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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- XPVHOQPPDWWNCT-JOCHJYFZSA-N 2-hydroxy-1-[(2r)-2-[[4-[3-methyl-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]ethanone Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(C)=CC=1NC(C=12)=NC=NC2=CC=CC=1OC[C@H]1CCCN1C(=O)CO XPVHOQPPDWWNCT-JOCHJYFZSA-N 0.000 claims 1
- XETYECRKJMCQOH-OAQYLSRUSA-N 2-hydroxy-1-[(2r)-2-[[4-[3-methyl-4-[(5-methyl-1,2-oxazol-3-yl)methoxy]anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]ethanone 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)C)=N1 XETYECRKJMCQOH-OAQYLSRUSA-N 0.000 claims 1
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| PCT/GB2004/003936 WO2005026152A1 (en) | 2003-09-16 | 2004-09-14 | Quinazoline derivatives as antitumor agents |
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| 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 |
| ATE395346T1 (de) * | 2003-09-16 | 2008-05-15 | Astrazeneca Ab | Chinazolinderivate als tyrosinkinaseinhibitoren |
| US20070032508A1 (en) * | 2003-09-16 | 2007-02-08 | Bradbury Robert H | Quinazoline derivatives as tyrosine kinase inhibitors |
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| GB0326459D0 (en) | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| ES2315834T3 (es) * | 2004-02-03 | 2009-04-01 | Astrazeneca Ab | Derivados de quinazolina. |
| CA2567832A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as erbb receptor tyrosine kinases |
| US7947676B2 (en) * | 2004-12-14 | 2011-05-24 | Astrazeneca Ab | Pyrazolo[3,4-d]pyrimidine compounds as antitumor agents |
| GB0504474D0 (en) * | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
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| GB0508717D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| KR20080027253A (ko) * | 2005-06-16 | 2008-03-26 | 미리어드 제네틱스, 인크. | 약제학적 조성물 및 이의 용도 |
| DE602006018331D1 (de) * | 2005-09-20 | 2010-12-30 | Astrazeneca Ab | 4-(1h-indazol-5-ylamino)chinazolinverbindungen als inhibitoren der erbb-rezeptortyrosinkinase zur behandlung von krebs |
| EP1940825A1 (en) * | 2005-09-20 | 2008-07-09 | Astra Zeneca AB | Quinazoline derivatives as anticancer agents |
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| US20090029968A1 (en) * | 2005-12-02 | 2009-01-29 | Bernard Christophe Barlaam | Quinazoline derivatives used as inhibitors of erbb tyrosine kinase |
| US20100222344A1 (en) * | 2005-12-02 | 2010-09-02 | Astrazeneca Ab | 4-anilino-substituted quinazoline derivatives as tyrosine kinase inhibitors |
| 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 |
| EA200901041A1 (ru) | 2007-02-06 | 2010-02-26 | Бёрингер Ингельхайм Интернациональ Гмбх | Бициклические гетероциклы, содержащие эти соединения лекарственные средства, их применение и способ их получения |
| WO2008124828A1 (en) * | 2007-04-10 | 2008-10-16 | Myriad Genetics, Inc. | Methods for treating vascular disruption disorders |
| NZ580868A (en) * | 2007-04-10 | 2011-07-29 | Myriad Pharmaceuticals Inc | Dosages and methods for the treatment of cancer |
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| JP2010523696A (ja) * | 2007-04-10 | 2010-07-15 | ミリアド ファーマシューティカルズ， インコーポレイテッド | 脳腫瘍を治療する方法 |
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| PL2245026T3 (pl) | 2008-02-07 | 2013-01-31 | Boehringer Ingelheim Int | Spirocykliczne heterocykle, leki zawierające te związki, ich zastosowanie i sposób ich produkcji |
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| JP5539351B2 (ja) | 2008-08-08 | 2014-07-02 | 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 | シクロヘキシルオキシ置換ヘテロ環、これらの化合物を含有する医薬、およびそれらを生成するための方法 |
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| WO2013056108A2 (en) | 2011-10-14 | 2013-04-18 | Array Biopharma Inc. | Solid dispersion |
| EP2766363A1 (en) | 2011-10-14 | 2014-08-20 | Array Biopharma, Inc. | Polymorphs of arry-380, a selective herb2 inhibitor and pharmaceutical compositions containing them |
| TWI811358B (zh) * | 2018-05-08 | 2023-08-11 | 大陸商迪哲（江蘇）醫藥股份有限公司 | ＥｒｂＢ受體抑制劑 |
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| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| BRPI0413066A (pt) * | 2003-07-29 | 2006-10-17 | Astrazeneca Ab | derivado de quinazolina, ou um sal farmaceuticamente aceitável, ou um éster farmaceuticamente aceitável do mesmo, da fórmula i, uso e processo para a preparação do mesmo, composto, composição farmacêutica, e, métodos para a produção de um efeito antiproliferativo em um animal de sangue quente, para a prevenção ou tratamento de um tumor, para prover um efeito inibitório de tirosina quinase de egfr seletivo, e para tratar um cáncer em um animal de sangue quente |
| GB0317665D0 (en) * | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
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| 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 |
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| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) * | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
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| CA2567832A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as erbb receptor tyrosine kinases |
-
2003
- 2003-09-16 GB GBGB0321648.8A patent/GB0321648D0/en not_active Ceased
-
2004
- 2004-09-14 DE DE602004024420T patent/DE602004024420D1/de not_active Expired - Lifetime
- 2004-09-14 AT AT04768482T patent/ATE450528T1/de not_active IP Right Cessation
- 2004-09-14 US US10/572,262 patent/US20070015743A1/en not_active Abandoned
- 2004-09-14 AU AU2004272351A patent/AU2004272351A1/en not_active Abandoned
- 2004-09-14 JP JP2006526685A patent/JP2007505874A/ja active Pending
- 2004-09-14 CA CA002539024A patent/CA2539024A1/en not_active Abandoned
- 2004-09-14 EP EP04768482A patent/EP1664029B1/en not_active Expired - Lifetime
- 2004-09-14 MX MXPA06002965A patent/MXPA06002965A/es unknown
- 2004-09-14 BR BRPI0414486-4A patent/BRPI0414486A/pt not_active Application Discontinuation
- 2004-09-14 WO PCT/GB2004/003936 patent/WO2005026152A1/en not_active Ceased
- 2004-09-14 CN CNA2004800335283A patent/CN1882572A/zh active Pending
- 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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