KR20180070703A - 이미다조[4,5-c]퀴놀린-2-온 화합물 및 암 치료에서의 이의 용도 - Google Patents

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Publication number

KR20180070703A

KR20180070703A KR1020187015448A KR20187015448A KR20180070703A KR 20180070703 A KR20180070703 A KR 20180070703A KR 1020187015448 A KR1020187015448 A KR 1020187015448A KR 20187015448 A KR20187015448 A KR 20187015448A KR 20180070703 A KR20180070703 A KR 20180070703A

Authority

KR

South Korea

Prior art keywords

methyl

imidazo

quinolin

phenyl

nmr

Prior art date

2015-11-03

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Withdrawn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

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• Global Dossier
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• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 82
• 238000011282 treatment Methods 0.000 title claims abstract description 79
• 201000011510 cancer Diseases 0.000 title claims abstract description 75
• NSHFLKZNBPJNPA-UHFFFAOYSA-N imidazo[4,5-c]quinolin-2-one Chemical class C1=CC=C2C3=NC(=O)N=C3C=NC2=C1 NSHFLKZNBPJNPA-UHFFFAOYSA-N 0.000 title claims description 19
• 150000001875 compounds Chemical class 0.000 claims abstract description 229
• 150000003839 salts Chemical class 0.000 claims abstract description 192
• -1 imidazo [4,5-c] quinolin-2-one compound Chemical class 0.000 claims abstract description 170
• 238000004519 manufacturing process Methods 0.000 claims abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• 239000000203 mixture Substances 0.000 claims description 106
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
• LISFMEBWQUVKPJ-UHFFFAOYSA-N carbostyril Natural products C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 63
• 238000000034 method Methods 0.000 claims description 43
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 38
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 37
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 241001465754 Metazoa Species 0.000 claims description 29
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 27
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 23
• 239000002246 antineoplastic agent Substances 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 17
• 125000002393 azetidinyl group Chemical group 0.000 claims description 16
• 125000003386 piperidinyl group Chemical group 0.000 claims description 16
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
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• JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 6
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
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• BKWJAKQVGHWELA-UHFFFAOYSA-N 1-[6-(2-hydroxypropan-2-yl)-2-pyridinyl]-6-[4-(4-methyl-1-piperazinyl)anilino]-2-prop-2-enyl-3-pyrazolo[3,4-d]pyrimidinone Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=C)N(C=3N=C(C=CC=3)C(C)(C)O)C2=N1 BKWJAKQVGHWELA-UHFFFAOYSA-N 0.000 claims description 5
• GLIDQHAUAKRTCP-FQEVSTJZSA-N 8-[4-[2-(dimethylamino)ethoxy]phenyl]-3-methyl-1-[(3S)-oxan-3-yl]imidazo[4,5-c]quinolin-2-one Chemical compound CN(CCOC1=CC=C(C=C1)C1=CC=2C3=C(C=NC=2C=C1)N(C(N3[C@@H]1COCCC1)=O)C)C GLIDQHAUAKRTCP-FQEVSTJZSA-N 0.000 claims description 5
• DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 claims description 5
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• VPQISSQURVSVEH-UHFFFAOYSA-N 1-cyclobutyl-8-[4-[2-(dimethylamino)ethoxy]phenyl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1(CCC1)N1C(N(C=2C=NC=3C=CC(=CC=3C=21)C1=CC=C(C=C1)OCCN(C)C)C)=O VPQISSQURVSVEH-UHFFFAOYSA-N 0.000 claims description 3
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• NMIHWXNHIAKYMO-UHFFFAOYSA-N 3-methyl-1-propan-2-yl-8-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]imidazo[4,5-c]quinolin-2-one Chemical compound C(C)(C)N1C(N(C=2C=NC=3C=CC(=CC=3C=21)C1=CC=C(C=C1)OCCCN1CCCC1)C)=O NMIHWXNHIAKYMO-UHFFFAOYSA-N 0.000 claims description 3
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