NZ550222A - Diphenyl ox-indol-2-one compounds and their use in the treatment of cancer - Google Patents

Info

Publication number

NZ550222A

NZ550222A NZ550222A NZ55022205A NZ550222A NZ 550222 A NZ550222 A NZ 550222A NZ 550222 A NZ550222 A NZ 550222A NZ 55022205 A NZ55022205 A NZ 55022205A NZ 550222 A NZ550222 A NZ 550222A

Authority

NZ

New Zealand

Prior art keywords

phenyl

dihydro

hydroxy

bis

indol

Prior art date

2004-04-08

Links

• Espacenet
• Global Dossier
• Discuss

• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 50
• 201000011510 cancer Diseases 0.000 title claims abstract description 27
• 238000011282 treatment Methods 0.000 title claims abstract description 18
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title description 3
• 235000010290 biphenyl Nutrition 0.000 title description 2
• 239000004305 biphenyl Substances 0.000 title description 2
• 125000006267 biphenyl group Chemical group 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 178
• 229910052739 hydrogen Inorganic materials 0.000 claims description 295
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 178
• -1 heterocyclylamino Chemical group 0.000 claims description 140
• 229910052736 halogen Inorganic materials 0.000 claims description 138
• 150000002367 halogens Chemical class 0.000 claims description 135
• 125000001072 heteroaryl group Chemical group 0.000 claims description 131
• 239000001257 hydrogen Substances 0.000 claims description 117
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 111
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 98
• 150000002431 hydrogen Chemical class 0.000 claims description 79
• 125000003118 aryl group Chemical group 0.000 claims description 78
• 125000000623 heterocyclic group Chemical group 0.000 claims description 66
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 65
• 125000003107 substituted aryl group Chemical group 0.000 claims description 53
• 150000003839 salts Chemical class 0.000 claims description 50
• 229940002612 prodrug Drugs 0.000 claims description 42
• 239000000651 prodrug Substances 0.000 claims description 42
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 41
• 125000004104 aryloxy group Chemical group 0.000 claims description 34
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 32
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 22
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
• 238000002360 preparation method Methods 0.000 claims description 18
• 125000001769 aryl amino group Chemical group 0.000 claims description 16
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 16
• 125000001153 fluoro group Chemical group F* 0.000 claims description 16
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 15
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 15
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 15
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 15
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• 241000124008 Mammalia Species 0.000 claims description 12
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 11
• 150000002148 esters Chemical class 0.000 claims description 11
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 239000002246 antineoplastic agent Substances 0.000 claims description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 6
• 229940127089 cytotoxic agent Drugs 0.000 claims description 6
• QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 claims description 6
• USEUWHHNJDYNIQ-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-2-oxo-1h-indole-7-carbonitrile Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C(C=CC=C2C#N)=C2NC1=O USEUWHHNJDYNIQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000001246 bromo group Chemical group Br* 0.000 claims description 5
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 5
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• YXZMOBOEBXLVAF-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-n,n-dimethyl-2-oxo-1h-indole-7-carboxamide Chemical compound CN(C)C(=O)C1=CC=CC2=C1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 YXZMOBOEBXLVAF-UHFFFAOYSA-N 0.000 claims description 2
• WMNXCYJFMWJJFP-UHFFFAOYSA-N [4-[6-chloro-7-cyclopropyl-3-[4-[2-(dimethylamino)acetyl]oxyphenyl]-2-oxo-1h-indol-3-yl]phenyl] 2-(dimethylamino)acetate Chemical compound C1=CC(OC(=O)CN(C)C)=CC=C1C1(C=2C=CC(OC(=O)CN(C)C)=CC=2)C(C=CC(Cl)=C2C3CC3)=C2NC1=O WMNXCYJFMWJJFP-UHFFFAOYSA-N 0.000 claims description 2
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• 125000005843 halogen group Chemical group 0.000 claims 3
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• OYRCMPWQHODZMZ-UHFFFAOYSA-N [4-[3-(4-acetyloxyphenyl)-6-chloro-4,7-dimethyl-2-oxo-1h-indol-3-yl]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1(C=2C=CC(OC(C)=O)=CC=2)C(C(C)=CC(Cl)=C2C)=C2NC1=O OYRCMPWQHODZMZ-UHFFFAOYSA-N 0.000 claims 2
• XQKBUNIECXVVHV-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-2-oxo-1h-indole-5-carboxylic acid Chemical compound C12=CC(C(=O)O)=CC=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 XQKBUNIECXVVHV-UHFFFAOYSA-N 0.000 claims 1
• MINJJGVMKXDFMX-UHFFFAOYSA-N 6-chloro-3,3-bis(4-hydroxyphenyl)-7-methoxy-2-oxo-1h-indole-5-carbonitrile Chemical compound C12=CC(C#N)=C(Cl)C(OC)=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 MINJJGVMKXDFMX-UHFFFAOYSA-N 0.000 claims 1
• 240000007594 Oryza sativa Species 0.000 claims 1
• 235000007164 Oryza sativa Nutrition 0.000 claims 1
• SYJUHGJHXDDMGD-UHFFFAOYSA-N [4-[3-(4-acetyloxyphenyl)-6-chloro-7-cyclopropyl-2-oxo-1h-indol-3-yl]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1(C=2C=CC(OC(C)=O)=CC=2)C(C=CC(Cl)=C2C3CC3)=C2NC1=O SYJUHGJHXDDMGD-UHFFFAOYSA-N 0.000 claims 1
• ZEJVIQRTBRXTEV-UHFFFAOYSA-N [4-[3-(4-acetyloxyphenyl)-6-chloro-7-cyclopropyloxy-2-oxo-1h-indol-3-yl]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1(C=2C=CC(OC(C)=O)=CC=2)C(C=CC(Cl)=C2OC3CC3)=C2NC1=O ZEJVIQRTBRXTEV-UHFFFAOYSA-N 0.000 claims 1
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
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