JP2008521900A - 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 - Google Patents

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Publication number

JP2008521900A

JP2008521900A JP2007544417A JP2007544417A JP2008521900A JP 2008521900 A JP2008521900 A JP 2008521900A JP 2007544417 A JP2007544417 A JP 2007544417A JP 2007544417 A JP2007544417 A JP 2007544417A JP 2008521900 A JP2008521900 A JP 2008521900A

Authority

JP

Japan

Prior art keywords

phenyl

methoxy

methyl

oxy

quinolinyl

Prior art date

2004-11-30

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Withdrawn

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• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 55
• 201000011510 cancer Diseases 0.000 title claims abstract description 19
• 239000003814 drug Substances 0.000 title claims description 21
• 238000011282 treatment Methods 0.000 title abstract description 64
• 229940111121 antirheumatic drug quinolines Drugs 0.000 title description 3
• 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
• 150000003248 quinolines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 354
• 238000000034 method Methods 0.000 claims abstract description 70
• 125000003118 aryl group Chemical group 0.000 claims abstract description 49
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 49
• 101000898034 Homo sapiens Hepatocyte growth factor Proteins 0.000 claims abstract description 48
• 102100021866 Hepatocyte growth factor Human genes 0.000 claims abstract description 47
• 101001076408 Homo sapiens Interleukin-6 Proteins 0.000 claims abstract description 46
• 101000868152 Homo sapiens Son of sevenless homolog 1 Proteins 0.000 claims abstract description 46
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 39
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
• 230000001404 mediated effect Effects 0.000 claims abstract description 7
• -1 piperazin-4-yl Chemical group 0.000 claims description 357
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
• 125000000623 heterocyclic group Chemical group 0.000 claims description 69
• 125000000217 alkyl group Chemical group 0.000 claims description 68
• 229910052739 hydrogen Chemical group 0.000 claims description 53
• 150000003839 salts Chemical class 0.000 claims description 47
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 35
• 229910052727 yttrium Inorganic materials 0.000 claims description 32
• 125000003545 alkoxy group Chemical group 0.000 claims description 30
• 125000003342 alkenyl group Chemical group 0.000 claims description 29
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 125000000304 alkynyl group Chemical group 0.000 claims description 27
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 27
• 125000001188 haloalkyl group Chemical group 0.000 claims description 27
• 125000001153 fluoro group Chemical group F* 0.000 claims description 26
• 229910052799 carbon Inorganic materials 0.000 claims description 24
• 239000003795 chemical substances by application Substances 0.000 claims description 24
• 230000033115 angiogenesis Effects 0.000 claims description 23
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 22
• 229910052721 tungsten Inorganic materials 0.000 claims description 22
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 20
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 18
• 125000003282 alkyl amino group Chemical group 0.000 claims description 16
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 16
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 15
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 15
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 14
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 13
• 125000002883 imidazolyl group Chemical group 0.000 claims description 13
• 125000002971 oxazolyl group Chemical group 0.000 claims description 13
• 125000003386 piperidinyl group Chemical group 0.000 claims description 13
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 13
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 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 description 12
• 125000002541 furyl group Chemical group 0.000 claims description 12
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
• 125000004193 piperazinyl group Chemical group 0.000 claims description 12
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
• 125000000335 thiazolyl group Chemical group 0.000 claims description 12
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 11
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
• 125000001424 substituent group Chemical group 0.000 claims description 11
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 10
• 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 description 10
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
• 229940079593 drug Drugs 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 9
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 9
• CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 9
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 9
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
• 206010027476 Metastases Diseases 0.000 claims description 8
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 230000009401 metastasis Effects 0.000 claims description 8
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 8
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 7
• 102000014150 Interferons Human genes 0.000 claims description 7
• 108010050904 Interferons Proteins 0.000 claims description 7
• 125000004104 aryloxy group Chemical group 0.000 claims description 7
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
• 229940079322 interferon Drugs 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 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 description 6
• 239000003242 anti bacterial agent Substances 0.000 claims description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 6
• 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 description 5
• 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 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
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