CA2775009A1 - Heterocyclyl pyrazolopyrimidine analogues as jak inhibitors - Google Patents

Info

Publication number

CA2775009A1

CA2775009A1 CA2775009A CA2775009A CA2775009A1 CA 2775009 A1 CA2775009 A1 CA 2775009A1 CA 2775009 A CA2775009 A CA 2775009A CA 2775009 A CA2775009 A CA 2775009A CA 2775009 A1 CA2775009 A1 CA 2775009A1

Authority

CA

Canada

Prior art keywords

pyrimidin

pyrazolo

pyrazol

methyl

amine

Prior art date

2009-10-20

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• -1 Heterocyclyl pyrazolopyrimidine analogues Chemical class 0.000 title claims description 52
• 229940122245 Janus kinase inhibitor Drugs 0.000 title abstract description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 434
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 58
• 201000010099 disease Diseases 0.000 claims abstract description 32
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• 239000003814 drug Substances 0.000 claims abstract description 16
• 238000002360 preparation method Methods 0.000 claims abstract description 15
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 11
• 230000001363 autoimmune Effects 0.000 claims abstract description 10
• 230000000172 allergic effect Effects 0.000 claims abstract description 9
• 208000010668 atopic eczema Diseases 0.000 claims abstract description 9
• 230000001900 immune effect Effects 0.000 claims abstract description 8
• 238000000034 method Methods 0.000 claims description 796
• 229910052757 nitrogen Inorganic materials 0.000 claims description 56
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 125000000217 alkyl group Chemical group 0.000 claims description 40
• 229910052736 halogen Inorganic materials 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 36
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 31
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
• 208000035475 disorder Diseases 0.000 claims description 25
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 21
• 125000005843 halogen group Chemical group 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 11
• HEIVCVWMBXZRAV-UHFFFAOYSA-N 1-[(6-fluoropyridin-2-yl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3N=C(F)C=CC=3)C2=N1 HEIVCVWMBXZRAV-UHFFFAOYSA-N 0.000 claims description 11
• 206010052779 Transplant rejections Diseases 0.000 claims description 11
• 208000024908 graft versus host disease Diseases 0.000 claims description 10
• 230000002062 proliferating effect Effects 0.000 claims description 9
• 208000009329 Graft vs Host Disease Diseases 0.000 claims description 8
• 208000037765 diseases and disorders Diseases 0.000 claims description 8
• 239000002207 metabolite Substances 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 7
• 229940002612 prodrug Drugs 0.000 claims description 7
• 239000000651 prodrug Substances 0.000 claims description 7
• YMEBXDCVFTWQHO-UHFFFAOYSA-N 2-[[6-[[1-(2,2-difluoroethyl)-3-methoxypyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]benzonitrile Chemical compound COC1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)C#N)C2=N1 YMEBXDCVFTWQHO-UHFFFAOYSA-N 0.000 claims description 6
• HJPQPBVERHKOEK-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-(1h-pyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound FC1=CC=CC=C1CN1C2=NC(NC3=CNN=C3)=NC=C2C=N1 HJPQPBVERHKOEK-UHFFFAOYSA-N 0.000 claims description 5
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
• QSOMITBKRDDBRN-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[[3-(2-phenylmethoxyethoxy)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(OCCOCC=4C=CC=CC=4)C=CC=3)C2=N1 QSOMITBKRDDBRN-UHFFFAOYSA-N 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• HHVZSFJMJRDWDV-UHFFFAOYSA-N 1-[[6-(dimethylamino)pyridin-2-yl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CN(C)C1=CC=CC(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=N1 HHVZSFJMJRDWDV-UHFFFAOYSA-N 0.000 claims description 4
• VOXQMCLJZAQDQY-UHFFFAOYSA-N 2-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]benzonitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)C#N)C2=N1 VOXQMCLJZAQDQY-UHFFFAOYSA-N 0.000 claims description 4
• YGSYSJLESKRDLZ-UHFFFAOYSA-N 2-[[6-[[1-(2,2-difluoroethyl)-3-methylpyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]benzonitrile Chemical compound CC1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)C#N)C2=N1 YGSYSJLESKRDLZ-UHFFFAOYSA-N 0.000 claims description 4
• RFBYLLXZGGAXCX-UHFFFAOYSA-N 2-[[6-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]benzonitrile Chemical compound C1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)C#N)C2=N1 RFBYLLXZGGAXCX-UHFFFAOYSA-N 0.000 claims description 4
• ZVLOCMSXMRKPDV-UHFFFAOYSA-N 4-[3-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]morpholin-3-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3C(COCC3)=O)C2=N1 ZVLOCMSXMRKPDV-UHFFFAOYSA-N 0.000 claims description 4
• FYQJTNKRGLUVOP-UHFFFAOYSA-N 4-fluoro-2-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]benzonitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=CC=C(F)C=3)C#N)C2=N1 FYQJTNKRGLUVOP-UHFFFAOYSA-N 0.000 claims description 4
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
• OLRZAVSGERDOMH-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[(6-pyrrolidin-1-ylpyridin-2-yl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3N=C(C=CC=3)N3CCCC3)C2=N1 OLRZAVSGERDOMH-UHFFFAOYSA-N 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• XBKRKCDHJDJSGK-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(N2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)C=C1 XBKRKCDHJDJSGK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• XXIQVBZNPUMPBA-UHFFFAOYSA-N 1-(1,3-benzodioxol-4-ylmethyl)-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=4OCOC=4C=CC=3)C2=N1 XXIQVBZNPUMPBA-UHFFFAOYSA-N 0.000 claims description 3
• GFHDNMWKKHJZGY-UHFFFAOYSA-N 1-(4-fluorophenyl)-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2C=3C=CC(F)=CC=3)C2=N1 GFHDNMWKKHJZGY-UHFFFAOYSA-N 0.000 claims description 3
• UHWRBLQOXIZSLR-UHFFFAOYSA-N 1-[(2,3-dichlorophenyl)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(Cl)C=CC=3)Cl)C2=N1 UHWRBLQOXIZSLR-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• RZIROYUNYFJDJG-UHFFFAOYSA-N 1-[(2,3-difluorophenyl)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=CC=3)F)C2=N1 RZIROYUNYFJDJG-UHFFFAOYSA-N 0.000 claims description 3
• SKQLTRLCWZIFNB-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)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(F)=CC=3)F)C2=N1 SKQLTRLCWZIFNB-UHFFFAOYSA-N 0.000 claims description 3
• WDUUIFSPJHGKQN-UHFFFAOYSA-N 1-[(2,5-difluorophenyl)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(F)C=3)F)C2=N1 WDUUIFSPJHGKQN-UHFFFAOYSA-N 0.000 claims description 3
• ZVLCXXBFWOZXOO-UHFFFAOYSA-N 1-[(2,6-difluoro-3-methoxyphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=C(F)C(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1F ZVLCXXBFWOZXOO-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• RMOBSPFBPRWCKO-UHFFFAOYSA-N 1-[(2,6-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=CC=3F)F)C2=N1 RMOBSPFBPRWCKO-UHFFFAOYSA-N 0.000 claims description 3
• CEZUMORXQYJTSP-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)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=CC=3F)F)C2=N1 CEZUMORXQYJTSP-UHFFFAOYSA-N 0.000 claims description 3
• COABYLDTTHSBRS-UHFFFAOYSA-N 1-[(2-chloro-5-fluorophenyl)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(F)C=3)Cl)C2=N1 COABYLDTTHSBRS-UHFFFAOYSA-N 0.000 claims description 3
• CVORKSUGVHKCPA-UHFFFAOYSA-N 1-[(2-chlorophenyl)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=CC=3)Cl)C2=N1 CVORKSUGVHKCPA-UHFFFAOYSA-N 0.000 claims description 3
• MNFWUOFSLZNBHP-UHFFFAOYSA-N 1-[(2-cyclopropylphenyl)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=CC=3)C3CC3)C2=N1 MNFWUOFSLZNBHP-UHFFFAOYSA-N 0.000 claims description 3
• IXLNNXMEJQIXGJ-UHFFFAOYSA-N 1-[(2-cyclopropylphenyl)methyl]-n-[1-(2,2-difluoroethyl)pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)C3CC3)C2=N1 IXLNNXMEJQIXGJ-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• LRUMFTYLJVBLKH-UHFFFAOYSA-N 1-[(2-fluoro-6-methoxyphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(F)=C1CN1C2=NC(NC3=CN(C)N=C3)=NC=C2C=N1 LRUMFTYLJVBLKH-UHFFFAOYSA-N 0.000 claims description 3
• ZCLRRECCKIYBIN-UHFFFAOYSA-N 1-[(2-fluorophenyl)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=CC=3)F)C2=N1 ZCLRRECCKIYBIN-UHFFFAOYSA-N 0.000 claims description 3
• UWFUJZMWQAJCLL-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-(1-methylpyrrol-3-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CN1C=CC(NC=2N=C3N(CC=4C(=CC=CC=4)F)N=CC3=CN=2)=C1 UWFUJZMWQAJCLL-UHFFFAOYSA-N 0.000 claims description 3
• DNJMPYFDOXMCSX-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-[1-(2-methoxyethyl)pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CCOC)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)F)C2=N1 DNJMPYFDOXMCSX-UHFFFAOYSA-N 0.000 claims description 3
• WLSDYLMXXCWELY-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-[1-(2-piperazin-1-ylethyl)pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound FC1=CC=CC=C1CN1C2=NC(NC3=CN(CCN4CCNCC4)N=C3)=NC=C2C=N1 WLSDYLMXXCWELY-UHFFFAOYSA-N 0.000 claims description 3
• DUFWFVFZGJCLJX-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-[1-(3-morpholin-4-ylpropyl)pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound FC1=CC=CC=C1CN1C2=NC(NC3=CN(CCCN4CCOCC4)N=C3)=NC=C2C=N1 DUFWFVFZGJCLJX-UHFFFAOYSA-N 0.000 claims description 3
• SJMLJBPWRXWUQZ-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-[1-(3-piperidin-1-ylpropyl)pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound FC1=CC=CC=C1CN1C2=NC(NC3=CN(CCCN4CCCCC4)N=C3)=NC=C2C=N1 SJMLJBPWRXWUQZ-UHFFFAOYSA-N 0.000 claims description 3
• SVGLAYRRIPRLNQ-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-[1-(pyrrolidin-3-ylmethyl)pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound FC1=CC=CC=C1CN1C2=NC(NC3=CN(CC4CNCC4)N=C3)=NC=C2C=N1 SVGLAYRRIPRLNQ-UHFFFAOYSA-N 0.000 claims description 3
• QOIQBAKUMCFKOQ-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-[1-[(1-methylpiperidin-3-yl)methyl]pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1N(C)CCCC1CN1N=CC(NC=2N=C3N(CC=4C(=CC=CC=4)F)N=CC3=CN=2)=C1 QOIQBAKUMCFKOQ-UHFFFAOYSA-N 0.000 claims description 3
• PQZRTWLBTUHACA-UHFFFAOYSA-N 1-[(2-fluoropyridin-3-yl)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(=NC=CC=3)F)C2=N1 PQZRTWLBTUHACA-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• XNZDWLQVGXRWDN-UHFFFAOYSA-N 1-[(3,4-difluorophenyl)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(F)=CC=3)C2=N1 XNZDWLQVGXRWDN-UHFFFAOYSA-N 0.000 claims description 3
• JEGLHBQCOJSBQZ-UHFFFAOYSA-N 1-[(3,5-difluorophenyl)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(F)C=3)C2=N1 JEGLHBQCOJSBQZ-UHFFFAOYSA-N 0.000 claims description 3
• WNJGXIPMJRBQCP-UHFFFAOYSA-N 1-[(3-chloro-2-fluorophenyl)methyl]-n-[1-(2,2-difluoroethyl)pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C(=C(Cl)C=CC=3)F)C2=N1 WNJGXIPMJRBQCP-UHFFFAOYSA-N 0.000 claims description 3
• USRQJXBCMFVJLO-UHFFFAOYSA-N 1-[(3-chlorophenyl)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(Cl)C=CC=3)C2=N1 USRQJXBCMFVJLO-UHFFFAOYSA-N 0.000 claims description 3
• DFUWGPDGLBMTPD-UHFFFAOYSA-N 1-[(3-fluoro-2-methylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC1=C(F)C=CC=C1CN1C2=NC(NC3=CN(C)N=C3)=NC=C2C=N1 DFUWGPDGLBMTPD-UHFFFAOYSA-N 0.000 claims description 3
• UTKOWHMLLNSPAA-UHFFFAOYSA-N 1-[(3-fluoro-5-methoxyphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC(F)=CC(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1 UTKOWHMLLNSPAA-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• OGUOSEOWQARWFF-UHFFFAOYSA-N 1-[(3-fluorophenyl)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=CC=3)C2=N1 OGUOSEOWQARWFF-UHFFFAOYSA-N 0.000 claims description 3
• INWANPFEKCGKIV-UHFFFAOYSA-N 1-[(3-fluoropyridin-4-yl)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(=CN=CC=3)F)C2=N1 INWANPFEKCGKIV-UHFFFAOYSA-N 0.000 claims description 3
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• SHMQFHKRXQJXAE-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[[3-(2-piperidin-1-ylethoxy)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(OCCN4CCCCC4)C=CC=3)C2=N1 SHMQFHKRXQJXAE-UHFFFAOYSA-N 0.000 claims description 3
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• CYBBOLZJBFPVHJ-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[[3-(trifluoromethoxy)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(OC(F)(F)F)C=CC=3)C2=N1 CYBBOLZJBFPVHJ-UHFFFAOYSA-N 0.000 claims description 3
• KPAPXMDHYXMKED-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[[3-(trifluoromethyl)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)C(F)(F)F)C2=N1 KPAPXMDHYXMKED-UHFFFAOYSA-N 0.000 claims description 3
• SYMDUSZIPSVNBI-QGZVFWFLSA-N n-(1-methylpyrazol-4-yl)-1-[[6-[[(2r)-oxolan-2-yl]methoxy]pyridin-2-yl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3N=C(OC[C@@H]4OCCC4)C=CC=3)C2=N1 SYMDUSZIPSVNBI-QGZVFWFLSA-N 0.000 claims description 3
• BSTPTJKYNPKRAU-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-phenylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2C=3C=CC=CC=3)C2=N1 BSTPTJKYNPKRAU-UHFFFAOYSA-N 0.000 claims description 3
• BIPWDPXETWAQTE-UHFFFAOYSA-N n-(cyanomethyl)-4-[[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-1-methylpyrrole-2-carboxamide Chemical compound C1=C(C(=O)NCC#N)N(C)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)F)C2=N1 BIPWDPXETWAQTE-UHFFFAOYSA-N 0.000 claims description 3
• GEKZAYQRLFLPDB-UHFFFAOYSA-N n-[1-(2,2-difluoroethyl)pyrazol-4-yl]-1-[(2,3,6-trifluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=CC=3F)F)C2=N1 GEKZAYQRLFLPDB-UHFFFAOYSA-N 0.000 claims description 3
• PYSLNYOXKZSHON-UHFFFAOYSA-N n-[1-(2,2-difluoroethyl)pyrazol-4-yl]-1-[(2,3-difluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=CC=3)F)C2=N1 PYSLNYOXKZSHON-UHFFFAOYSA-N 0.000 claims description 3
• JAQUZWDORWDABY-UHFFFAOYSA-N n-[1-(2,2-difluoroethyl)pyrazol-4-yl]-1-[(2,5-difluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C(=CC=C(F)C=3)F)C2=N1 JAQUZWDORWDABY-UHFFFAOYSA-N 0.000 claims description 3
• QXIJILYBISXABQ-UHFFFAOYSA-N n-[1-(2,2-difluoroethyl)pyrazol-4-yl]-1-[(2,6-difluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3F)F)C2=N1 QXIJILYBISXABQ-UHFFFAOYSA-N 0.000 claims description 3
• KZMXYHIYYCKDCI-UHFFFAOYSA-N n-[1-(2,2-difluoroethyl)pyrazol-4-yl]-1-[(3-fluoro-2-methylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC1=C(F)C=CC=C1CN1C2=NC(NC3=CN(CC(F)F)N=C3)=NC=C2C=N1 KZMXYHIYYCKDCI-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
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• 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 description 3
• UMKDUKWOLQDTDV-UHFFFAOYSA-N n-[1-[3-(azetidin-1-yl)propyl]pyrazol-4-yl]-1-[(2-fluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound FC1=CC=CC=C1CN1C2=NC(NC3=CN(CCCN4CCC4)N=C3)=NC=C2C=N1 UMKDUKWOLQDTDV-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
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• GQDGDVHYEFKTGI-UHFFFAOYSA-N n-[2-[[6-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]methanesulfonamide;hydrochloride Chemical compound Cl.CS(=O)(=O)NC1=CC=CC=C1CN1C2=NC(NC3=CN(CC(F)F)N=C3)=NC=C2C=N1 GQDGDVHYEFKTGI-UHFFFAOYSA-N 0.000 claims description 3
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• XCUMJBFRPJWHRK-UHFFFAOYSA-N n-[4-[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]phenyl]methanesulfonamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2C=3C=CC(NS(C)(=O)=O)=CC=3)C2=N1 XCUMJBFRPJWHRK-UHFFFAOYSA-N 0.000 claims description 3
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• NCSVOWDBQPUXPA-MRXNPFEDSA-N (3r)-1-[6-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyridin-2-yl]pyrrolidin-3-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3N=C(C=CC=3)N3C[C@H](O)CC3)C2=N1 NCSVOWDBQPUXPA-MRXNPFEDSA-N 0.000 claims description 2
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• 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 description 2
• SBOFFGLMMDITKV-UHFFFAOYSA-N 1-[(2-fluoro-5-methoxyphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=C(F)C(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1 SBOFFGLMMDITKV-UHFFFAOYSA-N 0.000 claims description 2
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• KRCVCAAEEUUKAZ-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-(1-methylsulfonylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(S(=O)(=O)C)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)F)C2=N1 KRCVCAAEEUUKAZ-UHFFFAOYSA-N 0.000 claims description 2
• FGJAYBFBYDTYKZ-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound FC1=CC=CC=C1CN1C2=NC(NC3=CN(CCN4CCOCC4)N=C3)=NC=C2C=N1 FGJAYBFBYDTYKZ-UHFFFAOYSA-N 0.000 claims description 2
• SVXWXDVDKDRQKU-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-[1-(2-piperidin-1-ylethyl)pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound FC1=CC=CC=C1CN1C2=NC(NC3=CN(CCN4CCCCC4)N=C3)=NC=C2C=N1 SVXWXDVDKDRQKU-UHFFFAOYSA-N 0.000 claims description 2
• RAQMFONITHRGNT-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-[1-[2-(oxan-4-yl)ethyl]pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound FC1=CC=CC=C1CN1C2=NC(NC3=CN(CCC4CCOCC4)N=C3)=NC=C2C=N1 RAQMFONITHRGNT-UHFFFAOYSA-N 0.000 claims description 2
• CHABDJAITHXTQJ-UHFFFAOYSA-N 1-[(2-methoxyphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC=C1CN1C2=NC(NC3=CN(C)N=C3)=NC=C2C=N1 CHABDJAITHXTQJ-UHFFFAOYSA-N 0.000 claims description 2
• NNJADFFWIMOAQR-UHFFFAOYSA-N 1-[(2-methylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC1=CC=CC=C1CN1C2=NC(NC3=CN(C)N=C3)=NC=C2C=N1 NNJADFFWIMOAQR-UHFFFAOYSA-N 0.000 claims description 2
• QJLFMMRBKDUBJM-UHFFFAOYSA-N 1-[(3-chloro-2-fluorophenyl)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(Cl)C=CC=3)F)C2=N1 QJLFMMRBKDUBJM-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• VUJCXYALOQLIJP-UHFFFAOYSA-N 1-[(4-fluorophenyl)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(F)=CC=3)C2=N1 VUJCXYALOQLIJP-UHFFFAOYSA-N 0.000 claims description 2
• XBJDOUHTQQJLBD-UHFFFAOYSA-N 1-[2,4-difluoro-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=3F)F)C2=N1 XBJDOUHTQQJLBD-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
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