TW201249858A - Substituted indole derivatives - Google Patents

Info

Publication number

TW201249858A

TW201249858A TW101117465A TW101117465A TW201249858A TW 201249858 A TW201249858 A TW 201249858A TW 101117465 A TW101117465 A TW 101117465A TW 101117465 A TW101117465 A TW 101117465A TW 201249858 A TW201249858 A TW 201249858A

Authority

TW

Taiwan

Prior art keywords

compound

disease

formula

alkyl

pharmaceutically acceptable

Prior art date

2011-05-17

Links

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• 229940054051 antipsychotic indole derivative Drugs 0.000 title abstract 2
• 150000002475 indoles Chemical class 0.000 title abstract 2
• 238000000034 method Methods 0.000 claims abstract description 20
• 239000003814 drug Substances 0.000 claims abstract description 18
• 150000001875 compounds Chemical class 0.000 claims description 109
• 150000003839 salts Chemical class 0.000 claims description 55
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
• 201000010099 disease Diseases 0.000 claims description 31
• 125000000217 alkyl group Chemical group 0.000 claims description 27
• WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 22
• 238000012360 testing method Methods 0.000 claims description 22
• -1 oct-7-yl Chemical group 0.000 claims description 21
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
• 206010028980 Neoplasm Diseases 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 18
• 102000003923 Protein Kinase C Human genes 0.000 claims description 14
• 108090000315 Protein Kinase C Proteins 0.000 claims description 14
• 239000002904 solvent Substances 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 229940079593 drug Drugs 0.000 claims description 12
• 150000004682 monohydrates Chemical class 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 11
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 11
• 229910019142 PO4 Inorganic materials 0.000 claims description 10
• 230000001154 acute effect Effects 0.000 claims description 10
• 239000010452 phosphate Substances 0.000 claims description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 150000002148 esters Chemical class 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 9
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 210000000056 organ Anatomy 0.000 claims description 7
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
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• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 6
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• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
• YEWZQCDRZRYAEB-UHFFFAOYSA-M ditert-butyl phosphate Chemical compound CC(C)(C)OP([O-])(=O)OC(C)(C)C YEWZQCDRZRYAEB-UHFFFAOYSA-M 0.000 claims description 4
• 239000012467 final product Substances 0.000 claims description 4
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• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
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• PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 2
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• YEWZQCDRZRYAEB-UHFFFAOYSA-N ditert-butyl hydrogen phosphate Chemical compound CC(C)(C)OP(O)(=O)OC(C)(C)C YEWZQCDRZRYAEB-UHFFFAOYSA-N 0.000 claims description 2
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• 150000002431 hydrogen Chemical class 0.000 claims 3
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• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
• 238000006751 Mitsunobu reaction Methods 0.000 claims 1
• 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
• 206010003246 arthritis Diseases 0.000 claims 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
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• 239000013078 crystal Substances 0.000 description 18
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 16
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 15
• 235000019439 ethyl acetate Nutrition 0.000 description 15
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• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
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