JP2007505874A5 - - Google Patents
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- Publication number
- JP2007505874A5 JP2007505874A5 JP2006526685A JP2006526685A JP2007505874A5 JP 2007505874 A5 JP2007505874 A5 JP 2007505874A5 JP 2006526685 A JP2006526685 A JP 2006526685A JP 2006526685 A JP2006526685 A JP 2006526685A JP 2007505874 A5 JP2007505874 A5 JP 2007505874A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- phenyl
- oxy
- quinazolin
- 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 151
- -1 hydroxy, cyano, Amino, carboxy, carbamoyl Chemical group 0.000 claims 82
- 150000003246 quinazolines Chemical class 0.000 claims 43
- 229910052757 nitrogen Inorganic materials 0.000 claims 39
- 125000001424 substituent group Chemical group 0.000 claims 36
- 125000003545 alkoxy group Chemical group 0.000 claims 31
- 125000000623 heterocyclic group Chemical group 0.000 claims 31
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 20
- 125000005843 halogen group Chemical group 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 18
- 125000003282 alkyl amino group Chemical group 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 16
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 14
- 125000005236 alkanoylamino group Chemical group 0.000 claims 13
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 12
- 125000000304 alkynyl group Chemical group 0.000 claims 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 11
- 125000001589 carboacyl group Chemical group 0.000 claims 11
- 125000004423 acyloxy group Chemical group 0.000 claims 10
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 10
- 125000004414 alkyl thio group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000000524 functional group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 150000001721 carbon Chemical group 0.000 claims 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 241001465754 Metazoa Species 0.000 claims 4
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims 4
- 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 238000003780 insertion Methods 0.000 claims 2
- 230000037431 insertion Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 2
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- DMLYTGPBYWHKHU-UHFFFAOYSA-N (2-amino-2-oxoethyl) acetate Chemical compound CC(=O)OCC(N)=O DMLYTGPBYWHKHU-UHFFFAOYSA-N 0.000 claims 1
- YNSPLPVYZNETCS-WIYYLYMNSA-N (2r)-1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxypropan-1-one Chemical compound C[C@@H](O)C(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 YNSPLPVYZNETCS-WIYYLYMNSA-N 0.000 claims 1
- YNSPLPVYZNETCS-GHTZIAJQSA-N (2s)-1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxypropan-1-one Chemical compound C[C@H](O)C(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 YNSPLPVYZNETCS-GHTZIAJQSA-N 0.000 claims 1
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims 1
- NSANTJIAVWVLHA-WZONZLPQSA-N 1-[(2r)-2-[(1r)-1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound O([C@H](C)[C@@H]1N(CCC1)C(=O)CO)C(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 NSANTJIAVWVLHA-WZONZLPQSA-N 0.000 claims 1
- NSANTJIAVWVLHA-FDDCHVKYSA-N 1-[(2r)-2-[(1s)-1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxyethyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound O([C@@H](C)[C@@H]1N(CCC1)C(=O)CO)C(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 NSANTJIAVWVLHA-FDDCHVKYSA-N 0.000 claims 1
- HWOCTTOWPSPEAG-GOSISDBHSA-N 1-[(2r)-2-[[4-(3-chloro-4-pyridin-3-yloxyanilino)quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OC=4C=NC=CC=4)=CC=3)=C12 HWOCTTOWPSPEAG-GOSISDBHSA-N 0.000 claims 1
- NRMFKTJVFAJMNP-LJQANCHMSA-N 1-[(2r)-2-[[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]piperidin-1-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CSC=4)=CC=3)=C12 NRMFKTJVFAJMNP-LJQANCHMSA-N 0.000 claims 1
- AESKUPWTDDMLAL-HXUWFJFHSA-N 1-[(2r)-2-[[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CSC=4)=CC=3)=C12 AESKUPWTDDMLAL-HXUWFJFHSA-N 0.000 claims 1
- COAXYQWUTMVSGV-GOSISDBHSA-N 1-[(2r)-2-[[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CSC=4)=CC=3)=C12 COAXYQWUTMVSGV-GOSISDBHSA-N 0.000 claims 1
- CAWSFQAXKDLSJL-LJQANCHMSA-N 1-[(2r)-2-[[4-[3-chloro-4-(1,3-thiazol-5-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4SC=NC=4)=CC=3)=C12 CAWSFQAXKDLSJL-LJQANCHMSA-N 0.000 claims 1
- OZACVFLDNVJDRR-QGZVFWFLSA-N 1-[(2r)-2-[[4-[3-chloro-4-(1,3-thiazol-5-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4SC=NC=4)=CC=3)=C12 OZACVFLDNVJDRR-QGZVFWFLSA-N 0.000 claims 1
- MOMRGTMRWDEZEU-LJQANCHMSA-N 1-[(2r)-2-[[4-[3-chloro-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound C1=NC(C)=CC=C1OC(C(=C1)Cl)=CC=C1NC1=NC=NC2=CC=CC(OC[C@@H]3N(CCC3)C(=O)CO)=C12 MOMRGTMRWDEZEU-LJQANCHMSA-N 0.000 claims 1
- LRAPEKHOZHDIJU-HXUWFJFHSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]piperidin-1-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=NC=4)=CC=3)=C12 LRAPEKHOZHDIJU-HXUWFJFHSA-N 0.000 claims 1
- NTJPTMMEHGYIGG-OAQYLSRUSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=NC=4)=CC=3)=C12 NTJPTMMEHGYIGG-OAQYLSRUSA-N 0.000 claims 1
- GEKBLFUVVXHHJO-LJQANCHMSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=NC=4)=CC=3)=C12 GEKBLFUVVXHHJO-LJQANCHMSA-N 0.000 claims 1
- AJTYKPIFASHILD-OAQYLSRUSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]-4-methylpiperazin-1-yl]-2-hydroxyethanone Chemical compound C1N(C)CCN(C(=O)CO)[C@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 AJTYKPIFASHILD-OAQYLSRUSA-N 0.000 claims 1
- SNLRBQMQODFNMA-JOCHJYFZSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]morpholin-4-yl]-2-(dimethylamino)ethanone Chemical compound C1N(C(=O)CN(C)C)CCO[C@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 SNLRBQMQODFNMA-JOCHJYFZSA-N 0.000 claims 1
- XICURSSTRHKRMG-HXUWFJFHSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]morpholin-4-yl]-2-hydroxyethanone Chemical compound C1N(C(=O)CO)CCO[C@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 XICURSSTRHKRMG-HXUWFJFHSA-N 0.000 claims 1
- MXIWNBPAJCAGDV-HSZRJFAPSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 MXIWNBPAJCAGDV-HSZRJFAPSA-N 0.000 claims 1
- HZIMDINNELHJCL-OAQYLSRUSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]piperidin-1-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 HZIMDINNELHJCL-OAQYLSRUSA-N 0.000 claims 1
- VMXLBDNVEMGARR-JOCHJYFZSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 VMXLBDNVEMGARR-JOCHJYFZSA-N 0.000 claims 1
- OKMRYWPGNVTTAE-JOCHJYFZSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-ethoxyethanone Chemical compound CCOCC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 OKMRYWPGNVTTAE-JOCHJYFZSA-N 0.000 claims 1
- MJBQFBQRZWOFCX-OAQYLSRUSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxy-2-methylpropan-1-one Chemical compound CC(C)(O)C(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 MJBQFBQRZWOFCX-OAQYLSRUSA-N 0.000 claims 1
- FSHWIHXFSFIOAL-HXUWFJFHSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 FSHWIHXFSFIOAL-HXUWFJFHSA-N 0.000 claims 1
- YANDZCHJZKYLGS-OAQYLSRUSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-methoxyethanone Chemical compound COCC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 YANDZCHJZKYLGS-OAQYLSRUSA-N 0.000 claims 1
- ZAESFTGXWHSEJW-XMMPIXPASA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-pyrrolidin-1-ylethanone Chemical compound C([C@@H]1COC=2C=CC=C3N=CN=C(C=23)NC=2C=C(C(=CC=2)OCC=2N=CC=CC=2)Cl)CCN1C(=O)CN1CCCC1 ZAESFTGXWHSEJW-XMMPIXPASA-N 0.000 claims 1
- WRSLJTGCVMSOMP-JOCHJYFZSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-3-hydroxy-2,2-dimethylpropan-1-one Chemical compound OCC(C)(C)C(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 WRSLJTGCVMSOMP-JOCHJYFZSA-N 0.000 claims 1
- ONDHFFYOEGIMFY-OAQYLSRUSA-N 1-[(2r)-2-[[4-[3-chloro-4-[(2-fluorophenyl)methoxy]anilino]quinazolin-5-yl]oxymethyl]piperidin-1-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4C(=CC=CC=4)F)=CC=3)=C12 ONDHFFYOEGIMFY-OAQYLSRUSA-N 0.000 claims 1
- GRYACOOCWFNQOX-OAQYLSRUSA-N 1-[(2r)-2-[[4-[3-chloro-4-[(5-methyl-1,2-oxazol-3-yl)methoxy]anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC4=NOC(C)=C4)=CC=3)=C12 GRYACOOCWFNQOX-OAQYLSRUSA-N 0.000 claims 1
- ZMALQXZDGDQVCT-LJQANCHMSA-N 1-[(2r)-2-[[4-[3-chloro-4-[(5-methyl-1,2-oxazol-3-yl)methoxy]anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound O1C(C)=CC(COC=2C(=CC(NC=3C4=C(OC[C@@H]5N(CCC5)C(=O)CO)C=CC=C4N=CN=3)=CC=2)Cl)=N1 ZMALQXZDGDQVCT-LJQANCHMSA-N 0.000 claims 1
- XEKHJZABXFJLNN-JOCHJYFZSA-N 1-[(2r)-2-[[4-[3-chloro-4-[(6-methylpyridin-2-yl)methoxy]anilino]quinazolin-5-yl]oxymethyl]piperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=CC=CC(COC=2C(=CC(NC=3C4=C(OC[C@@H]5N(CCCC5)C(=O)CO)C=CC=C4N=CN=3)=CC=2)Cl)=N1 XEKHJZABXFJLNN-JOCHJYFZSA-N 0.000 claims 1
- NDWYFHHXBYGFGR-RUZDIDTESA-N 1-[(2r)-2-[[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-pyrrolidin-1-ylethanone Chemical compound C1=NC(C)=CC=C1OC(C(=C1)C)=CC=C1NC1=NC=NC2=CC=CC(OC[C@@H]3N(CCC3)C(=O)CN3CCCC3)=C12 NDWYFHHXBYGFGR-RUZDIDTESA-N 0.000 claims 1
- HWOCTTOWPSPEAG-SFHVURJKSA-N 1-[(2s)-2-[[4-(3-chloro-4-pyridin-3-yloxyanilino)quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCC[C@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OC=4C=NC=CC=4)=CC=3)=C12 HWOCTTOWPSPEAG-SFHVURJKSA-N 0.000 claims 1
- JFWUEJXMZHWXBE-NRFANRHFSA-N 1-[(2s)-2-[[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCCC[C@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CSC=4)=CC=3)=C12 JFWUEJXMZHWXBE-NRFANRHFSA-N 0.000 claims 1
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- RDGPBQJYQGGPTB-UHFFFAOYSA-N 1-[4-[[4-[3-chloro-4-[(6-methylpyridin-2-yl)methoxy]anilino]quinazolin-5-yl]oxymethyl]piperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=CC=CC(COC=2C(=CC(NC=3C4=C(OCC5CCN(CC5)C(=O)CO)C=CC=C4N=CN=3)=CC=2)Cl)=N1 RDGPBQJYQGGPTB-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- OHXWAHWLPJWMBZ-HSZRJFAPSA-N 2-(dimethylamino)-1-[(2r)-2-[[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]ethanone Chemical compound CN(C)CC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(C)C(OC=4C=NC(C)=CC=4)=CC=3)=C12 OHXWAHWLPJWMBZ-HSZRJFAPSA-N 0.000 claims 1
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| 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 |
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| IL144143A0 (en) * | 1999-02-27 | 2002-05-23 | Boehringer Ingelheim Pharma | 4-amino-quinazoline and quinoline derivatives having an inhibitory effect on signal transduction mediated by tyrosine kinases |
| 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 |
| WO2002094790A1 (en) * | 2001-05-23 | 2002-11-28 | Mitsubishi Pharma Corporation | Fused heterocyclic compound and medicinal use thereof |
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| DE60231230D1 (de) * | 2001-11-03 | 2009-04-02 | Astrazeneca Ab | Quinazolin derivate als antitumor-mittel |
| 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 |
| GB0309009D0 (en) * | 2003-04-22 | 2003-05-28 | Astrazeneca Ab | Quinazoline derivatives |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| EP1660479A1 (en) * | 2003-07-29 | 2006-05-31 | Astrazeneca AB | Piperidyl-quinazoline derivatives as tyrosine kinase inhibitors |
| GB0317665D0 (en) * | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| KR20070027487A (ko) * | 2003-09-16 | 2007-03-09 | 아스트라제네카 아베 | 퀴나졸린 유도체 |
| EP1664028A1 (en) * | 2003-09-16 | 2006-06-07 | AstraZeneca AB | Quinazoline derivatives as tyrosine kinase inhibitors |
| BRPI0414489A8 (pt) * | 2003-09-16 | 2019-01-15 | Astrazeneca Ab | derivado de quinazolina, composição farmacêutica, uso de um derivado de quinazolina, e, processo para a preparação de um derivado de quinazolina |
| ATE353888T1 (de) * | 2003-09-19 | 2007-03-15 | Astrazeneca Ab | Chinazolinderivate |
| CA2540008A1 (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 |
| WO2005075439A1 (en) * | 2004-02-03 | 2005-08-18 | Astrazeneca Ab | Quinazoline derivatives |
| CN1993349A (zh) * | 2004-06-04 | 2007-07-04 | 阿斯利康(瑞典)有限公司 | 作为erbb受体酪氨酸激酶的喹唑啉衍生物 |
-
2003
- 2003-09-16 GB GBGB0321648.8A patent/GB0321648D0/en not_active Ceased
-
2004
- 2004-09-14 JP JP2006526685A patent/JP2007505874A/ja active Pending
- 2004-09-14 MX MXPA06002965A patent/MXPA06002965A/es unknown
- 2004-09-14 AU AU2004272351A patent/AU2004272351A1/en not_active Abandoned
- 2004-09-14 EP EP04768482A patent/EP1664029B1/en not_active Expired - Lifetime
- 2004-09-14 BR BRPI0414486-4A patent/BRPI0414486A/pt not_active Application Discontinuation
- 2004-09-14 DE DE602004024420T patent/DE602004024420D1/de not_active Expired - Lifetime
- 2004-09-14 WO PCT/GB2004/003936 patent/WO2005026152A1/en not_active Ceased
- 2004-09-14 US US10/572,262 patent/US20070015743A1/en not_active Abandoned
- 2004-09-14 CA CA002539024A patent/CA2539024A1/en not_active Abandoned
- 2004-09-14 CN CNA2004800335283A patent/CN1882572A/zh active Pending
- 2004-09-14 AT AT04768482T patent/ATE450528T1/de not_active IP Right Cessation
- 2004-09-16 TW TW093128079A patent/TW200526628A/zh unknown
- 2004-09-16 AR ARP040103319A patent/AR045752A1/es unknown
-
2006
- 2006-03-12 IL IL174260A patent/IL174260A0/en unknown
- 2006-03-15 ZA ZA200602189A patent/ZA200602189B/en unknown
- 2006-03-23 NO NO20061320A patent/NO20061320L/no not_active Application Discontinuation
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