JP2011517316A - β２−アドレナリン受容体アゴニストとしての４−（２−アミノ−１−ヒドロキシエチル）フェノールの誘導体 - Google Patents

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Publication number

JP2011517316A

JP2011517316A JP2010548032A JP2010548032A JP2011517316A JP 2011517316 A JP2011517316 A JP 2011517316A JP 2010548032 A JP2010548032 A JP 2010548032A JP 2010548032 A JP2010548032 A JP 2010548032A JP 2011517316 A JP2011517316 A JP 2011517316A

Authority

JP

Japan

Prior art keywords

hydroxy

ethyl

phenyl

amino

urea

Prior art date

2008-02-28

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.)

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• 102000016966 beta-2 Adrenergic Receptors Human genes 0.000 title claims description 22
• 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 title claims description 22
• 239000000048 adrenergic agonist Substances 0.000 title description 9
• 229940126157 adrenergic receptor agonist Drugs 0.000 title description 9
• QHGUCRYDKWKLMG-UHFFFAOYSA-N octopamine Chemical class NCC(O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 274
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 193
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
• 125000001424 substituent group Chemical group 0.000 claims abstract description 29
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 26
• 150000003839 salts Chemical class 0.000 claims abstract description 26
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 22
• 125000003118 aryl group Chemical group 0.000 claims abstract description 19
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
• 239000012453 solvate Substances 0.000 claims abstract description 11
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
• 125000004104 aryloxy group Chemical group 0.000 claims abstract description 9
• 125000005843 halogen group Chemical group 0.000 claims abstract description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims abstract description 5
• 125000003367 polycyclic group Chemical group 0.000 claims abstract description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
• -1 phenyloxy group Chemical group 0.000 claims description 186
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 136
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 120
• 239000000203 mixture Substances 0.000 claims description 94
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 63
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• 239000008194 pharmaceutical composition Substances 0.000 claims description 17
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• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
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• PYWNXSDTPRPTMD-LOGQOBJBSA-N 1-[3-[2-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]propyl]phenyl]-3-(2-phenylphenyl)urea Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NC(C)CC(C=1)=CC=CC=1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 PYWNXSDTPRPTMD-LOGQOBJBSA-N 0.000 claims description 5
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• RHAYOMZUUNTCTB-LJAQVGFWSA-N 1-benzhydryl-3-[3-[2-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]ethyl]phenyl]urea Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1NC(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 RHAYOMZUUNTCTB-LJAQVGFWSA-N 0.000 claims description 3
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• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• CRENOMPMIHKRCK-LJAQVGFWSA-N n-[2-hydroxy-5-[(1r)-1-hydroxy-2-[2-[3-[(2-phenylphenyl)carbamoylamino]phenyl]ethylamino]ethyl]phenyl]formamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NCCC(C=1)=CC=CC=1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 CRENOMPMIHKRCK-LJAQVGFWSA-N 0.000 claims description 3
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 156
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• 238000004440 column chromatography Methods 0.000 description 75
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 74
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