JP5506788B2 - 置換４−（インダゾリル）−１，４−ジヒドロピリジン類およびそれらの使用方法 - Google Patents

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Publication number

JP5506788B2

JP5506788B2 JP2011512860A JP2011512860A JP5506788B2 JP 5506788 B2 JP5506788 B2 JP 5506788B2 JP 2011512860 A JP2011512860 A JP 2011512860A JP 2011512860 A JP2011512860 A JP 2011512860A JP 5506788 B2 JP5506788 B2 JP 5506788B2

Authority

JP

Japan

Prior art keywords

group

alkyl

alkylamino

amino

cycloalkyl

Prior art date

2008-06-09

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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• 238000000034 method Methods 0.000 title claims description 102
• YKZJPQSQSIKVBV-UHFFFAOYSA-N 3-(1,4-dihydropyridin-4-yl)-2h-indazole Chemical class C1=CNC=CC1C1=C2C=CC=CC2=NN1 YKZJPQSQSIKVBV-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 228
• -1 bromo, difluoromethyl Chemical group 0.000 claims description 136
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 73
• 125000001153 fluoro group Chemical group F* 0.000 claims description 70
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
• 125000001424 substituent group Chemical group 0.000 claims description 54
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 50
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• 239000001257 hydrogen Substances 0.000 claims description 47
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 46
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 37
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
• 125000004043 oxo group Chemical group O=* 0.000 claims description 35
• 206010028980 Neoplasm Diseases 0.000 claims description 31
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
• 238000006243 chemical reaction Methods 0.000 claims description 28
• 229910052757 nitrogen Inorganic materials 0.000 claims description 25
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 24
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 24
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
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• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
• 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 claims description 9
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• YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical compound C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 claims description 7
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 7
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• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 5
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• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
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• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 65
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• 238000004007 reversed phase HPLC Methods 0.000 description 45
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• 210000004027 cell Anatomy 0.000 description 42
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• 230000002829 reductive effect Effects 0.000 description 38
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• 238000000746 purification Methods 0.000 description 33
• PKSCRDHECCYAAM-UHFFFAOYSA-N 2-[[5-(1,3-dioxolan-2-yl)-3-iodoindazol-1-yl]methoxy]ethyl-trimethylsilane Chemical group C=1C=C2N(COCC[Si](C)(C)C)N=C(I)C2=CC=1C1OCCO1 PKSCRDHECCYAAM-UHFFFAOYSA-N 0.000 description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
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