JP2005511508A5 - - Google Patents

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Publication number

JP2005511508A5

JP2005511508A5 JP2003528536A JP2003528536A JP2005511508A5 JP 2005511508 A5 JP2005511508 A5 JP 2005511508A5 JP 2003528536 A JP2003528536 A JP 2003528536A JP 2003528536 A JP2003528536 A JP 2003528536A JP 2005511508 A5 JP2005511508 A5 JP 2005511508A5

Authority

JP

Japan

Prior art keywords

alkyl

compound

formula

aryl

hydrogen

Prior art date

2002-09-11

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.)

Granted

Links

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• 125000000217 alkyl group Chemical group 0.000 claims 59
• 150000001875 compounds Chemical class 0.000 claims 49
• 125000003118 aryl group Chemical group 0.000 claims 31
• 229910052739 hydrogen Inorganic materials 0.000 claims 30
• 239000001257 hydrogen Substances 0.000 claims 30
• 150000003839 salts Chemical class 0.000 claims 29
• 239000012453 solvate Substances 0.000 claims 29
• 229910052736 halogen Inorganic materials 0.000 claims 18
• 150000002367 halogens Chemical class 0.000 claims 18
• 125000001072 heteroaryl group Chemical group 0.000 claims 18
• 150000002431 hydrogen Chemical class 0.000 claims 18
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 10
• 125000003545 alkoxy group Chemical group 0.000 claims 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 8
• 125000006239 protecting group Chemical group 0.000 claims 8
• -1 4-((R) -2- {6- [2- (2,6-dichlorobenzyloxy) -ethoxy] -hexylamino} -1-hydroxyethyl) -2-hydroxymethyl-phenol α-phenylcinnamic acid salt Chemical class 0.000 claims 5
• 230000001225 therapeutic effect Effects 0.000 claims 5
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 4
• 125000004432 carbon atom Chemical group C* 0.000 claims 4
• 229910052757 nitrogen Inorganic materials 0.000 claims 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
• 239000002243 precursor Substances 0.000 claims 4
• 229920006395 saturated elastomer Polymers 0.000 claims 4
• 239000004615 ingredient Substances 0.000 claims 3
• DAFYYTQWSAWIGS-DEOSSOPVSA-N vilanterol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCCOCCOCC=2C(=CC=CC=2Cl)Cl)=C1 DAFYYTQWSAWIGS-DEOSSOPVSA-N 0.000 claims 3
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 2
• 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 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
• 239000002253 acid Substances 0.000 claims 2
• 150000001412 amines Chemical class 0.000 claims 2
• 125000004104 aryloxy group Chemical group 0.000 claims 2
• 125000001188 haloalkyl group Chemical group 0.000 claims 2
• 238000000034 method Methods 0.000 claims 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
• 125000001424 substituent group Chemical group 0.000 claims 2
• YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
• HYJZGLOLVOHGRY-LJAQVGFWSA-N 1-[3-[2-[5-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]pentoxy]ethoxymethyl]phenyl]-3-phenylurea Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCOCCOCC=2C=C(NC(=O)NC=3C=CC=CC=3)C=CC=2)=C1 HYJZGLOLVOHGRY-LJAQVGFWSA-N 0.000 claims 1
• PYIBXZPZFHXOST-PMERELPUSA-N 1-[3-[2-[6-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]hexoxy]ethoxymethyl]phenyl]-3-phenylurea Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCCOCCOCC=2C=C(NC(=O)NC=3C=CC=CC=3)C=CC=2)=C1 PYIBXZPZFHXOST-PMERELPUSA-N 0.000 claims 1
• ZXQRIBVIRUROHJ-DEOSSOPVSA-N 4-[(1r)-1-hydroxy-2-[6-[2-[(3-hydroxyphenyl)methoxy]ethoxy]hexylamino]ethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCCOCCOCC=2C=C(O)C=CC=2)=C1 ZXQRIBVIRUROHJ-DEOSSOPVSA-N 0.000 claims 1
• YGPLZKHGYBRUPZ-SANMLTNESA-N 4-[(1r)-2-[6-[2-[(3,5-dimethylphenyl)methoxy]ethoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound CC1=CC(C)=CC(COCCOCCCCCCNC[C@H](O)C=2C=C(CO)C(O)=CC=2)=C1 YGPLZKHGYBRUPZ-SANMLTNESA-N 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
• 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 1
• RVKZZBUDWBBMCG-JMBOZCNDSA-N OCC(C=C([C@H](CNCCCCCCOCCOCC(C(Cl)=CC=C1)=C1Cl)O)C=C1)=C1O.O[C@@H](C(O)=O)C1=CC=CC=C1 Chemical compound OCC(C=C([C@H](CNCCCCCCOCCOCC(C(Cl)=CC=C1)=C1Cl)O)C=C1)=C1O.O[C@@H](C(O)=O)C1=CC=CC=C1 RVKZZBUDWBBMCG-JMBOZCNDSA-N 0.000 claims 1
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 1
• YTHPOCWIEYYGCI-XIFFEERXSA-N [4-[(1r)-2-[6-[2-[(2,6-dichlorophenyl)methoxy]ethoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenyl] naphthalene-1-carboxylate Chemical compound C([C@H](O)C=1C=C(C(=CC=1)OC(=O)C=1C2=CC=CC=C2C=CC=1)CO)NCCCCCCOCCOCC1=C(Cl)C=CC=C1Cl YTHPOCWIEYYGCI-XIFFEERXSA-N 0.000 claims 1
• 239000000048 adrenergic agonist Substances 0.000 claims 1
• 229940126157 adrenergic receptor agonist Drugs 0.000 claims 1
• 230000002152 alkylating effect Effects 0.000 claims 1
• 239000000812 cholinergic antagonist Substances 0.000 claims 1
• 238000007796 conventional method Methods 0.000 claims 1
• 239000003246 corticosteroid Substances 0.000 claims 1
• NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 claims 1
• 239000003814 drug Substances 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 238000013160 medical therapy Methods 0.000 claims 1
• 239000000203 mixture Substances 0.000 claims 1
• JDUWVWHYHBGVGT-DHUJRADRSA-N n-[3-[[3-[2-[6-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]hexoxy]ethoxymethyl]phenyl]carbamoylamino]phenyl]pyridine-3-carboxamide Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCCOCCOCC=2C=C(NC(=O)NC=3C=C(NC(=O)C=4C=NC=CC=4)C=CC=3)C=CC=2)=C1 JDUWVWHYHBGVGT-DHUJRADRSA-N 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 239000000546 pharmaceutical excipient Substances 0.000 claims 1
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
• 230000035479 physiological effects, processes and functions Effects 0.000 claims 1
• 230000035790 physiological processes and functions Effects 0.000 claims 1
• 230000002265 prevention Effects 0.000 claims 1
• 238000006268 reductive amination reaction Methods 0.000 claims 1