TW200829586A - Aza-indolyl compounds and methods of use - Google Patents

Info

Publication number

TW200829586A

TW200829586A TW096145474A TW96145474A TW200829586A TW 200829586 A TW200829586 A TW 200829586A TW 096145474 A TW096145474 A TW 096145474A TW 96145474 A TW96145474 A TW 96145474A TW 200829586 A TW200829586 A TW 200829586A

Authority

TW

Taiwan

Prior art keywords

alkyl

cr19r20

group

compound

doc

Prior art date

2006-11-30

Links

• Espacenet
• Global Dossier
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• 238000000034 method Methods 0.000 title abstract description 138
• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 title abstract description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 223
• 241000124008 Mammalia Species 0.000 claims abstract description 36
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
• 238000011282 treatment Methods 0.000 claims abstract description 28
• 230000002159 abnormal effect Effects 0.000 claims abstract description 14
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 11
• 230000010261 cell growth Effects 0.000 claims abstract description 10
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 8
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 252
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 55
• 150000003839 salts Chemical class 0.000 claims description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• 125000000623 heterocyclic group Chemical group 0.000 claims description 35
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 35
• 125000003118 aryl group Chemical group 0.000 claims description 33
• 229920006395 saturated elastomer Polymers 0.000 claims description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• 125000005843 halogen group Chemical group 0.000 claims description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 13
• 229940127089 cytotoxic agent Drugs 0.000 claims description 13
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• 239000002246 antineoplastic agent Substances 0.000 claims description 12
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 11
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 9
• 239000000126 substance Substances 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• 229910052707 ruthenium Inorganic materials 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 229910006074 SO2NH2 Inorganic materials 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
• 125000003544 oxime group Chemical group 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 118
• 230000000694 effects Effects 0.000 abstract description 11
• 238000001727 in vivo Methods 0.000 abstract description 7
• 238000003745 diagnosis Methods 0.000 abstract description 4
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• 102000001291 MAP Kinase Kinase Kinase Human genes 0.000 abstract description 3
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• 230000001093 anti-cancer Effects 0.000 abstract description 3
• 238000000338 in vitro Methods 0.000 abstract description 3
• 238000011065 in-situ storage Methods 0.000 abstract description 3
• 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 405
• 235000019439 ethyl acetate Nutrition 0.000 description 181
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
• -1 azaindole compound Chemical class 0.000 description 144
• 239000000243 solution Substances 0.000 description 111
• 206010057190 Respiratory tract infections Diseases 0.000 description 105
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 104
• 239000002904 solvent Substances 0.000 description 103
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• SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 82
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 79
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 72
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 67
• 239000011541 reaction mixture Substances 0.000 description 67
• 239000002585 base Substances 0.000 description 60
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 56
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 44
• 210000004027 cell Anatomy 0.000 description 44
• 238000006243 chemical reaction Methods 0.000 description 44
• 239000002253 acid Substances 0.000 description 40
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
• 239000007787 solid Substances 0.000 description 37
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• 239000012044 organic layer Substances 0.000 description 36
• FQYYIPZPELSLDK-UHFFFAOYSA-N ethyl pyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC=N1 FQYYIPZPELSLDK-UHFFFAOYSA-N 0.000 description 35
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 34
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 34
• 150000001412 amines Chemical class 0.000 description 34
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
• 229910052740 iodine Inorganic materials 0.000 description 31
• 206010028980 Neoplasm Diseases 0.000 description 29
• 238000003818 flash chromatography Methods 0.000 description 28
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 28
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 238000010992 reflux Methods 0.000 description 27
• 238000005481 NMR spectroscopy Methods 0.000 description 26
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• 235000019198 oils Nutrition 0.000 description 26
• 201000010099 disease Diseases 0.000 description 24
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 24
• 238000003556 assay Methods 0.000 description 23
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• 201000011510 cancer Diseases 0.000 description 20
• 239000007789 gas Substances 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• 238000007792 addition Methods 0.000 description 17
• 239000012267 brine Substances 0.000 description 17
• 229910052739 hydrogen Inorganic materials 0.000 description 17
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 239000012453 solvate Substances 0.000 description 16
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 15
• 108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 description 15
• 102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 description 15
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• 239000010410 layer Substances 0.000 description 14
• 230000026731 phosphorylation Effects 0.000 description 14
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• 229910000104 sodium hydride Inorganic materials 0.000 description 14
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 13
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• 229910052799 carbon Inorganic materials 0.000 description 13
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 13
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• DNIORISUBCVZFN-UHFFFAOYSA-N OCCONCCCCCCCCCC Chemical compound OCCONCCCCCCCCCC DNIORISUBCVZFN-UHFFFAOYSA-N 0.000 description 12
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