JP2007511491A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2007511491A5 JP2007511491A5 JP2006538946A JP2006538946A JP2007511491A5 JP 2007511491 A5 JP2007511491 A5 JP 2007511491A5 JP 2006538946 A JP2006538946 A JP 2006538946A JP 2006538946 A JP2006538946 A JP 2006538946A JP 2007511491 A5 JP2007511491 A5 JP 2007511491A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- oxy
- amino
- quinazolin
- phenyl
- 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.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 claims 209
- 229910052757 nitrogen Inorganic materials 0.000 claims 44
- 239000001257 hydrogen Substances 0.000 claims 41
- 229910052739 hydrogen Inorganic materials 0.000 claims 41
- -1 cyano, nitro, hydroxy, amino, carboxy, carbamoyl Chemical group 0.000 claims 36
- 125000001424 substituent group Chemical group 0.000 claims 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 34
- 125000003545 alkoxy group Chemical group 0.000 claims 33
- 125000000623 heterocyclic group Chemical group 0.000 claims 31
- 125000003282 alkyl amino group Chemical group 0.000 claims 29
- 125000005843 halogen group Chemical group 0.000 claims 29
- 150000003246 quinazolines Chemical class 0.000 claims 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 24
- 125000003342 alkenyl group Chemical group 0.000 claims 23
- 125000000304 alkynyl group Chemical group 0.000 claims 23
- 229910052760 oxygen Inorganic materials 0.000 claims 23
- 125000001589 carboacyl group Chemical group 0.000 claims 17
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 16
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 15
- 125000005236 alkanoylamino group Chemical group 0.000 claims 14
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 14
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 12
- 125000004414 alkyl thio group Chemical group 0.000 claims 12
- 125000000524 functional group Chemical group 0.000 claims 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 10
- 125000004423 acyloxy group Chemical group 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 7
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- 125000006319 alkynyl amino group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 241001465754 Metazoa Species 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 4
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims 3
- 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims 3
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 230000000717 retained effect Effects 0.000 claims 3
- 241000282412 Homo Species 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 238000003780 insertion Methods 0.000 claims 2
- 230000037431 insertion Effects 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- RGCXZBHFAMZESU-FOIQADDNSA-N (2r)-n-[(2r)-1-[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]-2,4-dihydroxybutanamide Chemical compound C=12C(OC[C@@H](C)NC(=O)[C@H](O)CCO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CSC=N1 RGCXZBHFAMZESU-FOIQADDNSA-N 0.000 claims 1
- HEHLJJFIAJUQJF-VGOFRKELSA-N (2r)-n-[(2r)-1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]-2,4-dihydroxybutanamide Chemical compound C=12C(OC[C@@H](C)NC(=O)[C@H](O)CCO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 HEHLJJFIAJUQJF-VGOFRKELSA-N 0.000 claims 1
- MXIIFZGCKAYGMJ-VGOFRKELSA-N (2r)-n-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2,4-dihydroxybutanamide Chemical compound C=12C(O[C@@H](CNC(=O)[C@H](O)CCO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 MXIIFZGCKAYGMJ-VGOFRKELSA-N 0.000 claims 1
- DCFPQVBAWLOOHB-QZTJIDSGSA-N (2r)-n-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-hydroxy-n-methylpropanamide Chemical compound C=12C(O[C@@H](CN(C)C(=O)[C@@H](C)O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 DCFPQVBAWLOOHB-QZTJIDSGSA-N 0.000 claims 1
- KHYSEXYNSLDULJ-RTBURBONSA-N (2r)-n-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-methoxy-n-methylpropanamide Chemical compound C=12C(O[C@H](C)CN(C)C(=O)[C@@H](C)OC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 KHYSEXYNSLDULJ-RTBURBONSA-N 0.000 claims 1
- MXIIFZGCKAYGMJ-HTAPYJJXSA-N (2r)-n-[(2s)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2,4-dihydroxybutanamide Chemical compound C=12C(O[C@H](CNC(=O)[C@H](O)CCO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 MXIIFZGCKAYGMJ-HTAPYJJXSA-N 0.000 claims 1
- KDLYFRZQLPIQAE-LJQANCHMSA-N (2r)-n-[2-[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2,4-dihydroxybutanamide Chemical compound C=12C(OCCNC(=O)[C@H](O)CCO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CSC=N1 KDLYFRZQLPIQAE-LJQANCHMSA-N 0.000 claims 1
- BVOFMXJMDDDZLZ-OAQYLSRUSA-N (2r)-n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2,4-dihydroxybutanamide Chemical compound C=12C(OCCNC(=O)[C@H](O)CCO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 BVOFMXJMDDDZLZ-OAQYLSRUSA-N 0.000 claims 1
- RGCXZBHFAMZESU-QRWLVFNGSA-N (2s)-n-[(2r)-1-[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]-2,4-dihydroxybutanamide Chemical compound C=12C(OC[C@@H](C)NC(=O)[C@@H](O)CCO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CSC=N1 RGCXZBHFAMZESU-QRWLVFNGSA-N 0.000 claims 1
- HEHLJJFIAJUQJF-VGSWGCGISA-N (2s)-n-[(2r)-1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]-2,4-dihydroxybutanamide Chemical compound C=12C(OC[C@@H](C)NC(=O)[C@@H](O)CCO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 HEHLJJFIAJUQJF-VGSWGCGISA-N 0.000 claims 1
- MXIIFZGCKAYGMJ-VGSWGCGISA-N (2s)-n-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2,4-dihydroxybutanamide Chemical compound C=12C(O[C@@H](CNC(=O)[C@@H](O)CCO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 MXIIFZGCKAYGMJ-VGSWGCGISA-N 0.000 claims 1
- DCFPQVBAWLOOHB-MSOLQXFVSA-N (2s)-n-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-hydroxy-n-methylpropanamide Chemical compound C=12C(O[C@@H](CN(C)C(=O)[C@H](C)O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 DCFPQVBAWLOOHB-MSOLQXFVSA-N 0.000 claims 1
- MXIIFZGCKAYGMJ-JTSKRJEESA-N (2s)-n-[(2s)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2,4-dihydroxybutanamide Chemical compound C=12C(O[C@H](CNC(=O)[C@@H](O)CCO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 MXIIFZGCKAYGMJ-JTSKRJEESA-N 0.000 claims 1
- KDLYFRZQLPIQAE-IBGZPJMESA-N (2s)-n-[2-[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2,4-dihydroxybutanamide Chemical compound C=12C(OCCNC(=O)[C@@H](O)CCO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CSC=N1 KDLYFRZQLPIQAE-IBGZPJMESA-N 0.000 claims 1
- BVOFMXJMDDDZLZ-NRFANRHFSA-N (2s)-n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2,4-dihydroxybutanamide Chemical compound C=12C(OCCNC(=O)[C@@H](O)CCO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 BVOFMXJMDDDZLZ-NRFANRHFSA-N 0.000 claims 1
- ZAKHJBQWEPRKMT-DEOSSOPVSA-N (2s)-n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n,1-dimethylpyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(CCC1)C)N(C)CCOC(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZAKHJBQWEPRKMT-DEOSSOPVSA-N 0.000 claims 1
- LXZRLYUXFGAGIQ-LJQANCHMSA-N 1-(2-chloroethyl)-3-[(2r)-2-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxypropyl]urea Chemical compound C=12C(O[C@@H](CNC(=O)NCCCl)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OC1=CC=C(C)N=C1 LXZRLYUXFGAGIQ-LJQANCHMSA-N 0.000 claims 1
- SLROYYWSTBZQMZ-MRXNPFEDSA-N 1-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-3-methylurea Chemical compound C=12C(O[C@H](C)CNC(=O)NC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 SLROYYWSTBZQMZ-MRXNPFEDSA-N 0.000 claims 1
- PPQZIYWBHSZTNJ-UHFFFAOYSA-N 1-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-1,3-dimethylurea Chemical compound C=12C(OCCN(C)C(=O)NC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 PPQZIYWBHSZTNJ-UHFFFAOYSA-N 0.000 claims 1
- RNARKSNZTYMXBL-OAQYLSRUSA-N 2-(dimethylamino)-n-methyl-n-[(2r)-2-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxypropyl]acetamide Chemical compound C=12C(O[C@@H](CN(C)C(=O)CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OC1=CC=C(C)N=C1 RNARKSNZTYMXBL-OAQYLSRUSA-N 0.000 claims 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 claims 1
- GELVZYOEQVJIRR-UHFFFAOYSA-N 2-chloropyrazine Chemical compound ClC1=CN=CC=N1 GELVZYOEQVJIRR-UHFFFAOYSA-N 0.000 claims 1
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 claims 1
- LAZJTIJBMKKFIG-MRXNPFEDSA-N 2-hydroxy-n-[(2r)-2-[4-[3-methyl-4-(1,3-thiazol-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]acetamide Chemical compound C=12C(O[C@@H](CNC(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=NC=CS1 LAZJTIJBMKKFIG-MRXNPFEDSA-N 0.000 claims 1
- LOQHCZCYQABYHY-MRXNPFEDSA-N 2-hydroxy-n-[(2r)-2-[4-[3-methyl-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]acetamide Chemical compound C=12C(O[C@@H](CNC(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CSC=N1 LOQHCZCYQABYHY-MRXNPFEDSA-N 0.000 claims 1
- NXMYXUOGTQTXPD-GOSISDBHSA-N 2-hydroxy-n-[(2r)-2-[4-[3-methyl-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]acetamide Chemical compound C=12C(O[C@@H](CNC(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CC=CC=N1 NXMYXUOGTQTXPD-GOSISDBHSA-N 0.000 claims 1
- XMTAOKNQELBQQG-UHFFFAOYSA-N 2-hydroxy-n-[2-[4-[3-methyl-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]acetamide Chemical compound CC1=CC(NC=2C3=C(OCCNC(=O)CO)C=CC=C3N=CN=2)=CC=C1OCC1=CSC=N1 XMTAOKNQELBQQG-UHFFFAOYSA-N 0.000 claims 1
- OKOSXXHGHXQABS-UHFFFAOYSA-N 2-hydroxy-n-[2-[4-[3-methyl-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]acetamide Chemical compound CC1=CC(NC=2C3=C(OCCNC(=O)CO)C=CC=C3N=CN=2)=CC=C1OCC1=CC=CC=N1 OKOSXXHGHXQABS-UHFFFAOYSA-N 0.000 claims 1
- XAHDKVKSMZKHIC-LJQANCHMSA-N 2-hydroxy-n-methyl-n-[(2r)-1-[4-[3-methyl-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]acetamide Chemical compound C=12C(OC[C@@H](C)N(C)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CC=CC=N1 XAHDKVKSMZKHIC-LJQANCHMSA-N 0.000 claims 1
- QWPAWVKMLOZWHJ-QGZVFWFLSA-N 2-hydroxy-n-methyl-n-[(2r)-2-[4-[3-methyl-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]acetamide Chemical compound C=12C(O[C@@H](CN(C)C(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CSC=N1 QWPAWVKMLOZWHJ-QGZVFWFLSA-N 0.000 claims 1
- UHGZMNWLNKYLEM-LJQANCHMSA-N 2-hydroxy-n-methyl-n-[(2r)-2-[4-[3-methyl-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]acetamide Chemical compound C=12C(O[C@@H](CN(C)C(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CC=CC=N1 UHGZMNWLNKYLEM-LJQANCHMSA-N 0.000 claims 1
- HQCWDKGPBCFIPP-UHFFFAOYSA-N 2-hydroxy-n-methyl-n-[2-[4-[3-methyl-4-(1,3-thiazol-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]acetamide Chemical compound C=12C(OCCN(C)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=NC=CS1 HQCWDKGPBCFIPP-UHFFFAOYSA-N 0.000 claims 1
- WBTPOXTZBXHARX-UHFFFAOYSA-N 2-hydroxy-n-methyl-n-[2-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxyethyl]acetamide Chemical compound C=12C(OCCN(C)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OC1=CC=C(C)N=C1 WBTPOXTZBXHARX-UHFFFAOYSA-N 0.000 claims 1
- OKEMIUZADYEQMK-UHFFFAOYSA-N 2-hydroxy-n-methyl-n-[2-[4-[3-methyl-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]acetamide Chemical compound C=12C(OCCN(C)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CC=CC=N1 OKEMIUZADYEQMK-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- BUHXXCSXLSTUMT-UHFFFAOYSA-N 3-(2-chloroethyl)-1-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-1-methylurea Chemical compound C=12C(OCCN(C)C(=O)NCCCl)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 BUHXXCSXLSTUMT-UHFFFAOYSA-N 0.000 claims 1
- IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical compound ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 claims 1
- FWIBCWKHNZBDLS-UHFFFAOYSA-N 3-hydroxyoxolan-2-one Chemical compound OC1CCOC1=O FWIBCWKHNZBDLS-UHFFFAOYSA-N 0.000 claims 1
- BSDGZUDFPKIYQG-UHFFFAOYSA-N 4-bromopyridine Chemical compound BrC1=CC=NC=C1 BSDGZUDFPKIYQG-UHFFFAOYSA-N 0.000 claims 1
- DBPKMSBWOKAKLA-UHFFFAOYSA-N 4-chloropyrimidine Chemical compound ClC1=CC=NC=N1 DBPKMSBWOKAKLA-UHFFFAOYSA-N 0.000 claims 1
- XJXBWJFUCWOLSY-UHFFFAOYSA-N 4-methoxybutanamide Chemical compound COCCCC(N)=O XJXBWJFUCWOLSY-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- PVCJKHHOXFKFRP-UHFFFAOYSA-N N-acetylethanolamine Chemical compound CC(=O)NCCO PVCJKHHOXFKFRP-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 108010077895 Sarcosine Proteins 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- AIEKDGKAUXUAIY-UHFFFAOYSA-N methyl n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-methylcarbamate Chemical compound C=12C(OCCN(C)C(=O)OC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 AIEKDGKAUXUAIY-UHFFFAOYSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- WHTUWYBGTLLCKF-UHFFFAOYSA-N n-(1-methylpiperidin-4-yl)acetamide Chemical compound CN1CCC(NC(C)=O)CC1 WHTUWYBGTLLCKF-UHFFFAOYSA-N 0.000 claims 1
- ZQAVLJPAUJXLIX-OAHLLOKOSA-N n-[(2r)-1-[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(OC[C@@H](C)N(C)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CSC=N1 ZQAVLJPAUJXLIX-OAHLLOKOSA-N 0.000 claims 1
- HXMKNGQXLJHQDQ-QGZVFWFLSA-N n-[(2r)-1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(OC[C@@H](C)N(C)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 HXMKNGQXLJHQDQ-QGZVFWFLSA-N 0.000 claims 1
- HUPIUFKYLJGBQZ-MRXNPFEDSA-N n-[(2r)-1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]-2-hydroxyacetamide Chemical compound C=12C(OC[C@@H](C)NC(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 HUPIUFKYLJGBQZ-MRXNPFEDSA-N 0.000 claims 1
- AGYXOEHPGSPADW-QGZVFWFLSA-N n-[(2r)-1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]-n-methylacetamide Chemical compound C=12C(OC[C@@H](C)N(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 AGYXOEHPGSPADW-QGZVFWFLSA-N 0.000 claims 1
- PWDLHTPWJPPZSA-MRXNPFEDSA-N n-[(2r)-1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]acetamide Chemical compound C=12C(OC[C@@H](C)NC(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 PWDLHTPWJPPZSA-MRXNPFEDSA-N 0.000 claims 1
- DGSKZHBSFZOQCC-OAHLLOKOSA-N n-[(2r)-2-[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(O[C@@H](CN(C)C(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CSC=N1 DGSKZHBSFZOQCC-OAHLLOKOSA-N 0.000 claims 1
- HIJKEFXVZQXBBH-OAHLLOKOSA-N n-[(2r)-2-[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-n-methylacetamide Chemical compound C=12C(O[C@@H](CN(C)C(C)=O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CSC=N1 HIJKEFXVZQXBBH-OAHLLOKOSA-N 0.000 claims 1
- RJGUEINBMBKAHW-MRXNPFEDSA-N n-[(2r)-2-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(O[C@@H](CN(C)C(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CN=CC=N1 RJGUEINBMBKAHW-MRXNPFEDSA-N 0.000 claims 1
- QQENGEBJOGRZGM-MRXNPFEDSA-N n-[(2r)-2-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-n-methylacetamide Chemical compound C=12C(O[C@@H](CN(C)C(C)=O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CN=CC=N1 QQENGEBJOGRZGM-MRXNPFEDSA-N 0.000 claims 1
- XSWZZYSGFZGDPN-GOSISDBHSA-N n-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-1-hydroxy-n-methylcyclopropane-1-carboxamide Chemical compound C([C@@H](C)OC=1C2=C(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)N=CN=C2C=CC=1)N(C)C(=O)C1(O)CC1 XSWZZYSGFZGDPN-GOSISDBHSA-N 0.000 claims 1
- UCHICPZBKIPNQF-GOSISDBHSA-N n-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-(dimethylamino)acetamide Chemical compound C=12C(O[C@@H](CNC(=O)CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 UCHICPZBKIPNQF-GOSISDBHSA-N 0.000 claims 1
- DMBSRBYUXSTDHY-GOSISDBHSA-N n-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-hydroxy-n,2-dimethylpropanamide Chemical compound C=12C(O[C@@H](CN(C)C(=O)C(C)(C)O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 DMBSRBYUXSTDHY-GOSISDBHSA-N 0.000 claims 1
- ZROBAJVGRYCCGH-QGZVFWFLSA-N n-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(O[C@@H](CN(C)C(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZROBAJVGRYCCGH-QGZVFWFLSA-N 0.000 claims 1
- SOUKIHHAXODFLZ-MRXNPFEDSA-N n-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-hydroxyacetamide Chemical compound C=12C(O[C@@H](CNC(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 SOUKIHHAXODFLZ-MRXNPFEDSA-N 0.000 claims 1
- OZAOAQFGHPXSLH-GOSISDBHSA-N n-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-methoxy-n-methylacetamide Chemical compound C=12C(O[C@H](C)CN(C)C(=O)COC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 OZAOAQFGHPXSLH-GOSISDBHSA-N 0.000 claims 1
- JNDLTSVLIBRWEJ-QGZVFWFLSA-N n-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-methoxyacetamide Chemical compound C=12C(O[C@H](C)CNC(=O)COC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 JNDLTSVLIBRWEJ-QGZVFWFLSA-N 0.000 claims 1
- RYSILEDIQWYQBS-MRXNPFEDSA-N n-[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]acetamide Chemical compound C=12C(O[C@@H](CNC(C)=O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 RYSILEDIQWYQBS-MRXNPFEDSA-N 0.000 claims 1
- ZUAGEVWCLRYTPM-QGZVFWFLSA-N n-[(2r)-2-[4-[3-chloro-4-[(2-fluorophenyl)methoxy]anilino]quinazolin-5-yl]oxypropyl]-n-methylacetamide Chemical compound C=12C(O[C@@H](CN(C)C(C)=O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=C1F ZUAGEVWCLRYTPM-QGZVFWFLSA-N 0.000 claims 1
- PUHDHLKJNXTNHR-QGZVFWFLSA-N n-[(2r)-2-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]quinazolin-5-yl]oxypropyl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(O[C@@H](CN(C)C(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 PUHDHLKJNXTNHR-QGZVFWFLSA-N 0.000 claims 1
- LXPPMOMDIWXDJD-QGZVFWFLSA-N n-[(2r)-2-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]quinazolin-5-yl]oxypropyl]-n-methylacetamide Chemical compound C=12C(O[C@@H](CN(C)C(C)=O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 LXPPMOMDIWXDJD-QGZVFWFLSA-N 0.000 claims 1
- PWVNTKDZBXUJEI-GOSISDBHSA-N n-[(2r)-2-[4-[3-chloro-4-[(6-methylpyridin-2-yl)methoxy]anilino]quinazolin-5-yl]oxypropyl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(O[C@@H](CN(C)C(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(C)=N1 PWVNTKDZBXUJEI-GOSISDBHSA-N 0.000 claims 1
- UXLZBZLBSUYMQQ-MRXNPFEDSA-N n-[(2r)-2-[4-[3-methyl-4-(1,3-thiazol-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]acetamide Chemical compound C=12C(O[C@@H](CNC(C)=O)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=NC=CS1 UXLZBZLBSUYMQQ-MRXNPFEDSA-N 0.000 claims 1
- BREFKBNSGOBECV-GOSISDBHSA-N n-[(2r)-2-[4-[3-methyl-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]acetamide Chemical compound C=12C(O[C@@H](CNC(C)=O)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CC=CC=N1 BREFKBNSGOBECV-GOSISDBHSA-N 0.000 claims 1
- YTYQMDKLJBIMGP-GOSISDBHSA-N n-[(2r)-2-[4-[4-[(3-fluorophenyl)methoxy]-3-methylanilino]quinazolin-5-yl]oxypropyl]-2-hydroxyacetamide Chemical compound C=12C(O[C@@H](CNC(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CC=CC(F)=C1 YTYQMDKLJBIMGP-GOSISDBHSA-N 0.000 claims 1
- DPUKBNDGIMAXGX-GOSISDBHSA-N n-[(2r)-2-[4-[4-[(3-fluorophenyl)methoxy]-3-methylanilino]quinazolin-5-yl]oxypropyl]acetamide Chemical compound C=12C(O[C@@H](CNC(C)=O)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CC=CC(F)=C1 DPUKBNDGIMAXGX-GOSISDBHSA-N 0.000 claims 1
- FJWGIJOYRNPIJY-SFHVURJKSA-N n-[(2s)-1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]-2-(dimethylamino)acetamide Chemical compound C=12C(OC[C@H](C)NC(=O)CN(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 FJWGIJOYRNPIJY-SFHVURJKSA-N 0.000 claims 1
- HXMKNGQXLJHQDQ-KRWDZBQOSA-N n-[(2s)-1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(OC[C@H](C)N(C)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 HXMKNGQXLJHQDQ-KRWDZBQOSA-N 0.000 claims 1
- HUPIUFKYLJGBQZ-INIZCTEOSA-N n-[(2s)-1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]-2-hydroxyacetamide Chemical compound C=12C(OC[C@H](C)NC(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 HUPIUFKYLJGBQZ-INIZCTEOSA-N 0.000 claims 1
- ZHUAQXNXTUPMRX-SFHVURJKSA-N n-[(2s)-1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]-2-methoxy-n-methylacetamide Chemical compound C=12C(OC[C@H](C)N(C)C(=O)COC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZHUAQXNXTUPMRX-SFHVURJKSA-N 0.000 claims 1
- AGYXOEHPGSPADW-KRWDZBQOSA-N n-[(2s)-1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]-n-methylacetamide Chemical compound C=12C(OC[C@H](C)N(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 AGYXOEHPGSPADW-KRWDZBQOSA-N 0.000 claims 1
- KJNQAOYUNWWUQV-IBGZPJMESA-N n-[(2s)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-(dimethylamino)-n-methylacetamide Chemical compound C=12C(O[C@H](CN(C)C(=O)CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 KJNQAOYUNWWUQV-IBGZPJMESA-N 0.000 claims 1
- UCHICPZBKIPNQF-SFHVURJKSA-N n-[(2s)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-(dimethylamino)acetamide Chemical compound C=12C(O[C@H](CNC(=O)CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 UCHICPZBKIPNQF-SFHVURJKSA-N 0.000 claims 1
- ZROBAJVGRYCCGH-KRWDZBQOSA-N n-[(2s)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(O[C@H](CN(C)C(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZROBAJVGRYCCGH-KRWDZBQOSA-N 0.000 claims 1
- SOUKIHHAXODFLZ-INIZCTEOSA-N n-[(2s)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-hydroxyacetamide Chemical compound C=12C(O[C@H](CNC(=O)CO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 SOUKIHHAXODFLZ-INIZCTEOSA-N 0.000 claims 1
- OZAOAQFGHPXSLH-SFHVURJKSA-N n-[(2s)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-methoxy-n-methylacetamide Chemical compound C=12C(O[C@@H](C)CN(C)C(=O)COC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 OZAOAQFGHPXSLH-SFHVURJKSA-N 0.000 claims 1
- JNDLTSVLIBRWEJ-KRWDZBQOSA-N n-[(2s)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-methoxyacetamide Chemical compound C=12C(O[C@@H](C)CNC(=O)COC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 JNDLTSVLIBRWEJ-KRWDZBQOSA-N 0.000 claims 1
- QGXPBIUVHIKJLS-KRWDZBQOSA-N n-[(2s)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-2-methylsulfonylacetamide Chemical compound C=12C(O[C@H](CNC(=O)CS(C)(=O)=O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 QGXPBIUVHIKJLS-KRWDZBQOSA-N 0.000 claims 1
- CUEYYCHCJJEJAN-SFHVURJKSA-N n-[(2s)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-n-methyl-2-methylsulfonylacetamide Chemical compound C=12C(O[C@H](CN(C)C(=O)CS(C)(=O)=O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 CUEYYCHCJJEJAN-SFHVURJKSA-N 0.000 claims 1
- RXQDSMRJTJVLCQ-KRWDZBQOSA-N n-[(2s)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]-n-methylacetamide Chemical compound C=12C(O[C@H](CN(C)C(C)=O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 RXQDSMRJTJVLCQ-KRWDZBQOSA-N 0.000 claims 1
- RYSILEDIQWYQBS-INIZCTEOSA-N n-[(2s)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]acetamide Chemical compound C=12C(O[C@H](CNC(C)=O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 RYSILEDIQWYQBS-INIZCTEOSA-N 0.000 claims 1
- MPMDFFAUHNUALY-UHFFFAOYSA-N n-[1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxy-2-methylpropan-2-yl]-2-hydroxyacetamide Chemical compound C=12C(OCC(C)(C)NC(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 MPMDFFAUHNUALY-UHFFFAOYSA-N 0.000 claims 1
- LLOUKDHTIFYVSS-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(OCCN(C)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CSC=N1 LLOUKDHTIFYVSS-UHFFFAOYSA-N 0.000 claims 1
- UKXKGMGOJVWGEL-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-methylacetamide Chemical compound C=12C(OCCN(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CSC=N1 UKXKGMGOJVWGEL-UHFFFAOYSA-N 0.000 claims 1
- CFGHMIDRBOFNGI-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(2-pyridin-2-ylpropan-2-yloxy)anilino]quinazolin-5-yl]oxyethyl]-n-methylacetamide Chemical compound C=12C(OCCN(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OC(C)(C)C1=CC=CC=N1 CFGHMIDRBOFNGI-UHFFFAOYSA-N 0.000 claims 1
- KZHJYRHBVZACQG-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(OCCN(C)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CN=CC=N1 KZHJYRHBVZACQG-UHFFFAOYSA-N 0.000 claims 1
- WSWZIBYAHQAIPV-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-methylacetamide Chemical compound C=12C(OCCN(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CN=CC=N1 WSWZIBYAHQAIPV-UHFFFAOYSA-N 0.000 claims 1
- VFKPIZMTBJHQTN-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-(dimethylamino)-n-methylacetamide Chemical compound C=12C(OCCN(C)C(=O)CN(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 VFKPIZMTBJHQTN-UHFFFAOYSA-N 0.000 claims 1
- XDBKQDAUHNUPBD-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-(dimethylamino)acetamide Chemical compound C=12C(OCCNC(=O)CN(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 XDBKQDAUHNUPBD-UHFFFAOYSA-N 0.000 claims 1
- FRAZOYGEZQRNHB-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-hydroxy-n,2-dimethylpropanamide Chemical compound C=12C(OCCN(C)C(=O)C(C)(C)O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 FRAZOYGEZQRNHB-UHFFFAOYSA-N 0.000 claims 1
- PUUUPENHIRMZFW-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-hydroxy-n-(oxan-4-yl)acetamide Chemical compound C1COCCC1N(C(=O)CO)CCOC(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 PUUUPENHIRMZFW-UHFFFAOYSA-N 0.000 claims 1
- XNMHWKJRXNZELF-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(OCCN(C)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 XNMHWKJRXNZELF-UHFFFAOYSA-N 0.000 claims 1
- OIJXQVZPGHVADM-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-hydroxy-n-methylpropanamide Chemical compound C=12C(OCCN(C)C(=O)C(O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 OIJXQVZPGHVADM-UHFFFAOYSA-N 0.000 claims 1
- DKCBXROCHYJLIU-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-hydroxy-n-prop-2-enylacetamide Chemical compound C=12C(OCCN(C(=O)CO)CC=C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 DKCBXROCHYJLIU-UHFFFAOYSA-N 0.000 claims 1
- FJRVTAFBUMIFKB-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-hydroxy-n-prop-2-ynylacetamide Chemical compound C=12C(OCCN(C(=O)CO)CC#C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 FJRVTAFBUMIFKB-UHFFFAOYSA-N 0.000 claims 1
- GSGZYALSWZZWAX-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-hydroxy-n-propan-2-ylacetamide Chemical compound C=12C(OCCN(C(C)C)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 GSGZYALSWZZWAX-UHFFFAOYSA-N 0.000 claims 1
- GZNPUHWWCKHCGY-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-hydroxy-n-propylacetamide Chemical compound C=12C(OCCN(CCC)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 GZNPUHWWCKHCGY-UHFFFAOYSA-N 0.000 claims 1
- HWTLPRQUZNJVLY-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-hydroxyacetamide Chemical compound C=12C(OCCNC(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 HWTLPRQUZNJVLY-UHFFFAOYSA-N 0.000 claims 1
- UXKITDCKQZKVQS-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-methoxy-n-methylacetamide Chemical compound C=12C(OCCN(C)C(=O)COC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 UXKITDCKQZKVQS-UHFFFAOYSA-N 0.000 claims 1
- WPVZQLCBCWRRPN-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-methoxyacetamide Chemical compound C=12C(OCCNC(=O)COC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 WPVZQLCBCWRRPN-UHFFFAOYSA-N 0.000 claims 1
- GRCKJPZWEMXYCG-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-2-methylsulfonylacetamide Chemical compound C=12C(OCCNC(=O)CS(=O)(=O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 GRCKJPZWEMXYCG-UHFFFAOYSA-N 0.000 claims 1
- IXSCLKPGPOGEFR-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-3-hydroxy-n,2,2-trimethylpropanamide Chemical compound C=12C(OCCN(C)C(=O)C(C)(C)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 IXSCLKPGPOGEFR-UHFFFAOYSA-N 0.000 claims 1
- UBPIGPJXMNPYNC-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-3-hydroxy-n-methylpropanamide Chemical compound C=12C(OCCN(C)C(=O)CCO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 UBPIGPJXMNPYNC-UHFFFAOYSA-N 0.000 claims 1
- DHTQPVZGPLQADO-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-(2-hydroxyethyl)acetamide Chemical compound C=12C(OCCN(CCO)C(=O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 DHTQPVZGPLQADO-UHFFFAOYSA-N 0.000 claims 1
- GKTJZGHYEBILAQ-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-(2-methoxyethyl)acetamide Chemical compound C=12C(OCCN(CCOC)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 GKTJZGHYEBILAQ-UHFFFAOYSA-N 0.000 claims 1
- NIVKUOGITMTJKK-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-(cyclopropylmethyl)-2-hydroxyacetamide Chemical compound C1CC1CN(C(=O)CO)CCOC(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 NIVKUOGITMTJKK-UHFFFAOYSA-N 0.000 claims 1
- WTSPBYNDQPIHDD-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-(cyclopropylmethyl)acetamide Chemical compound C1CC1CN(C(=O)C)CCOC(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 WTSPBYNDQPIHDD-UHFFFAOYSA-N 0.000 claims 1
- DHENUTXYVBCSTG-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-cyclobutyl-2-hydroxyacetamide Chemical compound C1CCC1N(C(=O)CO)CCOC(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 DHENUTXYVBCSTG-UHFFFAOYSA-N 0.000 claims 1
- BTZFEYUHUYLZSR-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-cyclobutylacetamide Chemical compound C1CCC1N(C(=O)C)CCOC(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 BTZFEYUHUYLZSR-UHFFFAOYSA-N 0.000 claims 1
- HONLRZUHJCHZQZ-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-cyclopropyl-2-hydroxyacetamide Chemical compound C1CC1N(C(=O)CO)CCOC(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 HONLRZUHJCHZQZ-UHFFFAOYSA-N 0.000 claims 1
- FPYGZHNVNMLEFN-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-cyclopropylacetamide Chemical compound C1CC1N(C(=O)C)CCOC(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 FPYGZHNVNMLEFN-UHFFFAOYSA-N 0.000 claims 1
- XEJWJLAMIHFDNK-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-ethyl-2-hydroxyacetamide Chemical compound C=12C(OCCN(CC)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 XEJWJLAMIHFDNK-UHFFFAOYSA-N 0.000 claims 1
- YTGKTNRRTHOCTO-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-ethylacetamide Chemical compound C=12C(OCCN(CC)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 YTGKTNRRTHOCTO-UHFFFAOYSA-N 0.000 claims 1
- JTGFZPCQUAOLLV-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-methylacetamide Chemical compound C=12C(OCCN(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 JTGFZPCQUAOLLV-UHFFFAOYSA-N 0.000 claims 1
- IHUJMKSCBVVKMU-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-prop-2-enylacetamide Chemical compound C=12C(OCCN(C(=O)C)CC=C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 IHUJMKSCBVVKMU-UHFFFAOYSA-N 0.000 claims 1
- RJQOGJQOSSLCEQ-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-propan-2-ylacetamide Chemical compound C=12C(OCCN(C(C)C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 RJQOGJQOSSLCEQ-UHFFFAOYSA-N 0.000 claims 1
- CEWGKGSZOCEUPU-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]-n-propylacetamide Chemical compound C=12C(OCCN(CCC)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 CEWGKGSZOCEUPU-UHFFFAOYSA-N 0.000 claims 1
- DSTNVOKBQLFPHS-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]acetamide Chemical compound C=12C(OCCNC(=O)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 DSTNVOKBQLFPHS-UHFFFAOYSA-N 0.000 claims 1
- VGPXNHKPZDMLEI-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-[(2-fluorophenyl)methoxy]anilino]quinazolin-5-yl]oxyethyl]-n-methylacetamide Chemical compound C=12C(OCCN(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=C1F VGPXNHKPZDMLEI-UHFFFAOYSA-N 0.000 claims 1
- LOQXEVBOHILKGE-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]quinazolin-5-yl]oxyethyl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(OCCN(C)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 LOQXEVBOHILKGE-UHFFFAOYSA-N 0.000 claims 1
- CCRNHWRDLLLZBJ-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]quinazolin-5-yl]oxyethyl]-n-methylacetamide Chemical compound C=12C(OCCN(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 CCRNHWRDLLLZBJ-UHFFFAOYSA-N 0.000 claims 1
- QGCYREVIGXSBDG-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-[(6-methylpyridin-2-yl)methoxy]anilino]quinazolin-5-yl]oxyethyl]-2-hydroxy-n-methylacetamide Chemical compound C=12C(OCCN(C)C(=O)CO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(C)=N1 QGCYREVIGXSBDG-UHFFFAOYSA-N 0.000 claims 1
- HRDPCSZWOAJDFY-UHFFFAOYSA-N n-[2-[4-[3-chloro-4-[(6-methylpyridin-2-yl)methoxy]anilino]quinazolin-5-yl]oxyethyl]-n-methylacetamide Chemical compound C=12C(OCCN(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(C)=N1 HRDPCSZWOAJDFY-UHFFFAOYSA-N 0.000 claims 1
- HNZMHDINTFCKSS-QGZVFWFLSA-N n-methyl-n-[(2r)-1-[4-[3-methyl-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]acetamide Chemical compound C=12C(OC[C@@H](C)N(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CSC=N1 HNZMHDINTFCKSS-QGZVFWFLSA-N 0.000 claims 1
- YCCNETVNVYJQRO-LJQANCHMSA-N n-methyl-n-[(2r)-1-[4-[3-methyl-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropan-2-yl]acetamide Chemical compound C=12C(OC[C@@H](C)N(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CC=CC=N1 YCCNETVNVYJQRO-LJQANCHMSA-N 0.000 claims 1
- GSFRFIQEAYUYSS-HSZRJFAPSA-N n-methyl-n-[(2r)-2-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxypropyl]-2-morpholin-4-ylacetamide Chemical compound C([C@@H](C)OC=1C2=C(NC=3C=C(C)C(OC=4C=NC(C)=CC=4)=CC=3)N=CN=C2C=CC=1)N(C)C(=O)CN1CCOCC1 GSFRFIQEAYUYSS-HSZRJFAPSA-N 0.000 claims 1
- ODVZIJRPVBRFNP-HSZRJFAPSA-N n-methyl-n-[(2r)-2-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxypropyl]-2-pyrrolidin-1-ylacetamide Chemical compound C([C@@H](C)OC=1C2=C(NC=3C=C(C)C(OC=4C=NC(C)=CC=4)=CC=3)N=CN=C2C=CC=1)N(C)C(=O)CN1CCCC1 ODVZIJRPVBRFNP-HSZRJFAPSA-N 0.000 claims 1
- QMRQRDSGRMYSFI-LJQANCHMSA-N n-methyl-n-[(2r)-2-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxypropyl]acetamide Chemical compound C=12C(O[C@@H](CN(C)C(C)=O)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OC1=CC=C(C)N=C1 QMRQRDSGRMYSFI-LJQANCHMSA-N 0.000 claims 1
- ODVZIJRPVBRFNP-QHCPKHFHSA-N n-methyl-n-[(2s)-2-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxypropyl]-2-pyrrolidin-1-ylacetamide Chemical compound C([C@H](C)OC=1C2=C(NC=3C=C(C)C(OC=4C=NC(C)=CC=4)=CC=3)N=CN=C2C=CC=1)N(C)C(=O)CN1CCCC1 ODVZIJRPVBRFNP-QHCPKHFHSA-N 0.000 claims 1
- QMRQRDSGRMYSFI-IBGZPJMESA-N n-methyl-n-[(2s)-2-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxypropyl]acetamide Chemical compound C=12C(O[C@H](CN(C)C(C)=O)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OC1=CC=C(C)N=C1 QMRQRDSGRMYSFI-IBGZPJMESA-N 0.000 claims 1
- DYCFYKSTSFRHGJ-UHFFFAOYSA-N n-methyl-n-[2-[4-[3-methyl-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]acetamide Chemical compound C=12C(OCCN(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CSC=N1 DYCFYKSTSFRHGJ-UHFFFAOYSA-N 0.000 claims 1
- UKYMZAJAADTHIE-UHFFFAOYSA-N n-methyl-n-[2-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxyethyl]acetamide Chemical compound C=12C(OCCN(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OC1=CC=C(C)N=C1 UKYMZAJAADTHIE-UHFFFAOYSA-N 0.000 claims 1
- SHLGTVQDWLNGNB-UHFFFAOYSA-N n-methyl-n-[2-[4-[3-methyl-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]acetamide Chemical compound C=12C(OCCN(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CC=CC=N1 SHLGTVQDWLNGNB-UHFFFAOYSA-N 0.000 claims 1
- YKMLPTJNBWECAT-UHFFFAOYSA-N n-methyl-n-[2-[4-[3-methyl-4-[(5-methyl-1,2-oxazol-3-yl)methoxy]anilino]quinazolin-5-yl]oxyethyl]acetamide Chemical compound C=12C(OCCN(C)C(C)=O)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC=1C=C(C)ON=1 YKMLPTJNBWECAT-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- UGMLMRFRDGWJSC-HXUWFJFHSA-N tert-butyl n-[2-[[(2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxypropyl]amino]-2-oxoethyl]-n-methylcarbamate Chemical compound C=12C(O[C@@H](CNC(=O)CN(C)C(=O)OC(C)(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 UGMLMRFRDGWJSC-HXUWFJFHSA-N 0.000 claims 1
- 0 C*CC(**)=CC=C(C=C*)N(*)C(C1=C(*C(*)(*)C(*)(*)N)C=C2)=NC=NC1=CC2(C)N Chemical compound C*CC(**)=CC=C(C=C*)N(*)C(C1=C(*C(*)(*)C(*)(*)N)C=C2)=NC=NC1=CC2(C)N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0326459.5A GB0326459D0 (en) | 2003-11-13 | 2003-11-13 | Quinazoline derivatives |
| PCT/GB2004/004761 WO2005051923A1 (en) | 2003-11-13 | 2004-11-11 | Quinazoline derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007511491A JP2007511491A (ja) | 2007-05-10 |
| JP2007511491A5 true JP2007511491A5 (https=) | 2007-09-27 |
Family
ID=29726464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006538946A Pending JP2007511491A (ja) | 2003-11-13 | 2004-11-11 | キナゾリン誘導体 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7625908B2 (https=) |
| EP (1) | EP1685116A1 (https=) |
| JP (1) | JP2007511491A (https=) |
| KR (1) | KR20060127410A (https=) |
| CN (2) | CN1906178A (https=) |
| AR (1) | AR046452A1 (https=) |
| AU (1) | AU2004293250A1 (https=) |
| BR (1) | BRPI0416479A (https=) |
| CA (1) | CA2545262A1 (https=) |
| GB (1) | GB0326459D0 (https=) |
| IL (1) | IL175421A0 (https=) |
| NO (1) | NO20062353L (https=) |
| TW (1) | TW200524903A (https=) |
| UY (1) | UY28610A1 (https=) |
| WO (1) | WO2005051923A1 (https=) |
| ZA (1) | ZA200603817B (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| 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 |
| GB0309009D0 (en) * | 2003-04-22 | 2003-05-28 | Astrazeneca Ab | Quinazoline derivatives |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| 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 |
| AU2004272346A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| 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 |
| GB0504474D0 (en) * | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| GB0508717D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| 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 |
| WO2008041118A2 (en) | 2006-10-04 | 2008-04-10 | Pfizer Products Inc. | Pyrido[4,3-d]pyrimidin-4(3h)-one derivatives as calcium receptor antagonists |
| WO2009057139A2 (en) | 2007-10-29 | 2009-05-07 | Natco Pharma Limited | Novel 4-(tetrazol-5-yl)-quinazoline derivatives as anti cancer agents |
| RU2016112013A (ru) * | 2013-09-19 | 2017-10-24 | Пьер Фабр Медикамент | Производные хиназолина и их применение в качестве ингибиторов днк-метилтрансферазы |
Family Cites Families (138)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5538325A (en) * | 1978-09-11 | 1980-03-17 | Sankyo Co Ltd | 4-anilinoquinazoline derivative and its preparation |
| US4335127A (en) * | 1979-01-08 | 1982-06-15 | Janssen Pharmaceutica, N.V. | Piperidinylalkyl quinazoline compounds, composition and method of use |
| GB2160201B (en) * | 1984-06-14 | 1988-05-11 | Wyeth John & Brother Ltd | Quinazoline and cinnoline derivatives |
| KR910006138B1 (ko) | 1986-09-30 | 1991-08-16 | 에자이 가부시끼가이샤 | 환상아민 유도체 |
| IL89029A (en) | 1988-01-29 | 1993-01-31 | Lilly Co Eli | Fungicidal quinoline and cinnoline derivatives, compositions containing them, and fungicidal methods of using them |
| US4921863A (en) * | 1988-02-17 | 1990-05-01 | Eisai Co., Ltd. | Cyclic amine derivatives |
| CA1340821C (en) * | 1988-10-06 | 1999-11-16 | Nobuyuki Fukazawa | Heterocyclic compounds and anticancer-drug reinforcing agents containing them as effective components |
| US5409930A (en) | 1991-05-10 | 1995-04-25 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5721237A (en) * | 1991-05-10 | 1998-02-24 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Protein tyrosine kinase aryl and heteroaryl quinazoline compounds having selective inhibition of HER-2 autophosphorylation properties |
| US5710158A (en) | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| NZ243082A (en) | 1991-06-28 | 1995-02-24 | Ici Plc | 4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof |
| US5187168A (en) | 1991-10-24 | 1993-02-16 | American Home Products Corporation | Substituted quinazolines as angiotensin II antagonists |
| AU661533B2 (en) | 1992-01-20 | 1995-07-27 | Astrazeneca Ab | Quinazoline derivatives |
| WO1993017682A1 (en) | 1992-03-04 | 1993-09-16 | Abbott Laboratories | Angiotensin ii receptor antagonists |
| GB9323290D0 (en) | 1992-12-10 | 1994-01-05 | Zeneca Ltd | Quinazoline derivatives |
| JPH083144A (ja) | 1994-06-21 | 1996-01-09 | Chugai Pharmaceut Co Ltd | キナゾリン及びキノリン誘導体 |
| GB9510757D0 (en) | 1994-09-19 | 1995-07-19 | Wellcome Found | Therapeuticaly active compounds |
| TW321649B (https=) | 1994-11-12 | 1997-12-01 | Zeneca Ltd | |
| GB2295387A (en) | 1994-11-23 | 1996-05-29 | Glaxo Inc | Quinazoline antagonists of alpha 1c adrenergic receptors |
| GB9424233D0 (en) | 1994-11-30 | 1995-01-18 | Zeneca Ltd | Quinazoline derivatives |
| MX9707453A (es) | 1995-03-30 | 1997-12-31 | Pfizer | Derivados de quinazolina. |
| WO1996033977A1 (en) | 1995-04-27 | 1996-10-31 | Zeneca Limited | Quinazoline derivatives |
| GB9508535D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivative |
| GB9508538D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| GB9508565D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quiazoline derivative |
| GB9508537D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| US5747498A (en) * | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| US6046206A (en) * | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having a precancerous lesions with amide quinazoline derivatives |
| GB9514265D0 (en) | 1995-07-13 | 1995-09-13 | Wellcome Found | Hetrocyclic compounds |
| JPH11512708A (ja) | 1995-09-11 | 1999-11-02 | オステオアルスリィティス サイエンシズ，インコーポレイテッド | 変形性関節炎を治療するためのプロテインチロシンキナーゼインヒビター |
| AR004010A1 (es) | 1995-10-11 | 1998-09-30 | Glaxo Group Ltd | Compuestos heterociclicos |
| GB9624482D0 (en) * | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| KR100517060B1 (ko) * | 1996-01-31 | 2006-05-25 | 코스모페름 베.파우 | 안정화된생물학적유효화합물로이루어지는조성물의사용 |
| US5760041A (en) | 1996-02-05 | 1998-06-02 | American Cyanamid Company | 4-aminoquinazoline EGFR Inhibitors |
| BR9707495A (pt) | 1996-02-13 | 1999-07-27 | Zeneca Ltd | Derivado de quinazolina processo para a preparação do mesmo composição farmacêutica e processo para a produç o de um efeito antiangiogênico e/ou de redução de permeabilidade vascular em um animal de sangue quente |
| GB9603095D0 (en) | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| GB9603097D0 (en) | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline compounds |
| HU228446B1 (en) | 1996-04-12 | 2013-03-28 | Warner Lambert Co | Kinazoline derivatives as irreversible inhibitors of protein-kinase, pharmaceutical compositions containing these compounds and use thereof |
| GB9607729D0 (en) | 1996-04-13 | 1996-06-19 | Zeneca Ltd | Quinazoline derivatives |
| ID19609A (id) | 1996-07-13 | 1998-07-23 | Glaxo Group Ltd | Senyawa-senyawa heterosiklik |
| ES2191187T3 (es) | 1996-07-13 | 2003-09-01 | Glaxo Group Ltd | Compuestos heteroaromaticos biciclicos como inhibidores de la proteina tirosin-quinasa. |
| HRP970371A2 (en) | 1996-07-13 | 1998-08-31 | Kathryn Jane Smith | Heterocyclic compounds |
| US6004967A (en) * | 1996-09-13 | 1999-12-21 | Sugen, Inc. | Psoriasis treatment with quinazoline compounds |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| EP0837063A1 (en) | 1996-10-17 | 1998-04-22 | Pfizer Inc. | 4-Aminoquinazoline derivatives |
| JP4713698B2 (ja) | 1997-03-05 | 2011-06-29 | スージェン， インク． | 疎水性薬剤の処方 |
| AR012634A1 (es) | 1997-05-02 | 2000-11-08 | Sugen Inc | Compuesto basado en quinazolina, composicion famaceutica que lo comprende, metodo para sintetizarlo, su uso, metodos de modulacion de la funcion deserina/treonina proteinaquinasa con dicho compuesto y metodo in vitro para identificar compuestos que modulan dicha funcion |
| US5929080A (en) * | 1997-05-06 | 1999-07-27 | American Cyanamid Company | Method of treating polycystic kidney disease |
| ATE241986T1 (de) | 1997-05-06 | 2003-06-15 | Wyeth Corp | Verwendung von chinazolin verbindungen zur behandlung von polyzystischer nierenkrankheit |
| ZA986732B (en) | 1997-07-29 | 1999-02-02 | Warner Lambert Co | Irreversible inhibitiors of tyrosine kinases |
| TW436485B (en) | 1997-08-01 | 2001-05-28 | American Cyanamid Co | Substituted quinazoline derivatives |
| CN1278176A (zh) | 1997-11-06 | 2000-12-27 | 美国氰胺公司 | 喹唑啉衍生物作为用于治疗结肠息肉的酪氨酸激酶抑制剂的应用 |
| JP4245682B2 (ja) | 1997-12-25 | 2009-03-25 | 協和発酵キリン株式会社 | キノリン誘導体、イソキノリン誘導体、およびシンノリン誘導体、並びに抗炎症剤および抗アレルギー剤 |
| GB9800575D0 (en) | 1998-01-12 | 1998-03-11 | Glaxo Group Ltd | Heterocyclic compounds |
| RS49779B (sr) | 1998-01-12 | 2008-06-05 | Glaxo Group Limited, | Biciklična heteroaromatična jedinjenja kao inhibitori protein tirozin kinaze |
| WO1999061428A1 (en) | 1998-05-28 | 1999-12-02 | Parker Hughes Institute | Quinazolines for treating brain tumor |
| WO2000000202A1 (en) | 1998-06-30 | 2000-01-06 | Parker Hughes Institute | Method for inhibiting c-jun expression using jak-3 inhibitors |
| AU5391099A (en) | 1998-07-30 | 2000-02-21 | American Home Products Corporation | Substituted quinazoline derivatives |
| US6384223B1 (en) * | 1998-07-30 | 2002-05-07 | American Home Products Corporation | Substituted quinazoline derivatives |
| WO2000009481A1 (en) | 1998-08-11 | 2000-02-24 | Takeda Chemical Industries, Ltd. | Cyclic amide compounds, process for producing the same, intermediates thereof and herbicides |
| US6313129B1 (en) | 1998-08-21 | 2001-11-06 | Hughes Institute | Therapeutic compounds |
| BR9914164A (pt) | 1998-09-29 | 2001-06-26 | American Cyanamid Co | Composto, método para o tratamento, inibição do crescimento de, ou erradiacação de um neoplasma, e de doença de rim policìstico, em um mamìfero em necessidade do mesmo, composição farmacêutica, e, processo para preparar um composto |
| US6297258B1 (en) * | 1998-09-29 | 2001-10-02 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| ATE232205T1 (de) | 1998-10-01 | 2003-02-15 | Astrazeneca Ab | Chinolin- und chinazolin derivate und ihre verwendung als inhibitoren von krankheiten, bei denen cytokine beteiligt wird |
| TW575567B (en) | 1998-10-23 | 2004-02-11 | Akzo Nobel Nv | Serine protease inhibitor |
| UA71945C2 (en) | 1999-01-27 | 2005-01-17 | Pfizer Prod Inc | Substituted bicyclic derivatives being used as anticancer agents |
| SK288365B6 (sk) | 1999-02-10 | 2016-07-01 | Astrazeneca Ab | Medziprodukty pre chinazolínové deriváty ako inhibítory angiogenézy |
| TR200102505T2 (tr) | 1999-02-27 | 2003-01-21 | Boehringer Ingelheim Pharma Kg | 4-amino-kinazolin ve kinolin türevleri. |
| US6080747A (en) * | 1999-03-05 | 2000-06-27 | Hughes Institute | JAK-3 inhibitors for treating allergic disorders |
| DE19911509A1 (de) | 1999-03-15 | 2000-09-21 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| US6518283B1 (en) | 1999-05-28 | 2003-02-11 | Celltech R&D Limited | Squaric acid derivatives |
| GB9917408D0 (en) | 1999-07-23 | 1999-09-22 | Smithkline Beecham Plc | Compounds |
| PL353267A1 (en) | 1999-08-12 | 2003-11-03 | American Cyanamid Company | Nsaid and efgr kinase inhibitor containing composition for the treatment or inhibition of colonic polyps and colorectal cancer |
| GB9922171D0 (en) | 1999-09-21 | 1999-11-17 | Zeneca Ltd | Chemical compounds |
| GB9922173D0 (en) | 1999-09-21 | 1999-11-17 | Zeneca Ltd | Chemical compounds |
| KR20020032608A (ko) | 1999-09-21 | 2002-05-03 | 다비드 에 질레스 | 퀴나졸린 화합물 및 이를 함유하는 제약 조성물 |
| US7709479B1 (en) * | 1999-09-21 | 2010-05-04 | Astrazeneca | Quinazoline derivatives and their use as pharmaceuticals |
| EP1230225A2 (en) | 1999-11-01 | 2002-08-14 | Eli Lilly And Company | Pharmaceutically active 4-substituted pyrimidine derivatives |
| JP2003518023A (ja) | 1999-11-30 | 2003-06-03 | パーカー ヒューズ インスティテュート | トロンビン誘導血小板凝集の阻害剤 |
| ES2267748T3 (es) | 2000-04-07 | 2007-03-16 | Astrazeneca Ab | Compuestos de quinazolina. |
| UA73993C2 (uk) | 2000-06-06 | 2005-10-17 | Астразенека Аб | Хіназолінові похідні для лікування пухлин та фармацевтична композиція |
| HRP20021005A2 (en) | 2000-06-22 | 2004-02-29 | Pfizer Prod Inc | Substituted bicyclic derivatives for the treatment of abnormal cell growth |
| DE10042059A1 (de) | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| US20020082270A1 (en) * | 2000-08-26 | 2002-06-27 | Frank Himmelsbach | Aminoquinazolines which inhibit signal transduction mediated by tyrosine kinases |
| EP1719770A3 (en) | 2000-09-21 | 2008-03-05 | Smithkline Beecham Plc | Quinoline derivatives as antibacterials |
| US6849625B2 (en) | 2000-10-13 | 2005-02-01 | Astrazeneca Ab | Quinazoline derivatives with anti-tumour activity |
| US20040063733A1 (en) | 2000-10-25 | 2004-04-01 | Lambert Christine Marie Paul | Quinazoline derivatives |
| EP1337524A1 (en) | 2000-11-02 | 2003-08-27 | AstraZeneca AB | Substituted quinolines as antitumor agents |
| ATE369894T1 (de) | 2000-11-22 | 2007-09-15 | Novartis Pharma Gmbh | Kombination enthaltend ein mittel zur verminderung von vegf-aktivität und ein mittel zur verminderung von egf-aktivität |
| AUPR201600A0 (en) | 2000-12-11 | 2001-01-11 | Fujisawa Pharmaceutical Co., Ltd. | Quinazolinone derivative |
| GB0101577D0 (en) | 2001-01-22 | 2001-03-07 | Smithkline Beecham Plc | Compounds |
| WO2002062767A1 (en) | 2001-02-07 | 2002-08-15 | Sumitomo Pharmaceuticals Company, Limited | Novel quinazoline derivatives |
| NZ516873A (en) | 2001-02-12 | 2003-11-28 | Warner Lambert Co | Compositions containing retinoids and erb inhibitors and their use in inhibiting retinoid skin damage |
| EP1369418B1 (en) | 2001-02-21 | 2010-07-28 | Mitsubishi Tanabe Pharma Corporation | Quinazoline derivatives |
| PL364625A1 (en) | 2001-02-23 | 2004-12-13 | Merck & Co, Inc. | N-substituted nonaryl-heterocyclic nmda/nr2b antagonists |
| US6562319B2 (en) * | 2001-03-12 | 2003-05-13 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Radiolabeled irreversible inhibitors of epidermal growth factor receptor tyrosine kinase and their use in radioimaging and radiotherapy |
| US20030125344A1 (en) | 2001-03-23 | 2003-07-03 | Bayer Corporation | Rho-kinase inhibitors |
| WO2002092578A1 (en) | 2001-05-14 | 2002-11-21 | Astrazeneca Ab | Quinazoline derivatives |
| WO2002092577A1 (en) | 2001-05-14 | 2002-11-21 | Astrazeneca Ab | Quinazoline derivatives |
| JPWO2002094790A1 (ja) * | 2001-05-23 | 2004-09-09 | 三菱ウェルファーマ株式会社 | 縮合ヘテロ環化合物およびその医薬用途 |
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| 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 |
| PL373848A1 (en) | 2001-12-12 | 2005-09-19 | Pfizer Products Inc. | Quinazoline derivatives for the treatment of abnormal cell growth |
| TWI324597B (en) | 2002-03-28 | 2010-05-11 | Astrazeneca Ab | Quinazoline derivatives |
| US6924285B2 (en) | 2002-03-30 | 2005-08-02 | Boehringer Ingelheim Pharma Gmbh & Co. | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| CA2476008C (en) | 2002-03-30 | 2011-12-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| EP2280003B1 (en) | 2002-07-15 | 2014-04-02 | Symphony Evolution, Inc. | Process for preparing receptor-type kinase modulators |
| WO2004046101A2 (en) | 2002-11-20 | 2004-06-03 | Array Biopharma, Inc. | Cyanoguanidines and cyanoamidines as erbb2 and egfr inhibitors |
| JP2006515871A (ja) | 2003-01-23 | 2006-06-08 | ティー．ケイ． シグナル リミテッド | 上皮増殖因子受容体チロシンキナーゼの不可逆阻害剤ならびにその使用 |
| GB0309009D0 (en) * | 2003-04-22 | 2003-05-28 | Astrazeneca Ab | Quinazoline derivatives |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| GB0317665D0 (en) * | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| JP2007500177A (ja) * | 2003-07-29 | 2007-01-11 | アストラゼネカ アクチボラグ | チロシンキナーゼ阻害剤としてのピペリジルキナゾリン誘導体 |
| GB0318423D0 (en) | 2003-08-06 | 2003-09-10 | Astrazeneca Ab | Chemical compounds |
| US20070032508A1 (en) * | 2003-09-16 | 2007-02-08 | Bradbury Robert H | Quinazoline derivatives as tyrosine kinase inhibitors |
| AU2004272345A1 (en) | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| GB0321648D0 (en) | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| ES2305844T3 (es) | 2003-09-16 | 2008-11-01 | Astrazeneca Ab | Derivados de quinazolina como inhibidores de tirosina cinasa. |
| AU2004272346A1 (en) | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| CN1882570B (zh) | 2003-09-19 | 2010-12-08 | 阿斯利康(瑞典)有限公司 | 喹唑啉衍生物 |
| WO2005028469A1 (en) | 2003-09-19 | 2005-03-31 | Astrazeneca Ab | Quinazoline derivatives |
| KR20060100388A (ko) * | 2003-09-25 | 2006-09-20 | 아스트라제네카 아베 | 퀴나졸린 유도체 |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| DE10350717A1 (de) | 2003-10-30 | 2005-06-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verwendung von Tyrosinkinase-Inhibitoren zur Behandlung inflammatorischer Prozesse |
| 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 |
| WO2005097134A2 (en) | 2004-03-31 | 2005-10-20 | The Scripps Research Institute | Quinazoline based protein kinase inhibitors |
| AU2005250224A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as ERBB receptor tyrosine kinases |
| AU2005263972A1 (en) | 2004-07-23 | 2006-01-26 | Astrazeneca Ab | Method of predicting the responsiveness of a tumor to erbB receptor drugs |
| EP1838712B8 (en) | 2004-12-14 | 2011-10-12 | AstraZeneca AB | Pyrazolopyrimidine compounds as antitumor agents |
| MX2007010399A (es) | 2005-02-26 | 2007-09-25 | Astrazeneca Ab | Derivados de quinazolina en la forma de inhibidores de cinasa de tirosina. |
| GB0504475D0 (en) | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| GB0504474D0 (en) | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| GB0508717D0 (en) | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| GB0508715D0 (en) | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| 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 |
| 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 |
| 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 |
| 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 |
-
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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2007511491A5 (https=) | ||
| JP2008501675A5 (https=) | ||
| JP2006524218A5 (https=) | ||
| JP4135318B2 (ja) | 新規なピリミジン−５−カルボキサミド誘導体 | |
| ES2261658T3 (es) | Antagonistas nmda/nr2b heterociclicos no arilicos n-sustituidos. | |
| JP2007523072A5 (https=) | ||
| KR101985050B1 (ko) | 피라진카르복사미드 화합물 | |
| US7872005B2 (en) | 2-substituted heteroaryl compounds | |
| US20100010022A1 (en) | Cancer treatment method | |
| JP5275628B2 (ja) | 複素環式化合物および使用方法 | |
| US20060069110A1 (en) | Substituted heterocyclic compounds and methods of use | |
| JP2002542193A (ja) | 環状タンパク質チロシンキナーゼ阻害剤 | |
| RU2001130452A (ru) | Циклические ингибиторы протеинтирозинкиназ | |
| RU2014147191A (ru) | Амидопроизводные как блокаторы ttx-s | |
| CA2494091A1 (en) | Substituted furo [2,3-b| pyridine derivatives | |
| TW200534853A (en) | Synergistic methods and compositions for treating cancer | |
| JP2007505874A5 (https=) | ||
| JP2015514679A5 (https=) | ||
| JP2008505877A5 (https=) | ||
| JP2016516028A5 (https=) | ||
| JP2018514562A (ja) | 小分子インテグリン受容体−リガンドアゴニストアジュバントを含む免疫治療のための新規組成物及び方法 | |
| EP1663241B1 (en) | 5-arylpyrimidines as anticancer agents | |
| JP2007506746A5 (https=) | ||
| EP3590516B1 (en) | Antitumor-effect enhancer using pyrazolo[3,4-d]pyrimidine compound | |
| JP2008523134A5 (https=) |