JP2008521900A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008521900A5 JP2008521900A5 JP2007544417A JP2007544417A JP2008521900A5 JP 2008521900 A5 JP2008521900 A5 JP 2008521900A5 JP 2007544417 A JP2007544417 A JP 2007544417A JP 2007544417 A JP2007544417 A JP 2007544417A JP 2008521900 A5 JP2008521900 A5 JP 2008521900A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- methoxy
- methyl
- oxy
- quinolinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- -1 piperazin-4-yl Chemical group 0.000 claims 101
- 150000001875 compounds Chemical class 0.000 claims 39
- 125000000623 heterocyclic group Chemical group 0.000 claims 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 24
- 229910052739 hydrogen Chemical group 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims 19
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 13
- 125000003342 alkenyl group Chemical group 0.000 claims 11
- 125000000304 alkynyl group Chemical group 0.000 claims 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 11
- 125000001153 fluoro group Chemical group F* 0.000 claims 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 9
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000001188 haloalkyl group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 5
- VQGICXKAKKMXHK-UHFFFAOYSA-N 1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-4-[phenyl(propoxy)methyl]pyrrolidin-2-one Chemical compound C1N(C=2C=C(F)C(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)C(=O)CC1C(OCCC)C1=CC=CC=C1 VQGICXKAKKMXHK-UHFFFAOYSA-N 0.000 claims 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 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 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000002541 furyl group Chemical group 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims 5
- 125000002971 oxazolyl group Chemical group 0.000 claims 5
- 125000004193 piperazinyl group Chemical group 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims 4
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- JNRBMLNWTQWAOR-UHFFFAOYSA-N 1-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-4-[methoxy(phenyl)methyl]pyrrolidin-2-one Chemical compound C=1C=CC=CC=1C(OC)C(CC1=O)CN1C(C=C1F)=CC=C1OC(C1=CC=2OC)=CC=NC1=CC=2OCCCN1CCOCC1 JNRBMLNWTQWAOR-UHFFFAOYSA-N 0.000 claims 2
- FQGNDEQDYLPOOE-UHFFFAOYSA-N 1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-4-(phenoxymethyl)pyrrolidin-2-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N(C(C1)=O)CC1COC1=CC=CC=C1 FQGNDEQDYLPOOE-UHFFFAOYSA-N 0.000 claims 2
- LNRVNLVNYOEOKV-UHFFFAOYSA-N 2-(2,2-dimethylpropylamino)-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C1=CN=C(NCC(C)(C)C)N(C)C1=O LNRVNLVNYOEOKV-UHFFFAOYSA-N 0.000 claims 2
- UAWBXCYNHHRJBH-UHFFFAOYSA-N 2-(4-chloroanilino)-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=C(Cl)C=C1 UAWBXCYNHHRJBH-UHFFFAOYSA-N 0.000 claims 2
- ONSZEUCTVQJHOZ-UHFFFAOYSA-N 2-(4-fluoroanilino)-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=C(F)C=C1 ONSZEUCTVQJHOZ-UHFFFAOYSA-N 0.000 claims 2
- PCXQKKAKSPFWPY-UHFFFAOYSA-N 2-[4-(dimethylamino)anilino]-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=C(N(C)C)C=C1 PCXQKKAKSPFWPY-UHFFFAOYSA-N 0.000 claims 2
- OSPWWUILQRLLCV-UHFFFAOYSA-N 2-anilino-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1h-pyrimidin-6-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1)=O)=CN=C1NC1=CC=CC=C1 OSPWWUILQRLLCV-UHFFFAOYSA-N 0.000 claims 2
- PZNFSAHEDPJDOW-UHFFFAOYSA-N 2-anilino-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=CC=C1 PZNFSAHEDPJDOW-UHFFFAOYSA-N 0.000 claims 2
- WGXDJXZISYQHNK-UHFFFAOYSA-N 2-anilino-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1h-pyrimidin-6-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1)=O)=CN=C1NC1=CC=CC=C1 WGXDJXZISYQHNK-UHFFFAOYSA-N 0.000 claims 2
- BJPFHTCZRZBWRU-UHFFFAOYSA-N 2-anilino-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=CC=C1 BJPFHTCZRZBWRU-UHFFFAOYSA-N 0.000 claims 2
- HBVGKCFCLCCZDQ-UHFFFAOYSA-N 2-benzyl-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1h-pyrimidin-6-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1)=O)=CN=C1CC1=CC=CC=C1 HBVGKCFCLCCZDQ-UHFFFAOYSA-N 0.000 claims 2
- PEGWVOKOYYAQEV-UHFFFAOYSA-N 2-benzyl-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1CC1=CC=CC=C1 PEGWVOKOYYAQEV-UHFFFAOYSA-N 0.000 claims 2
- KJIYUIPYOIACDW-UHFFFAOYSA-N 2-benzyl-5-[3-fluoro-4-[6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1CC1=CC=CC=C1 KJIYUIPYOIACDW-UHFFFAOYSA-N 0.000 claims 2
- TXXALIOZTNGKSD-UHFFFAOYSA-N 2-benzyl-5-[3-fluoro-4-[6-methoxy-7-[3-(1,2,4-triazol-1-yl)propoxy]quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3N=CN=C3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1CC1=CC=CC=C1 TXXALIOZTNGKSD-UHFFFAOYSA-N 0.000 claims 2
- XFEYXKJPGONJJO-UHFFFAOYSA-N 2-benzyl-5-[3-fluoro-4-[6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCN(C)CC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1CC1=CC=CC=C1 XFEYXKJPGONJJO-UHFFFAOYSA-N 0.000 claims 2
- PKIZVMUVKINBQA-RUZDIDTESA-N 2-benzyl-5-[3-fluoro-4-[7-[(2r)-2-hydroxy-3-morpholin-4-ylpropoxy]-6-methoxyquinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OC[C@H](O)CN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1CC1=CC=CC=C1 PKIZVMUVKINBQA-RUZDIDTESA-N 0.000 claims 2
- DPYBSRNXAWRENB-UHFFFAOYSA-N 2-benzyl-5-[3-fluoro-4-[7-[3-(4-hydroxypiperidin-1-yl)propoxy]-6-methoxyquinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCC(O)CC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1CC1=CC=CC=C1 DPYBSRNXAWRENB-UHFFFAOYSA-N 0.000 claims 2
- BJLCYGZYAODRFD-UHFFFAOYSA-N 2-benzyl-5-[4-[7-[3-(4-ethylpiperazin-1-yl)propoxy]-6-methoxyquinolin-4-yl]oxy-3-fluorophenyl]-3-methylpyrimidin-4-one Chemical compound C1CN(CC)CCN1CCCOC1=CC2=NC=CC(OC=3C(=CC(=CC=3)C=3C(N(C)C(CC=4C=CC=CC=4)=NC=3)=O)F)=C2C=C1OC BJLCYGZYAODRFD-UHFFFAOYSA-N 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- CRZXUWRBKQJGCI-UHFFFAOYSA-N 5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-(4-methoxyanilino)-3-methylpyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1NC(N(C1=O)C)=NC=C1C(C=C1F)=CC=C1OC1=CC=NC2=CC(OCCCN3CCOCC3)=C(OC)C=C12 CRZXUWRBKQJGCI-UHFFFAOYSA-N 0.000 claims 2
- BFJLGZQECBDICL-UHFFFAOYSA-N 5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-[hydroxy(phenyl)methyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1C(O)C1=CC=CC=C1 BFJLGZQECBDICL-UHFFFAOYSA-N 0.000 claims 2
- ATTJPKDHHQLOJJ-UHFFFAOYSA-N 5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methyl-2-[(4-methylphenyl)methyl]pyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1CC1=CC=C(C)C=C1 ATTJPKDHHQLOJJ-UHFFFAOYSA-N 0.000 claims 2
- HHXJIDXJDSKDAB-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-(4-fluoro-2-methylanilino)-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=C(F)C=C1C HHXJIDXJDSKDAB-UHFFFAOYSA-N 0.000 claims 2
- DUTNABYDBFVZOA-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-(4-fluoroanilino)-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=C(F)C=C1 DUTNABYDBFVZOA-UHFFFAOYSA-N 0.000 claims 2
- ANFWGFNVWCRIDT-UHFFFAOYSA-N 5-benzyl-3-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1-methylimidazolidine-2,4-dione Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C(N1C)=O)C(=O)C1CC1=CC=CC=C1 ANFWGFNVWCRIDT-UHFFFAOYSA-N 0.000 claims 2
- GKVGOUYEXKHZQS-UHFFFAOYSA-N 5-benzyl-3-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]imidazolidine-2,4-dione Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C1=O)C(=O)NC1CC1=CC=CC=C1 GKVGOUYEXKHZQS-UHFFFAOYSA-N 0.000 claims 2
- AWYLSMAUCAFISX-UHFFFAOYSA-N 6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-(3-fluorophenyl)pyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1NC1=CC=CC(F)=C1 AWYLSMAUCAFISX-UHFFFAOYSA-N 0.000 claims 2
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims 2
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 2
- VIAZJEOTUWKDNJ-UHFFFAOYSA-N n-(2-chlorophenyl)-6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1NC1=CC=CC=C1Cl VIAZJEOTUWKDNJ-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 1
- GSZDMBMHQCASBF-UHFFFAOYSA-N 1-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]imidazolidin-2-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N1CCNC1=O GSZDMBMHQCASBF-UHFFFAOYSA-N 0.000 claims 1
- GSNZVLVKAMDRJA-UHFFFAOYSA-N 1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-4-[ethoxy(phenyl)methyl]pyrrolidin-2-one Chemical compound C1N(C=2C=C(F)C(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)C(=O)CC1C(OCC)C1=CC=CC=C1 GSNZVLVKAMDRJA-UHFFFAOYSA-N 0.000 claims 1
- CLIJECYBLVYACY-UHFFFAOYSA-N 1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-4-[methoxy(phenyl)methyl]pyrrolidin-2-one Chemical compound C1N(C=2C=C(F)C(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)C(=O)CC1C(OC)C1=CC=CC=C1 CLIJECYBLVYACY-UHFFFAOYSA-N 0.000 claims 1
- RIQWKKIUEHRNRW-UHFFFAOYSA-N 1-benzyl-3-[3-fluoro-4-(6-methoxy-7-phenylmethoxyquinolin-4-yl)oxyphenyl]imidazolidine-2,4-dione Chemical compound C1=CN=C2C=C(OCC=3C=CC=CC=3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C1=O)C(=O)CN1CC1=CC=CC=C1 RIQWKKIUEHRNRW-UHFFFAOYSA-N 0.000 claims 1
- ZAIIKQQAXNBEHB-UHFFFAOYSA-N 1-benzyl-3-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]imidazolidine-2,4-dione Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C1=O)C(=O)CN1CC1=CC=CC=C1 ZAIIKQQAXNBEHB-UHFFFAOYSA-N 0.000 claims 1
- RWDIPIUTQWTMLR-UHFFFAOYSA-N 1-benzyl-3-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]imidazolidine-2,4-dione Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N(C1=O)C(=O)CN1CC1=CC=CC=C1 RWDIPIUTQWTMLR-UHFFFAOYSA-N 0.000 claims 1
- RKQJFKDJDBEMPM-UHFFFAOYSA-N 1-benzyl-4-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]piperazine-2,5-dione Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C(C1)=O)CC(=O)N1CC1=CC=CC=C1 RKQJFKDJDBEMPM-UHFFFAOYSA-N 0.000 claims 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- KRHIETAQKLBKDU-UHFFFAOYSA-N 2-(benzylamino)-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NCC1=CC=CC=C1 KRHIETAQKLBKDU-UHFFFAOYSA-N 0.000 claims 1
- MNSLGGWGSWRRID-UHFFFAOYSA-N 2-(cyclohexylamino)-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1CCCCC1 MNSLGGWGSWRRID-UHFFFAOYSA-N 0.000 claims 1
- UBDLWVOLOGMUTH-UHFFFAOYSA-N 2-(cyclopropylmethylamino)-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NCC1CC1 UBDLWVOLOGMUTH-UHFFFAOYSA-N 0.000 claims 1
- DJOMTINYLHXTND-UHFFFAOYSA-N 2-[(1-acetylpiperidin-3-yl)amino]-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1CCCN(C(C)=O)C1 DJOMTINYLHXTND-UHFFFAOYSA-N 0.000 claims 1
- VVMUABJDJYYCJP-UHFFFAOYSA-N 2-[4-(6,7-dimethoxynaphthalen-1-yl)oxy-3-fluorophenyl]-n-(3-methylbutyl)-n-phenylpyrimidin-5-amine Chemical compound C=12C=C(OC)C(OC)=CC2=CC=CC=1OC(C(=C1)F)=CC=C1C(N=C1)=NC=C1N(CCC(C)C)C1=CC=CC=C1 VVMUABJDJYYCJP-UHFFFAOYSA-N 0.000 claims 1
- VCJRGKJOQYDBIT-UHFFFAOYSA-N 2-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-phenylpyrimidin-5-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=C1)=NC=C1NC1=CC=CC=C1 VCJRGKJOQYDBIT-UHFFFAOYSA-N 0.000 claims 1
- CFZUQQDNJOFAHF-UHFFFAOYSA-N 2-[amino(phenyl)methyl]-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1C(N)C1=CC=CC=C1 CFZUQQDNJOFAHF-UHFFFAOYSA-N 0.000 claims 1
- PLLXHDJBOAKSAU-UHFFFAOYSA-N 2-benzyl-5-[3-fluoro-4-(7-hydroxy-6-methoxyquinolin-4-yl)oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(O)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1CC1=CC=CC=C1 PLLXHDJBOAKSAU-UHFFFAOYSA-N 0.000 claims 1
- VFNQFMVWZBQRKK-UHFFFAOYSA-N 2-benzyl-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1h-pyrimidin-6-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1)=O)=CN=C1CC1=CC=CC=C1 VFNQFMVWZBQRKK-UHFFFAOYSA-N 0.000 claims 1
- IKPJWGNTDNCFPS-UHFFFAOYSA-N 2-benzyl-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1CC1=CC=CC=C1 IKPJWGNTDNCFPS-UHFFFAOYSA-N 0.000 claims 1
- LNXBIINVDNXZNZ-UHFFFAOYSA-N 2-benzyl-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1)=O)=C(C)N=C1CC1=CC=CC=C1 LNXBIINVDNXZNZ-UHFFFAOYSA-N 0.000 claims 1
- YVXPEAVBPWBAOO-UHFFFAOYSA-N 2-cyclopentyl-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1C1CCCC1 YVXPEAVBPWBAOO-UHFFFAOYSA-N 0.000 claims 1
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
- IAEBJYIWXMRXQH-UHFFFAOYSA-N 3-[3-fluoro-4-(6-methoxy-7-phenylmethoxyquinolin-4-yl)oxyphenyl]-1-phenylimidazolidine-2,4-dione Chemical compound C1=CN=C2C=C(OCC=3C=CC=CC=3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C1=O)C(=O)CN1C1=CC=CC=C1 IAEBJYIWXMRXQH-UHFFFAOYSA-N 0.000 claims 1
- JPQQPGMRWPOALZ-UHFFFAOYSA-N 3-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1-(2-methylpropyl)imidazolidine-2,4-dione Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N1C(=O)CN(CC(C)C)C1=O JPQQPGMRWPOALZ-UHFFFAOYSA-N 0.000 claims 1
- SWPPHLSFUDWFJG-UHFFFAOYSA-N 3-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-5-methylimidazolidine-2,4-dione Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N1C(=O)NC(C)C1=O SWPPHLSFUDWFJG-UHFFFAOYSA-N 0.000 claims 1
- JAIUPENUOUPZCJ-UHFFFAOYSA-N 3-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1-methyl-6-(pyridin-3-ylamino)pyridin-2-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CC=C1NC1=CC=CN=C1 JAIUPENUOUPZCJ-UHFFFAOYSA-N 0.000 claims 1
- LBCOGFOSKNSLIY-UHFFFAOYSA-N 3-benzyl-1-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]imidazolidine-2,4-dione Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C1=O)CC(=O)N1CC1=CC=CC=C1 LBCOGFOSKNSLIY-UHFFFAOYSA-N 0.000 claims 1
- KDDBMVSIIWOJSD-UHFFFAOYSA-N 4-[2-fluoro-4-(6-phenoxypyridazin-3-yl)phenoxy]-6,7-dimethoxyquinoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1OC1=CC=CC=C1 KDDBMVSIIWOJSD-UHFFFAOYSA-N 0.000 claims 1
- KOSDHWQYVDNUML-UHFFFAOYSA-N 4-[4-(6-benzylpyridazin-3-yl)-2-fluorophenoxy]-6,7-dimethoxyquinoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1CC1=CC=CC=C1 KOSDHWQYVDNUML-UHFFFAOYSA-N 0.000 claims 1
- KJHKYWUGNVFQAU-UHFFFAOYSA-N 4-[4-[6-(2,3-dihydroindol-1-yl)pyridazin-3-yl]-2-fluorophenoxy]-6,7-dimethoxyquinoline Chemical compound C1CC2=CC=CC=C2N1C(N=N1)=CC=C1C(C=C1F)=CC=C1OC1=C(C=C(C(OC)=C2)OC)C2=NC=C1 KJHKYWUGNVFQAU-UHFFFAOYSA-N 0.000 claims 1
- BHGWHEDIMMQUAL-UHFFFAOYSA-N 4-benzoyl-1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyrrolidin-2-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N(C(C1)=O)CC1C(=O)C1=CC=CC=C1 BHGWHEDIMMQUAL-UHFFFAOYSA-N 0.000 claims 1
- AIOLWBDAHUBWSJ-UHFFFAOYSA-N 4-benzyl-1-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]pyrrolidin-2-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C(C1)=O)CC1CC1=CC=CC=C1 AIOLWBDAHUBWSJ-UHFFFAOYSA-N 0.000 claims 1
- NFDGOCCVTSNGMJ-UHFFFAOYSA-N 4-benzyl-1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyrrolidin-2-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N(C(C1)=O)CC1CC1=CC=CC=C1 NFDGOCCVTSNGMJ-UHFFFAOYSA-N 0.000 claims 1
- QZCOGTMXBBPDKK-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-(2-fluoroanilino)-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=CC=C1F QZCOGTMXBBPDKK-UHFFFAOYSA-N 0.000 claims 1
- DRSPEQIWHFQYLU-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-(3-fluoroanilino)-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=CC(F)=C1 DRSPEQIWHFQYLU-UHFFFAOYSA-N 0.000 claims 1
- BAOYZTZXPNHDJH-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-(4-fluoro-2-methylanilino)-1h-pyrimidin-6-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1)=O)=CN=C1NC1=CC=C(F)C=C1C BAOYZTZXPNHDJH-UHFFFAOYSA-N 0.000 claims 1
- BHAYJGAKIFGZLH-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-(4-fluorophenyl)-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1C1=CC=C(F)C=C1 BHAYJGAKIFGZLH-UHFFFAOYSA-N 0.000 claims 1
- KOECFFZFKPDYLG-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-(1-phenylethylamino)pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC(C)C1=CC=CC=C1 KOECFFZFKPDYLG-UHFFFAOYSA-N 0.000 claims 1
- OLWUKIJTPTYBPQ-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-(2-methylpropylamino)pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C1=CN=C(NCC(C)C)N(C)C1=O OLWUKIJTPTYBPQ-UHFFFAOYSA-N 0.000 claims 1
- CRCOOKFSKGFKET-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-(2-phenylethylamino)pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NCCC1=CC=CC=C1 CRCOOKFSKGFKET-UHFFFAOYSA-N 0.000 claims 1
- DFAMEFWFWJDHFS-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-(4-methylanilino)pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=C(C)C=C1 DFAMEFWFWJDHFS-UHFFFAOYSA-N 0.000 claims 1
- GWHVLWCXGCNUPG-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-(n-methylanilino)pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1N(C)C1=CC=CC=C1 GWHVLWCXGCNUPG-UHFFFAOYSA-N 0.000 claims 1
- AVOGYRSPBZSTKL-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-(pyridin-2-ylamino)pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=CC=N1 AVOGYRSPBZSTKL-UHFFFAOYSA-N 0.000 claims 1
- WMASYRDUQKPLKQ-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-[(1-propylpiperidin-3-yl)amino]pyrimidin-4-one Chemical compound C1N(CCC)CCCC1NC(N(C1=O)C)=NC=C1C(C=C1F)=CC=C1OC1=CC=NC2=CC(OC)=C(OC)C=C12 WMASYRDUQKPLKQ-UHFFFAOYSA-N 0.000 claims 1
- NJVQGOLGWAYYDC-GOSISDBHSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-[(1r)-1-phenylethyl]pyrimidin-4-one Chemical compound C1([C@@H](C)C2=NC=C(C(N2C)=O)C2=CC=C(C(=C2)F)OC=2C=CN=C3C=C(C(=CC3=2)OC)OC)=CC=CC=C1 NJVQGOLGWAYYDC-GOSISDBHSA-N 0.000 claims 1
- WKDSRSWTJRXFHC-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-[4-(trifluoromethyl)anilino]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=C(C(F)(F)F)C=C1 WKDSRSWTJRXFHC-UHFFFAOYSA-N 0.000 claims 1
- ZTEAFIWGOGIXKV-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-[[1-(2,2,2-trifluoroacetyl)piperidin-3-yl]amino]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1CCCN(C(=O)C(F)(F)F)C1 ZTEAFIWGOGIXKV-UHFFFAOYSA-N 0.000 claims 1
- FQLCYEYJIXJYKU-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-[n-(3-methylbutyl)anilino]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1N(CCC(C)C)C1=CC=CC=C1 FQLCYEYJIXJYKU-UHFFFAOYSA-N 0.000 claims 1
- BKSWYOHROKZGQJ-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-methylsulfanylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C1=CN=C(SC)N(C)C1=O BKSWYOHROKZGQJ-UHFFFAOYSA-N 0.000 claims 1
- YSOJLVJKEOFWDK-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-phenylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1C1=CC=CC=C1 YSOJLVJKEOFWDK-UHFFFAOYSA-N 0.000 claims 1
- UCWBIBYVEQMUJR-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-pyrrolidin-1-ylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1N1CCCC1 UCWBIBYVEQMUJR-UHFFFAOYSA-N 0.000 claims 1
- FVCWENINFRMZBW-UHFFFAOYSA-N 6,7-dimethoxy-4-(6-methyl-2-thiophen-3-ylpyridin-3-yl)oxyquinoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC1=CC=C(C)N=C1C=1C=CSC=1 FVCWENINFRMZBW-UHFFFAOYSA-N 0.000 claims 1
- WGYKCOIIEWQAEN-UHFFFAOYSA-N 6-[3-chloro-4-(6,7-dimethoxyquinolin-4-yl)oxyphenyl]-n-phenylpyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)Cl)=CC=C1C(N=N1)=CC=C1NC1=CC=CC=C1 WGYKCOIIEWQAEN-UHFFFAOYSA-N 0.000 claims 1
- MBUBVYJEWQXONT-UHFFFAOYSA-N 6-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-n-phenylpyridazin-3-amine Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1NC1=CC=CC=C1 MBUBVYJEWQXONT-UHFFFAOYSA-N 0.000 claims 1
- LAMJVDBQSQOXNA-UHFFFAOYSA-N 6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-(2,2,2-trifluoroethyl)pyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C1=CC=C(NCC(F)(F)F)N=N1 LAMJVDBQSQOXNA-UHFFFAOYSA-N 0.000 claims 1
- XTGUDWBGLVVSHS-UHFFFAOYSA-N 6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-(2,3-dimethylphenyl)pyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1NC1=CC=CC(C)=C1C XTGUDWBGLVVSHS-UHFFFAOYSA-N 0.000 claims 1
- KISGDJNTHJAZCC-UHFFFAOYSA-N 6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-(2-methoxyphenyl)pyridazin-3-amine Chemical compound COC1=CC=CC=C1NC1=CC=C(C=2C=C(F)C(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)N=N1 KISGDJNTHJAZCC-UHFFFAOYSA-N 0.000 claims 1
- WRMPBGABSQUUSW-UHFFFAOYSA-N 6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-(2-methylphenyl)pyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1NC1=CC=CC=C1C WRMPBGABSQUUSW-UHFFFAOYSA-N 0.000 claims 1
- NZFGMRYVJOQEGQ-UHFFFAOYSA-N 6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-methyl-n-phenylpyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1N(C)C1=CC=CC=C1 NZFGMRYVJOQEGQ-UHFFFAOYSA-N 0.000 claims 1
- MOKHEEYKZMBRIA-UHFFFAOYSA-N 6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-phenylpyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1NC1=CC=CC=C1 MOKHEEYKZMBRIA-UHFFFAOYSA-N 0.000 claims 1
- FOIXQIWEHZXQNC-UHFFFAOYSA-N 6-[4-(6,7-dimethoxyquinolin-4-yl)oxyphenyl]-n-phenylpyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1)=CC=C1C(N=N1)=CC=C1NC1=CC=CC=C1 FOIXQIWEHZXQNC-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- CQKRIQRZTAMFET-UHFFFAOYSA-N FC=1C=C(C=CC=1OC1=CC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)N1C(N(CC1=O)C(C)C1=CC=CC=C1)=O Chemical compound FC=1C=C(C=CC=1OC1=CC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)N1C(N(CC1=O)C(C)C1=CC=CC=C1)=O CQKRIQRZTAMFET-UHFFFAOYSA-N 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940125697 hormonal agent Drugs 0.000 claims 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
- 229940124452 immunizing agent Drugs 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- YZOVIOYZXYPRBA-UHFFFAOYSA-N n-(3-chlorophenyl)-6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1NC1=CC=CC(Cl)=C1 YZOVIOYZXYPRBA-UHFFFAOYSA-N 0.000 claims 1
- DOANCNPFSRWFRV-UHFFFAOYSA-N n-[1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-5-oxopyrrolidin-3-yl]benzamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N(C(C1)=O)CC1NC(=O)C1=CC=CC=C1 DOANCNPFSRWFRV-UHFFFAOYSA-N 0.000 claims 1
- HVFXCDMQCAJEOI-UHFFFAOYSA-N n-cyclopentyl-6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1NC1CCCC1 HVFXCDMQCAJEOI-UHFFFAOYSA-N 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 0 Cc1c(cc(**)c(**)n2)c2ncc1 Chemical compound Cc1c(cc(**)c(**)n2)c2ncc1 0.000 description 4
- AXSSJSFXWMOTEN-UHFFFAOYSA-N CC(C1)CN(C)C1=O Chemical compound CC(C1)CN(C)C1=O AXSSJSFXWMOTEN-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63227104P | 2004-11-30 | 2004-11-30 | |
| PCT/US2005/042935 WO2006060318A2 (en) | 2004-11-30 | 2005-11-29 | Quinolines and quinazoline analogs and their use as medicaments for treating cancer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008521900A JP2008521900A (ja) | 2008-06-26 |
| JP2008521900A5 true JP2008521900A5 (enExample) | 2009-01-22 |
Family
ID=36215740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007544417A Withdrawn JP2008521900A (ja) | 2004-11-30 | 2005-11-29 | キノリン及びキナゾリン類似体並びにがん治療のための医薬としてのその使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7652009B2 (enExample) |
| EP (1) | EP1827434B1 (enExample) |
| JP (1) | JP2008521900A (enExample) |
| AU (1) | AU2005312048B2 (enExample) |
| CA (1) | CA2587642C (enExample) |
| ES (1) | ES2450566T3 (enExample) |
| MX (1) | MX2007006230A (enExample) |
| WO (1) | WO2006060318A2 (enExample) |
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602005009907D1 (de) * | 2004-11-16 | 2008-11-06 | T & S Brass & Bronze Works Inc | Sprühventilanordnung für Vorspülungseinheiten. |
| EP1924262B1 (en) | 2005-08-22 | 2011-11-16 | Melior Pharmaceuticals I, Inc. | Methods and formulations for modulating lyn kinase activity and treating related disorders |
| PL1889836T3 (pl) * | 2005-08-24 | 2013-10-31 | Eisai R&D Man Co Ltd | Nowa pochodna pirydyny i pochodna pirymidyny (3) |
| AR059246A1 (es) * | 2006-01-30 | 2008-03-19 | Array Biopharma Inc | Compuestos heterobiciclicos de tiofeno y metodos de uso |
| WO2007099323A2 (en) * | 2006-03-02 | 2007-09-07 | Astrazeneca Ab | Quinoline derivatives |
| UY30183A1 (es) * | 2006-03-02 | 2007-10-31 | Astrazeneca Ab | Derivados de quinolina |
| MX2008011220A (es) * | 2006-03-07 | 2008-09-11 | Array Biopharma Inc | Compuestos de pirazol heterobiciclicos y metodos de uso. |
| US20110053931A1 (en) * | 2006-06-08 | 2011-03-03 | John Gaudino | Quinoline compounds and methods of use |
| CN101454311B (zh) * | 2006-08-23 | 2013-03-27 | 卫材R&D管理有限公司 | 苯氧基吡啶衍生物的盐和其结晶及其制备方法 |
| US7790885B2 (en) * | 2006-08-31 | 2010-09-07 | Eisai R&D Management Co., Ltd. | Process for preparing phenoxypyridine derivatives |
| WO2008079291A2 (en) | 2006-12-20 | 2008-07-03 | Amgen Inc. | Substituted heterocycles and methods of use |
| JP2010518860A (ja) * | 2007-02-20 | 2010-06-03 | メリオール・ファーマスーティカルズ・ワン・インコーポレイテッド | Ｌｙｎキナーゼの活性化剤の同定方法 |
| AU2008231384B2 (en) * | 2007-03-23 | 2011-09-15 | Amgen Inc. | Heterocyclic compounds and their use |
| JP5550546B2 (ja) * | 2007-04-13 | 2014-07-16 | ケムジェネックス・ファーマシューティカルズ・インコーポレイテッド | 経口セファロタキシン剤形 |
| CA2693809A1 (en) * | 2007-07-23 | 2009-01-29 | Melior Discovery, Inc. | Methods of activating irs-1 and akt |
| JP2009132660A (ja) * | 2007-11-30 | 2009-06-18 | Eisai R & D Management Co Ltd | 食道癌治療用組成物 |
| US20090227556A1 (en) * | 2008-01-31 | 2009-09-10 | Eisai R&D Management Co., Ltd. | Receptor tyrosine kinase inhibitors comprising pyridine and pyrimidine derivatives |
| JPWO2009104520A1 (ja) * | 2008-02-18 | 2011-06-23 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | フェノキシピリジン誘導体の製造方法（２） |
| WO2009109035A1 (en) * | 2008-03-05 | 2009-09-11 | Methylgene Inc. | Inhibitors of protein tyrosine kinase activity |
| US8552184B2 (en) * | 2008-07-03 | 2013-10-08 | Melior Pharmaceuticals I, Inc. | Compounds and methods for treating disorders related to glucose metabolism |
| CA2740746A1 (en) * | 2008-10-14 | 2010-04-22 | Ning Xi | Compounds comprising a spiro-ring and and methods of use |
| EP2408300B1 (en) * | 2009-03-21 | 2016-05-11 | Sunshine Lake Pharma Co., Ltd. | Amino ester derivatives, salts thereof and methods of use |
| WO2011114103A1 (en) * | 2010-03-18 | 2011-09-22 | Biolipox Ab | Pyrimidinones for use as medicaments |
| AR081331A1 (es) * | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| EP2560488B1 (en) | 2010-04-23 | 2015-10-28 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| US20130158055A1 (en) | 2010-05-28 | 2013-06-20 | Andrew G. Reaume | Prevention Of Pancreatic Beta Cell Degeneration |
| CA2802644C (en) | 2010-06-25 | 2017-02-21 | Eisai R & D Management Co., Ltd. | Antitumor agent using compounds having kinase inhibitory effect in combination |
| AU2012313888B2 (en) | 2011-09-27 | 2016-03-31 | Novartis Ag | 3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant IDH |
| UY34632A (es) | 2012-02-24 | 2013-05-31 | Novartis Ag | Compuestos de oxazolidin- 2- ona y usos de los mismos |
| WO2013180949A1 (en) * | 2012-05-27 | 2013-12-05 | Ning Xi | Substituted quinoline compounds and methods of use |
| TWI520962B (zh) * | 2012-06-29 | 2016-02-11 | As the c-Met tyrosine kinase inhibitors novel fused pyridine derivatives | |
| CN104507930B (zh) * | 2012-06-29 | 2017-10-10 | 贝达药业股份有限公司 | 作为c‑Met酪氨酸激酶抑制剂的新型稠合吡啶衍生物 |
| US9296733B2 (en) | 2012-11-12 | 2016-03-29 | Novartis Ag | Oxazolidin-2-one-pyrimidine derivative and use thereof for the treatment of conditions, diseases and disorders dependent upon PI3 kinases |
| AU2013364953A1 (en) | 2012-12-21 | 2015-04-30 | Eisai R&D Management Co., Ltd. | Amorphous form of quinoline derivative, and method for producing same |
| CA2900652C (en) | 2013-02-15 | 2021-05-04 | 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 (zh) | 2013-02-20 | 2018-04-17 | 卡拉制药公司 | 治疗性化合物和其用途 |
| KR20150131224A (ko) | 2013-03-14 | 2015-11-24 | 노파르티스 아게 | 돌연변이 idh의 억제제로서의 3-피리미딘-4-일-옥사졸리딘-2-온 |
| CN105264380B (zh) | 2013-05-14 | 2017-09-05 | 卫材R&D管理有限公司 | 用于预测和评价子宫内膜癌受试者对乐伐替尼化合物响应性的生物标志 |
| US9890173B2 (en) | 2013-11-01 | 2018-02-13 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| WO2015066482A1 (en) | 2013-11-01 | 2015-05-07 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| EP2974729A1 (en) | 2014-07-17 | 2016-01-20 | Abivax | Quinoline derivatives for use in the treatment of inflammatory diseases |
| CA2957005C (en) | 2014-08-28 | 2021-10-12 | Eisai R&D Management Co., Ltd. | High-purity quinoline derivative and method for manufacturing same |
| SG11201706630UA (en) | 2015-02-25 | 2017-09-28 | Eisai R&D Man Co Ltd | Method for suppressing bitterness of quinoline derivative |
| WO2016140717A1 (en) | 2015-03-04 | 2016-09-09 | Merck Sharp & Dohme Corp. | Combination of a pd-1 antagonist and a vegfr/fgfr/ret tyrosine kinase inhibitor for treating cancer |
| BR112017027227B1 (pt) | 2015-06-16 | 2023-12-12 | Eisai R&D Management Co., Ltd | Agente anti-câncer |
| JP6553726B2 (ja) | 2015-08-20 | 2019-07-31 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 腫瘍治療剤 |
| AU2017324713B2 (en) | 2016-09-08 | 2020-08-13 | KALA BIO, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| AU2017324716B2 (en) | 2016-09-08 | 2020-08-13 | KALA BIO, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| MX2019002629A (es) | 2016-09-08 | 2019-10-07 | Kala Pharmaceuticals Inc | Formas cristalinas de compuestos terapéuticos y usos de los mismos. |
| CN106543145B (zh) * | 2016-10-28 | 2019-07-19 | 山西医科大学 | c-Met激酶抑剂3-(4-氟苯基)嘧啶酮-5-甲酸酰胺衍生物、制备方法与应用 |
| KR102279347B1 (ko) * | 2016-12-15 | 2021-07-21 | 한국생명공학연구원 | 피리딘계 화합물을 유효성분으로 함유하는 dyrk 관련 질환의 예방 또는 치료용 약학적 조성물 |
| US12303505B2 (en) | 2017-02-08 | 2025-05-20 | Eisai R&D Management Co., Ltd. | Tumor-treating pharmaceutical composition |
| AU2018250795B2 (en) | 2017-04-10 | 2022-02-10 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Treatment of adipocytes |
| BR112019023064A2 (pt) | 2017-05-16 | 2020-06-09 | Eisai R&D Man Co Ltd | tratamento de carcinoma hepatocelular |
| KR102724968B1 (ko) * | 2018-03-21 | 2024-10-31 | 수조우 푸허 바이오파마 컴퍼니 리미티드 | Shp2 억제제 및 이의 용도 |
| CN112867539B (zh) | 2018-08-31 | 2024-08-06 | 赛特凯恩蒂克公司 | 心脏肌小节抑制剂 |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| AU2019387367A1 (en) | 2018-11-30 | 2021-06-10 | Nuvation Bio Inc. | Diarylhydantoin compounds and methods of use thereof |
| EP3669873A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Quinoline derivatives for use ine the traeatment of inflammation diseases |
| EP4025570A4 (en) * | 2019-09-06 | 2022-11-02 | ONO Pharmaceutical Co., Ltd. | HYDANTOINDIVATIVES |
| TW202302594A (zh) | 2021-03-04 | 2023-01-16 | 美商胞質動力學公司 | 心臟肌節抑制劑 |
| WO2024158863A1 (en) * | 2023-01-25 | 2024-08-02 | The Rockefeller University | Sulfonamide-1h-pyrrole-2-carboxamide inhibitors of sars-cov-2 nsp14 methyltransferase and derivatives thereof |
Family Cites Families (80)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3755332A (en) | 1971-07-01 | 1973-08-28 | Ciba Geigy Corp | Substituted 4 indazolaminoquinolines |
| JPS63145272A (ja) | 1986-12-09 | 1988-06-17 | Morishita Seiyaku Kk | ４，５−ジヒドロ−６−（４−置換フエニル）−３（２ｈ）−ピリダジノン誘導体 |
| US4916135A (en) | 1989-05-08 | 1990-04-10 | Hoechst Roussel Pharmaceuticals Inc. | N-heteroaryl-4-quinolinamines |
| US5521184A (en) | 1992-04-03 | 1996-05-28 | Ciba-Geigy Corporation | Pyrimidine derivatives and processes for the preparation thereof |
| GB9323290D0 (en) | 1992-12-10 | 1994-01-05 | 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 |
| WO1996023774A1 (en) | 1995-01-31 | 1996-08-08 | Zenyaku Kogyo Kabushiki Kaisha | Thioquinoline derivatives |
| GB9505651D0 (en) | 1995-03-21 | 1995-05-10 | Agrevo Uk Ltd | AgrEvo UK Limited |
| GB9505702D0 (en) | 1995-03-21 | 1995-05-10 | Agrevo Uk Ltd | Fungicidal compounds |
| GB9508538D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| US5747498A (en) | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| GB9514265D0 (en) | 1995-07-13 | 1995-09-13 | Wellcome Found | Hetrocyclic compounds |
| WO1997017329A1 (en) | 1995-11-07 | 1997-05-15 | Kirin Beer Kabushiki Kaisha | Quinoline derivatives and quinazoline derivatives inhibiting autophosphorylation of growth factor receptor originating in platelet and pharmaceutical compositions containing the same |
| JPH10512896A (ja) | 1995-11-14 | 1998-12-08 | フアルマシア・エ・アツプジヨン・エツセ・ピー・アー | アリールおよびヘテロアリールプリン化合物 |
| 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 (de) | 1996-04-15 | 1997-10-16 | Hoechst Schering Agrevo Gmbh | Substituierte Pyridine/Pyrimidine, Verfahren zu ihrer Herstellung, und ihre Verwendung als Schädlingsbekämpfungsmittel |
| CO4950519A1 (es) | 1997-02-13 | 2000-09-01 | Novartis Ag | Ftalazinas, preparaciones farmaceuticas que las comprenden y proceso para su preparacion |
| JP4495257B2 (ja) | 1997-02-19 | 2010-06-30 | バーレツクス ラボラトリーズ インコーポレーテツド | Ｎｏｓ抑制剤としてのｎ−複素環誘導体 |
| JP4194678B2 (ja) | 1997-11-28 | 2008-12-10 | キリンファーマ株式会社 | キノリン誘導体およびそれを含む医薬組成物 |
| GB9800575D0 (en) | 1998-01-12 | 1998-03-11 | Glaxo Group Ltd | Heterocyclic compounds |
| RS49779B (sr) | 1998-01-12 | 2008-06-05 | Glaxo Group Limited, | Biciklična heteroaromatična jedinjenja kao inhibitori protein tirozin kinaze |
| ES2324846T3 (es) | 1998-03-04 | 2009-08-17 | Bristol-Myers Squibb Company | Inhibidores de la proteina tirosina quinasa de imidazopirazina heterociclo-sustituida. |
| ATE293102T1 (de) | 1998-04-23 | 2005-04-15 | Takeda Pharmaceutical | Naphthalene derivate ,ihre herstellung und verwendung |
| AU4317399A (en) | 1998-05-28 | 1999-12-13 | Parker Hughes Institute | Quinazolines for treating brain tumor |
| IL139934A0 (en) | 1998-05-29 | 2002-02-10 | Sugen Inc | Pyrrole substituted 2-indolinone derivatives and pharmaceutical compositions containing the same |
| UA60365C2 (uk) | 1998-06-04 | 2003-10-15 | Пфайзер Продактс Інк. | Похідні ізотіазолу, спосіб їх одержання, фармацевтична композиція та спосіб лікування гіперпроліферативного захворювання у ссавця |
| CA2336848A1 (en) | 1998-07-10 | 2000-01-20 | Merck & Co., Inc. | Novel angiogenesis inhibitors |
| EP1105378B1 (en) | 1998-08-21 | 2005-03-30 | Parker Hughes Institute | Quinazoline derivatives |
| EP1109555A4 (en) | 1998-08-31 | 2001-11-21 | Merck & Co Inc | Novel angiogenesis inhibitors |
| CA2359244C (en) | 1999-01-13 | 2013-10-08 | Bayer Healthcare Llc | .omega.-carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors |
| CA2361057C (en) | 1999-01-22 | 2010-04-06 | Kazuo Kubo | Quinoline derivatives and quinazoline derivatives |
| BRPI0017548B8 (pt) | 1999-02-10 | 2023-05-02 | Astrazeneca Ab | Composto |
| GB9904103D0 (en) | 1999-02-24 | 1999-04-14 | Zeneca Ltd | Quinoline derivatives |
| US6258820B1 (en) | 1999-03-19 | 2001-07-10 | Parker Hughes Institute | Synthesis and anti-tumor activity of 6,7-dialkoxy-4-phenylamino-quinazolines |
| JP4673977B2 (ja) | 1999-03-30 | 2011-04-20 | ノバルティス アーゲー | 炎症性疾患治療用フタラジン誘導体 |
| EE200100528A (et) | 1999-04-12 | 2003-02-17 | Aventis Pharma Limited | Asendatud bitsükliline heteroarüülühend, seda sisaldav farmatseutiline kompositsioon ning nende raviotstarbeline kasutamine |
| JP2003509497A (ja) | 1999-09-21 | 2003-03-11 | アストラゼネカ アクチボラグ | キナゾリン化合物とそれらを含有する医薬組成物 |
| CN100376567C (zh) | 1999-11-05 | 2008-03-26 | 阿斯特拉曾尼卡有限公司 | 作为vegf抑制剂的喹唑啉衍生物 |
| DK1233943T3 (da) | 1999-11-24 | 2011-08-15 | Sugen Inc | Ioniserbare indolinon derivater og anvendelse deraf som PTK ligander |
| US6515004B1 (en) | 1999-12-15 | 2003-02-04 | Bristol-Myers Squibb Company | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
| AU2001250850A1 (en) | 2000-03-17 | 2001-10-03 | Dupont Pharmaceuticals Company | Beta-amino acid derivatives as inhibitors of matrix metalloproteases and tnf-alpha |
| CN1481377A (zh) | 2000-03-17 | 2004-03-10 | ����˹�ж�-����˹˹����ҩƷ��˾ | 作为基质金属蛋白酶和TNF-α的抑制剂的环β-氨基酸衍生物 |
| US6630500B2 (en) | 2000-08-25 | 2003-10-07 | Cephalon, Inc. | Selected fused pyrrolocarbazoles |
| ES2266258T3 (es) | 2000-09-15 | 2007-03-01 | Vertex Pharmaceuticals Incorporated | Compuestos de pirazol utiles como inhibidores de proteina cinasas. |
| AU2001292138A1 (en) | 2000-10-13 | 2002-04-22 | Astrazeneca Ab | Quinazoline derivatives with anti-tumour activity |
| EP1415987B1 (en) | 2000-10-20 | 2007-02-28 | Eisai R&D Management Co., Ltd. | Nitrogenous aromatic ring compounds as anti cancer agents |
| ES2556946T3 (es) | 2000-12-21 | 2016-01-21 | Novartis Ag | Pirimidinaminas como moduladores de la angiogénesis |
| US6995162B2 (en) | 2001-01-12 | 2006-02-07 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
| US7102009B2 (en) | 2001-01-12 | 2006-09-05 | Amgen Inc. | Substituted amine derivatives and methods of use |
| US7105682B2 (en) | 2001-01-12 | 2006-09-12 | Amgen Inc. | Substituted amine derivatives and methods of use |
| US20020147198A1 (en) | 2001-01-12 | 2002-10-10 | Guoqing Chen | Substituted arylamine derivatives and methods of use |
| US6878714B2 (en) | 2001-01-12 | 2005-04-12 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
| US20030165873A1 (en) | 2001-03-02 | 2003-09-04 | Come Jon H. | Three hybrid assay system |
| JP4329003B2 (ja) | 2001-03-23 | 2009-09-09 | バイエル コーポレイション | Ｒｈｏキナーゼ阻害剤 |
| ATE383858T1 (de) | 2001-06-06 | 2008-02-15 | Aventis Pharma Ltd | Substituierte tetrhydroisochinolin-derivate zur behandlung von entzündlichen erkrankungen |
| CA2454538A1 (en) * | 2001-06-22 | 2003-01-03 | Kirin Beer Kabushiki Kaisha | Quinoline derivatives and quinazoline derivatives capable of inhibiting autophosphorylation of hepatocyte growth factor receptors, and pharmaceutical composition comprising the same |
| SE0102439D0 (sv) | 2001-07-05 | 2001-07-05 | Astrazeneca Ab | New compounds |
| JP2005515176A (ja) | 2001-11-03 | 2005-05-26 | アストラゼネカ アクチボラグ | 抗腫瘍剤としてのキナゾリン誘導体 |
| GB0126433D0 (en) | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| CN1625555A (zh) | 2002-02-01 | 2005-06-08 | 阿斯特拉曾尼卡有限公司 | 喹唑啉化合物 |
| US7645878B2 (en) | 2002-03-22 | 2010-01-12 | Bayer Healthcare Llc | Process for preparing quinazoline Rho-kinase inhibitors and intermediates thereof |
| ATE447404T1 (de) | 2002-03-29 | 2009-11-15 | Novartis Vaccines & Diagnostic | Substituierte benzazole und ihre verwendung als raf-kinase-hemmer |
| US7307088B2 (en) | 2002-07-09 | 2007-12-11 | Amgen Inc. | Substituted anthranilic amide derivatives and methods of use |
| TWI329112B (en) | 2002-07-19 | 2010-08-21 | Bristol Myers Squibb Co | Novel inhibitors of kinases |
| CN1688549A (zh) * | 2002-08-23 | 2005-10-26 | 麒麟麦酒株式会社 | 具有TGFβ抑制活性的化合物和含所述化合物的药用组合物 |
| AU2003255482A1 (en) * | 2002-10-02 | 2004-04-23 | Merck Patent Gmbh | Use of 4 amino-quinazolines as anti cancer agents |
| WO2004037784A2 (en) * | 2002-10-21 | 2004-05-06 | Irm Llc | Pyrrolidones with anti-hiv activity |
| AR041992A1 (es) | 2002-11-06 | 2005-06-08 | Smithkline Beecham Corp | Compuesto de piridinil benzoheterociclico, composicion farmaceutica que lo comprende y su uso para prepararla |
| GB0226724D0 (en) | 2002-11-15 | 2002-12-24 | Merck Sharp & Dohme | Therapeutic agents |
| WO2004078114A2 (en) | 2003-02-28 | 2004-09-16 | Encysive Pharmaceuticals Inc. | Pyridine, pyrimidine, quinoline, quinazoline, and naphthalene urotensin-ii receptor antagonists. |
| AU2004221812B2 (en) | 2003-03-19 | 2010-02-18 | Exelixis Inc. | Tie-2 modulators and methods of use |
| US7531553B2 (en) | 2003-03-21 | 2009-05-12 | Amgen Inc. | Heterocyclic compounds and methods of use |
| GB0310401D0 (en) | 2003-05-07 | 2003-06-11 | Astrazeneca Ab | Therapeutic agent |
| CA2536788A1 (en) | 2003-08-29 | 2005-03-10 | Pfizer Inc. | Naphthalene carboxamides and their derivatives useful as new anti-angiogenic agents |
| CA2744997A1 (en) | 2003-09-26 | 2005-04-07 | Exelixis, Inc. | C-met modulators and method of use |
| US7691866B2 (en) | 2003-10-16 | 2010-04-06 | Novartis Vaccines And Diagnostics, Inc. | 2,6-disubstituted quinazolines, quinoxalines, quinolines and isoquinolines and methods of their use as inhibitors of Raf kinase |
| JP4932495B2 (ja) | 2004-01-23 | 2012-05-16 | アムゲン インコーポレイテッド | 化合物及び使用方法 |
| CA2553433A1 (en) | 2004-01-23 | 2005-08-11 | Amgen Inc. | Quinoline quinazoline pyridine and pyrimidine compounds and their use in the treatment of inflammation angiogenesis and cancer |
| WO2005080377A1 (ja) * | 2004-02-20 | 2005-09-01 | Kirin Beer Kabushiki Kaisha | TGFβ阻害活性を有する化合物およびそれを含んでなる医薬組成物 |
-
2005
- 2005-11-29 US US11/289,659 patent/US7652009B2/en active Active
- 2005-11-29 AU AU2005312048A patent/AU2005312048B2/en not_active Ceased
- 2005-11-29 CA CA2587642A patent/CA2587642C/en not_active Expired - Fee Related
- 2005-11-29 JP JP2007544417A patent/JP2008521900A/ja not_active Withdrawn
- 2005-11-29 MX MX2007006230A patent/MX2007006230A/es not_active Application Discontinuation
- 2005-11-29 WO PCT/US2005/042935 patent/WO2006060318A2/en not_active Ceased
- 2005-11-29 ES ES05848812.3T patent/ES2450566T3/es not_active Expired - Lifetime
- 2005-11-29 EP EP05848812.3A patent/EP1827434B1/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2587642A1 (en) | Substituted heterocycles and methods of use | |
| JP2011520908A5 (enExample) | ||
| HRP20231310T1 (hr) | Heteroarilaminopirimidin amidni inhibitori autofagije i postupci njihove primjene | |
| JP2016532656A5 (enExample) | ||
| JP2008525502A5 (enExample) | ||
| CA2605680A1 (en) | Substituted amide derivatives as protein kinase inhibitors | |
| RU2375352C2 (ru) | Амидные производные | |
| JP2022531932A5 (enExample) | ||
| JP2004536066A5 (enExample) | ||
| JP2023501253A5 (enExample) | ||
| JP2019070032A5 (enExample) | ||
| JP2019537571A5 (enExample) | ||
| JP2022531801A5 (enExample) | ||
| HRP20141259T1 (hr) | Supstituirani izokinolinoni i kinazolinoni | |
| JP2022125283A5 (enExample) | ||
| JP2006500348A5 (enExample) | ||
| RU2005122932A (ru) | Производные бензазепина для лечения неврологических нарушений | |
| CA2440238A1 (en) | Novel amines as histamine-3 receptor ligands and their therapeutic applications | |
| SI2790705T1 (en) | Use of activity inhibitors or PI3K function | |
| HRP20130865T1 (hr) | Derivati pirazol piridina kao inhibitori nadph oksidaze | |
| JP2007505878A5 (enExample) | ||
| RU2008126398A (ru) | Производные гетероарилзамещенного пиперидина в качестве ингибиторов печеночной карнитин пальмитоилтрансферазы (l-cpti) | |
| JP2007505874A5 (enExample) | ||
| JP2017510554A5 (enExample) | ||
| JP2006512412A5 (ja) | 神経系の疾患の治療用のベンズアゼピン誘導体 |