JP2017052805A5 - - Google Patents
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- Publication number
- JP2017052805A5 JP2017052805A5 JP2016248325A JP2016248325A JP2017052805A5 JP 2017052805 A5 JP2017052805 A5 JP 2017052805A5 JP 2016248325 A JP2016248325 A JP 2016248325A JP 2016248325 A JP2016248325 A JP 2016248325A JP 2017052805 A5 JP2017052805 A5 JP 2017052805A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- methyl
- pyrazolo
- pyrimidin
- chloro
- 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 37
- -1 -OH Chemical group 0.000 claims 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 26
- JFDZBHWFFUWGJE-UHFFFAOYSA-N Benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 24
- 239000011780 sodium chloride Substances 0.000 claims 24
- 239000008194 pharmaceutical composition Substances 0.000 claims 22
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 21
- 125000005843 halogen group Chemical group 0.000 claims 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 9
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 8
- 108040005185 1-phosphatidylinositol-3-kinase activity proteins Proteins 0.000 claims 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 7
- 125000006601 (C1-C3) alkylcarbamyl group Chemical group 0.000 claims 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 5
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 5
- 239000003937 drug carrier Substances 0.000 claims 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims 4
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 3
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- WSJWSMDGJQMOSH-AMGKYWFPSA-N (2S)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]azetidin-1-yl]propan-2-ol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(C[C@H](C)O)C1 WSJWSMDGJQMOSH-AMGKYWFPSA-N 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- WFJBTQYBCMJYNG-UHFFFAOYSA-N 1-[1-[5-chloro-4-fluoro-2-methoxy-3-(1-propan-2-ylazetidin-3-yl)phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(C(C)C)C1 WFJBTQYBCMJYNG-UHFFFAOYSA-N 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 206010069351 Acute lung injury Diseases 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000009856 Lung Disease Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 201000005787 hematologic cancer Diseases 0.000 claims 2
- 125000005842 heteroatoms Chemical group 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- WSJWSMDGJQMOSH-JTDNENJMSA-N (2R)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]azetidin-1-yl]propan-2-ol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(C[C@@H](C)O)C1 WSJWSMDGJQMOSH-JTDNENJMSA-N 0.000 claims 1
- RJWNXJAXIOIPGQ-ARLHGKGLSA-N (2R)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]azetidin-1-yl]-2-hydroxypropan-1-one Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(=O)[C@@H](C)O)C1 RJWNXJAXIOIPGQ-ARLHGKGLSA-N 0.000 claims 1
- FBRKRAOGHVCFCB-KEKZHRQWSA-N (2R)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]azetidin-1-yl]propan-2-ol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C[C@@H](C)O)C1 FBRKRAOGHVCFCB-KEKZHRQWSA-N 0.000 claims 1
- GAKDFKQPUPMQJG-ZGTCLIOFSA-N (2R)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-2-hydroxypropan-1-one Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(=O)[C@@H](C)O)C1 GAKDFKQPUPMQJG-ZGTCLIOFSA-N 0.000 claims 1
- CJNJLCYTPKHVSM-YNODCEANSA-N (2R)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]propan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C[C@@H](C)O)C1 CJNJLCYTPKHVSM-YNODCEANSA-N 0.000 claims 1
- GECCYCCZNPQZQM-NFJWQWPMSA-N (2R)-1-[3-[3-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]azetidin-1-yl]propan-2-ol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(Cl)C(F)=C1C1CN(C[C@@H](C)O)C1 GECCYCCZNPQZQM-NFJWQWPMSA-N 0.000 claims 1
- UBGGPHDJPPNZSA-RWANSRKNSA-N (2R)-1-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2,3-dichloro-6-methoxyphenyl]azetidin-1-yl]propan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(Cl)=C1C1CN(C[C@@H](C)O)C1 UBGGPHDJPPNZSA-RWANSRKNSA-N 0.000 claims 1
- QKFMWXFSQKPVRN-RWANSRKNSA-N (2R)-1-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-fluoro-6-methoxyphenyl]azetidin-1-yl]propan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(C[C@@H](C)O)C1 QKFMWXFSQKPVRN-RWANSRKNSA-N 0.000 claims 1
- LFGMFYJYCSUPQS-YSSOQSIOSA-N (2R)-2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-N,N-dimethylpropanamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN([C@H](C)C(=O)N(C)C)C1 LFGMFYJYCSUPQS-YSSOQSIOSA-N 0.000 claims 1
- NNRGDBFNOMUWIU-ARLHGKGLSA-N (2R)-2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-N-methylpropanamide Chemical compound C1N([C@H](C)C(=O)NC)CC1C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1OC NNRGDBFNOMUWIU-ARLHGKGLSA-N 0.000 claims 1
- FXHJMVGKCZMISA-YNODCEANSA-N (2R)-2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]propan-1-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN([C@H](C)CO)C1 FXHJMVGKCZMISA-YNODCEANSA-N 0.000 claims 1
- GMDNBZXUPFSLSL-ZGTCLIOFSA-N (2R)-2-[3-[3-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-cyano-2-methoxy-6-methylphenyl]azetidin-1-yl]-N-methylpropanamide Chemical compound C1N([C@H](C)C(=O)NC)CC1C1=C(C)C(C#N)=CC(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)=C1OC GMDNBZXUPFSLSL-ZGTCLIOFSA-N 0.000 claims 1
- ZTUGTNZSYGNOFE-PVQCJRHBSA-N (2R)-3-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-1,1,1-trifluoropropan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C[C@@H](O)C(F)(F)F)C1 ZTUGTNZSYGNOFE-PVQCJRHBSA-N 0.000 claims 1
- RJWNXJAXIOIPGQ-KZUDCZAMSA-N (2S)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]azetidin-1-yl]-2-hydroxypropan-1-one Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(=O)[C@H](C)O)C1 RJWNXJAXIOIPGQ-KZUDCZAMSA-N 0.000 claims 1
- FBRKRAOGHVCFCB-SFVWDYPZSA-N (2S)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]azetidin-1-yl]propan-2-ol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C[C@H](C)O)C1 FBRKRAOGHVCFCB-SFVWDYPZSA-N 0.000 claims 1
- GAKDFKQPUPMQJG-ABLWVSNPSA-N (2S)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-2-hydroxypropan-1-one Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(=O)[C@H](C)O)C1 GAKDFKQPUPMQJG-ABLWVSNPSA-N 0.000 claims 1
- CJNJLCYTPKHVSM-ZSOXZCCMSA-N (2S)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]propan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C[C@H](C)O)C1 CJNJLCYTPKHVSM-ZSOXZCCMSA-N 0.000 claims 1
- GECCYCCZNPQZQM-VUWPPUDQSA-N (2S)-1-[3-[3-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]azetidin-1-yl]propan-2-ol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(Cl)C(F)=C1C1CN(C[C@H](C)O)C1 GECCYCCZNPQZQM-VUWPPUDQSA-N 0.000 claims 1
- UBGGPHDJPPNZSA-NUHJPDEHSA-N (2S)-1-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2,3-dichloro-6-methoxyphenyl]azetidin-1-yl]propan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(Cl)=C1C1CN(C[C@H](C)O)C1 UBGGPHDJPPNZSA-NUHJPDEHSA-N 0.000 claims 1
- QKFMWXFSQKPVRN-NUHJPDEHSA-N (2S)-1-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-fluoro-6-methoxyphenyl]azetidin-1-yl]propan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(C[C@H](C)O)C1 QKFMWXFSQKPVRN-NUHJPDEHSA-N 0.000 claims 1
- YDMJHCKEJJAXGY-RGURZIINSA-N (2S)-1-[3-[5-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-chloro-2-fluoro-6-methoxyphenyl]azetidin-1-yl]propan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(Cl)C(F)=C1C1CN(C[C@H](C)O)C1 YDMJHCKEJJAXGY-RGURZIINSA-N 0.000 claims 1
- LFGMFYJYCSUPQS-LOACHALJSA-N (2S)-2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-N,N-dimethylpropanamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN([C@@H](C)C(=O)N(C)C)C1 LFGMFYJYCSUPQS-LOACHALJSA-N 0.000 claims 1
- FXHJMVGKCZMISA-ZSOXZCCMSA-N (2S)-2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]propan-1-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN([C@@H](C)CO)C1 FXHJMVGKCZMISA-ZSOXZCCMSA-N 0.000 claims 1
- GMDNBZXUPFSLSL-ABLWVSNPSA-N (2S)-2-[3-[3-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-cyano-2-methoxy-6-methylphenyl]azetidin-1-yl]-N-methylpropanamide Chemical compound C1N([C@@H](C)C(=O)NC)CC1C1=C(C)C(C#N)=CC(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)=C1OC GMDNBZXUPFSLSL-ABLWVSNPSA-N 0.000 claims 1
- ZTUGTNZSYGNOFE-INSVYWFGSA-N (2S)-3-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-1,1,1-trifluoropropan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C[C@H](O)C(F)(F)F)C1 ZTUGTNZSYGNOFE-INSVYWFGSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006599 (C1-C3) alkylaminocarbonylamino group Chemical group 0.000 claims 1
- 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims 1
- 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims 1
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims 1
- 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- WUNNBRIRNAKJLH-UHFFFAOYSA-N 1-[1-[4,5-dichloro-2-methoxy-3-(1-propan-2-ylazetidin-3-yl)phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(Cl)=C1C1CN(C(C)C)C1 WUNNBRIRNAKJLH-UHFFFAOYSA-N 0.000 claims 1
- JUIUKAYNNVNLFM-UHFFFAOYSA-N 1-[1-[4,5-dichloro-2-methoxy-3-[1-(oxetan-3-yl)azetidin-3-yl]phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(Cl)=C1C(C1)CN1C1COC1 JUIUKAYNNVNLFM-UHFFFAOYSA-N 0.000 claims 1
- RMFYBQIIKKPTTD-UHFFFAOYSA-N 1-[1-[4,5-dichloro-3-(1-ethylazetidin-3-yl)-2-methoxyphenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1N(CC)CC1C1=C(Cl)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1OC RMFYBQIIKKPTTD-UHFFFAOYSA-N 0.000 claims 1
- AAWZQJPEIFGHDO-UHFFFAOYSA-N 1-[1-[5-chloro-2-ethoxy-3-(1-ethylazetidin-3-yl)-4-fluorophenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(CC)C1 AAWZQJPEIFGHDO-UHFFFAOYSA-N 0.000 claims 1
- FSOPVIXIALYKMT-UHFFFAOYSA-N 1-[1-[5-chloro-2-ethoxy-4-fluoro-3-(1-methylazetidin-3-yl)phenyl]ethyl]-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(Cl)C(F)=C1C1CN(C)C1 FSOPVIXIALYKMT-UHFFFAOYSA-N 0.000 claims 1
- OQOHCCLTCJIZQH-UHFFFAOYSA-N 1-[1-[5-chloro-2-ethoxy-4-fluoro-3-(1-methylazetidin-3-yl)phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(C)C1 OQOHCCLTCJIZQH-UHFFFAOYSA-N 0.000 claims 1
- YAJLBPCDJZEOJM-UHFFFAOYSA-N 1-[1-[5-chloro-2-ethoxy-4-fluoro-3-(1-propan-2-ylazetidin-3-yl)phenyl]ethyl]-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(Cl)C(F)=C1C1CN(C(C)C)C1 YAJLBPCDJZEOJM-UHFFFAOYSA-N 0.000 claims 1
- DKWCACOYZCVWAR-UHFFFAOYSA-N 1-[1-[5-chloro-2-ethoxy-4-fluoro-3-(1-propan-2-ylazetidin-3-yl)phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(C(C)C)C1 DKWCACOYZCVWAR-UHFFFAOYSA-N 0.000 claims 1
- FCICEBDJPUNKNB-UHFFFAOYSA-N 1-[1-[5-chloro-2-ethoxy-4-fluoro-3-[1-(2,2,2-trifluoroethyl)azetidin-3-yl]phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(CC(F)(F)F)C1 FCICEBDJPUNKNB-UHFFFAOYSA-N 0.000 claims 1
- MSXPSGQGKSWASD-UHFFFAOYSA-N 1-[1-[5-chloro-2-ethoxy-4-methyl-3-(1-propan-2-ylazetidin-3-yl)phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(C)C)C1 MSXPSGQGKSWASD-UHFFFAOYSA-N 0.000 claims 1
- BVISSWCHEUOQLQ-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-3-(1-methylazetidin-3-yl)phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C)C1 BVISSWCHEUOQLQ-UHFFFAOYSA-N 0.000 claims 1
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- KVXTVARPRRDFIC-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-3-(1-propan-2-ylazetidin-3-yl)phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(C)C)C1 KVXTVARPRRDFIC-UHFFFAOYSA-N 0.000 claims 1
- CELNSDNTUCEZMR-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-3-[1-(2,2,2-trifluoroethyl)azetidin-3-yl]phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CC(F)(F)F)C1 CELNSDNTUCEZMR-UHFFFAOYSA-N 0.000 claims 1
- IGRFIIIDNJIJPQ-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-3-[1-(2-methylpropyl)azetidin-3-yl]phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CC(C)C)C1 IGRFIIIDNJIJPQ-UHFFFAOYSA-N 0.000 claims 1
- WAVKYLNJUFLKTN-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-3-[1-(oxan-4-yl)azetidin-3-yl]phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(C1)CN1C1CCOCC1 WAVKYLNJUFLKTN-UHFFFAOYSA-N 0.000 claims 1
- LNEMXRLXBGKBPW-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-3-[1-(oxolan-3-yl)azetidin-3-yl]phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(C1)CN1C1CCOC1 LNEMXRLXBGKBPW-UHFFFAOYSA-N 0.000 claims 1
- RTBAGNKTRZBJDQ-UHFFFAOYSA-N 1-[1-[5-chloro-3-(1-ethylazetidin-3-yl)-2-methoxy-4-methylphenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1N(CC)CC1C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1OC RTBAGNKTRZBJDQ-UHFFFAOYSA-N 0.000 claims 1
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- VJPZSYLHUFXUDU-UHFFFAOYSA-N 1-[1-[5-chloro-3-[1-(2,2-difluoroethyl)azetidin-3-yl]-2-ethoxy-4-fluorophenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(CC(F)F)C1 VJPZSYLHUFXUDU-UHFFFAOYSA-N 0.000 claims 1
- GZWKYXNHQQGREC-UHFFFAOYSA-N 1-[1-[5-chloro-3-[1-(2,2-difluoroethyl)azetidin-3-yl]-2-methoxy-4-methylphenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CC(F)F)C1 GZWKYXNHQQGREC-UHFFFAOYSA-N 0.000 claims 1
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- QGARQSCJBPNHNL-UHFFFAOYSA-N 1-[1-[5-chloro-4-fluoro-2-methoxy-3-(1-propan-2-ylazetidin-3-yl)phenyl]ethyl]-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(Cl)C(F)=C1C1CN(C(C)C)C1 QGARQSCJBPNHNL-UHFFFAOYSA-N 0.000 claims 1
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- FRLYPMNWGJJLEF-UHFFFAOYSA-N 1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]azetidin-1-yl]-2-methylpropan-2-ol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CC(C)(C)O)C1 FRLYPMNWGJJLEF-UHFFFAOYSA-N 0.000 claims 1
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- GFOLYFQUUQLCIM-UHFFFAOYSA-N 1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CC1C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1OC GFOLYFQUUQLCIM-UHFFFAOYSA-N 0.000 claims 1
- VNFYPKVEZOGQKI-UHFFFAOYSA-N 1-[3-[3-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]azetidin-1-yl]-2-methylpropan-2-ol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(Cl)C(F)=C1C1CN(CC(C)(C)O)C1 VNFYPKVEZOGQKI-UHFFFAOYSA-N 0.000 claims 1
- YEPQYHYCTPHTBV-UHFFFAOYSA-N 1-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2,3-dichloro-6-methoxyphenyl]azetidin-1-yl]-2-methylpropan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(Cl)=C1C1CN(CC(C)(C)O)C1 YEPQYHYCTPHTBV-UHFFFAOYSA-N 0.000 claims 1
- PLVQCJNTGDAXRS-UHFFFAOYSA-N 1-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2,3-dichloro-6-methoxyphenyl]azetidin-1-yl]ethanone Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(Cl)=C1C1CN(C(C)=O)C1 PLVQCJNTGDAXRS-UHFFFAOYSA-N 0.000 claims 1
- OQMGPRGFANVWCT-UHFFFAOYSA-N 1-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-fluoro-6-methoxyphenyl]azetidin-1-yl]-2-methylpropan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(CC(C)(C)O)C1 OQMGPRGFANVWCT-UHFFFAOYSA-N 0.000 claims 1
- KZHQTNPGNQFKMC-UHFFFAOYSA-N 2-(1-acetylazetidin-3-yl)-4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxybenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(C)=O)C1 KZHQTNPGNQFKMC-UHFFFAOYSA-N 0.000 claims 1
- PWGIGBFGHYFIBK-UHFFFAOYSA-N 2-(1-acetylazetidin-3-yl)-4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(C)=O)C1 PWGIGBFGHYFIBK-UHFFFAOYSA-N 0.000 claims 1
- WPLLONBBBBTHIP-UHFFFAOYSA-N 2-[1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]cyclobutyl]acetonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(C1)CN1C1(CC#N)CCC1 WPLLONBBBBTHIP-UHFFFAOYSA-N 0.000 claims 1
- OOFVSYAIFFUZAM-UHFFFAOYSA-N 2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]azetidin-1-yl]ethanol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(CCO)C1 OOFVSYAIFFUZAM-UHFFFAOYSA-N 0.000 claims 1
- UWELQOKGACQCNG-UHFFFAOYSA-N 2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]azetidin-1-yl]ethanol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CCO)C1 UWELQOKGACQCNG-UHFFFAOYSA-N 0.000 claims 1
- VJBZYNUINOYICB-UHFFFAOYSA-N 2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-3,3,3-trifluoropropan-1-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(CO)C(F)(F)F)C1 VJBZYNUINOYICB-UHFFFAOYSA-N 0.000 claims 1
- DVVNMGCJKBIXHN-UHFFFAOYSA-N 2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]acetonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CC#N)C1 DVVNMGCJKBIXHN-UHFFFAOYSA-N 0.000 claims 1
- JBCBZHKCOKPHKX-UHFFFAOYSA-N 2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]ethanol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CCO)C1 JBCBZHKCOKPHKX-UHFFFAOYSA-N 0.000 claims 1
- DJNDEKXHLAWIML-UHFFFAOYSA-N 2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]propanenitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(C)C#N)C1 DJNDEKXHLAWIML-UHFFFAOYSA-N 0.000 claims 1
- ONURBHYTEKTOIG-UHFFFAOYSA-N 2-[3-[3-[1-(4-amino-3-pyrazol-4-ylidene-2H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]acetonitrile Chemical compound COC1=C(C(C)N2C3=C(C(=NC=N3)N)C(=C3C=NN=C3)N2)C=C(Cl)C(C)=C1C1CN(CC#N)C1 ONURBHYTEKTOIG-UHFFFAOYSA-N 0.000 claims 1
- OMWMDQLAODHBCM-UHFFFAOYSA-N 2-[3-[3-[1-[4-amino-3-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]acetonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C3=CN(C)N=C3)=N2)C=C(Cl)C(C)=C1C1CN(CC#N)C1 OMWMDQLAODHBCM-UHFFFAOYSA-N 0.000 claims 1
- QIUBAVSRQAJLHV-UHFFFAOYSA-N 2-[3-[3-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]azetidin-1-yl]ethanol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(Cl)C(F)=C1C1CN(CCO)C1 QIUBAVSRQAJLHV-UHFFFAOYSA-N 0.000 claims 1
- OCILFYDOEKWMEW-UHFFFAOYSA-N 2-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2,3-dichloro-6-methoxyphenyl]azetidin-1-yl]acetonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(Cl)=C1C1CN(CC#N)C1 OCILFYDOEKWMEW-UHFFFAOYSA-N 0.000 claims 1
- QCNVWRCCTQZPQV-UHFFFAOYSA-N 2-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-ethoxyphenyl]azetidin-1-yl]-2-methylpropanamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(C)(C)C(N)=O)C1 QCNVWRCCTQZPQV-UHFFFAOYSA-N 0.000 claims 1
- GSTJCAXUOLBAMZ-UHFFFAOYSA-N 2-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-ethoxyphenyl]azetidin-1-yl]-N,2-dimethylpropanamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(C)(C)C(=O)NC)C1 GSTJCAXUOLBAMZ-UHFFFAOYSA-N 0.000 claims 1
- NENSZFPDCTVZCA-UHFFFAOYSA-N 2-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-ethoxyphenyl]azetidin-1-yl]-N,N,2-trimethylpropanamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(C)(C)C(=O)N(C)C)C1 NENSZFPDCTVZCA-UHFFFAOYSA-N 0.000 claims 1
- MLARYDAXPYMQPL-UHFFFAOYSA-N 2-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-fluoro-6-methoxyphenyl]azetidin-1-yl]ethanol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(CCO)C1 MLARYDAXPYMQPL-UHFFFAOYSA-N 0.000 claims 1
- FXYYRCLDRBLGLE-UHFFFAOYSA-N 2-[3-[5-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-chloro-2-fluoro-6-methoxyphenyl]azetidin-1-yl]ethanol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(Cl)C(F)=C1C1CN(CCO)C1 FXYYRCLDRBLGLE-UHFFFAOYSA-N 0.000 claims 1
- DWNHWODSDASXQL-UHFFFAOYSA-N 3-(1-acetylazetidin-3-yl)-5-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-4-methoxy-2-methylbenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(C#N)C(C)=C1C1CN(C(C)=O)C1 DWNHWODSDASXQL-UHFFFAOYSA-N 0.000 claims 1
- CWCRGAQAZXYCCJ-UHFFFAOYSA-N 3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-N-methylazetidine-1-carboxamide Chemical compound C1N(C(=O)NC)CC1C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1OC CWCRGAQAZXYCCJ-UHFFFAOYSA-N 0.000 claims 1
- ZTUGTNZSYGNOFE-UHFFFAOYSA-N 3-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-1,1,1-trifluoropropan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CC(O)C(F)(F)F)C1 ZTUGTNZSYGNOFE-UHFFFAOYSA-N 0.000 claims 1
- VJDCSAJOSXRANY-UHFFFAOYSA-N 3-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-2-methylpropanenitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CC(C)C#N)C1 VJDCSAJOSXRANY-UHFFFAOYSA-N 0.000 claims 1
- FSENVPSVXHTCND-UHFFFAOYSA-N 3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-ethoxyphenyl]-N,N-dimethylazetidine-1-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(=O)N(C)C)C1 FSENVPSVXHTCND-UHFFFAOYSA-N 0.000 claims 1
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- UGADQIDSYFDZGQ-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxy-2-(1-propan-2-ylazetidin-3-yl)benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(C)C)C1 UGADQIDSYFDZGQ-UHFFFAOYSA-N 0.000 claims 1
- XZVJVDMFFGQDRG-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxy-2-(1-propan-2-ylsulfonylazetidin-3-yl)benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(S(=O)(=O)C(C)C)C1 XZVJVDMFFGQDRG-UHFFFAOYSA-N 0.000 claims 1
- UUXZLQZVATVBPF-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxy-2-(1-propanoylazetidin-3-yl)benzonitrile Chemical compound C1N(C(=O)CC)CC1C1=C(OC)C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=CC(Cl)=C1C#N UUXZLQZVATVBPF-UHFFFAOYSA-N 0.000 claims 1
- ZGHBNTTVFVZUES-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxy-2-[1-(2-methylpropanoyl)azetidin-3-yl]benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(=O)C(C)C)C1 ZGHBNTTVFVZUES-UHFFFAOYSA-N 0.000 claims 1
- OICQQMDXRMYLPW-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxy-2-[1-(oxan-4-yl)azetidin-3-yl]benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C(C1)CN1C1CCOCC1 OICQQMDXRMYLPW-UHFFFAOYSA-N 0.000 claims 1
- SIKWOSDZUGQNOU-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxy-2-[1-(oxan-4-ylmethyl)azetidin-3-yl]benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C(C1)CN1CC1CCOCC1 SIKWOSDZUGQNOU-UHFFFAOYSA-N 0.000 claims 1
- PPURAVRTZVKOKD-UHFFFAOYSA-N 4-[1-(4-amino-5-methylpyrrolo[2,3-d]pyrimidin-7-yl)ethyl]-6-chloro-3-ethoxy-2-(1-propan-2-ylazetidin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=C2)C=C(Cl)C(C#N)=C1C1CN(C(C)C)C1 PPURAVRTZVKOKD-UHFFFAOYSA-N 0.000 claims 1
- LXCBMDGJBNPUHR-MLCCFXAWSA-N 4-[1-(4-amino-5-methylpyrrolo[2,3-d]pyrimidin-7-yl)ethyl]-6-chloro-3-ethoxy-2-[1-[(2S)-2-hydroxypropyl]azetidin-3-yl]benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=C2)C=C(Cl)C(C#N)=C1C1CN(C[C@H](C)O)C1 LXCBMDGJBNPUHR-MLCCFXAWSA-N 0.000 claims 1
- RCGSMTNQKQQWQT-UHFFFAOYSA-N 4-amino-8-[1-[5-chloro-2-ethoxy-4-methyl-3-(1-propan-2-ylazetidin-3-yl)phenyl]ethyl]pyrido[2,3-d]pyrimidin-5-one Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(=O)C=C2)C=C(Cl)C(C)=C1C1CN(C(C)C)C1 RCGSMTNQKQQWQT-UHFFFAOYSA-N 0.000 claims 1
- NIFBGSFNHVDRNQ-UHFFFAOYSA-N 4-amino-8-[1-[5-chloro-2-methoxy-4-methyl-3-(1-propan-2-ylazetidin-3-yl)phenyl]ethyl]pyrido[2,3-d]pyrimidin-5-one Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(=O)C=C2)C=C(Cl)C(C)=C1C1CN(C(C)C)C1 NIFBGSFNHVDRNQ-UHFFFAOYSA-N 0.000 claims 1
- LYGFCLHDXSUKSI-VUWPPUDQSA-N 5-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-2-fluoro-3-[1-[(2S)-2-hydroxypropyl]azetidin-3-yl]-4-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(C#N)C(F)=C1C1CN(C[C@H](C)O)C1 LYGFCLHDXSUKSI-VUWPPUDQSA-N 0.000 claims 1
- YKLIUZKQUOCJPP-UHFFFAOYSA-N 5-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-[1-(2,2-difluoroethyl)azetidin-3-yl]-4-methoxy-2-methylbenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(C#N)C(C)=C1C1CN(CC(F)F)C1 YKLIUZKQUOCJPP-UHFFFAOYSA-N 0.000 claims 1
- OKLLIBZLGKJVBJ-UHFFFAOYSA-N 5-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-[1-(2-hydroxyethyl)azetidin-3-yl]-4-methoxy-2-methylbenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(C#N)C(C)=C1C1CN(CCO)C1 OKLLIBZLGKJVBJ-UHFFFAOYSA-N 0.000 claims 1
- IDVAKCBQSLPPNH-UHFFFAOYSA-N 5-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-4-methoxy-2-methyl-3-(1-propan-2-ylazetidin-3-yl)benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(C#N)C(C)=C1C1CN(C(C)C)C1 IDVAKCBQSLPPNH-UHFFFAOYSA-N 0.000 claims 1
- GYWVNFICSRNCMU-UHFFFAOYSA-N 5-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-4-methoxy-2-methyl-3-[1-(2,2,2-trifluoroethyl)azetidin-3-yl]benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C(F)F)=N2)C=C(C#N)C(C)=C1C1CN(CC(F)(F)F)C1 GYWVNFICSRNCMU-UHFFFAOYSA-N 0.000 claims 1
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- BVYVSUUHEINNDU-UHFFFAOYSA-N C1N(C(C)(C)C(=O)OCC)CC1C1=C(OCC)C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=CC(Cl)=C1C#N Chemical compound C1N(C(C)(C)C(=O)OCC)CC1C1=C(OCC)C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=CC(Cl)=C1C#N BVYVSUUHEINNDU-UHFFFAOYSA-N 0.000 claims 1
- LSKQFKWRGIDVRW-UHFFFAOYSA-N CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(CC)C1 Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(CC)C1 LSKQFKWRGIDVRW-UHFFFAOYSA-N 0.000 claims 1
- YQOCDMFKKLHYAU-UHFFFAOYSA-N COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(CC(C)C)C1 Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(CC(C)C)C1 YQOCDMFKKLHYAU-UHFFFAOYSA-N 0.000 claims 1
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- 206010012818 Diffuse large B-cell lymphoma Diseases 0.000 claims 1
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- 208000008456 Leukemia, Myelogenous, Chronic, BCR-ABL Positive Diseases 0.000 claims 1
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- IRSHORZQIUSICQ-UHFFFAOYSA-N NC1=C2C(=NC=N1)N(N=C2C)C(C)C=1C(=C(C(=C(C=1)Cl)Cl)C1CN(C1)CCO)OC Chemical compound NC1=C2C(=NC=N1)N(N=C2C)C(C)C=1C(=C(C(=C(C=1)Cl)Cl)C1CN(C1)CCO)OC IRSHORZQIUSICQ-UHFFFAOYSA-N 0.000 claims 1
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- 102000030951 Phosphotransferases Human genes 0.000 claims 1
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- WTSBHJMSFQJENA-UHFFFAOYSA-N [3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]azetidin-1-yl]-(1-methylpyrazol-4-yl)methanone Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(C1)CN1C(=O)C=1C=NN(C)C=1 WTSBHJMSFQJENA-UHFFFAOYSA-N 0.000 claims 1
- ADIDIOGKAWIIFU-UHFFFAOYSA-N [3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-(1-hydroxycyclopropyl)methanone Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(C1)CN1C(=O)C1(O)CC1 ADIDIOGKAWIIFU-UHFFFAOYSA-N 0.000 claims 1
- MIJQPAFFDSJUCM-UHFFFAOYSA-N [3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-(1-methylpyrazol-4-yl)methanone Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(C1)CN1C(=O)C=1C=NN(C)C=1 MIJQPAFFDSJUCM-UHFFFAOYSA-N 0.000 claims 1
- FBHZGJSGJXHTFB-UHFFFAOYSA-N [3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-(1H-pyrazol-4-yl)methanone Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(C1)CN1C(=O)C=1C=NNC=1 FBHZGJSGJXHTFB-UHFFFAOYSA-N 0.000 claims 1
- GCAJHGWOMWYLNL-UHFFFAOYSA-N [3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-(5-methyl-1,2-oxazol-4-yl)methanone Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(C1)CN1C(=O)C=1C=NOC=1C GCAJHGWOMWYLNL-UHFFFAOYSA-N 0.000 claims 1
- DFZABDFGCIGGKC-UHFFFAOYSA-N [3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-cyclopropylmethanone Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(C1)CN1C(=O)C1CC1 DFZABDFGCIGGKC-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 201000005794 allergic hypersensitivity disease Diseases 0.000 claims 1
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
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- WOMUYKUYGVUOFW-UHFFFAOYSA-N methyl 3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-methoxyphenyl]azetidine-1-carboxylate Chemical compound C1N(C(=O)OC)CC1C1=C(OC)C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=CC(Cl)=C1C#N WOMUYKUYGVUOFW-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
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- 230000036473 myasthenia Effects 0.000 claims 1
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- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- 201000004681 psoriasis Diseases 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 200000000008 restenosis Diseases 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- ZDWVTAJNKPYTCP-UHFFFAOYSA-N tert-butyl 2-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-ethoxyphenyl]azetidin-1-yl]-2-methylpropanoate Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(C)(C)C(=O)OC(C)(C)C)C1 ZDWVTAJNKPYTCP-UHFFFAOYSA-N 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
Claims (35)
- 下記式:
XはCR9またはNであり;
WはCR7またはNであり;
YはCR8、CR8a、またはNであり;
Zは結合またはC(=O)であり;
但し、−W=Y−Z−が、−CR7=CR8−、−N=CR8−、−CR7=CR8a−C(=O)−、−N=CR8a−C(=O)−、または−CR7=N−C(=O)−であることを条件とし;
R1はC1−3アルキルであり;
R2はハロ、C1−6アルキル、C1−6アルコキシ、C1−6ハロアルキル、C1−6ハロアルコキシ、フェニル、または5〜6員ヘテロアリールであり;ここで前記フェニルおよび5〜6員ヘテロアリールは、それぞれ、ハロ、OH、CN、C1−4アルキル、C1−4アルコキシ、およびC1−4ハロアルコキシから独立して選択される、1個、2個、3個または4個の置換基により置換されていてもよく;
R4はH、ハロ、OH、CN、C1−4アルキル、C1−4ハロアルキル、C1−4アルコキシ、またはC1−4ハロアルコキシであり;
R5はハロ、OH、CN、C1−4アルキル、C1−4ハロアルキル、C1−4アルコキシ、C1−4ハロアルコキシ、またはシクロプロピルであり;
R6はH、ハロ、OH、CN、C1−4アルキル、C1−4ハロアルキル、C1−4アルコキシ、またはC1−4ハロアルコキシであり;
R7はHまたはC1−4アルキルであり;
R8はH、ハロ、−OH、−CN、C1−6アルキル、C2−6アルケニル、C2−6アルキニル、C1−6ハロアルキル、Cy2、−(C1−3アルキレン)−Cy2、ORa2、SRa2、C(=O)Rb2、C(=O)NRc2Rd2、C(=O)ORa2、OC(=O)Rb2、OC(=O)NRc2Rd2、NRc2Rd2、NRc2C(=O)Rb2、NRc2C(=O)ORb2、NRc2C(=O)NRc2Rd2、C(=NRe)Rb2、C(=NRe)NRc2Rd2、NRc2C(=NRe)NRc2Rd2、NRc2S(=O)Rb2、NRc2S(=O)2NRc2Rd2、S(=O)Rb2、S(=O)2Rb2、またはS(=O)2NRc2Rd2であり;ここで前記C1−6アルキル、C2−6アルケニル、C2−6アルキニルは、それぞれ、1個、2個、3個または4個の独立して選択されるR11基により置換されていてもよく;
R8aはH、ハロ、−CN、C1−6アルキル、C2−6アルケニル、C2−6アルキニル、C1−6ハロアルキル、Cy2、−(C1−3アルキレン)−Cy2、C(=O)Rb2、C(=O)NRc2Rd2、C(=O)ORa2、NRc2Rd2、NRc2C(=O)Rb2、NRc2C(=O)ORb2、NRc2C(=O)NRc2Rd2、NRc2S(=O)Rb2、NRc2S(=O)2NRc2Rd2、S(=O)Rb2、S(=O)2Rb2、またはS(=O)2NRc2Rd2であり;ここで前記C1−6アルキル、C2−6アルケニル、C2−6アルキニルは、それぞれ、1個、2個、3個または4個の独立して選択されるR11基により置換されていてもよく;
R9はH、ハロ、OH、CN、C1−4アルキル、C1−4ハロアルキル、C1−4アルコキシ、またはC1−4ハロアルコキシであり;
R10はHまたはC1−4アルキルであり;
各ReはH、CN、OH、C1−4アルキル、およびC1−4アルコキシから独立して選択され;
各R3bは、Cy1、−(C1−3アルキレン)−Cy1、ハロ、CN、NO2、C1−6アルキル、C2−6アルケニル、C2−6アルキニル、C1−6ハロアルキル、ORa1、SRa1、C(=O)Rb1、C(=O)NRc1Rd1、C(=O)ORa1、OC(=O)Rb1、OC(=O)NRc1Rd1、NRc1Rd1、NRc1C(=O)Rb1、NRc1C(=O)ORb1、NRc1C(=O)NRc1Rd1、C(=NRe)Rb1、C(=NRe)NRc1Rd1、NRc1C(=NRe)NRc1Rd1、NRc1S(=O)Rb1、NRc1S(=O)2NRc1Rd1、S(=O)Rb1、S(=O)2Rb1、およびS(=O)2NRc1Rd1から独立して選択され;ここで前記C1−6アルキル、C2−6アルケニル、C2−6アルキニルは、それぞれ、1個、2個または3個の独立して選択されるR11基で置換されていてもよく;
各Cy1は、それぞれが1個、2個、3個または4個の独立して選択されるR11基で置換されていてもよい、C3−7シクロアルキル、4〜7員ヘテロシクロアルキル、フェニル、および5〜6員ヘテロアリールから独立して選択され;
各Ra1、Rb1、Rc1、およびRd1は、H、C1−6アルキル、C1−6ハロアルキル、C2−6アルケニル、C2−6アルキニル、C3−7シクロアルキル、4〜7員ヘテロシクロアルキル、フェニル、および5〜6員ヘテロアリールから独立して選択され;ここで前記C1−6アルキル、C2−6アルケニル、C2−6アルキニル、C3−7シクロアルキル、4〜7員ヘテロシクロアルキル、フェニルおよび5〜6員ヘテロアリールは、それぞれ、1個、2個もしくは3個の独立して選択されるR11基で置換されていてもよいか;
またはRc1およびRd1は、それらが結合しているN原子と一緒になって、−OHもしくはC1−3アルキルで置換されていてもよい、4員、5員、6員もしくは7員ヘテロシクロアルキル基を形成し;
各Cy2は、それぞれが1個、2個、3個または4個の独立して選択されるR11基で置換されていてもよい、C3−7シクロアルキル、4〜7員ヘテロシクロアルキル、フェニル、5〜6員ヘテロアリール、または9〜10員二環式ヘテロアリールから独立して選択され;
各Ra2、Rb2、Rc2、およびRd2は、H、C1−6アルキル、C1−6ハロアルキル、C2−6アルケニル、C2−6アルキニル、C3−7シクロアルキル、4〜7員ヘテロシクロアルキル、フェニル、および5〜6員ヘテロアリールから独立して選択され;ここで前記C1−6アルキル、C2−6アルケニル、C2−6アルキニル、C3−7シクロアルキル、4〜7員ヘテロシクロアルキル、フェニルおよび5〜6員ヘテロアリールは、それぞれ、1個、2個もしくは3個の独立して選択されるR11基で置換されていてもよいか;
またはRc2およびRd2は、それらが結合しているN原子と一緒になって、−OHもしくはC1−3アルキルで置換されていてもよい、4員、5員、6員もしくは7員ヘテロシクロアルキル基を形成し;
各R11は、OH、NO2、CN、ハロ、C1−3アルキル、C2−3アルケニル、C2−3アルキニル、C1−3ハロアルキル、シアノ−C1−3アルキル、HO−C1−3アルキル、C1−3アルコキシ−C1−3アルキル、C3−7シクロアルキル、C1−3アルコキシ、C1−3ハロアルコキシ、アミノ、C1−3アルキルアミノ、ジ(C1−3アルキル)アミノ、チオ、C1−3アルキルチオ、C1−3アルキルスルフィニル、C1−3アルキルスルホニル、カルバミル、C1−3アルキルカルバミル、ジ(C1−3アルキル)カルバミル、カルボキシ、C1−3アルキルカルボニル、C1−4アルコキシカルボニル、C1−3アルキルカルボニルアミノ、C1−3アルキルスルホニルアミノ、アミノスルホニル、C1−3アルキルアミノスルホニル、ジ(C1−3アルキル)アミノスルホニル、アミノスルホニルアミノ、C1−3アルキルアミノスルホニルアミノ、ジ(C1−3アルキル)アミノスルホニルアミノ、アミノカルボニルアミノ、C1−3アルキルアミノカルボニルアミノ、およびジ(C1−3アルキル)アミノカルボニルアミノから独立して選択される]
で示される化合物、またはその薬剤的に許容される塩。 -
- R1がメチルである、請求項1〜2のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- R2がC1−6アルキル、C1−3アルコキシ、またはフェニルであり;ここで前記フェニルが、ハロから独立して選択される1個、2個、3個または4個の置換基で置換されていてもよい、請求項1〜3のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- R4がハロ、CN、またはC1−4アルキルである、請求項1〜4のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- R5がハロまたはCNである、請求項1〜5のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- R6がHである、請求項1〜6のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- R7がHである、請求項1〜7のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- R8がH、ハロ、CN、C1−6アルキル、またはCy2であり;ここでCy2が、それぞれが1個または2個の独立して選択されるR11基により置換されていてもよい、C3−6シクロアルキル、フェニル、5〜6員ヘテロアリール、および4〜7員ヘテロシクロアルキルから選択される、請求項1〜8のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- R8がH、ハロ、CN、C1−6アルキル、またはCy2であり;ここでCy2が、それぞれがOH、CN、ハロ、C1−3アルキル、C1−3ハロアルキル、HO−C1−3アルキル、C1−3アルコキシ−C1−3アルキル、C1−3アルコキシ、C1−3ハロアルコキシ、アミノ、C1−3アルキルアミノ、ジ(C1−3アルキル)アミノ、カルバミル、C1−3アルキルカルバミル、およびジ(C1−3アルキル)カルバミルから選択される1個のR11で置換されていてもよい、C3−6シクロアルキル、フェニル、5〜6員ヘテロアリール、または4〜7員ヘテロシクロアルキルから選択される、請求項1〜8のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- R8がH、ハロ、CN、メチル、またはCy2であり;ここでCy2が、それぞれがOH、CN、フルオロ、メチル、2−ヒドロキシエチル、ジメチルカルバミル、アミノ、メチルカルバミル、およびジメチルカルバミルから選択される1個のR11で置換されていてもよい、シクロプロピル、フェニル、ピラゾール環、ピリジン環、またはピリミジン環から選択される、請求項1〜8のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- R8aがH、ハロ、−CN、C1−6アルキル、C2−6アルケニル、C2−6アルキニル、C1−6ハロアルキル、またはCy2である、請求項1〜8のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- R8aがHまたはハロである、請求項1〜8のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- R9がHである、請求項1〜13のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- R10がHである、請求項1〜14のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- 各R11が独立して、OH、CN、ハロ、C1−3アルキル、C1−3ハロアルキル、HO−C1−3アルキル、C1−3アルコキシ−C1−3アルキル、C1−3アルコキシ、C1−3ハロアルコキシ、アミノ、C1−3アルキルアミノ、ジ(C1−3アルキル)アミノ、カルバミル、C1−3アルキルカルバミル、またはジ(C1−3アルキル)カルバミルである、請求項1〜15のいずれか1項に記載の化合物、またはその薬剤的に許容される塩。
- 化合物が、下記式:
- 1−{1−[5−クロロ−3−(1−イソプロピルアゼチジン−3−イル)−2−メトキシ−4−メチルフェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−{1−[3−(1−アセチルアゼチジン−3−イル)−5−クロロ−2−メトキシ−4−メチルフェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−{1−[5−クロロ−2−メトキシ−4−メチル−3−(1−プロピオニルアゼチジン−3−イル)フェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−(1−{5−クロロ−3−[1−(シクロプロピルメチル)アゼチジン−3−イル]−2−メトキシ−4−メチルフェニル}エチル)−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−{1−[5−クロロ−2−メトキシ−4−メチル−3−(1−メチルアゼチジン−3−イル)フェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−{1−[5−クロロ−3−(1−エチルアゼチジン−3−イル)−2−メトキシ−4−メチルフェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−{1−[5−クロロ−3−(1−イソブチルアゼチジン−3−イル)−2−メトキシ−4−メチルフェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−{1−[3−(1−sec−ブチルアゼチジン−3−イル)−5−クロロ−2−メトキシ−4−メチルフェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−(1−{5−クロロ−2−メトキシ−3−[1−(2−メトキシエチル)アゼチジン−3−イル]−4−メチルフェニル}エチル)−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}−N−メチルアゼチジン−1−カルボキサミド;
1−{1−[5−クロロ−4−フルオロ−3−(1−イソプロピルアゼチジン−3−イル)−2−メトキシフェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
4−アミノ−8−{1−[5−クロロ−3−(1−イソプロピルアゼチジン−3−イル)−2−メトキシ−4−メチルフェニル]エチル}ピリド[2,3−d]ピリミジン−5(8H)−オン;
4−アミノ−8−{1−[5−クロロ−2−エトキシ−3−(1−イソプロピルアゼチジン−3−イル)−4−メチルフェニル]エチル}ピリド[2,3−d]ピリミジン−5(8H)−オン;
1−{1−[5−クロロ−2−メトキシ−4−メチル−3−(1−オキセタン−3−イルアゼチジン−3−イル)フェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−(1−{5−クロロ−2−メトキシ−4−メチル−3−[1−(テトラヒドロ−2H−ピラン−4−イル)アゼチジン−3−イル]フェニル}エチル)−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−{1−[5−クロロ−4−フルオロ−3−(1−イソプロピルアゼチジン−3−イル)−2−メトキシフェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
(2S)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−フルオロ−2−メトキシフェニル}アゼチジン−1−イル)プロパン−2−オール;
2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−フルオロ−2−メトキシフェニル}アゼチジン−1−イル)エタノール;
1−{1−[5−クロロ−4−フルオロ−2−メトキシ−3−(1−オキセタン−3−イルアゼチジン−3−イル)フェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−{1−[5−クロロ−4−フルオロ−3−(1−イソプロピルアゼチジン−3−イル)−2−メトキシフェニル]エチル}−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
2−[3−(3−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−5−クロロ−6−フルオロ−2−メトキシフェニル)アゼチジン−1−イル]エタノール;
(2S)−1−[3−(3−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−5−クロロ−6−フルオロ−2−メトキシフェニル)アゼチジン−1−イル]プロパン−2−オール;
5−(1−(4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル)−2−フルオロ−3−(1−((S)−2−ヒドロキシプロピル)アゼチジン−3−イル)−4−メトキシベンゾニトリル;
1−{1−[5−クロロ−2−エトキシ−3−(1−イソプロピルアゼチジン−3−イル)−4−メチルフェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−エトキシ−6−メチルフェニル}アゼチジン−1−イル)エタノール;
(2S)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−エトキシ−6−メチルフェニル}アゼチジン−1−イル)プロパン−2−オール;
(2S)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−エトキシ−6−メチルフェニル}アゼチジン−1−イル)−1−オキソプロパン−2−オール;
1−[1−(5−クロロ−2−エトキシ−4−メチル−3−{1−[(1−メチル−1H−ピラゾール−4−イル)カルボニル]アゼチジン−3−イル}フェニル)エチル]−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
(2S)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)プロパン−2−オール;
2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)エタノール;
(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)アセトニトリル;
1−(1−{5−クロロ−2−メトキシ−4−メチル−3−[1−(2,2,2−triフルオロエチル)アゼチジン−3−イル]フェニル}エチル)−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
(2R)−2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)−N−メチルプロパンアミド;
2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)−3,3,3−トリフルオロプロパン−1−オール;
(2R)−3−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)−1,1,1−トリフルオロプロパン−2−オール;
1−[1−(5−クロロ−2−メトキシ−4−メチル−3−{1−[(1−メチル−1H−ピラゾール−4−イル)カルボニル]アゼチジン−3−イル}フェニル)エチル]−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
(2S)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)−1−オキソプロパン−2−オール;
(2R)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)−1−オキソプロパン−2−オール;
[3−(3−{1−[4−アミノ−3−(1−メチル−1H−ピラゾール−4−イル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−5−クロロ−2−メトキシ−6−メチルフェニル)アゼチジン−1−イル]アセトニトリル;
[3−(3−{1−[4−アミノ−3−(1H−ピラゾール−4−イル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−5−クロロ−2−メトキシ−6−メチルフェニル)アゼチジン−1−イル]アセトニトリル;
1−{1−[5−クロロ−3−(1−イソプロピルアゼチジン−3−イル)−2−メトキシ−4−メチルフェニル]エチル}−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
5−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−3−(1−イソプロピルアゼチジン−3−イル)−4−メトキシ−2−メチルベンゾニトリル;
5−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−4−メトキシ−2−メチル−3−[1−(2,2,2−トリフルオロエチル)アゼチジン−3−イル]ベンゾニトリル;
5−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−3−[1−(2−ヒドロキシエチル)アゼチジン−3−イル]−4−メトキシ−2−メチルベンゾニトリル;
5−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−3−{1−[(2S)−2−ヒドロキシプロピル]アゼチジン−3−イル}−4−メトキシ−2−メチルベンゾニトリル;
5−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−3−[1−(2−ヒドロキシ−2−メチルプロピル)アゼチジン−3−イル]−4−メトキシ−2−メチルベンゾニトリル;
(2S)−2−[3−(3−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−5−シアノ−2−メトキシ−6−メチルフェニル)アゼチジン−1−イル]−N−メチルプロパンアミド;
5−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−3−[1−(2,2−ジフルオロエチル)アゼチジン−3−イル]−4−メトキシ−2−メチルベンゾニトリル;
5−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−3−{1−[(2S)−2−ヒドロキシプロピル]アゼチジン−3−イル}−4−メトキシ−2−メチルベンゾニトリル;
3−(1−アセチルアゼチジン−3−イル)−5−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−4−メトキシ−2−メチルベンゾニトリル;
1−{1−[5−クロロ−2−エトキシ−4−フルオロ−3−(1−イソプロピルアゼチジン−3−イル)フェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−エトキシ−6−フルオロフェニル}アゼチジン−1−イル)−2−メチルプロパン−2−オール;
1−(1−{5−クロロ−2−エトキシ−4−フルオロ−3−[1−(2,2,2−トリフルオロエチル)アゼチジン−3−イル]フェニル}エチル)−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
(2S)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−エトキシ−6−フルオロフェニル}アゼチジン−1−イル)プロパン−2−オール;
1−{1−[5−クロロ−2−エトキシ−4−フルオロ−3−(1−イソプロピルアゼチジン−3−イル)フェニル]エチル}−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
2−[3−(3−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−5−クロロ−2−エトキシ−6−フルオロフェニル)アゼチジン−1−イル]エタノール;
(2R)−2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)プロパン−1−オール;
1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)−2−メチルプロパン−2−オール;
(2R)−2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)−N,N−ジメチルプロパンアミド;
[1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)シクロブチル]アセトニトリル;
(2R)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−フルオロ−2−メトキシフェニル}アゼチジン−1−イル)プロパン−2−オール;
1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−フルオロ−2−メトキシフェニル}アゼチジン−1−イル)−2−メチルプロパン−2−オール;
(2R)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−エトキシ−6−メチルフェニル}アゼチジン−1−イル)プロパン−2−オール;
1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−エトキシ−6−メチルフェニル}アゼチジン−1−イル)−2−メチルプロパン−2−オール;
(2R)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−エトキシ−6−メチルフェニル}アゼチジン−1−イル)−1−オキソプロパン−2−オール;
(2R)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)プロパン−2−オール;
2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)プロパンニトリル;
1−(1−{5−クロロ−2−メトキシ−4−メチル−3−[1−(テトラヒドロフラン−3−イル)アゼチジン−3−イル]フェニル}エチル)−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
3−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)−1,1,1−トリフルオロプロパン−2−オール;
2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)アセトアミド;
1−(1−{5−クロロ−3−[1−(2,2−ジフルオロエチル)アゼチジン−3−イル]−2−メトキシ−4−メチルフェニル}エチル)−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−(1−{5−クロロ−3−[1−(2−フルオロ−1−メチルエチル)アゼチジン−3−イル]−2−メトキシ−4−メチルフェニル}エチル)−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
(2S)−3−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)−1,1,1−トリフルオロプロパン−2−オール;
1−(1−{5−クロロ−3−[1−(シクロプロピルカルボニル)アゼチジン−3−イル]−2−メトキシ−4−メチルフェニル}エチル)−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−[1−(5−クロロ−2−メトキシ−4−メチル−3−{1−[(5−メチルイソオキサゾール−4−イル)カルボニル]アゼチジン−3−イル}フェニル)エチル]−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−[(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)カルボニル]シクロプロパノール;
1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)−2−メチル−1−オキソプロパン−2−オール;
1−(1−{5−クロロ−2−メトキシ−4−メチル−3−[1−(1H−ピラゾール−4−イルカルボニル)アゼチジン−3−イル]フェニル}エチル)−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
(2R)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−エトキシ−6−フルオロフェニル}アゼチジン−1−イル)プロパン−2−オール;
(2S)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−エトキシ−6−フルオロフェニル}アゼチジン−1−イル)プロパン−2−オール;
2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−エトキシ−6−フルオロフェニル}アゼチジン−1−イル)エタノール;
1−{1−[5−クロロ−2−エトキシ−4−フルオロ−3−(1−メチルアゼチジン−3−イル)フェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−{1−[5−クロロ−2−エトキシ−3−(1−エチルアゼチジン−3−イル)−4−フルオロフェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−(1−{5−クロロ−3−[1−(2,2−ジフルオロエチル)アゼチジン−3−イル]−2−エトキシ−4−フルオロフェニル}エチル)−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−エトキシ−6−フルオロフェニル}アゼチジン−1−イル)アセトアミド;
(2S)−2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)プロパン−1−オール;
(2S)−2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)−N,N−ジメチルプロパンアミド;
3−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−2−メトキシ−6−メチルフェニル}アゼチジン−1−イル)−2−メチルプロパンニトリル;
1−{1−[5−クロロ−4−フルオロ−2−メトキシ−3−(1−メチルアゼチジン−3−イル)フェニル]エチル}−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
5−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−2−フルオロ−3−[1−(2−ヒドロキシエチル)アゼチジン−3−イル]−4−メトキシベンゾニトリル;
5−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−3−{1−[(2R)−2−ヒドロキシプロピル]アゼチジン−3−イル}−4−メトキシ−2−メチルベンゾニトリル;
(2R)−2−[3−(3−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−5−シアノ−2−メトキシ−6−メチルフェニル)アゼチジン−1−イル]−N−メチルプロパンアミド;
1−{1−[5−クロロ−2−エトキシ−4−フルオロ−3−(1−メチルアゼチジン−3−イル)フェニル]エチル}−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
1−[3−(3−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−5−クロロ−2−エトキシ−6−フルオロフェニル)アゼチジン−1−イル]−2−メチルプロパン−2−オール;
(2S)−1−[3−(3−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−5−クロロ−2−エトキシ−6−フルオロフェニル)アゼチジン−1−イル]プロパン−2−オール;
(2R)−1−[3−(3−{1−[4−アミノ−3−(ジフルオロメチル)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル]エチル}−5−クロロ−2−エトキシ−6−フルオロフェニル)アゼチジン−1−イル]プロパン−2−オール;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−(1−メチルアゼチジン−3−イル)ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(2−ヒドロキシエチル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−{1−[(2S)−2−ヒドロキシプロピル]アゼチジン−3−イル}ベンゾニトリル;
tert−ブチル2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−エトキシフェニル}アゼチジン−1−イル)−2−メチルプロパノエート;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(2−ヒドロキシ−1,1−ジメチルエチル)アゼチジン−3−イル]ベンゾニトリル;
2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−エトキシフェニル}アゼチジン−1−イル)−2−メチルプロパンアミド;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(2−ヒドロキシ−2−メチルプロパノイル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−メトキシ−2−(1−メチルアゼチジン−3−イル)ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−[1−(2−ヒドロキシエチル)アゼチジン−3−イル]−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−{1−[(2S)−2−ヒドロキシプロピル]アゼチジン−3−イル}−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−[1−(2−ヒドロキシ−1−メチルエチル)アゼチジン−3−イル]−3−メトキシベンゾニトリル;
2−(1−アセチルアゼチジン−3−イル)−4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−メトキシ−2−[1−(メチルスルホニル)アゼチジン−3−イル]ベンゾニトリル;
メチル3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−メトキシフェニル}アゼチジン−1−カルボキシレート;
3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−メトキシフェニル}−N−(tert−ブチル)アゼチジン−1−カルボキサミド;
3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−メトキシフェニル}アゼチジン−1−カルボキサミド;
3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−メトキシフェニル}−N,N−ジメチルアゼチジン−1−カルボキサミド;
1−{1−[4,5−ジクロロ−3−(1−エチルアゼチジン−3−イル)−2−メトキシフェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
4−[1−(4−アミノ−5−メチル−7H−ピロロ[2,3−d]ピリミジン−7−イル)エチル]−6−クロロ−3−エトキシ−2−(1−イソプロピルアゼチジン−3−イル)ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−(1−エチルアゼチジン−3−イル)ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−(1−イソプロピルアゼチジン−3−イル)ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−(1−イソブチルアゼチジン−3−イル)ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−[1−(シクロプロピルメチル)アゼチジン−3−イル]−3−エトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−(1−シクロブチルアゼチジン−3−イル)−3−エトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−{1−[(2R)−2−ヒドロキシプロピル]アゼチジン−3−イル}ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(2−ヒドロキシ−2−メチルプロピル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(2−ヒドロキシ−1−メチルエチル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(2−メトキシエチル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−{1−[2−メトキシ−1−(メトキシメチル)エチル]アゼチジン−3−イル}ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(テトラヒドロフラン−3−イル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(テトラヒドロ−2H−ピラン−4−イル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(テトラヒドロフラン−3−イルメチル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(テトラヒドロ−2H−ピラン−4−イルメチル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(2,2,2−トリフルオロエチル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(3,3,3−トリフルオロプロピル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−[1−(シアノメチル)アゼチジン−3−イル]−3−エトキシベンゾニトリル;
エチル2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−エトキシフェニル}アゼチジン−1−イル)−2−メチルプロパノエート;
2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−エトキシフェニル}アゼチジン−1−イル)−N,2−ジメチルプロパンアミド;
2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−エトキシフェニル}アゼチジン−1−イル)−N,N,2−トリメチルプロパンアミド;
2−(1−アセチルアゼチジン−3−イル)−4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−(1−プロピオニルアゼチジン−3−イル)ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−(1−イソブチリルアゼチジン−3−イル)ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−[1−(2,2−ジメチルプロパノイル)アゼチジン−3−イル]−3−エトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−[1−(シクロプロピルカルボニル)アゼチジン−3−イル]−3−エトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(メチルスルホニル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(エチルスルホニル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(イソプロピルスルホニル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−[1−(シクロプロピルスルホニル)アゼチジン−3−イル]−3−エトキシベンゾニトリル;
メチル3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−エトキシフェニル}アゼチジン−1−カルボキシレート;
エチル3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−エトキシフェニル}アゼチジン−1−カルボキシレート;
イソプロピル3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−エトキシフェニル}アゼチジン−1−カルボキシレート;
3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−エトキシフェニル}−N−(tert−ブチル)アゼチジン−1−カルボキサミド;
3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−エトキシフェニル}アゼチジン−1−カルボキサミド;
3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−エトキシフェニル}−N−メチルアゼチジン−1−カルボキサミド;
3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−エトキシフェニル}−N−エチルアゼチジン−1−カルボキサミド;
3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−エトキシフェニル}−N,N−ジメチルアゼチジン−1−カルボキサミド;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−(1−エチルアゼチジン−3−イル)−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−(1−イソプロピルアゼチジン−3−イル)−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−(1−イソブチルアゼチジン−3−イル)−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−[1−(シクロプロピルメチル)アゼチジン−3−イル]−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−(1−シクロブチルアゼチジン−3−イル)−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−{1−[(2R)−2−ヒドロキシプロピル]アゼチジン−3−イル}−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−[1−(2−ヒドロキシ−2−メチルプロピル)アゼチジン−3−イル]−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−メトキシ−2−(1−オキセタン−3−イルアゼチジン−3−イル)ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−メトキシ−2−[1−(テトラヒドロフラン−3−イル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−メトキシ−2−[1−(テトラヒドロ−2H−ピラン−4−イル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−メトキシ−2−[1−(テトラヒドロフラン−3−イルメチル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−メトキシ−2−[1−(テトラヒドロ−2H−ピラン−4−イルメチル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−3−メトキシ−2−(1−プロピオニルアゼチジン−3−イル)ベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−(1−イソブチリルアゼチジン−3−イル)−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−[1−(シクロプロピルカルボニル)アゼチジン−3−イル]−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−[1−(エチルスルホニル)アゼチジン−3−イル]−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−[1−(イソプロピルスルホニル)アゼチジン−3−イル]−3−メトキシベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−6−クロロ−2−[1−(シクロプロピルスルホニル)アゼチジン−3−イル]−3−メトキシベンゾニトリル;
エチル3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−メトキシフェニル}アゼチジン−1−カルボキシレート;
イソプロピル3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−メトキシフェニル}アゼチジン−1−カルボキシレート;
3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−メトキシフェニル}−N−メチルアゼチジン−1−カルボキサミド;
3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5−クロロ−6−シアノ−2−メトキシフェニル}−N−エチルアゼチジン−1−カルボキサミド;
1−{1−[4,5−ジクロロ−3−(1−イソプロピルアゼチジン−3−イル)−2−メトキシフェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
2−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5,6−ジクロロ−2−メトキシフェニル}アゼチジン−1−イル)エタノール;
(2S)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5,6−ジクロロ−2−メトキシフェニル}アゼチジン−1−イル)プロパン−2−オール;
(2R)−1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5,6−ジクロロ−2−メトキシフェニル}アゼチジン−1−イル)プロパン−2−オール;
1−(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5,6−ジクロロ−2−メトキシフェニル}アゼチジン−1−イル)−2−メチルプロパン−2−オール;
1−{1−[4,5−ジクロロ−2−メトキシ−3−(1−オキセタン−3−イルアゼチジン−3−イル)フェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
(3−{3−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−5,6−ジクロロ−2−メトキシフェニル}アゼチジン−1−イル)アセトニトリル;
1−{1−[3−(1−アセチルアゼチジン−3−イル)−4,5−ジクロロ−2−メトキシフェニル]エチル}−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−4−アミン;
4−[1−(4−アミノ−5−メチル−7H−ピロロ[2,3−d]ピリミジン−7−イル)エチル]−6−クロロ−3−エトキシ−2−[1−(2−ヒドロキシエチル)アゼチジン−3−イル]ベンゾニトリル;
4−[1−(4−アミノ−5−メチル−7H−ピロロ[2,3−d]ピリミジン−7−イル)エチル]−6−クロロ−3−エトキシ−2−{1−[(2S)−2−ヒドロキシプロピル]アゼチジン−3−イル}ベンゾニトリル;
4−[−1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−2−{1−[(2S)−2−ヒドロキシプロピル]アゼチジン−3−イル}−3−メトキシ−6−メチルベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−3−エトキシ−2−(1−イソプロピルアゼチジン−3−イル)−6−メチルベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−3−エトキシ−2−[1−(2−ヒドロキシ−2−メチルプロピル)アゼチジン−3−イル]−6−メチルベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−3−エトキシ−2−[1−(2−ヒドロキシ−2−メチルプロパノイル)アゼチジン−3−イル]−6−メチルベンゾニトリル;
4−[1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−3−エトキシ−2−{1−[(2S)−2−ヒドロキシプロピル]アゼチジン−3−イル}−6−メチルベンゾニトリル;
4−[−1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−3−エトキシ−2−[1−(2−ヒドロキシエチル)アゼチジン−3−イル]−6−メチルベンゾニトリル;
4−[−1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル]−2−[1−(2−ヒドロキシ−2−メチルプロピル)アゼチジン−3−イル]−3−メトキシ−6−メチルベンゾニトリル;
4−(1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル)−6−クロロ−2−(1−(2−ヒドロキシプロピル)アゼチジン−3−イル)−3−メトキシベンゾニトリル;
4−((R)−1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル)−6−クロロ−2−(1−((S)−2−ヒドロキシプロピル)アゼチジン−3−イル)−3−メトキシベンゾニトリル;
4−((S)−1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル)−6−クロロ−2−(1−((R)−2−ヒドロキシプロピル)アゼチジン−3−イル)−3−メトキシベンゾニトリル;および
4−((R)−1−(4−アミノ−3−メチル−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)エチル)−6−クロロ−2−(1−((R)−2−ヒドロキシプロピル)アゼチジン−3−イル)−3−メトキシベンゾニトリル;
から選択される、請求項1に記載の化合物、または前述のもののいずれかの薬剤的に許容される塩。 - 請求項1〜18のいずれか1項に記載の化合物、またはその薬剤的に許容される塩、および少なくとも1つの薬剤的に許容される担体を含む、医薬組成物。
- PI3Kキナーゼの活性の阻害に用いるための医薬組成物であって、請求項1〜18のいずれか1項に記載の化合物、またはその薬剤的に許容される塩、および薬剤的に許容される担体を含む医薬組成物。
- 前記PI3Kが、PI3Kα、PI3Kβ、PI3Kδ、およびPI3Kγから成る群から選択される、請求項20に記載の医薬組成物。
- 前記PI3Kが変異を含む、請求項20に記載の医薬組成物。
- 前記化合物が、PI3Kα、PI3Kβ、およびPI3Kγのうちの1つまたは複数よりも、PI3Kδに対する選択的阻害剤である、請求項20〜22のいずれか1項に記載の医薬組成物。
- 患者の疾患を治療するための医薬組成物であって、請求項1〜18のいずれか1項に記載の化合物、またはその薬剤的に許容される塩、および薬剤的に許容される担体を含む医薬組成物。
- 前記疾患が、変形性関節症、再狭窄、アテローム性動脈硬化症、骨障害、関節炎、糖尿病性網膜症、乾癬、良性前立腺肥大、炎症、血管新生、膵炎、腎疾患、炎症性腸疾患、重症筋無力症、多発性硬化症、またはシェーグレン症候群である、請求項24に記載の医薬組成物。
- 前記化合物のうちの2つ以上が投与されるように用いられる、請求項24または25に記載の医薬組成物。
- 前記化合物がPI3Kキナーゼ以外のキナーゼを阻害するキナーゼ阻害剤と組み合わせて投与されるように用いられる、請求項25に記載の医薬組成物。
- 患者の免疫に基づく疾患を治療するための医薬組成物であって、請求項1〜18のいずれか1項に記載の化合物、またはその薬剤的に許容される塩、および薬剤的に許容される担体を含む医薬組成物。
- 前記免疫に基づく疾患が、関節リウマチ、アレルギー、喘息、糸球体腎炎、ループス、または前述のもののいずれかに関連する炎症である、請求項28に記載の医薬組成物。
- 患者の癌を治療するための医薬組成物であって、請求項1〜18のいずれか1項に記載の化合物、またはその薬剤的に許容される塩、および薬剤的に許容される担体を含む医薬組成物。
- 前記がんが、乳がん、前立腺がん、結腸がん、子宮内膜がん、脳がん、膀胱がん、皮膚がん、子宮がん、卵巣がん、肺がん、膵臓がん、腎臓がん、胃がん、または血液がんである、請求項30に記載の医薬組成物。
- 前記血液がんが、急性骨髄芽球性白血病、慢性骨髄性白血病、またはB細胞リンパ腫である、請求項31に記載の医薬組成物。
- 前記がんが、びまん性大細胞型B細胞リンパ腫である、請求項30に記載の医薬組成物。
- 患者の肺疾患を治療するための医薬組成物であって、請求項1〜18のいずれか1項に記載の化合物、またはその薬剤的に許容される塩、および薬剤的に許容される担体を含む医薬組成物。
- 前記肺疾患が、急性肺傷害(ALI)または成人呼吸窮迫症候群(ARDS)である、請求項34に記載の医薬組成物。
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2020
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2021
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2022
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