TW201113284A - Heterocyclic oxime compounds - Google Patents

Info

Publication number

TW201113284A

TW201113284A TW099127805A TW99127805A TW201113284A TW 201113284 A TW201113284 A TW 201113284A TW 099127805 A TW099127805 A TW 099127805A TW 99127805 A TW99127805 A TW 99127805A TW 201113284 A TW201113284 A TW 201113284A

Authority

TW

Taiwan

Prior art keywords

group

compound

mmol

alkyl

etoac

Prior art date

2009-08-20

Links

• Espacenet
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• -1 Heterocyclic oxime compounds Chemical class 0.000 title claims description 178
• 150000001875 compounds Chemical class 0.000 claims abstract description 434
• 150000003839 salts Chemical class 0.000 claims abstract description 74
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 65
• 239000003814 drug Substances 0.000 claims abstract description 64
• 201000010099 disease Diseases 0.000 claims abstract description 59
• 238000011282 treatment Methods 0.000 claims abstract description 50
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
• 238000004519 manufacturing process Methods 0.000 claims abstract description 9
• 230000001404 mediated effect Effects 0.000 claims abstract description 7
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 115
• 125000000217 alkyl group Chemical group 0.000 claims description 91
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
• 125000001424 substituent group Chemical group 0.000 claims description 69
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• 239000001257 hydrogen Substances 0.000 claims description 37
• 125000005843 halogen group Chemical group 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 239000003795 chemical substances by application Substances 0.000 claims description 22
• 125000004435 hydrogen atom Chemical group [H]* 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 21
• 229920006395 saturated elastomer Polymers 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 108091000080 Phosphotransferase Proteins 0.000 claims description 18
• 102000020233 phosphotransferase Human genes 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 claims description 14
• 125000004429 atom Chemical group 0.000 claims description 13
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
• 239000000126 substance Substances 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 239000013543 active substance Substances 0.000 claims description 12
• 125000001153 fluoro group Chemical group F* 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 150000002923 oximes Chemical class 0.000 claims description 9
• 230000002062 proliferating effect Effects 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 7
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
• 229910052805 deuterium Inorganic materials 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 101150010802 CVC2 gene Proteins 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 4
• 125000002950 monocyclic group Chemical group 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 239000000758 substrate Substances 0.000 claims description 4
• 125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims description 4
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
• 239000004472 Lysine Substances 0.000 claims description 3
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 230000004968 inflammatory condition Effects 0.000 claims description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
• GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
• 125000006612 decyloxy group Chemical group 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000006413 ring segment Chemical group 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 5
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 3
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
• 239000001888 Peptone Substances 0.000 claims 1
• 108010080698 Peptones Proteins 0.000 claims 1
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• 230000008569 process Effects 0.000 abstract description 6
• 241000282414 Homo sapiens Species 0.000 abstract description 5
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 321
• 239000000243 solution Substances 0.000 description 190
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 186
• 235000019439 ethyl acetate Nutrition 0.000 description 165
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 155
• 239000000203 mixture Substances 0.000 description 138
• 239000002904 solvent Substances 0.000 description 107
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 94
• 239000000543 intermediate Substances 0.000 description 89
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 82
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 73
• 238000005160 1H NMR spectroscopy Methods 0.000 description 72
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 70
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 65
• 230000015572 biosynthetic process Effects 0.000 description 65
• 239000011541 reaction mixture Substances 0.000 description 64
• 230000000694 effects Effects 0.000 description 62
• 238000003786 synthesis reaction Methods 0.000 description 62
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 58
• 230000002829 reductive effect Effects 0.000 description 49
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 48
• 239000002585 base Substances 0.000 description 48
• 238000005481 NMR spectroscopy Methods 0.000 description 46
• 239000007787 solid Substances 0.000 description 46
• 101150041968 CDC13 gene Proteins 0.000 description 44
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 43
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
• 238000006243 chemical reaction Methods 0.000 description 42
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
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• 206010028980 Neoplasm Diseases 0.000 description 33
• 239000007789 gas Chemical group 0.000 description 30
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 28
• 238000003756 stirring Methods 0.000 description 27
• 239000003112 inhibitor Substances 0.000 description 26
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 26
• 239000013078 crystal Substances 0.000 description 25
• 239000002253 acid Substances 0.000 description 23
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 21
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• 235000003702 sterols Nutrition 0.000 description 17
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
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