JP2014527959A5

JP2014527959A5 -

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Publication number: JP2014527959A5
Authority: JP; Japan
Prior art keywords: ethyl; methyl; pyrazolo; amino; pyrimidin
Prior art date: 2012-08-31
Legal status : Granted

Application number

JP2014528654A

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English (en)

Japanese (ja)

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JP2014527959A (ja

JP6067709B2 (ja

Filing date

2012-08-31

Publication date

2015-10-29

2012-08-31 Application filed filed Critical

2012-08-31 Priority claimed from PCT/US2012/053398 external-priority patent/WO2013033569A1/en

2014-10-23 Publication of JP2014527959A publication Critical patent/JP2014527959A/ja

2015-10-29 Publication of JP2014527959A5 publication Critical patent/JP2014527959A5/ja

2017-01-25 Application granted granted Critical

2017-01-25 Publication of JP6067709B2 publication Critical patent/JP6067709B2/ja

Status Active legal-status Critical Current

2032-08-31 Anticipated expiration legal-status Critical

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-1 —OH Chemical group 0.000 claims description 89
150000003839 salts Chemical class 0.000 claims description 77
150000001875 compounds Chemical class 0.000 claims description 70
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 52
125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 6
238000000034 method Methods 0.000 claims description 4
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 description 3
VJJSELYTDOGDNE-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n-(2-hydroxyethyl)-n-methylpyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=NC(C(=O)N(C)CCO)=C1 VJJSELYTDOGDNE-UHFFFAOYSA-N 0.000 claims description 3
CEECNMYKERBUGO-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)N=C1 CEECNMYKERBUGO-UHFFFAOYSA-N 0.000 claims description 3
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
OUELJXRVIBGBSC-UHFFFAOYSA-N 1-[1-[5-chloro-3-[1-(cyclopropylmethyl)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)=C1C(C1)CN1CC1CC1 OUELJXRVIBGBSC-UHFFFAOYSA-N 0.000 claims description 2
XFFQYSQURSCESP-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]ethanone Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(C)=O)C1 XFFQYSQURSCESP-UHFFFAOYSA-N 0.000 claims description 2
BXONZXFPKQOFNN-UHFFFAOYSA-N 2-[4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]pyrazol-1-yl]ethanol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C=1C=NN(CCO)C=1 BXONZXFPKQOFNN-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
GKLBWXFAKAOGRL-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=NC(C(=O)N(C)C)=C1 GKLBWXFAKAOGRL-UHFFFAOYSA-N 0.000 claims description 2
SMTNSBXQKKGWLV-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n-(2-hydroxyethyl)pyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=NC(C(=O)NCCO)=C1 SMTNSBXQKKGWLV-UHFFFAOYSA-N 0.000 claims description 2
SKAPLEFCLYIUAU-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(C=2C(=C(C(C)N3C4=NC=NC(N)=C4C(C)=N3)C=C(Cl)C=2C)OC)=C1 SKAPLEFCLYIUAU-UHFFFAOYSA-N 0.000 claims description 2
MICRYOZLKDGIIJ-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-iodopyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(I)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)N=C1 MICRYOZLKDGIIJ-UHFFFAOYSA-N 0.000 claims description 2
RYYHOGBWUDOVBW-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)N=C1 RYYHOGBWUDOVBW-UHFFFAOYSA-N 0.000 claims description 2
RCULREUPLKRTQM-UHFFFAOYSA-N 5-[3-[1-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C=C2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)N=C1 RCULREUPLKRTQM-UHFFFAOYSA-N 0.000 claims description 2
OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 152
125000005843 halogen group Chemical group 0.000 claims 88
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 57
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical group FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 50
125000003545 alkoxy group Chemical group 0.000 claims 48
229910052799 carbon Inorganic materials 0.000 claims 39
125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 31
125000001072 heteroaryl group Chemical group 0.000 claims 31
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 26
125000006601 (C1-C3) alkylcarbamyl group Chemical group 0.000 claims 23
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 23
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 22
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 22
239000008194 pharmaceutical composition Substances 0.000 claims 22
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 16
125000002947 alkylene group Chemical group 0.000 claims 14
125000004438 haloalkoxy group Chemical group 0.000 claims 13
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 12
125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 12
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
238000006467 substitution reaction Methods 0.000 claims 11
125000001424 substituent group Chemical group 0.000 claims 10
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 9
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 8
102000038030 PI3Ks Human genes 0.000 claims 8
108091007960 PI3Ks Proteins 0.000 claims 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 8
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 7
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 5
125000001188 haloalkyl group Chemical group 0.000 claims 5
125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
125000000753 cycloalkyl group Chemical group 0.000 claims 4
201000010099 disease Diseases 0.000 claims 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
125000004433 nitrogen atom Chemical group N* 0.000 claims 4
206010028980 Neoplasm Diseases 0.000 claims 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
201000011510 cancer Diseases 0.000 claims 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
125000003226 pyrazolyl group Chemical group 0.000 claims 3
125000000714 pyrimidinyl group Chemical group 0.000 claims 3
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 2
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
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims 2
125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims 2
125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims 2
125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims 2
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 2
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
ITEITQVKTJSFFX-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-(azetidin-3-yl)-6-chloro-3-ethoxybenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CNC1 ITEITQVKTJSFFX-UHFFFAOYSA-N 0.000 claims 2
NHMULOGKNRTRLR-UHFFFAOYSA-N 5-[3-[1-(4-amino-5-methylpyrrolo[2,3-d]pyrimidin-7-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=C2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)N=C1 NHMULOGKNRTRLR-UHFFFAOYSA-N 0.000 claims 2
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
206010061218 Inflammation Diseases 0.000 claims 2
208000019693 Lung disease Diseases 0.000 claims 2
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
206010069351 acute lung injury Diseases 0.000 claims 2
208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
125000003342 alkenyl group Chemical group 0.000 claims 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
125000000304 alkynyl group Chemical group 0.000 claims 2
125000002393 azetidinyl group Chemical group 0.000 claims 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
230000004054 inflammatory process Effects 0.000 claims 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
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
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
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
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
125000006599 (C1-C3) alkylaminocarbonylamino group Chemical group 0.000 claims 1
125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims 1
HQAMOZRQWZASAO-UHFFFAOYSA-N 1-[1-(5-chloro-2-methoxy-4-methyl-3-pyrimidin-5-ylphenyl)ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical class COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CN=CN=C1 HQAMOZRQWZASAO-UHFFFAOYSA-N 0.000 claims 1
OMMRWLRXHDDLKE-UHFFFAOYSA-N 1-[1-(5-chloro-3-cyclopropyl-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)=C1C1CC1 OMMRWLRXHDDLKE-UHFFFAOYSA-N 0.000 claims 1
BVQAEDIHXWMDRJ-UHFFFAOYSA-N 1-[1-[3-(2-aminopyrimidin-5-yl)-5-chloro-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)=C1C1=CN=C(N)N=C1 BVQAEDIHXWMDRJ-UHFFFAOYSA-N 0.000 claims 1
VBCPGZBXELQVJW-UHFFFAOYSA-N 1-[1-[3-(6-aminopyridin-3-yl)-5-chloro-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)=C1C1=CC=C(N)N=C1 VBCPGZBXELQVJW-UHFFFAOYSA-N 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
QQLYWGQNVSLCFL-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-3-(1-methylpiperidin-4-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)=C1C1CCN(C)CC1 QQLYWGQNVSLCFL-UHFFFAOYSA-N 0.000 claims 1
BWPVHVGKTKQLSR-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-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(C)=C1C1CN(C(C)C)C1 BWPVHVGKTKQLSR-UHFFFAOYSA-N 0.000 claims 1
VZUKFCYWZYFFIL-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-3-[1-(1-methylpiperidin-4-yl)pyrazol-4-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)C=NN1C1CCN(C)CC1 VZUKFCYWZYFFIL-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
QGPOJKNXFVJKMW-UHFFFAOYSA-N 1-[1-[5-chloro-3-(cyclopropylmethyl)-2-methoxy-4-methylphenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CC1=C(Cl)C=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C(OC)=C1CC1CC1 QGPOJKNXFVJKMW-UHFFFAOYSA-N 0.000 claims 1
BGAUCVBAAUHEDE-UHFFFAOYSA-N 1-[1-[5-chloro-3-[1-(1-fluoropropan-2-yl)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(C(C)CF)C1 BGAUCVBAAUHEDE-UHFFFAOYSA-N 0.000 claims 1
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
YPLUJLSBEXFVAU-UHFFFAOYSA-N 1-[1-[5-chloro-3-[1-[2-(dimethylamino)ethyl]pyrazol-4-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)=C1C=1C=NN(CCN(C)C)C=1 YPLUJLSBEXFVAU-UHFFFAOYSA-N 0.000 claims 1
VSAZWRHMIUNBII-UHFFFAOYSA-N 1-[1-[5-chloro-4-fluoro-2-methoxy-3-(1-methylazetidin-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)C1 VSAZWRHMIUNBII-UHFFFAOYSA-N 0.000 claims 1
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
MBAFAGVCOYZNOX-UHFFFAOYSA-N 1-[3-[3-[1-(4-amino-3-methylpyrazolo[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)=N2)C=C(Cl)C(F)=C1C1CN(CC(C)(C)O)C1 MBAFAGVCOYZNOX-UHFFFAOYSA-N 0.000 claims 1
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
GENAFRGLARHVMD-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]-2-hydroxy-2-methylpropan-1-one Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(=O)C(C)(C)O)C1 GENAFRGLARHVMD-UHFFFAOYSA-N 0.000 claims 1
PTFWTPFDLLZEPS-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]-2-methylpropan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CC(C)(C)O)C1 PTFWTPFDLLZEPS-UHFFFAOYSA-N 0.000 claims 1
DADMXEXKGKFTTG-UHFFFAOYSA-N 1-[3-[3-[1-[4-amino-3-(difluoromethyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-2-ethoxy-4-fluorophenyl]azetidin-1-yl]-2-methylpropan-2-ol Chemical compound CCOC1=C(C(=C(C=C1C2CN(C2)CC(C)(C)O)Cl)F)C(C)N3C4=NC=NC(=C4C(=N3)C(F)F)N DADMXEXKGKFTTG-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
HEQBQJMVHVFQFC-UHFFFAOYSA-N 1-[4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]piperidin-1-yl]-2-methylpropan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CCN(CC(C)(C)O)CC1 HEQBQJMVHVFQFC-UHFFFAOYSA-N 0.000 claims 1
IVERYMYYCPUGDS-UHFFFAOYSA-N 1-[4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]pyridin-2-yl]azetidin-3-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(C=1)=CC=NC=1N1CC(O)C1 IVERYMYYCPUGDS-UHFFFAOYSA-N 0.000 claims 1
WPJDICFYMRHROM-UHFFFAOYSA-N 1-[4-[4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]pyrazol-1-yl]piperidin-1-yl]ethanone Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(=C1)C=NN1C1CCN(C(C)=O)CC1 WPJDICFYMRHROM-UHFFFAOYSA-N 0.000 claims 1
MQKXQTKJRRACPT-UHFFFAOYSA-N 1-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-ethoxyphenyl]azetidine-3-carbonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1N1CC(C#N)C1 MQKXQTKJRRACPT-UHFFFAOYSA-N 0.000 claims 1
ROKNAOOYXYQMEU-UHFFFAOYSA-N 1-[5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]pyridine-3-carbonyl]azetidine-3-carbonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(C=1)=CN=CC=1C(=O)N1CC(C#N)C1 ROKNAOOYXYQMEU-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
TUEGHGDQSFFJCR-UHFFFAOYSA-N 2-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]acetonitrile Chemical compound COC1=C(CC#N)C(C)=C(Cl)C=C1C(C)N1C2=NC=NC(N)=C2C(C)=N1 TUEGHGDQSFFJCR-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
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
MWWOYWLTFYQTPP-UHFFFAOYSA-N 2-[3-[3-[1-[4-amino-3-(1H-pyrazol-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=CNN=C3)=N2)C=C(Cl)C(C)=C1C1CN(CC#N)C1 MWWOYWLTFYQTPP-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
JBDVKCGETSVNRB-UHFFFAOYSA-N 2-[4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]pyrazol-1-yl]-n,n-dimethylacetamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C=1C=NN(CC(=O)N(C)C)C=1 JBDVKCGETSVNRB-UHFFFAOYSA-N 0.000 claims 1
XOCBICZFWUYTBH-UHFFFAOYSA-N 2-[4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]pyrazol-1-yl]-n-methylacetamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C=1C=NN(CC(=O)NC)C=1 XOCBICZFWUYTBH-UHFFFAOYSA-N 0.000 claims 1
CTMFIZNSBDRCIE-UHFFFAOYSA-N 2-[4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]pyrazol-1-yl]acetamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C=1C=NN(CC(N)=O)C=1 CTMFIZNSBDRCIE-UHFFFAOYSA-N 0.000 claims 1
CLDPAHDXVKDZMW-UHFFFAOYSA-N 2-[4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]pyrazol-1-yl]-n,n-dimethylacetamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C=1C=NN(CC(=O)N(C)C)C=1 CLDPAHDXVKDZMW-UHFFFAOYSA-N 0.000 claims 1
FUDAFSSREATLEE-UHFFFAOYSA-N 2-[4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]pyrazol-1-yl]-n,n-dimethylpropanamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C=1C=NN(C(C)C(=O)N(C)C)C=1 FUDAFSSREATLEE-UHFFFAOYSA-N 0.000 claims 1
VZCBKGOVKCOFDS-UHFFFAOYSA-N 2-[5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]pyridin-2-yl]oxyethanol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(OCCO)N=C1 VZCBKGOVKCOFDS-UHFFFAOYSA-N 0.000 claims 1
UXTGQWWQMSXIHY-UHFFFAOYSA-N 2-[[5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]pyridin-2-yl]amino]ethanol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(NCCO)N=C1 UXTGQWWQMSXIHY-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
ZXJQEONXJODXNF-UHFFFAOYSA-N 3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-(3,5-difluorophenyl)-n-ethyl-6-methylbenzamide Chemical compound CCNC(=O)C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1C1=CC(F)=CC(F)=C1 ZXJQEONXJODXNF-UHFFFAOYSA-N 0.000 claims 1
FCDNPSKPJCDICB-UHFFFAOYSA-N 3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylbenzonitrile Chemical compound C1=C(Cl)C(C)=C(C#N)C(OCC)=C1C(C)N1C2=NC=NC(N)=C2C(C)=N1 FCDNPSKPJCDICB-UHFFFAOYSA-N 0.000 claims 1
QOMSHSGBNJTTBF-UHFFFAOYSA-N 3-[1-[4-amino-3-(1H-pyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-2-ethoxy-N-ethyl-6-methylbenzamide Chemical compound CCNC(=O)C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C3=CNN=C3)=N2)=C1OCC QOMSHSGBNJTTBF-UHFFFAOYSA-N 0.000 claims 1
YBSVOGCAZYSWOK-UHFFFAOYSA-N 3-[1-[4-amino-3-(1h-indazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-2-ethoxy-n-ethyl-6-methylbenzamide Chemical compound CCNC(=O)C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C=3C=C4NN=CC4=CC=3)=N2)=C1OCC YBSVOGCAZYSWOK-UHFFFAOYSA-N 0.000 claims 1
GKAAKWJWBZKIGE-UHFFFAOYSA-N 3-[1-[4-amino-3-(1h-indol-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-2-ethoxy-n-ethyl-6-methylbenzamide Chemical compound CCNC(=O)C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C=3C=C4C=CNC4=CC=3)=N2)=C1OCC GKAAKWJWBZKIGE-UHFFFAOYSA-N 0.000 claims 1
WMARVFKDNUJMDW-UHFFFAOYSA-N 3-[1-[4-amino-3-(1h-pyrrolo[2,3-b]pyridin-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-2-ethoxy-n-ethyl-6-methylbenzamide Chemical compound CCNC(=O)C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C=3C=C4C=CNC4=NC=3)=N2)=C1OCC WMARVFKDNUJMDW-UHFFFAOYSA-N 0.000 claims 1
IBBUVKWTSDSITE-UHFFFAOYSA-N 3-[1-[4-amino-3-(2-amino-1,3-benzothiazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-2-ethoxy-n-ethyl-6-methylbenzamide Chemical compound CCNC(=O)C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C=3C=C4SC(N)=NC4=CC=3)=N2)=C1OCC IBBUVKWTSDSITE-UHFFFAOYSA-N 0.000 claims 1
GMVYOEGUJRBUSS-UHFFFAOYSA-N 3-[1-[4-amino-3-(2-amino-1,3-benzoxazol-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-2-ethoxy-n-ethyl-6-methylbenzamide Chemical compound CCNC(=O)C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C=3C=C4N=C(N)OC4=CC=3)=N2)=C1OCC GMVYOEGUJRBUSS-UHFFFAOYSA-N 0.000 claims 1
RJDWLJPCXGVXSN-UHFFFAOYSA-N 3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylpropanamide Chemical compound C1=C(Cl)C(C)=C(CCC(=O)N(C)C)C(OC)=C1C(C)N1C2=NC=NC(N)=C2C(C)=N1 RJDWLJPCXGVXSN-UHFFFAOYSA-N 0.000 claims 1
GOLQSWXUIZQBOS-UHFFFAOYSA-N 3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]cyclobutan-1-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CC(O)C1 GOLQSWXUIZQBOS-UHFFFAOYSA-N 0.000 claims 1
DGQJWGJTTFCTAE-UHFFFAOYSA-N 3-[3-[1-(4-amino-5-oxopyrido[2,3-d]pyrimidin-8-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylbenzamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(=O)C=C2)C=C(Cl)C(C)=C1C1=CC=CC(C(=O)N(C)C)=C1 DGQJWGJTTFCTAE-UHFFFAOYSA-N 0.000 claims 1
GWTTVTZZVDBTMB-UHFFFAOYSA-N 3-[3-[1-(4-amino-5-oxopyrido[2,3-d]pyrimidin-8-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylbenzenesulfonamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(=O)C=C2)C=C(Cl)C(C)=C1C1=CC=CC(S(=O)(=O)N(C)C)=C1 GWTTVTZZVDBTMB-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
HHFHPZCNCGRYSA-UHFFFAOYSA-N 3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-ethoxyphenyl]-n-ethylazetidine-1-carboxamide Chemical compound C1N(C(=O)NCC)CC1C1=C(OCC)C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=CC(Cl)=C1C#N HHFHPZCNCGRYSA-UHFFFAOYSA-N 0.000 claims 1
YQNXBWCPBPPQNG-UHFFFAOYSA-N 3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-ethoxyphenyl]-n-methylazetidine-1-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(=O)NC)C1 YQNXBWCPBPPQNG-UHFFFAOYSA-N 0.000 claims 1
HIAUIXOCSLFPKP-UHFFFAOYSA-N 3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-ethoxyphenyl]-n-tert-butylazetidine-1-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(=O)NC(C)(C)C)C1 HIAUIXOCSLFPKP-UHFFFAOYSA-N 0.000 claims 1
FRRSLHDFEVZTPH-UHFFFAOYSA-N 3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-methoxyphenyl]-n,n-dimethylazetidine-1-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(=O)N(C)C)C1 FRRSLHDFEVZTPH-UHFFFAOYSA-N 0.000 claims 1
XIWFPOJEHQXANW-UHFFFAOYSA-N 3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-methoxyphenyl]-n-ethylazetidine-1-carboxamide Chemical compound C1N(C(=O)NCC)CC1C1=C(OC)C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=CC(Cl)=C1C#N XIWFPOJEHQXANW-UHFFFAOYSA-N 0.000 claims 1
VUHLYNMOPZYTEK-UHFFFAOYSA-N 3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-methoxyphenyl]-n-methylazetidine-1-carboxamide Chemical compound C1N(C(=O)NC)CC1C1=C(OC)C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=CC(Cl)=C1C#N VUHLYNMOPZYTEK-UHFFFAOYSA-N 0.000 claims 1
NGSFHDXBDLNNPM-UHFFFAOYSA-N 3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-methoxyphenyl]-n-tert-butylazetidine-1-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(=O)NC(C)(C)C)C1 NGSFHDXBDLNNPM-UHFFFAOYSA-N 0.000 claims 1
MJVXTRGIJKQFHG-UHFFFAOYSA-N 3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-methoxyphenyl]azetidine-1-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(N)=O)C1 MJVXTRGIJKQFHG-UHFFFAOYSA-N 0.000 claims 1
XGARCYYYFPWMKC-IAPIXIRKSA-N 4-[(1R)-1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-(2-oxo-1,3-oxazolidin-5-yl)benzonitrile Chemical compound CCOc1c(cc(Cl)c(C#N)c1C1CNC(=O)O1)[C@@H](C)n1nc(C)c2c(N)ncnc12 XGARCYYYFPWMKC-IAPIXIRKSA-N 0.000 claims 1
PJXOQIHPWFBWNB-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-(azetidin-3-yl)-6-chloro-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CNC1 PJXOQIHPWFBWNB-UHFFFAOYSA-N 0.000 claims 1
VMEDCGGYYKALPX-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-[1-(2-hydroxy-2-methylpropyl)azetidin-3-yl]-3-methoxy-6-methylbenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C)C(C#N)=C1C1CN(CC(C)(C)O)C1 VMEDCGGYYKALPX-UHFFFAOYSA-N 0.000 claims 1
PNRYWUJRDIJNKG-CFMCSPIPSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-[1-[(2s)-2-hydroxypropyl]azetidin-3-yl]-3-methoxy-6-methylbenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C)C(C#N)=C1C1CN(C[C@H](C)O)C1 PNRYWUJRDIJNKG-CFMCSPIPSA-N 0.000 claims 1
NDKDVJVSBLWXFS-QBRMTTIGSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-chloro-1,4,5,6-tetradeuterio-6-[1-(2-hydroxyethyl)azetidin-3-yl]-5-methoxycyclohex-2-ene-1-carbonitrile Chemical compound NC1=C2C(=NC=N1)N(N=C2C)C(C)C1(C(C(C(C#N)(C(=C1)Cl)[2H])(C1CN(C1)CCO)[2H])(OC)[2H])[2H] NDKDVJVSBLWXFS-QBRMTTIGSA-N 0.000 claims 1
GRMHNISBQAWILC-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-ethoxy-2-[1-(2-hydroxyethyl)azetidin-3-yl]-6-methylbenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C)C(C#N)=C1C1CN(CCO)C1 GRMHNISBQAWILC-UHFFFAOYSA-N 0.000 claims 1
XBKSABZOJVXHRZ-LBAUFKAWSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-ethoxy-2-[1-[(2s)-2-hydroxypropyl]azetidin-3-yl]-6-methylbenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C)C(C#N)=C1C1CN(C[C@H](C)O)C1 XBKSABZOJVXHRZ-LBAUFKAWSA-N 0.000 claims 1
BIWLMIRVKBSFQI-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-ethoxy-6-methyl-2-(1-methylpyrazol-4-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C)C(C#N)=C1C=1C=NN(C)C=1 BIWLMIRVKBSFQI-UHFFFAOYSA-N 0.000 claims 1
IECAGZBMWJQJMS-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-ethoxy-6-methyl-2-(1-propan-2-ylazetidin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C)C(C#N)=C1C1CN(C(C)C)C1 IECAGZBMWJQJMS-UHFFFAOYSA-N 0.000 claims 1
ZZVHFNRZGOZYJV-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-ethoxy-6-methyl-2-(5-methylsulfonylpyridin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C)C(C#N)=C1C1=CN=CC(S(C)(=O)=O)=C1 ZZVHFNRZGOZYJV-UHFFFAOYSA-N 0.000 claims 1
CWLGWANCAOKWDL-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-methoxy-6-methyl-2-(5-methylsulfonylpyridin-3-yl)benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C)C(C#N)=C1C1=CN=CC(S(C)(=O)=O)=C1 CWLGWANCAOKWDL-UHFFFAOYSA-N 0.000 claims 1
QUCHHODLYZYMGC-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-(1-cyclobutylazetidin-3-yl)-3-ethoxybenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C(C1)CN1C1CCC1 QUCHHODLYZYMGC-UHFFFAOYSA-N 0.000 claims 1
OUIMJCJSIBATHP-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-(1-cyclobutylazetidin-3-yl)-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C(C1)CN1C1CCC1 OUIMJCJSIBATHP-UHFFFAOYSA-N 0.000 claims 1
JXFZARSQFWWJBT-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-(1-cyclopropylsulfonylazetidin-3-yl)-3-ethoxybenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C(C1)CN1S(=O)(=O)C1CC1 JXFZARSQFWWJBT-UHFFFAOYSA-N 0.000 claims 1
IDJJUXQCGFEEMS-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-(1-cyclopropylsulfonylazetidin-3-yl)-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C(C1)CN1S(=O)(=O)C1CC1 IDJJUXQCGFEEMS-UHFFFAOYSA-N 0.000 claims 1
PBCQWOSTPCTHRD-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-(1-ethylazetidin-3-yl)-3-methoxybenzonitrile Chemical compound C1N(CC)CC1C1=C(OC)C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=CC(Cl)=C1C#N PBCQWOSTPCTHRD-UHFFFAOYSA-N 0.000 claims 1
SAUFCGVJPPRKTQ-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-(1-ethylsulfonylazetidin-3-yl)-3-methoxybenzonitrile Chemical compound C1N(S(=O)(=O)CC)CC1C1=C(OC)C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=CC(Cl)=C1C#N SAUFCGVJPPRKTQ-UHFFFAOYSA-N 0.000 claims 1
SZGPIMCGZNYFKO-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-[1-(1,3-dimethoxypropan-2-yl)azetidin-3-yl]-3-ethoxybenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(COC)COC)C1 SZGPIMCGZNYFKO-UHFFFAOYSA-N 0.000 claims 1
ZYYBPQOUQVKJNI-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-[1-(2-hydroxyethyl)azetidin-3-yl]-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(CCO)C1 ZYYBPQOUQVKJNI-UHFFFAOYSA-N 0.000 claims 1
OLGYOFLRVGHHNU-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-[1-(cyanomethyl)azetidin-3-yl]-3-ethoxybenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(CC#N)C1 OLGYOFLRVGHHNU-UHFFFAOYSA-N 0.000 claims 1
UDNTZJAIECMPIP-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-[1-(cyclopropanecarbonyl)azetidin-3-yl]-3-ethoxybenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C(C1)CN1C(=O)C1CC1 UDNTZJAIECMPIP-UHFFFAOYSA-N 0.000 claims 1
VVGLINSIWVCUJU-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-[1-(cyclopropanecarbonyl)azetidin-3-yl]-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C(C1)CN1C(=O)C1CC1 VVGLINSIWVCUJU-UHFFFAOYSA-N 0.000 claims 1
FGFDUYXZAAZWEP-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-[1-(cyclopropylmethyl)azetidin-3-yl]-3-ethoxybenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C(C1)CN1CC1CC1 FGFDUYXZAAZWEP-UHFFFAOYSA-N 0.000 claims 1
DHMAUKKOJFKQKU-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-[1-(cyclopropylmethyl)azetidin-3-yl]-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C(C1)CN1CC1CC1 DHMAUKKOJFKQKU-UHFFFAOYSA-N 0.000 claims 1
KLKCQNBHXXLCHY-JTDNENJMSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-[1-[(2r)-2-hydroxypropyl]azetidin-3-yl]-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C[C@@H](C)O)C1 KLKCQNBHXXLCHY-JTDNENJMSA-N 0.000 claims 1
KLKCQNBHXXLCHY-AMGKYWFPSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-[1-[(2s)-2-hydroxypropyl]azetidin-3-yl]-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C[C@H](C)O)C1 KLKCQNBHXXLCHY-AMGKYWFPSA-N 0.000 claims 1
LSKQFKWRGIDVRW-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-(1-ethylazetidin-3-yl)benzonitrile 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
SWUXBCAWGABMGD-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-(1-ethylsulfonylazetidin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(S(=O)(=O)CC)C1 SWUXBCAWGABMGD-UHFFFAOYSA-N 0.000 claims 1
VXDSZRICEQLKCZ-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-(1-methylazetidin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C)C1 VXDSZRICEQLKCZ-UHFFFAOYSA-N 0.000 claims 1
MCRIWRBTFCRQSY-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-(1-methylsulfonylazetidin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(S(C)(=O)=O)C1 MCRIWRBTFCRQSY-UHFFFAOYSA-N 0.000 claims 1
DCXZAUPQMHJQEK-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-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)=N2)C=C(Cl)C(C#N)=C1C1CN(C(C)C)C1 DCXZAUPQMHJQEK-UHFFFAOYSA-N 0.000 claims 1
GNKXJUPRROBESG-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-(1-propan-2-ylsulfonylazetidin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(S(=O)(=O)C(C)C)C1 GNKXJUPRROBESG-UHFFFAOYSA-N 0.000 claims 1
FZASTEUHBGGYAL-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-(3-methoxyazetidin-1-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1N1CC(OC)C1 FZASTEUHBGGYAL-UHFFFAOYSA-N 0.000 claims 1
GZMKBXXTFROUMP-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-(5-methylsulfonylpyridin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1=CN=CC(S(C)(=O)=O)=C1 GZMKBXXTFROUMP-UHFFFAOYSA-N 0.000 claims 1
IIEKNYURGTYVMT-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-(5-oxopyrrolidin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CNC(=O)C1 IIEKNYURGTYVMT-UHFFFAOYSA-N 0.000 claims 1
LHOWBTROKICTRB-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-[1-(2,2,2-trifluoroethyl)azetidin-3-yl]benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(CC(F)(F)F)C1 LHOWBTROKICTRB-UHFFFAOYSA-N 0.000 claims 1
NTWMOEJWTRHNIB-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-[1-(2-methylpropanoyl)azetidin-3-yl]benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(=O)C(C)C)C1 NTWMOEJWTRHNIB-UHFFFAOYSA-N 0.000 claims 1
BIXUEAVGWAHQLE-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-[1-(2-methylpropyl)azetidin-3-yl]benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(CC(C)C)C1 BIXUEAVGWAHQLE-UHFFFAOYSA-N 0.000 claims 1
BDDZANHGMPZWSJ-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-[1-(3,3,3-trifluoropropyl)azetidin-3-yl]benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(CCC(F)(F)F)C1 BDDZANHGMPZWSJ-UHFFFAOYSA-N 0.000 claims 1
DXGKJGAEYCAZJU-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-[1-(oxan-4-ylmethyl)azetidin-3-yl]benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C(C1)CN1CC1CCOCC1 DXGKJGAEYCAZJU-UHFFFAOYSA-N 0.000 claims 1
MCIRQIFXNINZHL-PUODRLBUSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-[1-[(2r)-2-hydroxypropyl]azetidin-3-yl]benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C[C@@H](C)O)C1 MCIRQIFXNINZHL-PUODRLBUSA-N 0.000 claims 1
MCIRQIFXNINZHL-NBFOIZRFSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-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)=N2)C=C(Cl)C(C#N)=C1C1CN(C[C@H](C)O)C1 MCIRQIFXNINZHL-NBFOIZRFSA-N 0.000 claims 1
RTIFIPCKKIJSKD-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-[3-(methoxymethyl)azetidin-1-yl]benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1N1CC(COC)C1 RTIFIPCKKIJSKD-UHFFFAOYSA-N 0.000 claims 1
HLNPCHVPPSSFJF-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-[5-(1,3-oxazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C(C=1)=CN=CC=1C1=NC=CO1 HLNPCHVPPSSFJF-UHFFFAOYSA-N 0.000 claims 1
ZVKBFCGBELOHKY-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-pyrimidin-5-ylbenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1=CN=CN=C1 ZVKBFCGBELOHKY-UHFFFAOYSA-N 0.000 claims 1
GZPOZNLKRAMBLT-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-pyrrolidin-1-ylbenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1N1CCCC1 GZPOZNLKRAMBLT-UHFFFAOYSA-N 0.000 claims 1
DBKSCUIVQFGLEJ-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxy-2-(1-methylazetidin-3-yl)benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C)C1 DBKSCUIVQFGLEJ-UHFFFAOYSA-N 0.000 claims 1
OWQMJTFVVTZJKY-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxy-2-(1-methylsulfonylazetidin-3-yl)benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(S(C)(=O)=O)C1 OWQMJTFVVTZJKY-UHFFFAOYSA-N 0.000 claims 1
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
RHNYPRNOZDCEDY-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxy-2-(5-methylsulfonylpyridin-3-yl)benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1=CN=CC(S(C)(=O)=O)=C1 RHNYPRNOZDCEDY-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
YQOCDMFKKLHYAU-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxy-2-[1-(2-methylpropyl)azetidin-3-yl]benzonitrile 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
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
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
MPNWWLXSJKXPKN-UHFFFAOYSA-N 4-[1-(4-amino-5-oxopyrido[2,3-d]pyrimidin-8-yl)ethyl]-6-chloro-3-ethoxy-2-(5-methylsulfonylpyridin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(=O)C=C2)C=C(Cl)C(C#N)=C1C1=CN=CC(S(C)(=O)=O)=C1 MPNWWLXSJKXPKN-UHFFFAOYSA-N 0.000 claims 1
UCYDWQYLQRHHCX-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]-1,3-oxazolidin-2-one Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1COC(=O)N1 UCYDWQYLQRHHCX-UHFFFAOYSA-N 0.000 claims 1
ZQPDJCIXJHUERQ-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]pyrrolidin-2-one Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CNC(=O)C1 ZQPDJCIXJHUERQ-UHFFFAOYSA-N 0.000 claims 1
KLTDLHDMXSIRPS-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=NC(C(=O)N(C)C)=C1 KLTDLHDMXSIRPS-UHFFFAOYSA-N 0.000 claims 1
NXXMPAIOHBNOPP-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]pyrrolidin-2-one Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CNC(=O)C1 NXXMPAIOHBNOPP-UHFFFAOYSA-N 0.000 claims 1
DCYPFCXQPSHQAV-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-2-fluoro-n,n-dimethylbenzamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)C(F)=C1 DCYPFCXQPSHQAV-UHFFFAOYSA-N 0.000 claims 1
NJMVVKSDTMRUPW-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-2-fluoro-n-methylbenzamide Chemical compound C1=C(F)C(C(=O)NC)=CC=C1C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1OC NJMVVKSDTMRUPW-UHFFFAOYSA-N 0.000 claims 1
CGOOTFVIDYUBGF-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-cyano-2-methoxy-6-methylphenyl]-n-(2-hydroxyethyl)-n-methylpyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C#N)C(C)=C1C1=CC=NC(C(=O)N(C)CCO)=C1 CGOOTFVIDYUBGF-UHFFFAOYSA-N 0.000 claims 1
KPNNLKLNEVRVPW-UHFFFAOYSA-N 4-[3-[1-(4-aminopyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C=N2)C=C(Cl)C(C)=C1C1=CC=NC(C(=O)N(C)C)=C1 KPNNLKLNEVRVPW-UHFFFAOYSA-N 0.000 claims 1
GFUWVUDUTZFZLS-UHFFFAOYSA-N 4-[3-[1-(4-aminopyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n-(2-hydroxyethyl)pyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C=N2)C=C(Cl)C(C)=C1C1=CC=NC(C(=O)NCCO)=C1 GFUWVUDUTZFZLS-UHFFFAOYSA-N 0.000 claims 1
WKZWNOVBZGKRGR-UHFFFAOYSA-N 4-[3-[1-[(6-amino-5-ethanimidoylpyrimidin-4-yl)amino]ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound COC1=C(C(C)NC=2C(=C(N)N=CN=2)C(C)=N)C=C(Cl)C(C)=C1C1=CC=NC(C(=O)N(C)C)=C1 WKZWNOVBZGKRGR-UHFFFAOYSA-N 0.000 claims 1
DWHGOGVUELEDRG-UHFFFAOYSA-N 4-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-cyano-6-ethoxy-3-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C)C(C#N)=C1C1=CC=NC(C(=O)N(C)C)=C1 DWHGOGVUELEDRG-UHFFFAOYSA-N 0.000 claims 1
ZIMNJKKNCVHWOV-UHFFFAOYSA-N 4-amino-8-[1-(5-chloro-2-methoxy-4-methyl-3-pyridin-3-ylphenyl)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)=C1C1=CC=CN=C1 ZIMNJKKNCVHWOV-UHFFFAOYSA-N 0.000 claims 1
UGMJKNBAEHXEAV-UHFFFAOYSA-N 4-amino-8-[1-(5-chloro-2-methoxy-4-methyl-3-pyrimidin-5-ylphenyl)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)=C1C1=CN=CN=C1 UGMJKNBAEHXEAV-UHFFFAOYSA-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
TVKCMRJHVAKGBR-UHFFFAOYSA-N 4-amino-8-[1-[5-chloro-2-methoxy-4-methyl-3-(5-methylsulfonylpyridin-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)=C1C1=CN=CC(S(C)(=O)=O)=C1 TVKCMRJHVAKGBR-UHFFFAOYSA-N 0.000 claims 1
NLHXYFCSZPHVIO-UHFFFAOYSA-N 5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-4-ethoxy-2-methyl-3-(1-methylpyrazol-4-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C#N)C(C)=C1C=1C=NN(C)C=1 NLHXYFCSZPHVIO-UHFFFAOYSA-N 0.000 claims 1
PFWHUFUHASEOFP-UHFFFAOYSA-N 5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-4-methoxy-2-methyl-3-(1-methylpyrazol-4-yl)benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C#N)C(C)=C1C=1C=NN(C)C=1 PFWHUFUHASEOFP-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
JAOSUCRDSSWHBL-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-cyanopyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C#N)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)N=C1 JAOSUCRDSSWHBL-UHFFFAOYSA-N 0.000 claims 1
RRSCRMHZMWUSFN-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-cyclopropylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C3CC3)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)N=C1 RRSCRMHZMWUSFN-UHFFFAOYSA-N 0.000 claims 1
LWRCOZZUEDSSRB-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-ethylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(CC)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)N=C1 LWRCOZZUEDSSRB-UHFFFAOYSA-N 0.000 claims 1
ZOAQLRLXOXZODI-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-(2,2-difluoroethoxy)-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.N1=C(C)C2=C(N)N=CN=C2N1C(C)C(C=1OCC(F)F)=CC(Cl)=C(C)C=1C1=CC=C(C(=O)N(C)C)N=C1 ZOAQLRLXOXZODI-UHFFFAOYSA-N 0.000 claims 1
NENZZUFAAHFIPT-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]-1,3-oxazolidin-2-one Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CNC(=O)O1 NENZZUFAAHFIPT-UHFFFAOYSA-N 0.000 claims 1
AAAFOWLNHPEWFZ-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)N=C1 AAAFOWLNHPEWFZ-UHFFFAOYSA-N 0.000 claims 1
KUXSPGMRBZLSSK-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]-n,n-dimethylpyridine-3-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CN=CC(C(=O)N(C)C)=C1 KUXSPGMRBZLSSK-UHFFFAOYSA-N 0.000 claims 1
SPDKDKKGRGWOLC-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]-n-methylpyridine-2-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)NC)N=C1 SPDKDKKGRGWOLC-UHFFFAOYSA-N 0.000 claims 1
NIZYKSCTQPOPRY-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-1,3-oxazolidin-2-one Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CNC(=O)O1 NIZYKSCTQPOPRY-UHFFFAOYSA-N 0.000 claims 1
KTVVAZSEWBIVSN-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)N=C1 KTVVAZSEWBIVSN-UHFFFAOYSA-N 0.000 claims 1
KATAAFRJKJMWFE-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylpyridine-3-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CN=CC(C(=O)N(C)C)=C1 KATAAFRJKJMWFE-UHFFFAOYSA-N 0.000 claims 1
VTLYUEQNHLTQGU-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n-(2-hydroxyethyl)-n-methylpyridine-3-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CN=CC(C(=O)N(C)CCO)=C1 VTLYUEQNHLTQGU-UHFFFAOYSA-N 0.000 claims 1
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ONBNCONPECJPDM-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1OC ONBNCONPECJPDM-UHFFFAOYSA-N 0.000 claims 1
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JP2014528654A 2011-09-02 2012-08-31 Ｐｉ３ｋ阻害剤としてのヘテロシクリルアミン Active JP6067709B2 (ja)