RU2001124816A - Quinazoline derivatives as angiogenesis inhibitors - Google Patents
Quinazoline derivatives as angiogenesis inhibitorsInfo
- Publication number
- RU2001124816A RU2001124816A RU2001124816/14A RU2001124816A RU2001124816A RU 2001124816 A RU2001124816 A RU 2001124816A RU 2001124816/14 A RU2001124816/14 A RU 2001124816/14A RU 2001124816 A RU2001124816 A RU 2001124816A RU 2001124816 A RU2001124816 A RU 2001124816A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- yloxy
- quinazoline
- methoxy
- hydroxy
- Prior art date
Links
- 239000004037 angiogenesis inhibitor Substances 0.000 title 1
- 229940121369 angiogenesis inhibitors Drugs 0.000 title 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 307
- 229910052739 hydrogen Inorganic materials 0.000 claims 64
- 239000001257 hydrogen Substances 0.000 claims 64
- 229910052757 nitrogen Inorganic materials 0.000 claims 61
- 125000003545 alkoxy group Chemical group 0.000 claims 60
- 150000002431 hydrogen Chemical class 0.000 claims 54
- 150000001875 compounds Chemical class 0.000 claims 44
- -1 hydroxy, fluoro, amino Chemical group 0.000 claims 44
- 125000001424 substituent group Chemical group 0.000 claims 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 39
- 229910052736 halogen Inorganic materials 0.000 claims 36
- 150000002367 halogens Chemical class 0.000 claims 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 34
- 125000003342 alkenyl group Chemical group 0.000 claims 30
- 125000000304 alkynyl group Chemical group 0.000 claims 29
- 125000000623 heterocyclic group Chemical group 0.000 claims 28
- 125000003282 alkyl amino group Chemical group 0.000 claims 27
- 125000004043 oxo group Chemical group O=* 0.000 claims 26
- 125000005842 heteroatoms Chemical group 0.000 claims 25
- 229910052760 oxygen Inorganic materials 0.000 claims 25
- 229910052717 sulfur Inorganic materials 0.000 claims 25
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims 22
- 150000003839 salts Chemical compound 0.000 claims 22
- 239000011780 sodium chloride Substances 0.000 claims 22
- 125000004122 cyclic group Chemical group 0.000 claims 20
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 17
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 14
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 13
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 125000004193 piperazinyl group Chemical group 0.000 claims 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 12
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 11
- 125000002393 azetidinyl group Chemical group 0.000 claims 11
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 10
- 125000004103 aminoalkyl group Chemical group 0.000 claims 10
- 125000004432 carbon atoms Chemical group C* 0.000 claims 10
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 10
- 125000003386 piperidinyl group Chemical group 0.000 claims 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- AQYSYJUIMQTRMV-UHFFFAOYSA-N Hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 7
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000003277 amino group Chemical compound 0.000 claims 5
- RMRFFCXPLWYOOY-UHFFFAOYSA-N Allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 4
- 125000004423 acyloxy group Chemical group 0.000 claims 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims 4
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- 125000005505 thiomorpholino group Chemical group 0.000 claims 4
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 3
- 230000001772 anti-angiogenic Effects 0.000 claims 3
- 230000002137 anti-vascular Effects 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 3
- CAINZODQISJWSP-GOSISDBHSA-N (2R)-1-[4-(1H-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxy-3-piperidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C=CNC4=CC=3)=C2C=C1OC)N1CCCCC1 CAINZODQISJWSP-GOSISDBHSA-N 0.000 claims 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- KYZNICPMZHBROC-UHFFFAOYSA-N 4-fluoro-1H-indol-5-ol Chemical compound OC1=CC=C2NC=CC2=C1F KYZNICPMZHBROC-UHFFFAOYSA-N 0.000 claims 2
- UMWRMOYYUHIPDT-UHFFFAOYSA-N 4-fluoro-2-methyl-1H-indol-5-ol Chemical compound OC1=CC=C2NC(C)=CC2=C1F UMWRMOYYUHIPDT-UHFFFAOYSA-N 0.000 claims 2
- XQJHCCZRXUOIGW-UHFFFAOYSA-N 6-fluoro-1H-indol-5-ol Chemical compound C1=C(F)C(O)=CC2=C1NC=C2 XQJHCCZRXUOIGW-UHFFFAOYSA-N 0.000 claims 2
- GCAVJDUGKMXYET-UHFFFAOYSA-N 6-fluoro-2-methyl-1H-indol-5-ol Chemical compound OC1=C(F)C=C2NC(C)=CC2=C1 GCAVJDUGKMXYET-UHFFFAOYSA-N 0.000 claims 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N Quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 2
- 125000004848 alkoxyethyl group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 125000000466 oxiranyl group Chemical group 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- AJTCPFPFRHDRSS-QGZVFWFLSA-N (2R)-1-[4-(1H-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxy-3-morpholin-4-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C=CNC4=CC=3)=C2C=C1OC)N1CCOCC1 AJTCPFPFRHDRSS-QGZVFWFLSA-N 0.000 claims 1
- RGMVLDOREVSNEH-QGZVFWFLSA-N (2R)-1-[4-(1H-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxy-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C=CNC4=CC=3)=C2C=C1OC)N1CCCC1 RGMVLDOREVSNEH-QGZVFWFLSA-N 0.000 claims 1
- GCABIYVOJWRUBO-MRXNPFEDSA-N (2R)-1-[4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazolin-7-yl]oxy-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C(=C4C=C(C)NC4=CC=3)F)=C2C=C1OC)N1CCCC1 GCABIYVOJWRUBO-MRXNPFEDSA-N 0.000 claims 1
- TUBBLPAJFHZIKS-HXUWFJFHSA-N (2R)-1-[6-methoxy-2-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-piperidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC(OC=3C=C4C=C(C)NC4=CC=3)=NC=C2C=C1OC)N1CCCCC1 TUBBLPAJFHZIKS-HXUWFJFHSA-N 0.000 claims 1
- BOYNTSOFXPSPNM-LJQANCHMSA-N (2R)-1-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-(4-methylpiperazin-1-yl)propan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C=C(C)NC4=CC=3)=C2C=C1OC)N1CCN(C)CC1 BOYNTSOFXPSPNM-LJQANCHMSA-N 0.000 claims 1
- RMLKLTNSQXPRTB-GOSISDBHSA-N (2R)-1-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C=C(C)NC4=CC=3)=C2C=C1OC)N1CCCC1 RMLKLTNSQXPRTB-GOSISDBHSA-N 0.000 claims 1
- RCAIAVOQSMMUJK-GOSISDBHSA-N (2R)-1-[6-methoxy-4-[(3-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-piperidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C(C)=CNC4=CC=3)=C2C=C1OC)N1CCCCC1 RCAIAVOQSMMUJK-GOSISDBHSA-N 0.000 claims 1
- GAULSWVAQXWTPO-QGZVFWFLSA-N (2R)-1-[6-methoxy-4-[(3-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C(C)=CNC4=CC=3)=C2C=C1OC)N1CCCC1 GAULSWVAQXWTPO-QGZVFWFLSA-N 0.000 claims 1
- HTFFQNJXXVAJCF-LJQANCHMSA-N (2R)-1-[di(propan-2-yl)amino]-3-[4-(1H-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxypropan-2-ol Chemical compound C1=C2NC=CC2=CC(OC2=C3C=C(C(=CC3=NC=N2)OC[C@H](O)CN(C(C)C)C(C)C)OC)=C1 HTFFQNJXXVAJCF-LJQANCHMSA-N 0.000 claims 1
- TUBBLPAJFHZIKS-FQEVSTJZSA-N (2S)-1-[6-methoxy-2-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-piperidin-1-ylpropan-2-ol Chemical compound C([C@H](O)COC1=CC2=NC(OC=3C=C4C=C(C)NC4=CC=3)=NC=C2C=C1OC)N1CCCCC1 TUBBLPAJFHZIKS-FQEVSTJZSA-N 0.000 claims 1
- JEHHXBXKFYXWMT-OAHLLOKOSA-N (5R)-5-[[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxymethyl]pyrrolidin-2-one Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OC[C@H]1CCC(=O)N1 JEHHXBXKFYXWMT-OAHLLOKOSA-N 0.000 claims 1
- YAWIAVFCBGTFIS-UHFFFAOYSA-N 1-(diethylamino)-3-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxypropan-2-ol Chemical compound C1=C2NC(C)=CC2=CC(OC=2N=CN=C3C=C(C(=CC3=2)OC)OCC(O)CN(CC)CC)=C1 YAWIAVFCBGTFIS-UHFFFAOYSA-N 0.000 claims 1
- BOYNTSOFXPSPNM-UHFFFAOYSA-N 1-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-(4-methylpiperazin-1-yl)propan-2-ol Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCC(O)CN1CCN(C)CC1 BOYNTSOFXPSPNM-UHFFFAOYSA-N 0.000 claims 1
- NCVLOJJBTMDBMS-UHFFFAOYSA-N 1-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=C2NC(C)=CC2=CC(OC2=C3C=C(C(=CC3=NC=N2)OCC(O)CNC(C)C)OC)=C1 NCVLOJJBTMDBMS-UHFFFAOYSA-N 0.000 claims 1
- GFJOCFYAAVCNRB-UHFFFAOYSA-N 1-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-morpholin-4-ylpropan-2-ol Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCC(O)CN1CCOCC1 GFJOCFYAAVCNRB-UHFFFAOYSA-N 0.000 claims 1
- KGVZGCARCFJSCR-UHFFFAOYSA-N 1-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-piperidin-1-ylpropan-2-ol Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCC(O)CN1CCCCC1 KGVZGCARCFJSCR-UHFFFAOYSA-N 0.000 claims 1
- RMLKLTNSQXPRTB-UHFFFAOYSA-N 1-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-pyrrolidin-1-ylpropan-2-ol Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCC(O)CN1CCCC1 RMLKLTNSQXPRTB-UHFFFAOYSA-N 0.000 claims 1
- MYDKUTLLQONJKD-UHFFFAOYSA-N 2-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxy-N-methylethanamine Chemical compound C1=C2NC(C)=CC2=CC(OC=2N=CN=C3C=C(C(=CC3=2)OC)OCCNC)=C1 MYDKUTLLQONJKD-UHFFFAOYSA-N 0.000 claims 1
- QUTFAZLYDDGVLH-UHFFFAOYSA-N 3-[4-(1H-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxy-N,N-dimethylpropan-1-amine Chemical compound C1=C2NC=CC2=CC(OC2=C3C=C(C(=CC3=NC=N2)OCCCN(C)C)OC)=C1 QUTFAZLYDDGVLH-UHFFFAOYSA-N 0.000 claims 1
- APUJNJMMOVJBMQ-UHFFFAOYSA-N 3-[4-[(2,3-dimethyl-1H-indol-5-yl)oxy]-6-methoxyquinazolin-7-yl]oxy-N,N-dimethylpropan-1-amine Chemical compound C1=C2NC(C)=C(C)C2=CC(OC2=C3C=C(C(=CC3=NC=N2)OCCCN(C)C)OC)=C1 APUJNJMMOVJBMQ-UHFFFAOYSA-N 0.000 claims 1
- KSYZTLBEZNPWQB-UHFFFAOYSA-N 3-[4-[2-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxyethoxy]piperidin-1-yl]propanenitrile Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCOC1CCN(CCC#N)CC1 KSYZTLBEZNPWQB-UHFFFAOYSA-N 0.000 claims 1
- SSPGYVCKWTUTSX-UHFFFAOYSA-N 3-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-piperidin-4-ylpropanenitrile Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OC(CC#N)C1CCNCC1 SSPGYVCKWTUTSX-UHFFFAOYSA-N 0.000 claims 1
- ZHWIBBNQOOPMAE-UHFFFAOYSA-N 4-(1H-indol-5-yloxy)-6-methoxy-7-(2-piperidin-1-ylethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCN1CCCCC1 ZHWIBBNQOOPMAE-UHFFFAOYSA-N 0.000 claims 1
- MEBAXCQMZHDHLI-UHFFFAOYSA-N 4-(1H-indol-5-yloxy)-6-methoxy-7-(2-piperidin-2-ylethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCC1CCCCN1 MEBAXCQMZHDHLI-UHFFFAOYSA-N 0.000 claims 1
- IFQGZDCTCSXUNK-UHFFFAOYSA-N 4-(1H-indol-5-yloxy)-6-methoxy-7-(2-pyridin-4-yloxyethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCOC1=CC=NC=C1 IFQGZDCTCSXUNK-UHFFFAOYSA-N 0.000 claims 1
- YUHFKJWRLSLBBH-UHFFFAOYSA-N 4-(1H-indol-5-yloxy)-6-methoxy-7-(3-methylsulfonylpropoxy)quinazoline Chemical compound C1=C2NC=CC2=CC(OC2=C3C=C(C(=CC3=NC=N2)OCCCS(C)(=O)=O)OC)=C1 YUHFKJWRLSLBBH-UHFFFAOYSA-N 0.000 claims 1
- ZQARCLVLXXXKJF-UHFFFAOYSA-N 4-(1H-indol-5-yloxy)-6-methoxy-7-(3-piperidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCCN1CCCCC1 ZQARCLVLXXXKJF-UHFFFAOYSA-N 0.000 claims 1
- JJFONHXJKBVBHW-UHFFFAOYSA-N 4-(1H-indol-5-yloxy)-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCCN1CCCC1 JJFONHXJKBVBHW-UHFFFAOYSA-N 0.000 claims 1
- GHAQVSSERMFIOD-UHFFFAOYSA-N 4-(1H-indol-5-yloxy)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCC1CCN(C)CC1 GHAQVSSERMFIOD-UHFFFAOYSA-N 0.000 claims 1
- FDGLZZQHPXHDGZ-UHFFFAOYSA-N 4-(1H-indol-5-yloxy)-6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]quinazoline Chemical compound C1=C2NC=CC2=CC(OC=2N=CN=C3C=C(C(=CC3=2)OC)OCCOCCOC)=C1 FDGLZZQHPXHDGZ-UHFFFAOYSA-N 0.000 claims 1
- DQNUKKHSBRKMTN-UHFFFAOYSA-N 4-(1H-indol-6-yloxy)-6-methoxy-7-(3-piperidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4NC=CC4=CC=3)N=CN=C2C=C1OCCCN1CCCCC1 DQNUKKHSBRKMTN-UHFFFAOYSA-N 0.000 claims 1
- WEXBUAHOJKVQNZ-UHFFFAOYSA-N 4-(3-fluoroquinolin-7-yl)oxy-6-methoxy-7-(3-piperidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4N=CC(F)=CC4=CC=3)N=CN=C2C=C1OCCCN1CCCCC1 WEXBUAHOJKVQNZ-UHFFFAOYSA-N 0.000 claims 1
- XNENFRLEEFRRCB-UHFFFAOYSA-N 4-(3-fluoroquinolin-7-yl)oxy-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4N=CC(F)=CC4=CC=3)N=CN=C2C=C1OCCCN1CCCC1 XNENFRLEEFRRCB-UHFFFAOYSA-N 0.000 claims 1
- QXMBFDNIAYVLFK-UHFFFAOYSA-N 4-[(2,3-dimethyl-1H-indol-5-yl)oxy]-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C(C)=C(C)NC4=CC=3)N=CN=C2C=C1OCCCN1CCCC1 QXMBFDNIAYVLFK-UHFFFAOYSA-N 0.000 claims 1
- CPYOLRZYFGXJMZ-UHFFFAOYSA-N 4-[(2,3-dimethyl-1H-indol-5-yl)oxy]-6-methoxy-7-[(1-methylpiperidin-3-yl)methoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C(C)=C(C)NC4=CC=3)N=CN=C2C=C1OCC1CCCN(C)C1 CPYOLRZYFGXJMZ-UHFFFAOYSA-N 0.000 claims 1
- BYXRJZJEIZSEEJ-UHFFFAOYSA-N 4-[(2,3-dimethyl-1H-indol-5-yl)oxy]-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C(C)=C(C)NC4=CC=3)N=CN=C2C=C1OCC1CCN(C)CC1 BYXRJZJEIZSEEJ-UHFFFAOYSA-N 0.000 claims 1
- SUANGBBIESOPQK-UHFFFAOYSA-N 4-[(2-methyl-1H-indol-5-yl)oxy]-7-(2-piperidin-1-ylethoxy)quinazoline Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCCN1CCCCC1 SUANGBBIESOPQK-UHFFFAOYSA-N 0.000 claims 1
- VBYBNMXKSTZHGU-UHFFFAOYSA-N 4-[(2-methyl-1H-indol-5-yl)oxy]-7-(3-methylsulfonylpropoxy)quinazoline Chemical compound CS(=O)(=O)CCCOC1=CC=C2C(OC=3C=C4C=C(NC4=CC=3)C)=NC=NC2=C1 VBYBNMXKSTZHGU-UHFFFAOYSA-N 0.000 claims 1
- KFPBKESUJSJWGU-UHFFFAOYSA-N 4-[(2-methyl-1H-indol-5-yl)oxy]-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCCCN1CCCC1 KFPBKESUJSJWGU-UHFFFAOYSA-N 0.000 claims 1
- RATKYOYWLZOLNN-UHFFFAOYSA-N 4-[(2-methyl-1H-indol-5-yl)oxy]-7-(piperidin-4-ylmethoxy)quinazoline Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCC1CCNCC1 RATKYOYWLZOLNN-UHFFFAOYSA-N 0.000 claims 1
- MKAMATMVKCLDIG-UHFFFAOYSA-N 4-[(2-methyl-1H-indol-5-yl)oxy]-7-[2-(1,2,4-triazol-1-yl)ethoxy]quinazoline Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCCN1C=NC=N1 MKAMATMVKCLDIG-UHFFFAOYSA-N 0.000 claims 1
- LBHIBGICIXQVKN-UHFFFAOYSA-N 4-[(4-bromo-1H-indol-5-yl)oxy]-6-methoxy-7-(3-piperidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=CNC4=CC=3)Br)N=CN=C2C=C1OCCCN1CCCCC1 LBHIBGICIXQVKN-UHFFFAOYSA-N 0.000 claims 1
- UCNZLDYJJUFVBL-UHFFFAOYSA-N 4-[(4-fluoro-1H-indol-5-yl)oxy]-6-methoxy-7-(3-piperidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=CNC4=CC=3)F)N=CN=C2C=C1OCCCN1CCCCC1 UCNZLDYJJUFVBL-UHFFFAOYSA-N 0.000 claims 1
- YAIZIOMJNQKWHW-UHFFFAOYSA-N 4-[(4-fluoro-1H-indol-5-yl)oxy]-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=CNC4=CC=3)F)N=CN=C2C=C1OCCCN1CCCC1 YAIZIOMJNQKWHW-UHFFFAOYSA-N 0.000 claims 1
- QLKYLLNKQLYUCK-UHFFFAOYSA-N 4-[(4-fluoro-1H-indol-5-yl)oxy]-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=CNC4=CC=3)F)N=CN=C2C=C1OCC1CCN(C)CC1 QLKYLLNKQLYUCK-UHFFFAOYSA-N 0.000 claims 1
- QIAQSHWCWZYWDB-UHFFFAOYSA-N 4-[(4-fluoro-1H-indol-5-yl)oxy]-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=CNC4=CC=3)F)N=CN=C2C=C1OCCC1CCN(C)CC1 QIAQSHWCWZYWDB-UHFFFAOYSA-N 0.000 claims 1
- OWHNSMAGPUBAHX-UHFFFAOYSA-N 4-[(4-fluoro-1H-indol-5-yl)oxy]-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=CNC4=CC=3)F)N=CN=C2C=C1OCCCN1CCN(C)CC1 OWHNSMAGPUBAHX-UHFFFAOYSA-N 0.000 claims 1
- NZMWZMBJACHTSF-UHFFFAOYSA-N 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(3-piperidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=C(C)NC4=CC=3)F)N=CN=C2C=C1OCCCN1CCCCC1 NZMWZMBJACHTSF-UHFFFAOYSA-N 0.000 claims 1
- XXJWYDDUDKYVKI-UHFFFAOYSA-N 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=C(C)NC4=CC=3)F)N=CN=C2C=C1OCCCN1CCCC1 XXJWYDDUDKYVKI-UHFFFAOYSA-N 0.000 claims 1
- XWOGDYNDOQKNBW-UHFFFAOYSA-N 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=C(C)NC4=CC=3)F)N=CN=C2C=C1OCC1CCN(C)CC1 XWOGDYNDOQKNBW-UHFFFAOYSA-N 0.000 claims 1
- WKHMXMYWJGLMDQ-UHFFFAOYSA-N 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=C(C)NC4=CC=3)F)N=CN=C2C=C1OCCC1CCN(C)CC1 WKHMXMYWJGLMDQ-UHFFFAOYSA-N 0.000 claims 1
- CUXRYZZQLQTALS-UHFFFAOYSA-N 4-[(6-fluoro-1H-indol-5-yl)oxy]-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C(=CC=4NC=CC=4C=3)F)N=CN=C2C=C1OCCCN1CCCC1 CUXRYZZQLQTALS-UHFFFAOYSA-N 0.000 claims 1
- OJHJHQYEKVWLHP-UHFFFAOYSA-N 4-[(6-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C(=CC=4NC(C)=CC=4C=3)F)N=CN=C2C=C1OCCCN1CCCC1 OJHJHQYEKVWLHP-UHFFFAOYSA-N 0.000 claims 1
- QFKOPMYWROWEFC-UHFFFAOYSA-N 4-[2-[2-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxyethoxy]ethyl]morpholine Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCOCCN1CCOCC1 QFKOPMYWROWEFC-UHFFFAOYSA-N 0.000 claims 1
- OURIIRUUFMGNNP-UHFFFAOYSA-N 4-[2-[4-[[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxymethyl]piperidin-1-yl]ethyl]morpholine Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCC(CC1)CCN1CCN1CCOCC1 OURIIRUUFMGNNP-UHFFFAOYSA-N 0.000 claims 1
- AUEYCHJTTCJDQE-UHFFFAOYSA-N 4-[2-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxyethyl]morpholine Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCN1CCOCC1 AUEYCHJTTCJDQE-UHFFFAOYSA-N 0.000 claims 1
- PLNBQVBLDZSFCI-UHFFFAOYSA-N 4-[3-(6-methoxy-4-quinolin-7-yloxyquinazolin-7-yl)oxypropyl]-1,4-thiazinane 1,1-dioxide Chemical compound COC1=CC2=C(OC=3C=C4N=CC=CC4=CC=3)N=CN=C2C=C1OCCCN1CCS(=O)(=O)CC1 PLNBQVBLDZSFCI-UHFFFAOYSA-N 0.000 claims 1
- MTIRLVIGOZBETB-UHFFFAOYSA-N 4-[3-(6-methoxy-4-quinolin-7-yloxyquinazolin-7-yl)oxypropyl]morpholine Chemical compound COC1=CC2=C(OC=3C=C4N=CC=CC4=CC=3)N=CN=C2C=C1OCCCN1CCOCC1 MTIRLVIGOZBETB-UHFFFAOYSA-N 0.000 claims 1
- KGXQAPJRCBHUKG-UHFFFAOYSA-N 4-[3-[4-(1H-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxypropyl]-1,4-thiazinane 1,1-dioxide Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCCN1CCS(=O)(=O)CC1 KGXQAPJRCBHUKG-UHFFFAOYSA-N 0.000 claims 1
- SDBHMCYMOMGNFX-UHFFFAOYSA-N 4-[3-[4-(1H-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxypropyl]morpholine Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCCN1CCOCC1 SDBHMCYMOMGNFX-UHFFFAOYSA-N 0.000 claims 1
- KCVMXGBFTUIXQZ-UHFFFAOYSA-N 4-[3-[4-(1H-indol-6-yloxy)-6-methoxyquinazolin-7-yl]oxypropyl]morpholine Chemical compound COC1=CC2=C(OC=3C=C4NC=CC4=CC=3)N=CN=C2C=C1OCCCN1CCOCC1 KCVMXGBFTUIXQZ-UHFFFAOYSA-N 0.000 claims 1
- OGGVFXMSCQVORR-UHFFFAOYSA-N 4-[3-[4-(4-chloroquinolin-7-yl)oxy-6-methoxyquinazolin-7-yl]oxypropyl]morpholine Chemical compound COC1=CC2=C(OC=3C=C4N=CC=C(Cl)C4=CC=3)N=CN=C2C=C1OCCCN1CCOCC1 OGGVFXMSCQVORR-UHFFFAOYSA-N 0.000 claims 1
- GGRMMRBLTOWVPK-UHFFFAOYSA-N 4-[3-[4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxypropyl]-1,4-thiazinane 1,1-dioxide Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCCCN1CCS(=O)(=O)CC1 GGRMMRBLTOWVPK-UHFFFAOYSA-N 0.000 claims 1
- XSDHPUDCUTXDOC-UHFFFAOYSA-N 4-[3-[4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxypropyl]morpholine Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCCCN1CCOCC1 XSDHPUDCUTXDOC-UHFFFAOYSA-N 0.000 claims 1
- RIYQUDOHNPNEGO-UHFFFAOYSA-N 4-[3-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxypropyl]-1,4-thiazinane 1,1-dioxide Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCCN1CCS(=O)(=O)CC1 RIYQUDOHNPNEGO-UHFFFAOYSA-N 0.000 claims 1
- XACHHHFBHKJFTG-UHFFFAOYSA-N 4-[3-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxypropyl]morpholine Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCCN1CCOCC1 XACHHHFBHKJFTG-UHFFFAOYSA-N 0.000 claims 1
- CKRDGZKPAWDNQJ-UHFFFAOYSA-N 6,7-dimethoxy-4-naphthalen-1-yloxyquinazoline Chemical compound C1=CC=C2C(OC=3N=CN=C4C=C(C(=CC4=3)OC)OC)=CC=CC2=C1 CKRDGZKPAWDNQJ-UHFFFAOYSA-N 0.000 claims 1
- AXILPVOKGYMDFU-UHFFFAOYSA-N 6,7-dimethoxy-4-naphthalen-1-ylsulfanylquinazoline Chemical compound C1=CC=C2C(SC=3N=CN=C4C=C(C(=CC4=3)OC)OC)=CC=CC2=C1 AXILPVOKGYMDFU-UHFFFAOYSA-N 0.000 claims 1
- SHIOLHZTLNTUNT-UHFFFAOYSA-N 6,7-dimethoxy-4-naphthalen-2-yloxyquinazoline Chemical compound C1=CC=CC2=CC(OC=3N=CN=C4C=C(C(=CC4=3)OC)OC)=CC=C21 SHIOLHZTLNTUNT-UHFFFAOYSA-N 0.000 claims 1
- GGZANAKWWFPISZ-UHFFFAOYSA-N 6,7-dimethoxy-4-naphthalen-2-ylsulfanylquinazoline Chemical compound C1=CC=CC2=CC(SC=3N=CN=C4C=C(C(=CC4=3)OC)OC)=CC=C21 GGZANAKWWFPISZ-UHFFFAOYSA-N 0.000 claims 1
- IDJNQPAEAFFNTF-UHFFFAOYSA-N 6-methoxy-4-(4-methylquinolin-7-yl)oxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4N=CC=C(C)C4=CC=3)N=CN=C2C=C1OCCCN1CCCC1 IDJNQPAEAFFNTF-UHFFFAOYSA-N 0.000 claims 1
- JIHDRMRBLXQGCC-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-(2-piperidin-1-ylethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCN1CCCCC1 JIHDRMRBLXQGCC-UHFFFAOYSA-N 0.000 claims 1
- DQEWEZLVYRCMIP-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-(2-piperidin-4-yloxyethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCOC1CCNCC1 DQEWEZLVYRCMIP-UHFFFAOYSA-N 0.000 claims 1
- UPKZMZRKCYFKQM-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-(2-pyridin-4-yloxyethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCOC1=CC=NC=C1 UPKZMZRKCYFKQM-UHFFFAOYSA-N 0.000 claims 1
- XWZDOLXRLQATMB-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-(2-pyrrolidin-1-ylethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCN1CCCC1 XWZDOLXRLQATMB-UHFFFAOYSA-N 0.000 claims 1
- HMKXLULQTFQOTJ-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-(3-methylsulfonylpropoxy)quinazoline Chemical compound C1=C2NC(C)=CC2=CC(OC2=C3C=C(C(=CC3=NC=N2)OCCCS(C)(=O)=O)OC)=C1 HMKXLULQTFQOTJ-UHFFFAOYSA-N 0.000 claims 1
- BMKBXNMTWNYODF-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-(3-piperidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCCN1CCCCC1 BMKBXNMTWNYODF-UHFFFAOYSA-N 0.000 claims 1
- VWIOUOMKJGDTHR-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCCN1CCCC1 VWIOUOMKJGDTHR-UHFFFAOYSA-N 0.000 claims 1
- OTOUXILYJXJWKG-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-(piperidin-4-ylmethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCC1CCNCC1 OTOUXILYJXJWKG-UHFFFAOYSA-N 0.000 claims 1
- PWBWRKIZHIYOEX-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-[(1-methylpiperidin-3-yl)methoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCC1CCCN(C)C1 PWBWRKIZHIYOEX-UHFFFAOYSA-N 0.000 claims 1
- AWIJHWDEWAIVTF-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCC1CCN(C)CC1 AWIJHWDEWAIVTF-UHFFFAOYSA-N 0.000 claims 1
- GBGXDEQXIOILJR-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-[2-(1,2,4-triazol-1-yl)ethoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCN1C=NC=N1 GBGXDEQXIOILJR-UHFFFAOYSA-N 0.000 claims 1
- IWFIXMMBXWYLPM-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-[2-[2-(4-methylpiperazin-1-yl)ethoxy]ethoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCOCCN1CCN(C)CC1 IWFIXMMBXWYLPM-UHFFFAOYSA-N 0.000 claims 1
- WYJRGYROVOJXHG-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-[3-(4-methylpiperazin-1-yl)propoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCCN1CCN(C)CC1 WYJRGYROVOJXHG-UHFFFAOYSA-N 0.000 claims 1
- JLROULFIQSVDDO-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-[[1-(2-pyrrolidin-1-ylethyl)piperidin-4-yl]methoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCC(CC1)CCN1CCN1CCCC1 JLROULFIQSVDDO-UHFFFAOYSA-N 0.000 claims 1
- AJFHRQHLDMJYPV-UHFFFAOYSA-N 6-methoxy-4-[(3-methyl-1H-indol-5-yl)oxy]-7-(3-piperidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C(C)=CNC4=CC=3)N=CN=C2C=C1OCCCN1CCCCC1 AJFHRQHLDMJYPV-UHFFFAOYSA-N 0.000 claims 1
- PXIVXJNSIQJJGV-UHFFFAOYSA-N 6-methoxy-7-(3-piperidin-1-ylpropoxy)-4-[[6-(trifluoromethyl)-1H-indol-5-yl]oxy]quinazoline Chemical compound COC1=CC2=C(OC=3C(=CC=4NC=CC=4C=3)C(F)(F)F)N=CN=C2C=C1OCCCN1CCCCC1 PXIVXJNSIQJJGV-UHFFFAOYSA-N 0.000 claims 1
- FDQIQMGVDKZEMI-UHFFFAOYSA-N 6-methoxy-7-(3-piperidin-1-ylpropoxy)-4-quinolin-7-yloxyquinazoline Chemical compound COC1=CC2=C(OC=3C=C4N=CC=CC4=CC=3)N=CN=C2C=C1OCCCN1CCCCC1 FDQIQMGVDKZEMI-UHFFFAOYSA-N 0.000 claims 1
- XVERRHVZSLWUFT-UHFFFAOYSA-N 6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)-4-[[2-(trifluoromethyl)-1H-indol-5-yl]oxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(NC4=CC=3)C(F)(F)F)N=CN=C2C=C1OCCCN1CCCC1 XVERRHVZSLWUFT-UHFFFAOYSA-N 0.000 claims 1
- LLEKBLGYIYIZGY-UHFFFAOYSA-N 6-methoxy-7-[(1-methylpiperidin-3-yl)methoxy]-4-quinolin-7-yloxyquinazoline Chemical compound COC1=CC2=C(OC=3C=C4N=CC=CC4=CC=3)N=CN=C2C=C1OCC1CCCN(C)C1 LLEKBLGYIYIZGY-UHFFFAOYSA-N 0.000 claims 1
- GJNCFYVBXCUDNX-UHFFFAOYSA-N 6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]-4-(4-methylquinolin-7-yl)oxyquinazoline Chemical compound COC1=CC2=C(OC=3C=C4N=CC=C(C)C4=CC=3)N=CN=C2C=C1OCC1CCN(C)CC1 GJNCFYVBXCUDNX-UHFFFAOYSA-N 0.000 claims 1
- PEKIYYDHDJIMAB-UHFFFAOYSA-N 6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]-4-[[2-(trifluoromethyl)-1H-indol-5-yl]oxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(NC4=CC=3)C(F)(F)F)N=CN=C2C=C1OCC1CCN(C)CC1 PEKIYYDHDJIMAB-UHFFFAOYSA-N 0.000 claims 1
- GIRSQICOEKYBIB-UHFFFAOYSA-N 6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]-4-naphthalen-2-yloxyquinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CC=CC4=CC=3)N=CN=C2C=C1OCC1CCN(C)CC1 GIRSQICOEKYBIB-UHFFFAOYSA-N 0.000 claims 1
- ZCFBUMNTQJWXDH-UHFFFAOYSA-N 6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]-4-quinolin-7-yloxyquinazoline Chemical compound COC1=CC2=C(OC=3C=C4N=CC=CC4=CC=3)N=CN=C2C=C1OCC1CCN(C)CC1 ZCFBUMNTQJWXDH-UHFFFAOYSA-N 0.000 claims 1
- CXYGHMXUYKGXHL-UHFFFAOYSA-N 6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]-4-[(2-methyl-1H-indol-5-yl)oxy]quinazoline Chemical compound C1=C2NC(C)=CC2=CC(OC=2N=CN=C3C=C(C(=CC3=2)OC)OCCOCCOC)=C1 CXYGHMXUYKGXHL-UHFFFAOYSA-N 0.000 claims 1
- BMIUIVQIHYOKBO-UHFFFAOYSA-N 6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]-4-quinolin-7-yloxyquinazoline Chemical compound C1=CC=NC2=CC(OC=3N=CN=C4C=C(C(=CC4=3)OC)OCCOCCOC)=CC=C21 BMIUIVQIHYOKBO-UHFFFAOYSA-N 0.000 claims 1
- WHDADEZKOPIUDJ-UHFFFAOYSA-N 6-methoxy-7-[2-[1-(2-methoxyethyl)piperidin-4-yl]ethoxy]-4-[(2-methyl-1H-indol-5-yl)oxy]quinazoline Chemical compound C1CN(CCOC)CCC1CCOC1=CC2=NC=NC(OC=3C=C4C=C(C)NC4=CC=3)=C2C=C1OC WHDADEZKOPIUDJ-UHFFFAOYSA-N 0.000 claims 1
- YNIYIXLTDOQPBV-UHFFFAOYSA-N 6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]-4-quinolin-7-yloxyquinazoline Chemical compound COC1=CC2=C(OC=3C=C4N=CC=CC4=CC=3)N=CN=C2C=C1OCCCN1CCN(C)CC1 YNIYIXLTDOQPBV-UHFFFAOYSA-N 0.000 claims 1
- HVFDRYRGNKCISB-UHFFFAOYSA-N 6-methoxy-7-[[1-(2-methoxyethyl)piperidin-4-yl]methoxy]-4-[(2-methyl-1H-indol-5-yl)oxy]quinazoline Chemical compound C1CN(CCOC)CCC1COC1=CC2=NC=NC(OC=3C=C4C=C(C)NC4=CC=3)=C2C=C1OC HVFDRYRGNKCISB-UHFFFAOYSA-N 0.000 claims 1
- WRVLCINSRDCLKV-UHFFFAOYSA-N 6-methoxy-7-[[1-(2-methylsulfonylethyl)piperidin-4-yl]methoxy]-4-quinolin-7-yloxyquinazoline Chemical compound COC1=CC2=C(OC=3C=C4N=CC=CC4=CC=3)N=CN=C2C=C1OCC1CCN(CCS(C)(=O)=O)CC1 WRVLCINSRDCLKV-UHFFFAOYSA-N 0.000 claims 1
- XXXPJLBUNIPWAR-UHFFFAOYSA-N 7-(3-ethylsulfonylpropoxy)-6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazoline Chemical compound C1=C2NC(C)=CC2=CC(OC=2N=CN=C3C=C(C(=CC3=2)OC)OCCCS(=O)(=O)CC)=C1 XXXPJLBUNIPWAR-UHFFFAOYSA-N 0.000 claims 1
- OPHQEUPKMBICOL-UHFFFAOYSA-N 7-[[1-(2-methoxyethyl)piperidin-4-yl]methoxy]-4-[(2-methyl-1H-indol-5-yl)oxy]quinazoline Chemical compound C1CN(CCOC)CCC1COC1=CC=C(C(OC=2C=C3C=C(C)NC3=CC=2)=NC=N2)C2=C1 OPHQEUPKMBICOL-UHFFFAOYSA-N 0.000 claims 1
- CIRUJMHVOFMJPC-UHFFFAOYSA-N N,N-diethyl-2-[4-(1H-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxyethanamine Chemical compound C1=C2NC=CC2=CC(OC=2N=CN=C3C=C(C(=CC3=2)OC)OCCN(CC)CC)=C1 CIRUJMHVOFMJPC-UHFFFAOYSA-N 0.000 claims 1
- CCOPTYVGCANMMN-UHFFFAOYSA-N N,N-diethyl-2-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxyethanamine Chemical compound C1=C2NC(C)=CC2=CC(OC=2N=CN=C3C=C(C(=CC3=2)OC)OCCN(CC)CC)=C1 CCOPTYVGCANMMN-UHFFFAOYSA-N 0.000 claims 1
- MVROJXXDSHXTMG-UHFFFAOYSA-N N,N-diethyl-3-[4-(1H-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxypropan-1-amine Chemical compound C1=C2NC=CC2=CC(OC=2N=CN=C3C=C(C(=CC3=2)OC)OCCCN(CC)CC)=C1 MVROJXXDSHXTMG-UHFFFAOYSA-N 0.000 claims 1
- QJRZJWVFXKCBQU-UHFFFAOYSA-N N-[2-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxyethyl]-N-methylmethanesulfonamide Chemical compound C1=C2NC(C)=CC2=CC(OC2=C3C=C(C(=CC3=NC=N2)OCCN(C)S(C)(=O)=O)OC)=C1 QJRZJWVFXKCBQU-UHFFFAOYSA-N 0.000 claims 1
- PAWZHBQURJVVMX-UHFFFAOYSA-N N-[2-[6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazolin-7-yl]oxyethyl]-N-methylpyridin-4-amine Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCN(C)C1=CC=NC=C1 PAWZHBQURJVVMX-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004429 atoms Chemical group 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000001590 oxidative Effects 0.000 claims 1
- 239000000546 pharmaceutic aid Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-O piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrugs Drugs 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
Claims (30)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99400305 | 1999-02-10 | ||
EP99400305.1 | 1999-02-10 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU2001124816A true RU2001124816A (en) | 2003-06-20 |
RU2262935C2 RU2262935C2 (en) | 2005-10-27 |
Family
ID=8241873
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2001124816/15A RU2262935C2 (en) | 1999-02-10 | 2000-02-08 | Derivatives of quinazoline as inhibitors of angiogenesis |
Country Status (32)
Country | Link |
---|---|
US (3) | US7074800B1 (en) |
EP (3) | EP1154774B1 (en) |
JP (3) | JP3893026B2 (en) |
KR (2) | KR100838617B1 (en) |
CN (2) | CN100360505C (en) |
AT (2) | ATE298237T1 (en) |
AU (1) | AU763618B2 (en) |
BR (2) | BRPI0008128B8 (en) |
CA (2) | CA2674803C (en) |
CY (1) | CY1110979T1 (en) |
CZ (3) | CZ305827B6 (en) |
DE (2) | DE60020941T2 (en) |
DK (2) | DK1553097T3 (en) |
EE (3) | EE200900039A (en) |
ES (2) | ES2242596T3 (en) |
HK (2) | HK1041212B (en) |
HU (2) | HU230000B1 (en) |
ID (1) | ID30552A (en) |
IL (4) | IL144745A0 (en) |
IS (2) | IS2512B (en) |
MX (1) | MXPA01008182A (en) |
NO (3) | NO321604B1 (en) |
NZ (2) | NZ513204A (en) |
PL (2) | PL199802B1 (en) |
PT (2) | PT1553097E (en) |
RU (1) | RU2262935C2 (en) |
SI (2) | SI1154774T1 (en) |
SK (3) | SK288378B6 (en) |
TR (2) | TR200102314T2 (en) |
UA (1) | UA73932C2 (en) |
WO (1) | WO2000047212A1 (en) |
ZA (1) | ZA200106340B (en) |
Families Citing this family (323)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100360505C (en) * | 1999-02-10 | 2008-01-09 | 阿斯特拉曾尼卡有限公司 | Quinazoline derivatives as angiogenesis inhibitors |
ATE398120T1 (en) | 1999-11-05 | 2008-07-15 | Astrazeneca Ab | NEW QUINAZOLINE DERIVATIVES |
AU2001235804A1 (en) * | 2000-03-06 | 2001-09-17 | Astrazeneca Ab | Therapy |
GB0008269D0 (en) * | 2000-04-05 | 2000-05-24 | Astrazeneca Ab | Combination chemotherapy |
UA73993C2 (en) | 2000-06-06 | 2005-10-17 | Астразенека Аб | Quinazoline derivatives for the treatment of tumours and a pharmaceutical composition |
SK2142003A3 (en) * | 2000-08-21 | 2003-07-01 | Astrazeneca Ab | Quinazoline derivatives, process for their preparation, pharmaceutical composition comprising same and their use |
AU2001292138A1 (en) | 2000-10-13 | 2002-04-22 | Astrazeneca Ab | Quinazoline derivatives with anti-tumour activity |
JP2004511480A (en) | 2000-10-13 | 2004-04-15 | アストラゼネカ アクチボラグ | Quinazoline derivatives |
DE60137273D1 (en) | 2000-10-20 | 2009-02-12 | Eisai R&D Man Co Ltd | Process for the preparation of 4-phenoxyquinoline derivatives |
ATE502928T1 (en) | 2000-11-01 | 2011-04-15 | Millennium Pharm Inc | NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF |
NZ526542A (en) | 2000-12-21 | 2005-01-28 | Glaxo Group Ltd | Pyrimidineamines as angiogenesis modulators |
US6878714B2 (en) | 2001-01-12 | 2005-04-12 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
US6995162B2 (en) * | 2001-01-12 | 2006-02-07 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
US7105682B2 (en) | 2001-01-12 | 2006-09-12 | Amgen Inc. | Substituted amine derivatives and methods of use |
US7102009B2 (en) | 2001-01-12 | 2006-09-05 | Amgen Inc. | Substituted amine derivatives and methods of use |
ATE353889T1 (en) * | 2001-03-23 | 2007-03-15 | Bayer Pharmaceuticals Corp | RHO KINASE INHIBITORS |
DE60211317T2 (en) * | 2001-03-23 | 2007-04-12 | Bayer Corp. | RHO-KINASE INHIBITORS |
EP1381599B1 (en) | 2001-04-19 | 2008-09-24 | Astrazeneca AB | Quinazoline derivatives |
US7132427B2 (en) | 2001-06-21 | 2006-11-07 | Ariad Pharmaceuticals, Inc. | Quinazolines and uses thereof |
ATE341545T1 (en) * | 2001-07-16 | 2006-10-15 | Astrazeneca Ab | QUINOLINE DERIVATIVES AND THEIR USE AS TYROSINE KINASE INHIBITORS |
GB0128109D0 (en) * | 2001-11-23 | 2002-01-16 | Astrazeneca Ab | Therapeutic use |
HUP0402588A3 (en) | 2002-02-01 | 2009-09-28 | Astrazeneca Ab | Quinazoline derivatives, pharmaceutical compositions containing them, process for producing them and their use |
JP4389205B2 (en) | 2002-02-06 | 2009-12-24 | 宇部興産株式会社 | Preparation of 4-aminoquinazoline 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 |
JP2005536486A (en) * | 2002-07-09 | 2005-12-02 | アストラゼネカ アクチボラグ | Quinazoline derivatives for use in the treatment of cancer |
EP2280003B1 (en) | 2002-07-15 | 2014-04-02 | Symphony Evolution, Inc. | Process for preparing receptor-type kinase modulators |
CN1688549A (en) * | 2002-08-23 | 2005-10-26 | 麒麟麦酒株式会社 | Compound having TGF-beta inhibitory activity and medicinal composition containing the same |
KR101089462B1 (en) * | 2002-11-04 | 2011-12-07 | 아스트라제네카 아베 | Quinazoline derivatives as src tyrosine kinase inhibitors |
ATE508747T1 (en) | 2003-03-10 | 2011-05-15 | Eisai R&D Man Co Ltd | C-KIT KINASE INHIBITORS |
GB0309850D0 (en) | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
GB0310401D0 (en) * | 2003-05-07 | 2003-06-11 | Astrazeneca Ab | Therapeutic agent |
GB0316127D0 (en) * | 2003-07-10 | 2003-08-13 | Astrazeneca Ab | Combination therapy |
GB0316123D0 (en) * | 2003-07-10 | 2003-08-13 | Astrazeneca Ab | Combination therapy |
GB0318422D0 (en) | 2003-08-06 | 2003-09-10 | Astrazeneca Ab | Chemical compounds |
GB0318423D0 (en) * | 2003-08-06 | 2003-09-10 | Astrazeneca Ab | Chemical compounds |
WO2005016346A1 (en) * | 2003-08-14 | 2005-02-24 | Array Biopharma Inc. | Quinazoline analogs as receptor tyrosine kinase inhibitors |
PT2213661E (en) | 2003-09-26 | 2011-12-15 | Exelixis Inc | C-met modulators and methods of use |
WO2005044788A1 (en) | 2003-11-11 | 2005-05-19 | Eisai Co., Ltd. | Urea derivative and process for producing the same |
GB0328040D0 (en) * | 2003-12-03 | 2004-01-07 | Coleman Robert E | Pharmaceutical uses of bisphosphonates |
GEP20084572B (en) | 2003-12-23 | 2008-12-25 | Pfizer | Novel quinoline derivatives |
GB0330002D0 (en) | 2003-12-24 | 2004-01-28 | Astrazeneca Ab | Quinazoline derivatives |
US7435823B2 (en) * | 2004-01-23 | 2008-10-14 | Amgen Inc. | Compounds and methods of use |
US7626030B2 (en) | 2004-01-23 | 2009-12-01 | Amgen Inc. | Compounds and methods of use |
GB0406446D0 (en) * | 2004-03-23 | 2004-04-28 | Astrazeneca Ab | Combination therapy |
KR20060130764A (en) * | 2004-03-23 | 2006-12-19 | 아스트라제네카 아베 | Combination therapy |
GB0406445D0 (en) * | 2004-03-23 | 2004-04-28 | Astrazeneca Ab | Combination therapy |
WO2005113494A2 (en) | 2004-05-07 | 2005-12-01 | Amgen Inc. | Nitrogenated heterocyclic derivatives as protein kinase modulators and use for the treatment of angiogenesis and cancer |
EP1797877A4 (en) | 2004-09-13 | 2010-12-15 | Eisai Co Ltd | Joint use of sulfonamide based compound with angiogenesis inhibitor |
US8772269B2 (en) | 2004-09-13 | 2014-07-08 | Eisai R&D Management Co., Ltd. | Use of sulfonamide-including compounds in combination with angiogenesis inhibitors |
CA2579810C (en) | 2004-09-17 | 2012-01-24 | Eisai R&D Management Co., Ltd. | Stable pharmaceutical compositions of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide |
US7285569B2 (en) | 2004-09-24 | 2007-10-23 | Hoff Hoffmann-La Roche Inc. | Tricycles, their manufacture and use as pharmaceutical agents |
AR050948A1 (en) | 2004-09-24 | 2006-12-06 | Hoffmann La Roche | DERIVATIVES OF FTALAZINONA; ITS OBTAINING AND ITS USE IN THE MANUFACTURE OF MEDICINES FOR THE TREATMENT OF CANCER. |
EP1796672A1 (en) * | 2004-09-27 | 2007-06-20 | AstraZeneca AB | Cancer combination therapy comprising azd2171 and imatinib |
EP1802591B1 (en) | 2004-10-12 | 2012-01-11 | AstraZeneca AB | Quinazoline derivatives |
AU2005312048B2 (en) | 2004-11-30 | 2012-08-02 | Amgen Inc. | Quinolines and quinazoline analogs and their use as medicaments for treating cancer |
PT1838733E (en) | 2004-12-21 | 2011-12-13 | Medimmune Ltd | Antibodies directed to angiopoietin-2 and uses thereof |
EP1674467A1 (en) * | 2004-12-22 | 2006-06-28 | 4Sc Ag | 2,5- and 2,6-disubstituted benzazole derivatives useful as protein kinase inhibitors |
US7462639B2 (en) | 2005-04-14 | 2008-12-09 | Hoffmann-La Roche Inc. | Aminopyrazole derivatives |
JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Substituted Amid derivatives & methods of use |
DE602006010243D1 (en) | 2005-05-18 | 2009-12-17 | Array Biopharma Inc | 4- (phenylamino) -6-oxo-1,6-dihydropyridazine-3-carboxamide derivatives as MEK inhibitors for the treatment of hyperproliferative disorders |
JP2009500347A (en) | 2005-06-30 | 2009-01-08 | アムジエン・インコーポレーテツド | Bisaryl kinase inhibitors and their use in the treatment of inflammation, angiogenesis and cancer |
JP5066446B2 (en) * | 2005-08-01 | 2012-11-07 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | Methods for predicting the effects of angiogenesis inhibitors |
EP2281901B1 (en) | 2005-08-02 | 2013-11-27 | Eisai R&D Management Co., Ltd. | Anti-tumour pharmaceutical composition with angiogenesis inhibitors |
CN101277720A (en) * | 2005-09-01 | 2008-10-01 | 卫材R&D管理有限公司 | Method for preparation of pharmaceutical composition having improved disintegradability |
US8247556B2 (en) | 2005-10-21 | 2012-08-21 | Amgen Inc. | Method for preparing 6-substituted-7-aza-indoles |
EP1949902B1 (en) | 2005-11-07 | 2012-06-27 | Eisai R&D Management Co., Ltd. | USE OF COMBINATION OF ANTI-ANGIOGENIC SUBSTANCE AND c-kit KINASE INHIBITOR |
WO2007061130A1 (en) * | 2005-11-22 | 2007-05-31 | Eisai R & D Management Co., Ltd. | Anti-tumor agent for multiple myeloma |
GB0523810D0 (en) | 2005-11-23 | 2006-01-04 | Astrazeneca Ab | Pharmaceutical compositions |
AU2006328201B2 (en) * | 2005-12-22 | 2010-08-19 | Astrazeneca Ab | Combination of AZD2171 and pemetrexed |
US7868177B2 (en) | 2006-02-24 | 2011-01-11 | Amgen Inc. | Multi-cyclic compounds and method of use |
JP2009528365A (en) * | 2006-02-28 | 2009-08-06 | アムゲン インコーポレイティッド | Cinnoline and quinazoline derivatives as phosphodiesterase 10 inhibitors |
WO2007099323A2 (en) * | 2006-03-02 | 2007-09-07 | Astrazeneca Ab | Quinoline derivatives |
UY30183A1 (en) * | 2006-03-02 | 2007-10-31 | Astrazeneca Ab | QUINOLINE DERIVATIVES |
TW200813091A (en) | 2006-04-10 | 2008-03-16 | Amgen Fremont Inc | Targeted binding agents directed to uPAR and uses thereof |
US20090209580A1 (en) * | 2006-05-18 | 2009-08-20 | Eisai R & D Management Co., Ltd. | Antitumor agent for thyroid cancer |
WO2008001956A1 (en) * | 2006-06-29 | 2008-01-03 | Eisai R & D Management Co., Ltd. | Therapeutic agent for liver fibrosis |
CL2007002225A1 (en) | 2006-08-03 | 2008-04-18 | Astrazeneca Ab | SPECIFIC UNION AGENT FOR A RECEIVER OF THE GROWTH FACTOR DERIVED FROM PLATES (PDGFR-ALFA); NUCLEIC ACID MOLECULA THAT CODIFIES IT; VECTOR AND CELL GUESTS THAT UNDERSTAND IT; CONJUGADO UNDERSTANDING THE AGENT; AND USE OF THE AGENT OF A |
HUE033894T2 (en) | 2006-08-23 | 2018-01-29 | Kudos Pharm Ltd | 2-methylmorpholine pyrido-,pyrazo- and pyrimido-pyrimidine derivatives as mtor inhibitors |
US8865737B2 (en) | 2006-08-28 | 2014-10-21 | Eisai R&D Management Co., Ltd. | Antitumor agent for undifferentiated gastric cancer |
CA2662587C (en) | 2006-09-11 | 2013-08-06 | Curis, Inc. | Quinazoline based egfr inhibitors |
CL2007003158A1 (en) | 2006-11-02 | 2008-05-16 | Astrazeneca Ab | PROCEDURE FOR PREPARATION OF COMPOUNDS DERIVED FROM QUINAZOLINA OR ITS PHARMACEUTICALLY ACCEPTABLE SALTS; INTERMEDIARY COMPOUNDS; PREPARATION PROCEDURE |
AU2012204077B2 (en) * | 2006-11-02 | 2012-11-29 | Astrazeneca Ab | Process for preparing indol-5-oxy-quinazoline derivatives and intermediates |
EP1921070A1 (en) | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | Bicyclic heterocycles, medicaments comprising them, their use and process for their preparation |
AU2007338793B2 (en) | 2006-12-20 | 2012-05-03 | Amgen Inc. | Heterocyclic compounds and their use in treating inflammation, angiogenesis and cancer |
AU2008211952B2 (en) | 2007-01-29 | 2012-07-19 | Eisai R & D Management Co., Ltd. | Composition for treatment of undifferentiated-type of gastric cancer |
KR20090116782A (en) | 2007-02-06 | 2009-11-11 | 베링거 인겔하임 인터내셔날 게엠베하 | Bicyclic heterocycles, drugs containing said compounds, use thereof, and method for production thereof |
US20080190689A1 (en) * | 2007-02-12 | 2008-08-14 | Ballard Ebbin C | Inserts for engine exhaust systems |
US8148532B2 (en) | 2007-03-14 | 2012-04-03 | Guoqing Paul Chen | Spiro substituted compounds as angiogenesis inhibitors |
PE20081887A1 (en) | 2007-03-20 | 2009-01-16 | Dainippon Sumitomo Pharma Co | NEW ADENINE COMPOUND |
EP2138497A4 (en) | 2007-03-20 | 2012-01-04 | Dainippon Sumitomo Pharma Co | Novel adenine compound |
CN101678001A (en) * | 2007-04-13 | 2010-03-24 | 阿斯利康(瑞典)有限公司 | Combination therapy comprising AZD2171 and AZD6244 or MEK-inhibitor II |
PT2154967E (en) | 2007-04-16 | 2014-06-05 | Hutchison Medipharma Entpr Ltd | Pyrimidine derivatives |
WO2009030224A2 (en) * | 2007-09-07 | 2009-03-12 | Schebo Biotech Ag | Novel quinazoline compounds and the use thereof for treating cancerous diseases |
US8119616B2 (en) | 2007-09-10 | 2012-02-21 | Curis, Inc. | Formulation of quinazoline based EGFR inhibitors containing a zinc binding moiety |
TW200922590A (en) * | 2007-09-10 | 2009-06-01 | Curis Inc | VEGFR inhibitors containing a zinc binding moiety |
EP2190287B1 (en) | 2007-09-10 | 2014-10-29 | Curis, Inc. | Tartrate salts or complexes of quinazoline based egfr inhibitors containing a zinc binding moiety |
PL2201012T3 (en) | 2007-10-11 | 2014-11-28 | Astrazeneca Ab | Pyrrolo[2,3-d]pyrimidin derivatives as protein kinase b inhibitors |
CA2703257C (en) * | 2007-10-29 | 2013-02-19 | Amgen Inc. | Benzomorpholine derivatives and methods of use |
US8952035B2 (en) | 2007-11-09 | 2015-02-10 | Eisai R&D Management Co., Ltd. | Combination of anti-angiogenic substance and anti-tumor platinum complex |
PT2222675E (en) | 2007-12-19 | 2013-11-13 | Genentech Inc | 5-anilinoimidazopyridines and methods of use |
KR20100099185A (en) | 2007-12-21 | 2010-09-10 | 제넨테크, 인크. | Azaindolizines and methods of use |
CN101215274B (en) * | 2007-12-27 | 2011-05-04 | 上海北卡医药技术有限公司 | Technique for preparing N-substituted morpholines organic compounds |
ES2385118T3 (en) * | 2008-01-17 | 2012-07-18 | Bayer Pharma Aktiengesellschaft | Sulfoximin-substituted quinazoline derivatives as immunomodulators, their preparation and use as medicines |
WO2009094211A1 (en) * | 2008-01-22 | 2009-07-30 | Concert Pharmaceuticals Inc. | Quinazoline compounds and methods of treating cancer |
AU2009210098B2 (en) * | 2008-01-29 | 2013-06-13 | Eisai R & D Management Co., Ltd. | Combined use of angiogenesis inhibitor and taxane |
DK2245026T3 (en) | 2008-02-07 | 2012-10-15 | Boehringer Ingelheim Int | Spirocyclic heterocycles, drug containing these compounds, their use and process for their preparation |
CN102014912A (en) * | 2008-02-21 | 2011-04-13 | 阿斯利康(瑞典)有限公司 | Combination therapy 238 |
EP2276488A1 (en) * | 2008-03-26 | 2011-01-26 | Novartis AG | 5imidazoquinolines and pyrimidine derivatives as potent modulators of vegf-driven angiogenic processes |
US7829574B2 (en) | 2008-05-09 | 2010-11-09 | Hutchison Medipharma Enterprises Limited | Substituted quinazoline compounds and their use in treating angiogenesis-related diseases |
KR20110014192A (en) | 2008-05-13 | 2011-02-10 | 아스트라제네카 아베 | Fumarate salt of 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-([1-(n-methylcarbamoylmethyl)piperidin-4-yl]oxy)quinazoline |
US8426430B2 (en) | 2008-06-30 | 2013-04-23 | Hutchison Medipharma Enterprises Limited | Quinazoline derivatives |
EP2149565A1 (en) * | 2008-07-24 | 2010-02-03 | Bayer Schering Pharma AG | Sulfoximine substituted chinazoline derivatives as immune modulators for the treatment of inflammatory and allergic diseases |
EP2313397B1 (en) | 2008-08-08 | 2016-04-20 | Boehringer Ingelheim International GmbH | Cyclohexyloxy substituted heterocycles, medicine containing these connections, their application and production method |
US8211911B2 (en) | 2008-08-19 | 2012-07-03 | Guoqing Paul Chen | Compounds as kinase inhibitors |
US7737157B2 (en) | 2008-08-29 | 2010-06-15 | Hutchison Medipharma Enterprises Limited | Pyrimidine compounds |
JP5778577B2 (en) | 2008-09-19 | 2015-09-16 | メディミューン,エルエルシー | Antibodies against DLL4 and uses thereof |
EP2532657B9 (en) * | 2008-10-14 | 2017-04-19 | Sunshine Lake Pharma Co., Ltd. | Compounds and methods of use |
US20110053923A1 (en) | 2008-12-22 | 2011-03-03 | Astrazeneca | Chemical compounds 610 |
EP2379595A2 (en) | 2008-12-23 | 2011-10-26 | AstraZeneca AB | Targeted binding agents directed to 5 1 and uses thereof |
NZ594594A (en) | 2009-01-16 | 2013-11-29 | Exelixis Inc | Malate salt of n-(4-{ [6,7-bis(methyloxy)quinolin-4-yl]oxy} phenyl)-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide, and crystalline forms thereof for the treatment of cancer |
EP3100745B1 (en) | 2009-02-05 | 2018-04-18 | Immunogen, Inc. | Novel benzodiazepine derivatives |
WO2010089580A1 (en) | 2009-02-06 | 2010-08-12 | Astrazeneca Ab | Use of a mct1 inhibitor in the treatment of cancers expressing mct1 over mct4 |
ES2427917T3 (en) | 2009-02-10 | 2013-11-04 | Astrazeneca Ab | Triazolo [4,3-b] pyridazine derivatives and their uses for prostate cancer |
US8785457B2 (en) | 2009-03-13 | 2014-07-22 | Cellzome Limited | Pyrimidine derivatives as mTOR inhibitors |
IT1393351B1 (en) * | 2009-03-16 | 2012-04-20 | Eos Ethical Oncology Science Spa In Forma Abbreviata Eos Spa | PROCEDURE FOR THE PREPARATION OF 6- (7 - ((1-AMINOCYCLOPROPYL) METHOSSI) -6-METOSSICHINOLIN-4-ILOSSI) -N-METHYL-1-NAFTAMIDE AND ITS INTERMEDIATES OF SYNTHESIS |
JP5583751B2 (en) * | 2009-03-21 | 2014-09-03 | クイ ニング | Amino ester derivatives, salts thereof, and methods of use |
GB0905127D0 (en) | 2009-03-25 | 2009-05-06 | Pharminox Ltd | Novel prodrugs |
CA2758614A1 (en) | 2009-04-14 | 2010-10-21 | Cellzome Limited | Fluoro substituted pyrimidine compounds as jak3 inhibitors |
US8389580B2 (en) | 2009-06-02 | 2013-03-05 | Duke University | Arylcyclopropylamines and methods of use |
US20100317593A1 (en) | 2009-06-12 | 2010-12-16 | Astrazeneca Ab | 2,3-dihydro-1h-indene compounds |
UA108618C2 (en) | 2009-08-07 | 2015-05-25 | APPLICATION OF C-MET-MODULATORS IN COMBINATION WITH THEMOSOLOMID AND / OR RADIATION THERAPY FOR CANCER TREATMENT | |
CA2771675A1 (en) | 2009-09-11 | 2011-03-17 | Cellzome Limited | Ortho substituted pyrimidine compounds as jak inhibitors |
EA022120B1 (en) | 2009-10-20 | 2015-11-30 | Целльзом Лимитид | Heterocyclyl pyrazolopyrimidine analogues as jak inhibitors |
US8399460B2 (en) | 2009-10-27 | 2013-03-19 | Astrazeneca Ab | Chromenone derivatives |
KR20120113709A (en) | 2009-11-18 | 2012-10-15 | 아스트라제네카 아베 | Benzoimidazole compounds and uses thereof |
NO2504364T3 (en) | 2009-11-24 | 2018-01-06 | ||
JP2013512859A (en) | 2009-12-03 | 2013-04-18 | 大日本住友製薬株式会社 | Imidazoquinoline acting through a toll-like receptor (TLR) |
WO2011090738A2 (en) * | 2009-12-29 | 2011-07-28 | Dana-Farber Cancer Institute, Inc. | Type ii raf kinase inhibitors |
CA2786465C (en) | 2010-01-15 | 2018-09-25 | Suzhou Neupharma Co., Ltd. | Bufalin derivatives for the treatment of cancer |
US8198285B2 (en) | 2010-01-19 | 2012-06-12 | Astrazeneca Ab | Pyrazine derivatives |
WO2011095807A1 (en) | 2010-02-07 | 2011-08-11 | Astrazeneca Ab | Combinations of mek and hh inhibitors |
EP2533810B1 (en) | 2010-02-10 | 2016-10-12 | ImmunoGen, Inc. | Cd20 antibodies and uses thereof |
EP2542536B1 (en) | 2010-03-04 | 2015-01-21 | Cellzome Limited | Morpholino substituted urea derivatives as mtor inhibitors |
MX2012012328A (en) | 2010-04-30 | 2013-05-06 | Cellzome Ltd | Pyrazole compounds as jak inhibitors. |
SA111320519B1 (en) | 2010-06-11 | 2014-07-02 | Astrazeneca Ab | Pyrimidinyl Compounds for Use as ATR Inhibitors |
BR112012032462A2 (en) | 2010-06-25 | 2016-11-08 | Eisai R&D Man Co Ltd | antitumor agent employing compounds which, in combination, have kinase inhibiting effect. |
EP2588105A1 (en) | 2010-07-01 | 2013-05-08 | Cellzome Limited | Triazolopyridines as tyk2 inhibitors |
TWI535712B (en) | 2010-08-06 | 2016-06-01 | 阿斯特捷利康公司 | Chemical compounds |
US9040545B2 (en) | 2010-08-20 | 2015-05-26 | Cellzome Limited | Heterocyclyl pyrazolopyrimidine analogues as selective JAK inhibitors |
US9018197B2 (en) | 2010-08-28 | 2015-04-28 | Suzhou Neupharma Co. Ltd. | Tetradecahydro-1H-cyclopenta[a]phenanthrene compounds, compositions, and related methods of use |
GB201016442D0 (en) | 2010-09-30 | 2010-11-17 | Pharminox Ltd | Novel acridine derivatives |
EP2638018A1 (en) | 2010-11-09 | 2013-09-18 | Cellzome Limited | Pyridine compounds and aza analogues thereof as tyk2 inhibitors |
WO2012066336A1 (en) | 2010-11-19 | 2012-05-24 | Astrazeneca Ab | Benzylamine compounds as toll -like receptor 7 agonists |
WO2012067269A1 (en) | 2010-11-19 | 2012-05-24 | Dainippon Sumitomo Pharma Co., Ltd. | Aminoalkoxyphenyl compounds and their use in the treatment of disease |
EP2640716A1 (en) | 2010-11-19 | 2013-09-25 | Dainippon Sumitomo Pharma Co., Ltd. | Cyclic amide compounds and their use in the treatment of disease |
WO2012066335A1 (en) | 2010-11-19 | 2012-05-24 | Astrazeneca Ab | Phenol compounds als toll -like receptor 7 agonists |
US9493503B2 (en) | 2011-02-02 | 2016-11-15 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
WO2012128868A1 (en) | 2011-02-15 | 2012-09-27 | Immunogen, Inc. | Cytotoxic benzodiazepine derivatives |
JP5937111B2 (en) | 2011-02-17 | 2016-06-22 | カンサー・セラピューティクス・シーアールシー・プロプライエタリー・リミテッドCancer Therapeutics Crc Pty Limited | FAK inhibitor |
JP5937112B2 (en) | 2011-02-17 | 2016-06-22 | カンサー・セラピューティクス・シーアールシー・プロプライエタリー・リミテッドCancer Therapeutics Crc Pty Limited | Selective FAK inhibitor |
GB201104267D0 (en) | 2011-03-14 | 2011-04-27 | Cancer Rec Tech Ltd | Pyrrolopyridineamino derivatives |
EP2694511A1 (en) | 2011-04-04 | 2014-02-12 | Cellzome Limited | Dihydropyrrolo pyrimidine derivatives as mtor inhibitors |
UY34013A (en) | 2011-04-13 | 2012-11-30 | Astrazeneca Ab | ? CHROMENONE COMPOUNDS WITH ANTI-TUMORAL ACTIVITY ?. |
WO2012143320A1 (en) | 2011-04-18 | 2012-10-26 | Cellzome Limited | (7h-pyrrolo[2,3-d]pyrimidin-2-yl)amine compounds as jak3 inhibitors |
RU2580609C2 (en) | 2011-04-18 | 2016-04-10 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Anticancer therapeutic agent |
ES2841809T3 (en) | 2011-06-03 | 2021-07-09 | Eisai R&D Man Co Ltd | Biomarkers to predict and evaluate the degree of response of subjects with thyroid and kidney cancer to lenvatinib compounds |
WO2012175991A1 (en) | 2011-06-24 | 2012-12-27 | Pharminox Limited | Fused pentacyclic anti - proliferative compounds |
EP3333161B1 (en) | 2011-07-27 | 2020-02-19 | Astrazeneca AB | 2-(2,4,5-substituted-anilino)pyrimidine derivatives as egfr modulators useful for treating cancer |
US20140179664A1 (en) | 2011-07-28 | 2014-06-26 | Cellzome Limited | Heterocyclyl Pyrimidine Analogues As JAK Inhibitors |
WO2013017480A1 (en) | 2011-07-29 | 2013-02-07 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors |
WO2013017479A1 (en) | 2011-07-29 | 2013-02-07 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors |
EP2747767B8 (en) | 2011-08-26 | 2019-07-17 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
WO2013033250A1 (en) | 2011-09-01 | 2013-03-07 | Xiangping Qian | Certain chemical entities, compositions, and methods |
US9518029B2 (en) | 2011-09-14 | 2016-12-13 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
US20140323504A1 (en) | 2011-09-20 | 2014-10-30 | Cellzome Limited | Pyrazolo[4,3-c]Pyridine Derivatives As Kinase Inhibitors |
US9249110B2 (en) | 2011-09-21 | 2016-02-02 | Neupharma, Inc. | Substituted quinoxalines as B-raf kinase inhibitors |
EP2758379B1 (en) | 2011-09-21 | 2016-10-19 | Cellzome Limited | Urea and carbamate derivatives of 2-morpholino-1,3,5-triazine as mTOR inhibitors for the treatment of immunological or proliferative diseases |
US20140235573A1 (en) | 2011-09-29 | 2014-08-21 | The University Of Liverpool | Prevention and/or treatment of cancer and/or cancer metastasis |
WO2013049701A1 (en) | 2011-09-30 | 2013-04-04 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
KR20140084130A (en) | 2011-10-07 | 2014-07-04 | 셀좀 리미티드 | Morpholino substituted bicyclic pyrimidine urea or carbamate derivatives as mtor inhibitors |
US20130178520A1 (en) | 2011-12-23 | 2013-07-11 | Duke University | Methods of treatment using arylcyclopropylamine compounds |
EP2794598A1 (en) | 2011-12-23 | 2014-10-29 | Cellzome Limited | Pyrimidine-2,4-diamine derivatives as kinase inhibitors |
WO2013112950A2 (en) | 2012-01-25 | 2013-08-01 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
EP2626066A1 (en) | 2012-02-10 | 2013-08-14 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Combination therapy comprising selective VEGFR-2 inhibitors and MEK inhibitors |
EP3453713B1 (en) | 2012-04-29 | 2021-09-08 | Neupharma, Inc. | Bufadienolide compounds substituted in position 3 by an amine group for use in the treatment of cancer |
DK2859017T3 (en) | 2012-06-08 | 2019-05-13 | Sutro Biopharma Inc | ANTIBODIES INCLUDING PLACE-SPECIFIC NON-NATURAL AMINO ACID, PROCEDURE FOR MANUFACTURING ITS AND METHODS OF USE THEREOF |
DK2863955T3 (en) | 2012-06-26 | 2017-01-23 | Sutro Biopharma Inc | MODIFIED FC PROTEINS, INCLUDING LOCATION-SPECIFIC NON-NATURAL AMINO ACID RESIDUES, CONJUGATES THEREOF, METHODS OF PRODUCING ITS AND PROCEDURES FOR USE THEREOF |
WO2014026243A1 (en) | 2012-08-17 | 2014-02-20 | Cancer Therapeutics Crc Pty Limited | Vegfr3 inhibitors |
EP2887965A1 (en) | 2012-08-22 | 2015-07-01 | ImmunoGen, Inc. | Cytotoxic benzodiazepine derivatives |
HRP20220455T1 (en) | 2012-08-31 | 2022-05-27 | Sutro Biopharma, Inc. | Modified amino acids comprising an azido group |
WO2014041349A1 (en) | 2012-09-12 | 2014-03-20 | Cancer Therapeutics Crc Pty Ltd | Tetrahydropyran-4-ylethylamino- or tetrahydropyranyl-4-ethyloxy-pyrimidines or -pyridazines as isoprenylcysteincarboxymethyl transferase inhibitors |
WO2014045101A1 (en) | 2012-09-21 | 2014-03-27 | Cellzome Gmbh | Tetrazolo quinoxaline derivatives as tankyrase inhibitors |
EP2897618B1 (en) | 2012-09-24 | 2021-11-17 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
CN104955459B (en) | 2012-11-05 | 2019-02-01 | 南特知识产权控股有限责任公司 | Substituted indoles -5- amphyl and its treatment use |
WO2014075077A1 (en) | 2012-11-12 | 2014-05-15 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
US9334239B2 (en) | 2012-12-21 | 2016-05-10 | Eisai R&D Management Co., Ltd. | Amorphous form of quinoline derivative, and method for producing same |
WO2014117274A1 (en) | 2013-01-31 | 2014-08-07 | Neomed Institute | Imidazopyridine compounds and uses thereof |
EP2956138B1 (en) | 2013-02-15 | 2022-06-22 | Kala Pharmaceuticals, Inc. | Therapeutic compounds and uses thereof |
US9688688B2 (en) | 2013-02-20 | 2017-06-27 | Kala Pharmaceuticals, Inc. | Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof |
CN107915751A (en) * | 2013-02-20 | 2018-04-17 | 卡拉制药公司 | Therapeutic compound and its purposes |
EP2961435B1 (en) | 2013-02-28 | 2019-05-01 | ImmunoGen, Inc. | Conjugates comprising cell-binding agents and cytotoxic agents |
WO2014134483A2 (en) | 2013-02-28 | 2014-09-04 | Immunogen, Inc. | Conjugates comprising cell-binding agents and cytotoxic agents |
SI2970263T1 (en) | 2013-03-13 | 2018-09-28 | Abbvie Inc. | Processes for the preparation of an apoptosis-inducing agent |
CN105142648A (en) | 2013-03-15 | 2015-12-09 | 玛格塞蒂克斯公司 | Magnesium compositions and uses thereof for cancers |
BR112015022307A2 (en) | 2013-03-15 | 2017-07-18 | Nantbioscience Inc | indol-5-ol substituted derivatives and their therapeutic applications |
AR095443A1 (en) | 2013-03-15 | 2015-10-14 | Fundación Centro Nac De Investig Oncológicas Carlos Iii | HEREROCICLES CONDENSED WITH ACTION ON ATR |
WO2014166386A1 (en) * | 2013-04-09 | 2014-10-16 | 广州康睿生物医药科技有限公司 | Anti-angiogenesis compound, intermediate and use thereof |
WO2014185540A1 (en) | 2013-05-14 | 2014-11-20 | Eisai R&D Management Co., Ltd. | Biomarkers for predicting and assessing responsiveness of endometrial cancer subjects to lenvatinib compounds |
EP2806480B1 (en) * | 2013-05-20 | 2017-08-09 | Nintendo Co., Ltd. | Battery accomodation structure and battery accomodation method |
CN103275069B (en) * | 2013-05-22 | 2015-03-11 | 苏州明锐医药科技有限公司 | Preparation method of cediranib |
WO2014194030A2 (en) | 2013-05-31 | 2014-12-04 | Immunogen, Inc. | Conjugates comprising cell-binding agents and cytotoxic agents |
US20160115146A1 (en) | 2013-06-07 | 2016-04-28 | Universite Catholique De Louvain | 3-carboxy substituted coumarin derivatives with a potential utility for the treatment of cancer diseases |
EP3336103B1 (en) | 2013-07-10 | 2021-03-17 | Sutro Biopharma, Inc. | Antibodies comprising multiple site-specific non-natural amino acid residues, methods of their preparation and methods of their use |
ES2729381T3 (en) | 2013-08-23 | 2019-11-04 | Neupharma Inc | Certain chemical entities, compositions and methods |
CN103509005B (en) * | 2013-09-26 | 2015-04-08 | 苏州海特比奥生物技术有限公司 | Quinazoline compound as well as preparation method and application thereof |
US9840493B2 (en) | 2013-10-11 | 2017-12-12 | Sutro Biopharma, Inc. | Modified amino acids comprising tetrazine functional groups, methods of preparation, and methods of their use |
EP2868702A1 (en) | 2013-10-29 | 2015-05-06 | DyStar Colours Distribution GmbH | Disperse dyes, their preparation and their use |
US9458169B2 (en) * | 2013-11-01 | 2016-10-04 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
US9890173B2 (en) | 2013-11-01 | 2018-02-13 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
EP3062795A4 (en) * | 2013-11-01 | 2017-05-31 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
GB201403536D0 (en) | 2014-02-28 | 2014-04-16 | Cancer Rec Tech Ltd | Inhibitor compounds |
SI3524595T1 (en) | 2014-08-28 | 2022-10-28 | Eisai R&D Management Co., Ltd. | High-purity quinoline derivative and method for manufacturing same |
CN105461698A (en) * | 2014-09-12 | 2016-04-06 | 杭州普晒医药科技有限公司 | Cediranib salt and crystal form thereof, and preparation methods and pharmaceutical composition of cediranib salt and crystal form thereof |
MA41179A (en) | 2014-12-19 | 2017-10-24 | Cancer Research Tech Ltd | PARG INHIBITOR COMPOUNDS |
GB201501870D0 (en) | 2015-02-04 | 2015-03-18 | Cancer Rec Tech Ltd | Autotaxin inhibitors |
GB201502020D0 (en) | 2015-02-06 | 2015-03-25 | Cancer Rec Tech Ltd | Autotaxin inhibitory compounds |
US10947201B2 (en) | 2015-02-17 | 2021-03-16 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
PT3263106T (en) | 2015-02-25 | 2024-01-12 | Eisai R&D Man Co Ltd | Method for suppressing bitterness of quinoline derivative |
KR20240064733A (en) | 2015-03-04 | 2024-05-13 | 머크 샤프 앤드 돔 코포레이션 | Combination of a pd-1 antagonist and a vegfr/fgfr/ret tyrosine kinase inhibitor for treating cancer |
GB201510019D0 (en) | 2015-06-09 | 2015-07-22 | Cancer Therapeutics Crc Pty Ltd | Compounds |
MX2017015896A (en) | 2015-06-16 | 2018-08-09 | Eisai R&D Man Co Ltd | Anticancer agent. |
CN108349964B (en) | 2015-08-04 | 2021-06-01 | 常州千红生化制药股份有限公司 | N- (pyridin-2-yl) -4- (thiazol-5-yl) pyrimidin-2-amines as therapeutic compounds |
BR112018006873A2 (en) | 2015-10-05 | 2018-11-06 | The Trustees Of Columbia University In The City Of New York | autophageal flow activators and phospholipase d and clearance of protein aggregates including tau and treatment of proteinopathies |
CA3011455A1 (en) | 2016-01-27 | 2017-08-03 | Sutro Biopharma, Inc. | Anti-cd74 antibody conjugates, compositions comprising anti-cd74 antibody conjugates and methods of using anti-cd74 antibody conjugates |
MX2018009867A (en) | 2016-02-15 | 2019-05-27 | Astrazeneca Ab | Methods comprising fixed intermittent dosing of cediranib. |
PL3442535T3 (en) | 2016-04-15 | 2022-10-24 | Cancer Research Technology Limited | Heterocyclic compounds as ret kinase inhibitors |
GB2554333A (en) | 2016-04-26 | 2018-04-04 | Big Dna Ltd | Combination therapy |
JP7101165B2 (en) | 2016-08-15 | 2022-07-14 | ニューファーマ, インコーポレイテッド | Specific chemical entities, compositions, and methods |
WO2018045379A1 (en) | 2016-09-02 | 2018-03-08 | Dana-Farber Cancer Institute, Inc. | Composition and methods of treating b cell disorders |
WO2018048750A1 (en) | 2016-09-08 | 2018-03-15 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
EP3509422A4 (en) | 2016-09-08 | 2020-05-20 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
US10336767B2 (en) * | 2016-09-08 | 2019-07-02 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
AU2017332839B2 (en) | 2016-09-22 | 2021-11-11 | Cancer Research Technology Limited | Preparation and uses of pyrimidinone derivatives |
GB201617103D0 (en) | 2016-10-07 | 2016-11-23 | Cancer Research Technology Limited | Compound |
JP6755775B2 (en) * | 2016-11-04 | 2020-09-16 | 富士アミドケミカル株式会社 | 4-Fluoroisoquinoline manufacturing method |
WO2018098361A1 (en) | 2016-11-22 | 2018-05-31 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 12 (cdk12) and uses thereof |
US10786502B2 (en) | 2016-12-05 | 2020-09-29 | Apros Therapeutics, Inc. | Substituted pyrimidines containing acidic groups as TLR7 modulators |
WO2018106606A1 (en) | 2016-12-05 | 2018-06-14 | Apros Therapeutics, Inc. | Pyrimidine compounds containing acidic groups |
CN106831729A (en) * | 2016-12-19 | 2017-06-13 | 浙江工业大学 | A kind of purification process of AZD2171 |
CN110418789B (en) | 2017-02-01 | 2022-03-25 | 常州千红生化制药股份有限公司 | Derivatives of N-cycloalkyl/heterocycloalkyl-4- (imidazo [1,2-a ] pyridine) pyrimidin-2-amines as therapeutic agents |
GB201704325D0 (en) | 2017-03-17 | 2017-05-03 | Argonaut Therapeutics Ltd | Compounds |
GB201705971D0 (en) | 2017-04-13 | 2017-05-31 | Cancer Res Tech Ltd | Inhibitor compounds |
CN108864079B (en) | 2017-05-15 | 2021-04-09 | 深圳福沃药业有限公司 | Triazine compound and pharmaceutically acceptable salt thereof |
ES2975661T3 (en) | 2017-05-26 | 2024-07-11 | Cancer Research Tech Ltd | BCL6 inhibitors derived from 2-quinolone |
KR102628675B1 (en) | 2017-05-26 | 2024-01-25 | 캔써 리서치 테크놀로지 리미티드 | Inhibitor of BCL6 derived from benzimidazolone |
US20200207859A1 (en) | 2017-07-26 | 2020-07-02 | Sutro Biopharma, Inc. | Methods of using anti-cd74 antibodies and antibody conjugates in treatment of t-cell lymphoma |
CA3070903A1 (en) | 2017-08-18 | 2019-02-21 | Cancer Research Technology Limited | Pyrrolo[2,3-b]pyridine compounds and their use in the treatment of cancer |
EP3684814A1 (en) | 2017-09-18 | 2020-07-29 | Sutro Biopharma, Inc. | Anti-folate receptor alpha antibody conjugates and their uses |
MX2020007183A (en) * | 2017-10-20 | 2021-03-31 | Kala Pharmaceuticals Inc | Ret9 and vegfr2 inhibitors. |
NL2019801B1 (en) | 2017-10-25 | 2019-05-02 | Univ Leiden | Delivery vectors |
WO2019136514A1 (en) | 2018-01-15 | 2019-07-18 | University Of South Australia | 5-(pyrimidin-4-yl)thiazol-2-yl urea derivatives as therapeutic agents |
GB201801128D0 (en) | 2018-01-24 | 2018-03-07 | Univ Oxford Innovation Ltd | Compounds |
EP3749310A4 (en) | 2018-02-08 | 2021-08-18 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
WO2019175093A1 (en) | 2018-03-12 | 2019-09-19 | Astrazeneca Ab | Method for treating lung cancer |
WO2019197842A1 (en) | 2018-04-13 | 2019-10-17 | Cancer Research Technology Limited | Bcl6 inhibitors |
FR3080620B1 (en) | 2018-04-27 | 2021-11-12 | Univ Paris Sud | COMPOUNDS WITH TUBULIN POLYMERIZATION INHIBITOR ACTIVITY AND IMMUNOMODULATORY PROPERTIES |
GB201809102D0 (en) | 2018-06-04 | 2018-07-18 | Univ Oxford Innovation Ltd | Compounds |
WO2019236496A1 (en) | 2018-06-04 | 2019-12-12 | Apros Therapeutics, Inc. | Pyrimidine compounds containing acidic groups useful to treat diseases connected to the modulation of tlr7 |
GB201810092D0 (en) | 2018-06-20 | 2018-08-08 | Ctxt Pty Ltd | Compounds |
GB201810581D0 (en) | 2018-06-28 | 2018-08-15 | Ctxt Pty Ltd | Compounds |
US20220047716A1 (en) | 2018-09-17 | 2022-02-17 | Sutro Biopharma, Inc. | Combination therapies with anti-folate receptor antibody conjugates |
CN112996784B (en) * | 2018-09-18 | 2023-05-30 | 北京越之康泰生物医药科技有限公司 | Indole derivatives and their use in medicine |
SG11202102981SA (en) | 2018-09-25 | 2021-04-29 | Black Diamond Therapeutics Inc | Quinazoline derivatives as tyrosine kinase inhibitor, compositions, methods of making them and their use |
GB201819126D0 (en) | 2018-11-23 | 2019-01-09 | Cancer Research Tech Ltd | Inhibitor compounds |
CN111747931A (en) | 2019-03-29 | 2020-10-09 | 深圳福沃药业有限公司 | Azaaromatic cyclic amide derivatives for the treatment of cancer |
EP3946618A1 (en) | 2019-04-05 | 2022-02-09 | Storm Therapeutics Ltd | Mettl3 inhibitory compounds |
GB201905328D0 (en) | 2019-04-15 | 2019-05-29 | Azeria Therapeutics Ltd | Inhibitor compounds |
US20220362394A1 (en) | 2019-05-03 | 2022-11-17 | Sutro Biopharma, Inc. | Anti-bcma antibody conjugates |
GB201908885D0 (en) | 2019-06-20 | 2019-08-07 | Storm Therapeutics Ltd | Therapeutic compounds |
AU2020335054A1 (en) | 2019-08-31 | 2022-03-24 | Etern Biopharma (Shanghai) Co., Ltd. | Pyrazole derivative for FGFR inhibitor and preparation method therefor |
MX2022003276A (en) | 2019-09-20 | 2022-04-11 | Ideaya Biosciences Inc | 4-substituted indole and indazole sulfonamido derivatives as parg inhibitors. |
GB201913988D0 (en) | 2019-09-27 | 2019-11-13 | Celleron Therapeutics Ltd | Novel treatment |
GB201914860D0 (en) | 2019-10-14 | 2019-11-27 | Cancer Research Tech Ltd | Inhibitor compounds |
GB201915829D0 (en) | 2019-10-31 | 2019-12-18 | Cancer Research Tech Ltd | Compounds, compositions and therapeutic uses thereof |
GB201915831D0 (en) | 2019-10-31 | 2019-12-18 | Cancer Research Tech Ltd | Compounds, compositions and therapeutic uses thereof |
GB201915828D0 (en) | 2019-10-31 | 2019-12-18 | Cancer Research Tech Ltd | Compounds, compositions and therapeutic uses thereof |
IL293340A (en) | 2019-12-02 | 2022-07-01 | Storm Therapeutics Ltd | Polyheterocyclic compounds as mettl3 inhibitors |
EP4114852A1 (en) | 2020-03-03 | 2023-01-11 | Sutro Biopharma, Inc. | Antibodies comprising site-specific glutamine tags, methods of their preparation and methods of their use |
GB202004960D0 (en) | 2020-04-03 | 2020-05-20 | Kinsenus Ltd | Inhibitor compounds |
GB202012969D0 (en) | 2020-08-19 | 2020-09-30 | Univ Of Oxford | Inhibitor compounds |
WO2022074379A1 (en) | 2020-10-06 | 2022-04-14 | Storm Therapeutics Limited | Mettl3 inhibitory compounds |
US20240101589A1 (en) | 2020-10-08 | 2024-03-28 | Strom Therapeutics Limited | Inhibitors of mettl3 |
GB202102895D0 (en) | 2021-03-01 | 2021-04-14 | Cambridge Entpr Ltd | Novel compounds, compositions and therapeutic uses thereof |
AU2022276958A1 (en) | 2021-05-17 | 2023-12-07 | Hk Inno.N Corporation | Benzamide derivative, method for preparing same, and pharmaceutical composition for prevention or treatment of cancer containing same as active ingredient |
GB202107907D0 (en) | 2021-06-02 | 2021-07-14 | Storm Therapeutics Ltd | Combination therapies |
GB202108383D0 (en) | 2021-06-11 | 2021-07-28 | Argonaut Therapeutics Ltd | Compounds useful in the treatment or prevention of a prmt5-mediated disorder |
EP4413000A1 (en) | 2021-10-04 | 2024-08-14 | FoRx Therapeutics AG | N,n-dimethyl-4-(7-(n-(1-methylcyclopropyl)sulfamoyl)-imidazo[1,5-a]pyridin-5-yl)piperazine-1-carboxamide derivatives and the corresponding pyrazolo[1,5-a]pyridine derivatives as parg inhibitors for the treatment of cancer |
AU2022359801A1 (en) | 2021-10-04 | 2024-02-01 | Forx Therapeutics Ag | Parg inhibitory compounds |
WO2023081923A1 (en) | 2021-11-08 | 2023-05-11 | Frequency Therapeutics, Inc. | Platelet-derived growth factor receptor (pdgfr) alpha inhibitors and uses thereof |
GB202202199D0 (en) | 2022-02-18 | 2022-04-06 | Cancer Research Tech Ltd | Compounds |
WO2023161881A1 (en) * | 2022-02-25 | 2023-08-31 | Glaxosmithkline Intellectual Property Development Limited | Cytotoxicity targeting chimeras for ccr2-expressing cells |
WO2023175184A1 (en) | 2022-03-17 | 2023-09-21 | Forx Therapeutics Ag | 2,4-dioxo-1,4-dihydroquinazoline derivatives as parg inhibitors for the treatment of cancer |
WO2023175185A1 (en) | 2022-03-17 | 2023-09-21 | Forx Therapeutics Ag | 2,4-dioxo-1,4-dihydroquinazoline derivatives as parg inhibitors for the treatment of cancer |
GB202204935D0 (en) | 2022-04-04 | 2022-05-18 | Cambridge Entpr Ltd | Nanoparticles |
GB202209404D0 (en) | 2022-06-27 | 2022-08-10 | Univ Of Sussex | Compounds |
WO2024006542A1 (en) | 2022-06-30 | 2024-01-04 | Sutro Biopharma, Inc. | Anti-ror1 antibodies and antibody conjugates, compositions comprising anti-ror1 antibodies or antibody conjugates, and methods of making and using anti-ror1 antibodies and antibody conjugates |
WO2024003241A1 (en) | 2022-06-30 | 2024-01-04 | Astrazeneca Ab | Treatment for immuno-oncology resistant subjects with an anti pd-l1 antibody an antisense targeted to stat3 and an inhibitor of ctla-4 |
WO2024030825A1 (en) | 2022-08-01 | 2024-02-08 | Neupharma, Inc | Crystalline salts of crystalline salts of (3s,5r,8r,9s,10s,13r,14s,17r)-14-hydroxy-10,13-dimethyl-17-(2- oxo-2h-pyran-5-yl)hexadecahydro-1h-cyclopenta[a]phenanthren-3-yl piperazine-1-carboxylate |
GB202213167D0 (en) | 2022-09-08 | 2022-10-26 | Cambridge Entpr Ltd | Novel compounds, compositions and therapeutic uses thereof |
GB202213166D0 (en) | 2022-09-08 | 2022-10-26 | Cambridge Entpr Ltd | Novel compounds, compositions and therapeutic uses thereof |
GB202213164D0 (en) | 2022-09-08 | 2022-10-26 | Cambridge Entpr Ltd | Novel compounds, compositions and therapeutic uses thereof |
GB202213163D0 (en) | 2022-09-08 | 2022-10-26 | Cambridge Entpr Ltd | Novel compounds, compositions and therapeutic uses thereof |
WO2024059169A1 (en) * | 2022-09-14 | 2024-03-21 | Blueprint Medicines Corporation | Egfr inhibitors |
WO2024074497A1 (en) | 2022-10-03 | 2024-04-11 | Forx Therapeutics Ag | Parg inhibitory compound |
WO2024094962A1 (en) | 2022-11-02 | 2024-05-10 | Cancer Research Technology Limited | Pyrido[2,3-d]pyrimidin-2-amine derivatives as egfr inhibitors for the treatment of cancer |
WO2024094963A1 (en) | 2022-11-02 | 2024-05-10 | Cancer Research Technology Limited | 2-amino-pyrido[2,3-d]pyrimidin-7(8h)-one and 7-amino-1-pyrimido[4,5-d]pyrimidin-2(1 h)-one derivatives as egfr inhibitors for the treatment of cancer |
GB202218672D0 (en) | 2022-12-12 | 2023-01-25 | Storm Therapeutics Ltd | Inhibitory compounds |
WO2024173453A1 (en) | 2023-02-14 | 2024-08-22 | Ideaya Biosciences, Inc. | Heteroaryl-substituted imidazopyridine compounds |
WO2024173524A1 (en) | 2023-02-14 | 2024-08-22 | Ideaya Biosciences, Inc. | Heteroaryl-substituted benzimidazole compounds |
WO2024173530A1 (en) | 2023-02-14 | 2024-08-22 | Ideaya Biosciences, Inc. | Heteroaryl-substituted pyrazolo/imidazo pyridine compounds |
WO2024173514A1 (en) | 2023-02-14 | 2024-08-22 | Ideaya Biosciences, Inc. | Amide and ester-substituted imidazopyridine compounds |
US20240336628A1 (en) | 2023-03-10 | 2024-10-10 | Breakpoint Therapeutics Gmbh | Novel compounds, compositions, and therapeutic uses thereof |
WO2024209035A1 (en) | 2023-04-05 | 2024-10-10 | Forx Therapeutics Ag | Parg inhibitory compounds |
Family Cites Families (61)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3557142A (en) * | 1968-02-20 | 1971-01-19 | Sterling Drug Inc | 4,5,6,7-tetrahydro-indole-lower-alkanoic acids and esters |
US4460584A (en) | 1981-03-13 | 1984-07-17 | Imperial Chemical Industries Plc | Nitrogen heterocycles |
IL81307A0 (en) | 1986-01-23 | 1987-08-31 | Union Carbide Agricult | Method for reducing moisture loss from plants and increasing crop yield utilizing nitrogen containing heterocyclic compounds and some novel polysubstituted pyridine derivatives |
US5411963A (en) | 1988-01-29 | 1995-05-02 | Dowelanco | Quinazoline derivatives |
IL89029A (en) | 1988-01-29 | 1993-01-31 | Lilly Co Eli | Fungicidal quinoline and cinnoline derivatives, compositions containing them, and fungicidal methods of using them |
GB8819307D0 (en) | 1988-08-13 | 1988-09-14 | Pfizer Ltd | Antiarrhythmic agents |
US5480883A (en) | 1991-05-10 | 1996-01-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
US5710158A (en) | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
US6645969B1 (en) | 1991-05-10 | 2003-11-11 | Aventis Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
CA2102780C (en) | 1991-05-10 | 2007-01-09 | Alfred P. Spada | Bis mono-and bicyclic aryl and heteroaryl compounds which inhibit egf and/or pdgf receptor tyrosine kinase |
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 |
US5714493A (en) | 1991-05-10 | 1998-02-03 | Rhone-Poulenc Rorer Pharmaceuticals, Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
NZ243082A (en) | 1991-06-28 | 1995-02-24 | Ici Plc | 4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof |
AU661533B2 (en) | 1992-01-20 | 1995-07-27 | Astrazeneca Ab | Quinazoline derivatives |
GB9323290D0 (en) * | 1992-12-10 | 1994-01-05 | Zeneca Ltd | Quinazoline derivatives |
GB9314893D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Quinazoline derivatives |
US5700823A (en) | 1994-01-07 | 1997-12-23 | Sugen, Inc. | Treatment of platelet derived growth factor related disorders such as cancers |
US5736534A (en) | 1994-02-23 | 1998-04-07 | Pfizer Inc. | 4-heterocyclyl-substituted quinazoline derivatives, processes for their preparation and their use as anti-cancer agents |
WO1995024190A2 (en) | 1994-03-07 | 1995-09-14 | Sugen, Inc. | Receptor tyrosine kinase inhibitors for inhibiting cell proliferative disorders and compositions thereof |
AU3619695A (en) | 1994-10-07 | 1996-05-02 | Zenyaku Kogyo Kabushiki Kaisha | Thioquinolone derivative |
DE4436509A1 (en) * | 1994-10-13 | 1996-04-18 | Hoechst Schering Agrevo Gmbh | Substituted spiroalkylamino and alkoxy heterocycles, processes for their preparation and their use as pesticides and fungicides |
GB9505651D0 (en) * | 1995-03-21 | 1995-05-10 | Agrevo Uk Ltd | AgrEvo UK Limited |
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 |
JP4009681B2 (en) | 1995-11-07 | 2007-11-21 | キリンファーマ株式会社 | Quinoline derivatives and quinazoline derivatives that inhibit platelet-derived growth factor receptor autophosphorylation and pharmaceutical compositions containing them |
GB9624482D0 (en) * | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
GB9603095D0 (en) | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
DE19614718A1 (en) | 1996-04-15 | 1997-10-16 | Hoechst Schering Agrevo Gmbh | Substituted pyridines / pyrimidines, processes for their preparation and their use as pesticides |
GB9707800D0 (en) | 1996-05-06 | 1997-06-04 | Zeneca Ltd | Chemical compounds |
GB9609641D0 (en) * | 1996-05-09 | 1996-07-10 | Pfizer Ltd | Compounds useful in therapy |
ATE227283T1 (en) | 1996-07-13 | 2002-11-15 | Glaxo Group Ltd | CONDENSED HETEROCYCLIC COMPOUNDS AS PROTEIN KINASE INHIBITORS |
CN1252054C (en) * | 1996-09-25 | 2006-04-19 | 曾尼卡有限公司 | Qinoline derivatives inhibiting effect of growth factors such as VEGF |
US6225318B1 (en) | 1996-10-17 | 2001-05-01 | Pfizer Inc | 4-aminoquinazolone derivatives |
EP0837063A1 (en) | 1996-10-17 | 1998-04-22 | Pfizer Inc. | 4-Aminoquinazoline derivatives |
JP2002501532A (en) | 1997-05-30 | 2002-01-15 | メルク エンド カンパニー インコーポレーテッド | Novel angiogenesis inhibitors |
GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
ZA986729B (en) | 1997-07-29 | 1999-02-02 | Warner Lambert Co | Irreversible inhibitors of tyrosine kinases |
ATE368665T1 (en) | 1997-08-22 | 2007-08-15 | Astrazeneca Ab | OXINDOLYLQUINAZOLINE DERIVATIVES AS ANGIOGENESIS INHIBITORS |
US6162804A (en) | 1997-09-26 | 2000-12-19 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
GB9721437D0 (en) | 1997-10-10 | 1997-12-10 | Glaxo Group Ltd | Heteroaromatic compounds and their use in medicine |
WO1999028159A1 (en) | 1997-11-27 | 1999-06-10 | Continental Teves Ag & Co. Ohg | Method and device for supplying data to motor vehicles or for exchanging data |
RS49779B (en) | 1998-01-12 | 2008-06-05 | Glaxo Group Limited, | Byciclic heteroaromatic compounds as protein tyrosine kinase inhibitors |
GB9800575D0 (en) | 1998-01-12 | 1998-03-11 | Glaxo Group Ltd | Heterocyclic compounds |
US6172071B1 (en) | 1998-07-30 | 2001-01-09 | Hughes Institute | Lipid-lowering quinazoline derivative |
US6184226B1 (en) | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
GB2345486A (en) | 1999-01-11 | 2000-07-12 | Glaxo Group Ltd | Heteroaromatic protein tyrosine kinase inhibitors |
JP3270834B2 (en) | 1999-01-27 | 2002-04-02 | ファイザー・プロダクツ・インク | Heteroaromatic bicyclic derivatives useful as anticancer agents |
UA71945C2 (en) | 1999-01-27 | 2005-01-17 | Pfizer Prod Inc | Substituted bicyclic derivatives being used as anticancer agents |
CN100360505C (en) * | 1999-02-10 | 2008-01-09 | 阿斯特拉曾尼卡有限公司 | Quinazoline derivatives as angiogenesis inhibitors |
DE19911509A1 (en) | 1999-03-15 | 2000-09-21 | Boehringer Ingelheim Pharma | Bicyclic heterocycles, medicaments containing these compounds, their use and processes for their preparation |
PE20010306A1 (en) | 1999-07-02 | 2001-03-29 | Agouron Pharma | INDAZOLE COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM USEFUL FOR THE INHIBITION OF PROTEIN KINASE |
TWI262914B (en) | 1999-07-02 | 2006-10-01 | Agouron Pharma | Compounds and pharmaceutical compositions for inhibiting protein kinases |
JP3822494B2 (en) | 1999-10-19 | 2006-09-20 | メルク エンド カムパニー インコーポレーテッド | Tyrosine kinase inhibitor |
CN1245402C (en) | 2000-08-09 | 2006-03-15 | 阿斯特拉曾尼卡有限公司 | Chemical compounds |
NZ523388A (en) | 2000-08-09 | 2004-09-24 | Astrazeneca Ab | Cinnoline compounds |
KR20030036686A (en) | 2000-08-09 | 2003-05-09 | 아스트라제네카 아베 | Quinoline derivatives having vegf inhibiting activity |
HUP0402588A3 (en) * | 2002-02-01 | 2009-09-28 | Astrazeneca Ab | Quinazoline derivatives, pharmaceutical compositions containing them, process for producing them and their use |
GB0318422D0 (en) | 2003-08-06 | 2003-09-10 | Astrazeneca Ab | Chemical compounds |
GB0330002D0 (en) | 2003-12-24 | 2004-01-28 | Astrazeneca Ab | Quinazoline derivatives |
GB0523810D0 (en) * | 2005-11-23 | 2006-01-04 | Astrazeneca Ab | Pharmaceutical compositions |
CL2007003158A1 (en) | 2006-11-02 | 2008-05-16 | Astrazeneca Ab | PROCEDURE FOR PREPARATION OF COMPOUNDS DERIVED FROM QUINAZOLINA OR ITS PHARMACEUTICALLY ACCEPTABLE SALTS; INTERMEDIARY COMPOUNDS; PREPARATION PROCEDURE |
-
2000
- 2000-02-08 CN CNB2004100589826A patent/CN100360505C/en not_active Expired - Lifetime
- 2000-02-08 SK SK50002-2013A patent/SK288378B6/en not_active IP Right Cessation
- 2000-02-08 SK SK5029-2011A patent/SK288365B6/en not_active IP Right Cessation
- 2000-02-08 PL PL350565A patent/PL199802B1/en unknown
- 2000-02-08 EE EEP200900039A patent/EE200900039A/en unknown
- 2000-02-08 RU RU2001124816/15A patent/RU2262935C2/en active
- 2000-02-08 IL IL14474500A patent/IL144745A0/en unknown
- 2000-02-08 CN CNB008060851A patent/CN1167422C/en not_active Expired - Lifetime
- 2000-02-08 WO PCT/GB2000/000373 patent/WO2000047212A1/en active Application Filing
- 2000-02-08 KR KR1020017010133A patent/KR100838617B1/en active IP Right Grant
- 2000-02-08 PL PL381995A patent/PL205557B1/en unknown
- 2000-02-08 CA CA2674803A patent/CA2674803C/en not_active Expired - Lifetime
- 2000-02-08 KR KR1020077031001A patent/KR20080015482A/en not_active Application Discontinuation
- 2000-02-08 CZ CZ2012-783A patent/CZ305827B6/en not_active IP Right Cessation
- 2000-02-08 AT AT00902730T patent/ATE298237T1/en active
- 2000-02-08 DK DK05004285.2T patent/DK1553097T3/en active
- 2000-02-08 PT PT05004285T patent/PT1553097E/en unknown
- 2000-02-08 CZ CZ20012889A patent/CZ303692B6/en not_active IP Right Cessation
- 2000-02-08 EP EP00902730A patent/EP1154774B1/en not_active Expired - Lifetime
- 2000-02-08 AU AU24475/00A patent/AU763618B2/en not_active Expired
- 2000-02-08 US US09/913,020 patent/US7074800B1/en not_active Expired - Lifetime
- 2000-02-08 CA CA2362715A patent/CA2362715C/en not_active Expired - Lifetime
- 2000-02-08 SI SI200030726T patent/SI1154774T1/en unknown
- 2000-02-08 EE EEP200100409A patent/EE05345B1/en unknown
- 2000-02-08 HU HU1300035A patent/HU230000B1/en unknown
- 2000-02-08 HU HU0104964A patent/HU228964B1/en unknown
- 2000-02-08 SK SK1140-2001A patent/SK288138B6/en not_active IP Right Cessation
- 2000-02-08 TR TR2001/02314T patent/TR200102314T2/en unknown
- 2000-02-08 PT PT00902730T patent/PT1154774E/en unknown
- 2000-02-08 DE DE60020941T patent/DE60020941T2/en not_active Expired - Lifetime
- 2000-02-08 BR BRPI0008128A patent/BRPI0008128B8/en not_active IP Right Cessation
- 2000-02-08 ES ES00902730T patent/ES2242596T3/en not_active Expired - Lifetime
- 2000-02-08 AT AT05004285T patent/ATE482946T1/en active
- 2000-02-08 DE DE60045047T patent/DE60045047D1/en not_active Expired - Lifetime
- 2000-02-08 NZ NZ513204A patent/NZ513204A/en not_active IP Right Cessation
- 2000-02-08 EP EP08168638A patent/EP2050744A1/en not_active Withdrawn
- 2000-02-08 JP JP2000598164A patent/JP3893026B2/en not_active Expired - Lifetime
- 2000-02-08 NZ NZ530832A patent/NZ530832A/en not_active IP Right Cessation
- 2000-02-08 EE EEP201100025A patent/EE05708B1/en unknown
- 2000-02-08 ID IDW00200101712A patent/ID30552A/en unknown
- 2000-02-08 ES ES05004285T patent/ES2351699T3/en not_active Expired - Lifetime
- 2000-02-08 TR TR2005/00745T patent/TR200500745T2/en unknown
- 2000-02-08 CZ CZ2012-888A patent/CZ306810B6/en not_active IP Right Cessation
- 2000-02-08 DK DK00902730T patent/DK1154774T3/en active
- 2000-02-08 BR BRPI0017548A patent/BRPI0017548B8/en not_active IP Right Cessation
- 2000-02-08 MX MXPA01008182A patent/MXPA01008182A/en active IP Right Grant
- 2000-02-08 EP EP05004285A patent/EP1553097B1/en not_active Expired - Lifetime
- 2000-02-08 SI SI200031062T patent/SI1553097T1/en unknown
- 2000-08-02 UA UA2001096186A patent/UA73932C2/en unknown
-
2001
- 2001-07-24 IS IS6022A patent/IS2512B/en unknown
- 2001-08-01 ZA ZA200106340A patent/ZA200106340B/en unknown
- 2001-08-06 IL IL144745A patent/IL144745A/en not_active IP Right Cessation
- 2001-08-09 NO NO20013882A patent/NO321604B1/en not_active IP Right Cessation
-
2002
- 2002-04-12 HK HK02102781.7A patent/HK1041212B/en not_active IP Right Cessation
-
2005
- 2005-06-08 NO NO20052773A patent/NO331175B1/en not_active IP Right Cessation
- 2005-06-29 US US11/169,122 patent/US20060004017A1/en not_active Abandoned
- 2005-09-21 HK HK05108262A patent/HK1076104A1/en not_active IP Right Cessation
-
2006
- 2006-05-08 JP JP2006129249A patent/JP4651576B2/en not_active Expired - Lifetime
-
2008
- 2008-01-25 IS IS8708A patent/IS2807B/en unknown
- 2008-05-20 IL IL191581A patent/IL191581A0/en unknown
- 2008-05-20 IL IL191580A patent/IL191580A/en not_active IP Right Cessation
-
2010
- 2010-10-13 JP JP2010230444A patent/JP5710931B2/en not_active Expired - Lifetime
- 2010-12-09 CY CY20101101134T patent/CY1110979T1/en unknown
-
2011
- 2011-04-20 US US13/090,405 patent/US8492560B2/en not_active Expired - Fee Related
- 2011-08-03 NO NO20111095A patent/NO332895B1/en not_active IP Right Cessation
Similar Documents
Publication | Publication Date | Title |
---|---|---|
RU2001124816A (en) | Quinazoline derivatives as angiogenesis inhibitors | |
RU2365588C2 (en) | Quinazoline compounds | |
RU2413727C2 (en) | Pyrazole derivatives and use thereof as receptor tyrosine kinase inhibitors | |
RU2324684C2 (en) | Pyrimidine derivatives | |
JP2002527436A5 (en) | ||
ZA200106340B (en) | Quinazoline derivatives as angiogenesis inhibitors. | |
US20100029673A1 (en) | Therapeutic agents comprising an anti-angiogenic agent in combination with an src-inhibitor and their therapeutic use | |
AU2016216636B2 (en) | Method of treating proliferative disorders and other pathological conditions mediated by Bcr-Abl, c-Kit, DDR1, DDR2 or PDGF-R kinase activity | |
RU2003107683A (en) | Quinazoline derivatives | |
US20040191254A1 (en) | Method of treatment of thyroid cancer | |
KR20010014678A (en) | QT Dispersion and Heart Rate Variability Improvement with CRF Antagonists to Prevent Sudden Death | |
NO20021728L (en) | Pyrimidine derivatives | |
WO2009002553A1 (en) | Methods of treating multiple myeloma and resistant cancers | |
RU2006112599A (en) | QUINASOLINE DERIVATIVES AS TYROSINKINASE INHIBITORS | |
JP2004505964A5 (en) | ||
JP6795518B2 (en) | Compositions and Methods of Inhibiting Kinases | |
MXPA04002338A (en) | Carbazole derivatives and their use as npy5 receptor antagonists. | |
JP2018052974A (en) | Combination products with tyrosine kinase inhibitors and their use | |
KR20110097907A (en) | Hsp90 inhibitors for therapeutic treatment | |
RU2008127260A (en) | Quinazoline derivatives as vanilloid antagonists | |
RU2011122542A (en) | METHOD FOR INHIBITING RECEPTOR TYROSINKINASES BY MEANS OF EXTRAcellular ANTAGONISTS AND EXTRACELLULAR ANTAGONISTS | |
RU2005117337A (en) | QUINASOLINE DERIVATIVES AS SRC TYROSINKINASE INHIBITORS | |
RU2001126348A (en) | 4-HETEROCYCLICULESULFONAMIDIL-6-METHOXY-5- (2-METHOXYPHENOXY) -2-PYRIDYL PYRIMIDINE DERIVATIVES AND PHARMACEUTICAL COMPOSITION | |
CY1115353T1 (en) | NEW PRODUCERS OF SUBSTITUTED TETRACYCLIC IMIMAZOL, PROCEDURES FOR THEIR PREPARATION, PHARMACEUTICAL COMPOSITIONS INCLUDED | |
JP2007501212A5 (en) |