KR20160049003A - 항증식성 화합물 - Google Patents

Info

Publication number

KR20160049003A

KR20160049003A KR1020167008823A KR20167008823A KR20160049003A KR 20160049003 A KR20160049003 A KR 20160049003A KR 1020167008823 A KR1020167008823 A KR 1020167008823A KR 20167008823 A KR20167008823 A KR 20167008823A KR 20160049003 A KR20160049003 A KR 20160049003A

Authority

KR

South Korea

Prior art keywords

alkyl

carbocyclyl

alkynyl

alkenyl

heterocyclyl

Prior art date

2013-09-05

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Withdrawn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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• 150000001875 compounds Chemical class 0.000 title claims abstract description 291
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• 238000011282 treatment Methods 0.000 claims abstract description 42
• -1 1- C 6 alkanoyl Chemical group 0.000 claims description 206
• 125000000217 alkyl group Chemical group 0.000 claims description 163
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 140
• 125000000623 heterocyclic group Chemical group 0.000 claims description 129
• 125000005843 halogen group Chemical group 0.000 claims description 86
• 229940127089 cytotoxic agent Drugs 0.000 claims description 78
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 67
• 206010028980 Neoplasm Diseases 0.000 claims description 64
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 63
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 60
• 229910052739 hydrogen Inorganic materials 0.000 claims description 58
• 125000000304 alkynyl group Chemical group 0.000 claims description 52
• 229910052799 carbon Inorganic materials 0.000 claims description 52
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 52
• 125000003342 alkenyl group Chemical group 0.000 claims description 51
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• 239000002254 cytotoxic agent Substances 0.000 claims description 50
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• 229910052757 nitrogen Inorganic materials 0.000 claims description 42
• 239000003814 drug Substances 0.000 claims description 41
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 38
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 30
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• 208000035475 disorder Diseases 0.000 claims description 29
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• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
• 125000004043 oxo group Chemical group O=* 0.000 claims description 24
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 22
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
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• 125000005842 heteroatom Chemical group 0.000 claims description 15
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
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• YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 11
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
• 229910052697 platinum Inorganic materials 0.000 claims description 11
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 11
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• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
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• AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 claims description 8
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 8
• DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
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• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 6
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• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 6
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
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• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 6
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• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 206010009944 Colon cancer Diseases 0.000 claims description 5
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
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• 239000003242 anti bacterial agent Substances 0.000 claims description 5
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• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• 239000005551 L01XE03 - Erlotinib Substances 0.000 claims description 4
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• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
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• 125000001188 haloalkyl group Chemical group 0.000 claims description 4
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• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
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• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
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