TW200404070A - Benzofused heteroaryl amide derivatives of thienopyridines useful as therapeutic agents, pharmaceutical compositions including the same, and methods for their use - Google Patents

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Publication number

TW200404070A

TW200404070A TW092116098A TW92116098A TW200404070A TW 200404070 A TW200404070 A TW 200404070A TW 092116098 A TW092116098 A TW 092116098A TW 92116098 A TW92116098 A TW 92116098A TW 200404070 A TW200404070 A TW 200404070A

Authority

TW

Taiwan

Prior art keywords

mmol

hydrogen

group

alkyl

nitrogen

Prior art date

2002-06-14

Links

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 31
• -1 heteroaryl amide Chemical class 0.000 title claims description 167
• 239000003814 drug Substances 0.000 title claims description 35
• 238000000034 method Methods 0.000 title abstract description 63
• 229940124597 therapeutic agent Drugs 0.000 title description 2
• 229940125670 thienopyridine Drugs 0.000 title 1
• 239000002175 thienopyridine Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 190
• 150000003839 salts Chemical class 0.000 claims abstract description 70
• 239000000651 prodrug Substances 0.000 claims abstract description 69
• 229940002612 prodrug Drugs 0.000 claims abstract description 69
• 239000012453 solvate Substances 0.000 claims abstract description 36
• 239000002207 metabolite Substances 0.000 claims abstract description 30
• 241000124008 Mammalia Species 0.000 claims abstract description 24
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 406
• 239000001257 hydrogen Substances 0.000 claims description 232
• 229910052739 hydrogen Inorganic materials 0.000 claims description 232
• 229910052757 nitrogen Inorganic materials 0.000 claims description 212
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 180
• 229910052717 sulfur Inorganic materials 0.000 claims description 79
• 239000011593 sulfur Substances 0.000 claims description 79
• 239000000126 substance Substances 0.000 claims description 75
• 125000000217 alkyl group Chemical group 0.000 claims description 68
• 125000000623 heterocyclic group Chemical group 0.000 claims description 67
• 150000002431 hydrogen Chemical group 0.000 claims description 46
• 125000001424 substituent group Chemical group 0.000 claims description 38
• 125000003118 aryl group Chemical group 0.000 claims description 35
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
• 239000003795 chemical substances by application Substances 0.000 claims description 33
• 201000010099 disease Diseases 0.000 claims description 33
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
• 206010028980 Neoplasm Diseases 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 229940079593 drug Drugs 0.000 claims description 22
• 201000011510 cancer Diseases 0.000 claims description 19
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 239000001301 oxygen Substances 0.000 claims description 18
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 14
• 230000033115 angiogenesis Effects 0.000 claims description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims description 12
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
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• 208000026310 Breast neoplasm Diseases 0.000 claims description 9
• 125000004122 cyclic group Chemical group 0.000 claims description 9
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• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 7
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
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• 208000020816 lung neoplasm Diseases 0.000 claims description 7
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 7
• 201000002528 pancreatic cancer Diseases 0.000 claims description 7
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
• 208000029742 colonic neoplasm Diseases 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 206010060862 Prostate cancer Diseases 0.000 claims description 5
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• 125000005189 alkyl hydroxy group Chemical group 0.000 claims description 5
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 5
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• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 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 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 206010033128 Ovarian cancer Diseases 0.000 claims description 4
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
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• 101100258315 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-1 gene Proteins 0.000 claims description 3
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
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• 239000002220 antihypertensive agent Substances 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
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• 208000032612 Glial tumor Diseases 0.000 claims description 2
• 208000007766 Kaposi sarcoma Diseases 0.000 claims description 2
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 2
• 230000036772 blood pressure Effects 0.000 claims description 2
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• 201000011066 hemangioma Diseases 0.000 claims description 2
• 208000002780 macular degeneration Diseases 0.000 claims description 2
• XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 claims description 2
• 208000017520 skin disease Diseases 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 4
• 101150072608 CVC1 gene Proteins 0.000 claims 2
• YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
• XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 claims 1
• ZMUITFUVZGNSKM-UHFFFAOYSA-N NC(=O)Nc1cccc-2c1Cc1ccccc-21 Chemical compound NC(=O)Nc1cccc-2c1Cc1ccccc-21 ZMUITFUVZGNSKM-UHFFFAOYSA-N 0.000 claims 1
• 208000017442 Retinal disease Diseases 0.000 claims 1
• 206010038923 Retinopathy Diseases 0.000 claims 1
• 101100137598 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PRM6 gene Proteins 0.000 claims 1
• 150000003973 alkyl amines Chemical class 0.000 claims 1
• 208000037893 chronic inflammatory disorder Diseases 0.000 claims 1
• 150000001924 cycloalkanes Chemical class 0.000 claims 1
• 230000008774 maternal effect Effects 0.000 claims 1
• 230000004060 metabolic process Effects 0.000 claims 1
• SAWKFRBJGLMMES-UHFFFAOYSA-N methylphosphine Chemical compound PC SAWKFRBJGLMMES-UHFFFAOYSA-N 0.000 claims 1
• 239000002831 pharmacologic agent Substances 0.000 claims 1
• 238000006467 substitution reaction Methods 0.000 claims 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
• 230000005747 tumor angiogenesis Effects 0.000 claims 1
• 229910052799 carbon Inorganic materials 0.000 description 211
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 206
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 185
• 239000007787 solid Substances 0.000 description 154
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 138
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 128
• 238000005481 NMR spectroscopy Methods 0.000 description 118
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
• 239000000463 material Substances 0.000 description 98
• 239000000243 solution Substances 0.000 description 97
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 90
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 89
• 238000006243 chemical reaction Methods 0.000 description 86
• 229910001868 water Inorganic materials 0.000 description 80
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 76
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 69
• 239000002253 acid Substances 0.000 description 67
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 65
• 239000000203 mixture Substances 0.000 description 63
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 62
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 60
• 101150041968 CDC13 gene Proteins 0.000 description 59
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 57
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
• 238000005160 1H NMR spectroscopy Methods 0.000 description 50
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 50
• 239000007789 gas Substances 0.000 description 50
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 49
• 229910000024 caesium carbonate Inorganic materials 0.000 description 49
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 45
• 239000011541 reaction mixture Substances 0.000 description 44
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
• 238000011282 treatment Methods 0.000 description 38
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 37
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 30
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 30
• 239000012044 organic layer Substances 0.000 description 30
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 30
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
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