JP2004517048A5 - - Google Patents
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- JP2004517048A5 JP2004517048A5 JP2002523888A JP2002523888A JP2004517048A5 JP 2004517048 A5 JP2004517048 A5 JP 2004517048A5 JP 2002523888 A JP2002523888 A JP 2002523888A JP 2002523888 A JP2002523888 A JP 2002523888A JP 2004517048 A5 JP2004517048 A5 JP 2004517048A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- oxo
- group
- fluorophenyl
- chloro
- 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.)
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- -1 2-oxo-morpholin-4-yl group Chemical group 0.000 description 71
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 35
- 150000001875 compounds Chemical class 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 5
- KMIVCBCOKOZZRN-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-(5-methyl-2-oxomorpholin-4-yl)but-2-enamide Chemical compound CC1COC(=O)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OCC3CC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 KMIVCBCOKOZZRN-UHFFFAOYSA-N 0.000 description 5
- ONOWKYWJTZDNCT-MRXNPFEDSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-[(3R)-3-methyl-2-oxomorpholin-4-yl]but-2-enamide Chemical compound C1COC(=O)[C@@H](C)N1CC=CC(=O)NC(C(=CC1=NC=N2)OCC3CC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 ONOWKYWJTZDNCT-MRXNPFEDSA-N 0.000 description 5
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 5
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- CCOKBACMAWRBJZ-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-(2-methyl-6-oxomorpholin-4-yl)but-2-enamide Chemical compound C1C(=O)OC(C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OCC3CC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 CCOKBACMAWRBJZ-UHFFFAOYSA-N 0.000 description 3
- ONOWKYWJTZDNCT-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-(3-methyl-2-oxomorpholin-4-yl)but-2-enamide Chemical compound C1COC(=O)C(C)N1CC=CC(=O)NC(C(=CC1=NC=N2)OCC3CC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 ONOWKYWJTZDNCT-UHFFFAOYSA-N 0.000 description 3
- GOEZUUHXYGDNCD-GOSISDBHSA-N ethyl (2R)-2-[[4-[[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]amino]-4-oxobut-2-enyl]-(2-hydroxyethyl)amino]propanoate Chemical compound N1=CN=C2C=C(OCC3CC3)C(NC(=O)C=CCN(CCO)[C@H](C)C(=O)OCC)=CC2=C1NC1=CC=C(F)C(Cl)=C1 GOEZUUHXYGDNCD-GOSISDBHSA-N 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- MQPOXBYCYDBMJH-UHFFFAOYSA-N 2-[[4-[[4-(3-bromoanilino)-7-methoxyquinazolin-6-yl]amino]-4-oxobut-2-enyl]-(2-hydroxyethyl)amino]acetic acid Chemical compound C=12C=C(NC(=O)C=CCN(CCO)CC(O)=O)C(OC)=CC2=NC=NC=1NC1=CC=CC(Br)=C1 MQPOXBYCYDBMJH-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- SEOUETYTEUFQGQ-UHFFFAOYSA-N N-[4-(3-bromoanilino)-7-methoxyquinazolin-6-yl]-4-(2-oxomorpholin-4-yl)but-2-enamide Chemical compound C=12C=C(NC(=O)C=CCN3CC(=O)OCC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(Br)=C1 SEOUETYTEUFQGQ-UHFFFAOYSA-N 0.000 description 2
- SMCDHGJQIQUNIM-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-(2,2-dimethyl-6-oxomorpholin-4-yl)but-2-enamide Chemical compound C1C(=O)OC(C)(C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OCC3CC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 SMCDHGJQIQUNIM-UHFFFAOYSA-N 0.000 description 2
- ZOOUDMWPZJXWEZ-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-(5,5-dimethyl-2-oxomorpholin-4-yl)but-2-enamide Chemical compound CC1(C)COC(=O)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OCC3CC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 ZOOUDMWPZJXWEZ-UHFFFAOYSA-N 0.000 description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- XWSRRYNPCDAWKP-UHFFFAOYSA-N ethyl 2-[[4-[[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]amino]-4-oxobut-2-enyl]-(2-hydroxy-2-methylpropyl)amino]acetate Chemical compound N1=CN=C2C=C(OCC3CC3)C(NC(=O)C=CCN(CC(=O)OCC)CC(C)(C)O)=CC2=C1NC1=CC=C(F)C(Cl)=C1 XWSRRYNPCDAWKP-UHFFFAOYSA-N 0.000 description 2
- OQFKTDPRJBLWPS-UHFFFAOYSA-N ethyl 2-[[4-[[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]amino]-4-oxobut-2-enyl]-(2-hydroxyethyl)amino]acetate Chemical compound N1=CN=C2C=C(OCC3CC3)C(NC(=O)C=CCN(CCO)CC(=O)OCC)=CC2=C1NC1=CC=C(F)C(Cl)=C1 OQFKTDPRJBLWPS-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 0 *c1cc2ncnc(NI=*)c2cc1N Chemical compound *c1cc2ncnc(NI=*)c2cc1N 0.000 description 1
- HTWMYCGEXASIGG-GOSISDBHSA-N 4-(5,5-dimethyl-2-oxomorpholin-4-yl)-N-[4-[[(1R)-1-phenylethyl]amino]quinazolin-6-yl]but-2-enamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C1=C2)=NC=NC1=CC=C2NC(=O)C=CCN1CC(=O)OCC1(C)C HTWMYCGEXASIGG-GOSISDBHSA-N 0.000 description 1
- WLCDWQKCHZPMLJ-ZWKOTPCHSA-N 4-[(2S)-2-methyl-6-oxomorpholin-4-yl]-N-[4-[[(1R)-1-phenylethyl]amino]quinazolin-6-yl]but-2-enamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C1=C2)=NC=NC1=CC=C2NC(=O)C=CCN1C[C@H](C)OC(=O)C1 WLCDWQKCHZPMLJ-ZWKOTPCHSA-N 0.000 description 1
- 210000000013 Bile Ducts Anatomy 0.000 description 1
- RWXILWHGFPAHPO-LJQANCHMSA-N C1(=CC=CC=C1)[C@@H](C)NC1=NC(=NC2=CC(=C(C=C12)NC(C=CCN1CC(OCC1(C)C)=O)=O)C1CC1)OC Chemical compound C1(=CC=CC=C1)[C@@H](C)NC1=NC(=NC2=CC(=C(C=C12)NC(C=CCN1CC(OCC1(C)C)=O)=O)C1CC1)OC RWXILWHGFPAHPO-LJQANCHMSA-N 0.000 description 1
- YHDXPFVJAIHRAS-WMZOPIPTSA-N C1C(=O)O[C@@H](C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)O[C@@H]3COCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 Chemical compound C1C(=O)O[C@@H](C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)O[C@@H]3COCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 YHDXPFVJAIHRAS-WMZOPIPTSA-N 0.000 description 1
- LLRDMIKQIZFZHD-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)NC1=NC(=NC2=CC(=C(C=C12)NC(C=CCN1CC(OC(C1)CC)=O)=O)C1CC1)OC Chemical compound ClC=1C=C(C=CC=1F)NC1=NC(=NC2=CC(=C(C=C12)NC(C=CCN1CC(OC(C1)CC)=O)=O)C1CC1)OC LLRDMIKQIZFZHD-UHFFFAOYSA-N 0.000 description 1
- CYGNAHMCEHQYRZ-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)NC1=NC(=NC2=CC(=C(C=C12)NC(C=CCN1CC(OCC1)=O)=O)C1CC1)OC Chemical compound ClC=1C=C(C=CC=1F)NC1=NC(=NC2=CC(=C(C=C12)NC(C=CCN1CC(OCC1)=O)=O)C1CC1)OC CYGNAHMCEHQYRZ-UHFFFAOYSA-N 0.000 description 1
- 241000565118 Cordylophora caspia Species 0.000 description 1
- 210000000232 Gallbladder Anatomy 0.000 description 1
- 210000001035 Gastrointestinal Tract Anatomy 0.000 description 1
- 210000003734 Kidney Anatomy 0.000 description 1
- 210000004072 Lung Anatomy 0.000 description 1
- VMDRYOBNPDPEFY-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(2-methoxyethoxy)quinazolin-6-yl]-4-(5,5-dimethyl-2-oxomorpholin-4-yl)but-2-enamide Chemical compound C=12C=C(NC(=O)C=CCN3C(COC(=O)C3)(C)C)C(OCCOC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 VMDRYOBNPDPEFY-UHFFFAOYSA-N 0.000 description 1
- PJUPDYXOPGQSMN-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-(2-oxomorpholin-4-yl)but-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=NC=NC1=CC(OCC1CC1)=C2NC(=O)C=CCN1CC(=O)OCC1 PJUPDYXOPGQSMN-UHFFFAOYSA-N 0.000 description 1
- CCOKBACMAWRBJZ-MRXNPFEDSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-[(2R)-2-methyl-6-oxomorpholin-4-yl]but-2-enamide Chemical compound C1C(=O)O[C@H](C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OCC3CC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 CCOKBACMAWRBJZ-MRXNPFEDSA-N 0.000 description 1
- CCOKBACMAWRBJZ-INIZCTEOSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-[(2S)-2-methyl-6-oxomorpholin-4-yl]but-2-enamide Chemical compound C1C(=O)O[C@@H](C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OCC3CC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 CCOKBACMAWRBJZ-INIZCTEOSA-N 0.000 description 1
- ONOWKYWJTZDNCT-INIZCTEOSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-[(3S)-3-methyl-2-oxomorpholin-4-yl]but-2-enamide Chemical compound C1COC(=O)[C@H](C)N1CC=CC(=O)NC(C(=CC1=NC=N2)OCC3CC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 ONOWKYWJTZDNCT-INIZCTEOSA-N 0.000 description 1
- PCJFYVJPOFXARK-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-[1,3-dioxolan-2-ylmethyl(methyl)amino]but-2-enamide Chemical compound O1CCOC1CN(C)CC=CC(=O)NC(C(=CC1=NC=N2)OCC3CC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 PCJFYVJPOFXARK-UHFFFAOYSA-N 0.000 description 1
- HBJJUSHREJSZCK-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(oxan-4-yloxy)quinazolin-6-yl]-4-(2,2-dimethyl-6-oxomorpholin-4-yl)but-2-enamide Chemical compound C1C(=O)OC(C)(C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OC3CCOCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 HBJJUSHREJSZCK-UHFFFAOYSA-N 0.000 description 1
- MZZRGWDBGCKNCG-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(oxan-4-yloxy)quinazolin-6-yl]-4-(5,5-dimethyl-2-oxomorpholin-4-yl)but-2-enamide Chemical compound CC1(C)COC(=O)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OC3CCOCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 MZZRGWDBGCKNCG-UHFFFAOYSA-N 0.000 description 1
- NCLFLVTUXADXQE-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-(oxolan-2-ylmethoxy)quinazolin-6-yl]-4-(5,5-dimethyl-2-oxomorpholin-4-yl)but-2-enamide Chemical compound CC1(C)COC(=O)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OCC3OCCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 NCLFLVTUXADXQE-UHFFFAOYSA-N 0.000 description 1
- YWGCPWOZUWEHGA-GOSISDBHSA-N N-[4-(3-chloro-4-fluoroanilino)-7-[(3R)-oxolan-3-yl]oxyquinazolin-6-yl]-4-(5,5-dimethyl-2-oxomorpholin-4-yl)but-2-enamide Chemical compound CC1(C)COC(=O)CN1CC=CC(=O)NC(C(=CC1=NC=N2)O[C@H]3COCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 YWGCPWOZUWEHGA-GOSISDBHSA-N 0.000 description 1
- YHDXPFVJAIHRAS-SJLPKXTDSA-N N-[4-(3-chloro-4-fluoroanilino)-7-[(3R)-oxolan-3-yl]oxyquinazolin-6-yl]-4-[(2R)-2-methyl-6-oxomorpholin-4-yl]but-2-enamide Chemical compound C1C(=O)O[C@H](C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)O[C@H]3COCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 YHDXPFVJAIHRAS-SJLPKXTDSA-N 0.000 description 1
- YHDXPFVJAIHRAS-FUHWJXTLSA-N N-[4-(3-chloro-4-fluoroanilino)-7-[(3R)-oxolan-3-yl]oxyquinazolin-6-yl]-4-[(2S)-2-methyl-6-oxomorpholin-4-yl]but-2-enamide Chemical compound C1C(=O)O[C@@H](C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)O[C@H]3COCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 YHDXPFVJAIHRAS-FUHWJXTLSA-N 0.000 description 1
- YWGCPWOZUWEHGA-SFHVURJKSA-N N-[4-(3-chloro-4-fluoroanilino)-7-[(3S)-oxolan-3-yl]oxyquinazolin-6-yl]-4-(5,5-dimethyl-2-oxomorpholin-4-yl)but-2-enamide Chemical compound CC1(C)COC(=O)CN1CC=CC(=O)NC(C(=CC1=NC=N2)O[C@@H]3COCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 YWGCPWOZUWEHGA-SFHVURJKSA-N 0.000 description 1
- YHDXPFVJAIHRAS-AEFFLSMTSA-N N-[4-(3-chloro-4-fluoroanilino)-7-[(3S)-oxolan-3-yl]oxyquinazolin-6-yl]-4-[(2R)-2-methyl-6-oxomorpholin-4-yl]but-2-enamide Chemical compound C1C(=O)O[C@H](C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)O[C@@H]3COCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 YHDXPFVJAIHRAS-AEFFLSMTSA-N 0.000 description 1
- YATAUUBWSCHJNQ-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-cyclobutyloxyquinazolin-6-yl]-4-(5,5-dimethyl-2-oxomorpholin-4-yl)but-2-enamide Chemical compound CC1(C)COC(=O)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OC3CCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 YATAUUBWSCHJNQ-UHFFFAOYSA-N 0.000 description 1
- WVKDOGWQTANXMX-MRXNPFEDSA-N N-[4-(3-chloro-4-fluoroanilino)-7-cyclobutyloxyquinazolin-6-yl]-4-[(2R)-2-methyl-6-oxomorpholin-4-yl]but-2-enamide Chemical compound C1C(=O)O[C@H](C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OC3CCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 WVKDOGWQTANXMX-MRXNPFEDSA-N 0.000 description 1
- WVKDOGWQTANXMX-INIZCTEOSA-N N-[4-(3-chloro-4-fluoroanilino)-7-cyclobutyloxyquinazolin-6-yl]-4-[(2S)-2-methyl-6-oxomorpholin-4-yl]but-2-enamide Chemical compound C1C(=O)O[C@@H](C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OC3CCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 WVKDOGWQTANXMX-INIZCTEOSA-N 0.000 description 1
- RHQSWQLBVJZSIR-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-cyclopentyloxyquinazolin-6-yl]-4-(5,5-dimethyl-2-oxomorpholin-4-yl)but-2-enamide Chemical compound CC1(C)COC(=O)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OC3CCCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 RHQSWQLBVJZSIR-UHFFFAOYSA-N 0.000 description 1
- SJNPYHNHNFJXCY-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]-4-(5,5-dimethyl-2-oxomorpholin-4-yl)but-2-enamide Chemical compound C=12C=C(NC(=O)C=CCN3C(COC(=O)C3)(C)C)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 SJNPYHNHNFJXCY-UHFFFAOYSA-N 0.000 description 1
- YDTSPMQRCGKWRK-CQSZACIVSA-N N-[4-(3-chloro-4-fluoroanilino)quinazolin-6-yl]-4-[(2R)-2-methyl-6-oxomorpholin-4-yl]but-2-enamide Chemical compound C1C(=O)O[C@H](C)CN1CC=CC(=O)NC1=CC=C(N=CN=C2NC=3C=C(Cl)C(F)=CC=3)C2=C1 YDTSPMQRCGKWRK-CQSZACIVSA-N 0.000 description 1
- WOWRAEPIBQSHBM-ZWKOTPCHSA-N N-[7-methoxy-4-[[(1R)-1-phenylethyl]amino]quinazolin-6-yl]-4-[(2S)-2-methyl-6-oxomorpholin-4-yl]but-2-enamide Chemical compound C1([C@@H](C)NC=2N=CN=C3C=C(C(=CC3=2)NC(=O)C=CCN2CC(=O)O[C@@H](C)C2)OC)=CC=CC=C1 WOWRAEPIBQSHBM-ZWKOTPCHSA-N 0.000 description 1
- 206010061529 Polyp Diseases 0.000 description 1
- 210000003491 Skin Anatomy 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10042060A DE10042060A1 (de) | 2000-08-26 | 2000-08-26 | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| PCT/EP2001/009537 WO2002018373A1 (de) | 2000-08-26 | 2001-08-18 | Chinazolin derivate, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004517048A JP2004517048A (ja) | 2004-06-10 |
| JP2004517048A5 true JP2004517048A5 (sk) | 2008-10-09 |
Family
ID=7653947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002523888A Pending JP2004517048A (ja) | 2000-08-26 | 2001-08-18 | キナゾリン誘導体、これらの化合物を含む医薬組成物、それらの使用及びそれらの調製方法 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1315717A1 (sk) |
| JP (1) | JP2004517048A (sk) |
| AU (1) | AU2001284021A1 (sk) |
| CA (1) | CA2417050C (sk) |
| DE (1) | DE10042060A1 (sk) |
| MX (1) | MXPA03000873A (sk) |
| WO (1) | WO2002018373A1 (sk) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1731511E (pt) | 1999-06-21 | 2015-11-13 | Boehringer Ingelheim Pharma | Heterociclos bicíclicos, medicamentos contendo estes compostos, a sua utilização e processos para a sua preparação |
| US7019012B2 (en) | 2000-12-20 | 2006-03-28 | Boehringer Ingelheim International Pharma Gmbh & Co. Kg | Quinazoline derivatives and pharmaceutical compositions containing them |
| 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 |
| DE10221018A1 (de) * | 2002-05-11 | 2003-11-27 | Boehringer Ingelheim Pharma | Verwendung von Hemmern der EGFR-vermittelten Signaltransduktion zur Behandlung von gutartiger Prostatahyperplasie (BPH)/Prostatahypertrophie |
| DE10307165A1 (de) * | 2003-02-20 | 2004-09-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, ihre Verwendung und Verfahren zu ihrer Herstellung |
| US7223749B2 (en) | 2003-02-20 | 2007-05-29 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles, pharmaceutical compositions containing these compounds, their use and processes for preparing them |
| GB0317665D0 (en) | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| PT1667992E (pt) | 2003-09-19 | 2007-04-30 | Astrazeneca Ab | Derivados de quinazolina |
| EP1720841B1 (en) | 2004-02-19 | 2015-11-04 | Rexahn Pharmaceuticals, Inc. | Quinazoline derivatives and therapeutic use thereof |
| US20060035893A1 (en) | 2004-08-07 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for treatment of respiratory and gastrointestinal disorders |
| PE20060777A1 (es) | 2004-12-24 | 2006-10-06 | Boehringer Ingelheim Int | Derivados de indolinona para el tratamiento o la prevencion de enfermedades fibroticas |
| MX2007010399A (es) | 2005-02-26 | 2007-09-25 | Astrazeneca Ab | Derivados de quinazolina en la forma de inhibidores de cinasa de tirosina. |
| WO2007055513A1 (en) * | 2005-11-08 | 2007-05-18 | Hanmi Pharm. Co., Ltd. | Quinazoline derivatives as a signal transduction inhibitor and method for the preparation thereof |
| KR100832594B1 (ko) * | 2005-11-08 | 2008-05-27 | 한미약품 주식회사 | 다중저해제로서의 퀴나졸린 유도체 및 이의 제조방법 |
| CA2629244C (en) | 2005-11-11 | 2014-08-05 | Boehringer Ingelheim International Gmbh | Quinazoline derivatives for the treatment of cancer diseases |
| WO2008034776A1 (en) | 2006-09-18 | 2008-03-27 | Boehringer Ingelheim International Gmbh | Method for treating cancer harboring egfr mutations |
| 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 |
| PL2245026T3 (pl) | 2008-02-07 | 2013-01-31 | Boehringer Ingelheim Int | Spirocykliczne heterocykle, leki zawierające te związki, ich zastosowanie i sposób ich produkcji |
| ES2444128T3 (es) | 2008-05-13 | 2014-02-24 | Astrazeneca Ab | Nueva SAL-554 |
| CA2733153C (en) | 2008-08-08 | 2016-11-08 | Boehringer Ingelheim International Gmbh | Cyclohexyloxy substituted heterocycles, pharmaceutical compositions containing these compounds and processes for preparing them |
| WO2010054285A2 (en) | 2008-11-10 | 2010-05-14 | National Health Research Institutes | Fused bicyclic and tricyclic pyrimidine compounds as tyrosine kinase inhibitors |
| ES2731901T3 (es) | 2009-07-06 | 2019-11-19 | Boehringer Ingelheim Int | Proceso para el secado de BIBW2992, de sus sales y de formulaciones farmacéuticas sólidas que comprenden este ingrediente activo |
| PH12012500097A1 (en) * | 2009-07-21 | 2011-01-27 | Shanghai Inst Organic Chem | Potent small molecule inhibitors of autophagy, and methods of use thereof |
| CN102382106A (zh) * | 2010-08-30 | 2012-03-21 | 黄振华 | 苯胺取代的喹唑啉衍生物 |
| WO2013135176A1 (zh) * | 2012-03-16 | 2013-09-19 | 苏州迈泰生物技术有限公司 | 氨基喹唑啉衍生物及其在制备抗恶性肿瘤药物中的用途 |
| US9242965B2 (en) | 2013-12-31 | 2016-01-26 | Boehringer Ingelheim International Gmbh | Process for the manufacture of (E)-4-N,N-dialkylamino crotonic acid in HX salt form and use thereof for synthesis of EGFR tyrosine kinase inhibitors |
| WO2018095353A1 (en) * | 2016-11-25 | 2018-05-31 | Sunshine Lake Pharma Co., Ltd. | Salts of aminoquinazoline derivative and uses thereof |
| CN115894455B (zh) * | 2021-09-30 | 2024-04-19 | 北京赛特明强医药科技有限公司 | 一种喹唑啉类化合物、组合物及其应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW436485B (en) * | 1997-08-01 | 2001-05-28 | American Cyanamid Co | Substituted quinazoline derivatives |
| CA2361174C (en) * | 1999-02-27 | 2009-10-27 | Boehringer Ingelheim Pharma Kg | 4-amino-quinazoline and quinoline derivatives having an inhibitory effect on signal transduction mediated by tyrosine kinases |
| DE19911509A1 (de) * | 1999-03-15 | 2000-09-21 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| PT1731511E (pt) * | 1999-06-21 | 2015-11-13 | Boehringer Ingelheim Pharma | Heterociclos bicíclicos, medicamentos contendo estes compostos, a sua utilização e processos para a sua preparação |
| DE19928281A1 (de) * | 1999-06-21 | 2000-12-28 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| DE10017539A1 (de) * | 2000-04-08 | 2001-10-11 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbingungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
-
2000
- 2000-08-26 DE DE10042060A patent/DE10042060A1/de not_active Withdrawn
-
2001
- 2001-08-18 AU AU2001284021A patent/AU2001284021A1/en not_active Abandoned
- 2001-08-18 WO PCT/EP2001/009537 patent/WO2002018373A1/de active Application Filing
- 2001-08-18 JP JP2002523888A patent/JP2004517048A/ja active Pending
- 2001-08-18 CA CA002417050A patent/CA2417050C/en not_active Expired - Fee Related
- 2001-08-18 EP EP01962953A patent/EP1315717A1/de not_active Withdrawn
- 2001-08-18 MX MXPA03000873A patent/MXPA03000873A/es unknown
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