JP2007511491A5 - - Google Patents
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- 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
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- 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
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- 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
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-
2003
- 2003-11-13 GB GBGB0326459.5A patent/GB0326459D0/en not_active Ceased
-
2004
- 2004-11-11 JP JP2006538946A patent/JP2007511491A/ja active Pending
- 2004-11-11 AU AU2004293250A patent/AU2004293250A1/en not_active Abandoned
- 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 CN CN201010119887A patent/CN101787019A/zh active Pending
- 2004-11-11 US US10/578,663 patent/US7625908B2/en not_active Expired - Fee Related
- 2004-11-11 CN CNA2004800404156A patent/CN1906178A/zh active Pending
- 2004-11-11 WO PCT/GB2004/004761 patent/WO2005051923A1/en not_active Ceased
- 2004-11-11 UY UY28610A patent/UY28610A1/es not_active Application Discontinuation
- 2004-11-11 EP EP04798484A patent/EP1685116A1/en not_active Withdrawn
- 2004-11-11 KR KR1020067011553A patent/KR20060127410A/ko 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
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