US20070244113A1 - Compounds and therapeutical use thereof - Google Patents
Compounds and therapeutical use thereof Download PDFInfo
- Publication number
- US20070244113A1 US20070244113A1 US11/680,843 US68084307A US2007244113A1 US 20070244113 A1 US20070244113 A1 US 20070244113A1 US 68084307 A US68084307 A US 68084307A US 2007244113 A1 US2007244113 A1 US 2007244113A1
- Authority
- US
- United States
- Prior art keywords
- alkyl
- methyl
- independently
- halo
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 242
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 230000006907 apoptotic process Effects 0.000 claims abstract description 37
- 238000011282 treatment Methods 0.000 claims abstract description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 837
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 531
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 440
- 125000000623 heterocyclic group Chemical group 0.000 claims description 271
- 125000001424 substituent group Chemical group 0.000 claims description 259
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 211
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 208
- 229910052757 nitrogen Inorganic materials 0.000 claims description 207
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 169
- 229910052731 fluorine Inorganic materials 0.000 claims description 152
- 229910052739 hydrogen Inorganic materials 0.000 claims description 144
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 125
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 105
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 97
- 150000001356 alkyl thiols Chemical class 0.000 claims description 97
- 150000003839 salts Chemical class 0.000 claims description 92
- 239000012453 solvate Substances 0.000 claims description 91
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 88
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 87
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 84
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 84
- 125000004423 acyloxy group Chemical group 0.000 claims description 84
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 82
- 150000003573 thiols Chemical class 0.000 claims description 82
- 125000002252 acyl group Chemical group 0.000 claims description 80
- 229910052801 chlorine Inorganic materials 0.000 claims description 79
- 125000001072 heteroaryl group Chemical group 0.000 claims description 76
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 74
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 74
- 125000004011 3 membered carbocyclic group Chemical group 0.000 claims description 73
- 125000001845 4 membered carbocyclic group Chemical group 0.000 claims description 73
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 73
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 65
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 63
- 229910052760 oxygen Inorganic materials 0.000 claims description 62
- 229910052717 sulfur Inorganic materials 0.000 claims description 62
- 229910052702 rhenium Inorganic materials 0.000 claims description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
- -1 carbocycle Chemical group 0.000 claims description 55
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 49
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 34
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 32
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 32
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 30
- 229910017912 NH2OH Inorganic materials 0.000 claims description 30
- 229910052720 vanadium Inorganic materials 0.000 claims description 28
- 241000124008 Mammalia Species 0.000 claims description 25
- 102000004243 Tubulin Human genes 0.000 claims description 25
- 108090000704 Tubulin Proteins 0.000 claims description 25
- 102000007537 Type II DNA Topoisomerases Human genes 0.000 claims description 25
- 108010046308 Type II DNA Topoisomerases Proteins 0.000 claims description 25
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 24
- 230000002401 inhibitory effect Effects 0.000 claims description 22
- 102000003952 Caspase 3 Human genes 0.000 claims description 19
- 108090000397 Caspase 3 Proteins 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 230000003213 activating effect Effects 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 230000001939 inductive effect Effects 0.000 claims description 16
- 239000003112 inhibitor Substances 0.000 claims description 13
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 239000002246 antineoplastic agent Substances 0.000 claims description 10
- 201000011510 cancer Diseases 0.000 claims description 9
- 229940041181 antineoplastic drug Drugs 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- PSBCEFQRMKLLLK-UHFFFAOYSA-N 1-n,1-n,4-n-trimethyl-4-n-(2-methylquinazolin-4-yl)benzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 PSBCEFQRMKLLLK-UHFFFAOYSA-N 0.000 claims description 3
- WNVZXGOITGYARK-UHFFFAOYSA-N 2-chloro-n-(6-methoxypyridin-3-yl)-n-methylquinazolin-4-amine Chemical compound C1=NC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 WNVZXGOITGYARK-UHFFFAOYSA-N 0.000 claims description 3
- QWRQKSFUFHTFQT-UHFFFAOYSA-N 4-n-ethyl-4-n-phenyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine Chemical compound N=1C(N)=NC=2CCCCC=2C=1N(CC)C1=CC=CC=C1 QWRQKSFUFHTFQT-UHFFFAOYSA-N 0.000 claims description 3
- 229930012538 Paclitaxel Natural products 0.000 claims description 3
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 3
- 230000001613 neoplastic effect Effects 0.000 claims description 3
- 229960001592 paclitaxel Drugs 0.000 claims description 3
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 3
- 229960003048 vinblastine Drugs 0.000 claims description 3
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 3
- 229960004528 vincristine Drugs 0.000 claims description 3
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims description 3
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims description 3
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims description 2
- HXFFEQHSYUTPMD-UHFFFAOYSA-N 2,5-dichloro-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC(Cl)=C12 HXFFEQHSYUTPMD-UHFFFAOYSA-N 0.000 claims description 2
- QHXFKLORUQEOMR-UHFFFAOYSA-N 2,6-dibromo-1-n-methyl-1-n-(2-methylquinazolin-4-yl)benzene-1,4-diamine Chemical compound N=1C(C)=NC2=CC=CC=C2C=1N(C)C1=C(Br)C=C(N)C=C1Br QHXFKLORUQEOMR-UHFFFAOYSA-N 0.000 claims description 2
- CIINIBVJXMGLHX-UHFFFAOYSA-N 2,6-dichloro-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=C(Cl)C=C12 CIINIBVJXMGLHX-UHFFFAOYSA-N 0.000 claims description 2
- ZWSFLJALKMNMKZ-UHFFFAOYSA-N 2,7-dichloro-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC(Cl)=CC=C12 ZWSFLJALKMNMKZ-UHFFFAOYSA-N 0.000 claims description 2
- MWIVTJPQNXNKGC-UHFFFAOYSA-N 2,8-dichloro-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=C(Cl)C=CC=C12 MWIVTJPQNXNKGC-UHFFFAOYSA-N 0.000 claims description 2
- HADKEDUVFJBONA-UHFFFAOYSA-N 2-(chloromethyl)-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(CCl)=NC2=CC=CC=C12 HADKEDUVFJBONA-UHFFFAOYSA-N 0.000 claims description 2
- JGEQHBFWBZGDSK-UHFFFAOYSA-N 2-(fluoromethyl)-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(CF)=NC2=CC=CC=C12 JGEQHBFWBZGDSK-UHFFFAOYSA-N 0.000 claims description 2
- VPOMDOPASLEYDU-UHFFFAOYSA-N 2-[(2-chloroquinazolin-4-yl)-methylamino]-5-methylbenzoic acid Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1N(C)C1=CC=C(C)C=C1C(O)=O VPOMDOPASLEYDU-UHFFFAOYSA-N 0.000 claims description 2
- DRHTYCHWHRUZLO-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(CN(C)C)=NC2=CC=CC=C12 DRHTYCHWHRUZLO-UHFFFAOYSA-N 0.000 claims description 2
- QWZWVBXBEWQCOS-UHFFFAOYSA-N 2-[[4-(4-methoxy-n-methylanilino)quinazolin-2-yl]amino]ethanol Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(NCCO)=NC2=CC=CC=C12 QWZWVBXBEWQCOS-UHFFFAOYSA-N 0.000 claims description 2
- BMSGSIIHDIWNMJ-UHFFFAOYSA-N 2-[[4-[(6-methoxypyridin-3-yl)-methylamino]quinazolin-2-yl]amino]ethanol Chemical compound C1=NC(OC)=CC=C1N(C)C1=NC(NCCO)=NC2=CC=CC=C12 BMSGSIIHDIWNMJ-UHFFFAOYSA-N 0.000 claims description 2
- KZLTYCZTNLDDTE-UHFFFAOYSA-N 2-azido-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(N=[N+]=[N-])=NC2=CC=CC=C12 KZLTYCZTNLDDTE-UHFFFAOYSA-N 0.000 claims description 2
- LXLCQABGYLAVOO-UHFFFAOYSA-N 2-bromo-1-n-methyl-1-n-(2-methylquinazolin-4-yl)benzene-1,4-diamine Chemical compound N=1C(C)=NC2=CC=CC=C2C=1N(C)C1=CC=C(N)C=C1Br LXLCQABGYLAVOO-UHFFFAOYSA-N 0.000 claims description 2
- UWXHKNYUROKFSM-UHFFFAOYSA-N 2-chloro-6,7-dimethoxy-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC(OC)=C(OC)C=C12 UWXHKNYUROKFSM-UHFFFAOYSA-N 0.000 claims description 2
- FCWVBILVQLPHJJ-UHFFFAOYSA-N 2-chloro-n-(2,3-dimethoxyphenyl)-n-methylquinazolin-4-amine Chemical compound COC1=CC=CC(N(C)C=2C3=CC=CC=C3N=C(Cl)N=2)=C1OC FCWVBILVQLPHJJ-UHFFFAOYSA-N 0.000 claims description 2
- YSYHVEFDFWVFNK-UHFFFAOYSA-N 2-chloro-n-(2,4-dimethoxyphenyl)-n-methylquinazolin-4-amine Chemical compound COC1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 YSYHVEFDFWVFNK-UHFFFAOYSA-N 0.000 claims description 2
- QGDAWZDGEQZCJD-UHFFFAOYSA-N 2-chloro-n-(2,5-dimethoxyphenyl)-n-methylquinazolin-4-amine Chemical compound COC1=CC=C(OC)C(N(C)C=2C3=CC=CC=C3N=C(Cl)N=2)=C1 QGDAWZDGEQZCJD-UHFFFAOYSA-N 0.000 claims description 2
- BZVWKGZJSRCTMQ-UHFFFAOYSA-N 2-chloro-n-(2-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound COC1=CC=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 BZVWKGZJSRCTMQ-UHFFFAOYSA-N 0.000 claims description 2
- REQTXYJALZRJCF-UHFFFAOYSA-N 2-chloro-n-(3,4-dimethoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 REQTXYJALZRJCF-UHFFFAOYSA-N 0.000 claims description 2
- TYNKRAPSWAKMSZ-UHFFFAOYSA-N 2-chloro-n-(3-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound COC1=CC=CC(N(C)C=2C3=CC=CC=C3N=C(Cl)N=2)=C1 TYNKRAPSWAKMSZ-UHFFFAOYSA-N 0.000 claims description 2
- XYRVBFJQGKLWQK-UHFFFAOYSA-N 2-chloro-n-(4-chlorophenyl)-n-methylquinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1N(C)C1=CC=C(Cl)C=C1 XYRVBFJQGKLWQK-UHFFFAOYSA-N 0.000 claims description 2
- YMVUPHSSHKJBOE-UHFFFAOYSA-N 2-chloro-n-(4-ethoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OCC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 YMVUPHSSHKJBOE-UHFFFAOYSA-N 0.000 claims description 2
- FSVVUPYMZOAIRT-UHFFFAOYSA-N 2-chloro-n-(4-methoxyphenyl)-n,5-dimethylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC(C)=C12 FSVVUPYMZOAIRT-UHFFFAOYSA-N 0.000 claims description 2
- UMERRNXQLYCZAW-UHFFFAOYSA-N 2-chloro-n-(4-methoxyphenyl)-n,6-dimethylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=C(C)C=C12 UMERRNXQLYCZAW-UHFFFAOYSA-N 0.000 claims description 2
- WYEXKHFIYNXOOH-UHFFFAOYSA-N 2-chloro-n-(4-methoxyphenyl)-n,7-dimethylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC(C)=CC=C12 WYEXKHFIYNXOOH-UHFFFAOYSA-N 0.000 claims description 2
- YZVGKWIJZRGKHN-UHFFFAOYSA-N 2-chloro-n-(4-methoxyphenyl)-n,8-dimethylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=C(C)C=CC=C12 YZVGKWIJZRGKHN-UHFFFAOYSA-N 0.000 claims description 2
- CIPVUQSDDVFBPO-UHFFFAOYSA-N 2-chloro-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 CIPVUQSDDVFBPO-UHFFFAOYSA-N 0.000 claims description 2
- YWPRUJPTVYELJB-UHFFFAOYSA-N 2-chloro-n-(4-methoxyphenyl)-n-propan-2-ylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C(C)C)C1=NC(Cl)=NC2=CC=CC=C12 YWPRUJPTVYELJB-UHFFFAOYSA-N 0.000 claims description 2
- ODIKAAXWUXCNCY-UHFFFAOYSA-N 2-chloro-n-[(4-methoxyphenyl)methyl]-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1CN(C)C1=NC(Cl)=NC2=CC=CC=C12 ODIKAAXWUXCNCY-UHFFFAOYSA-N 0.000 claims description 2
- OSBPVTLZCTWHGR-UHFFFAOYSA-N 2-chloro-n-cyclohexyl-n-(4-methoxyphenyl)quinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C=1C2=CC=CC=C2N=C(Cl)N=1)C1CCCCC1 OSBPVTLZCTWHGR-UHFFFAOYSA-N 0.000 claims description 2
- FSLMXGLQAJMKIZ-UHFFFAOYSA-N 2-chloro-n-ethyl-n-(4-methoxyphenyl)quinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1N(CC)C1=CC=C(OC)C=C1 FSLMXGLQAJMKIZ-UHFFFAOYSA-N 0.000 claims description 2
- CKZYZMNGKAKNSW-UHFFFAOYSA-N 2-chloro-n-methyl-n-(4-methylphenyl)quinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1N(C)C1=CC=C(C)C=C1 CKZYZMNGKAKNSW-UHFFFAOYSA-N 0.000 claims description 2
- WXELIIFXJNHKGQ-UHFFFAOYSA-N 2-chloro-n-methyl-n-(4-nitrophenyl)quinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1N(C)C1=CC=C([N+]([O-])=O)C=C1 WXELIIFXJNHKGQ-UHFFFAOYSA-N 0.000 claims description 2
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- RVVQCOFJEZMGFO-UHFFFAOYSA-N 2-chloro-n-methyl-n-(4-propoxyphenyl)quinazolin-4-amine Chemical compound C1=CC(OCCC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 RVVQCOFJEZMGFO-UHFFFAOYSA-N 0.000 claims description 2
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- CMANRZWLVWEYKY-UHFFFAOYSA-N 2-ethyl-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C=12C=CC=CC2=NC(CC)=NC=1N(C)C1=CC=C(OC)C=C1 CMANRZWLVWEYKY-UHFFFAOYSA-N 0.000 claims description 2
- NZPYZRZUALMAPI-UHFFFAOYSA-N 2-methoxy-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(OC)=NC2=CC=CC=C12 NZPYZRZUALMAPI-UHFFFAOYSA-N 0.000 claims description 2
- KNUASDCXIXUNJF-UHFFFAOYSA-N 2-n-(3,7-dimethylocta-2,6-dienyl)-4-n-methyl-4-n-(4-methylphenyl)quinazoline-2,4-diamine Chemical compound N=1C(NCC=C(C)CCC=C(C)C)=NC2=CC=CC=C2C=1N(C)C1=CC=C(C)C=C1 KNUASDCXIXUNJF-UHFFFAOYSA-N 0.000 claims description 2
- BFBNRDWKLSSZRF-UHFFFAOYSA-N 2-n-[2-(1h-imidazol-5-yl)ethyl]-4-n-(4-methoxyphenyl)-4-n-methylquinazoline-2,4-diamine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(NCCC=2N=CNC=2)=NC2=CC=CC=C12 BFBNRDWKLSSZRF-UHFFFAOYSA-N 0.000 claims description 2
- DQYRGKUJQJNOPX-UHFFFAOYSA-N 2-n-[3-(dimethylamino)propyl]-4-n-(4-methoxyphenyl)-4-n-methylquinazoline-2,4-diamine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(NCCCN(C)C)=NC2=CC=CC=C12 DQYRGKUJQJNOPX-UHFFFAOYSA-N 0.000 claims description 2
- AUIIPISVOIPEAT-UHFFFAOYSA-N 4-[(2-chloroquinazolin-4-yl)-methylamino]phenol Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1N(C)C1=CC=C(O)C=C1 AUIIPISVOIPEAT-UHFFFAOYSA-N 0.000 claims description 2
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Images
Classifications
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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US20080032974A1 (en) * | 2003-07-03 | 2008-02-07 | Myriad Genetics, Incorporated | Compounds and therapeutical use thereof |
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US20170050937A1 (en) | 2017-02-23 |
CN1984660A (zh) | 2007-06-20 |
AU2004253967A1 (en) | 2005-01-13 |
EP1660092A2 (en) | 2006-05-31 |
AU2004253967B2 (en) | 2010-02-18 |
JP2007524637A (ja) | 2007-08-30 |
JP2012207044A (ja) | 2012-10-25 |
JP5129957B2 (ja) | 2013-01-30 |
US20080032974A1 (en) | 2008-02-07 |
NZ544472A (en) | 2009-04-30 |
AU2004253967A8 (en) | 2010-02-04 |
US20070249601A1 (en) | 2007-10-25 |
CA2531327A1 (en) | 2005-01-13 |
US20080039479A1 (en) | 2008-02-14 |
WO2005003100A3 (en) | 2005-05-12 |
KR101218213B1 (ko) | 2013-01-04 |
US20050137213A1 (en) | 2005-06-23 |
US7618975B2 (en) | 2009-11-17 |
US20070208044A1 (en) | 2007-09-06 |
CN1984660B (zh) | 2010-12-15 |
WO2005003100A2 (en) | 2005-01-13 |
KR20060052775A (ko) | 2006-05-19 |
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