JP2019517548A5

JP2019517548A5 -

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Publication number: JP2019517548A5
Authority: JP; Japan
Prior art keywords: pyrimidin; methyl; diazaspiro; fluoro; oxy
Prior art date: 2017-06-08
Legal status : Granted

Application number

JP2018564288A

Other languages

English (en)

Japanese (ja)

Other versions

JP7007302B2 (ja

JP2019517548A (ja

Filing date

2017-06-08

Publication date

2020-07-27

2017-06-08 Application filed filed Critical

2017-06-08 Priority claimed from PCT/US2017/036506 external-priority patent/WO2017214367A1/en

2019-06-24 Publication of JP2019517548A publication Critical patent/JP2019517548A/ja

2020-07-27 Publication of JP2019517548A5 publication Critical patent/JP2019517548A5/ja

2022-01-06 Priority to JP2022000946A priority Critical patent/JP7461390B2/ja

2022-01-24 Application granted granted Critical

2022-01-24 Publication of JP7007302B2 publication Critical patent/JP7007302B2/ja

2024-01-04 Priority to JP2024000278A priority patent/JP2024045176A/ja

2025-05-19 Priority to JP2025083421A priority patent/JP2025113339A/ja

Status Active legal-status Critical Current

2037-06-08 Anticipated expiration legal-status Critical

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125000000217 alkyl group Chemical group 0.000 claims 36
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 29
-1 carboxy, aminocarbonyl Chemical group 0.000 claims 22
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 18
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 18
125000001475 halogen functional group Chemical group 0.000 claims 17
150000003839 salts Chemical class 0.000 claims 17
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 14
150000001875 compounds Chemical class 0.000 claims 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
125000001424 substituent group Chemical group 0.000 claims 13
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 12
125000000592 heterocycloalkyl group Chemical group 0.000 claims 12
WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims 12
XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 claims 12
125000003545 alkoxy group Chemical group 0.000 claims 11
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 10
125000002947 alkylene group Chemical group 0.000 claims 10
208000032839 leukemia Diseases 0.000 claims 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 8
125000000753 cycloalkyl group Chemical group 0.000 claims 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
125000003118 aryl group Chemical group 0.000 claims 6
229940047889 isobutyramide Drugs 0.000 claims 6
125000003282 alkyl amino group Chemical group 0.000 claims 5
229910052799 carbon Inorganic materials 0.000 claims 5
125000004966 cyanoalkyl group Chemical group 0.000 claims 5
125000004663 dialkyl amino group Chemical group 0.000 claims 5
229910052739 hydrogen Inorganic materials 0.000 claims 5
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 4
208000031261 Acute myeloid leukaemia Diseases 0.000 claims 4
201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 4
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 4
239000000203 mixture Substances 0.000 claims 4
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 3
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 3
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
206010025323 Lymphomas Diseases 0.000 claims 3
201000003793 Myelodysplastic syndrome Diseases 0.000 claims 3
208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 3
206010028980 Neoplasm Diseases 0.000 claims 3
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 3
201000011510 cancer Diseases 0.000 claims 3
125000004438 haloalkoxy group Chemical group 0.000 claims 3
125000001072 heteroaryl group Chemical group 0.000 claims 3
229910052757 nitrogen Inorganic materials 0.000 claims 3
125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 2
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 2
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims 2
MVZOVVZXFCEUTC-UHFFFAOYSA-N 2-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]-N-methylcyclopropane-1-carboxamide Chemical compound FC=1C=CC(=C(C=1)C1C(C1)C(=O)NC)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 MVZOVVZXFCEUTC-UHFFFAOYSA-N 0.000 claims 2
QOYHRGZPMQCFCB-UHFFFAOYSA-N 3-cyclopropyl-4-[3,5-difluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]benzonitrile Chemical compound C1(CC1)C1=C(C=CC(=C1)C#N)C1=C(C(=CC(=C1)F)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 QOYHRGZPMQCFCB-UHFFFAOYSA-N 0.000 claims 2
XEOOXZWSBPXOQM-UHFFFAOYSA-N 3-cyclopropyl-4-[5-fluoro-2-[4-[6-[(4-hydroxycyclohexyl)methyl]-2,6-diazaspiro[3.3]heptan-2-yl]pyrimidin-5-yl]oxyphenyl]benzonitrile Chemical compound C1(CC1)C1=C(C=CC(=C1)C#N)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(C1)CN(C2)CC1CCC(CC1)O XEOOXZWSBPXOQM-UHFFFAOYSA-N 0.000 claims 2
OEJLVIFKPXWYRF-UHFFFAOYSA-N 4-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]-3-methylbenzonitrile Chemical compound FC=1C=CC(=C(C=1)C1=C(C=C(C=C1)C#N)C)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 OEJLVIFKPXWYRF-UHFFFAOYSA-N 0.000 claims 2
UZWASOCNSBOGLD-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(2-methylpropyl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound CC(C)Cc1cc(F)ccc1Oc1cncnc1N1CCC2(CCN(Cc3ccc4[nH]c(=O)[nH]c4c3)C2)C1 UZWASOCNSBOGLD-UHFFFAOYSA-N 0.000 claims 2
GEUFTLVWVDBEQG-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 GEUFTLVWVDBEQG-UHFFFAOYSA-N 0.000 claims 2
LAKUYUKDMYWFOP-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[4-[7-[[4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC=C(C=C1)N1C(OCC1)=O LAKUYUKDMYWFOP-UHFFFAOYSA-N 0.000 claims 2
208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 2
208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 2
208000034578 Multiple myelomas Diseases 0.000 claims 2
208000014767 Myeloproliferative disease Diseases 0.000 claims 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
206010035226 Plasma cell myeloma Diseases 0.000 claims 2
208000033759 Prolymphocytic T-Cell Leukemia Diseases 0.000 claims 2
208000026651 T-cell prolymphocytic leukemia Diseases 0.000 claims 2
206010012601 diabetes mellitus Diseases 0.000 claims 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
125000005647 linker group Chemical group 0.000 claims 2
208000003747 lymphoid leukemia Diseases 0.000 claims 2
201000005962 mycosis fungoides Diseases 0.000 claims 2
208000025113 myeloid leukemia Diseases 0.000 claims 2
YRJCXPFMFZIXRI-UHFFFAOYSA-N nonan-3-amine Chemical compound CCCCCCC(N)CC YRJCXPFMFZIXRI-UHFFFAOYSA-N 0.000 claims 2
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 2
229910052760 oxygen Inorganic materials 0.000 claims 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
230000008707 rearrangement Effects 0.000 claims 2
208000008732 thymoma Diseases 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
LPYQMZPUGIQGLF-UHFFFAOYSA-N 1-[2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]-2-methylpropan-2-ol Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC(C)(O)C)CC2)C=C1)C=1C(=NC=NC=1)C(C)C LPYQMZPUGIQGLF-UHFFFAOYSA-N 0.000 claims 1
SZYBSXJMEIMAFT-UHFFFAOYSA-N 1-[6-[5-[4-fluoro-2-(2-propan-2-ylphenyl)phenoxy]pyrimidin-4-yl]-2,6-diazaspiro[3.3]heptan-2-yl]-2-(4-methylsulfonylphenyl)ethanone Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(C)C)OC=1C(=NC=NC=1)N1CC2(CN(C2)C(CC2=CC=C(C=C2)S(=O)(=O)C)=O)C1 SZYBSXJMEIMAFT-UHFFFAOYSA-N 0.000 claims 1
PNUYHRGGBPMWQF-UHFFFAOYSA-N 1-[6-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2,6-diazaspiro[3.3]heptan-2-yl]-2-(6-methoxypyridin-3-yl)ethanone Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CN(C3)C(CC=3C=NC(=CC=3)OC)=O)C2)C=C1)C=1C(=NC=NC=1)C(C)C PNUYHRGGBPMWQF-UHFFFAOYSA-N 0.000 claims 1
ICPWBQQPIXUYPS-UHFFFAOYSA-N 1-[7-[5-[2-(2-ethylphenyl)-4-fluoroanilino]pyrimidin-4-yl]-2,7-diazaspiro[3.5]nonan-2-yl]-2-methylpropan-2-ol Chemical compound C(C)C1=C(C=CC=C1)C1=C(C=CC(=C1)F)NC=1C(=NC=NC=1)N1CCC2(CN(C2)CC(C)(O)C)CC1 ICPWBQQPIXUYPS-UHFFFAOYSA-N 0.000 claims 1
KRQIFMNWSUEFMA-UHFFFAOYSA-N 1-[[2-[5-[4-fluoro-2-[2-propan-2-yl-5-(trifluoromethyl)pyrazol-3-yl]phenoxy]pyrimidin-4-yl]-2,6-diazaspiro[3.3]heptan-6-yl]methyl]cyclohexan-1-ol Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CN(C3)CC3(CCCCC3)O)C2)C=C1)C1=CC(=NN1C(C)C)C(F)(F)F KRQIFMNWSUEFMA-UHFFFAOYSA-N 0.000 claims 1
KWVUTVGLAFNDCF-UHFFFAOYSA-N 2-[3-[[2-(2-ethylphenyl)-4-fluorophenyl]methyl]pyridin-4-yl]-6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptane Chemical compound C(C)C1=C(C=CC=C1)C1=C(C=CC(=C1)F)CC=1C=NC=CC=1N1CC2(C1)CN(C2)CC1CCOCC1 KWVUTVGLAFNDCF-UHFFFAOYSA-N 0.000 claims 1
LPYYVWIIEFXKHK-UHFFFAOYSA-N 2-[4-[2-[2-(4-cyanophenyl)acetyl]-2,6-diazaspiro[3.3]heptan-6-yl]pyrimidin-5-yl]oxy-5-fluoro-N,N-di(propan-2-yl)benzamide Chemical compound C(#N)C1=CC=C(C=C1)CC(=O)N1CC2(CN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C(C)C)C(C)C)C=C(C=C2)F)C1 LPYYVWIIEFXKHK-UHFFFAOYSA-N 0.000 claims 1
MJQZDGYFJCOLFS-UHFFFAOYSA-N 2-[4-[2-[2-(4-cyanophenyl)acetyl]-2,7-diazaspiro[3.4]octan-7-yl]pyrimidin-5-yl]oxy-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(#N)C1=CC=C(C=C1)CC(=O)N1CC2(C1)CN(CC2)C1=NC=NC=C1OC1=C(C(=O)N(C)C(C)C)C=C(C=C1)F MJQZDGYFJCOLFS-UHFFFAOYSA-N 0.000 claims 1
GBDPLBOHEGLIOI-UHFFFAOYSA-N 2-[4-[3-[(4-acetamidophenyl)methyl]-2-amino-4-oxo-1,3,7-triazaspiro[4.4]non-1-en-7-yl]pyrimidin-5-yl]oxy-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(C)(=O)NC1=CC=C(CN2C(=NC3(C2=O)CN(CC3)C2=NC=NC=C2OC2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)N)C=C1 GBDPLBOHEGLIOI-UHFFFAOYSA-N 0.000 claims 1
BXJIUXOTVWMZDE-UHFFFAOYSA-N 2-[4-[7-(1,4-dioxaspiro[4.5]decan-8-ylmethyl)-2,7-diazaspiro[3.5]nonan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N,N-di(propan-2-yl)benzamide Chemical compound O1CCOC11CCC(CC1)CN1CCC2(CN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C(C)C)C(C)C)C=C(C=C2)F)CC1 BXJIUXOTVWMZDE-UHFFFAOYSA-N 0.000 claims 1
KHHKEUHNPVFCNZ-UHFFFAOYSA-N 2-[4-[7-(2,2-dimethylpropyl)-2,7-diazaspiro[3.4]octan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(C1)CN(CC2)CC(C)(C)C KHHKEUHNPVFCNZ-UHFFFAOYSA-N 0.000 claims 1
SNRHUGOVTUYLAE-UHFFFAOYSA-N 2-[4-[7-(6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)-2,7-diazaspiro[3.4]octan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N,N-di(propan-2-yl)benzamide Chemical compound CC(C)N(C(C)C)C(=O)C1=C(OC2=C(N=CN=C2)N2CC3(C2)CCN(C3)C2CCC3=C(C2)C=CC(=C3)C#N)C=CC(F)=C1 SNRHUGOVTUYLAE-UHFFFAOYSA-N 0.000 claims 1
WNOGVHWSLLRVCS-UHFFFAOYSA-N 2-[4-[7-(cyclopropylmethyl)-2,7-diazaspiro[3.4]octan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N,N-di(propan-2-yl)benzamide Chemical compound C1(CC1)CN1CC2(CN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C(C)C)C(C)C)C=C(C=C2)F)CC1 WNOGVHWSLLRVCS-UHFFFAOYSA-N 0.000 claims 1
UFUNVCPGWLPFSK-UHFFFAOYSA-N 2-[4-[7-[(3,3-dimethyl-2-oxo-1H-indol-6-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound CC1(C(NC2=CC(=CC=C12)CN1CC2(CCN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)CC1)=O)C UFUNVCPGWLPFSK-UHFFFAOYSA-N 0.000 claims 1
XNDPFXZXQAJYAL-UHFFFAOYSA-N 2-[4-[7-[(3-cyano-1H-indazol-6-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(#N)C1=NNC2=CC(=CC=C12)CN1CC2(CCN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)CC1 XNDPFXZXQAJYAL-UHFFFAOYSA-N 0.000 claims 1
YXNIYINCHLJCCF-UHFFFAOYSA-N 2-[4-[7-[(3-cyano-3-methyl-2-oxo-1H-indol-6-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N,N-di(propan-2-yl)benzamide Chemical compound C(#N)C1(C(NC2=CC(=CC=C12)CN1CC2(CCN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C(C)C)C(C)C)C=C(C=C2)F)CC1)=O)C YXNIYINCHLJCCF-UHFFFAOYSA-N 0.000 claims 1
IDINYCZUDINCRW-UHFFFAOYSA-N 2-[4-[7-[(3-cyano-3-methyl-2-oxo-1H-indol-6-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(#N)C1(C(NC2=CC(=CC=C12)CN1CC2(CCN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)CC1)=O)C IDINYCZUDINCRW-UHFFFAOYSA-N 0.000 claims 1
LHEIQDJUJRZLEV-UHFFFAOYSA-N 2-[4-[7-[(6-cyano-1H-indol-3-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(#N)C1=CC=C2C(=CNC2=C1)CN1CC2(CCN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)CC1 LHEIQDJUJRZLEV-UHFFFAOYSA-N 0.000 claims 1
ABSXKKVPHIJYAC-UHFFFAOYSA-N 2-[4-[7-[2-(4-cyanophenyl)acetyl]-2,7-diazaspiro[3.4]octan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N,N-di(propan-2-yl)benzamide Chemical compound C(#N)C1=CC=C(C=C1)CC(=O)N1CC2(CN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C(C)C)C(C)C)C=C(C=C2)F)CC1 ABSXKKVPHIJYAC-UHFFFAOYSA-N 0.000 claims 1
BKRRDUISBFATNR-UHFFFAOYSA-N 2-[4-[7-[[1-(2-acetamidoethyl)-2-oxo-3H-benzimidazol-5-yl]methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(C)(=O)NCCN1C(NC2=C1C=CC(=C2)CN1CC2(CCN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)CC1)=O BKRRDUISBFATNR-UHFFFAOYSA-N 0.000 claims 1
UTIBYAFAWFRERU-UHFFFAOYSA-N 2-[4-[7-[[1-[2-(dimethylamino)ethyl]-2-oxo-3H-benzimidazol-5-yl]methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound CN(CCN1C(NC2=C1C=CC(=C2)CN1CC2(CCN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)CC1)=O)C UTIBYAFAWFRERU-UHFFFAOYSA-N 0.000 claims 1
ZAULWOWAPRKFDV-UHFFFAOYSA-N 2-[4-[8-amino-7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2-azaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N,N-di(propan-2-yl)benzamide Chemical compound NC1CC2(CCN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C(C)C)C(C)C)C=C(C=C2)F)CC1CC1=CC2=C(NC(N2)=O)C=C1 ZAULWOWAPRKFDV-UHFFFAOYSA-N 0.000 claims 1
SNIZCLYDBWDWKS-UHFFFAOYSA-N 2-[4-[8-amino-8-[(4-cyanophenyl)methyl]-2-azaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-5-fluoro-N,N-di(propan-2-yl)benzamide Chemical compound NC1(CC2(CCN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C(C)C)C(C)C)C=C(C=C2)F)CC1)CC1=CC=C(C=C1)C#N SNIZCLYDBWDWKS-UHFFFAOYSA-N 0.000 claims 1
XDAIZFDVPKBLDB-UHFFFAOYSA-N 2-[5-(2-cyclopropyloxy-4-fluorophenoxy)pyrimidin-4-yl]-7-(oxan-4-ylmethyl)-2,7-diazaspiro[4.4]nonane Chemical compound C1(CC1)OC1=C(OC=2C(=NC=NC=2)N2CC3(CC2)CN(CC3)CC2CCOCC2)C=CC(=C1)F XDAIZFDVPKBLDB-UHFFFAOYSA-N 0.000 claims 1
PMPWFFPGIIWURA-UHFFFAOYSA-N 2-[5-[2-(2-cyclopropylpyridin-3-yl)-4-fluorophenoxy]pyrimidin-4-yl]-6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptane Chemical compound C1(CC1)C1=NC=CC=C1C1=C(OC=2C(=NC=NC=2)N2CC3(C2)CN(C3)CC2CCOCC2)C=CC(=C1)F PMPWFFPGIIWURA-UHFFFAOYSA-N 0.000 claims 1
SECMPUOEOARXER-UHFFFAOYSA-N 2-[5-[4-fluoro-2-(2-propan-2-yloxypyridin-3-yl)phenoxy]pyrimidin-4-yl]-6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptane Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(C2)CN(C3)CC2CCOCC2)C=C1)C=1C(=NC=CC=1)OC(C)C SECMPUOEOARXER-UHFFFAOYSA-N 0.000 claims 1
VIOKIUFWIPVVKO-UHFFFAOYSA-N 2-[5-[4-fluoro-2-(2-propan-2-ylphenyl)phenoxy]pyrimidin-4-yl]-6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptane Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(C)C)OC=1C(=NC=NC=1)N1CC2(C1)CN(C2)CC1CCOCC1 VIOKIUFWIPVVKO-UHFFFAOYSA-N 0.000 claims 1
DHEKZZFDLQOXLE-UHFFFAOYSA-N 2-[5-[4-fluoro-2-[2-(1-methoxyethyl)phenyl]phenoxy]pyrimidin-4-yl]-6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptane Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(C)OC)OC=1C(=NC=NC=1)N1CC2(C1)CN(C2)CC1CCOCC1 DHEKZZFDLQOXLE-UHFFFAOYSA-N 0.000 claims 1
UUHGOPANRBLYEE-UHFFFAOYSA-N 2-[5-[4-fluoro-2-[4-fluoro-2-(2-fluoropropan-2-yl)phenyl]phenoxy]pyrimidin-4-yl]-6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptane Chemical compound FC1=CC(=C(C=C1)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(C1)CN(C2)CC1CCOCC1)C(C)(C)F UUHGOPANRBLYEE-UHFFFAOYSA-N 0.000 claims 1
MKHPDHYWQOOMKF-UHFFFAOYSA-N 2-[6-[5-(2-chloro-4-fluorophenoxy)pyrimidin-4-yl]-2,6-diazaspiro[3.3]heptane-2-carbonyl]-2,3-dihydro-1H-indene-5-sulfonamide Chemical compound ClC1=C(OC=2C(=NC=NC=2)N2CC3(CN(C3)C(=O)C3CC4=CC=C(C=C4C3)S(=O)(=O)N)C2)C=CC(=C1)F MKHPDHYWQOOMKF-UHFFFAOYSA-N 0.000 claims 1
ANMHKIAAHDVLTD-UHFFFAOYSA-N 2-[7-[5-[2-(4-cyano-2-cyclopropylphenyl)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-2-yl]-1,3-thiazole-4-carboxylic acid Chemical compound C(#N)C1=CC(=C(C=C1)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CCN(C2)C=2SC=C(N=2)C(=O)O)CC1)C1CC1 ANMHKIAAHDVLTD-UHFFFAOYSA-N 0.000 claims 1
XLPHORBSKKCBQH-UHFFFAOYSA-N 2-[7-[5-[2-(4-cyano-2-cyclopropylphenyl)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-2-yl]-N,N-dimethyl-1,3-thiazole-4-carboxamide Chemical compound C(#N)C1=CC(=C(C=C1)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CCN(C2)C=2SC=C(N=2)C(=O)N(C)C)CC1)C1CC1 XLPHORBSKKCBQH-UHFFFAOYSA-N 0.000 claims 1
IOUFKIJDPVGYHE-UHFFFAOYSA-N 2-[7-[5-[2-(4-cyano-2-cyclopropylphenyl)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-2-yl]-N-methyl-1,3-thiazole-4-carboxamide Chemical compound C(#N)C1=CC(=C(C=C1)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CCN(C2)C=2SC=C(N=2)C(=O)NC)CC1)C1CC1 IOUFKIJDPVGYHE-UHFFFAOYSA-N 0.000 claims 1
WIOYIHFRSVWVIA-UHFFFAOYSA-N 2-amino-2-cyclohexyl-1-[7-[5-[4-fluoro-2-(2-propan-2-ylpyrazol-3-yl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-2-yl]ethanone Chemical compound NC(C(=O)N1CC2(CC1)CN(CC2)C1=NC=NC=C1OC1=C(C=C(C=C1)F)C1=CC=NN1C(C)C)C1CCCCC1 WIOYIHFRSVWVIA-UHFFFAOYSA-N 0.000 claims 1
QJRFQADPYUNILM-UHFFFAOYSA-N 3-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]-2-methylbenzonitrile Chemical compound FC=1C=CC(=C(C=1)C1=C(C(=CC=C1)C#N)C)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 QJRFQADPYUNILM-UHFFFAOYSA-N 0.000 claims 1
RMNSPFJEYVIHJR-UHFFFAOYSA-N 3-[[2-[5-(2-cyclopentyloxy-4-fluorophenoxy)pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1H-indole-6-carbonitrile Chemical compound C1(CCCC1)OC1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CNC4=CC(=CC=C34)C#N)CC2)C=CC(=C1)F RMNSPFJEYVIHJR-UHFFFAOYSA-N 0.000 claims 1
ONTHXNIGNLBDPN-UHFFFAOYSA-N 3-[[2-[5-[2-(cyclopropylmethoxy)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1H-indole-6-carbonitrile Chemical compound C1(CC1)COC1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CNC4=CC(=CC=C34)C#N)CC2)C=CC(=C1)F ONTHXNIGNLBDPN-UHFFFAOYSA-N 0.000 claims 1
VGAUFRIMBWHASR-UHFFFAOYSA-N 3-[[2-[5-[2-(cyclopropylmethoxy)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1H-indole-6-carboxamide Chemical compound C1(CC1)COC1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CNC4=CC(=CC=C34)C(=O)N)CC2)C=CC(=C1)F VGAUFRIMBWHASR-UHFFFAOYSA-N 0.000 claims 1
QTGWATGWTLRBAO-UHFFFAOYSA-N 3-cyclopropyl-4-[2-[4-[7-[(1-ethyl-2-oxo-3H-benzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-5-fluorophenyl]benzonitrile Chemical compound C1(CC1)C1=C(C=CC(=C1)C#N)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(N(C(N2)=O)CC)C=C1 QTGWATGWTLRBAO-UHFFFAOYSA-N 0.000 claims 1
XKWJAPBUHZSMPS-UHFFFAOYSA-N 3-cyclopropyl-4-[2-[4-[7-[(3,3-dimethyl-2-oxo-1H-indol-6-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-5-fluorophenyl]benzonitrile Chemical compound C1(CC1)C1=C(C=CC(=C1)C#N)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC=C2C(C(NC2=C1)=O)(C)C XKWJAPBUHZSMPS-UHFFFAOYSA-N 0.000 claims 1
MGXQWNWBSLUIHG-UHFFFAOYSA-N 3-cyclopropyl-4-[5-fluoro-2-[4-[6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptan-2-yl]pyrimidin-5-yl]oxyphenyl]benzonitrile Chemical compound C1(CC1)C1=C(C=CC(=C1)C#N)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(C1)CN(C2)CC1CCOCC1 MGXQWNWBSLUIHG-UHFFFAOYSA-N 0.000 claims 1
WWVFRXNVKJLBPL-UHFFFAOYSA-N 3-cyclopropyl-4-[5-fluoro-2-[4-[6-[(4-hydroxyoxan-4-yl)methyl]-2,6-diazaspiro[3.3]heptan-2-yl]pyrimidin-5-yl]oxyphenyl]benzonitrile Chemical compound C1(CC1)C1=C(C=CC(=C1)C#N)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(C1)CN(C2)CC1(CCOCC1)O WWVFRXNVKJLBPL-UHFFFAOYSA-N 0.000 claims 1
UVZHQNADORUTIM-UHFFFAOYSA-N 3-cyclopropyl-4-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]-N,N-dimethylbenzamide Chemical compound C1(CC1)C1=C(C=CC(=C1)C(=O)N(C)C)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 UVZHQNADORUTIM-UHFFFAOYSA-N 0.000 claims 1
RCAPYFSPYWPIGW-UHFFFAOYSA-N 3-cyclopropyl-4-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]benzamide Chemical compound C1(CC1)C1=C(C=CC(=C1)C(=O)N)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 RCAPYFSPYWPIGW-UHFFFAOYSA-N 0.000 claims 1
OHCOCFHCHYPUTM-UHFFFAOYSA-N 3-cyclopropyl-4-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]benzoic acid Chemical compound C1(CC1)C1=C(C=CC(=C1)C(=O)O)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 OHCOCFHCHYPUTM-UHFFFAOYSA-N 0.000 claims 1
CIIQZZPBYFSNDO-UHFFFAOYSA-N 3-cyclopropyl-4-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]benzonitrile Chemical compound C1(CC1)C1=C(C=CC(=C1)C#N)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 CIIQZZPBYFSNDO-UHFFFAOYSA-N 0.000 claims 1
AIHTXZIPQLYLJH-UHFFFAOYSA-N 3-cyclopropyl-4-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydroindol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]benzonitrile Chemical compound C1(CC1)C1=C(C=CC(=C1)C#N)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC=1C=C2CC(NC2=CC=1)=O AIHTXZIPQLYLJH-UHFFFAOYSA-N 0.000 claims 1
WXMANLZHLWRRER-UHFFFAOYSA-N 3-cyclopropyl-4-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydroindol-6-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]benzonitrile Chemical compound C1(CC1)C1=C(C=CC(=C1)C#N)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC=C2CC(NC2=C1)=O WXMANLZHLWRRER-UHFFFAOYSA-N 0.000 claims 1
HPKLIKRWSGMMFA-UHFFFAOYSA-N 3-cyclopropyl-4-[5-fluoro-2-[4-[7-[(2-oxo-3H-1,3-benzoxazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]benzonitrile Chemical compound C1(CC1)C1=C(C=CC(=C1)C#N)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC=1C=CC2=C(NC(O2)=O)C=1 HPKLIKRWSGMMFA-UHFFFAOYSA-N 0.000 claims 1
SKRONMLKPVZXKM-UHFFFAOYSA-N 3-cyclopropyl-4-[5-fluoro-2-[4-[7-[[4-(2-oxopyrrolidin-1-yl)phenyl]methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]benzonitrile Chemical compound C1(CC1)C1=C(C=CC(=C1)C#N)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC=C(C=C1)N1C(CCC1)=O SKRONMLKPVZXKM-UHFFFAOYSA-N 0.000 claims 1
WIYAOYDITUQKOT-UHFFFAOYSA-N 4-[1-[[2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2-azaspiro[3.3]heptan-6-yl]amino]ethyl]benzonitrile Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(C2)CC(C3)NC(C)C2=CC=C(C#N)C=C2)C=C1)C=1C(=NC=NC=1)C(C)C WIYAOYDITUQKOT-UHFFFAOYSA-N 0.000 claims 1
IOYUPOSFBJUMEI-UHFFFAOYSA-N 4-[2-[2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[3.4]octan-7-yl]-2-oxoethyl]benzonitrile Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(C2)CN(CC3)C(CC2=CC=C(C#N)C=C2)=O)C=C1)C=1C(=NC=NC=1)C(C)C IOYUPOSFBJUMEI-UHFFFAOYSA-N 0.000 claims 1
LYKVITWCPPVLHF-UHFFFAOYSA-N 4-[2-[4-(8-amino-8-benzyl-2-azaspiro[4.4]nonan-2-yl)pyrimidin-5-yl]oxy-5-fluorophenyl]-3-cyclopropylbenzonitrile Chemical compound NC1(CC2(CCN(C2)C2=NC=NC=C2OC2=C(C=C(C=C2)F)C2=C(C=C(C=C2)C#N)C2CC2)CC1)CC1=CC=CC=C1 LYKVITWCPPVLHF-UHFFFAOYSA-N 0.000 claims 1
MSVFFVKRIJJSIO-UHFFFAOYSA-N 4-[2-[4-[6-[2-(4-cyanophenyl)ethyl]-2,6-diazaspiro[3.3]heptan-2-yl]pyrimidin-5-yl]oxy-5-fluorophenyl]-3-cyclopropylbenzonitrile Chemical compound C(#N)C1=CC=C(CCN2CC3(CN(C3)C3=NC=NC=C3OC3=C(C=C(C=C3)F)C3=C(C=C(C=C3)C#N)C3CC3)C2)C=C1 MSVFFVKRIJJSIO-UHFFFAOYSA-N 0.000 claims 1
KEOHMDDJIINFTB-UHFFFAOYSA-N 4-[2-[4-[7-(2H-benzotriazol-5-ylmethyl)-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-5-fluorophenyl]-3-cyclopropylbenzonitrile Chemical compound N1N=NC2=C1C=C(C=C2)CN1CC2(CCN(C2)C2=NC=NC=C2OC2=C(C=C(C=C2)F)C2=C(C=C(C=C2)C#N)C2CC2)CC1 KEOHMDDJIINFTB-UHFFFAOYSA-N 0.000 claims 1
DDLPKSOJAWKGTQ-UHFFFAOYSA-N 4-[2-[6-[5-[4-fluoro-2-(2-propan-2-ylphenyl)phenoxy]pyrimidin-4-yl]-2,6-diazaspiro[3.3]heptan-2-yl]-2-oxoethyl]benzonitrile Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(C)C)OC=1C(=NC=NC=1)N1CC2(CN(C2)C(CC2=CC=C(C#N)C=C2)=O)C1 DDLPKSOJAWKGTQ-UHFFFAOYSA-N 0.000 claims 1
GINFHYPQDAFVJV-UHFFFAOYSA-N 4-[2-[6-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2,6-diazaspiro[3.3]heptan-2-yl]-2-oxoethyl]benzonitrile Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CN(C3)C(CC3=CC=C(C#N)C=C3)=O)C2)C=C1)C=1C(=NC=NC=1)C(C)C GINFHYPQDAFVJV-UHFFFAOYSA-N 0.000 claims 1
FQTBRFPSATVARS-UHFFFAOYSA-N 4-[2-[7-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[3.4]octan-2-yl]-2-oxoethyl]benzonitrile Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CN(C3)C(CC3=CC=C(C#N)C=C3)=O)CC2)C=C1)C=1C(=NC=NC=1)C(C)C FQTBRFPSATVARS-UHFFFAOYSA-N 0.000 claims 1
BOFSLQRFWHUJNB-UHFFFAOYSA-N 4-[5-fluoro-2-[4-[6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptan-2-yl]pyrimidin-5-yl]oxyphenyl]-3-methyl-5-propan-2-yl-1,2-oxazole Chemical compound FC=1C=CC(=C(C=1)C=1C(=NOC=1C(C)C)C)OC=1C(=NC=NC=1)N1CC2(C1)CN(C2)CC1CCOCC1 BOFSLQRFWHUJNB-UHFFFAOYSA-N 0.000 claims 1
IODLEYCTGBGERW-UHFFFAOYSA-N 4-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]-3,5-dimethylbenzonitrile Chemical compound FC=1C=CC(=C(C=1)C1=C(C=C(C=C1C)C#N)C)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 IODLEYCTGBGERW-UHFFFAOYSA-N 0.000 claims 1
XPVJKZODQOVMBT-UHFFFAOYSA-N 4-[[2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2,6-diazaspiro[3.3]heptan-6-yl]methyl]cyclohexan-1-ol Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CN(C3)CC3CCC(CC3)O)C2)C=C1)C=1C(=NC=NC=1)C(C)C XPVJKZODQOVMBT-UHFFFAOYSA-N 0.000 claims 1
FYAVTYMBAMXOCA-UHFFFAOYSA-N 4-[[2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2-azaspiro[3.3]heptan-6-yl]amino]-1-methylcyclohexane-1-carbonitrile Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(C2)CC(C3)NC2CCC(CC2)(C#N)C)C=C1)C=1C(=NC=NC=1)C(C)C FYAVTYMBAMXOCA-UHFFFAOYSA-N 0.000 claims 1
VSTKPBJCXLWNCQ-UHFFFAOYSA-N 4-[[[2-[5-[4-fluoro-2-(2-propan-2-ylphenyl)phenoxy]pyrimidin-4-yl]-5-oxa-2-azaspiro[3.4]octan-7-yl]amino]methyl]benzonitrile Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(C)C)OC=1C(=NC=NC=1)N1CC2(C1)OCC(C2)NCC1=CC=C(C#N)C=C1 VSTKPBJCXLWNCQ-UHFFFAOYSA-N 0.000 claims 1
FUBVASRLRIBIEP-UHFFFAOYSA-N 4-[[[2-[5-[4-fluoro-2-(2-propan-2-ylpyrazol-3-yl)phenoxy]pyrimidin-4-yl]-5-oxa-2-azaspiro[3.4]octan-7-yl]amino]methyl]benzonitrile Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(C2)OCC(C3)NCC2=CC=C(C#N)C=C2)C=C1)C1=CC=NN1C(C)C FUBVASRLRIBIEP-UHFFFAOYSA-N 0.000 claims 1
IIBNTQLYAANLLE-UHFFFAOYSA-N 4-[[[2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2-azaspiro[3.3]heptan-6-yl]amino]methyl]-1-methylcyclohexane-1-carbonitrile Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(C2)CC(C3)NCC2CCC(CC2)(C#N)C)C=C1)C=1C(=NC=NC=1)C(C)C IIBNTQLYAANLLE-UHFFFAOYSA-N 0.000 claims 1
JKJSQTMLDYINGB-UHFFFAOYSA-N 4-[[[2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2-azaspiro[3.3]heptan-6-yl]amino]methyl]benzonitrile Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(C2)CC(C3)NCC2=CC=C(C#N)C=C2)C=C1)C=1C(=NC=NC=1)C(C)C JKJSQTMLDYINGB-UHFFFAOYSA-N 0.000 claims 1
HNTRULWDLQGJAY-UHFFFAOYSA-N 4-[[[2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-5-oxa-2-azaspiro[3.4]octan-7-yl]-methylamino]methyl]benzonitrile Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(C2)OCC(C3)N(C)CC2=CC=C(C#N)C=C2)C=C1)C=1C(=NC=NC=1)C(C)C HNTRULWDLQGJAY-UHFFFAOYSA-N 0.000 claims 1
BGNLXYVXDYPJGQ-UHFFFAOYSA-N 5-[5-fluoro-2-[4-[6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptan-2-yl]pyrimidin-5-yl]oxyphenyl]-2,3-dihydro-1H-inden-2-amine Chemical compound FC=1C=CC(=C(C=1)C=1C=C2CC(CC2=CC=1)N)OC=1C(=NC=NC=1)N1CC2(C1)CN(C2)CC1CCOCC1 BGNLXYVXDYPJGQ-UHFFFAOYSA-N 0.000 claims 1
BXAVPBWQLWFRFK-UHFFFAOYSA-N 5-[[2-[3-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyridin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C=NC=CC=2N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)C=1C(=NC=NC=1)C(C)C BXAVPBWQLWFRFK-UHFFFAOYSA-N 0.000 claims 1
QXQMFUQWZNMXAJ-UHFFFAOYSA-N 5-[[2-[5-(2-dimethylphosphoryl-4-fluorophenoxy)pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound CP(=O)(C)C1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=CC(=C1)F QXQMFUQWZNMXAJ-UHFFFAOYSA-N 0.000 claims 1
HQCSFKFNGKQQCW-UHFFFAOYSA-N 5-[[2-[5-(4-fluoro-2-methoxyphenoxy)pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)OC HQCSFKFNGKQQCW-UHFFFAOYSA-N 0.000 claims 1
ZZVRBFVMGKRFSW-UHFFFAOYSA-N 5-[[2-[5-(4-fluoro-2-phenylmethoxyphenoxy)pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound C(C1=CC=CC=C1)OC1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=CC(=C1)F ZZVRBFVMGKRFSW-UHFFFAOYSA-N 0.000 claims 1
ZPUOVBCTFKUQRP-UHFFFAOYSA-N 5-[[2-[5-[2-(2,5-dimethylpyrrolidine-1-carbonyl)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound CC1N(C(CC1)C)C(=O)C1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=CC(=C1)F ZPUOVBCTFKUQRP-UHFFFAOYSA-N 0.000 claims 1
WPVYCCOUFBPOTI-UHFFFAOYSA-N 5-[[2-[5-[2-(2-cyclopropylphenyl)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound C1(CC1)C1=C(C=CC=C1)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CCN(C2)CC2=CC3=C(NC(N3)=O)C=C2)CC1 WPVYCCOUFBPOTI-UHFFFAOYSA-N 0.000 claims 1
AIZDPHNUBBVMKH-UHFFFAOYSA-N 5-[[2-[5-[2-(2-cyclopropylpyridin-3-yl)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound C1(CC1)C1=NC=CC=C1C1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=CC(=C1)F AIZDPHNUBBVMKH-UHFFFAOYSA-N 0.000 claims 1
FKWCGFBXIBUEQD-UHFFFAOYSA-N 5-[[2-[5-[2-(2-ethylpyridin-3-yl)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound C(C)C1=NC=CC=C1C1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=CC(=C1)F FKWCGFBXIBUEQD-UHFFFAOYSA-N 0.000 claims 1
FKBJXOKPRIVWOY-UHFFFAOYSA-N 5-[[2-[5-[2-(3-cyclopropyl-1-methyl-6-oxopyridin-2-yl)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound C1(CC1)C1=C(N(C(C=C1)=O)C)C1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=CC(=C1)F FKBJXOKPRIVWOY-UHFFFAOYSA-N 0.000 claims 1
AXTUKVPEJXJFSW-UHFFFAOYSA-N 5-[[2-[5-[2-(cyclopropylmethoxy)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound C1(CC1)COC1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=CC(=C1)F AXTUKVPEJXJFSW-UHFFFAOYSA-N 0.000 claims 1
XODPUMUKXOUEQM-UHFFFAOYSA-N 5-[[2-[5-[2-[2-(1,1-difluoroethyl)phenyl]-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC(C)(F)C1=C(C=CC=C1)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CCN(C2)CC2=CC3=C(NC(N3)=O)C=C2)CC1 XODPUMUKXOUEQM-UHFFFAOYSA-N 0.000 claims 1
HKHAZYPEWNFWOW-UHFFFAOYSA-N 5-[[2-[5-[2-[amino(cyclopentyl)methyl]-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound NC(C1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=CC(=C1)F)C1CCCC1 HKHAZYPEWNFWOW-UHFFFAOYSA-N 0.000 claims 1
QLJCVCZPMXZNSO-UHFFFAOYSA-N 5-[[2-[5-[2-[cyclopentyl(dimethylamino)methyl]-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound C1(CCCC1)C(C1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=CC(=C1)F)N(C)C QLJCVCZPMXZNSO-UHFFFAOYSA-N 0.000 claims 1
MPECJFNXNLAMPU-UHFFFAOYSA-N 5-[[2-[5-[4,5-difluoro-2-(2-propan-2-ylphenyl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(C=C1F)C1=C(C=CC=C1)C(C)C)OC=1C(=NC=NC=1)N1CC2(CCN(C2)CC2=CC3=C(NC(N3)=O)C=C2)CC1 MPECJFNXNLAMPU-UHFFFAOYSA-N 0.000 claims 1
QVEBXWNDMLOZIL-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(2-methoxybutan-2-yl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)C(C)(CC)OC QVEBXWNDMLOZIL-UHFFFAOYSA-N 0.000 claims 1
WGTMQBLWYZOIPS-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(2-oxo-5-propan-2-ylpyrrolidin-1-yl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)N1C(CCC1=O)C(C)C WGTMQBLWYZOIPS-UHFFFAOYSA-N 0.000 claims 1
CRDPPUZFMLFSQU-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(2-prop-1-en-2-ylphenyl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(=C)C)OC=1C(=NC=NC=1)N1CC2(CCN(C2)CC2=CC3=C(NC(N3)=O)C=C2)CC1 CRDPPUZFMLFSQU-UHFFFAOYSA-N 0.000 claims 1
CFXYUZFTVYIWBB-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(2-propan-2-ylimidazol-1-yl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)N1C(=NC=C1)C(C)C CFXYUZFTVYIWBB-UHFFFAOYSA-N 0.000 claims 1
PCXDFPZJWUHYJP-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(2-propan-2-ylpyrazol-3-yl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)C1=CC=NN1C(C)C PCXDFPZJWUHYJP-UHFFFAOYSA-N 0.000 claims 1
CCKFNBGKIBUCLS-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(2-propan-2-ylpyrazol-3-yl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-2H-benzotriazole Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC=3C=CC4=C(NN=N4)C=3)CC2)C=C1)C1=CC=NN1C(C)C CCKFNBGKIBUCLS-UHFFFAOYSA-N 0.000 claims 1
DVXVRZMBNDVWBY-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(3-hydroxy-3-methylbutyl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)CCC(C)(C)O DVXVRZMBNDVWBY-UHFFFAOYSA-N 0.000 claims 1
YNYXOKCWPLBSTB-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(3-hydroxypentan-3-yl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)C(CC)(CC)O YNYXOKCWPLBSTB-UHFFFAOYSA-N 0.000 claims 1
QBBLCOYMVNUFSC-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(3-methylbutyl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound CC(C)CCc1cc(F)ccc1Oc1cncnc1N1CCC2(CCN(Cc3ccc4[nH]c(=O)[nH]c4c3)C2)C1 QBBLCOYMVNUFSC-UHFFFAOYSA-N 0.000 claims 1
POWXGQJURDRKFF-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(4-propan-2-yl-1,3-thiazol-5-yl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)C1=C(N=CS1)C(C)C POWXGQJURDRKFF-UHFFFAOYSA-N 0.000 claims 1
WNFNHMDDZWMNGH-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)C=1C(=NC=NC=1)C(C)C WNFNHMDDZWMNGH-UHFFFAOYSA-N 0.000 claims 1
CAQRGNFXNUQATN-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(5-propan-2-yl-1,3-thiazol-4-yl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)C=1N=CSC=1C(C)C CAQRGNFXNUQATN-UHFFFAOYSA-N 0.000 claims 1
YHWYHHXJQWYQAA-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(morpholin-4-ylmethyl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)CN1CCOCC1 YHWYHHXJQWYQAA-UHFFFAOYSA-N 0.000 claims 1
QKSWUFUDAGTKQD-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(morpholine-4-carbonyl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)C(=O)N1CCOCC1 QKSWUFUDAGTKQD-UHFFFAOYSA-N 0.000 claims 1
YXZSNMAWSXSGNI-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-(pyrrolidine-1-carbonyl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)C(=O)N1CCCC1 YXZSNMAWSXSGNI-UHFFFAOYSA-N 0.000 claims 1
SHHZNWHLCXEVDN-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-[2-(1-hydroxyethyl)phenyl]phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(C)O)OC=1C(=NC=NC=1)N1CC2(CCN(C2)CC2=CC3=C(NC(N3)=O)C=C2)CC1 SHHZNWHLCXEVDN-UHFFFAOYSA-N 0.000 claims 1
ALTQTUKNKJRUHA-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-[2-(1-hydroxypropan-2-yl)phenyl]phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(CO)C)OC=1C(=NC=NC=1)N1CC2(CCN(C2)CC2=CC3=C(NC(N3)=O)C=C2)CC1 ALTQTUKNKJRUHA-UHFFFAOYSA-N 0.000 claims 1
LAPGNXROYVXHRX-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-[2-(2-hydroxypropan-2-yl)phenyl]phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(C)(C)O)OC=1C(=NC=NC=1)N1CC2(CCN(C2)CC2=CC3=C(NC(N3)=O)C=C2)CC1 LAPGNXROYVXHRX-UHFFFAOYSA-N 0.000 claims 1
KYAROJVNYHROOQ-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-[2-(trifluoromethyl)phenyl]phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(F)(F)F)OC=1C(=NC=NC=1)N1CC2(CCN(C2)CC2=CC3=C(NC(N3)=O)C=C2)CC1 KYAROJVNYHROOQ-UHFFFAOYSA-N 0.000 claims 1
QAZWZROZNZGYQQ-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-[2-propan-2-yl-5-(trifluoromethyl)pyrazol-3-yl]phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)C1=CC(=NN1C(C)C)C(F)(F)F QAZWZROZNZGYQQ-UHFFFAOYSA-N 0.000 claims 1
FBHTTWUKVPPAQR-UHFFFAOYSA-N 5-[[2-[5-[4-fluoro-2-[[methyl(propan-2-yl)amino]methyl]phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(NC(N4)=O)C=C3)CC2)C=C1)CN(C)C(C)C FBHTTWUKVPPAQR-UHFFFAOYSA-N 0.000 claims 1
MMINYJKELIGEJE-UHFFFAOYSA-N 5-[[8-[5-(2-chloro-4-fluorophenoxy)pyrimidin-4-yl]-2-azaspiro[4.4]nonan-2-yl]methyl]-3-methyl-1H-benzimidazol-2-one Chemical compound ClC1=C(OC=2C(=NC=NC=2)C2CC3(CCN(C3)CC=3C=CC4=C(N(C(N4)=O)C)C=3)CC2)C=CC(=C1)F MMINYJKELIGEJE-UHFFFAOYSA-N 0.000 claims 1
WHBBMYHGXNWVMF-UHFFFAOYSA-N 5-fluoro-2-[4-[3-[(4-fluorophenyl)methyl]-2-(2-hydroxyethyl)-2,7-diazaspiro[4.4]nonan-7-yl]pyrimidin-5-yl]oxy-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(CC1)CN(C(C2)CC1=CC=C(C=C1)F)CCO WHBBMYHGXNWVMF-UHFFFAOYSA-N 0.000 claims 1
AUISEIWJSSIHQG-UHFFFAOYSA-N 5-fluoro-2-[4-[6-(oxan-4-ylamino)-2-azaspiro[3.3]heptan-2-yl]pyrimidin-5-yl]oxy-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(C1)CC(C2)NC1CCOCC1 AUISEIWJSSIHQG-UHFFFAOYSA-N 0.000 claims 1
CDXWIRFZLTYGNE-UHFFFAOYSA-N 5-fluoro-2-[4-[6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptan-2-yl]pyrimidin-5-yl]oxy-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(C1)CN(C2)CC1CCOCC1 CDXWIRFZLTYGNE-UHFFFAOYSA-N 0.000 claims 1
GYPGLCRLSSQMBB-UHFFFAOYSA-N 5-fluoro-2-[4-[6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzenesulfonamide Chemical compound FC=1C=CC(=C(C=1)S(=O)(=O)NC(C)C)OC=1C(=NC=NC=1)N1CC2(C1)CN(C2)CC1CCOCC1 GYPGLCRLSSQMBB-UHFFFAOYSA-N 0.000 claims 1
ZCCUPQFQNWWAMX-UHFFFAOYSA-N 5-fluoro-2-[4-[6-[methyl(oxan-4-yl)amino]-2-azaspiro[3.3]heptan-2-yl]pyrimidin-5-yl]oxy-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(C1)CC(C2)N(C1CCOCC1)C ZCCUPQFQNWWAMX-UHFFFAOYSA-N 0.000 claims 1
VABSEVGQINJLPF-UHFFFAOYSA-N 5-fluoro-2-[4-[7-(1H-indazol-6-ylmethyl)-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-methyl-N-propan-2-ylbenzamide Chemical compound N1N=CC2=CC=C(C=C12)CN1CC2(CCN(C2)C2=NC=NC=C2OC2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)CC1 VABSEVGQINJLPF-UHFFFAOYSA-N 0.000 claims 1
WONWPHOYKZIYHS-UHFFFAOYSA-N 5-fluoro-2-[4-[7-(2-hydroxy-2-methylpropyl)-2,7-diazaspiro[3.5]nonan-2-yl]pyrimidin-5-yl]oxy-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(C1)CCN(CC2)CC(C)(C)O WONWPHOYKZIYHS-UHFFFAOYSA-N 0.000 claims 1
BDIRBMQDGXJMJS-UHFFFAOYSA-N 5-fluoro-2-[4-[7-(oxan-4-ylmethyl)-2,7-diazaspiro[3.4]octan-2-yl]pyrimidin-5-yl]oxy-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(C1)CN(CC2)CC1CCOCC1 BDIRBMQDGXJMJS-UHFFFAOYSA-N 0.000 claims 1
INOLBPBMVUMEBU-UHFFFAOYSA-N 5-fluoro-2-[4-[7-(oxan-4-ylmethyl)-2,7-diazaspiro[3.5]nonan-2-yl]pyrimidin-5-yl]oxy-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(C1)CCN(CC2)CC1CCOCC1 INOLBPBMVUMEBU-UHFFFAOYSA-N 0.000 claims 1
CWUVQWYYRPWMBB-UHFFFAOYSA-N 5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 CWUVQWYYRPWMBB-UHFFFAOYSA-N 0.000 claims 1
PTEMNETVUDAXCR-UHFFFAOYSA-N 5-fluoro-2-[4-[7-[(4-hydroxycyclohexyl)methyl]-2,7-diazaspiro[3.4]octan-2-yl]pyrimidin-5-yl]oxy-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(C1)CN(CC2)CC1CCC(CC1)O PTEMNETVUDAXCR-UHFFFAOYSA-N 0.000 claims 1
QZDFWXVGTWKGFV-UHFFFAOYSA-N 5-fluoro-2-[4-[7-[(4-hydroxycyclohexyl)methyl]-2,7-diazaspiro[3.5]nonan-2-yl]pyrimidin-5-yl]oxy-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(C1)CCN(CC2)CC1CCC(CC1)O QZDFWXVGTWKGFV-UHFFFAOYSA-N 0.000 claims 1
PDMRPPGIKBWLPE-UHFFFAOYSA-N 5-fluoro-2-[4-[7-[3-(4-fluorophenyl)propanoyl]-2,7-diazaspiro[3.4]octan-2-yl]pyrimidin-5-yl]oxy-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(C1)CN(CC2)C(CCC1=CC=C(C=C1)F)=O PDMRPPGIKBWLPE-UHFFFAOYSA-N 0.000 claims 1
GJXWALQBKYCTGK-UHFFFAOYSA-N 5-fluoro-2-[4-[7-[[1-(2-hydroxyethyl)-2-oxo-3H-benzimidazol-5-yl]methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(N(C(N2)=O)CCO)C=C1 GJXWALQBKYCTGK-UHFFFAOYSA-N 0.000 claims 1
HZUOHKPZVFLKTC-UHFFFAOYSA-N 5-fluoro-2-[4-[7-[[1-(2-hydroxyethyl)-2-oxo-3H-benzimidazol-5-yl]methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-methyl-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(N(C(N2)=O)CCO)C=C1 HZUOHKPZVFLKTC-UHFFFAOYSA-N 0.000 claims 1
DSLXKSUJJVIYEY-UHFFFAOYSA-N 5-fluoro-2-[[4-[2-(2-hydroxy-2-methylpropyl)-2,7-diazaspiro[3.5]nonan-7-yl]pyrimidin-5-yl]amino]-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)NC=1C(=NC=NC=1)N1CCC2(CN(C2)CC(C)(C)O)CC1 DSLXKSUJJVIYEY-UHFFFAOYSA-N 0.000 claims 1
PVXHTSXXGVHLSK-UHFFFAOYSA-N 5-fluoro-N-(2-hydroxyethyl)-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)CCO)C=1)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 PVXHTSXXGVHLSK-UHFFFAOYSA-N 0.000 claims 1
SCCIRZFDSFOQNQ-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[4-[6-(oxan-4-ylamino)-2-azaspiro[3.3]heptan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(C1)CC(C2)NC1CCOCC1 SCCIRZFDSFOQNQ-UHFFFAOYSA-N 0.000 claims 1
IJYGRFKVMKLFIT-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[4-[6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(C1)CN(C2)CC1CCOCC1 IJYGRFKVMKLFIT-UHFFFAOYSA-N 0.000 claims 1
FLCRIJIGHCULJZ-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[4-[7-[(1-methyl-2-oxo-3H-benzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(N(C(N2)=O)C)C=C1 FLCRIJIGHCULJZ-UHFFFAOYSA-N 0.000 claims 1
IWXVKHMNGFDXBG-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-phenylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C2=CC=CC=C2)C)C=1)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 IWXVKHMNGFDXBG-UHFFFAOYSA-N 0.000 claims 1
LOZDROCUITWELZ-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzenesulfonamide Chemical compound FC=1C=CC(=C(C=1)S(=O)(=O)N(C)C(C)C)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 LOZDROCUITWELZ-UHFFFAOYSA-N 0.000 claims 1
KECNSCUDLQZSCQ-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[4-[7-[(2-oxo-3H-1,3-benzoxazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC=1C=CC2=C(NC(O2)=O)C=1 KECNSCUDLQZSCQ-UHFFFAOYSA-N 0.000 claims 1
ZLPDKRFWNNYPEL-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[4-[7-[(3-oxo-4H-1,4-benzoxazin-6-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(OCC(N2)=O)C=C1 ZLPDKRFWNNYPEL-UHFFFAOYSA-N 0.000 claims 1
KQJDDPDQKQBUOA-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[4-[7-[[3-(2-oxo-1,3-oxazolidin-3-yl)phenyl]methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC(=CC=C1)N1C(OCC1)=O KQJDDPDQKQBUOA-UHFFFAOYSA-N 0.000 claims 1
PFXYDBYVJDWJFS-UHFFFAOYSA-N 6-(1,4-dioxaspiro[4.5]decan-8-ylmethyl)-2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2,6-diazaspiro[3.3]heptane Chemical compound O1CCOC11CCC(CC1)CN1CC2(C1)CN(C2)C1=NC=NC=C1OC1=C(C=C(C=C1)F)C=1C(=NC=NC=1)C(C)C PFXYDBYVJDWJFS-UHFFFAOYSA-N 0.000 claims 1
UVQPSZLPCKENPW-UHFFFAOYSA-N 6-[(3,3-difluorocyclohexyl)methyl]-2-[5-[4-fluoro-2-(2-propan-2-ylpyrazol-3-yl)phenoxy]pyrimidin-4-yl]-2,6-diazaspiro[3.3]heptane Chemical compound FC1(CC(CCC1)CN1CC2(C1)CN(C2)C1=NC=NC=C1OC1=C(C=C(C=C1)F)C1=CC=NN1C(C)C)F UVQPSZLPCKENPW-UHFFFAOYSA-N 0.000 claims 1
KLIHLTVOEAUDIQ-UHFFFAOYSA-N 6-[(3,3-difluorocyclohexyl)methyl]-2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2,6-diazaspiro[3.3]heptane Chemical compound FC1(CC(CCC1)CN1CC2(C1)CN(C2)C1=NC=NC=C1OC1=C(C=C(C=C1)F)C=1C(=NC=NC=1)C(C)C)F KLIHLTVOEAUDIQ-UHFFFAOYSA-N 0.000 claims 1
FUSPMEDUXAOCBW-UHFFFAOYSA-N 6-[2-[6-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2,6-diazaspiro[3.3]heptan-2-yl]-2-oxoethyl]-3,3-dimethyl-1H-indol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CN(C3)C(CC3=CC=C4C(C(NC4=C3)=O)(C)C)=O)C2)C=C1)C=1C(=NC=NC=1)C(C)C FUSPMEDUXAOCBW-UHFFFAOYSA-N 0.000 claims 1
OJYJCIQNTXBNFR-UHFFFAOYSA-N 6-[[2-[5-(2-chloro-4-fluorophenoxy)pyrimidin-4-yl]-2,7-diazaspiro[3.4]octan-7-yl]methyl]-3,3-dimethyl-1H-indol-2-one Chemical compound ClC1=C(OC=2C(=NC=NC=2)N2CC3(C2)CN(CC3)CC2=CC=C3C(C(NC3=C2)=O)(C)C)C=CC(=C1)F OJYJCIQNTXBNFR-UHFFFAOYSA-N 0.000 claims 1
VCSCLDVKWJMCDS-UHFFFAOYSA-N 6-[[2-[5-(2-cyclopentyloxy-4-fluorophenoxy)pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-3,3-dimethyl-1H-indol-2-one Chemical compound C1(CCCC1)OC1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC=C4C(C(NC4=C3)=O)(C)C)CC2)C=CC(=C1)F VCSCLDVKWJMCDS-UHFFFAOYSA-N 0.000 claims 1
INCSCRYDUVLOJT-UHFFFAOYSA-N 6-[[2-[5-[2-(2-cyclopropylpyridin-3-yl)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-3,3-dimethyl-1H-indol-2-one Chemical compound C1(CC1)C1=NC=CC=C1C1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC=C4C(C(NC4=C3)=O)(C)C)CC2)C=CC(=C1)F INCSCRYDUVLOJT-UHFFFAOYSA-N 0.000 claims 1
NHICZQBAVCWWIY-UHFFFAOYSA-N 6-[[2-[5-[2-(3-cyclopropyl-1-methyl-6-oxopyridin-2-yl)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-3-(2-hydroxyethyl)-1H-benzimidazol-2-one Chemical compound C1(CC1)C1=C(N(C(C=C1)=O)C)C1=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC4=C(N(C(N4)=O)CCO)C=C3)CC2)C=CC(=C1)F NHICZQBAVCWWIY-UHFFFAOYSA-N 0.000 claims 1
PNOKNMMTSZCEKG-UHFFFAOYSA-N 6-[[2-[5-[4-fluoro-2-(1-hydroxy-2-methylpropyl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-3,3-dimethyl-1H-indol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC=C4C(C(NC4=C3)=O)(C)C)CC2)C=C1)C(C(C)C)O PNOKNMMTSZCEKG-UHFFFAOYSA-N 0.000 claims 1
YGZFWDHIPLCYKP-UHFFFAOYSA-N 6-[[2-[5-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-3,3-dimethyl-1H-indol-2-one Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC=C4C(C(NC4=C3)=O)(C)C)CC2)C=C1)OCC(F)(F)F YGZFWDHIPLCYKP-UHFFFAOYSA-N 0.000 claims 1
MAYRJOUTDCVLKH-UHFFFAOYSA-N 6-[[2-[5-[4-fluoro-2-(2-methylpropanoyl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]-3-methyl-2-oxo-1H-indole-3-carbonitrile Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(CCN(C3)CC3=CC=C4C(C(NC4=C3)=O)(C#N)C)CC2)C=C1)C(C(C)C)=O MAYRJOUTDCVLKH-UHFFFAOYSA-N 0.000 claims 1
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WTOWWBGFWPNCFC-UHFFFAOYSA-N 7-(6-fluoro-3,4-dihydro-1H-isoquinolin-2-yl)-2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-5-oxa-2-azaspiro[3.4]octane Chemical compound FC1=CC(=C(OC=2C(=NC=NC=2)N2CC3(C2)OCC(C3)N2CC3=CC=C(C=C3CC2)F)C=C1)C=1C(=NC=NC=1)C(C)C WTOWWBGFWPNCFC-UHFFFAOYSA-N 0.000 claims 1
KZPYNTRMKJGOMH-UHFFFAOYSA-N 8-benzyl-2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2-azaspiro[4.4]nonane Chemical compound C(C1=CC=CC=C1)C1CC2(CCN(C2)C2=NC=NC=C2OC2=C(C=C(C=C2)F)C=2C(=NC=NC=2)C(C)C)CC1 KZPYNTRMKJGOMH-UHFFFAOYSA-N 0.000 claims 1
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WHPFSQCUTHZOAW-UHFFFAOYSA-N N,N-diethyl-5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxybenzamide Chemical compound C(C)N(C(C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1)=O)CC WHPFSQCUTHZOAW-UHFFFAOYSA-N 0.000 claims 1
NWBWDFYKIBFWDH-UHFFFAOYSA-N N-(2-amino-2-oxoethyl)-N-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]-2-methylpropanamide Chemical compound NC(CN(C(C(C)C)=O)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1)=O NWBWDFYKIBFWDH-UHFFFAOYSA-N 0.000 claims 1
LWRGKSPITKMWLO-UHFFFAOYSA-N N-(cyclohexylmethyl)-2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-5-oxa-2-azaspiro[3.4]octan-7-amine Chemical compound C1(CCCCC1)CNC1COC2(CN(C2)C2=NC=NC=C2OC2=C(C=C(C=C2)F)C=2C(=NC=NC=2)C(C)C)C1 LWRGKSPITKMWLO-UHFFFAOYSA-N 0.000 claims 1
PXJPRVURMSQXEI-UHFFFAOYSA-N N-[2-(2-ethylphenyl)-4-fluorophenyl]-4-[2-(2-methylpropyl)-2,7-diazaspiro[3.5]nonan-7-yl]pyrimidin-5-amine Chemical compound C(C)C1=C(C=CC=C1)C1=C(C=CC(=C1)F)NC=1C(=NC=NC=1)N1CCC2(CN(C2)CC(C)C)CC1 PXJPRVURMSQXEI-UHFFFAOYSA-N 0.000 claims 1
APNGVIKAXKGLIL-UHFFFAOYSA-N N-[2-[4-[2-(5-bromo-2,3-dihydro-1H-indene-2-carbonyl)-2,6-diazaspiro[3.3]heptan-6-yl]pyrimidin-5-yl]oxy-5-fluorophenyl]-N-ethyl-2-methylpropanamide Chemical compound BrC=1C=C2CC(CC2=CC=1)C(=O)N1CC2(CN(C2)C2=NC=NC=C2OC2=C(C=C(C=C2)F)N(C(C(C)C)=O)CC)C1 APNGVIKAXKGLIL-UHFFFAOYSA-N 0.000 claims 1
YYKNNGFNSHQRJR-UHFFFAOYSA-N N-[2-[4-[7-[(4,4-difluorocyclohexyl)methyl]-2,7-diazaspiro[3.4]octan-2-yl]pyrimidin-5-yl]oxy-5-fluorophenyl]-N-ethyl-2-methylpropanamide Chemical compound FC1(CCC(CC1)CN1CC2(CN(C2)C2=NC=NC=C2OC2=C(C=C(C=C2)F)N(C(C(C)C)=O)CC)CC1)F YYKNNGFNSHQRJR-UHFFFAOYSA-N 0.000 claims 1
PSQHIQPBUJURRB-UHFFFAOYSA-N N-[2-chloro-4-[[2-[5-[2-(4-cyano-2-cyclopropylphenyl)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]phenyl]acetamide Chemical compound ClC1=C(C=CC(=C1)CN1CC2(CC1)CN(CC2)C1=NC=NC=C1OC1=C(C=C(C=C1)F)C1=C(C=C(C=C1)C#N)C1CC1)NC(C)=O PSQHIQPBUJURRB-UHFFFAOYSA-N 0.000 claims 1
IESFOJCWDGZWKO-UHFFFAOYSA-N N-[4-[[2-[5-[2-(3-cyclopropyl-1-methyl-6-oxopyridin-2-yl)-4-fluorophenoxy]pyrimidin-4-yl]-2,7-diazaspiro[3.5]nonan-7-yl]methyl]cyclohexyl]methanesulfonamide Chemical compound C1(CC1)C1=C(N(C(C=C1)=O)C)C1=C(OC=2C(=NC=NC=2)N2CC3(C2)CCN(CC3)CC2CCC(CC2)NS(=O)(=O)C)C=CC(=C1)F IESFOJCWDGZWKO-UHFFFAOYSA-N 0.000 claims 1
VYXXRMOZMLTDAD-UHFFFAOYSA-N N-[4-[[2-[5-[4-fluoro-2-(2-propan-2-ylphenyl)phenoxy]pyrimidin-4-yl]-2,7-diazaspiro[4.4]nonan-7-yl]methyl]phenyl]acetamide Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(C)C)OC=1C(=NC=NC=1)N1CC2(CCN(C2)CC2=CC=C(C=C2)NC(C)=O)CC1 VYXXRMOZMLTDAD-UHFFFAOYSA-N 0.000 claims 1
WGYNMRXZMYENDV-UHFFFAOYSA-N N-[4-fluoro-2-(2-propan-2-yloxyphenyl)phenyl]-4-[2-(2-methylpropyl)-2,7-diazaspiro[3.5]nonan-7-yl]pyrimidin-5-amine Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)OC(C)C)NC=1C(=NC=NC=1)N1CCC2(CN(C2)CC(C)C)CC1 WGYNMRXZMYENDV-UHFFFAOYSA-N 0.000 claims 1
SNVLHFUGTAYLNA-UHFFFAOYSA-N N-[4-fluoro-2-(2-propan-2-ylphenyl)phenyl]-4-[2-(2-methylpropyl)-2,7-diazaspiro[3.5]nonan-7-yl]pyrimidin-5-amine Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(C)C)NC=1C(=NC=NC=1)N1CCC2(CN(C2)CC(C)C)CC1 SNVLHFUGTAYLNA-UHFFFAOYSA-N 0.000 claims 1
VDYYFJFEOKBADM-UHFFFAOYSA-N N-[4-fluoro-2-(2-propan-2-ylphenyl)phenyl]-4-[6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptan-2-yl]pyridin-3-amine Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(C)C)NC=1C=NC=CC=1N1CC2(C1)CN(C2)CC1CCOCC1 VDYYFJFEOKBADM-UHFFFAOYSA-N 0.000 claims 1
ZJZNUZMREULUSW-UHFFFAOYSA-N N-[4-fluoro-2-(2-propan-2-ylphenyl)phenyl]-4-[6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptan-2-yl]pyrimidin-5-amine Chemical compound FC=1C=CC(=C(C=1)C1=C(C=CC=C1)C(C)C)NC=1C(=NC=NC=1)N1CC2(C1)CN(C2)CC1CCOCC1 ZJZNUZMREULUSW-UHFFFAOYSA-N 0.000 claims 1
GRZUBBXSKZGFAD-UHFFFAOYSA-N N-[4-fluoro-2-(3-methyl-5-propan-2-yl-1,2-oxazol-4-yl)phenyl]-4-[6-(oxan-4-ylmethyl)-2,6-diazaspiro[3.3]heptan-2-yl]pyrimidin-5-amine Chemical compound FC1=CC(=C(C=C1)NC=1C(=NC=NC=1)N1CC2(C1)CN(C2)CC1CCOCC1)C=1C(=NOC=1C(C)C)C GRZUBBXSKZGFAD-UHFFFAOYSA-N 0.000 claims 1
URPFGIPNAALXRQ-UHFFFAOYSA-N N-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]-2-methyl-N-(2,2,2-trifluoroethyl)propanamide Chemical compound FC=1C=CC(=C(C=1)N(C(C(C)C)=O)CC(F)(F)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 URPFGIPNAALXRQ-UHFFFAOYSA-N 0.000 claims 1
FIYBYPKMZFOFAF-UHFFFAOYSA-N N-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]-N,2-dimethylpropanamide Chemical compound FC=1C=CC(=C(C=1)N(C(C(C)C)=O)C)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 FIYBYPKMZFOFAF-UHFFFAOYSA-N 0.000 claims 1
IOBPWSLYXMKLHJ-UHFFFAOYSA-N N-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]-N-(2-hydroxyethyl)-2-methylpropanamide Chemical compound FC=1C=CC(=C(C=1)N(C(C(C)C)=O)CCO)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 IOBPWSLYXMKLHJ-UHFFFAOYSA-N 0.000 claims 1
KPKNZVCLBVKEDR-UHFFFAOYSA-N N-[cyclopentyl-[5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxyphenyl]methyl]acetamide Chemical compound C1(CCCC1)C(NC(C)=O)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1 KPKNZVCLBVKEDR-UHFFFAOYSA-N 0.000 claims 1
RZAXYODJPAWNIG-UHFFFAOYSA-N N-benzyl-2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-5-oxa-2-azaspiro[3.4]octan-7-amine Chemical compound C(C1=CC=CC=C1)NC1COC2(CN(C2)C2=NC=NC=C2OC2=C(C=C(C=C2)F)C=2C(=NC=NC=2)C(C)C)C1 RZAXYODJPAWNIG-UHFFFAOYSA-N 0.000 claims 1
QDKWKJDZNABBGB-UHFFFAOYSA-N N-cyclopropyl-5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzamide Chemical compound C1(CC1)N(C(C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1)=O)C(C)C QDKWKJDZNABBGB-UHFFFAOYSA-N 0.000 claims 1
NMQZWUXYVQZUOR-UHFFFAOYSA-N N-ethyl-5-fluoro-2-[4-[7-[(1-methyl-2-oxo-3H-benzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzamide Chemical compound C(C)N(C(C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(N(C(N2)=O)C)C=C1)=O)C(C)C NMQZWUXYVQZUOR-UHFFFAOYSA-N 0.000 claims 1
OYVZKQBYSNIDHR-UHFFFAOYSA-N N-ethyl-5-fluoro-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzamide Chemical compound C(C)N(C(C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1)=O)C(C)C OYVZKQBYSNIDHR-UHFFFAOYSA-N 0.000 claims 1
OKCZZNOQHLBWCT-UHFFFAOYSA-N N-ethyl-5-fluoro-2-[4-[7-[[1-(2-hydroxyethyl)-2-oxo-3H-benzimidazol-5-yl]methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxy-N-propan-2-ylbenzamide Chemical compound C(C)N(C(C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(N(C(N2)=O)CCO)C=C1)=O)C(C)C OKCZZNOQHLBWCT-UHFFFAOYSA-N 0.000 claims 1
SBPXFEWSIYVTMR-UHFFFAOYSA-N N-ethyl-N-[5-fluoro-2-[4-[2-[2-(4-methylsulfonylphenyl)acetyl]-2,6-diazaspiro[3.3]heptan-6-yl]pyrimidin-5-yl]oxyphenyl]-2-methylpropanamide Chemical compound C(C)N(C(C(C)C)=O)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(C1)CN(C2)C(CC1=CC=C(C=C1)S(=O)(=O)C)=O SBPXFEWSIYVTMR-UHFFFAOYSA-N 0.000 claims 1
JJQFVRZQDUZZTH-UHFFFAOYSA-N N-ethyl-N-[5-fluoro-2-[4-[7-(2-methylpropyl)-2,7-diazaspiro[3.4]octan-2-yl]pyrimidin-5-yl]oxyphenyl]-2-methylpropanamide Chemical compound C(C)N(C(C(C)C)=O)C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(C1)CN(CC2)CC(C)C JJQFVRZQDUZZTH-UHFFFAOYSA-N 0.000 claims 1
KEIJIJYZSFBZBO-UHFFFAOYSA-N N-tert-butyl-2-[5-[4-fluoro-2-(4-propan-2-ylpyrimidin-5-yl)phenoxy]pyrimidin-4-yl]-2-azaspiro[3.4]octan-6-amine Chemical compound C(C)(C)(C)NC1CC2(CN(C2)C2=NC=NC=C2OC2=C(C=C(C=C2)F)C=2C(=NC=NC=2)C(C)C)CC1 KEIJIJYZSFBZBO-UHFFFAOYSA-N 0.000 claims 1
PUGADVGRQHATNY-UHFFFAOYSA-N N-tert-butyl-5-fluoro-N-methyl-2-[4-[7-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]pyrimidin-5-yl]oxybenzamide Chemical compound C(C)(C)(C)N(C(C1=C(C=CC(=C1)F)OC=1C(=NC=NC=1)N1CC2(CC1)CN(CC2)CC1=CC2=C(NC(N2)=O)C=C1)=O)C PUGADVGRQHATNY-UHFFFAOYSA-N 0.000 claims 1
208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
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208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 claims 1
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208000033559 Waldenström macroglobulinemia Diseases 0.000 claims 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 1
229910052786 argon Inorganic materials 0.000 claims 1
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201000002797 childhood leukemia Diseases 0.000 claims 1
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239000013078 crystal Chemical group 0.000 claims 1
201000007241 cutaneous T cell lymphoma Diseases 0.000 claims 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 claims 1
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201000001421 hyperglycemia Diseases 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
150000004682 monohydrates Chemical class 0.000 claims 1
HBXNJMZWGSCKPW-UHFFFAOYSA-N octan-2-amine Chemical compound CCCCCCC(C)N HBXNJMZWGSCKPW-UHFFFAOYSA-N 0.000 claims 1
125000004043 oxo group Chemical group O=* 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
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SJMCLWCCNYAWRQ-UHFFFAOYSA-N propane-2-sulfonamide Chemical compound CC(C)S(N)(=O)=O SJMCLWCCNYAWRQ-UHFFFAOYSA-N 0.000 claims 1
108090000623 proteins and genes Proteins 0.000 claims 1
FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
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JP2018564288A 2016-06-10 2017-06-08 メニン－ｍｌｌ相互作用の阻害剤 Active JP7007302B2 (ja)