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

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 Download PDF

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Publication number: JP2008521900A
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

JP2007544417A

Other languages

English (en)

Japanese (ja)

Other versions

JP2008521900A5 (2

Inventor

キム，テ−ソン

ベロン，ステイーブン

ブツカー，シヨン

ダンジエロ，ノエル

ドミンゲス，セリア

フエローズ，イングリツド

リー，マシユー

リウ，ロンピン

レインボー，エリザベス

ジークムント，アーロン・シー

タスカー，アンドリユー

シー，ニン

チヨン，ユアン

Original Assignee

アムジエン・インコーポレーテツド

Priority date (The priority date 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 date listed.)

2004-11-30

Filing date

2005-11-29

Publication date

2008-06-26

2005-11-29 Application filed by アムジエン・インコーポレーテツド filed Critical アムジエン・インコーポレーテツド

2008-06-26 Publication of JP2008521900A publication Critical patent/JP2008521900A/ja

2009-01-22 Publication of JP2008521900A5 publication Critical patent/JP2008521900A5/ja

Status Withdrawn legal-status Critical Current

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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
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 description 4
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 description 4
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229940100197 antimetabolite Drugs 0.000 claims description 4
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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 description 4
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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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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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 description 2
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 description 2
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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 description 2
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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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 description 2
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 description 2
125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 claims description 2
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 2
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 description 2
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 description 2
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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 description 2
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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 description 2
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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 description 2
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 description 2
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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 description 2
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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 description 2
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 description 2
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 description 2
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 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

JP2007544417A 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 Withdrawn JP2008521900A (ja)

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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

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US (1)	US7652009B2 (2)
EP (1)	EP1827434B1 (2)
JP (1)	JP2008521900A (2)
AU (1)	AU2005312048B2 (2)
CA (1)	CA2587642C (2)
ES (1)	ES2450566T3 (2)
MX (1)	MX2007006230A (2)
WO (1)	WO2006060318A2 (2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2020502167A (ja) *	2016-12-15	2020-01-23	コリアリサーチインスティチュートオブバイオサイエンスアンドバイオテクノロジー	ピリジン系化合物を有効成分として含有するｄｙｒｋ関連疾患の予防又は治療用薬学的組成物

Families Citing this family (63)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE409082T1 (de) *	2004-11-16	2008-10-15	T & S Brass & Bronze Works Inc	Sprühventilanordnung für vorspülungseinheiten.
JP5113752B2 (ja)	2005-08-22	2013-01-09	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キナーゼの活性を調節し、関連する疾患を治療するための方法および製剤
HRP20130719T1 (en) *	2005-08-24	2013-09-30	Eisai R&D Management Co., Ltd.	Novel pyridine derivative and pyrimidine derivative (3)
JP2009526761A (ja) *	2006-01-30	2009-07-23	アレイバイオファーマ、インコーポレイテッド	ヘテロ二環式チオフェン化合物および使用の方法
UY30183A1 (es) *	2006-03-02	2007-10-31	Astrazeneca Ab	Derivados de quinolina
US20090076075A1 (en) *	2006-03-02	2009-03-19	Frederic Henri Jung	Quinoline derivatives
BRPI0708615A2 (pt) *	2006-03-07	2011-06-07	Array Biopharma Inc	compostos de pirazol heterobicìclicos e métodos de uso
JP2009539878A (ja) *	2006-06-08	2009-11-19	アレイバイオファーマ、インコーポレイテッド	キノリン化合物および使用方法
CA2661333C (en) *	2006-08-23	2014-08-05	Eisai R&D Management Co., Ltd.	Salt of phenoxypyridine derivative or crystal thereof and process for producing the same
US7790885B2 (en) *	2006-08-31	2010-09-07	Eisai R&D Management Co., Ltd.	Process for preparing phenoxypyridine derivatives
EP2125781A2 (en)	2006-12-20	2009-12-02	Amgen Inc.	Substituted heterocycles and methods of use
CA2678813A1 (en) *	2007-02-20	2008-08-28	Melior Pharmaceuticals I, Inc.	Methods of identifying activators of lyn kinase
WO2008118454A2 (en) *	2007-03-23	2008-10-02	Amgen Inc.	Derivatives of quinoline or benzopyrazine and their uses for the treatment of (inter alia) inflammatory diseases, autoimmune diseases or various kinds of cancer
AU2008240044B2 (en) *	2007-04-13	2013-09-12	Teva Pharamceuticals International Gmbh	Oral cephalotaxine dosage forms
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
JP2009203226A (ja) *	2008-01-31	2009-09-10	Eisai R & D Management Co Ltd	ピリジン誘導体およびピリミジン誘導体を含有するレセプターチロシンキナーゼ阻害剤
US20100311972A1 (en) *	2008-02-18	2010-12-09	Mitsuo Nagai	Method for producing phenoxypyridine derivative
BRPI0908573A2 (pt) *	2008-03-05	2012-12-25	Methylgene Inc	inibidores da atividade de proteÍna tirosina quinase
US8552184B2 (en) *	2008-07-03	2013-10-08	Melior Pharmaceuticals I, Inc.	Compounds and methods for treating disorders related to glucose metabolism
EP2340244A4 (en) *	2008-10-14	2012-07-25	Ning Xi	COMPOUNDS AND APPLICATION PROCEDURES
ES2578990T3 (es) *	2009-03-21	2016-08-03	Sunshine Lake Pharma Co., Ltd.	Derivados de amino éster, sales de los mismos y métodos de uso
WO2011114103A1 (en) *	2010-03-18	2011-09-22	Biolipox Ab	Pyrimidinones for use as medicaments
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
US9133123B2 (en)	2010-04-23	2015-09-15	Cytokinetics, Inc.	Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use
AR081331A1 (es)	2010-04-23	2012-08-08	Cytokinetics Inc	Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos
US20130158055A1 (en)	2010-05-28	2013-06-20	Andrew G. Reaume	Prevention Of Pancreatic Beta Cell Degeneration
WO2011162343A1 (ja)	2010-06-25	2011-12-29	エーザイ・アール・アンド・ディー・マネジメント株式会社	キナーゼ阻害作用を有する化合物の併用による抗腫瘍剤
KR20140069235A (ko)	2011-09-27	2014-06-09	노파르티스 아게	돌연변이체 idh의 억제제로서의 3-피리미딘-4-일-옥사졸리딘-2-온
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
JP6669499B2 (ja)	2013-02-15	2020-03-18	カラファーマシューティカルズインコーポレイテッド	治療用化合物
JP2016510000A (ja)	2013-02-20	2016-04-04	カラファーマシューティカルズインコーポレイテッド	治療用化合物およびその使用
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
EP2970240B1 (en)	2013-03-14	2018-01-10	Novartis AG	3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant idh
EP2997377B1 (en)	2013-05-14	2018-07-18	Eisai R&D Management Co., Ltd.	Biomarkers for predicting and assessing responsiveness of endometrial cancer subjects to lenvatinib compounds
US9890173B2 (en)	2013-11-01	2018-02-13	Kala Pharmaceuticals, Inc.	Crystalline forms of therapeutic compounds and uses thereof
NZ719185A (en)	2013-11-01	2017-11-24	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
PT3524595T (pt)	2014-08-28	2022-09-19	Eisai R&D Man Co Ltd	Derivado de quinolina altamente puro e método para produção do mesmo
AU2016224583B2 (en)	2015-02-25	2021-06-03	Eisai R&D Management Co., Ltd.	Method for suppressing bitterness of quinoline derivative
KR102662228B1 (ko)	2015-03-04	2024-05-02	머크 샤프 앤드 돔 코포레이션	암을 치료하기 위한 pd-1 길항제 및 vegfr/fgfr/ret 티로신 키나제 억제제의 조합
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
KR20190051010A (ko)	2016-09-08	2019-05-14	칼라 파마슈티컬스, 인크.	치료 화합물의 결정형 및 그의 용도
AU2017324713B2 (en)	2016-09-08	2020-08-13	KALA BIO, Inc.	Crystalline forms of therapeutic compounds and uses thereof
EP3509423A4 (en)	2016-09-08	2020-05-13	Kala Pharmaceuticals, Inc.	CRYSTALLINE FORMS OF THERAPEUTIC COMPOUNDS AND USES THEREOF
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
JP6581320B2 (ja)	2017-02-08	2019-09-25	エーザイ・アール・アンド・ディー・マネジメント株式会社	腫瘍治療用医薬組成物
SG11201909406VA (en)	2017-04-10	2019-11-28	Melior Pharmaceuticals I Inc	Treatment of adipocytes
EP3624800A4 (en)	2017-05-16	2021-02-17	Eisai R&D Management Co., Ltd.	TREATMENT OF HEPATOCELLULAR CARCINOMA
RU2020133727A (ru) *	2018-03-21	2022-04-21	Сучжоу Пухе Биофарма Ко., Лтд.	Ингибиторы shp2 и их применение
JP7447089B2 (ja)	2018-08-31	2024-03-11	サイトキネティックス，インコーポレイテッド	心筋サルコメア阻害剤
WO2020113094A1 (en)	2018-11-30	2020-06-04	Nuvation Bio Inc.	Pyrrole and pyrazole compounds and methods of use thereof
US11292782B2 (en)	2018-11-30	2022-04-05	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
MX2023010125A (es)	2021-03-04	2023-09-11	Cytokinetics Inc	Inhibidores del sarcomero cardiaco.
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)

* Cited by examiner, † Cited by third party
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
AU4547396A (en)	1995-01-31	1996-08-21	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
US6143764A (en) *	1995-11-07	2000-11-07	Kirin Beer Kabushiki Kaisha	Quinoline and quinazoline derivatives inhibiting platelet-derived growth factor receptor autophosphorylation and pharmaceutical compositions containing the same
ATE201873T1 (de) *	1995-11-14	2001-06-15	Pharmacia & Upjohn Spa	Aryl- und heteroaryl- purin- und pyridopyrimidin- derivate
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
PL335235A1 (en)	1997-02-19	2000-04-10	Berlex Lab	N-heterocyclic derivatives as nos inhibitors
WO2000012089A1 (en)	1998-08-31	2000-03-09	Merck & Co., Inc.	Novel angiogenesis inhibitors
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
ATE430149T1 (de)	1998-03-04	2009-05-15	Bristol Myers Squibb Co	Heterocyclen substituierte imidazopyrazine als protein- tyrosin-kinase-inhibitoren
WO1999054309A1 (en)	1998-04-23	1999-10-28	Takeda Chemical Industries, Ltd.	Naphthalene derivatives, their production and use
WO1999061428A1 (en)	1998-05-28	1999-12-02	Parker Hughes Institute	Quinazolines for treating brain tumor
EA005032B1 (ru)	1998-05-29	2004-10-28	Сьюджен, Инк.	Пирролзамещенные 2-индолиноны (варианты), фармацевтическая композиция (варианты), способ модулирования каталитической активности протеинкиназы, способ лечения или профилактики нарушения в организме, связанного с протеинкиназой
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
AU747427B2 (en)	1998-07-10	2002-05-16	Merck & Co., Inc.	Novel angiogenesis inhibitors
US6313129B1 (en) *	1998-08-21	2001-11-06	Hughes Institute	Therapeutic compounds
ATE538794T1 (de)	1999-01-13	2012-01-15	Bayer Healthcare Llc	Gamma carboxyarylsubstituierte diphenylharnstoffverbindungen als p38 kinasehemmer
IL144461A0 (en) *	1999-01-22	2002-05-23	Kirin Brewery	Quinoline and quinazoline derivatives and pharmaceutical compositions containing them
SK288365B6 (sk)	1999-02-10	2016-07-01	Astrazeneca Ab	Medziprodukty pre chinazolínové deriváty ako inhibítory angiogenézy
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
WO2000059509A1 (en)	1999-03-30	2000-10-12	Novartis Ag	Phthalazine derivatives for treating inflammatory diseases
ES2231179T3 (es)	1999-04-12	2005-05-16	Aventis Pharma Limited	Compuestos de heteroarilo biciclicos sustituidos como antagonistas de la integrina.
KR20020032608A (ko) *	1999-09-21	2002-05-03	다비드 에 질레스	퀴나졸린 화합물 및 이를 함유하는 제약 조성물
CZ301689B6 (cs)	1999-11-05	2010-05-26	Astrazeneca Ab	Derivát chinazolinu a farmaceutický prostredek, který ho obsahuje
PT1233943E (pt)	1999-11-24	2011-09-01	Sugen Inc	Formulações para agentes farmacêuticos ionizáveis como ácidos livres ou bases livres
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
JP2003528072A (ja)	2000-03-17	2003-09-24	ブリストル−マイヤーズスクイブファーマカンパニー	マトリックスメタロプロテアーゼおよびＴＮＦ−αの阻害剤としての環状β−アミノ酸誘導体
JP2003528097A (ja)	2000-03-17	2003-09-24	ブリストル−マイヤーズスクイブファーマカンパニー	マトリックスメタロプロテアーゼおよびＴＮＦ−α阻害剤としてのβ−アミノ酸誘導体
US6630500B2 (en)	2000-08-25	2003-10-07	Cephalon, Inc.	Selected fused pyrrolocarbazoles
EP1317450B1 (en)	2000-09-15	2006-11-22	Vertex Pharmaceuticals Incorporated	Pyrazole compounds useful as protein kinase inhibitors
US6849625B2 (en)	2000-10-13	2005-02-01	Astrazeneca Ab	Quinazoline derivatives with anti-tumour activity
DE60137273D1 (de) *	2000-10-20	2009-02-12	Eisai R&D Man Co Ltd	Verfahren zur Herstellung von 4-Phenoxy chinolin Derivaten
EP1343782B1 (en)	2000-12-21	2009-05-06	SmithKline Beecham Corporation	Pyrimidineamines as angiogenesis modulators
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
US6878714B2 (en)	2001-01-12	2005-04-12	Amgen Inc.	Substituted alkylamine derivatives and methods of use
US20020147198A1 (en)	2001-01-12	2002-10-10	Guoqing Chen	Substituted arylamine derivatives and methods of use
US6995162B2 (en)	2001-01-12	2006-02-07	Amgen Inc.	Substituted alkylamine derivatives and methods of use
DE60239097D1 (de) *	2001-03-02	2011-03-17	Gpc Biotech Ag	Drei-hybrid-assaysystem
US20030125344A1 (en)	2001-03-23	2003-07-03	Bayer Corporation	Rho-kinase inhibitors
JP4583751B2 (ja)	2001-06-06	2010-11-17	アベンティス・フアーマ・リミテッド	炎症性疾患の治療に使用するための置換されたテトラヒドロイソキノリン
EP2258366B1 (en)	2001-06-22	2013-04-03	Kirin Pharma Kabushiki Kaisha	Quinoline 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
JP4608215B2 (ja)	2002-02-01	2011-01-12	アストラゼネカアクチボラグ	キナゾリン化合物
US7645878B2 (en)	2002-03-22	2010-01-12	Bayer Healthcare Llc	Process for preparing quinazoline Rho-kinase inhibitors and intermediates thereof
NZ535985A (en)	2002-03-29	2007-04-27	Chiron Corp	Substituted benzazoles and use thereof as RAF kinase inhibitors
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
EP1548008A4 (en)	2002-08-23	2008-08-06	Kirin Pharma Kk	COMPOUND WITH TGF-BETA-HEMMENDER EFFECT AND THIS MEDICAL COMPOSITION CONTAINING
AU2003255482A1 (en)	2002-10-02	2004-04-23	Merck Patent Gmbh	Use of 4 amino-quinazolines as anti cancer agents
US7495016B2 (en) *	2002-10-21	2009-02-24	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
EP1603884A4 (en)	2003-02-28	2008-05-28	Encysive Pharmaceuticals Inc	PYRIDINE, PYRIMIDINE, QUINOLINE, QUINAZOLINE AND NAPHTHALENE UROTENSIN II RECEPTOR ANTAGONISTS
CA2517291C (en)	2003-03-19	2012-05-08	Exelixis, Inc.	Ortho-substituted aryl and heteroaryl 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
EP1660503A1 (en)	2003-08-29	2006-05-31	Pfizer Inc.	Naphthalene carboxamides and their derivatives useful as new anti-angiogenic agents
PT2213661E (pt) *	2003-09-26	2011-12-15	Exelixis Inc	Moduladores de c-met e métodos de uso
CN1882345A (zh)	2003-10-16	2006-12-20	希龙公司	作为raf激酶抑制剂以治疗癌症的2,6－二取代的喹唑啉、喹喔啉、喹啉和异喹啉
WO2005073224A2 (en) *	2004-01-23	2005-08-11	Amgen Inc	Quinoline quinazoline pyridine and pyrimidine counds and their use in the treatment of inflammation angiogenesis and cancer
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
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 MX MX2007006230A patent/MX2007006230A/es not_active Application Discontinuation
- 2005-11-29 AU AU2005312048A patent/AU2005312048B2/en not_active Ceased
- 2005-11-29 EP EP05848812.3A patent/EP1827434B1/en not_active Expired - Lifetime
- 2005-11-29 US US11/289,659 patent/US7652009B2/en active Active
- 2005-11-29 WO PCT/US2005/042935 patent/WO2006060318A2/en not_active Ceased
- 2005-11-29 JP JP2007544417A patent/JP2008521900A/ja not_active Withdrawn
- 2005-11-29 CA CA2587642A patent/CA2587642C/en not_active Expired - Fee Related
- 2005-11-29 ES ES05848812.3T patent/ES2450566T3/es not_active Expired - Lifetime

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2020502167A (ja) *	2016-12-15	2020-01-23	コリアリサーチインスティチュートオブバイオサイエンスアンドバイオテクノロジー	ピリジン系化合物を有効成分として含有するｄｙｒｋ関連疾患の予防又は治療用薬学的組成物
US10765669B2 (en)	2016-12-15	2020-09-08	Korea Research Institute Of Bioscience And Biotechnology	Pharmaceutical composition for preventing or treating DYRK-related diseases, containing pyridine-based compound as active ingredient

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WO2006060318A3 (en)	2006-07-20
ES2450566T3 (es)	2014-03-25
US7652009B2 (en)	2010-01-26
MX2007006230A (es)	2007-07-25
CA2587642C (en)	2013-04-09
WO2006060318A2 (en)	2006-06-08
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