CZ20012910A3 - Heteroarylem-substituované chinolin-2-onové deriváty pouľitelné jako protinádorové prostředky - Google Patents

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Publication number

CZ20012910A3

CZ20012910A3 CZ20012910A CZ20012910A CZ20012910A3 CZ 20012910 A3 CZ20012910 A3 CZ 20012910A3 CZ 20012910 A CZ20012910 A CZ 20012910A CZ 20012910 A CZ20012910 A CZ 20012910A CZ 20012910 A3 CZ20012910 A3 CZ 20012910A3

Authority

CZ

Czechia

Prior art keywords

group

aryl

methyl

alkyl

substituents

Prior art date

1999-02-11

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• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title claims description 18
• 238000002360 preparation method Methods 0.000 title description 10
• 230000000259 anti-tumor effect Effects 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 364
• 238000000034 method Methods 0.000 claims abstract description 126
• 150000003839 salts Chemical class 0.000 claims abstract description 53
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• 230000010261 cell growth Effects 0.000 claims abstract description 36
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 36
• 239000012453 solvate Substances 0.000 claims abstract description 34
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 270
• 125000001424 substituent group Chemical group 0.000 claims description 193
• 125000003118 aryl group Chemical group 0.000 claims description 190
• -1 hydroxy, amino Chemical group 0.000 claims description 132
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 125
• 125000000217 alkyl group Chemical group 0.000 claims description 121
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 100
• 229910052739 hydrogen Inorganic materials 0.000 claims description 96
• 229910052736 halogen Inorganic materials 0.000 claims description 87
• 150000002367 halogens Chemical class 0.000 claims description 87
• 229910052799 carbon Inorganic materials 0.000 claims description 81
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 74
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 73
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 73
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 73
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 54
• 125000004122 cyclic group Chemical group 0.000 claims description 51
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 48
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 47
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 43
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
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• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 19
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
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• 239000000126 substance Substances 0.000 claims description 14
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• 125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
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• VXTDNGFVFBFDAK-UHFFFAOYSA-N 6-[amino-(6-chloropyridin-3-yl)-(3-methylimidazol-4-yl)methyl]-4-(3-chlorophenyl)-1-(cyclopropylmethyl)quinolin-2-one Chemical compound CN1C=NC=C1C(N)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)N(CC3CC3)C2=CC=1)C1=CC=C(Cl)N=C1 VXTDNGFVFBFDAK-UHFFFAOYSA-N 0.000 claims description 12
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• CNVJCMJNCGMEIG-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-[(6-chloropyridin-3-yl)-hydroxy-(3-methylimidazol-4-yl)methyl]-1-(cyclopropylmethyl)quinolin-2-one Chemical compound CN1C=NC=C1C(O)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)N(CC3CC3)C2=CC=1)C1=CC=C(Cl)N=C1 CNVJCMJNCGMEIG-UHFFFAOYSA-N 0.000 claims description 6
• 102100026802 72 kDa type IV collagenase Human genes 0.000 claims description 6
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• XLBFHVSNCHNIPX-UHFFFAOYSA-N 6-[amino-(6-chloropyridin-3-yl)-(3-methylimidazol-4-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2-one Chemical compound CN1C=NC=C1C(N)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)N(C)C2=CC=1)C1=CC=C(Cl)N=C1 XLBFHVSNCHNIPX-UHFFFAOYSA-N 0.000 claims description 5
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• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
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• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
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• NODWGCWNHFSPFP-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-[(5-chloropyridin-2-yl)-hydroxy-(3-methylimidazol-4-yl)methyl]-1-methylquinolin-2-one Chemical compound CN1C=NC=C1C(O)(C=1N=CC(Cl)=CC=1)C1=CC=C(N(C)C(=O)C=C2C=3C=C(Cl)C=CC=3)C2=C1 NODWGCWNHFSPFP-UHFFFAOYSA-N 0.000 claims description 4
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• VEUMJJHOMVERCX-UHFFFAOYSA-N 6-[amino-(3-methylimidazol-4-yl)-(6-methylpyridin-3-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2-one Chemical compound C1=NC(C)=CC=C1C(N)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)N(C)C2=CC=1)C1=CN=CN1C VEUMJJHOMVERCX-UHFFFAOYSA-N 0.000 claims description 4
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