JP5649643B2 - ピリミジン化合物、ｍＴＯＲキナーゼおよびＰＩ３キナーゼ阻害剤としてのそれらの使用、ならびにそれらの合成 - Google Patents

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Publication number

JP5649643B2

JP5649643B2 JP2012506209A JP2012506209A JP5649643B2 JP 5649643 B2 JP5649643 B2 JP 5649643B2 JP 2012506209 A JP2012506209 A JP 2012506209A JP 2012506209 A JP2012506209 A JP 2012506209A JP 5649643 B2 JP5649643 B2 JP 5649643B2

Authority

JP

Japan

Prior art keywords

phenyl

azabicyclo

oxa

alkyl

oct

Prior art date

2009-04-17

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 230000015572 biosynthetic process Effects 0.000 title description 29
• 238000003786 synthesis reaction Methods 0.000 title description 18
• 239000003628 mammalian target of rapamycin inhibitor Substances 0.000 title description 10
• 150000003230 pyrimidines Chemical class 0.000 title description 4
• 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 title description 2
• -1 amino - Chemical class 0.000 claims description 385
• 150000001875 compounds Chemical class 0.000 claims description 229
• 239000000203 mixture Substances 0.000 claims description 153
• 125000000623 heterocyclic group Chemical group 0.000 claims description 80
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 78
• 125000000217 alkyl group Chemical group 0.000 claims description 70
• 238000000034 method Methods 0.000 claims description 68
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
• 125000003118 aryl group Chemical group 0.000 claims description 62
• 108091007960 PI3Ks Proteins 0.000 claims description 59
• 102000038030 PI3Ks Human genes 0.000 claims description 59
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 51
• 239000004202 carbamide Substances 0.000 claims description 51
• 229910052757 nitrogen Inorganic materials 0.000 claims description 51
• 125000001072 heteroaryl group Chemical group 0.000 claims description 49
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 45
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
• 150000003839 salts Chemical class 0.000 claims description 39
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 35
• 229910052736 halogen Inorganic materials 0.000 claims description 35
• 125000001424 substituent group Chemical group 0.000 claims description 35
• 150000002367 halogens Chemical class 0.000 claims description 34
• HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• 125000005518 carboxamido group Chemical group 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 16
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
• 125000002252 acyl group Chemical group 0.000 claims description 13
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 12
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 12
• 206010038389 Renal cancer Diseases 0.000 claims description 12
• 201000010982 kidney cancer Diseases 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 11
• 206010060862 Prostate cancer Diseases 0.000 claims description 11
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 11
• 150000001408 amides Chemical class 0.000 claims description 11
• 206010033128 Ovarian cancer Diseases 0.000 claims description 10
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
• 206010006187 Breast cancer Diseases 0.000 claims description 9
• 208000026310 Breast neoplasm Diseases 0.000 claims description 9
• 206010009944 Colon cancer Diseases 0.000 claims description 9
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 9
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 8
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
• 208000029742 colonic neoplasm Diseases 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 201000005202 lung cancer Diseases 0.000 claims description 8
• 208000020816 lung neoplasm Diseases 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 239000011593 sulfur Chemical group 0.000 claims description 8
• NFTWCDZRJTYOEI-UHFFFAOYSA-N 1-[4-[4-[(dimethylamino)methyl]-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CN(C)C)=CC(N2C3CCC2COC3)=N1 NFTWCDZRJTYOEI-UHFFFAOYSA-N 0.000 claims description 7
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 7
• 206010005003 Bladder cancer Diseases 0.000 claims description 7
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 7
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 7
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 7
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 7
• 208000002495 Uterine Neoplasms Diseases 0.000 claims description 7
• 125000003368 amide group Chemical group 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 206010017758 gastric cancer Diseases 0.000 claims description 7
• 208000032839 leukemia Diseases 0.000 claims description 7
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 7
• 201000002528 pancreatic cancer Diseases 0.000 claims description 7
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 201000000849 skin cancer Diseases 0.000 claims description 7
• 201000011549 stomach cancer Diseases 0.000 claims description 7
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 7
• 206010046766 uterine cancer Diseases 0.000 claims description 7
• FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims description 6
• QXFLWKCCFOARLQ-UHFFFAOYSA-N 4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(oxan-4-yl)pyrimidin-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NC(C2CCOCC2)=CC(N2C3CCC2COC3)=N1 QXFLWKCCFOARLQ-UHFFFAOYSA-N 0.000 claims description 6
• DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 claims description 6
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 6
• 229930012538 Paclitaxel Natural products 0.000 claims description 6
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims description 6
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 6
• 229960003901 dacarbazine Drugs 0.000 claims description 6
• 229960004679 doxorubicin Drugs 0.000 claims description 6
• 229960005420 etoposide Drugs 0.000 claims description 6
• VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 229960001592 paclitaxel Drugs 0.000 claims description 6
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 6
• OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims description 6
• 229960004528 vincristine Drugs 0.000 claims description 6
• OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims description 6
• SQGJVUOODZLQPA-UHFFFAOYSA-N 2-(4-aminophenyl)-n,n-diethyl-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-4-amine Chemical compound N=1C(N(CC)CC)=CC(N2C3CCC2COC3)=NC=1C1=CC=C(N)C=C1 SQGJVUOODZLQPA-UHFFFAOYSA-N 0.000 claims description 5
• XIMQPYNOCHKLJW-UHFFFAOYSA-N 4-[2-chloro-6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-4-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC(N2CC3CCC(O3)C2)=NC(Cl)=N1 XIMQPYNOCHKLJW-UHFFFAOYSA-N 0.000 claims description 5
• HSZHEUMJJBLBPN-UHFFFAOYSA-N 4-[4-[(dimethylamino)methyl]-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]aniline Chemical compound N=1C(CN(C)C)=CC(N2C3CCC2COC3)=NC=1C1=CC=C(N)C=C1 HSZHEUMJJBLBPN-UHFFFAOYSA-N 0.000 claims description 5
• MZOUXMYXXPPSIH-UHFFFAOYSA-N 4-[4-chloro-6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NC(Cl)=CC(N2CC3CCC(O3)C2)=N1 MZOUXMYXXPPSIH-UHFFFAOYSA-N 0.000 claims description 5
• VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 5
• 229960004562 carboplatin Drugs 0.000 claims description 5
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 5
• 229960004316 cisplatin Drugs 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• VZOLOHQFPGWQRU-UHFFFAOYSA-N 1-[4-[4-[(dimethylamino)methyl]-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]-3-pyridin-3-ylurea Chemical compound N=1C(CN(C)C)=CC(N2C3CCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CN=C1 VZOLOHQFPGWQRU-UHFFFAOYSA-N 0.000 claims description 4
• ULYMNVDCMXERKG-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[4-[(dimethylamino)methyl]-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CN(C)C)=CC(N2C3CCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC1CC1 ULYMNVDCMXERKG-UHFFFAOYSA-N 0.000 claims description 4
• BXCQNBRVRCGRJP-UHFFFAOYSA-N 2-(4-aminophenyl)-6-(3,7-dioxa-9-azabicyclo[3.3.1]nonan-9-yl)-n-propan-2-ylpyrimidin-4-amine Chemical compound N=1C(NC(C)C)=CC(N2C3COCC2COC3)=NC=1C1=CC=C(N)C=C1 BXCQNBRVRCGRJP-UHFFFAOYSA-N 0.000 claims description 4
• WJNIYOBFNKKNJY-UHFFFAOYSA-N 2-(4-aminophenyl)-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-n-(oxan-4-yl)pyrimidin-4-amine Chemical class C1=CC(N)=CC=C1C1=NC(NC2CCOCC2)=CC(N2C3CCC2COC3)=N1 WJNIYOBFNKKNJY-UHFFFAOYSA-N 0.000 claims description 4
• NGDQYJVFOAGFBX-UHFFFAOYSA-N 2-(4-aminophenyl)-n-(2-methylsulfonylethyl)-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-4-amine Chemical compound N=1C(NCCS(=O)(=O)C)=CC(N2C3CCC2COC3)=NC=1C1=CC=C(N)C=C1 NGDQYJVFOAGFBX-UHFFFAOYSA-N 0.000 claims description 4
• CWOPCOPFSBNRIU-UHFFFAOYSA-N 2-(4-nitrophenyl)-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-n-(oxan-4-yl)pyrimidin-4-amine Chemical class C1=CC([N+](=O)[O-])=CC=C1C1=NC(NC2CCOCC2)=CC(N2C3CCC2COC3)=N1 CWOPCOPFSBNRIU-UHFFFAOYSA-N 0.000 claims description 4
• PHHARNYBZKPRKJ-UHFFFAOYSA-N 4-[4,6-bis(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NC(N2C3CCC2COC3)=CC(N2C3CCC2COC3)=N1 PHHARNYBZKPRKJ-UHFFFAOYSA-N 0.000 claims description 4
• ZEMZGYACMUNMOJ-UHFFFAOYSA-N 4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NC=CC(N2CC3CCC(O3)C2)=N1 ZEMZGYACMUNMOJ-UHFFFAOYSA-N 0.000 claims description 4
• UNTFOCYFKAVCST-UHFFFAOYSA-N 8-[2-(4-nitrophenyl)-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-4-yl]-3-oxa-8-azabicyclo[3.2.1]octane Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NC(N2C3CCC2COC3)=CC(N2C3CCC2COC3)=N1 UNTFOCYFKAVCST-UHFFFAOYSA-N 0.000 claims description 4
• ZXKMZSAHTOKHJI-UHFFFAOYSA-N 8-[6-(3,6-dihydro-2h-pyran-4-yl)-2-(4-nitrophenyl)pyrimidin-4-yl]-3-oxa-8-azabicyclo[3.2.1]octane Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NC(N2C3CCC2COC3)=CC(C=2CCOCC=2)=N1 ZXKMZSAHTOKHJI-UHFFFAOYSA-N 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 229960000397 bevacizumab Drugs 0.000 claims description 4
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 230000002194 synthesizing effect Effects 0.000 claims description 4
• RAPBIAHQVIOWPO-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)phenyl]-3-[4-[4-(2-methylsulfonylethylamino)-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(NCCS(C)(=O)=O)N=2)N2C3CCC2COC3)C=C1 RAPBIAHQVIOWPO-UHFFFAOYSA-N 0.000 claims description 3
• SCKDCMSXGUNGGN-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)phenyl]-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(oxan-4-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(N=2)C2CCOCC2)N2C3CCC2COC3)C=C1 SCKDCMSXGUNGGN-UHFFFAOYSA-N 0.000 claims description 3
• FHFDYBWIDIXYCI-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)phenyl]-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(oxan-4-ylamino)pyrimidin-2-yl]phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(NC3CCOCC3)N=2)N2C3CCC2COC3)C=C1 FHFDYBWIDIXYCI-UHFFFAOYSA-N 0.000 claims description 3
• BMPYDDABCASHFX-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)phenyl]-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(propan-2-ylamino)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(NC(C)C)=CC(N2C3CCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCN(C)CC1 BMPYDDABCASHFX-UHFFFAOYSA-N 0.000 claims description 3
• KKXDPQYILLDQKY-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)phenyl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(propan-2-ylamino)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(NC(C)C)=CC(N2CC3CCC(O3)C2)=NC=1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCN(C)CC1 KKXDPQYILLDQKY-UHFFFAOYSA-N 0.000 claims description 3
• JMLPNBMXEGXMIK-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)phenyl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-phenylpyrimidin-2-yl]phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(N=2)N2CC3CCC(O3)C2)C=2C=CC=CC=2)C=C1 JMLPNBMXEGXMIK-UHFFFAOYSA-N 0.000 claims description 3
• QZSSDNWWOFUUDE-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)phenyl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-propan-2-yloxypyrimidin-2-yl]phenyl]urea Chemical compound N=1C(OC(C)C)=CC(N2CC3CCC(O3)C2)=NC=1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCN(C)CC1 QZSSDNWWOFUUDE-UHFFFAOYSA-N 0.000 claims description 3
• ZFZQZGXIKOYTOA-UHFFFAOYSA-N 1-[4-(4-methylpiperazine-1-carbonyl)phenyl]-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(oxan-4-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(N=2)C2CCOCC2)N2C3CCC2COC3)C=C1 ZFZQZGXIKOYTOA-UHFFFAOYSA-N 0.000 claims description 3
• OCKRNKTUOCUOOL-UHFFFAOYSA-N 1-[4-(hydroxymethyl)phenyl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-phenylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(CO)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(N=2)N2CC3CCC(O3)C2)C=2C=CC=CC=2)C=C1 OCKRNKTUOCUOOL-UHFFFAOYSA-N 0.000 claims description 3
• YKZAMPNYYULFDZ-UHFFFAOYSA-N 1-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-3-[4-[4-(2-methylsulfonylethylamino)-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(NCCS(C)(=O)=O)N=2)N2C3CCC2COC3)C=C1 YKZAMPNYYULFDZ-UHFFFAOYSA-N 0.000 claims description 3
• KHQMDCIOBKJYLM-UHFFFAOYSA-N 1-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(oxan-4-ylamino)pyrimidin-2-yl]phenyl]urea Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(NC3CCOCC3)N=2)N2C3CCC2COC3)C=C1 KHQMDCIOBKJYLM-UHFFFAOYSA-N 0.000 claims description 3
• HNUOTHSWOFUZDQ-UHFFFAOYSA-N 1-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(propan-2-ylamino)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(NC(C)C)=CC(N2C3CCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1CN1CCN(C)CC1 HNUOTHSWOFUZDQ-UHFFFAOYSA-N 0.000 claims description 3
• ZIGVACZFWLXSMM-UHFFFAOYSA-N 1-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-3-[4-[4-(methylsulfonylmethyl)-6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2CC3CCC(O3)C2)C=C1 ZIGVACZFWLXSMM-UHFFFAOYSA-N 0.000 claims description 3
• VLTMWLMLGJLQKO-NBAFEDJBSA-N 1-[4-[(dimethylamino)methyl]phenyl]-3-[4-[4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(N=1)=CC(N2C3CCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(CN(C)C)C=C1 VLTMWLMLGJLQKO-NBAFEDJBSA-N 0.000 claims description 3
• PNXKMGGQZSNGAF-UHFFFAOYSA-N 1-[4-[2,6-bis(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-4-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=CC(N2CC3CCC(O3)C2)=NC(N2CC3CCC(O3)C2)=N1 PNXKMGGQZSNGAF-UHFFFAOYSA-N 0.000 claims description 3
• WETQGLFSZCYBNE-UHFFFAOYSA-N 1-[4-[2,6-bis(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-4-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(C=2N=C(N=C(C=2)N2CC3CCC(O3)C2)N2CC3CCC(O3)C2)C=CC=1NC(=O)NC1=CC=NC=C1 WETQGLFSZCYBNE-UHFFFAOYSA-N 0.000 claims description 3
• HLYRZHYTIUUBTK-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(oxan-4-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(N=2)C2CCOCC2)N2C3CCC2COC3)C=C1 HLYRZHYTIUUBTK-UHFFFAOYSA-N 0.000 claims description 3
• ZQXRPEIMEQMZCV-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(oxan-4-ylamino)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(NC3CCOCC3)N=2)N2C3CCC2COC3)C=C1 ZQXRPEIMEQMZCV-UHFFFAOYSA-N 0.000 claims description 3
• ITUZFFHGDZXIEI-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(propan-2-ylamino)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(NC(C)C)=CC(N2C3CCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(OCCN(C)C)C=C1 ITUZFFHGDZXIEI-UHFFFAOYSA-N 0.000 claims description 3
• ILQOEBUYZVFXKN-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-phenylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(N=2)N2CC3CCC(O3)C2)C=2C=CC=CC=2)C=C1 ILQOEBUYZVFXKN-UHFFFAOYSA-N 0.000 claims description 3
• XNVFFWGVLCRZOY-CFSFKAJLSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-3-[4-[4-[(3r)-3-methylmorpholin-4-yl]-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@@H]1COCCN1C1=CC(N2C3CCC2COC3)=NC(C=2C=CC(NC(=O)NC=3C=CC(OCCN(C)C)=CC=3)=CC=2)=N1 XNVFFWGVLCRZOY-CFSFKAJLSA-N 0.000 claims description 3
• NPOKMPDLGIERFN-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-3-[4-[4-[(dimethylamino)methyl]-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(CN(C)C)N=2)N2C3CCC2COC3)C=C1 NPOKMPDLGIERFN-UHFFFAOYSA-N 0.000 claims description 3
• VPYSCOKTULUDBH-UHFFFAOYSA-N 1-[4-[4,6-bis(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(N=2)N2C3CCC2COC3)N2C3CCC2COC3)C=C1 VPYSCOKTULUDBH-UHFFFAOYSA-N 0.000 claims description 3
• TWCYOHWDJQPJDE-UHFFFAOYSA-N 1-[4-[4,6-bis(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]-3-[4-(4-methylpiperazine-1-carbonyl)phenyl]urea Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(N=2)N2C3CCC2COC3)N2C3CCC2COC3)C=C1 TWCYOHWDJQPJDE-UHFFFAOYSA-N 0.000 claims description 3
• DFYHVOICVNPMEV-UHFFFAOYSA-N 1-[4-[4,6-bis(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]-3-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]urea Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(N=2)N2C3CCC2COC3)N2C3CCC2COC3)C=C1 DFYHVOICVNPMEV-UHFFFAOYSA-N 0.000 claims description 3
• FQGVFACERCUPII-UHFFFAOYSA-N 1-[4-[4,6-bis(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]-3-[4-[2-(dimethylamino)ethoxy]phenyl]urea Chemical compound C1=CC(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(N=2)N2C3CCC2COC3)N2C3CCC2COC3)C=C1 FQGVFACERCUPII-UHFFFAOYSA-N 0.000 claims description 3
• LIOLZGXVKSOBFQ-UHFFFAOYSA-N 1-[4-[4,6-bis(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C=1C=C(C=2N=C(C=C(N=2)N2C3CCC2COC3)N2C3CCC2COC3)C=CC=1NC(=O)NC1=CC=CN=C1 LIOLZGXVKSOBFQ-UHFFFAOYSA-N 0.000 claims description 3
• JXIFVQLKNIJYAR-UHFFFAOYSA-N 1-[4-[4,6-bis(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(C=2N=C(C=C(N=2)N2C3CCC2COC3)N2C3CCC2COC3)C=CC=1NC(=O)NC1=CC=NC=C1 JXIFVQLKNIJYAR-UHFFFAOYSA-N 0.000 claims description 3
• NYHMBSZNLABDHQ-UHFFFAOYSA-N 1-[4-[4,6-bis(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl]phenyl]-1-ethyl-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound C=1C=C(C=2N=C(C=C(N=2)N2CC3CCC(O3)C2)N2CC3CCC(O3)C2)C=CC=1N(CC)C(=O)NC(C=C1)=CC=C1N1CCN(C)CC1 NYHMBSZNLABDHQ-UHFFFAOYSA-N 0.000 claims description 3
• APIVDKUDTYSGEC-UHFFFAOYSA-N 1-[4-[4,6-bis(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl]phenyl]-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(N=2)N2CC3CCC(O3)C2)N2CC3CCC(O3)C2)C=C1 APIVDKUDTYSGEC-UHFFFAOYSA-N 0.000 claims description 3
• WWXQFPSJFZXHEE-UHFFFAOYSA-N 1-[4-[4,6-bis(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=CC(N2CC3CCC(O3)C2)=N1 WWXQFPSJFZXHEE-UHFFFAOYSA-N 0.000 claims description 3
• HQDFRJIZSFCGMB-UHFFFAOYSA-N 1-[4-[4,6-bis(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(C=2N=C(C=C(N=2)N2CC3CCC(O3)C2)N2CC3CCC(O3)C2)C=CC=1NC(=O)NC1=CC=NC=C1 HQDFRJIZSFCGMB-UHFFFAOYSA-N 0.000 claims description 3
• JATGKUYTHCYEKX-UHFFFAOYSA-N 1-[4-[4-(2-methylsulfonylethylamino)-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]-3-pyridin-3-ylurea Chemical compound N=1C(NCCS(=O)(=O)C)=CC(N2C3CCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CN=C1 JATGKUYTHCYEKX-UHFFFAOYSA-N 0.000 claims description 3
• RFKWUMCYKPJMAT-UHFFFAOYSA-N 1-[4-[4-(2-methylsulfonylethylamino)-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound N=1C(NCCS(=O)(=O)C)=CC(N2C3CCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 RFKWUMCYKPJMAT-UHFFFAOYSA-N 0.000 claims description 3
• FYCHZKJFIJTSTH-UHFFFAOYSA-N 1-[4-[4-(3,7-dioxa-9-azabicyclo[3.3.1]nonan-9-yl)-6-(propan-2-ylamino)pyrimidin-2-yl]phenyl]-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound N=1C(NC(C)C)=CC(N2C3COCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCN(C)CC1 FYCHZKJFIJTSTH-UHFFFAOYSA-N 0.000 claims description 3
• WYOGWLUFUUMDGX-UHFFFAOYSA-N 1-[4-[4-(3,7-dioxa-9-azabicyclo[3.3.1]nonan-9-yl)-6-(propan-2-ylamino)pyrimidin-2-yl]phenyl]-3-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]urea Chemical compound N=1C(NC(C)C)=CC(N2C3COCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1CN1CCN(C)CC1 WYOGWLUFUUMDGX-UHFFFAOYSA-N 0.000 claims description 3
• KTJRELYXAMVFFF-UHFFFAOYSA-N 1-[4-[4-(3,7-dioxa-9-azabicyclo[3.3.1]nonan-9-yl)-6-(propan-2-ylamino)pyrimidin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound N=1C(NC(C)C)=CC(N2C3COCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 KTJRELYXAMVFFF-UHFFFAOYSA-N 0.000 claims description 3
• CTMOHOOMAOPZFC-UHFFFAOYSA-N 1-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(oxan-4-yl)pyrimidin-2-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C=1C=CN=CC=1NC(=O)NC(C=C1)=CC=C1C(N=C(C=1)N2C3CCC2COC3)=NC=1C1CCOCC1 CTMOHOOMAOPZFC-UHFFFAOYSA-N 0.000 claims description 3
• IUMDAFMTUJRNDG-UHFFFAOYSA-N 1-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(oxan-4-yl)pyrimidin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(C=2N=C(C=C(N=2)C2CCOCC2)N2C3CCC2COC3)C=CC=1NC(=O)NC1=CC=NC=C1 IUMDAFMTUJRNDG-UHFFFAOYSA-N 0.000 claims description 3
• CKKYCLAHEURGMR-UHFFFAOYSA-N 1-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(oxan-4-ylamino)pyrimidin-2-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C=1C=CN=CC=1NC(=O)NC(C=C1)=CC=C1C(N=C(C=1)N2C3CCC2COC3)=NC=1NC1CCOCC1 CKKYCLAHEURGMR-UHFFFAOYSA-N 0.000 claims description 3
• KKUIWWXQXSCKIE-UHFFFAOYSA-N 1-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(oxan-4-ylamino)pyrimidin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(C=2N=C(C=C(NC3CCOCC3)N=2)N2C3CCC2COC3)C=CC=1NC(=O)NC1=CC=NC=C1 KKUIWWXQXSCKIE-UHFFFAOYSA-N 0.000 claims description 3
• AZPXEZSTQVYLPW-UHFFFAOYSA-N 1-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(propan-2-ylamino)pyrimidin-2-yl]phenyl]-3-[4-(2-pyrrolidin-1-ylethoxy)phenyl]urea Chemical compound N=1C(NC(C)C)=CC(N2C3CCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1OCCN1CCCC1 AZPXEZSTQVYLPW-UHFFFAOYSA-N 0.000 claims description 3
• MMFSHPJCJSLAGA-UHFFFAOYSA-N 1-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(propan-2-ylamino)pyrimidin-2-yl]phenyl]-3-[4-(pyrrolidin-1-ylmethyl)phenyl]urea Chemical compound N=1C(NC(C)C)=CC(N2C3CCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1CN1CCCC1 MMFSHPJCJSLAGA-UHFFFAOYSA-N 0.000 claims description 3
• FIYKFOSAPYOUPP-UHFFFAOYSA-N 1-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(propan-2-ylamino)pyrimidin-2-yl]phenyl]-3-pyridin-3-ylurea Chemical compound N=1C(NC(C)C)=CC(N2C3CCC2COC3)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CN=C1 FIYKFOSAPYOUPP-UHFFFAOYSA-N 0.000 claims description 3
• LMFFBOHRMSHFAG-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(propan-2-ylamino)pyrimidin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound N=1C(NC(C)C)=CC(N2CC3CCC(O3)C2)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 LMFFBOHRMSHFAG-UHFFFAOYSA-N 0.000 claims description 3
• LYXFOYSJZFENMZ-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(trifluoromethyl)pyrimidin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound N=1C(C(F)(F)F)=CC(N2CC3CCC(O3)C2)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 LYXFOYSJZFENMZ-UHFFFAOYSA-N 0.000 claims description 3
• ODSXTXHSNNDKHK-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-[4-(pyridin-3-ylcarbamoylamino)phenyl]pyrimidin-2-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C=1C=CN=CC=1NC(=O)NC(C=C1)=CC=C1C(N=1)=CC(N2CC3CCC(O3)C2)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CN=C1 ODSXTXHSNNDKHK-UHFFFAOYSA-N 0.000 claims description 3
• IZYBMHYEVVAFJL-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-[4-(pyridin-4-ylcarbamoylamino)phenyl]pyrimidin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(C=2N=C(N=C(C=2)N2CC3CCC(O3)C2)C=2C=CC(NC(=O)NC=3C=CN=CC=3)=CC=2)C=CC=1NC(=O)NC1=CC=NC=C1 IZYBMHYEVVAFJL-UHFFFAOYSA-N 0.000 claims description 3
• IOCRILFVUZQTFT-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-phenylpyrimidin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(C=2N=C(C=C(N=2)N2CC3CCC(O3)C2)C=2C=CC=CC=2)C=CC=1NC(=O)NC1=CC=NC=C1 IOCRILFVUZQTFT-UHFFFAOYSA-N 0.000 claims description 3
• DCMOOUOXJYZOIK-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-propan-2-yloxypyrimidin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound N=1C(OC(C)C)=CC(N2CC3CCC(O3)C2)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 DCMOOUOXJYZOIK-UHFFFAOYSA-N 0.000 claims description 3
• LWBBUIRPDMIQQK-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(C=2N=C(C=CN=2)N2CC3CCC(O3)C2)C=CC=1NC(=O)NC1=CC=NC=C1 LWBBUIRPDMIQQK-UHFFFAOYSA-N 0.000 claims description 3
• UKBPWWKTASOSAR-UHFFFAOYSA-N 1-[4-[4-(methylsulfonylmethyl)-6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl]phenyl]-3-(4-piperazin-1-ylphenyl)urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CC3CCC(O3)C2)=NC=1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCNCC1 UKBPWWKTASOSAR-UHFFFAOYSA-N 0.000 claims description 3
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