JP6422986B2 - 化合物 - Google Patents

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Publication number

JP6422986B2

JP6422986B2 JP2016549028A JP2016549028A JP6422986B2 JP 6422986 B2 JP6422986 B2 JP 6422986B2 JP 2016549028 A JP2016549028 A JP 2016549028A JP 2016549028 A JP2016549028 A JP 2016549028A JP 6422986 B2 JP6422986 B2 JP 6422986B2

Authority

JP

Japan

Prior art keywords

mmol

pharmaceutically acceptable

methyl

lcms

compound

Prior art date

2014-01-29

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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• 150000001875 compounds Chemical class 0.000 title claims description 474
• 150000003839 salts Chemical class 0.000 claims description 188
• -1 tetrahydro-2H-pyranyl Chemical group 0.000 claims description 91
• 125000000217 alkyl group Chemical group 0.000 claims description 75
• 125000001424 substituent group Chemical group 0.000 claims description 73
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 54
• 229910052799 carbon Inorganic materials 0.000 claims description 52
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• 238000011282 treatment Methods 0.000 claims description 48
• 125000003566 oxetanyl group Chemical group 0.000 claims description 43
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
• 125000003545 alkoxy group Chemical group 0.000 claims description 34
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 27
• 229910052727 yttrium Inorganic materials 0.000 claims description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims description 25
• 125000002757 morpholinyl group Chemical group 0.000 claims description 21
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 15
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 12
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 10
• 125000003386 piperidinyl group Chemical group 0.000 claims description 9
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 4
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• RGLFLHRKZUNPAL-CQSZACIVSA-N N-[5-chloro-1-[(4R)-3,3-difluoro-1-(oxetan-3-yl)piperidin-4-yl]pyrazol-4-yl]-4-ethoxy-7H-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound ClC1=C(C=NN1[C@H]1C(CN(CC1)C1COC1)(F)F)NC=1N=C(C2=C(N=1)NC=C2)OCC RGLFLHRKZUNPAL-CQSZACIVSA-N 0.000 claims 3
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• 229920006395 saturated elastomer Polymers 0.000 description 24
• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 23
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• XORHNJQEWQGXCN-UHFFFAOYSA-N 4-nitro-1h-pyrazole Chemical compound [O-][N+](=O)C=1C=NNC=1 XORHNJQEWQGXCN-UHFFFAOYSA-N 0.000 description 20
• 239000003814 drug Substances 0.000 description 20
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• VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 20
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• KTMKRRPZPWUYKK-UHFFFAOYSA-N methylboronic acid Chemical compound CB(O)O KTMKRRPZPWUYKK-UHFFFAOYSA-N 0.000 description 15
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• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 13
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• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
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