JP5744887B2 - Ｊａｋ阻害剤としてのヘテロシクリルピラゾロピリミジン類似体 - Google Patents

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Publication number

JP5744887B2

JP5744887B2 JP2012534661A JP2012534661A JP5744887B2 JP 5744887 B2 JP5744887 B2 JP 5744887B2 JP 2012534661 A JP2012534661 A JP 2012534661A JP 2012534661 A JP2012534661 A JP 2012534661A JP 5744887 B2 JP5744887 B2 JP 5744887B2

Authority

JP

Japan

Prior art keywords

pyrazolo

pyrazol

methyl

pyrimidin

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.)

Expired - Fee Related

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• 229940122245 Janus kinase inhibitor Drugs 0.000 title description 6
• 238000000034 method Methods 0.000 claims description 914
• 150000001875 compounds Chemical class 0.000 claims description 426
• -1 2-Methyl-6- (6- (1-methyl-1H-pyrazol-4-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) pyridin-3-yl Chemical group 0.000 claims description 117
• 125000000217 alkyl group Chemical group 0.000 claims description 68
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 53
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 51
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 50
• 229910052739 hydrogen Inorganic materials 0.000 claims description 46
• 229910052736 halogen Inorganic materials 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 31
• 201000010099 disease Diseases 0.000 claims description 30
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 28
• 150000002367 halogens Chemical class 0.000 claims description 28
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 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 25
• 208000035475 disorder Diseases 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 229920006395 saturated elastomer Polymers 0.000 claims description 19
• 238000002360 preparation method Methods 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 10
• 206010052779 Transplant rejections Diseases 0.000 claims description 10
• 208000024908 graft versus host disease Diseases 0.000 claims description 10
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
• 230000002062 proliferating effect Effects 0.000 claims description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
• 208000009329 Graft vs Host Disease Diseases 0.000 claims description 8
• 230000000172 allergic effect Effects 0.000 claims description 8
• 208000010668 atopic eczema Diseases 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 230000002757 inflammatory effect Effects 0.000 claims description 8
• 230000001363 autoimmune Effects 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 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
• 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 5
• 150000001408 amides Chemical class 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 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 4
• 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 4
• JELZSNWECCAMNA-UHFFFAOYSA-N 1-[[3-(3,6-dihydro-2h-pyran-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)C=3CCOCC=3)C2=N1 JELZSNWECCAMNA-UHFFFAOYSA-N 0.000 claims description 4
• LPPSHLCFHHTQSE-UHFFFAOYSA-N 1-[[3-(3-methoxypropoxy)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COCCCOC1=CC=CC(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1 LPPSHLCFHHTQSE-UHFFFAOYSA-N 0.000 claims description 4
• 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
• YYIUEANMEUVYNM-UHFFFAOYSA-N 1-benzyl-n-(3-methoxy-1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=CC=CC=3)C2=N1 YYIUEANMEUVYNM-UHFFFAOYSA-N 0.000 claims description 4
• JLWBKUBNZDINRB-UHFFFAOYSA-N 2-[4-[[1-[(2,3,6-trifluoro-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(N4CCNCC4)C=C(F)C=3F)F)C2=N1 JLWBKUBNZDINRB-UHFFFAOYSA-N 0.000 claims description 4
• XHCZLCRTAUWVDD-UHFFFAOYSA-N 2-[[6-[(1-methylpyrazol-3-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]benzonitrile Chemical compound CN1C=CC(NC=2N=C3N(CC=4C(=CC=CC=4)C#N)N=CC3=CN=2)=N1 XHCZLCRTAUWVDD-UHFFFAOYSA-N 0.000 claims description 4
• ABCZIYMWXKHIAS-UHFFFAOYSA-N 2-[[6-[[1-(2,2-difluoroethyl)-3-methylpyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-4-fluorobenzonitrile Chemical compound CC1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C(=CC=C(F)C=3)C#N)C2=N1 ABCZIYMWXKHIAS-UHFFFAOYSA-N 0.000 claims description 4
• AJQHWAKMGMTSIQ-UHFFFAOYSA-N [2-fluoro-3-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(C(=O)N4CCOCC4)C=CC=3)F)C2=N1 AJQHWAKMGMTSIQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• PCDZPLMEOPDZBY-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-(naphthalen-1-ylmethyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C4=CC=CC=C4C=CC=3)C2=N1 PCDZPLMEOPDZBY-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 229940124530 sulfonamide Drugs 0.000 claims description 4
• 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 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
• JKTDAINXXNUXHW-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-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=4OCCOC=4C=CC=3)C2=N1 JKTDAINXXNUXHW-UHFFFAOYSA-N 0.000 claims description 3
• DQSXUBXEOGJPCF-UHFFFAOYSA-N 1-(4-chlorophenyl)-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(Cl)=CC=3)C2=N1 DQSXUBXEOGJPCF-UHFFFAOYSA-N 0.000 claims description 3
• JIBRGSZIIOAWNA-UHFFFAOYSA-N 1-(4-fluoro-3-methoxyphenyl)-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(F)C(OC)=CC(N2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1 JIBRGSZIIOAWNA-UHFFFAOYSA-N 0.000 claims description 3
• SUOAPTONOWESTO-UHFFFAOYSA-N 1-(4-fluoro-3-methylphenyl)-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(F)C(C)=CC(N2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1 SUOAPTONOWESTO-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
• 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 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
• TVXPMVCKSARWTR-UHFFFAOYSA-N 1-[(2-chloro-6-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=3F)Cl)C2=N1 TVXPMVCKSARWTR-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
• GPMFZDIWXIVQJL-UHFFFAOYSA-N 1-[(2-fluoro-3-methoxyphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1F GPMFZDIWXIVQJL-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
• 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 3
• 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 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
• QYCFHVPLTINOLE-UHFFFAOYSA-N 1-[(2-fluoro-6-methylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC1=CC=CC(F)=C1CN1C2=NC(NC3=CN(C)N=C3)=NC=C2C=N1 QYCFHVPLTINOLE-UHFFFAOYSA-N 0.000 claims description 3
• BQJXSFQGGXKCKI-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-(1-methylimidazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CN1C=NC(NC=2N=C3N(CC=4C(=CC=CC=4)F)N=CC3=CN=2)=C1 BQJXSFQGGXKCKI-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
• 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 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
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• ZEEJVWLLTGRRJV-UHFFFAOYSA-N 1-benzyl-n-[1-(2,2-difluoroethyl)-3-methoxypyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C=CC=CC=3)C2=N1 ZEEJVWLLTGRRJV-UHFFFAOYSA-N 0.000 claims description 3
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• FYAWLYOARMAJNB-UHFFFAOYSA-N 2-[4-[[1-[(2,5-difluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-3-methoxypyrazol-1-yl]ethanol Chemical compound COC1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=CC=C(F)C=3)F)C2=N1 FYAWLYOARMAJNB-UHFFFAOYSA-N 0.000 claims description 3
• GQBKWJDVSDVRNO-UHFFFAOYSA-N 2-[4-[[1-[(2,5-difluorophenyl)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(F)C=3)F)C2=N1 GQBKWJDVSDVRNO-UHFFFAOYSA-N 0.000 claims description 3
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• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
• QKYBMXRWTCELMS-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-(4-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 QKYBMXRWTCELMS-UHFFFAOYSA-N 0.000 claims description 3
• CIEQLXAFLJNZJD-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[(2,3,5-trifluorophenyl)methyl]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)F)C2=N1 CIEQLXAFLJNZJD-UHFFFAOYSA-N 0.000 claims description 3
• DIUJLEHOODQLHY-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[(2,3,6-trifluoro-5-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCOCC4)C=C(F)C=3F)F)C2=N1 DIUJLEHOODQLHY-UHFFFAOYSA-N 0.000 claims description 3
• JWGDKIZETGKOOA-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[(2,3,6-trifluoro-5-piperazin-1-ylphenyl)methyl]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=3F)F)C2=N1 JWGDKIZETGKOOA-UHFFFAOYSA-N 0.000 claims description 3
• FMVOYADWIRIGMC-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[(2,3,6-trifluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=CC=3F)F)C2=N1 FMVOYADWIRIGMC-UHFFFAOYSA-N 0.000 claims description 3
• NAYRVUMCMCDDCA-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[(2-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)N3CCOCC3)C2=N1 NAYRVUMCMCDDCA-UHFFFAOYSA-N 0.000 claims description 3
• IFCVSVOJHCSZOG-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[(2-phenoxyphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)OC=3C=CC=CC=3)C2=N1 IFCVSVOJHCSZOG-UHFFFAOYSA-N 0.000 claims description 3
• YUSLHRSYCJUEEE-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[(2-phenylmethoxyphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)OCC=3C=CC=CC=3)C2=N1 YUSLHRSYCJUEEE-UHFFFAOYSA-N 0.000 claims description 3
• KEBMGXNHOKLUOL-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[(2-propan-2-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC(C)C1=CC=CC=C1CN1C2=NC(NC3=CN(C)N=C3)=NC=C2C=N1 KEBMGXNHOKLUOL-UHFFFAOYSA-N 0.000 claims description 3
• NNRNNWAFTKYION-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[(3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCOCC3)C2=N1 NNRNNWAFTKYION-UHFFFAOYSA-N 0.000 claims description 3
• QZWIWFGLEPZWCL-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[(3-piperazin-1-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCNCC3)C2=N1 QZWIWFGLEPZWCL-UHFFFAOYSA-N 0.000 claims description 3
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• UUVCPFMSHZOVOK-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[(6-morpholin-4-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)N3CCOCC3)C2=N1 UUVCPFMSHZOVOK-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• JKUUWRXNSJRHOQ-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[[2-(2-phenylmethoxyethoxy)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)OCCOCC=3C=CC=CC=3)C2=N1 JKUUWRXNSJRHOQ-UHFFFAOYSA-N 0.000 claims description 3
• ZEWHPAPVBMGHKM-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[[2-(trifluoromethoxy)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)OC(F)(F)F)C2=N1 ZEWHPAPVBMGHKM-UHFFFAOYSA-N 0.000 claims description 3
• WLFMMCNMFHIPCH-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[[3-(2-oxa-5-azabicyclo[2.2.2]octan-5-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)N3C4CCC(OC4)C3)C2=N1 WLFMMCNMFHIPCH-UHFFFAOYSA-N 0.000 claims description 3
• SHMQFHKRXQJXAE-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[[3-(2-piperidin-1-ylethoxy)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical class 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
• OSELICAWOINZKR-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[[3-(morpholin-4-ylmethyl)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(CN4CCOCC4)C=CC=3)C2=N1 OSELICAWOINZKR-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• NWNWNYQPYWUPRK-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[[3-(oxolan-3-yloxy)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(OC4COCC4)C=CC=3)C2=N1 NWNWNYQPYWUPRK-UHFFFAOYSA-N 0.000 claims description 3
• 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
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• BYDYHOZZXABWJN-OAHLLOKOSA-N n-(1-methylpyrazol-4-yl)-1-[[6-[[(3r)-oxolan-3-yl]amino]pyridin-2-yl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3N=C(N[C@H]4COCC4)C=CC=3)C2=N1 BYDYHOZZXABWJN-OAHLLOKOSA-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
• 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 description 3
• KIWSWKLNGSBSTL-UHFFFAOYSA-N n-(5-chloro-1h-pyrazol-4-yl)-1-[(2-fluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound FC1=CC=CC=C1CN1C2=NC(NC=3C(=NNC=3)Cl)=NC=C2C=N1 KIWSWKLNGSBSTL-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
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• XFEFFUGLTIQZGT-UHFFFAOYSA-N n-[1-(2,2-difluoroethyl)-3-methylpyrazol-4-yl]-1-[(2,5-difluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C(=CC=C(F)C=3)F)C2=N1 XFEFFUGLTIQZGT-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
• SBSFCPMXDQCKNY-UHFFFAOYSA-N n-[1-(2,2-difluoroethyl)pyrazol-4-yl]-1-[(2-fluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CC(F)F)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)F)C2=N1 SBSFCPMXDQCKNY-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 class 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
• BPAPEMYUUZFUML-UHFFFAOYSA-N n-[1-(2,2-difluoroethyl)pyrazol-4-yl]-1-[[3-(2-methoxyethoxy)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COCCOC1=CC=CC(CN2C3=NC(NC4=CN(CC(F)F)N=C4)=NC=C3C=N2)=C1 BPAPEMYUUZFUML-UHFFFAOYSA-N 0.000 claims description 3
• WIKVBJZAIVMDAD-UHFFFAOYSA-N n-[1-[2-(diethylamino)ethyl]pyrazol-4-yl]-1-[(2-fluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CCN(CC)CC)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)F)C2=N1 WIKVBJZAIVMDAD-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 class 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
• OWYHDTRNPAQEJU-UHFFFAOYSA-N n-[1-[3-(dimethylamino)propyl]pyrazol-4-yl]-1-[(2-fluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(CCCN(C)C)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)F)C2=N1 OWYHDTRNPAQEJU-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
• CIDCZJMJYKYXOO-UHFFFAOYSA-N n-[1-[3-(dimethylamino)propyl]pyrazol-4-yl]-1-[[3-(2-methoxyethoxy)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COCCOC1=CC=CC(CN2C3=NC(NC4=CN(CCCN(C)C)N=C4)=NC=C3C=N2)=C1 CIDCZJMJYKYXOO-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
• 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 description 3
• DYQAUCYIPLGAPE-UHFFFAOYSA-N n-[2-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=CC=CC=3)NS(C)(=O)=O)C2=N1 DYQAUCYIPLGAPE-UHFFFAOYSA-N 0.000 claims description 3
• 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
• MJXZXEWEFOEUAY-UHFFFAOYSA-N n-[3-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(NS(C)(=O)=O)C=CC=3)C2=N1 MJXZXEWEFOEUAY-UHFFFAOYSA-N 0.000 claims description 3
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