TW200524903A - Quinazoline derivatives - Google Patents
Quinazoline derivatives Download PDFInfo
- Publication number
- TW200524903A TW200524903A TW093134778A TW93134778A TW200524903A TW 200524903 A TW200524903 A TW 200524903A TW 093134778 A TW093134778 A TW 093134778A TW 93134778 A TW93134778 A TW 93134778A TW 200524903 A TW200524903 A TW 200524903A
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- oxy
- group
- amino
- phenyl
- Prior art date
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- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title claims abstract description 18
- 125000001424 substituent group Chemical group 0.000 claims abstract description 361
- 230000000694 effects Effects 0.000 claims abstract description 14
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 13
- 241001465754 Metazoa Species 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims abstract 3
- 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 1149
- -1 trifluorofluorenyl Chemical group 0.000 claims description 711
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 426
- 239000001257 hydrogen Substances 0.000 claims description 301
- 229910052739 hydrogen Inorganic materials 0.000 claims description 301
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 286
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 283
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 226
- 229910052757 nitrogen Inorganic materials 0.000 claims description 220
- 125000003545 alkoxy group Chemical group 0.000 claims description 217
- 125000000623 heterocyclic group Chemical group 0.000 claims description 208
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 198
- 125000003282 alkyl amino group Chemical group 0.000 claims description 180
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 160
- 125000003342 alkenyl group Chemical group 0.000 claims description 154
- 125000000304 alkynyl group Chemical group 0.000 claims description 150
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 137
- 125000005843 halogen group Chemical group 0.000 claims description 133
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 120
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 109
- 150000001412 amines Chemical class 0.000 claims description 106
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 103
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 94
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 89
- 150000001875 compounds Chemical class 0.000 claims description 75
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 67
- 229910052799 carbon Inorganic materials 0.000 claims description 58
- 125000004414 alkyl thio group Chemical group 0.000 claims description 55
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 53
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 48
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 48
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 42
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 41
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 40
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 39
- 125000003277 amino group Chemical group 0.000 claims description 38
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 37
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 36
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 35
- 125000000468 ketone group Chemical group 0.000 claims description 31
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 31
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 30
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 239000001301 oxygen Substances 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 24
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000011593 sulfur Substances 0.000 claims description 24
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 23
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 23
- 229930194542 Keto Natural products 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 17
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 14
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 13
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 12
- 102000027426 receptor tyrosine kinases Human genes 0.000 claims description 12
- 108091008598 receptor tyrosine kinases Proteins 0.000 claims description 12
- ROPLCSFPUPWHGJ-UHFFFAOYSA-N hydroxycyanamide Chemical compound ONC#N ROPLCSFPUPWHGJ-UHFFFAOYSA-N 0.000 claims description 11
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 10
- 150000003973 alkyl amines Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 6
- 241000283074 Equus asinus Species 0.000 claims description 6
- 229910052786 argon Inorganic materials 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 5
- 150000002918 oxazolines Chemical class 0.000 claims description 5
- WFAFGNCZWMJZCK-UHFFFAOYSA-N 2-hydroxy-n-methylacetamide Chemical compound CNC(=O)CO WFAFGNCZWMJZCK-UHFFFAOYSA-N 0.000 claims description 4
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 3
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 3
- MAQAGRJURDEYDQ-UHFFFAOYSA-N 6-methylpyridine Chemical compound CC1=C=CC=C[N]1 MAQAGRJURDEYDQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 150000001924 cycloalkanes Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 claims description 3
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims description 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 241001529936 Murinae Species 0.000 claims description 2
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 claims description 2
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 2
- 125000005323 thioketone group Chemical group 0.000 claims description 2
- 150000003246 quinazolines Chemical class 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 241000282412 Homo Species 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 239000004575 stone Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- DTACPUNZACSGAZ-UHFFFAOYSA-N 1-(hydroxymethyl)cyclopropane-1-carboxamide Chemical compound NC(=O)C1(CO)CC1 DTACPUNZACSGAZ-UHFFFAOYSA-N 0.000 claims 1
- GGYRVEUCCUJDFK-UHFFFAOYSA-N 1-ethyl-1,3-dimethylurea Chemical compound CCN(C)C(=O)NC GGYRVEUCCUJDFK-UHFFFAOYSA-N 0.000 claims 1
- UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
- AUCGNAJVFOZTHS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=C=N[CH]1 AUCGNAJVFOZTHS-UHFFFAOYSA-N 0.000 claims 1
- CGWMMQFGQVDRII-UHFFFAOYSA-N 4-(pyridin-2-ylmethoxy)aniline Chemical compound C1=CC(N)=CC=C1OCC1=CC=CC=N1 CGWMMQFGQVDRII-UHFFFAOYSA-N 0.000 claims 1
- QALCERQMPHVCPK-UHFFFAOYSA-N C(C)C1=C(C=2CC3=CC=CC=C3C2C=C1)N Chemical compound C(C)C1=C(C=2CC3=CC=CC=C3C2C=C1)N QALCERQMPHVCPK-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 1
- 229920000877 Melamine resin Polymers 0.000 claims 1
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 claims 1
- 229930182474 N-glycoside Natural products 0.000 claims 1
- 208000008765 Sciatica Diseases 0.000 claims 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims 1
- 101100041681 Takifugu rubripes sand gene Proteins 0.000 claims 1
- QRCJVAADFAROKA-UHFFFAOYSA-N amino 2-aminoacetate Chemical compound NCC(=O)ON QRCJVAADFAROKA-UHFFFAOYSA-N 0.000 claims 1
- RSDOASZYYCOXIB-UHFFFAOYSA-N beta-alaninamide Chemical compound NCCC(N)=O RSDOASZYYCOXIB-UHFFFAOYSA-N 0.000 claims 1
- ITQTTZVARXURQS-UHFFFAOYSA-N beta-methylpyridine Natural products CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims 1
- IQNWBWZINFOHGE-UHFFFAOYSA-N bucharamine Natural products CC1OC=2NC3=CC=CC=C3C(=O)C=2C1(C)CCC1OC(C)(C)OC1(C)C IQNWBWZINFOHGE-UHFFFAOYSA-N 0.000 claims 1
- ICSJNYPTNPRPNC-UHFFFAOYSA-N butan-1-amine heptane Chemical compound CCCCCCC.CCCCN ICSJNYPTNPRPNC-UHFFFAOYSA-N 0.000 claims 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 210000000078 claw Anatomy 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- VXAWCKIQYKXJMD-UHFFFAOYSA-N ethynamine Chemical compound NC#C VXAWCKIQYKXJMD-UHFFFAOYSA-N 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims 1
- BUIMWOLDCCGZKZ-UHFFFAOYSA-N n-hydroxynitramide Chemical compound ON[N+]([O-])=O BUIMWOLDCCGZKZ-UHFFFAOYSA-N 0.000 claims 1
- MKDUUUBNJFUNJR-UHFFFAOYSA-N n-methyloxolane-2-carboxamide Chemical compound CNC(=O)C1CCCO1 MKDUUUBNJFUNJR-UHFFFAOYSA-N 0.000 claims 1
- GNFWGDKKNWGGJY-UHFFFAOYSA-N propanimidamide Chemical compound CCC(N)=N GNFWGDKKNWGGJY-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000004576 sand Substances 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 239000011669 selenium Substances 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 abstract description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 188
- 125000001153 fluoro group Chemical group F* 0.000 description 56
- 150000001721 carbon Chemical group 0.000 description 46
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 35
- 239000007789 gas Substances 0.000 description 26
- 206010028980 Neoplasm Diseases 0.000 description 24
- 239000002585 base Substances 0.000 description 24
- 201000011510 cancer Diseases 0.000 description 16
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 15
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 14
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 13
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 12
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 11
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 10
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- 108020001305 NR1 subfamily Proteins 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 8
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 8
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 8
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 7
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 7
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 7
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 125000002757 morpholinyl group Chemical group 0.000 description 7
- 102000005962 receptors Human genes 0.000 description 7
- 108020003175 receptors Proteins 0.000 description 7
- 125000005942 tetrahydropyridyl group Chemical group 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 6
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 6
- 108060006698 EGF receptor Proteins 0.000 description 6
- 102000001301 EGF receptor Human genes 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 6
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
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- C—CHEMISTRY; METALLURGY
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- C07D401/14—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 containing three or more hetero rings
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P13/00—Drugs for disorders of the urinary system
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Applications Claiming Priority (1)
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| GBGB0326459.5A GB0326459D0 (en) | 2003-11-13 | 2003-11-13 | Quinazoline derivatives |
Publications (1)
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| TW200524903A true TW200524903A (en) | 2005-08-01 |
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| JP2005515176A (ja) * | 2001-11-03 | 2005-05-26 | アストラゼネカ アクチボラグ | 抗腫瘍剤としてのキナゾリン誘導体 |
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| AU2004272345A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| ES2305844T3 (es) * | 2003-09-16 | 2008-11-01 | Astrazeneca Ab | Derivados de quinazolina como inhibidores de tirosina cinasa. |
| US20070032508A1 (en) * | 2003-09-16 | 2007-02-08 | Bradbury Robert H | Quinazoline derivatives as tyrosine kinase inhibitors |
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| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| JP5032851B2 (ja) | 2004-02-03 | 2012-09-26 | アストラゼネカ アクチボラグ | キナゾリン誘導体 |
| AU2005250224A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as ERBB receptor tyrosine kinases |
| EP1838712B8 (en) * | 2004-12-14 | 2011-10-12 | AstraZeneca AB | Pyrazolopyrimidine compounds as antitumor agents |
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| GB0508715D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| JP2009508917A (ja) * | 2005-09-20 | 2009-03-05 | アストラゼネカ アクチボラグ | 抗癌剤としてのキナゾリン誘導体 |
| WO2007034144A1 (en) * | 2005-09-20 | 2007-03-29 | Astrazeneca Ab | 4- (ih-indazol-s-yl-amino)-quinazoline compounds as erbb receptor tyrosine kinase inhibitors for the treatment of cancer |
| JP2009517450A (ja) * | 2005-12-02 | 2009-04-30 | アストラゼネカ アクチボラグ | チロシンキナーゼ阻害薬としての４−アニリノ置換キナゾリン誘導体 |
| JP2009517451A (ja) * | 2005-12-02 | 2009-04-30 | アストラゼネカ アクチボラグ | Ｅｒｂｂチロシンキナーゼの阻害剤として使用されるキナゾリン誘導体 |
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-
2003
- 2003-11-13 GB GBGB0326459.5A patent/GB0326459D0/en not_active Ceased
-
2004
- 2004-11-11 CN CNA2004800404156A patent/CN1906178A/zh active Pending
- 2004-11-11 KR KR1020067011553A patent/KR20060127410A/ko not_active Withdrawn
- 2004-11-11 UY UY28610A patent/UY28610A1/es not_active Application Discontinuation
- 2004-11-11 US US10/578,663 patent/US7625908B2/en not_active Expired - Fee Related
- 2004-11-11 BR BRPI0416479-2A patent/BRPI0416479A/pt not_active Application Discontinuation
- 2004-11-11 CA CA002545262A patent/CA2545262A1/en not_active Abandoned
- 2004-11-11 AU AU2004293250A patent/AU2004293250A1/en not_active Abandoned
- 2004-11-11 CN CN201010119887A patent/CN101787019A/zh active Pending
- 2004-11-11 JP JP2006538946A patent/JP2007511491A/ja active Pending
- 2004-11-11 WO PCT/GB2004/004761 patent/WO2005051923A1/en not_active Ceased
- 2004-11-11 EP EP04798484A patent/EP1685116A1/en not_active Withdrawn
- 2004-11-12 AR ARP040104181A patent/AR046452A1/es unknown
- 2004-11-12 TW TW093134778A patent/TW200524903A/zh unknown
-
2006
- 2006-05-04 IL IL175421A patent/IL175421A0/en unknown
- 2006-05-12 ZA ZA200603817A patent/ZA200603817B/en unknown
- 2006-05-23 NO NO20062353A patent/NO20062353L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AR046452A1 (es) | 2005-12-07 |
| CN101787019A (zh) | 2010-07-28 |
| AU2004293250A1 (en) | 2005-06-09 |
| GB0326459D0 (en) | 2003-12-17 |
| BRPI0416479A (pt) | 2007-03-06 |
| EP1685116A1 (en) | 2006-08-02 |
| NO20062353L (no) | 2006-08-09 |
| CA2545262A1 (en) | 2005-06-09 |
| KR20060127410A (ko) | 2006-12-12 |
| WO2005051923A1 (en) | 2005-06-09 |
| JP2007511491A (ja) | 2007-05-10 |
| CN1906178A (zh) | 2007-01-31 |
| US7625908B2 (en) | 2009-12-01 |
| ZA200603817B (en) | 2007-10-31 |
| US20070244136A1 (en) | 2007-10-18 |
| UY28610A1 (es) | 2005-06-30 |
| IL175421A0 (en) | 2006-09-05 |
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