CA2864142A1 - Pyridopyrimidinone inhibitors of kinases - Google Patents

Info

Publication number

CA2864142A1

CA2864142A1 CA2864142A CA2864142A CA2864142A1 CA 2864142 A1 CA2864142 A1 CA 2864142A1 CA 2864142 A CA2864142 A CA 2864142A CA 2864142 A CA2864142 A CA 2864142A CA 2864142 A1 CA2864142 A1 CA 2864142A1

Authority

CA

Canada

Prior art keywords

pyrimidin

amino

alkyl

phenyl

pyrido

Prior art date

2012-02-23

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 108091000080 Phosphotransferase Proteins 0.000 title abstract description 16
• 102000020233 phosphotransferase Human genes 0.000 title abstract description 16
• 239000003112 inhibitor Substances 0.000 title description 36
• IAAQUOVTPAMQCR-UHFFFAOYSA-N 1h-pyrido[3,2-d]pyrimidin-2-one Chemical compound C1=CC=C2NC(=O)N=CC2=N1 IAAQUOVTPAMQCR-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 384
• 150000003839 salts Chemical class 0.000 claims abstract description 53
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 21
• 238000000034 method Methods 0.000 claims abstract description 17
• 201000011510 cancer Diseases 0.000 claims abstract description 11
• -1 C1-8 ̈alkyl Chemical group 0.000 claims description 292
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 133
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 116
• 125000003118 aryl group Chemical group 0.000 claims description 109
• 125000001072 heteroaryl group Chemical group 0.000 claims description 107
• 125000001424 substituent group Chemical group 0.000 claims description 107
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 96
• 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 description 74
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 70
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 62
• 229910052739 hydrogen Inorganic materials 0.000 claims description 59
• 239000001257 hydrogen Substances 0.000 claims description 59
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 41
• 125000001624 naphthyl group Chemical group 0.000 claims description 40
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 40
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 39
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 39
• 125000004043 oxo group Chemical group O=* 0.000 claims description 32
• 125000000623 heterocyclic group Chemical group 0.000 claims description 31
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 28
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 239000012453 solvate Substances 0.000 claims description 21
• 125000001188 haloalkyl group Chemical group 0.000 claims description 20
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 18
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 17
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 16
• 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 6
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 6
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• QXUSBOKZKRAPTI-UHFFFAOYSA-N 3h-1,8-naphthyridin-4-one Chemical compound C1=CC=C2C(=O)CC=NC2=N1 QXUSBOKZKRAPTI-UHFFFAOYSA-N 0.000 claims description 4
• SJKPWMYKSVBUNO-UHFFFAOYSA-N 8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)-6-(1,3,5-trimethylpyrazol-4-yl)pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=NN(C)C(C)=C1N1C(=O)C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=C1 SJKPWMYKSVBUNO-UHFFFAOYSA-N 0.000 claims description 4
• WJCAFRDKXHPCQI-UHFFFAOYSA-N ethyl 2-[2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxo-8-phenylpyrido[4,3-d]pyrimidin-6-yl]acetate Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C(=O)N(CC(=O)OCC)C=C1C1=CC=CC=C1 WJCAFRDKXHPCQI-UHFFFAOYSA-N 0.000 claims description 4
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
• SXIOYKBEPRVZKU-UHFFFAOYSA-N 2-[[2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxo-8-phenylpyrido[4,3-d]pyrimidin-6-yl]methyl]benzonitrile Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=3C(=CC=CC=3)C#N)C=C(C=3C=CC=CC=3)C2=N1 SXIOYKBEPRVZKU-UHFFFAOYSA-N 0.000 claims description 3
• KITLQPWNURWBMD-UHFFFAOYSA-N ethyl 2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxo-6h-pyrido[4,3-d]pyrimidine-8-carboxylate Chemical compound N1=C2C(C(=O)OCC)=CNC(=O)C2=CN=C1NC(C=C1)=CC=C1N1CCN(C)CC1 KITLQPWNURWBMD-UHFFFAOYSA-N 0.000 claims description 3
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• DOZVXATWWKJRRW-UHFFFAOYSA-N 2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-methyl-6-naphthalen-1-ylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C4=CC=CC=C4C=CC=3)C=C(C)C2=N1 DOZVXATWWKJRRW-UHFFFAOYSA-N 0.000 claims description 2
• DNYDUKJCKBCRRV-UHFFFAOYSA-N 6-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-[4-(4-methylpiperazin-1-yl)anilino]-8-phenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=3C(=CC=C(C=3)C(F)(F)F)F)C=C(C=3C=CC=CC=3)C2=N1 DNYDUKJCKBCRRV-UHFFFAOYSA-N 0.000 claims description 2
• MUASXNRDGTUSIE-UHFFFAOYSA-N 6-benzyl-n-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxopyrido[4,3-d]pyrimidine-8-carboxamide Chemical compound O=C1C2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C2C(C(=O)NC)=CN1CC1=CC=CC=C1 MUASXNRDGTUSIE-UHFFFAOYSA-N 0.000 claims description 2
• GULLRNQGFIFIKM-UHFFFAOYSA-N 6H-pyrimido[5,4-c][1,8]naphthyridin-5-one Chemical compound C1=NC=C2C(=O)NC3=NC=CC=C3C2=N1 GULLRNQGFIFIKM-UHFFFAOYSA-N 0.000 claims description 2
• FVDNKIKGGJCPTP-UHFFFAOYSA-N 8-bromo-6-(cyclopropylmethyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC3CC3)C=C(Br)C2=N1 FVDNKIKGGJCPTP-UHFFFAOYSA-N 0.000 claims description 2
• JQADBLZPOCMBPL-UHFFFAOYSA-N 8-methyl-2-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-6-quinolin-8-ylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1N(C)CC2=CC(NC=3N=C4C(C(N(C=5C6=NC=CC=C6C=CC=5)C=C4C)=O)=CN=3)=CC=C2C21CC2 JQADBLZPOCMBPL-UHFFFAOYSA-N 0.000 claims description 2
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 2
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 2
• 230000003247 decreasing effect Effects 0.000 claims description 2
• JSLSBFFNPXZYGG-UHFFFAOYSA-N methyl 4-chloro-3-[2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-methyl-5-oxopyrido[4,3-d]pyrimidin-6-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(N2C(C3=CN=C(NC=4C=CC(=CC=4)N4CCC(CC4)N(C)C)N=C3C(C)=C2)=O)=C1 JSLSBFFNPXZYGG-UHFFFAOYSA-N 0.000 claims description 2
• ZCLLSDJZZDLUMN-UHFFFAOYSA-N methyl 4-chloro-3-[8-methyl-5-oxo-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-6-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(N2C(C3=CN=C(NC=4C=C5CNCCC5=CC=4)N=C3C(C)=C2)=O)=C1 ZCLLSDJZZDLUMN-UHFFFAOYSA-N 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 32
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
• 102000007399 Nuclear hormone receptor Human genes 0.000 claims 7
• 108020005497 Nuclear hormone receptor Proteins 0.000 claims 7
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 4
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 3
• GRHZLQBPAJAHDM-SPRQWYLLSA-N [(3as,4r,6ar)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] n-[(2s,4s,5s)-5-[[2-(2,6-dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate Chemical compound CC1=CC=CC(C)=C1OCC(=O)N[C@H]([C@@H](O)C[C@H](CC=1C=CC=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)CC1=CC=CC=C1 GRHZLQBPAJAHDM-SPRQWYLLSA-N 0.000 claims 3
• AMDZGJIAKLYONC-UHFFFAOYSA-N 2-[4-[[6-(2,6-dichlorophenyl)-8-methyl-5-oxopyrido[4,3-d]pyrimidin-2-yl]amino]phenyl]sulfonyl-n-methylacetamide Chemical compound C1=CC(S(=O)(=O)CC(=O)NC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 AMDZGJIAKLYONC-UHFFFAOYSA-N 0.000 claims 2
• MIIKEUZRZIUNFL-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[(1,1-dimethyl-2,3-dihydroisoindol-5-yl)amino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4C(C(NC4)(C)C)=CC=3)N=C2C(C)=CN1C1=C(Cl)C=CC=C1Cl MIIKEUZRZIUNFL-UHFFFAOYSA-N 0.000 claims 2
• JXVVNMLOOWMJPU-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[4-(1-methylpiperidin-4-yl)oxyanilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCC1OC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 JXVVNMLOOWMJPU-UHFFFAOYSA-N 0.000 claims 2
• UPTKQADDXWWLFL-UHFFFAOYSA-N 6-(2-hydroxy-6-methylphenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=CC=CC(O)=C1N1C(=O)C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=C1 UPTKQADDXWWLFL-UHFFFAOYSA-N 0.000 claims 2
• ZWSVDXQZAUFCRA-UHFFFAOYSA-N 6-(2-hydroxyphenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=CN1C1=CC=CC=C1O ZWSVDXQZAUFCRA-UHFFFAOYSA-N 0.000 claims 2
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
• YXRWEBGBSHYCEB-UHFFFAOYSA-N 2-[4-(2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrol-5-yl)anilino]-6-(2,6-dichlorophenyl)-8-ethenylpyrido[4,3-d]pyrimidin-5-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC4CNCC4C3)N=C2C(C=C)=C1 YXRWEBGBSHYCEB-UHFFFAOYSA-N 0.000 claims 1
• WMAILZJXDPEVNY-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-6-phenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C=CC=CC=3)C=CC2=N1 WMAILZJXDPEVNY-UHFFFAOYSA-N 0.000 claims 1
• JMYMRWWPXDAHQC-UHFFFAOYSA-N 2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-6-(2,6-dimethylphenyl)-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3C)C)C=C(C)C2=N1 JMYMRWWPXDAHQC-UHFFFAOYSA-N 0.000 claims 1
• PXDTVJDUPULMJX-UHFFFAOYSA-N 2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-6-(2-fluoro-6-methylphenyl)-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3C)F)C=C(C)C2=N1 PXDTVJDUPULMJX-UHFFFAOYSA-N 0.000 claims 1
• PFHXDGVRFUKYMC-UHFFFAOYSA-N 2-[4-[4-[3-(dimethylamino)propyl]piperazin-1-yl]anilino]-6-(2,6-dimethylphenyl)-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(CCCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3C)C)C=C(C)C2=N1 PFHXDGVRFUKYMC-UHFFFAOYSA-N 0.000 claims 1
• BTSIRDYMWZOQJR-UHFFFAOYSA-N 2-[4-[[6-(2,6-dichlorophenyl)-8-methyl-5-oxopyrido[4,3-d]pyrimidin-2-yl]amino]phenyl]sulfanyl-n-methylacetamide Chemical compound C1=CC(SCC(=O)NC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 BTSIRDYMWZOQJR-UHFFFAOYSA-N 0.000 claims 1
• XIPFHAWJSGGGPQ-UHFFFAOYSA-N 2-amino-6-(2,6-dichlorophenyl)-8-(1h-imidazol-2-yl)pyrido[4,3-d]pyrimidin-5-one Chemical compound N=1C(N)=NC=C(C2=O)C=1C(C=1NC=CN=1)=CN2C1=C(Cl)C=CC=C1Cl XIPFHAWJSGGGPQ-UHFFFAOYSA-N 0.000 claims 1
• CQZXDCLATNWQQZ-UHFFFAOYSA-N 6,8-dimethyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C)C=C(C)C2=N1 CQZXDCLATNWQQZ-UHFFFAOYSA-N 0.000 claims 1
• LKCXJVXBLGUQLS-UHFFFAOYSA-N 6-(2,5-dichlorophenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=CN1C1=CC(Cl)=CC=C1Cl LKCXJVXBLGUQLS-UHFFFAOYSA-N 0.000 claims 1
• MIUBKIYRAXCJIU-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)amino]-8-ethenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C(C)(C)CNCC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(C=C)=CN2C1=C(Cl)C=CC=C1Cl MIUBKIYRAXCJIU-UHFFFAOYSA-N 0.000 claims 1
• ASWALLSSOKXUQL-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)amino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4C(C(CNC4)(C)C)=CC=3)N=C2C(C)=CN1C1=C(Cl)C=CC=C1Cl ASWALLSSOKXUQL-UHFFFAOYSA-N 0.000 claims 1
• CMEQFADKTUIHOO-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxopyrido[4,3-d]pyrimidine-8-carbaldehyde Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C=O)C2=N1 CMEQFADKTUIHOO-UHFFFAOYSA-N 0.000 claims 1
• YDMNUKRSAVGCQM-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-(4-methylpiperazin-1-yl)anilino]-8-[(2,2,2-trifluoroethylamino)methyl]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(CNCC(F)(F)F)C2=N1 YDMNUKRSAVGCQM-UHFFFAOYSA-N 0.000 claims 1
• HXZJOJDQTHEMAD-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[2-(dimethylamino)ethylamino]anilino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(NCCN(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 HXZJOJDQTHEMAD-UHFFFAOYSA-N 0.000 claims 1
• VEISEJCVUWRJGG-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[2-(dimethylamino)ethylsulfanyl]anilino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(SCCN(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 VEISEJCVUWRJGG-UHFFFAOYSA-N 0.000 claims 1
• IOHMJWXZEFFFOM-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[2-(dimethylamino)ethylsulfonyl]anilino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(S(=O)(=O)CCN(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 IOHMJWXZEFFFOM-UHFFFAOYSA-N 0.000 claims 1
• LRGODSVHKJTERV-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-(fluoromethyl)pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(CF)C2=N1 LRGODSVHKJTERV-UHFFFAOYSA-N 0.000 claims 1
• KLNTWQFFYINWGG-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-(hydroxymethyl)pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(CO)C2=N1 KLNTWQFFYINWGG-UHFFFAOYSA-N 0.000 claims 1
• GWDGQFOINGYQNX-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-ethenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C=C)C2=N1 GWDGQFOINGYQNX-UHFFFAOYSA-N 0.000 claims 1
• MCRKRMLKCMUFDV-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 MCRKRMLKCMUFDV-UHFFFAOYSA-N 0.000 claims 1
• CUNXQDQMSJICOC-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-[2-(dimethylamino)ethyl]piperazin-1-yl]anilino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(CCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 CUNXQDQMSJICOC-UHFFFAOYSA-N 0.000 claims 1
• RGBZKKMZCHLFNC-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-[3-(dimethylamino)propyl]piperazin-1-yl]anilino]-8-(fluoromethyl)pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(CCCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(CF)C2=N1 RGBZKKMZCHLFNC-UHFFFAOYSA-N 0.000 claims 1
• TZDQYQGVRAIVRG-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-[3-(dimethylamino)propyl]piperazin-1-yl]anilino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(CCCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 TZDQYQGVRAIVRG-UHFFFAOYSA-N 0.000 claims 1
• FPKNDQJSHUPUFU-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[[2-(dimethylamino)-2,3-dihydro-1h-inden-5-yl]amino]-8-(hydroxymethyl)pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C2CC(N(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1C(CO)=CN2C1=C(Cl)C=CC=C1Cl FPKNDQJSHUPUFU-UHFFFAOYSA-N 0.000 claims 1
• XNKJFJJPOSELAO-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[[2-(dimethylamino)-2,3-dihydro-1h-inden-5-yl]amino]-8-ethenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C2CC(N(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1C(C=C)=CN2C1=C(Cl)C=CC=C1Cl XNKJFJJPOSELAO-UHFFFAOYSA-N 0.000 claims 1
• NFXWJHGRCDFSTE-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(1-hydroxyethyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C2C(C(O)C)=CN1C1=C(Cl)C=CC=C1Cl NFXWJHGRCDFSTE-UHFFFAOYSA-N 0.000 claims 1
• UYXHKNZXQUASFC-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(1h-imidazol-2-yl)-2-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4CCNCC4=CC=3)N=C2C(C=2NC=CN=2)=C1 UYXHKNZXQUASFC-UHFFFAOYSA-N 0.000 claims 1
• JEBLLDTYWCQIIF-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(1h-imidazol-2-yl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C=3NC=CN=3)C2=N1 JEBLLDTYWCQIIF-UHFFFAOYSA-N 0.000 claims 1
• ORPPVRBOTBKNJV-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(difluoromethyl)-2-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CCNCC4=CC=3)N=C2C(C(F)F)=CN1C1=C(Cl)C=CC=C1Cl ORPPVRBOTBKNJV-UHFFFAOYSA-N 0.000 claims 1
• ZEDRBKISKNUZRX-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(difluoromethyl)-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C(F)F)=CN1C1=C(Cl)C=CC=C1Cl ZEDRBKISKNUZRX-UHFFFAOYSA-N 0.000 claims 1
• JJAKZUOKXIRQLV-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(difluoromethyl)-2-(spiro[2,3-dihydro-1h-isoquinoline-4,1'-cyclopropane]-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4C(C5(CC5)CNC4)=CC=3)N=C2C(C(F)F)=CN1C1=C(Cl)C=CC=C1Cl JJAKZUOKXIRQLV-UHFFFAOYSA-N 0.000 claims 1
• MTKUPYVBTYRGEW-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(difluoromethyl)-2-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(C(F)F)=CN2C1=C(Cl)C=CC=C1Cl MTKUPYVBTYRGEW-UHFFFAOYSA-N 0.000 claims 1
• KDXSQCJVXUMBDG-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(difluoromethyl)-2-[(2-pyrrolidin-1-yl-2,3-dihydro-1h-inden-5-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CC(CC4=CC=3)N3CCCC3)N=C2C(C(F)F)=CN1C1=C(Cl)C=CC=C1Cl KDXSQCJVXUMBDG-UHFFFAOYSA-N 0.000 claims 1
• QZODMNORYIASOV-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(difluoromethyl)-2-[(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C(C)(C)CNCC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(C(F)F)=CN2C1=C(Cl)C=CC=C1Cl QZODMNORYIASOV-UHFFFAOYSA-N 0.000 claims 1
• IULFAUIYXWGQCV-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(difluoromethyl)-2-[4-(1-methylpiperidin-4-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCC1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C(F)F)C2=N1 IULFAUIYXWGQCV-UHFFFAOYSA-N 0.000 claims 1
• LQEGKLLSZUMQJD-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(difluoromethyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C(F)F)C2=N1 LQEGKLLSZUMQJD-UHFFFAOYSA-N 0.000 claims 1
• BDWBTEXDEIRDSP-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(difluoromethyl)-2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C(F)F)C2=N1 BDWBTEXDEIRDSP-UHFFFAOYSA-N 0.000 claims 1
• XBLBOOAURVCRPR-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(difluoromethyl)-2-[[2-(dimethylamino)-2,3-dihydro-1h-inden-5-yl]amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C2CC(N(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1C(C(F)F)=CN2C1=C(Cl)C=CC=C1Cl XBLBOOAURVCRPR-UHFFFAOYSA-N 0.000 claims 1
• CXXMWFYGMJVCHX-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(fluoromethyl)-2-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CCNCC4=CC=3)N=C2C(CF)=CN1C1=C(Cl)C=CC=C1Cl CXXMWFYGMJVCHX-UHFFFAOYSA-N 0.000 claims 1
• QCYXQYWEZOPLCT-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(fluoromethyl)-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(CF)=CN1C1=C(Cl)C=CC=C1Cl QCYXQYWEZOPLCT-UHFFFAOYSA-N 0.000 claims 1
• NGKJGNSYTJFBQL-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(fluoromethyl)-2-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(CF)=CN2C1=C(Cl)C=CC=C1Cl NGKJGNSYTJFBQL-UHFFFAOYSA-N 0.000 claims 1
• FXHJGACESKCNMW-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(fluoromethyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(CF)C2=N1 FXHJGACESKCNMW-UHFFFAOYSA-N 0.000 claims 1
• BCSZBAOFXMMRNR-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(hydroxymethyl)-2-(spiro[2,3-dihydro-1h-isoquinoline-4,1'-cyclopropane]-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4C(C5(CC5)CNC4)=CC=3)N=C2C(CO)=CN1C1=C(Cl)C=CC=C1Cl BCSZBAOFXMMRNR-UHFFFAOYSA-N 0.000 claims 1
• ICNHYRCGEFUMGJ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(hydroxymethyl)-2-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(CO)=CN2C1=C(Cl)C=CC=C1Cl ICNHYRCGEFUMGJ-UHFFFAOYSA-N 0.000 claims 1
• QGGTYEMGJOXMSU-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(hydroxymethyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(CO)C2=N1 QGGTYEMGJOXMSU-UHFFFAOYSA-N 0.000 claims 1
• UWJCOOVWMGHOTO-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-ethenyl-2-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4CCNCC4=CC=3)N=C2C(C=C)=C1 UWJCOOVWMGHOTO-UHFFFAOYSA-N 0.000 claims 1
• LZUZUJHSSBCEEB-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-ethenyl-2-(spiro[2,3-dihydro-1h-isoquinoline-4,1'-cyclopropane]-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CNC4)=CC=3)N=C2C(C=C)=C1 LZUZUJHSSBCEEB-UHFFFAOYSA-N 0.000 claims 1
• YHGQCXIIDLUJNK-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-ethenyl-2-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(C=C)=CN2C1=C(Cl)C=CC=C1Cl YHGQCXIIDLUJNK-UHFFFAOYSA-N 0.000 claims 1
• UXTFHTKPRASUBX-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-ethenyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C=C)C2=N1 UXTFHTKPRASUBX-UHFFFAOYSA-N 0.000 claims 1
• YUSYOVQCLQWHLZ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-ethyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C2C(CC)=CN1C1=C(Cl)C=CC=C1Cl YUSYOVQCLQWHLZ-UHFFFAOYSA-N 0.000 claims 1
• XMQJCJFHZMUVAB-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CCNCC4=CC=3)N=C2C(C)=CN1C1=C(Cl)C=CC=C1Cl XMQJCJFHZMUVAB-UHFFFAOYSA-N 0.000 claims 1
• OQOHIURRUYATLU-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=CN1C1=C(Cl)C=CC=C1Cl OQOHIURRUYATLU-UHFFFAOYSA-N 0.000 claims 1
• IQEYYXYQTVYXBO-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-(spiro[2,3-dihydro-1h-isoquinoline-4,1'-cyclopropane]-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4C(C5(CC5)CNC4)=CC=3)N=C2C(C)=CN1C1=C(Cl)C=CC=C1Cl IQEYYXYQTVYXBO-UHFFFAOYSA-N 0.000 claims 1
• GDHLEUDTJFQFFL-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[(1,1,2-trimethyl-3h-isoindol-5-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C(C)(C)N(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(C)=CN2C1=C(Cl)C=CC=C1Cl GDHLEUDTJFQFFL-UHFFFAOYSA-N 0.000 claims 1
• MRICUEKQRIIKLY-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C(C)(C)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(C)=CN2C1=C(Cl)C=CC=C1Cl MRICUEKQRIIKLY-UHFFFAOYSA-N 0.000 claims 1
• UWJHZJSULUUDDG-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(C)=CN2C1=C(Cl)C=CC=C1Cl UWJHZJSULUUDDG-UHFFFAOYSA-N 0.000 claims 1
• FSRYXGSLNYBDRQ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 FSRYXGSLNYBDRQ-UHFFFAOYSA-N 0.000 claims 1
• FATOTGXJWIVGOB-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[4-[(1-methylpiperidin-4-yl)amino]anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCC1NC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 FATOTGXJWIVGOB-UHFFFAOYSA-N 0.000 claims 1
• OZPOBYUXNUYJQC-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[4-[(1-methylpyrrolidin-3-yl)amino]anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1N(C)CCC1NC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 OZPOBYUXNUYJQC-UHFFFAOYSA-N 0.000 claims 1
• UZVQUUHOVUSBKL-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[[2-(1-methylpiperidin-4-yl)-1,3-dihydroisoindol-5-yl]amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCC1N1CC2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5Cl)Cl)C=C4C)=O)=CN=3)=CC=C2C1 UZVQUUHOVUSBKL-UHFFFAOYSA-N 0.000 claims 1
• PVRCQHMRBCHRSK-UHFFFAOYSA-N 6-(2,6-dimethylphenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=CC=CC(C)=C1N1C(=O)C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=C1 PVRCQHMRBCHRSK-UHFFFAOYSA-N 0.000 claims 1
• WJSOZJPUPCAYNM-UHFFFAOYSA-N 6-(2,6-dimethylphenyl)-8-methyl-2-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(C)=CN2C1=C(C)C=CC=C1C WJSOZJPUPCAYNM-UHFFFAOYSA-N 0.000 claims 1
• RFGWRGAIFJOJNW-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-2-[(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)amino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4C(C(CNC4)(C)C)=CC=3)N=C2C(C)=CN1C1=C(F)C=CC=C1Cl RFGWRGAIFJOJNW-UHFFFAOYSA-N 0.000 claims 1
• OTCYTUFDEPMDLX-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-ethenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C=C(C=C)C2=N1 OTCYTUFDEPMDLX-UHFFFAOYSA-N 0.000 claims 1
• DMPOPQBEWPPQJG-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C=C(C)C2=N1 DMPOPQBEWPPQJG-UHFFFAOYSA-N 0.000 claims 1
• KHFGDQHUGMBJLF-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-2-[[2-(dimethylamino)-2,3-dihydro-1h-inden-5-yl]amino]-8-ethenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C2CC(N(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1C(C=C)=CN2C1=C(F)C=CC=C1Cl KHFGDQHUGMBJLF-UHFFFAOYSA-N 0.000 claims 1
• PMNFFWIJQGLZBI-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-2-[[2-(dimethylamino)-2,3-dihydro-1h-inden-5-yl]amino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C2CC(N(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1C(C)=CN2C1=C(F)C=CC=C1Cl PMNFFWIJQGLZBI-UHFFFAOYSA-N 0.000 claims 1
• QLWDYVQNRWZAFZ-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-8-ethenyl-2-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(C=C)=CN2C1=C(F)C=CC=C1Cl QLWDYVQNRWZAFZ-UHFFFAOYSA-N 0.000 claims 1
• HVFGOXDXOUUWKQ-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-8-ethenyl-2-[4-(1-methylpiperidin-4-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCC1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C=C(C=C)C2=N1 HVFGOXDXOUUWKQ-UHFFFAOYSA-N 0.000 claims 1
• BVEWBOMBOLSOHJ-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-8-ethenyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C=C(C=C)C2=N1 BVEWBOMBOLSOHJ-UHFFFAOYSA-N 0.000 claims 1
• GTBWBZWWNRQTNQ-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CCNCC4=CC=3)N=C2C(C)=CN1C1=C(F)C=CC=C1Cl GTBWBZWWNRQTNQ-UHFFFAOYSA-N 0.000 claims 1
• OGNOENSJAANEQI-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=CN1C1=C(F)C=CC=C1Cl OGNOENSJAANEQI-UHFFFAOYSA-N 0.000 claims 1
• ZCPLEVZNBRJYFU-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-8-methyl-2-(spiro[2,3-dihydro-1h-isoquinoline-4,1'-cyclopropane]-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4C(C5(CC5)CNC4)=CC=3)N=C2C(C)=CN1C1=C(F)C=CC=C1Cl ZCPLEVZNBRJYFU-UHFFFAOYSA-N 0.000 claims 1
• ASHRONWSMMZCPQ-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-8-methyl-2-[(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C(C)(C)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(C)=CN2C1=C(F)C=CC=C1Cl ASHRONWSMMZCPQ-UHFFFAOYSA-N 0.000 claims 1
• SDQHATKGJVNXTG-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-8-methyl-2-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(C)=CN2C1=C(F)C=CC=C1Cl SDQHATKGJVNXTG-UHFFFAOYSA-N 0.000 claims 1
• ZSOAQVMQSGGAKV-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-8-methyl-2-[4-(1-methylpiperidin-4-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCC1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C=C(C)C2=N1 ZSOAQVMQSGGAKV-UHFFFAOYSA-N 0.000 claims 1
• ROUQEAATTQFFOU-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-8-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C=C(C)C2=N1 ROUQEAATTQFFOU-UHFFFAOYSA-N 0.000 claims 1
• VIZVSJPPHXMXTK-UHFFFAOYSA-N 6-(2-chloro-6-hydroxyphenyl)-2-[(1,1-dimethyl-2,3-dihydroisoindol-5-yl)amino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4C(C(NC4)(C)C)=CC=3)N=C2C(C)=CN1C1=C(O)C=CC=C1Cl VIZVSJPPHXMXTK-UHFFFAOYSA-N 0.000 claims 1
• RDVFITYJSAWYNT-UHFFFAOYSA-N 6-(2-chloro-6-methylphenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=C1 RDVFITYJSAWYNT-UHFFFAOYSA-N 0.000 claims 1
• OMKMHZXOIADPQD-UHFFFAOYSA-N 6-(2-chloro-6-methylphenyl)-8-methyl-2-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(C)=CN2C1=C(C)C=CC=C1Cl OMKMHZXOIADPQD-UHFFFAOYSA-N 0.000 claims 1
• QYPMNKSDMDOZIG-UHFFFAOYSA-N 6-(2-chlorophenyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrimido[5,4-c]quinolin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=CC=CC=C3C2=N1 QYPMNKSDMDOZIG-UHFFFAOYSA-N 0.000 claims 1
• YGSRULFQZLIPBD-UHFFFAOYSA-N 6-(2-chlorophenyl)-2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C=C(C)C2=N1 YGSRULFQZLIPBD-UHFFFAOYSA-N 0.000 claims 1
• VSISFCYRKXKDDP-UHFFFAOYSA-N 6-(2-chlorophenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=CN1C1=CC=CC=C1Cl VSISFCYRKXKDDP-UHFFFAOYSA-N 0.000 claims 1
• FZRKNHNZPSPQOX-UHFFFAOYSA-N 6-(2-fluoro-6-methylphenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=CC=CC(F)=C1N1C(=O)C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=C1 FZRKNHNZPSPQOX-UHFFFAOYSA-N 0.000 claims 1
• PEHBXIFRLYTHFB-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=NOC(C)=C1N1C(=O)C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=C1 PEHBXIFRLYTHFB-UHFFFAOYSA-N 0.000 claims 1
• XYBGTEBCRYGFRZ-UHFFFAOYSA-N 6-(3,5-dimethyl-1h-pyrazol-4-yl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=NNC(C)=C1N1C(=O)C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=C1 XYBGTEBCRYGFRZ-UHFFFAOYSA-N 0.000 claims 1
• LQDNMOQCSLYSSQ-UHFFFAOYSA-N 6-[(2,6-dichlorophenyl)methyl]-2-[4-(4-methylpiperazin-1-yl)anilino]-8-phenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=3C(=CC=CC=3Cl)Cl)C=C(C=3C=CC=CC=3)C2=N1 LQDNMOQCSLYSSQ-UHFFFAOYSA-N 0.000 claims 1
• DLBPLCZMOFSTQJ-UHFFFAOYSA-N 6-[(2-chloro-4-fluorophenyl)methyl]-2-[4-(4-methylpiperazin-1-yl)anilino]-8-phenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=3C(=CC(F)=CC=3)Cl)C=C(C=3C=CC=CC=3)C2=N1 DLBPLCZMOFSTQJ-UHFFFAOYSA-N 0.000 claims 1
• DMGWREWQKGLDGY-UHFFFAOYSA-N 6-[(2-chlorophenyl)methyl]-2-[4-(4-methylpiperazin-1-yl)anilino]-8-phenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=3C(=CC=CC=3)Cl)C=C(C=3C=CC=CC=3)C2=N1 DMGWREWQKGLDGY-UHFFFAOYSA-N 0.000 claims 1
• FEHAJMRCHPXYCX-UHFFFAOYSA-N 6-[(2-fluorophenyl)methyl]-2-[4-(4-methylpiperazin-1-yl)anilino]-8-phenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=3C(=CC=CC=3)F)C=C(C=3C=CC=CC=3)C2=N1 FEHAJMRCHPXYCX-UHFFFAOYSA-N 0.000 claims 1
• IHESTPUIBPGRGD-UHFFFAOYSA-N 6-[(2-methylphenyl)methyl]-2-[4-(4-methylpiperazin-1-yl)anilino]-8-phenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=3C(=CC=CC=3)C)C=C(C=3C=CC=CC=3)C2=N1 IHESTPUIBPGRGD-UHFFFAOYSA-N 0.000 claims 1
• QUGGIFCWZHDDJY-UHFFFAOYSA-N 6-[(3-methylphenyl)methyl]-2-[4-(4-methylpiperazin-1-yl)anilino]-8-phenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=3C=C(C)C=CC=3)C=C(C=3C=CC=CC=3)C2=N1 QUGGIFCWZHDDJY-UHFFFAOYSA-N 0.000 claims 1
• LMJUPASVNYCPMJ-UHFFFAOYSA-N 6-[(4-tert-butylphenyl)methyl]-2-[4-(4-methylpiperazin-1-yl)anilino]-8-phenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=3C=CC(=CC=3)C(C)(C)C)C=C(C=3C=CC=CC=3)C2=N1 LMJUPASVNYCPMJ-UHFFFAOYSA-N 0.000 claims 1
• IPAQMKVFRZHHSI-UHFFFAOYSA-N 6-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-2-[4-(4-methylpiperazin-1-yl)anilino]-8-phenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=3C(=CC=CC=3F)C(F)(F)F)C=C(C=3C=CC=CC=3)C2=N1 IPAQMKVFRZHHSI-UHFFFAOYSA-N 0.000 claims 1
• PPWHIKAVOHZKDJ-UHFFFAOYSA-N 6-benzyl-2-[4-(4-methylpiperazin-1-yl)anilino]-8-phenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=3C=CC=CC=3)C=C(C=3C=CC=CC=3)C2=N1 PPWHIKAVOHZKDJ-UHFFFAOYSA-N 0.000 claims 1
• CQCOKGXMKCCDON-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-5-methyl-3-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-e][1,2,4]triazin-8-one Chemical compound O=C1C2=NN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=CN1C1=C(Cl)C=CC=C1Cl CQCOKGXMKCCDON-UHFFFAOYSA-N 0.000 claims 1
• BJPVSVDOEJXFKJ-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-5-methyl-3-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]pyrido[4,3-e][1,2,4]triazin-8-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NN=C(C2=O)C=1C(C)=CN2C1=C(Cl)C=CC=C1Cl BJPVSVDOEJXFKJ-UHFFFAOYSA-N 0.000 claims 1
• GOTUVURGWVIRBL-UHFFFAOYSA-N 8-(1,3-benzothiazol-2-yl)-6-(2,6-dichlorophenyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C=3SC4=CC=CC=C4N=3)C2=N1 GOTUVURGWVIRBL-UHFFFAOYSA-N 0.000 claims 1
• JKQMHXBBSMOFEB-UHFFFAOYSA-N 8-(1h-benzimidazol-2-yl)-6-(2,6-dichlorophenyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C=3NC4=CC=CC=C4N=3)C2=N1 JKQMHXBBSMOFEB-UHFFFAOYSA-N 0.000 claims 1
• SFTMBSQCWWKVIO-UHFFFAOYSA-N 8-(anilinomethyl)-6-(2,6-dichlorophenyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(CNC=3C=CC=CC=3)C2=N1 SFTMBSQCWWKVIO-UHFFFAOYSA-N 0.000 claims 1
• QQFZTSWFVDLLJQ-UHFFFAOYSA-N 8-(cyclohexen-1-yl)-6-(cyclopropylmethyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC3CC3)C=C(C=3CCCCC=3)C2=N1 QQFZTSWFVDLLJQ-UHFFFAOYSA-N 0.000 claims 1
• LTRBTLMMISJIHT-UHFFFAOYSA-N 8-(cyclohexen-1-yl)-6-ethyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C(=O)N(CC)C=C1C1=CCCCC1 LTRBTLMMISJIHT-UHFFFAOYSA-N 0.000 claims 1
• MGQLSFJVJBAZOT-UHFFFAOYSA-N 8-(cyclopenten-1-yl)-6-(cyclopropylmethyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC3CC3)C=C(C=3CCCC=3)C2=N1 MGQLSFJVJBAZOT-UHFFFAOYSA-N 0.000 claims 1
• PKFRDFNICPPTJM-UHFFFAOYSA-N 8-bromo-6-[(2,6-difluorophenyl)methyl]-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=3C(=CC=CC=3F)F)C=C(Br)C2=N1 PKFRDFNICPPTJM-UHFFFAOYSA-N 0.000 claims 1
• MOWKGLCJEOGRKN-UHFFFAOYSA-N 8-methyl-6-[2-(1,3-oxazol-5-yl)phenyl]-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=CN1C1=CC=CC=C1C1=CN=CO1 MOWKGLCJEOGRKN-UHFFFAOYSA-N 0.000 claims 1
• RJVYXSZUAPKZFK-UHFFFAOYSA-N 8-methyl-6-naphthalen-1-yl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CNCC2=CC(NC3=NC=C4C(=O)N(C=5C6=CC=CC=C6C=CC=5)C=C(C4=N3)C)=CC=C21 RJVYXSZUAPKZFK-UHFFFAOYSA-N 0.000 claims 1
• DJVLJEBOSFQPRO-XUTJKUGGSA-N C1C[C@@H](N(C)C)CC[C@@H]1NC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 Chemical compound C1C[C@@H](N(C)C)CC[C@@H]1NC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 DJVLJEBOSFQPRO-XUTJKUGGSA-N 0.000 claims 1
• DJVLJEBOSFQPRO-TYKWCNGQSA-N C1C[C@H](N(C)C)CC[C@@H]1NC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 Chemical compound C1C[C@H](N(C)C)CC[C@@H]1NC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 DJVLJEBOSFQPRO-TYKWCNGQSA-N 0.000 claims 1
• VIWKZJSNEDMPQU-UHFFFAOYSA-N ethyl 2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxo-6-phenylpyrido[4,3-d]pyrimidine-8-carboxylate Chemical compound O=C1C2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C2C(C(=O)OCC)=CN1C1=CC=CC=C1 VIWKZJSNEDMPQU-UHFFFAOYSA-N 0.000 claims 1
• IOWAWPCKYXKUCM-UHFFFAOYSA-N ethyl 2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxo-6-prop-2-enylpyrido[4,3-d]pyrimidine-8-carboxylate Chemical compound N1=C2C(C(=O)OCC)=CN(CC=C)C(=O)C2=CN=C1NC(C=C1)=CC=C1N1CCN(C)CC1 IOWAWPCKYXKUCM-UHFFFAOYSA-N 0.000 claims 1
• WYMCXNNNLUFDOM-UHFFFAOYSA-N ethyl 6-(2-chlorophenyl)-2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxopyrido[4,3-d]pyrimidine-8-carboxylate Chemical compound O=C1C2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C2C(C(=O)OCC)=CN1C1=CC=CC=C1Cl WYMCXNNNLUFDOM-UHFFFAOYSA-N 0.000 claims 1
• ZOFMNHOJZFIBEM-UHFFFAOYSA-N ethyl 6-benzyl-2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxopyrido[4,3-d]pyrimidine-8-carboxylate Chemical compound O=C1C2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C2C(C(=O)OCC)=CN1CC1=CC=CC=C1 ZOFMNHOJZFIBEM-UHFFFAOYSA-N 0.000 claims 1
• OMCXOLXTMJCBLN-UHFFFAOYSA-N methyl 5-[[6-(2,6-dichlorophenyl)-8-methyl-5-oxopyrido[4,3-d]pyrimidin-2-yl]amino]-2-(4-methylpiperazin-1-yl)benzoate Chemical compound C=1C=C(N2CCN(C)CC2)C(C(=O)OC)=CC=1NC(N=1)=NC=C(C2=O)C=1C(C)=CN2C1=C(Cl)C=CC=C1Cl OMCXOLXTMJCBLN-UHFFFAOYSA-N 0.000 claims 1
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