JP5805653B2 - トリアゾロピリジン - Google Patents

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Publication number

JP5805653B2

JP5805653B2 JP2012541336A JP2012541336A JP5805653B2 JP 5805653 B2 JP5805653 B2 JP 5805653B2 JP 2012541336 A JP2012541336 A JP 2012541336A JP 2012541336 A JP2012541336 A JP 2012541336A JP 5805653 B2 JP5805653 B2 JP 5805653B2

Authority

JP

Japan

Prior art keywords

alkyl

alkoxy

halo

group

compound

Prior art date

2009-11-30

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 title 1
• -1 hydroxyl- Chemical group 0.000 claims description 335
• 150000001875 compounds Chemical class 0.000 claims description 254
• 239000000203 mixture Substances 0.000 claims description 151
• 125000005843 halogen group Chemical group 0.000 claims description 73
• 150000003839 salts Chemical class 0.000 claims description 48
• 238000000034 method Methods 0.000 claims description 46
• 125000001424 substituent group Chemical group 0.000 claims description 46
• 125000003118 aryl group Chemical group 0.000 claims description 44
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 41
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 38
• 238000011282 treatment Methods 0.000 claims description 31
• 201000010099 disease Diseases 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 23
• 239000012453 solvate Substances 0.000 claims description 20
• 238000006243 chemical reaction Methods 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
• 230000002265 prevention Effects 0.000 claims description 8
• 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 125000000524 functional group Chemical group 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 150000001502 aryl halides Chemical class 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
• 241000255925 Diptera Species 0.000 claims 1
• 230000001548 androgenic effect Effects 0.000 claims 1
• WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 claims 1
• 210000004027 cell Anatomy 0.000 description 88
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 72
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
• 239000000543 intermediate Substances 0.000 description 58
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• 239000002904 solvent Substances 0.000 description 53
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
• 238000004519 manufacturing process Methods 0.000 description 42
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
• 230000005778 DNA damage Effects 0.000 description 11
• 231100000277 DNA damage Toxicity 0.000 description 11
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 11
• 125000006239 protecting group Chemical group 0.000 description 11
• 238000012360 testing method Methods 0.000 description 11
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
• 238000007792 addition Methods 0.000 description 10
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
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• CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 9
• 125000002619 bicyclic group Chemical group 0.000 description 9
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