CA2864142A1

CA2864142A1 - Pyridopyrimidinone inhibitors of kinases

Pyridopyrimidinone inhibitors of kinases Download PDF

Info

Publication number: CA2864142A1
Authority: CA; Canada
Prior art keywords: pyrimidin; amino; alkyl; phenyl; pyrido
Prior art date: 2012-02-23
Legal status : Abandoned

Application number

CA2864142A

Other languages

English (en)

French (fr)

Inventor

Keith Woods

Anthony Mastracchio

Chunqiu Lai

Virajkumar B. Gandhi

Thomas Penning

Current Assignee

AbbVie Inc

Original Assignee

AbbVie Inc

Priority date

2012-02-23

Filing date

2013-02-22

Publication date

2013-08-29

2013-02-22 Application filed by AbbVie Inc filed Critical AbbVie Inc

2013-08-29 Publication of CA2864142A1 publication Critical patent/CA2864142A1/en

Status Abandoned legal-status Critical Current

Links

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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230000002401 inhibitory effect Effects 0.000 abstract description 3
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IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 170
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 120
125000005843 halogen group Chemical group 0.000 description 105
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238000005160 1H NMR spectroscopy Methods 0.000 description 95
239000011541 reaction mixture Substances 0.000 description 93
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 89
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 85
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 65
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 65
239000000741 silica gel Substances 0.000 description 65
229910002027 silica gel Inorganic materials 0.000 description 65
229960001866 silicon dioxide Drugs 0.000 description 65
238000003818 flash chromatography Methods 0.000 description 63
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 62
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 59
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 52
239000012071 phase Substances 0.000 description 50
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
238000002953 preparative HPLC Methods 0.000 description 41
229920006395 saturated elastomer Polymers 0.000 description 41
239000000243 solution Substances 0.000 description 38
125000000217 alkyl group Chemical group 0.000 description 36
238000006243 chemical reaction Methods 0.000 description 36
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
229910000030 sodium bicarbonate Inorganic materials 0.000 description 32
235000017557 sodium bicarbonate Nutrition 0.000 description 32
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