JP2013509438A5 - - Google Patents
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- Publication number
- JP2013509438A5 JP2013509438A5 JP2012537147A JP2012537147A JP2013509438A5 JP 2013509438 A5 JP2013509438 A5 JP 2013509438A5 JP 2012537147 A JP2012537147 A JP 2012537147A JP 2012537147 A JP2012537147 A JP 2012537147A JP 2013509438 A5 JP2013509438 A5 JP 2013509438A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrido
- pyrimidin
- phenylamino
- trifluoromethyl
- alkyl
- 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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- 125000003118 aryl group Chemical group 0.000 claims 99
- -1 C 3 -C 6 cycloalkyl sulfone Chemical class 0.000 claims 62
- 125000001072 heteroaryl group Chemical group 0.000 claims 38
- 125000000217 alkyl group Chemical group 0.000 claims 37
- 229920006395 saturated elastomer Polymers 0.000 claims 32
- 125000002619 bicyclic group Chemical group 0.000 claims 30
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 29
- 125000005842 heteroatom Chemical group 0.000 claims 28
- 229910052757 nitrogen Inorganic materials 0.000 claims 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 25
- 125000002950 monocyclic group Chemical group 0.000 claims 25
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 24
- 125000001188 haloalkyl group Chemical group 0.000 claims 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 19
- 229910052760 oxygen Inorganic materials 0.000 claims 19
- 239000001301 oxygen Substances 0.000 claims 19
- 150000003457 sulfones Chemical class 0.000 claims 19
- 150000003462 sulfoxides Chemical class 0.000 claims 19
- 229910052717 sulfur Inorganic materials 0.000 claims 19
- 239000011593 sulfur Substances 0.000 claims 19
- 125000005843 halogen group Chemical group 0.000 claims 17
- 125000000304 alkynyl group Chemical group 0.000 claims 16
- 229910052799 carbon Inorganic materials 0.000 claims 16
- 125000004432 carbon atom Chemical group C* 0.000 claims 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 11
- CSBPQHGADOHBPJ-UHFFFAOYSA-N 6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=NC=C2C(=O)NC=CC2=N1 CSBPQHGADOHBPJ-UHFFFAOYSA-N 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 9
- 102000007399 Nuclear hormone receptor Human genes 0.000 claims 8
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 150000003857 carboxamides Chemical class 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims 3
- QUCQUTXMTKXZTF-UHFFFAOYSA-N 8-bromo-2-(4-hydroxypiperidin-1-yl)-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(O)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=C(Br)C2=N1 QUCQUTXMTKXZTF-UHFFFAOYSA-N 0.000 claims 3
- NHWORLVFFPWOCG-UHFFFAOYSA-N 8-bromo-2-[4-hydroxy-4-(hydroxymethyl)piperidin-1-yl]-4-[4-methoxy-3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1NC1=NC(N2CCC(O)(CO)CC2)=NC2=C1C(=O)NC=C2Br NHWORLVFFPWOCG-UHFFFAOYSA-N 0.000 claims 3
- ULQQRNIWQOCYCI-UHFFFAOYSA-N 8-chloro-2-(4-hydroxypiperidin-1-yl)-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(O)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=C(Cl)C2=N1 ULQQRNIWQOCYCI-UHFFFAOYSA-N 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229940124530 sulfonamide Drugs 0.000 claims 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 3
- KLLWQQZIWABLMM-UHFFFAOYSA-N 2-(4-aminopiperidin-1-yl)-4-(3-bromoanilino)-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1CC(N)CCN1C1=NC(NC=2C=C(Br)C=CC=2)=C2C(=O)NC=CC2=N1 KLLWQQZIWABLMM-UHFFFAOYSA-N 0.000 claims 2
- GEOYUPAKWBFMCY-UHFFFAOYSA-N 2-(4-aminopiperidin-1-yl)-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1CC(N)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 GEOYUPAKWBFMCY-UHFFFAOYSA-N 0.000 claims 2
- SLIWCDKAMPYVHD-UHFFFAOYSA-N 2-(4-aminopiperidin-1-yl)-8-bromo-4-(4-phenoxyanilino)-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1CC(N)CCN1C1=NC(NC=2C=CC(OC=3C=CC=CC=3)=CC=2)=C2C(=O)NC=C(Br)C2=N1 SLIWCDKAMPYVHD-UHFFFAOYSA-N 0.000 claims 2
- OQWFKMRCKRKWJM-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)-4-(4-methylsulfonylanilino)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=NC(N2CCC(O)CC2)=NC2=C1C(=O)NC=C2 OQWFKMRCKRKWJM-UHFFFAOYSA-N 0.000 claims 2
- PFXJJNWJPALFKW-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)-4-[3-methoxy-5-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound FC(F)(F)C1=CC(OC)=CC(NC=2C=3C(=O)NC=CC=3N=C(N=2)N2CCC(O)CC2)=C1 PFXJJNWJPALFKW-UHFFFAOYSA-N 0.000 claims 2
- VPNJGTRMGOLFFE-HNCPQSOCSA-N 2-[(3r)-3-aminopyrrolidin-1-yl]-8-bromo-4-(4-bromo-3-methylanilino)-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1=C(Br)C(C)=CC(NC=2C=3C(=O)NC=C(Br)C=3N=C(N=2)N2C[C@H](N)CC2)=C1 VPNJGTRMGOLFFE-HNCPQSOCSA-N 0.000 claims 2
- JWDVLBRIYMKSPE-HNCPQSOCSA-N 2-[(3r)-3-aminopyrrolidin-1-yl]-8-bromo-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1[C@H](N)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=C(Br)C2=N1 JWDVLBRIYMKSPE-HNCPQSOCSA-N 0.000 claims 2
- YCQGWGUPQKSACP-PFEQFJNWSA-N 2-[(3r)-3-aminopyrrolidin-1-yl]-8-iodo-4-(4-phenoxyanilino)-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1[C@H](N)CCN1C1=NC(NC=2C=CC(OC=3C=CC=CC=3)=CC=2)=C2C(=O)NC=C(I)C2=N1 YCQGWGUPQKSACP-PFEQFJNWSA-N 0.000 claims 2
- MJZVMIRHKRTFQH-UHFFFAOYSA-N 2-[4-(hydroxymethyl)piperidin-1-yl]-4-[3-methoxy-5-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound FC(F)(F)C1=CC(OC)=CC(NC=2C=3C(=O)NC=CC=3N=C(N=2)N2CCC(CO)CC2)=C1 MJZVMIRHKRTFQH-UHFFFAOYSA-N 0.000 claims 2
- DPDHFMGZOGORQX-UHFFFAOYSA-N 4-(3,4-dimethoxyanilino)-2-[4-hydroxy-4-(hydroxymethyl)piperidin-1-yl]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(N2CCC(O)(CO)CC2)=NC2=C1C(=O)NC=C2 DPDHFMGZOGORQX-UHFFFAOYSA-N 0.000 claims 2
- VMPADCYUHYLGQG-UHFFFAOYSA-N 4-(3-bromo-4-methoxyanilino)-2-[4-hydroxy-4-(hydroxymethyl)piperidin-1-yl]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C(Br)C(OC)=CC=C1NC1=NC(N2CCC(O)(CO)CC2)=NC2=C1C(=O)NC=C2 VMPADCYUHYLGQG-UHFFFAOYSA-N 0.000 claims 2
- JTDGZXKALXMEHQ-UHFFFAOYSA-N 4-(3-bromoanilino)-2-[4-(dimethylamino)piperidin-1-yl]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C1=NC(NC=2C=C(Br)C=CC=2)=C2C(=O)NC=CC2=N1 JTDGZXKALXMEHQ-UHFFFAOYSA-N 0.000 claims 2
- MVJILHISNCDSDL-ZDUSSCGKSA-N 4-(3-bromoanilino)-2-[4-[[(2s)-1-hydroxypropan-2-yl]amino]piperidin-1-yl]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N[C@H](CO)C)CCN1C1=NC(NC=2C=C(Br)C=CC=2)=C2C(=O)NC=CC2=N1 MVJILHISNCDSDL-ZDUSSCGKSA-N 0.000 claims 2
- UWRGLAQTMHMTGR-UHFFFAOYSA-N 4-[4-(4-acetylpiperazin-1-yl)anilino]-2-[4-(hydroxymethyl)piperidin-1-yl]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CO)CC2)=NC2=C1C(=O)NC=C2 UWRGLAQTMHMTGR-UHFFFAOYSA-N 0.000 claims 2
- JZJZFCAXXMAKKI-UHFFFAOYSA-N 4-[4-chloro-3-(trifluoromethyl)anilino]-2-(4-hydroxypiperidin-1-yl)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(O)CCN1C1=NC(NC=2C=C(C(Cl)=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 JZJZFCAXXMAKKI-UHFFFAOYSA-N 0.000 claims 2
- CPRZMZBPXDPGNC-UHFFFAOYSA-N 4-[4-chloro-3-(trifluoromethyl)anilino]-2-[4-(hydroxymethyl)piperidin-1-yl]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(CO)CCN1C1=NC(NC=2C=C(C(Cl)=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 CPRZMZBPXDPGNC-UHFFFAOYSA-N 0.000 claims 2
- KSKZKZVQBVMQEK-UHFFFAOYSA-N 4-[4-chloro-3-(trifluoromethyl)anilino]-2-[4-hydroxy-4-(hydroxymethyl)piperidin-1-yl]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(CO)(O)CCN1C1=NC(NC=2C=C(C(Cl)=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 KSKZKZVQBVMQEK-UHFFFAOYSA-N 0.000 claims 2
- JODQUOPUBNKSHE-UHFFFAOYSA-N 8-bromo-2-[4-hydroxy-4-(hydroxymethyl)piperidin-1-yl]-4-(4-phenoxyanilino)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(CO)(O)CCN1C1=NC(NC=2C=CC(OC=3C=CC=CC=3)=CC=2)=C2C(=O)NC=C(Br)C2=N1 JODQUOPUBNKSHE-UHFFFAOYSA-N 0.000 claims 2
- NTSZYEUKFCFCMB-UHFFFAOYSA-N 8-bromo-2-[4-hydroxy-4-(hydroxymethyl)piperidin-1-yl]-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(CO)(O)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=C(Br)C2=N1 NTSZYEUKFCFCMB-UHFFFAOYSA-N 0.000 claims 2
- UHEYBRWETBMFMG-UHFFFAOYSA-N FC(C=1C=C(C=CC=1)NC=1N=CC2=C(N=1)C=CNC2=O)(F)F Chemical compound FC(C=1C=C(C=CC=1)NC=1N=CC2=C(N=1)C=CNC2=O)(F)F UHEYBRWETBMFMG-UHFFFAOYSA-N 0.000 claims 2
- 108010020246 Leucine-Rich Repeat Serine-Threonine Protein Kinase-2 Proteins 0.000 claims 2
- 102100032693 Leucine-rich repeat serine/threonine-protein kinase 2 Human genes 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 1
- UWJHLWFLONMNRA-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[4-[6-methyl-2-(methylamino)-5-oxopyrido[4,3-d]pyrimidin-4-yl]phenyl]urea Chemical compound C1=CN(C)C(=O)C=2C1=NC(NC)=NC=2C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C=C1 UWJHLWFLONMNRA-UHFFFAOYSA-N 0.000 claims 1
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 1
- KYAOIGFSSJYTAV-UHFFFAOYSA-N 2-(1,3-thiazolidin-3-yl)-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CSCC2)=NC2=C1C(=O)NC=C2 KYAOIGFSSJYTAV-UHFFFAOYSA-N 0.000 claims 1
- FWILRSIFEDCGFF-UHFFFAOYSA-N 2-(1,4-diazepan-1-yl)-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CCNCCC2)=NC2=C1C(=O)NC=C2 FWILRSIFEDCGFF-UHFFFAOYSA-N 0.000 claims 1
- QTGNPLDYSBDSBP-UHFFFAOYSA-N 2-(2-morpholin-4-ylethoxy)-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound FC(F)(F)C1=CC=CC(NC=2C=3C(=O)NC=CC=3N=C(OCCN3CCOCC3)N=2)=C1 QTGNPLDYSBDSBP-UHFFFAOYSA-N 0.000 claims 1
- ZIFLUDXWFHTTET-UHFFFAOYSA-N 2-(2-morpholin-4-ylethylamino)-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound FC(F)(F)C1=CC=CC(NC=2C=3C(=O)NC=CC=3N=C(NCCN3CCOCC3)N=2)=C1 ZIFLUDXWFHTTET-UHFFFAOYSA-N 0.000 claims 1
- RYGGCIBGKFDTSD-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-yl)-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound FC(F)(F)C1=CC=CC(NC=2C=3C(=O)NC=CC=3N=C(N=2)N2CC3=CC=CC=C3CC2)=C1 RYGGCIBGKFDTSD-UHFFFAOYSA-N 0.000 claims 1
- FPMHBUIAXFBVCH-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-yl)-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CC3=CC=CC=C3CC2)=NC2=C1C(=O)NC=C2 FPMHBUIAXFBVCH-UHFFFAOYSA-N 0.000 claims 1
- HKRSXWHJGCIZMY-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C(=O)C)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 HKRSXWHJGCIZMY-UHFFFAOYSA-N 0.000 claims 1
- VHLBUISSYVNERJ-UHFFFAOYSA-N 2-(4-aminopiperidin-1-yl)-4-(3,5-dimethoxyanilino)-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.COC1=CC(OC)=CC(NC=2C=3C(=O)NC=CC=3N=C(N=2)N2CCC(N)CC2)=C1 VHLBUISSYVNERJ-UHFFFAOYSA-N 0.000 claims 1
- CTTDFQUPWARXKU-UHFFFAOYSA-N 2-(4-aminopiperidin-1-yl)-4-(3-methylanilino)-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.CC1=CC=CC(NC=2C=3C(=O)NC=CC=3N=C(N=2)N2CCC(N)CC2)=C1 CTTDFQUPWARXKU-UHFFFAOYSA-N 0.000 claims 1
- IDTFWKPHMCIKHZ-UHFFFAOYSA-N 2-(4-aminopiperidin-1-yl)-4-(4-bromoanilino)-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1CC(N)CCN1C1=NC(NC=2C=CC(Br)=CC=2)=C2C(=O)NC=CC2=N1 IDTFWKPHMCIKHZ-UHFFFAOYSA-N 0.000 claims 1
- XODWAOQPSCMAOU-UHFFFAOYSA-N 2-(4-aminopiperidin-1-yl)-4-[3,5-bis(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1CC(N)CCN1C1=NC(NC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C2C(=O)NC=CC2=N1 XODWAOQPSCMAOU-UHFFFAOYSA-N 0.000 claims 1
- WNJNFLHBUDVBNS-UHFFFAOYSA-N 2-(4-aminopiperidin-1-yl)-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1CC(N)CCN1C1=NC(NC=2C=CC(=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 WNJNFLHBUDVBNS-UHFFFAOYSA-N 0.000 claims 1
- CDJAGGGPGBCHHI-UHFFFAOYSA-N 2-(4-ethylpiperazin-1-yl)-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(CC)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 CDJAGGGPGBCHHI-UHFFFAOYSA-N 0.000 claims 1
- UVOUXMCXXRXJSF-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)-4-(3-methylanilino)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NC=CC=3N=C(N=2)N2CCC(O)CC2)=C1 UVOUXMCXXRXJSF-UHFFFAOYSA-N 0.000 claims 1
- KWTXYVYFLMWPFD-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)-4-(3-methylsulfonylanilino)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound CS(=O)(=O)C1=CC=CC(NC=2C=3C(=O)NC=CC=3N=C(N=2)N2CCC(O)CC2)=C1 KWTXYVYFLMWPFD-UHFFFAOYSA-N 0.000 claims 1
- JELXZLATVQEDBD-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)-4-(3h-indol-2-ylamino)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(O)CCN1C1=NC(NC=2CC3=CC=CC=C3N=2)=C2C(=O)NC=CC2=N1 JELXZLATVQEDBD-UHFFFAOYSA-N 0.000 claims 1
- KHJMBIAHNUWJPW-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)-4-(4-morpholin-4-ylanilino)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(O)CCN1C1=NC(NC=2C=CC(=CC=2)N2CCOCC2)=C2C(=O)NC=CC2=N1 KHJMBIAHNUWJPW-UHFFFAOYSA-N 0.000 claims 1
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- KESYUFNFYLJZHN-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(O)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 KESYUFNFYLJZHN-UHFFFAOYSA-N 0.000 claims 1
- KQMDVPOCKULZAI-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(O)CCN1C1=NC(NC=2C=CC(=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 KQMDVPOCKULZAI-UHFFFAOYSA-N 0.000 claims 1
- JTLACETWTOHYDD-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)-4-[4-morpholin-4-yl-3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(O)CCN1C1=NC(NC=2C=C(C(N3CCOCC3)=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 JTLACETWTOHYDD-UHFFFAOYSA-N 0.000 claims 1
- PGJSLHCHYBJFLW-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)-6-methyl-4-[3-(trifluoromethyl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=12C(=O)N(C)C=CC2=NC(N2CCC(O)CC2)=NC=1NC1=CC=CC(C(F)(F)F)=C1 PGJSLHCHYBJFLW-UHFFFAOYSA-N 0.000 claims 1
- IDARVBHTOBSLNW-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)-8-iodo-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(O)CCN1C1=NC(NC=2C=CC(=CC=2)C(F)(F)F)=C2C(=O)NC=C(I)C2=N1 IDARVBHTOBSLNW-UHFFFAOYSA-N 0.000 claims 1
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- POBOUSOKEDDROE-UHFFFAOYSA-N 2-(4-methylsulfonylpiperazin-1-yl)-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(S(=O)(=O)C)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 POBOUSOKEDDROE-UHFFFAOYSA-N 0.000 claims 1
- SLIFFGBDMBSXJS-UHFFFAOYSA-N 2-(4-morpholin-4-ylpiperidin-1-yl)-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound FC(F)(F)C1=CC=CC(NC=2C=3C(=O)NC=CC=3N=C(N=2)N2CCC(CC2)N2CCOCC2)=C1 SLIFFGBDMBSXJS-UHFFFAOYSA-N 0.000 claims 1
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- YUBHQYQTDBUAQD-UHFFFAOYSA-N 2-(benzylamino)-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(NCC=2C=CC=CC=2)=NC2=C1C(=O)NC=C2 YUBHQYQTDBUAQD-UHFFFAOYSA-N 0.000 claims 1
- LRAWZXZQTIFBBO-UHFFFAOYSA-N 2-(cyclohexylamino)-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(NC2CCCCC2)=NC2=C1C(=O)NC=C2 LRAWZXZQTIFBBO-UHFFFAOYSA-N 0.000 claims 1
- NFXNFOBESPZLIF-UHFFFAOYSA-N 2-(cyclopentylamino)-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(NC2CCCC2)=NC2=C1C(=O)NC=C2 NFXNFOBESPZLIF-UHFFFAOYSA-N 0.000 claims 1
- GBNJUKNPMXFOIP-UHFFFAOYSA-N 2-(morpholin-4-ylamino)-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound FC(F)(F)C1=CC=CC(NC=2C=3C(=O)NC=CC=3N=C(NN3CCOCC3)N=2)=C1 GBNJUKNPMXFOIP-UHFFFAOYSA-N 0.000 claims 1
- GZQRNZHWNGBFTE-UHFFFAOYSA-N 2-(oxan-4-ylamino)-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(NC2CCOCC2)=NC2=C1C(=O)NC=C2 GZQRNZHWNGBFTE-UHFFFAOYSA-N 0.000 claims 1
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- POTLEFZPCQTIFZ-UHFFFAOYSA-N 2-(piperidin-4-ylmethylamino)-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1=CC(C(F)(F)F)=CC=C1NC1=NC(NCC2CCNCC2)=NC2=C1C(=O)NC=C2 POTLEFZPCQTIFZ-UHFFFAOYSA-N 0.000 claims 1
- GYRRMTWUWWPQHL-UHFFFAOYSA-N 2-[(1-methylpiperidin-4-yl)methylamino]-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCC1CNC1=NC(NC=2C=CC(=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 GYRRMTWUWWPQHL-UHFFFAOYSA-N 0.000 claims 1
- BTCUWBIMQWZONX-UHFFFAOYSA-N 2-[(1-propan-2-ylpiperidin-4-yl)methylamino]-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C(C)C)CCC1CNC1=NC(NC=2C=CC(=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 BTCUWBIMQWZONX-UHFFFAOYSA-N 0.000 claims 1
- JXABSHYWZNDLJL-UHFFFAOYSA-N 2-[(2-aminophenyl)methylamino]-4-(4-morpholin-4-ylanilino)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound NC1=CC=CC=C1CNC1=NC(NC=2C=CC(=CC=2)N2CCOCC2)=C2C(=O)NC=CC2=N1 JXABSHYWZNDLJL-UHFFFAOYSA-N 0.000 claims 1
- UTJNZILSYJOSJM-UHFFFAOYSA-N 2-[(2-aminophenyl)methylamino]-4-[3,5-bis(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound NC1=CC=CC=C1CNC1=NC(NC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C2C(=O)NC=CC2=N1 UTJNZILSYJOSJM-UHFFFAOYSA-N 0.000 claims 1
- CAYBJNSSLBJENW-UHFFFAOYSA-N 2-[(3-aminocyclohexyl)amino]-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1C(N)CCCC1NC1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 CAYBJNSSLBJENW-UHFFFAOYSA-N 0.000 claims 1
- ASXFHCYHOZVKPF-RFVHGSKJSA-N 2-[(3r)-3-aminopyrrolidin-1-yl]-4-(4-bromoanilino)-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1[C@H](N)CCN1C1=NC(NC=2C=CC(Br)=CC=2)=C2C(=O)NC=CC2=N1 ASXFHCYHOZVKPF-RFVHGSKJSA-N 0.000 claims 1
- MSLUVFDCXLKRLI-RFVHGSKJSA-N 2-[(3r)-3-aminopyrrolidin-1-yl]-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1[C@H](N)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 MSLUVFDCXLKRLI-RFVHGSKJSA-N 0.000 claims 1
- SBCIJEYGQIUIFH-PFEQFJNWSA-N 2-[(3r)-3-aminopyrrolidin-1-yl]-8-bromo-4-(4-phenoxyanilino)-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1[C@H](N)CCN1C1=NC(NC=2C=CC(OC=3C=CC=CC=3)=CC=2)=C2C(=O)NC=C(Br)C2=N1 SBCIJEYGQIUIFH-PFEQFJNWSA-N 0.000 claims 1
- NFEMRONPIKCMSD-GFCCVEGCSA-N 2-[(3r)-3-hydroxypyrrolidin-1-yl]-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1[C@H](O)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 NFEMRONPIKCMSD-GFCCVEGCSA-N 0.000 claims 1
- ASXFHCYHOZVKPF-MERQFXBCSA-N 2-[(3s)-3-aminopyrrolidin-1-yl]-4-(4-bromoanilino)-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C1=NC(NC=2C=CC(Br)=CC=2)=C2C(=O)NC=CC2=N1 ASXFHCYHOZVKPF-MERQFXBCSA-N 0.000 claims 1
- DJANDTGEFFLMIW-NSHDSACASA-N 2-[(3s)-3-aminopyrrolidin-1-yl]-4-(4-methylsulfonylanilino)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=NC(N2C[C@@H](N)CC2)=NC2=C1C(=O)NC=C2 DJANDTGEFFLMIW-NSHDSACASA-N 0.000 claims 1
- MSLUVFDCXLKRLI-MERQFXBCSA-N 2-[(3s)-3-aminopyrrolidin-1-yl]-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 MSLUVFDCXLKRLI-MERQFXBCSA-N 0.000 claims 1
- NFEMRONPIKCMSD-LBPRGKRZSA-N 2-[(3s)-3-hydroxypyrrolidin-1-yl]-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1[C@@H](O)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 NFEMRONPIKCMSD-LBPRGKRZSA-N 0.000 claims 1
- OBZRMOWKWQWKIC-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylamino]-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(F)=CC=C1CNC1=NC(NC=2C=CC(=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 OBZRMOWKWQWKIC-UHFFFAOYSA-N 0.000 claims 1
- UOOIBWYRUJLYBE-UHFFFAOYSA-N 2-[(4-methyl-1,3-thiazol-2-yl)amino]-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=CSC(NC=2N=C3C(C(NC=C3)=O)=C(NC=3C=CC(=CC=3)C(F)(F)F)N=2)=N1 UOOIBWYRUJLYBE-UHFFFAOYSA-N 0.000 claims 1
- OTMJEVVBJMCAOM-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(CCO)CCN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 OTMJEVVBJMCAOM-UHFFFAOYSA-N 0.000 claims 1
- NKFZAYZMKQBTRQ-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(CCO)CCN1C1=NC(NC=2C=CC(=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 NKFZAYZMKQBTRQ-UHFFFAOYSA-N 0.000 claims 1
- MILYKUXQFBBWIK-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1C(N=C1C=2C(NC=C1)=O)=NC=2NC1=CC=CC(C(F)(F)F)=C1 MILYKUXQFBBWIK-UHFFFAOYSA-N 0.000 claims 1
- DTASLHOBQHVENX-UHFFFAOYSA-N 2-[4-(hydroxymethyl)piperidin-1-yl]-4-(4-methoxyphenyl)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(OC)=CC=C1C1=NC(N2CCC(CO)CC2)=NC2=C1C(=O)NC=C2 DTASLHOBQHVENX-UHFFFAOYSA-N 0.000 claims 1
- QKGWFBXDEBODGG-UHFFFAOYSA-N 2-[4-(hydroxymethyl)piperidin-1-yl]-4-(4-morpholin-4-ylanilino)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(CO)CCN1C1=NC(NC=2C=CC(=CC=2)N2CCOCC2)=C2C(=O)NC=CC2=N1 QKGWFBXDEBODGG-UHFFFAOYSA-N 0.000 claims 1
- CKCDTBZLELPNDH-UHFFFAOYSA-N 2-[4-(hydroxymethyl)piperidin-1-yl]-4-[(4-sulfonylcyclohexa-1,5-dien-1-yl)amino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(CO)CCN1C1=NC(NC=2C=CC(CC=2)=S(=O)=O)=C2C(=O)NC=CC2=N1 CKCDTBZLELPNDH-UHFFFAOYSA-N 0.000 claims 1
- WEADIXMHILCWBB-UHFFFAOYSA-N 2-[4-(hydroxymethyl)piperidin-1-yl]-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(CO)CCN1C1=NC(NC=2C=CC(=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 WEADIXMHILCWBB-UHFFFAOYSA-N 0.000 claims 1
- HJALJFXWLMCXST-XFULWGLBSA-N 2-[4-[(3r)-3-aminopyrrolidin-1-yl]piperidin-1-yl]-4-(3-bromoanilino)-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1[C@H](N)CCN1C1CCN(C=2N=C3C(C(NC=C3)=O)=C(NC=3C=C(Br)C=CC=3)N=2)CC1 HJALJFXWLMCXST-XFULWGLBSA-N 0.000 claims 1
- XYAAXXARNQURJH-UHFFFAOYSA-N 2-[4-[(dimethylamino)methyl]piperidin-1-yl]-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(CN(C)C)CCN1C1=NC(NC=2C=CC(=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 XYAAXXARNQURJH-UHFFFAOYSA-N 0.000 claims 1
- RXEITYPUKYENPJ-UHFFFAOYSA-N 2-[4-[4-(2-hydroxyethyl)piperazine-1-carbonyl]piperidin-1-yl]-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(CCO)CCN1C(=O)C1CCN(C=2N=C3C(C(NC=C3)=O)=C(NC=3C=CC(=CC=3)C(F)(F)F)N=2)CC1 RXEITYPUKYENPJ-UHFFFAOYSA-N 0.000 claims 1
- JDTWINODLBBVLB-UHFFFAOYSA-N 2-[4-hydroxy-4-(hydroxymethyl)piperidin-1-yl]-4-[3-methoxy-5-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound FC(F)(F)C1=CC(OC)=CC(NC=2C=3C(=O)NC=CC=3N=C(N=2)N2CCC(O)(CO)CC2)=C1 JDTWINODLBBVLB-UHFFFAOYSA-N 0.000 claims 1
- UJSQIHFORUUISG-NVXWUHKLSA-N 2-[[(1r,2r)-2-(dimethylamino)cyclohexyl]amino]-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound CN(C)[C@@H]1CCCC[C@H]1NC1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 UJSQIHFORUUISG-NVXWUHKLSA-N 0.000 claims 1
- IIWBHGOCHDWWKA-QZTJIDSGSA-N 2-[[(1r,2r)-2-aminocyclohexyl]amino]-4-(4-morpholin-4-ylanilino)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N[C@@H]1CCCC[C@H]1NC1=NC(NC=2C=CC(=CC=2)N2CCOCC2)=C2C(=O)NC=CC2=N1 IIWBHGOCHDWWKA-QZTJIDSGSA-N 0.000 claims 1
- VLGXRXNLZVPHLJ-TZMCWYRMSA-N 2-[[(1r,2r)-2-aminocyclohexyl]amino]-4-[2-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N[C@@H]1CCCC[C@H]1NC1=NC(NC=2C(=CC=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 VLGXRXNLZVPHLJ-TZMCWYRMSA-N 0.000 claims 1
- BXLDLSUMOAPBBW-ZIAGYGMSSA-N 2-[[(1r,2r)-2-aminocyclohexyl]amino]-4-[3,5-bis(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N[C@@H]1CCCC[C@H]1NC1=NC(NC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C2C(=O)NC=CC2=N1 BXLDLSUMOAPBBW-ZIAGYGMSSA-N 0.000 claims 1
- IIWBHGOCHDWWKA-ZWKOTPCHSA-N 2-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(4-morpholin-4-ylanilino)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(NC=2C=CC(=CC=2)N2CCOCC2)=C2C(=O)NC=CC2=N1 IIWBHGOCHDWWKA-ZWKOTPCHSA-N 0.000 claims 1
- VLGXRXNLZVPHLJ-GXTWGEPZSA-N 2-[[(1r,2s)-2-aminocyclohexyl]amino]-4-[2-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(NC=2C(=CC=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 VLGXRXNLZVPHLJ-GXTWGEPZSA-N 0.000 claims 1
- OSAVMYCIMXJRKW-UONOGXRCSA-N 2-[[(1r,2s)-2-aminocyclohexyl]amino]-4-[3-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 OSAVMYCIMXJRKW-UONOGXRCSA-N 0.000 claims 1
- JJPLYNYZFBRALQ-LBPRGKRZSA-N 2-[[(1s)-1-(4-fluorophenyl)ethyl]amino]-4-[4-(trifluoromethyl)anilino]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N([C@@H](C)C=1C=CC(F)=CC=1)C(N=C1C=2C(NC=C1)=O)=NC=2NC1=CC=C(C(F)(F)F)C=C1 JJPLYNYZFBRALQ-LBPRGKRZSA-N 0.000 claims 1
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- LXAGRYPEAXTXIR-UHFFFAOYSA-N 4-(4-chloro-3-methoxyanilino)-2-[4-hydroxy-4-(hydroxymethyl)piperidin-1-yl]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C(Cl)C(OC)=CC(NC=2C=3C(=O)NC=CC=3N=C(N=2)N2CCC(O)(CO)CC2)=C1 LXAGRYPEAXTXIR-UHFFFAOYSA-N 0.000 claims 1
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- PZPFFYMISMLKCX-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)anilino]-2-(4-hydroxypiperidin-1-yl)-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(O)CCN1C1=NC(NC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C2C(=O)NC=CC2=N1 PZPFFYMISMLKCX-UHFFFAOYSA-N 0.000 claims 1
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- QBHHOUDGSJQPJA-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)anilino]-2-[4-(hydroxymethyl)piperidin-1-yl]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(CO)CCN1C1=NC(NC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C2C(=O)NC=CC2=N1 QBHHOUDGSJQPJA-UHFFFAOYSA-N 0.000 claims 1
- KYWGBJQYXMEPSU-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)anilino]-2-[4-hydroxy-4-(hydroxymethyl)piperidin-1-yl]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(CO)(O)CCN1C1=NC(NC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C2C(=O)NC=CC2=N1 KYWGBJQYXMEPSU-UHFFFAOYSA-N 0.000 claims 1
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- YCLVXMJEBOAGBZ-MERQFXBCSA-N 4-[3,5-bis(trifluoromethyl)anilino]-2-[[(3s)-pyrrolidin-3-yl]amino]-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC(C(F)(F)F)=CC(NC=2C=3C(=O)NC=CC=3N=C(N[C@@H]3CNCC3)N=2)=C1 YCLVXMJEBOAGBZ-MERQFXBCSA-N 0.000 claims 1
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- PVHKXJCINQXTHN-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)anilino]-2-piperazin-1-yl-6h-pyrido[4,3-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC(C(F)(F)F)=CC(NC=2C=3C(=O)NC=CC=3N=C(N=2)N2CCNCC2)=C1 PVHKXJCINQXTHN-UHFFFAOYSA-N 0.000 claims 1
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- JMEGUODDPBGPFR-UHFFFAOYSA-N 4-[3-bromo-5-(trifluoromethyl)anilino]-2-[4-hydroxy-4-(hydroxymethyl)piperidin-1-yl]-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(CO)(O)CCN1C1=NC(NC=2C=C(C=C(Br)C=2)C(F)(F)F)=C2C(=O)NC=CC2=N1 JMEGUODDPBGPFR-UHFFFAOYSA-N 0.000 claims 1
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| WO2012097479A1 (en) * | 2011-01-21 | 2012-07-26 | Abbott Laboratories | Bicyclic inhibitors of anaphastic lymphoma kinase |
| CN103415516A (zh) * | 2011-01-21 | 2013-11-27 | Abbvie公司 | Alk的双环抑制剂 |
| PL2748166T3 (pl) * | 2011-08-23 | 2019-05-31 | Asana Biosciences Llc | Związki pirimido-pirydazynonowe oraz ich zastosowanie |
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| MX2014010176A (es) * | 2012-02-23 | 2014-11-10 | Abbvie Inc | Inhibidores de cinasas de piridopirimidinona. |
| US8877763B2 (en) * | 2012-03-22 | 2014-11-04 | Genosco | Substituted pyridopyrimidine compounds and their use as FLT3 inhibitors |
| EP2867236B1 (en) | 2012-06-29 | 2017-06-14 | Pfizer Inc | Novel 4-(substituted-amino)-7h-pyrrolo[2,3-d]pyrimidines as lrrk2 inhibitors |
| JP6374384B2 (ja) | 2012-08-07 | 2018-08-15 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | プロテインキナーゼ阻害剤としてのピリドピリミジン誘導体 |
| CN104520297B (zh) | 2012-08-13 | 2016-08-24 | 瑞士诺华动物保健有限公司 | 作为肾酪氨酸激酶抑制剂的双环杂芳基环烷基二胺衍生物 |
| CN103664938A (zh) * | 2012-09-12 | 2014-03-26 | 山东亨利医药科技有限责任公司 | 含有嘧啶并环的syk抑制剂 |
| WO2014045029A1 (en) * | 2012-09-18 | 2014-03-27 | Ziarco Pharma Ltd | 2-(2-aminocyclohexyl)amino-pyrimidine-5-carboxamides as spleen tyrosine kinasei(syk) inhibitors |
| EP2900639B1 (en) | 2012-09-27 | 2017-08-16 | Portola Pharmaceuticals, Inc. | Bicyclic dihydropyridone kinase inhibitors |
| ES2649156T3 (es) | 2013-01-14 | 2018-01-10 | Incyte Holdings Corporation | Compuestos bicíclicos de carboxamida aromática útiles como inhibidores de quinasas Pim |
| PE20191245A1 (es) | 2013-01-15 | 2019-09-18 | Incyte Holdings Corp | Compuestos de tiazolcarboxamidas y piridinacarboxamida utiles como inhibidores de quinasa pim |
| CN104341437A (zh) * | 2013-07-30 | 2015-02-11 | 山东亨利医药科技有限责任公司 | 含有双环基团的syk抑制剂 |
| EA201690458A1 (ru) | 2013-08-23 | 2016-07-29 | Инсайт Корпорейшн | Фуро- и тиенопиридинкарбоксамиды, используемые в качестве ингибиторов pim-киназы |
| EP3083618B1 (en) | 2013-12-17 | 2018-02-21 | Pfizer Inc | Novel 3,4-disubstituted-1h-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7h-pyrrolo[2,3-c]pyridazines as lrrk2 inhibitors |
| WO2015146928A1 (ja) * | 2014-03-24 | 2015-10-01 | 武田薬品工業株式会社 | 複素環化合物 |
| US10004751B2 (en) | 2014-07-10 | 2018-06-26 | The J. David Gladstone Institutes | Compositions and methods for treating Dengue virus infection |
| US9822124B2 (en) | 2014-07-14 | 2017-11-21 | Incyte Corporation | Bicyclic heteroaromatic carboxamide compounds useful as Pim kinase inhibitors |
| US9580418B2 (en) | 2014-07-14 | 2017-02-28 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as Pim kinase inhibitors |
| KR20160035411A (ko) * | 2014-09-23 | 2016-03-31 | 주식회사 오스코텍 | LRRK2 (Leucine Rich Repeat Kinase 2) 키나제 억제제로서의 피리도피리미딘 유도체 화합물 |
| WO2016196244A1 (en) | 2015-05-29 | 2016-12-08 | Incyte Corporation | Pyridineamine compounds useful as pim kinase inhibitors |
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