ES2606640T3 - Inhibidores de cinasas de tipo piridopirimidinona - Google Patents

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Publication number

ES2606640T3

ES2606640T3 ES13707095.9T ES13707095T ES2606640T3 ES 2606640 T3 ES2606640 T3 ES 2606640T3 ES 13707095 T ES13707095 T ES 13707095T ES 2606640 T3 ES2606640 T3 ES 2606640T3

Authority

ES

Spain

Prior art keywords

alkyl

pyrimidin

amino

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.)

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• 229940043355 kinase inhibitor Drugs 0.000 title description 12
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 12
• 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
• -1 C1- alkyl 6 Chemical group 0.000 claims abstract description 341
• 150000001875 compounds Chemical class 0.000 claims abstract description 301
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 292
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 166
• 125000003118 aryl group Chemical group 0.000 claims abstract description 151
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 145
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 145
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 139
• 125000001424 substituent group Chemical group 0.000 claims abstract description 121
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 113
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 95
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 82
• 239000001257 hydrogen Substances 0.000 claims abstract description 81
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 68
• 150000003839 salts Chemical class 0.000 claims abstract description 59
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 43
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 38
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 37
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 36
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 35
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims abstract description 35
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 34
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 34
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims abstract description 34
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 33
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 29
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 27
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 25
• 239000012453 solvate Substances 0.000 claims abstract description 22
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 12
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 12
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 9
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 6
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 3
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 3
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract description 3
• 125000002619 bicyclic group Chemical group 0.000 claims abstract description 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
• 229910052703 rhodium Inorganic materials 0.000 claims abstract description 3
• 125000001475 halogen functional group Chemical group 0.000 claims abstract 49
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 26
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 238
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 115
• 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 64
• BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims description 48
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
• 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 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 206010028980 Neoplasm Diseases 0.000 claims description 21
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 19
• 238000000034 method Methods 0.000 claims description 16
• CGJYYORLGIGJEG-UHFFFAOYSA-N 2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane] Chemical compound C1N(C)CC2=CC=CC=C2C21CC2 CGJYYORLGIGJEG-UHFFFAOYSA-N 0.000 claims description 14
• 201000011510 cancer Diseases 0.000 claims description 13
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 13
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 8
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 6
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 6
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
• 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 4
• 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 description 4
• JCNQHHRWQHCLQK-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-6-phenylpyrimido[5,4-c]quinolin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C=CC=CC=3)C3=CC=CC=C3C2=N1 JCNQHHRWQHCLQK-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 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 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• VVKRBFDUUPZPJF-UHFFFAOYSA-N 6-(2-chlorophenyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrimido[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)Cl)C3=NC=CC=C3C2=N1 VVKRBFDUUPZPJF-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 4
• 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 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
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 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
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 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 description 3
• 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 description 3
• ALMUSLUKAWFXQQ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-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(Cl)C=CC=C1Cl ALMUSLUKAWFXQQ-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 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 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
• 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
• 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
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