JP2006524218A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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 (enExample) | 2007-03-15 |
Family
ID=9957022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 (enExample) |
| EP (1) | EP1631292B1 (enExample) |
| JP (1) | JP2006524218A (enExample) |
| KR (1) | KR20060006821A (enExample) |
| CN (1) | CN100406453C (enExample) |
| AT (1) | ATE438402T1 (enExample) |
| AU (1) | AU2004231349A1 (enExample) |
| BR (1) | BRPI0409633A (enExample) |
| CA (1) | CA2526897A1 (enExample) |
| DE (1) | DE602004022404D1 (enExample) |
| ES (1) | ES2329576T3 (enExample) |
| GB (1) | GB0309009D0 (enExample) |
| MX (1) | MXPA05011332A (enExample) |
| NO (1) | NO20054856L (enExample) |
| NZ (1) | NZ543015A (enExample) |
| WO (1) | WO2004093880A1 (enExample) |
| ZA (1) | ZA200508525B (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2004116911A (ru) * | 2001-11-03 | 2005-11-10 | Астразенека Аб (Se) | Производные хиназолина в качестве противоопухолевых средств |
| 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 |
| EP1636195A1 (en) * | 2003-05-27 | 2006-03-22 | Pfizer Products Inc. | Quinazolines and pyrido[3,4-d]pyrimidines as receptor tyrosine kinase inhibitors |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| BRPI0414488A (pt) * | 2003-09-16 | 2006-11-14 | Astrazeneca Ab | derivado de quinazolina, composição farmacêutica, uso de um derivado de quinazolina, métodos para produzir um efeito anti - proliferativo em um animal de sangue quente, para prevenção ou tratamento de tumores em um aminal de sangue quente, para fornecer um efeito inibidor da tirosina quinase de egfr seletivo em um animal de sangue quente e para tratar um cáncer em um animal de sangue quente e, processo para a preparação de um derivado de quinazolina |
| MXPA06002963A (es) * | 2003-09-16 | 2006-06-14 | Astrazeneca Ab | Derivados de quinazolina como inhibidores de cinasa de tirosina. |
| WO2005026150A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| WO2005026156A1 (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 |
| ATE413389T1 (de) * | 2004-02-03 | 2008-11-15 | Astrazeneca Ab | Chinazolinderivate |
| CA2567832A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as erbb receptor tyrosine kinases |
| 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 |
| WO2007034143A1 (en) * | 2005-09-20 | 2007-03-29 | Astrazeneca Ab | Quinazoline derivatives as anticancer agents |
| ES2354457T3 (es) * | 2005-09-20 | 2011-03-15 | Astrazeneca Ab | Compuestos de 4-(1h-indazol-5-il-amino)-quinazolina como inhibidores del receptor erbb de la tirosina quinasa para el tratamiento del cáncer. |
| 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 |
| EP1957499A1 (en) * | 2005-12-02 | 2008-08-20 | AstraZeneca AB | 4-anilino-substituted quinazoline derivatives as tyrosine kinase inhibitors |
| CA2662617C (en) | 2006-09-11 | 2014-11-18 | Changgeng Qian | 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 |
| CA2663436A1 (en) * | 2006-10-04 | 2008-04-10 | 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 |
| JP5377332B2 (ja) | 2007-02-06 | 2013-12-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 二環式へテロ環、それらの化合物を含む薬剤、その使用及びその製法 |
| TWI377944B (en) * | 2007-06-05 | 2012-12-01 | Hanmi Holdings Co Ltd | Novel amide derivative for inhibiting the growth of cancer cells |
| EP2220054A2 (en) | 2007-10-29 | 2010-08-25 | Natco Pharma Limited | Novel 4-(tetrazol-5-yl)-quinazoline derivatives as anti cancer agents |
| WO2009098061A1 (de) | 2008-02-07 | 2009-08-13 | Boehringer Ingelheim International Gmbh | Spirocyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| MX2010012442A (es) | 2008-05-13 | 2011-10-11 | Astrazeneca Ab | Sal de fumarato de 4-(3-cloro-2-fluoroanilino)-7-metoxi-6-{[1-(n-m etilcarbamoilmetil) piperidin-4-il]oxi}quinazolina. |
| 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 |
| US8055334B2 (en) * | 2008-12-11 | 2011-11-08 | 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 |
Family Cites Families (41)
| 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 |
| 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 |
| 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 |
| TW321649B (enExample) * | 1994-11-12 | 1997-12-01 | Zeneca Ltd | |
| 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 |
| GB9624482D0 (en) * | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| ID18666A (id) * | 1996-01-31 | 1998-04-30 | Gist Brocades Bv | Penggunaan komposisi komposisi yang terdiri dari senyawa senyawa stabil yang efektif secara biologi |
| GB9603095D0 (en) * | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| US6004967A (en) * | 1996-09-13 | 1999-12-21 | Sugen, Inc. | Psoriasis treatment with quinazoline compounds |
| DE19651439A1 (de) * | 1996-12-11 | 1998-06-18 | Hoechst Ag | Polymerisierbare Biaryle, Verfahren zur Herstellung und deren Verwendung |
| US5929080A (en) * | 1997-05-06 | 1999-07-27 | American Cyanamid Company | Method of treating polycystic kidney disease |
| US6384223B1 (en) * | 1998-07-30 | 2002-05-07 | American Home Products Corporation | Substituted quinazoline derivatives |
| US6297258B1 (en) * | 1998-09-29 | 2001-10-02 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| UA71945C2 (en) * | 1999-01-27 | 2005-01-17 | Pfizer Prod Inc | Substituted bicyclic derivatives being used as anticancer agents |
| 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 |
| US20020082270A1 (en) * | 2000-08-26 | 2002-06-27 | Frank Himmelsbach | Aminoquinazolines which inhibit signal transduction mediated by tyrosine kinases |
| 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 |
| US20040176361A1 (en) * | 2001-05-23 | 2004-09-09 | Masakazu Fujio | Fused heterocyclic compound and medicinal use thereof |
| RU2004116911A (ru) * | 2001-11-03 | 2005-11-10 | Астразенека Аб (Se) | Производные хиназолина в качестве противоопухолевых средств |
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| TW200813014A (en) * | 2002-03-28 | 2008-03-16 | 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 |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| CA2533345A1 (en) * | 2003-07-29 | 2005-02-10 | Astrazeneca Ab | Piperidyl-quinazoline derivatives as tyrosine kinase inhibitors |
| GB0317665D0 (en) * | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| BRPI0414488A (pt) * | 2003-09-16 | 2006-11-14 | Astrazeneca Ab | derivado de quinazolina, composição farmacêutica, uso de um derivado de quinazolina, métodos para produzir um efeito anti - proliferativo em um animal de sangue quente, para prevenção ou tratamento de tumores em um aminal de sangue quente, para fornecer um efeito inibidor da tirosina quinase de egfr seletivo em um animal de sangue quente e para tratar um cáncer em um animal de sangue quente e, processo para a preparação de um derivado de quinazolina |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| WO2005026150A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| MXPA06002963A (es) * | 2003-09-16 | 2006-06-14 | Astrazeneca Ab | Derivados de quinazolina como inhibidores de cinasa de tirosina. |
| DE602004004811T2 (de) * | 2003-09-19 | 2007-11-22 | Astrazeneca Ab | Chinazolinderivate |
| MXPA06003341A (es) * | 2003-09-25 | 2006-06-08 | Astrazeneca Ab | Derivados de quinazolina. |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) * | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| ATE413389T1 (de) * | 2004-02-03 | 2008-11-15 | Astrazeneca Ab | Chinazolinderivate |
| CA2567832A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as erbb receptor tyrosine kinases |
-
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 KR KR1020057020096A patent/KR20060006821A/ko not_active Withdrawn
- 2004-04-20 AU AU2004231349A patent/AU2004231349A1/en not_active Abandoned
- 2004-04-20 US US10/554,202 patent/US20070149546A1/en not_active Abandoned
- 2004-04-20 DE DE602004022404T patent/DE602004022404D1/de not_active Expired - Fee Related
- 2004-04-20 EP EP04728367A patent/EP1631292B1/en not_active Expired - Lifetime
- 2004-04-20 AT AT04728367T patent/ATE438402T1/de not_active IP Right Cessation
- 2004-04-20 WO PCT/GB2004/001713 patent/WO2004093880A1/en not_active Ceased
- 2004-04-20 NZ NZ543015A patent/NZ543015A/en unknown
- 2004-04-20 CN CNB2004800170469A patent/CN100406453C/zh not_active Expired - Fee Related
- 2004-04-20 JP JP2006506155A patent/JP2006524218A/ja active Pending
- 2004-04-20 CA CA002526897A patent/CA2526897A1/en not_active Abandoned
- 2004-04-20 MX MXPA05011332A patent/MXPA05011332A/es unknown
-
2005
- 2005-10-20 ZA ZA200508525A patent/ZA200508525B/en unknown
- 2005-10-20 NO NO20054856A patent/NO20054856L/no not_active Application Discontinuation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2317291C2 (ru) | Производные пиримидина в качестве модуляторов рецептора инсулинподобного фактора роста 1 (igf-1), фармацевтическая композиция, способы получения (варианты) и применение | |
| JP2007505874A5 (enExample) | ||
| ES2236178T3 (es) | Nuevos compuestos de imidazolina. | |
| RU2413727C2 (ru) | Производные пиразола и их применение в качестве ингибиторов рецепторных тирозинкиназ | |
| JP5275628B2 (ja) | 複素環式化合物および使用方法 | |
| US20040209930A1 (en) | Synergistic methods and compositions for treating cancer | |
| Flick et al. | Synthetic approaches to new drugs approved during 2018 | |
| EP2210880B1 (en) | Benzoxazinone derivatives | |
| RU2017124425A (ru) | Производные 2,4-диоксо-хиназолин-6-сульфонамида в качестве ингибиторов parg | |
| JP2008501675A5 (enExample) | ||
| JP2007511491A5 (enExample) | ||
| CA2497237A1 (en) | N-substituted-2-oxodihydropyridine derivatives | |
| RU2005107463A (ru) | Циклические протеины ингибиторов тирозинкиназы | |
| US20100010022A1 (en) | Cancer treatment method | |
| JP2002528537A (ja) | ２−アミノ−チアゾール誘導体類、それらの製造方法および抗癌剤としてのそれらの使用 | |
| ZA200508525B (en) | 4-Anilino-quinazoline derivatives as antiproliferative agents | |
| RU2003118448A (ru) | Производные замещенного триазолдиамина и их применение в качестве ингибиторов киназы | |
| CA2391643A1 (en) | Gamma-hydroxy-2-(fluoroalkylaminocarbonyl)-1-piperazinepentanamides as hiv protease inhibitors | |
| JP2017538750A5 (enExample) | ||
| CA2454703A1 (en) | Novel thiophene carboxamide derivatives | |
| JP2004517840A (ja) | フェニルアセトアミド−ピラゾール誘導体およびそれの抗腫瘍薬としての使用 | |
| JP2014523400A5 (enExample) | ||
| IL276575B2 (en) | Inhibitors of btk and mutants thereof | |
| AU2020375720A1 (en) | Improved methods, kits, compositions and dosing regimens for the use of heterocyclic inhibitors of ERK1 and ERK2 | |
| RU2019136279A (ru) | C5 -Анилинохиназолиновые соединения и их использование в лечении рака |