JP2019517548A5 - - Google Patents
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- Publication number
- JP2019517548A5 JP2019517548A5 JP2018564288A JP2018564288A JP2019517548A5 JP 2019517548 A5 JP2019517548 A5 JP 2019517548A5 JP 2018564288 A JP2018564288 A JP 2018564288A JP 2018564288 A JP2018564288 A JP 2018564288A JP 2019517548 A5 JP2019517548 A5 JP 2019517548A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidin
- methyl
- diazaspiro
- fluoro
- oxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 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
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| AR104020A1 (es) | 2015-06-04 | 2017-06-21 | Kura Oncology Inc | Métodos y composiciones para inhibir la interacción de menina con proteínas mill |
| WO2016197027A1 (en) | 2015-06-04 | 2016-12-08 | Kura Oncology, Inc. | Methods and compositions for inhibiting the interaction of menin with mll proteins |
| EP4643952A3 (en) | 2016-01-26 | 2026-01-14 | Memorial Sloan Kettering Cancer Center | Targeting chromatin regulators for inhibiting leukemogenic gene expression in npm1 |
| CN109640987B (zh) | 2016-03-16 | 2022-12-02 | 库拉肿瘤学公司 | Menin-mll的桥联双环抑制剂及使用方法 |
| CN109152784B (zh) | 2016-03-16 | 2021-12-28 | 库拉肿瘤学公司 | 经取代的menin-mll抑制剂及使用方法 |
| WO2017192543A1 (en) | 2016-05-02 | 2017-11-09 | Regents Of The University Of Michigan | Piperidines as menin inhibitors |
| EP3805215A1 (en) * | 2016-06-10 | 2021-04-14 | Vitae Pharmaceuticals, LLC | Inhibitors of the menin-mll interaction |
| US12084462B2 (en) | 2016-09-14 | 2024-09-10 | Janssen Pharmaceutica Nv | Spiro bicyclic inhibitors of menin-MLL interaction |
| CN109689663B (zh) | 2016-09-14 | 2023-04-14 | 詹森药业有限公司 | Menin-mll相互作用的螺二环抑制剂 |
| MA46228A (fr) | 2016-09-14 | 2019-07-24 | Janssen Pharmaceutica Nv | Inhibiteurs bicycliques fusionnés de l'interaction ménine-mll |
| BR112019012106A2 (pt) | 2016-12-15 | 2019-10-29 | Janssen Pharmaceutica Nv | inibidores de azepano de interação menin-mill |
| CN110691779B (zh) | 2017-03-24 | 2023-10-10 | 库拉肿瘤学公司 | 治疗血液系统恶性肿瘤和尤因肉瘤的方法 |
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