JP2005534636A5 - - Google Patents
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- Publication number
- JP2005534636A5 JP2005534636A5 JP2004505373A JP2004505373A JP2005534636A5 JP 2005534636 A5 JP2005534636 A5 JP 2005534636A5 JP 2004505373 A JP2004505373 A JP 2004505373A JP 2004505373 A JP2004505373 A JP 2004505373A JP 2005534636 A5 JP2005534636 A5 JP 2005534636A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- phenyl
- imidazo
- quinolin
- dihydro
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 206010028980 Neoplasm Diseases 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- -1 hydroxy, amino Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 7
- 210000002307 prostate Anatomy 0.000 claims description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 201000008275 breast carcinoma Diseases 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 208000032839 leukemia Diseases 0.000 claims description 4
- 210000004072 lung Anatomy 0.000 claims description 4
- 230000009826 neoplastic cell growth Effects 0.000 claims description 4
- 206010052360 Colorectal adenocarcinoma Diseases 0.000 claims description 3
- 208000034578 Multiple myelomas Diseases 0.000 claims description 3
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 206010039491 Sarcoma Diseases 0.000 claims description 3
- 210000004100 adrenal gland Anatomy 0.000 claims description 3
- 210000004556 brain Anatomy 0.000 claims description 3
- 210000000481 breast Anatomy 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 208000005017 glioblastoma Diseases 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 210000003734 kidney Anatomy 0.000 claims description 3
- 210000004185 liver Anatomy 0.000 claims description 3
- 210000001672 ovary Anatomy 0.000 claims description 3
- 210000000496 pancreas Anatomy 0.000 claims description 3
- 230000002062 proliferating effect Effects 0.000 claims description 3
- 201000001514 prostate carcinoma Diseases 0.000 claims description 3
- 210000000664 rectum Anatomy 0.000 claims description 3
- 210000002784 stomach Anatomy 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 210000003932 urinary bladder Anatomy 0.000 claims description 3
- 210000001215 vagina Anatomy 0.000 claims description 3
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 2
- 206010020718 hyperplasia Diseases 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 150000003839 salts Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000001905 inorganic group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- OJWYDRGMQWQCBO-UHFFFAOYSA-N 1-(2-fluorophenyl)-3h-imidazo[4,5-c]quinolin-2-one Chemical compound FC1=CC=CC=C1N1C(=O)NC2=C1C1=CC=CC=C1N=C2 OJWYDRGMQWQCBO-UHFFFAOYSA-N 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- BGPKBMKIUFZTME-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3-(3-nitrophenyl)imidazo[4,5-c]quinolin-2-one Chemical compound [O-][N+](=O)C1=CC=CC(N2C(N(C=3C(=CC=CC=3)Cl)C3=C4C=C(Cl)C=CC4=NC=C32)=O)=C1 BGPKBMKIUFZTME-UHFFFAOYSA-N 0.000 claims 2
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims 2
- 241000023320 Luma <angiosperm> Species 0.000 claims 2
- 206010042135 Stomatitis necrotising Diseases 0.000 claims 2
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 2
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 2
- 201000008585 noma Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 2
- ZNBSRKVMSNKUOS-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-(3-chlorophenyl)-8-methylimidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(C=2C(=CC=CC=2)Cl)C=2C3=CC(C)=CC=C3N=CC=2N1C1=CC=CC(Cl)=C1 ZNBSRKVMSNKUOS-UHFFFAOYSA-N 0.000 claims 1
- MWAYMFYZOJXJMU-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-(3-methoxyphenyl)-8-methylimidazo[4,5-c]quinolin-2-one Chemical compound COC1=CC=CC(N2C(N(C=3C(=CC=CC=3)Cl)C3=C4C=C(C)C=CC4=NC=C32)=O)=C1 MWAYMFYZOJXJMU-UHFFFAOYSA-N 0.000 claims 1
- YZRRSEDFOUEEHB-UHFFFAOYSA-N 1-(2-chlorophenyl)-8-methyl-3-[3-(trifluoromethyl)phenyl]imidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(C=2C(=CC=CC=2)Cl)C=2C3=CC(C)=CC=C3N=CC=2N1C1=CC=CC(C(F)(F)F)=C1 YZRRSEDFOUEEHB-UHFFFAOYSA-N 0.000 claims 1
- KXTRZVLPEHDUCK-UHFFFAOYSA-N 1-(2-chlorophenyl)-8-methyl-3-phenylimidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(C=2C(=CC=CC=2)Cl)C=2C3=CC(C)=CC=C3N=CC=2N1C1=CC=CC=C1 KXTRZVLPEHDUCK-UHFFFAOYSA-N 0.000 claims 1
- UFKSFNKNOCMZHF-UHFFFAOYSA-N 1-(2-chlorophenyl)-8-methyl-3h-imidazo[4,5-c]quinolin-2-one Chemical compound C1=2C3=CC(C)=CC=C3N=CC=2NC(=O)N1C1=CC=CC=C1Cl UFKSFNKNOCMZHF-UHFFFAOYSA-N 0.000 claims 1
- KUGCFLKQWVVXAM-UHFFFAOYSA-N 1-(2-fluorophenyl)-8-methyl-3h-imidazo[4,5-c]quinolin-2-one Chemical compound C1=2C3=CC(C)=CC=C3N=CC=2NC(=O)N1C1=CC=CC=C1F KUGCFLKQWVVXAM-UHFFFAOYSA-N 0.000 claims 1
- PKKCVYOXEOJQJV-UHFFFAOYSA-N 1-cyclohexyl-6-hexoxy-8-methyl-3h-imidazo[4,5-c]quinolin-2-one Chemical compound O=C1NC2=CN=C3C(OCCCCCC)=CC(C)=CC3=C2N1C1CCCCC1 PKKCVYOXEOJQJV-UHFFFAOYSA-N 0.000 claims 1
- MVBDRSJRMTWGDN-UHFFFAOYSA-N 3-(2-aminophenyl)-8-bromo-1-(2-chlorophenyl)imidazo[4,5-c]quinolin-2-one Chemical compound NC1=CC=CC=C1N1C(=O)N(C=2C(=CC=CC=2)Cl)C2=C3C=C(Br)C=CC3=NC=C21 MVBDRSJRMTWGDN-UHFFFAOYSA-N 0.000 claims 1
- CCMQAMMXZMDLIA-UHFFFAOYSA-N 3-(3-aminophenyl)-1-(2-chlorophenyl)-8-methylimidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(C=2C(=CC=CC=2)Cl)C=2C3=CC(C)=CC=C3N=CC=2N1C1=CC=CC(N)=C1 CCMQAMMXZMDLIA-UHFFFAOYSA-N 0.000 claims 1
- YQXJXFWXKVRRIW-UHFFFAOYSA-N 3-(3-aminophenyl)-8-chloro-1-(2-chlorophenyl)imidazo[4,5-c]quinolin-2-one Chemical compound NC1=CC=CC(N2C(N(C=3C(=CC=CC=3)Cl)C3=C4C=C(Cl)C=CC4=NC=C32)=O)=C1 YQXJXFWXKVRRIW-UHFFFAOYSA-N 0.000 claims 1
- FCQGDVVXCCLVCM-UHFFFAOYSA-N 3-butyl-8-chloro-1-(2-chlorophenyl)imidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(CCCC)C2=CN=C3C=CC(Cl)=CC3=C2N1C1=CC=CC=C1Cl FCQGDVVXCCLVCM-UHFFFAOYSA-N 0.000 claims 1
- NAZJWZFPCSAOHR-UHFFFAOYSA-N 8-bromo-1-(2-chlorophenyl)-3-(3-chlorophenyl)imidazo[4,5-c]quinolin-2-one Chemical compound ClC1=CC=CC(N2C(N(C=3C(=CC=CC=3)Cl)C3=C4C=C(Br)C=CC4=NC=C32)=O)=C1 NAZJWZFPCSAOHR-UHFFFAOYSA-N 0.000 claims 1
- XXVXFJLNTOEEKR-UHFFFAOYSA-N 8-bromo-1-(2-chlorophenyl)-3-(3-methoxyphenyl)imidazo[4,5-c]quinolin-2-one Chemical compound COC1=CC=CC(N2C(N(C=3C(=CC=CC=3)Cl)C3=C4C=C(Br)C=CC4=NC=C32)=O)=C1 XXVXFJLNTOEEKR-UHFFFAOYSA-N 0.000 claims 1
- ZROZVGYZVPABDO-UHFFFAOYSA-N 8-bromo-1-(2-chlorophenyl)-3-(3-nitrophenyl)imidazo[4,5-c]quinolin-2-one Chemical compound [O-][N+](=O)C1=CC=CC(N2C(N(C=3C(=CC=CC=3)Cl)C3=C4C=C(Br)C=CC4=NC=C32)=O)=C1 ZROZVGYZVPABDO-UHFFFAOYSA-N 0.000 claims 1
- ICJRYLZOAZRYHV-UHFFFAOYSA-N 8-bromo-1-(2-chlorophenyl)-3-[3-(trifluoromethyl)phenyl]imidazo[4,5-c]quinolin-2-one Chemical compound FC(F)(F)C1=CC=CC(N2C(N(C=3C(=CC=CC=3)Cl)C3=C4C=C(Br)C=CC4=NC=C32)=O)=C1 ICJRYLZOAZRYHV-UHFFFAOYSA-N 0.000 claims 1
- PGKNBGGQQHNSRR-UHFFFAOYSA-N 8-bromo-1-(2-chlorophenyl)-3-ethylimidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(CC)C2=CN=C3C=CC(Br)=CC3=C2N1C1=CC=CC=C1Cl PGKNBGGQQHNSRR-UHFFFAOYSA-N 0.000 claims 1
- QASHQZJYQGDZOF-UHFFFAOYSA-N 8-bromo-1-(2-chlorophenyl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(C)C2=CN=C3C=CC(Br)=CC3=C2N1C1=CC=CC=C1Cl QASHQZJYQGDZOF-UHFFFAOYSA-N 0.000 claims 1
- IONOGCVKZSKRGF-UHFFFAOYSA-N 8-bromo-1-(2-chlorophenyl)-3-phenylimidazo[4,5-c]quinolin-2-one Chemical compound ClC1=CC=CC=C1N1C(=O)N(C=2C=CC=CC=2)C2=C1C1=CC(Br)=CC=C1N=C2 IONOGCVKZSKRGF-UHFFFAOYSA-N 0.000 claims 1
- SIQZFWRLJUKKCD-UHFFFAOYSA-N 8-bromo-1-(2-chlorophenyl)-3-propan-2-ylimidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(C(C)C)C2=CN=C3C=CC(Br)=CC3=C2N1C1=CC=CC=C1Cl SIQZFWRLJUKKCD-UHFFFAOYSA-N 0.000 claims 1
- HFYDAZHTIXGXLX-UHFFFAOYSA-N 8-bromo-1-(2-chlorophenyl)-3h-imidazo[4,5-c]quinolin-2-one Chemical compound ClC1=CC=CC=C1N1C(=O)NC2=C1C1=CC(Br)=CC=C1N=C2 HFYDAZHTIXGXLX-UHFFFAOYSA-N 0.000 claims 1
- DPERJEFFYWQKRO-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3-(2,2-dimethylpropyl)imidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(CC(C)(C)C)C2=CN=C3C=CC(Cl)=CC3=C2N1C1=CC=CC=C1Cl DPERJEFFYWQKRO-UHFFFAOYSA-N 0.000 claims 1
- JXSPPLWZSQAOGD-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3-(2,3-dihydroxypropyl)imidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(CC(O)CO)C2=CN=C3C=CC(Cl)=CC3=C2N1C1=CC=CC=C1Cl JXSPPLWZSQAOGD-UHFFFAOYSA-N 0.000 claims 1
- IPCMFDPJMZDJEJ-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3-(2-methylpropyl)imidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(CC(C)C)C2=CN=C3C=CC(Cl)=CC3=C2N1C1=CC=CC=C1Cl IPCMFDPJMZDJEJ-UHFFFAOYSA-N 0.000 claims 1
- LANHQWYOGQDTCD-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3-(3-chlorophenyl)imidazo[4,5-c]quinolin-2-one Chemical compound ClC1=CC=CC(N2C(N(C=3C(=CC=CC=3)Cl)C3=C4C=C(Cl)C=CC4=NC=C32)=O)=C1 LANHQWYOGQDTCD-UHFFFAOYSA-N 0.000 claims 1
- ZWXQULFXEOEXCH-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3-(3-methoxyphenyl)imidazo[4,5-c]quinolin-2-one Chemical compound COC1=CC=CC(N2C(N(C=3C(=CC=CC=3)Cl)C3=C4C=C(Cl)C=CC4=NC=C32)=O)=C1 ZWXQULFXEOEXCH-UHFFFAOYSA-N 0.000 claims 1
- ICCYUHZUVRQZAM-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3-(cyclohexylmethyl)imidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(C=2C(=CC=CC=2)Cl)C=2C3=CC(Cl)=CC=C3N=CC=2N1CC1CCCCC1 ICCYUHZUVRQZAM-UHFFFAOYSA-N 0.000 claims 1
- RCXLUPVATKGDNS-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3-(cyclopropylmethyl)imidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(C=2C(=CC=CC=2)Cl)C=2C3=CC(Cl)=CC=C3N=CC=2N1CC1CC1 RCXLUPVATKGDNS-UHFFFAOYSA-N 0.000 claims 1
- MEASAAQFFXPMHM-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3-(furan-3-ylmethyl)imidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(C=2C(=CC=CC=2)Cl)C=2C3=CC(Cl)=CC=C3N=CC=2N1CC=1C=COC=1 MEASAAQFFXPMHM-UHFFFAOYSA-N 0.000 claims 1
- MSEKIAPUFVTREV-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3-[3-(trifluoromethyl)phenyl]imidazo[4,5-c]quinolin-2-one Chemical compound FC(F)(F)C1=CC=CC(N2C(N(C=3C(=CC=CC=3)Cl)C3=C4C=C(Cl)C=CC4=NC=C32)=O)=C1 MSEKIAPUFVTREV-UHFFFAOYSA-N 0.000 claims 1
- QDQQGZWEVKSMRQ-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3-ethylimidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(CC)C2=CN=C3C=CC(Cl)=CC3=C2N1C1=CC=CC=C1Cl QDQQGZWEVKSMRQ-UHFFFAOYSA-N 0.000 claims 1
- MJAHEPKISOLZNP-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3-heptylimidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(CCCCCCC)C2=CN=C3C=CC(Cl)=CC3=C2N1C1=CC=CC=C1Cl MJAHEPKISOLZNP-UHFFFAOYSA-N 0.000 claims 1
- STBRITKMWPCULD-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3-phenylimidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(C=2C(=CC=CC=2)Cl)C=2C3=CC(Cl)=CC=C3N=CC=2N1C1=CC=CC=C1 STBRITKMWPCULD-UHFFFAOYSA-N 0.000 claims 1
- LOLYSJJSHSFQHO-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-3h-imidazo[4,5-c]quinolin-2-one Chemical compound C1=2C3=CC(Cl)=CC=C3N=CC=2NC(=O)N1C1=CC=CC=C1Cl LOLYSJJSHSFQHO-UHFFFAOYSA-N 0.000 claims 1
- HBRBYVCDBVLLDY-UHFFFAOYSA-N 8-chloro-1-(2-fluorophenyl)-3h-imidazo[4,5-c]quinolin-2-one Chemical compound FC1=CC=CC=C1N1C(=O)NC2=C1C1=CC(Cl)=CC=C1N=C2 HBRBYVCDBVLLDY-UHFFFAOYSA-N 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 claims 1
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- 239000004480 active ingredient Substances 0.000 claims 1
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- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
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- NSHFLKZNBPJNPA-UHFFFAOYSA-N imidazo[4,5-c]quinolin-2-one Chemical compound C1=CC=C2C3=NC(=O)N=C3C=NC2=C1 NSHFLKZNBPJNPA-UHFFFAOYSA-N 0.000 claims 1
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- 238000000034 method Methods 0.000 claims 1
- GINXKRGXHUMJRS-UHFFFAOYSA-N n-[3-[1-(2-chlorophenyl)-8-methyl-2-oxoimidazo[4,5-c]quinolin-3-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2C(N(C=3C(=CC=CC=3)Cl)C3=C4C=C(C)C=CC4=NC=C32)=O)=C1 GINXKRGXHUMJRS-UHFFFAOYSA-N 0.000 claims 1
- LGWLXYWKCWPTBU-UHFFFAOYSA-N n-[3-[8-bromo-1-(2-chlorophenyl)-2-oxoimidazo[4,5-c]quinolin-3-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2C(N(C=3C(=CC=CC=3)Cl)C3=C4C=C(Br)C=CC4=NC=C32)=O)=C1 LGWLXYWKCWPTBU-UHFFFAOYSA-N 0.000 claims 1
- OWXIEPANRNEJEU-UHFFFAOYSA-N n-[3-[8-chloro-1-(2-chlorophenyl)-2-oxoimidazo[4,5-c]quinolin-3-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2C(N(C=3C(=CC=CC=3)Cl)C3=C4C=C(Cl)C=CC4=NC=C32)=O)=C1 OWXIEPANRNEJEU-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 201000011510 cancer Diseases 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
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- 239000002904 solvent Substances 0.000 description 6
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 102100030011 Endoribonuclease Human genes 0.000 description 3
- 101710199605 Endoribonuclease Proteins 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 3
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 3
- 101710113029 Serine/threonine-protein kinase Proteins 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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-
2002
- 2002-05-21 GB GBGB0211649.9A patent/GB0211649D0/en not_active Ceased
-
2003
- 2003-05-20 SI SI200331434T patent/SI1509521T1/sl unknown
- 2003-05-20 AT AT03730079T patent/ATE405564T1/de active
- 2003-05-20 US US10/515,126 patent/US7998972B2/en not_active Expired - Fee Related
- 2003-05-20 PT PT03730079T patent/PT1509521E/pt unknown
- 2003-05-20 CN CNB038117053A patent/CN100475207C/zh not_active Expired - Fee Related
- 2003-05-20 BR BR0311221-7A patent/BR0311221A/pt not_active IP Right Cessation
- 2003-05-20 ES ES03730079T patent/ES2312783T3/es not_active Expired - Lifetime
- 2003-05-20 AU AU2003240680A patent/AU2003240680A1/en not_active Abandoned
- 2003-05-20 JP JP2004505373A patent/JP4707389B2/ja not_active Expired - Fee Related
- 2003-05-20 CA CA002485012A patent/CA2485012A1/en not_active Abandoned
- 2003-05-20 DK DK03730079T patent/DK1509521T3/da active
- 2003-05-20 EP EP03730079A patent/EP1509521B8/en not_active Expired - Lifetime
- 2003-05-20 WO PCT/EP2003/005291 patent/WO2003097641A2/en not_active Ceased
- 2003-05-20 DE DE60323090T patent/DE60323090D1/de not_active Expired - Lifetime
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