JP2006524218A5 - - Google Patents
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- Publication number
- JP2006524218A5 JP2006524218A5 JP2006506155A JP2006506155A JP2006524218A5 JP 2006524218 A5 JP2006524218 A5 JP 2006524218A5 JP 2006506155 A JP2006506155 A JP 2006506155A JP 2006506155 A JP2006506155 A JP 2006506155A JP 2006524218 A5 JP2006524218 A5 JP 2006524218A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- quinazoline
- chloro
- alkyl
- dimethylamino
- 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 38
- 150000003246 quinazolines Chemical class 0.000 claims 37
- -1 cyano, formyl Chemical group 0.000 claims 30
- 229910052739 hydrogen Inorganic materials 0.000 claims 29
- 239000001257 hydrogen Substances 0.000 claims 29
- 150000002431 hydrogen Chemical class 0.000 claims 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000000524 functional group Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 6
- 241001465754 Metazoa Species 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 230000002401 inhibitory effect Effects 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 3
- 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
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 3
- UZRURECKNYFBFA-UHFFFAOYSA-N 5-[1-(dimethylamino)propan-2-yloxy]-n-(3-methoxy-4-phenoxyphenyl)quinazolin-4-amine Chemical compound COC1=CC(NC=2C3=C(OC(C)CN(C)C)C=CC=C3N=CN=2)=CC=C1OC1=CC=CC=C1 UZRURECKNYFBFA-UHFFFAOYSA-N 0.000 claims 2
- 241000282412 Homo Species 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- YAQPCCRFWWPEIP-UHFFFAOYSA-N 2-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl-ethylamino]ethanol Chemical compound C=12C(OCCN(CCO)CC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 YAQPCCRFWWPEIP-UHFFFAOYSA-N 0.000 claims 1
- RCEKCCZKQXSNDJ-UHFFFAOYSA-N 2-[2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl-methylamino]ethanol Chemical compound C=12C(OCCN(CCO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 RCEKCCZKQXSNDJ-UHFFFAOYSA-N 0.000 claims 1
- XZBQSRDWZBFMFN-UHFFFAOYSA-N 2-[2-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]quinazolin-5-yl]oxyethyl-methylamino]ethanol Chemical compound C=12C(OCCN(CCO)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 XZBQSRDWZBFMFN-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- NDSDFOCWVKHPOY-QGZVFWFLSA-N 5-[(2r)-1-(dimethylamino)propan-2-yl]oxy-n-[3-methyl-4-(1,3-thiazol-4-ylmethoxy)phenyl]quinazolin-4-amine Chemical compound C=12C(O[C@@H](CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CSC=N1 NDSDFOCWVKHPOY-QGZVFWFLSA-N 0.000 claims 1
- RPZBHYXTHNVSOO-GOSISDBHSA-N 5-[(2r)-1-(dimethylamino)propan-2-yl]oxy-n-[3-methyl-4-(pyrazin-2-ylmethoxy)phenyl]quinazolin-4-amine Chemical compound C=12C(O[C@@H](CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CN=CC=N1 RPZBHYXTHNVSOO-GOSISDBHSA-N 0.000 claims 1
- ACDVGEQBERLOFY-LJQANCHMSA-N 5-[(2r)-1-(dimethylamino)propan-2-yl]oxy-n-[3-methyl-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine Chemical compound C=12C(O[C@@H](CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CC=CC=N1 ACDVGEQBERLOFY-LJQANCHMSA-N 0.000 claims 1
- YJIKEJDQXIUCCA-GOSISDBHSA-N 5-[(2r)-1-(dimethylamino)propan-2-yl]oxy-n-[3-methyl-4-[(5-methyl-1,2-oxazol-3-yl)methoxy]phenyl]quinazolin-4-amine Chemical compound C=12C(O[C@@H](CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC=1C=C(C)ON=1 YJIKEJDQXIUCCA-GOSISDBHSA-N 0.000 claims 1
- NYMSZIULEGRTIM-UHFFFAOYSA-N 5-[1-(dimethylamino)propan-2-yloxy]-n-[4-[(3-fluorophenyl)methoxy]phenyl]quinazolin-4-amine Chemical compound C=12C(OC(CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1)=CC=C1OCC1=CC=CC(F)=C1 NYMSZIULEGRTIM-UHFFFAOYSA-N 0.000 claims 1
- BWXRXGHSIQUIHR-UHFFFAOYSA-N 5-[2-(dimethylamino)-2-methylpropoxy]-n-[3-methyl-4-(1,3-thiazol-4-ylmethoxy)phenyl]quinazolin-4-amine Chemical compound C=12C(OCC(C)(C)N(C)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CSC=N1 BWXRXGHSIQUIHR-UHFFFAOYSA-N 0.000 claims 1
- PLARICIMQAJCPS-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-n-[3-fluoro-4-(1,3-thiazol-5-ylmethoxy)phenyl]quinazolin-4-amine Chemical compound C=12C(OCCN(C)C)=CC=CC2=NC=NC=1NC(C=C1F)=CC=C1OCC1=CN=CS1 PLARICIMQAJCPS-UHFFFAOYSA-N 0.000 claims 1
- VBGQNCSBWRAFPZ-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-n-[3-methoxy-4-(pyrazin-2-ylmethoxy)phenyl]quinazolin-4-amine Chemical compound COC1=CC(NC=2C3=C(OCCN(C)C)C=CC=C3N=CN=2)=CC=C1OCC1=CN=CC=N1 VBGQNCSBWRAFPZ-UHFFFAOYSA-N 0.000 claims 1
- DWXJFAPJDZORFQ-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-n-[3-methoxy-4-[(5-methyl-1,2-oxazol-3-yl)methoxy]phenyl]quinazolin-4-amine Chemical compound COC1=CC(NC=2C3=C(OCCN(C)C)C=CC=C3N=CN=2)=CC=C1OCC=1C=C(C)ON=1 DWXJFAPJDZORFQ-UHFFFAOYSA-N 0.000 claims 1
- GTQNCEGOXICCSG-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-n-[3-methyl-4-(1,3-thiazol-4-ylmethoxy)phenyl]quinazolin-4-amine Chemical compound C=12C(OCCN(C)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CSC=N1 GTQNCEGOXICCSG-UHFFFAOYSA-N 0.000 claims 1
- HIRLFPPHNKFNND-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-n-[3-methyl-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine Chemical compound C=12C(OCCN(C)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC1=CC=CC=N1 HIRLFPPHNKFNND-UHFFFAOYSA-N 0.000 claims 1
- DBCMUMKOCMCZPE-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-n-[3-methyl-4-[(5-methyl-1,2-oxazol-3-yl)methoxy]phenyl]quinazolin-4-amine Chemical compound C=12C(OCCN(C)C)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OCC=1C=C(C)ON=1 DBCMUMKOCMCZPE-UHFFFAOYSA-N 0.000 claims 1
- QYRUSCIBJGKEDD-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-n-[4-[(3-fluorophenyl)methoxy]phenyl]quinazolin-4-amine Chemical compound C=12C(OCCN(C)C)=CC=CC2=NC=NC=1NC(C=C1)=CC=C1OCC1=CC=CC(F)=C1 QYRUSCIBJGKEDD-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 150000008049 diazo compounds Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- BUWRINZBUWWEDM-UHFFFAOYSA-N n-(3-chloro-4-pyridin-2-yloxyphenyl)-5-[2-(dimethylamino)ethoxy]quinazolin-4-amine Chemical compound C=12C(OCCN(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OC1=CC=CC=N1 BUWRINZBUWWEDM-UHFFFAOYSA-N 0.000 claims 1
- HCEHQXRQLZKXLJ-OAHLLOKOSA-N n-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)phenyl]-5-[(2r)-1-(dimethylamino)propan-2-yl]oxyquinazolin-4-amine Chemical compound C=12C(O[C@@H](CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CSC=N1 HCEHQXRQLZKXLJ-OAHLLOKOSA-N 0.000 claims 1
- CYSDOTHZWCSZKE-UHFFFAOYSA-N n-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)phenyl]-5-[2-(dimethylamino)-2-methylpropoxy]quinazolin-4-amine Chemical compound C=12C(OCC(C)(C)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CSC=N1 CYSDOTHZWCSZKE-UHFFFAOYSA-N 0.000 claims 1
- QSPRUIUYBSEHKS-UHFFFAOYSA-N n-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)phenyl]-5-[2-(dimethylamino)ethoxy]quinazolin-4-amine Chemical compound C=12C(OCCN(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CSC=N1 QSPRUIUYBSEHKS-UHFFFAOYSA-N 0.000 claims 1
- XRPWUPLMKFTPKE-OAHLLOKOSA-N n-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylphenyl]-5-[(2r)-2-(dimethylamino)propoxy]quinazolin-4-amine Chemical class C=12C(OC[C@@H](C)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1SC1=NC=CN1C XRPWUPLMKFTPKE-OAHLLOKOSA-N 0.000 claims 1
- XRPWUPLMKFTPKE-HNNXBMFYSA-N n-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylphenyl]-5-[(2s)-2-(dimethylamino)propoxy]quinazolin-4-amine Chemical class C=12C(OC[C@H](C)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1SC1=NC=CN1C XRPWUPLMKFTPKE-HNNXBMFYSA-N 0.000 claims 1
- POEJAIRLJJKQIP-UHFFFAOYSA-N n-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylphenyl]-5-[2-(dimethylamino)ethoxy]quinazolin-4-amine Chemical compound C=12C(OCCN(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1SC1=NC=CN1C POEJAIRLJJKQIP-UHFFFAOYSA-N 0.000 claims 1
- XRPWUPLMKFTPKE-UHFFFAOYSA-N n-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylphenyl]-5-[2-(dimethylamino)propoxy]quinazolin-4-amine Chemical compound C=12C(OCC(C)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1SC1=NC=CN1C XRPWUPLMKFTPKE-UHFFFAOYSA-N 0.000 claims 1
- KSEHVVCEIFMPAP-MRXNPFEDSA-N n-[3-chloro-4-(pyrazin-2-ylmethoxy)phenyl]-5-[(2r)-1-(dimethylamino)propan-2-yl]oxyquinazolin-4-amine Chemical compound C=12C(O[C@@H](CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CN=CC=N1 KSEHVVCEIFMPAP-MRXNPFEDSA-N 0.000 claims 1
- KSEHVVCEIFMPAP-INIZCTEOSA-N n-[3-chloro-4-(pyrazin-2-ylmethoxy)phenyl]-5-[(2s)-1-(dimethylamino)propan-2-yl]oxyquinazolin-4-amine Chemical compound C=12C(O[C@H](CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CN=CC=N1 KSEHVVCEIFMPAP-INIZCTEOSA-N 0.000 claims 1
- KSEHVVCEIFMPAP-UHFFFAOYSA-N n-[3-chloro-4-(pyrazin-2-ylmethoxy)phenyl]-5-[1-(dimethylamino)propan-2-yloxy]quinazolin-4-amine Chemical compound C=12C(OC(CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CN=CC=N1 KSEHVVCEIFMPAP-UHFFFAOYSA-N 0.000 claims 1
- IAALPNXIKUZDIS-UHFFFAOYSA-N n-[3-chloro-4-(pyrazin-2-ylmethoxy)phenyl]-5-[2-(dimethylamino)ethoxy]quinazolin-4-amine Chemical compound C=12C(OCCN(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CN=CC=N1 IAALPNXIKUZDIS-UHFFFAOYSA-N 0.000 claims 1
- VBNCKTVKZOLLBE-QGZVFWFLSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[(2r)-1-(dimethylamino)propan-2-yl]oxyquinazolin-4-amine Chemical compound C=12C(O[C@@H](CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 VBNCKTVKZOLLBE-QGZVFWFLSA-N 0.000 claims 1
- FVPBEFDMQRFMTN-GOSISDBHSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[(2r)-1-[ethyl(methyl)amino]propan-2-yl]oxyquinazolin-4-amine Chemical compound C=12C(O[C@H](C)CN(C)CC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 FVPBEFDMQRFMTN-GOSISDBHSA-N 0.000 claims 1
- ASWOHKYJMBVUMQ-QGZVFWFLSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[(2r)-2-(dimethylamino)propoxy]quinazolin-4-amine Chemical compound C=12C(OC[C@@H](C)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ASWOHKYJMBVUMQ-QGZVFWFLSA-N 0.000 claims 1
- VBNCKTVKZOLLBE-KRWDZBQOSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[(2s)-1-(dimethylamino)propan-2-yl]oxyquinazolin-4-amine Chemical compound C=12C(O[C@H](CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 VBNCKTVKZOLLBE-KRWDZBQOSA-N 0.000 claims 1
- CRWYZERLVMMWAC-IBGZPJMESA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[(2s)-1-[2-methoxyethyl(methyl)amino]propan-2-yl]oxyquinazolin-4-amine Chemical class C=12C(O[C@@H](C)CN(C)CCOC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 CRWYZERLVMMWAC-IBGZPJMESA-N 0.000 claims 1
- ASWOHKYJMBVUMQ-KRWDZBQOSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[(2s)-2-(dimethylamino)propoxy]quinazolin-4-amine Chemical compound C=12C(OC[C@H](C)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ASWOHKYJMBVUMQ-KRWDZBQOSA-N 0.000 claims 1
- VBNCKTVKZOLLBE-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[1-(dimethylamino)propan-2-yloxy]quinazolin-4-amine Chemical compound C=12C(OC(CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 VBNCKTVKZOLLBE-UHFFFAOYSA-N 0.000 claims 1
- OHGYVCUFAYWBBF-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(dimethylamino)-2-methylpropoxy]quinazolin-4-amine Chemical compound C=12C(OCC(C)(C)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 OHGYVCUFAYWBBF-UHFFFAOYSA-N 0.000 claims 1
- PRXMRWHTAJZUKS-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(dimethylamino)ethoxy]quinazolin-4-amine Chemical compound C=12C(OCCN(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 PRXMRWHTAJZUKS-UHFFFAOYSA-N 0.000 claims 1
- ASWOHKYJMBVUMQ-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(dimethylamino)propoxy]quinazolin-4-amine Chemical compound C=12C(OCC(C)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ASWOHKYJMBVUMQ-UHFFFAOYSA-N 0.000 claims 1
- GGMPVIJJPAXYGY-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-[ethyl(methyl)amino]ethoxy]quinazolin-4-amine Chemical compound C=12C(OCCN(C)CC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 GGMPVIJJPAXYGY-UHFFFAOYSA-N 0.000 claims 1
- DFMRSEWDIRLZHL-QGZVFWFLSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-5-[(2r)-1-(dimethylamino)propan-2-yl]oxyquinazolin-4-amine Chemical compound C=12C(O[C@@H](CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 DFMRSEWDIRLZHL-QGZVFWFLSA-N 0.000 claims 1
- JTPQLYCWSKRRAL-QGZVFWFLSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-5-[(2r)-2-(dimethylamino)propoxy]quinazolin-4-amine Chemical compound C=12C(OC[C@@H](C)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 JTPQLYCWSKRRAL-QGZVFWFLSA-N 0.000 claims 1
- DFMRSEWDIRLZHL-KRWDZBQOSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-5-[(2s)-1-(dimethylamino)propan-2-yl]oxyquinazolin-4-amine Chemical compound C=12C(O[C@H](CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 DFMRSEWDIRLZHL-KRWDZBQOSA-N 0.000 claims 1
- JTPQLYCWSKRRAL-KRWDZBQOSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-5-[(2s)-2-(dimethylamino)propoxy]quinazolin-4-amine Chemical compound C=12C(OC[C@H](C)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 JTPQLYCWSKRRAL-KRWDZBQOSA-N 0.000 claims 1
- HXBOQOOIXMIEPR-UHFFFAOYSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-5-[2-(dimethylamino)ethoxy]quinazolin-4-amine Chemical compound C=12C(OCCN(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 HXBOQOOIXMIEPR-UHFFFAOYSA-N 0.000 claims 1
- JTPQLYCWSKRRAL-UHFFFAOYSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-5-[2-(dimethylamino)propoxy]quinazolin-4-amine Chemical compound C=12C(OCC(C)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 JTPQLYCWSKRRAL-UHFFFAOYSA-N 0.000 claims 1
- ZWYAFMLDNPRQAU-UHFFFAOYSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-5-[2-[ethyl(methyl)amino]ethoxy]quinazolin-4-amine Chemical compound C=12C(OCCN(C)CC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 ZWYAFMLDNPRQAU-UHFFFAOYSA-N 0.000 claims 1
- HBSLTUIIMXSYKH-UHFFFAOYSA-N n-[3-chloro-4-[(5-methyl-1,2-oxazol-3-yl)methoxy]phenyl]-5-[1-(dimethylamino)propan-2-yloxy]quinazolin-4-amine Chemical compound C=12C(OC(CN(C)C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC=1C=C(C)ON=1 HBSLTUIIMXSYKH-UHFFFAOYSA-N 0.000 claims 1
- DHMACBOIZHIAKP-UHFFFAOYSA-N n-[3-chloro-4-[(5-methyl-1,2-oxazol-3-yl)methoxy]phenyl]-5-[2-(dimethylamino)-2-methylpropoxy]quinazolin-4-amine Chemical compound C=12C(OCC(C)(C)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC=1C=C(C)ON=1 DHMACBOIZHIAKP-UHFFFAOYSA-N 0.000 claims 1
- OWNWTSLMCXMZQK-UHFFFAOYSA-N n-[3-chloro-4-[(5-methyl-1,2-oxazol-3-yl)methoxy]phenyl]-5-[2-(dimethylamino)ethoxy]quinazolin-4-amine Chemical compound C=12C(OCCN(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC=1C=C(C)ON=1 OWNWTSLMCXMZQK-UHFFFAOYSA-N 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0309009.9A GB0309009D0 (en) | 2003-04-22 | 2003-04-22 | Quinazoline derivatives |
| PCT/GB2004/001713 WO2004093880A1 (en) | 2003-04-22 | 2004-04-20 | 4-anilino-quinazoline derivatives as antiproliferative agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006524218A JP2006524218A (ja) | 2006-10-26 |
| JP2006524218A5 true JP2006524218A5 (https=) | 2007-03-15 |
Family
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| JP2006506155A Pending JP2006524218A (ja) | 2003-04-22 | 2004-04-20 | 増殖抑制薬としての４−アニリノキナゾリン誘導体 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20070149546A1 (https=) |
| EP (1) | EP1631292B1 (https=) |
| JP (1) | JP2006524218A (https=) |
| KR (1) | KR20060006821A (https=) |
| CN (1) | CN100406453C (https=) |
| AT (1) | ATE438402T1 (https=) |
| AU (1) | AU2004231349A1 (https=) |
| BR (1) | BRPI0409633A (https=) |
| CA (1) | CA2526897A1 (https=) |
| DE (1) | DE602004022404D1 (https=) |
| ES (1) | ES2329576T3 (https=) |
| GB (1) | GB0309009D0 (https=) |
| MX (1) | MXPA05011332A (https=) |
| NO (1) | NO20054856L (https=) |
| NZ (1) | NZ543015A (https=) |
| WO (1) | WO2004093880A1 (https=) |
| ZA (1) | ZA200508525B (https=) |
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| US20050043336A1 (en) * | 2001-11-03 | 2005-02-24 | Hennequin Laurent Francois Andre | Quinazoline derivatives as antitumor agents |
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| 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 |
| US20070021429A1 (en) * | 2003-04-09 | 2007-01-25 | Yves St-Denis | Condensed n-heterocyclic compounds and their use as crf receptor antagonists |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| BRPI0410720A (pt) * | 2003-05-27 | 2006-06-20 | Pfizer Prod Inc | quinazolinas e pirido[3,4-d]pirimidinas como inibidores do receptor de tirosina cinase |
| EP1664028A1 (en) * | 2003-09-16 | 2006-06-07 | AstraZeneca AB | Quinazoline derivatives as tyrosine kinase inhibitors |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| ATE395346T1 (de) * | 2003-09-16 | 2008-05-15 | Astrazeneca Ab | Chinazolinderivate als tyrosinkinaseinhibitoren |
| EP1664030A1 (en) * | 2003-09-16 | 2006-06-07 | AstraZeneca AB | Quinazoline derivatives |
| AU2004272346A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| GB0322409D0 (en) | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| DE602005010824D1 (de) | 2004-02-03 | 2008-12-18 | Astrazeneca Ab | Chinazolinderivate |
| BRPI0511741A (pt) * | 2004-06-04 | 2008-01-02 | Astrazeneca Ab | derivado de quinazolina ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, processo para a preparação de um derivado de quinazolina ou de um sal farmaceuticamente aceitável do mesmo |
| ATE501148T1 (de) * | 2004-12-14 | 2011-03-15 | Astrazeneca Ab | Pyrazolopyrimidinverbindungen als antitumormittel |
| GB0427917D0 (en) * | 2004-12-21 | 2005-01-26 | Astrazeneca Ab | Chemical compounds |
| GB0504474D0 (en) * | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| GB0508715D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| GB0508717D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| ATE488513T1 (de) * | 2005-09-20 | 2010-12-15 | Astrazeneca Ab | 4-(1h-indazol-5-ylamino)chinazolinverbindungen als inhibitoren der erbb-rezeptortyrosinkinase zur behandlung von krebs |
| 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 |
| EP1957499A1 (en) * | 2005-12-02 | 2008-08-20 | AstraZeneca AB | 4-anilino-substituted quinazoline derivatives as tyrosine kinase inhibitors |
| WO2007063293A1 (en) * | 2005-12-02 | 2007-06-07 | Astrazeneca Ab | Quinazoleine derivatives used as inhibitors of erbb tyrosine kinase |
| AU2007296746B2 (en) | 2006-09-11 | 2012-07-05 | Curis, Inc. | Quinazoline based EGFR inhibitors containing a zinc binding moiety |
| US7547781B2 (en) | 2006-09-11 | 2009-06-16 | Curis, Inc. | Quinazoline based EGFR inhibitors containing a zinc binding moiety |
| EP2079739A2 (en) * | 2006-10-04 | 2009-07-22 | Pfizer Products Inc. | Pyrido[4,3-d]pyrimidin-4(3h)-one derivatives as calcium receptor antagonists |
| EP1921070A1 (de) | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstelllung |
| AU2008212999A1 (en) | 2007-02-06 | 2008-08-14 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles, drugs containing said compounds, use thereof, and method for production thereof |
| TWI377944B (en) * | 2007-06-05 | 2012-12-01 | Hanmi Holdings Co Ltd | Novel amide derivative for inhibiting the growth of cancer cells |
| US8080558B2 (en) | 2007-10-29 | 2011-12-20 | Natco Pharma Limited | 4-(tetrazol-5-yl)-quinazoline derivatives as anti-cancer agent |
| US8497369B2 (en) | 2008-02-07 | 2013-07-30 | Boehringer Ingelheim International Gmbh | Spirocyclic heterocycles medicaments containing said compounds, use thereof and method for their production |
| JP5739802B2 (ja) | 2008-05-13 | 2015-06-24 | アストラゼネカ アクチボラグ | ４−（３−クロロ−２−フルオロアニリノ）−７−メトキシ−６−｛［１−（ｎ−メチルカルバモイルメチル）ピペリジン−４−イル］オキシ｝キナゾリンのフマル酸塩 |
| EP2313397B1 (de) | 2008-08-08 | 2016-04-20 | Boehringer Ingelheim International GmbH | Cyclohexyloxy-substituierte heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| CA2746650A1 (en) * | 2008-12-11 | 2010-06-17 | Proteus Biomedical, Inc. | Evaluation of gastrointestinal function using portable electroviscerography systems and methods of using the same |
| CN115260164B (zh) * | 2021-05-01 | 2024-03-26 | 杭州星鳌生物科技有限公司 | 新型4(3h)-喹唑啉酮类似物的制备方法、结构组成及其在抗肿瘤药物中的应用 |
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| TWI324597B (en) * | 2002-03-28 | 2010-05-11 | Astrazeneca Ab | Quinazoline derivatives |
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| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| GB0317665D0 (en) * | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| UY28441A1 (es) * | 2003-07-29 | 2005-02-28 | Astrazeneca Ab | Derivados de quinazolina |
| ATE395346T1 (de) * | 2003-09-16 | 2008-05-15 | Astrazeneca Ab | Chinazolinderivate als tyrosinkinaseinhibitoren |
| AU2004272346A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| EP1664028A1 (en) * | 2003-09-16 | 2006-06-07 | AstraZeneca AB | Quinazoline derivatives as tyrosine kinase inhibitors |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
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| WO2005030757A1 (en) * | 2003-09-25 | 2005-04-07 | Astrazeneca Ab | Quinazoline derivatives |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) * | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| DE602005010824D1 (de) * | 2004-02-03 | 2008-12-18 | Astrazeneca Ab | Chinazolinderivate |
| BRPI0511741A (pt) * | 2004-06-04 | 2008-01-02 | Astrazeneca Ab | derivado de quinazolina ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, processo para a preparação de um derivado de quinazolina ou de um sal farmaceuticamente aceitável do mesmo |
-
2003
- 2003-04-22 GB GBGB0309009.9A patent/GB0309009D0/en not_active Ceased
-
2004
- 2004-04-20 ES ES04728367T patent/ES2329576T3/es not_active Expired - Lifetime
- 2004-04-20 BR BRPI0409633-9A patent/BRPI0409633A/pt not_active Application Discontinuation
- 2004-04-20 AU AU2004231349A patent/AU2004231349A1/en not_active Abandoned
- 2004-04-20 NZ NZ543015A patent/NZ543015A/en unknown
- 2004-04-20 EP EP04728367A patent/EP1631292B1/en not_active Expired - Lifetime
- 2004-04-20 DE DE602004022404T patent/DE602004022404D1/de not_active Expired - Fee Related
- 2004-04-20 CN CNB2004800170469A patent/CN100406453C/zh not_active Expired - Fee Related
- 2004-04-20 WO PCT/GB2004/001713 patent/WO2004093880A1/en not_active Ceased
- 2004-04-20 AT AT04728367T patent/ATE438402T1/de not_active IP Right Cessation
- 2004-04-20 US US10/554,202 patent/US20070149546A1/en not_active Abandoned
- 2004-04-20 MX MXPA05011332A patent/MXPA05011332A/es unknown
- 2004-04-20 CA CA002526897A patent/CA2526897A1/en not_active Abandoned
- 2004-04-20 KR KR1020057020096A patent/KR20060006821A/ko not_active Withdrawn
- 2004-04-20 JP JP2006506155A patent/JP2006524218A/ja active Pending
-
2005
- 2005-10-20 ZA ZA200508525A patent/ZA200508525B/en unknown
- 2005-10-20 NO NO20054856A patent/NO20054856L/no not_active Application Discontinuation
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