK-UHFFFAOYSA-N n-[1-[3-(dimethylamino)propyl]pyrazol-4-yl]-1-[(2,3,6-trifluoro-5-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CCCN(C)C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCOCC4)C=C(F)C=3F)F)C2=N1 YQXJKGGMDCZQLK-UHFFFAOYSA-N 0.000 claims 1
- NEJZGXMTHYMCPI-UHFFFAOYSA-N n-[1-[3-(dimethylamino)propyl]pyrazol-4-yl]-1-[(2-fluoro-3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CCCN(C)C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCOCC4)C=CC=3)F)C2=N1 NEJZGXMTHYMCPI-UHFFFAOYSA-N 0.000 claims 1
- GYHRXXSXXJCFMH-UHFFFAOYSA-N n-[1-[3-(dimethylamino)propyl]pyrazol-4-yl]-1-[(3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CCCN(C)C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCOCC3)C2=N1 GYHRXXSXXJCFMH-UHFFFAOYSA-N 0.000 claims 1
- KCJAMOQUNKKAOD-UHFFFAOYSA-N n-[1-[[3-(methylaminomethyl)oxetan-3-yl]methyl]pyrazol-4-yl]-1-[(3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(NC=2N=C3N(CC=4C=C(C=CC=4)N4CCOCC4)N=CC3=CN=2)C=NN1CC1(CNC)COC1 KCJAMOQUNKKAOD-UHFFFAOYSA-N 0.000 claims 1
- UVEHOWWEAQITEG-UHFFFAOYSA-N n-[1-[[3-[(dimethylamino)methyl]oxetan-3-yl]methyl]pyrazol-4-yl]-1-[(3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(NC=2N=C3N(CC=4C=C(C=CC=4)N4CCOCC4)N=CC3=CN=2)C=NN1CC1(CN(C)C)COC1 UVEHOWWEAQITEG-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
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| US61/375,358 | 2010-08-20 | ||
| EPPCT/EP2010/065700 | 2010-10-19 | ||
| PCT/EP2010/065700 WO2011048082A1 (en) | 2009-10-20 | 2010-10-19 | Heterocyclyl pyrazolopyrimidine analogues as jak inhibitors |
| US201161476398P | 2011-04-18 | 2011-04-18 | |
| US61/476,398 | 2011-04-18 | ||
| PCT/EP2011/063905 WO2012022681A2 (en) | 2010-08-20 | 2011-08-12 | Heterocyclyl pyrazolopyrimidine analogues as selective jak inhibitors |
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| KR20140063700A (ko) | 2011-09-20 | 2014-05-27 | 셀좀 리미티드 | 키나제 억제제로서의 피라졸로[4,3-c]피리딘 유도체 |
| EP2794598A1 (en) | 2011-12-23 | 2014-10-29 | Cellzome Limited | Pyrimidine-2,4-diamine derivatives as kinase inhibitors |
| WO2014090700A1 (en) | 2012-12-14 | 2014-06-19 | Basf Se | Malononitrile compounds for controlling animal pests |
| AR099134A1 (es) * | 2014-01-24 | 2016-06-29 | Hoffmann La Roche | Procedimiento para la preparación de n-[(3-aminooxetán-3-il)metil]-2-(1,1-dioxo-3,5-dihidro-1,4-benzotiazepín-4-il)-6-metil-quinazolín-4-amina |
| CA2945766C (en) | 2014-04-17 | 2023-09-26 | Merial, Inc. | Use of malononitrile compounds for protecting animals from parasites |
| NO2721710T3 (enExample) | 2014-08-21 | 2018-03-31 | ||
| KR102566924B1 (ko) * | 2016-07-29 | 2023-08-11 | 랩트 테라퓨틱스, 인크. | 케모카인 수용체 조절제 및 이의 용도 |
| CN110885331B (zh) * | 2018-09-11 | 2021-07-09 | 中国药科大学 | 一种6-氨基-1H-吡唑并[3，4-d]嘧啶类JAK激酶抑制剂的制备与应用 |
| WO2020092015A1 (en) | 2018-11-02 | 2020-05-07 | University Of Rochester | Therapeutic mitigation of epithelial infection |
| JP7696834B2 (ja) * | 2019-05-27 | 2025-06-23 | ディザル（ジァンスー）ファーマシューティカル・カンパニー・リミテッド | Ｄｎａ依存性タンパク質キナーゼ阻害剤 |
| KR20240162125A (ko) * | 2022-03-17 | 2024-11-14 | 화이자 인코포레이티드 | 한선염 치료를 위한 방법, 투여 레지멘, 및 조성물 |
| WO2025235331A1 (en) * | 2024-05-07 | 2025-11-13 | Nikang Therapeutics, Inc. | Bifunctional compounds containing pyrazolopyrimidine derivatives for degrading certain cyclin-dependent kinase via ubiquitin proteasome pathway |
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| DE69837529T2 (de) | 1997-02-12 | 2007-07-26 | Electrophoretics Ltd., Cobham | Proteinmarker für lungenkrebs und deren verwendung |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| SK288365B6 (sk) | 1999-02-10 | 2016-07-01 | Astrazeneca Ab | Medziprodukty pre chinazolínové deriváty ako inhibítory angiogenézy |
| IL149034A0 (en) | 1999-11-05 | 2002-11-10 | Astrazeneca Ab | Quinazoline derivatives as vegf inhibitors |
| GEP20053479B (en) | 1999-12-10 | 2005-03-25 | Pfizer Prod Inc | Pyrrolo[2,3-d]Pyrimidine Compounds, Pharmaceutical Composition Containing the Same and Use |
| RS50444B (sr) | 2000-02-15 | 2010-03-02 | Sugen Inc. | Inhibitori 2-indolinon protein kinaze supstituisani pirolom |
| ES2411975T3 (es) | 2005-01-14 | 2013-07-09 | Janssen Pharmaceutica Nv | Pirimidinas heterocíclicas anilladas de 5 miembros como inhibidores de cinasas |
| PL1891446T3 (pl) | 2005-06-14 | 2013-08-30 | Cellzome Gmbh | Sposób identyfikacji nowych związków oddziałujących z enzymami |
| GB0605691D0 (en) | 2006-03-21 | 2006-05-03 | Novartis Ag | Organic Compounds |
| DE602006004196D1 (de) | 2006-06-01 | 2009-01-22 | Cellzome Ag | Verfahren zur Identifizierung von mit ZAP-70 wechselwirkenden Molekülen und zur ZAP-70-Reinigung |
| WO2008009458A1 (en) | 2006-07-21 | 2008-01-24 | Novartis Ag | 2, 4 -di (arylaminio) -pyrimidine-5-carboxamide compounds as jak kinases inhibitors |
| CA2669686A1 (en) | 2006-11-16 | 2008-05-22 | Pharmacopeia, Llc | 7-substituted purine derivatives for immunosuppression |
| JP2010532312A (ja) | 2007-01-30 | 2010-10-07 | バイオジェン・アイデック・エムエイ・インコーポレイテッド | １−ｈ−ピラゾロ（３，４ｂ）ピリミジン誘導体および有糸分裂キナーゼの調節剤としてのその使用 |
| WO2008118822A1 (en) | 2007-03-23 | 2008-10-02 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| WO2008118823A2 (en) | 2007-03-26 | 2008-10-02 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| JP2010532756A (ja) | 2007-07-06 | 2010-10-14 | オーエスアイ・ファーマスーティカルズ・インコーポレーテッド | ｍＴＯＲＣ１及びｍＴＯＲＣ２の両方の阻害剤を含む組み合わせ抗癌療法 |
| AU2009211338B2 (en) | 2008-02-06 | 2011-12-15 | Novartis Ag | Pyrrolo[2, 3-D] pyrimidines and use thereof as tyrosine kinase inhibitors |
| CL2009001884A1 (es) | 2008-10-02 | 2010-05-14 | Incyte Holdings Corp | Uso de 3-ciclopentil-3-[4-(7h-pirrolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il)propanonitrilo, inhibidor de janus quinasa, y uso de una composición que lo comprende para el tratamiento del ojo seco. |
| US20120040955A1 (en) | 2009-04-14 | 2012-02-16 | Richard John Harrison | Fluoro substituted pyrimidine compounds as jak3 inhibitors |
| CN102666545B (zh) * | 2009-10-20 | 2016-04-06 | 塞尔卓姆有限公司 | 作为jak抑制剂的杂环吡唑并嘧啶类似物 |
| WO2011156698A2 (en) | 2010-06-11 | 2011-12-15 | Abbott Laboratories | NOVEL PYRAZOLO[3,4-d]PYRIMIDINE COMPOUNDS |
-
2011
- 2011-08-12 JP JP2013524421A patent/JP2013534233A/ja active Pending
- 2011-08-12 US US13/816,555 patent/US9040545B2/en not_active Expired - Fee Related
- 2011-08-12 WO PCT/EP2011/063905 patent/WO2012022681A2/en not_active Ceased
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