MX2014010176A

MX2014010176A - Inhibidores de cinasas de piridopirimidinona.

Inhibidores de cinasas de piridopirimidinona.

Info

Publication number: MX2014010176A
Authority: MX; Mexico
Prior art keywords: amino; alkyl; phenyl; pyrimidin; methyl
Prior art date: 2012-02-23

Application number

MX2014010176A

Other languages

English (en)

Spanish (es)

Inventor

Anthony Mastracchio

Chunqiu Lai

Keith Woods

Virajkumar B Gandhi

Thomas Penning

Original Assignee

Abbvie Inc

Priority date

2012-02-23

Filing date

2013-02-22

Publication date

2014-11-10

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

2014-11-10 Publication of MX2014010176A publication Critical patent/MX2014010176A/es

Links

108091000080 Phosphotransferase Proteins 0.000 title abstract description 19
102000020233 phosphotransferase Human genes 0.000 title abstract description 19
239000003112 inhibitor Substances 0.000 title description 38
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 1
150000001875 compounds Chemical class 0.000 claims abstract description 313
150000003839 salts Chemical class 0.000 claims abstract description 57
206010028980 Neoplasm Diseases 0.000 claims abstract description 23
238000000034 method Methods 0.000 claims abstract description 15
201000011510 cancer Diseases 0.000 claims abstract description 13
-1 aryl-C ^ e- Chemical group 0.000 claims description 516
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 247
125000000217 alkyl group Chemical group 0.000 claims description 221
229910052736 halogen Inorganic materials 0.000 claims description 151
150000002367 halogens Chemical class 0.000 claims description 142
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 128
125000001188 haloalkyl group Chemical group 0.000 claims description 117
125000003118 aryl group Chemical group 0.000 claims description 113
125000001072 heteroaryl group Chemical group 0.000 claims description 111
125000001424 substituent group Chemical group 0.000 claims description 110
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 104
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 97
125000000753 cycloalkyl group Chemical group 0.000 claims description 89
229910052739 hydrogen Inorganic materials 0.000 claims description 73
239000001257 hydrogen Substances 0.000 claims description 66
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 42
125000001624 naphthyl group Chemical group 0.000 claims description 41
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 41
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 40
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 40
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 38
BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims description 38
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 37
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 35
125000003342 alkenyl group Chemical group 0.000 claims description 35
125000004043 oxo group Chemical group O=* 0.000 claims description 33
125000003545 alkoxy group Chemical group 0.000 claims description 32
125000000623 heterocyclic group Chemical group 0.000 claims description 30
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 22
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 22
239000012453 solvate Substances 0.000 claims description 22
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 20
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 19
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 18
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
125000004438 haloalkoxy group Chemical group 0.000 claims description 18
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 13
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 8
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
PKKDWPSOOQBWFB-UHFFFAOYSA-N 2,4-dichloro-6-[(3,5-dichloro-2-hydroxyphenyl)methyl]phenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1CC1=CC(Cl)=CC(Cl)=C1O PKKDWPSOOQBWFB-UHFFFAOYSA-N 0.000 claims description 7
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 6
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000002950 monocyclic group Chemical group 0.000 claims description 5
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
125000003352 4-tert-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
NVUONPSPPJQARI-UHFFFAOYSA-N 7h-pyrido[4,3-e][1,2,4]triazin-8-one Chemical compound C1=NN=C2C(=O)NC=CC2=N1 NVUONPSPPJQARI-UHFFFAOYSA-N 0.000 claims description 3
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 3
125000001316 cycloalkyl alkyl group Chemical group 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
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 3
CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
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 description 2
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 description 2
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 description 2
WIDVDMOQFQSPCF-UHFFFAOYSA-N 2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-methyl-6-[2-(1,3-oxazol-5-yl)phenyl]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=3)C=3OC=NC=3)C=C(C)C2=N1 WIDVDMOQFQSPCF-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
HOUHOTYYSIYDFC-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)amino]-8-(hydroxymethyl)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(CO)=CN2C1=C(Cl)C=CC=C1Cl HOUHOTYYSIYDFC-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000002619 bicyclic group Chemical group 0.000 claims description 2
229940095102 methyl benzoate Drugs 0.000 claims description 2
229910052705 radium Inorganic materials 0.000 claims description 2
229910052702 rhenium Inorganic materials 0.000 claims description 2
229910052703 rhodium Inorganic materials 0.000 claims description 2
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 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 3
GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 3
125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 3
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
DFPKHQPIXTVYBE-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-6-phenylpyrimido[5,4-c][1,8]naphthyridin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C=CC=CC=3)C3=NC=CC=C3C2=N1 DFPKHQPIXTVYBE-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
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
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
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
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 1
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 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
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 114
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 14
201000010099 disease Diseases 0.000 abstract description 11
230000002401 inhibitory effect Effects 0.000 abstract description 3
239000000047 product Substances 0.000 description 198
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 138
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 114
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
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