JP2008507532A5 - - Google Patents
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- JP2008507532A5 JP2008507532A5 JP2007522685A JP2007522685A JP2008507532A5 JP 2008507532 A5 JP2008507532 A5 JP 2008507532A5 JP 2007522685 A JP2007522685 A JP 2007522685A JP 2007522685 A JP2007522685 A JP 2007522685A JP 2008507532 A5 JP2008507532 A5 JP 2008507532A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- phenyl
- ethylamino
- hydroxyethyl
- alkyl
- Prior art date
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 239000001257 hydrogen Substances 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 17
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 12
- -1 hydroxy, amino Chemical group 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 229940126585 therapeutic drug Drugs 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 229910052723 transition metal Inorganic materials 0.000 claims 2
- 150000003624 transition metals Chemical class 0.000 claims 2
- TUBIBLGODRGOHP-LJAQVGFWSA-N 2-(hydroxymethyl)-4-[(1r)-1-hydroxy-2-[2-[4-(3-phenylphenoxy)phenyl]ethylamino]ethyl]phenol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCC=2C=CC(OC=3C=C(C=CC=3)C=3C=CC=CC=3)=CC=2)=C1 TUBIBLGODRGOHP-LJAQVGFWSA-N 0.000 claims 1
- DFYRTAAGPOJRST-MHZLTWQESA-N 2-(hydroxymethyl)-4-[(1r)-1-hydroxy-2-[2-[4-(4-morpholin-4-ylphenoxy)phenyl]ethylamino]ethyl]phenol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCC=2C=CC(OC=3C=CC(=CC=3)N3CCOCC3)=CC=2)=C1 DFYRTAAGPOJRST-MHZLTWQESA-N 0.000 claims 1
- LOTCCABMGTVQJS-PMERELPUSA-N 3-[3-[4-[2-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]ethyl]phenoxy]phenyl]benzonitrile Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCC(C=C1)=CC=C1OC(C=1)=CC=CC=1C1=CC=CC(C#N)=C1 LOTCCABMGTVQJS-PMERELPUSA-N 0.000 claims 1
- QDZLKIKITHQUSC-UHFFFAOYSA-N 3-[5-[4-[2-[[2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]ethyl]phenoxy]-2-methoxyphenyl]benzonitrile Chemical compound COC1=CC=C(OC=2C=CC(CCNCC(O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)C=C1C1=CC=CC(C#N)=C1 QDZLKIKITHQUSC-UHFFFAOYSA-N 0.000 claims 1
- OPZBYTUCEDHACG-UHFFFAOYSA-N 3-[5-[4-[2-[[2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]ethyl]phenoxy]-2-methoxyphenyl]benzonitrile Chemical compound C1=C(C=2C=C(C=CC=2)C#N)C(OC)=CC=C1OC(C=C1)=CC=C1CCNCC(O)C1=CC=C(O)C(CO)=C1 OPZBYTUCEDHACG-UHFFFAOYSA-N 0.000 claims 1
- WKNSKEUOAINWIB-PMERELPUSA-N 4-[(1r)-2-[2-[4-[3-(2-amino-3-ethylphenyl)-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound CCC1=CC=CC(C=2C(=CC=C(OC=3C=CC(CCNC[C@H](O)C=4C=C(CO)C(O)=CC=4)=CC=3)C=2)OC)=C1N WKNSKEUOAINWIB-PMERELPUSA-N 0.000 claims 1
- BIJACFOADCGQPS-UHFFFAOYSA-N 4-[2-[2-[4-[3-(3-chlorophenyl)-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=CC=C1OC(C=C1)=CC=C1CCNCC(O)C1=CC=C(O)C(CO)=C1 BIJACFOADCGQPS-UHFFFAOYSA-N 0.000 claims 1
- FEUHUAULTZZUDS-UHFFFAOYSA-N 4-[2-[2-[4-[3-[3-(aminomethyl)phenyl]-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(C=2C=C(CN)C=CC=2)C(OC)=CC=C1OC(C=C1)=CC=C1CCNCC(O)C1=CC=C(O)C(CO)=C1 FEUHUAULTZZUDS-UHFFFAOYSA-N 0.000 claims 1
- AOQXKTOXEWJGKA-UHFFFAOYSA-N 4-[2-[2-[4-[3-[4-(aminomethyl)phenyl]-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(C=2C=CC(CN)=CC=2)C(OC)=CC=C1OC(C=C1)=CC=C1CCNCC(O)C1=CC=C(O)C(CO)=C1 AOQXKTOXEWJGKA-UHFFFAOYSA-N 0.000 claims 1
- JDBAEVYCCGMFJB-SANMLTNESA-N 5-[(1r)-2-[2-[4-[3-(3-aminopropyl)-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound C1=C(CCCN)C(OC)=CC=C1OC(C=C1)=CC=C1CCNC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 JDBAEVYCCGMFJB-SANMLTNESA-N 0.000 claims 1
- AAWRYASVGTWNRA-LJAQVGFWSA-N 5-[(1r)-2-[2-[4-[3-(4-chlorophenyl)phenoxy]phenyl]ethylamino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCC(C=C1)=CC=C1OC(C=1)=CC=CC=1C1=CC=C(Cl)C=C1 AAWRYASVGTWNRA-LJAQVGFWSA-N 0.000 claims 1
- YZWQATVPGZTCBD-MHZLTWQESA-N 5-[(1r)-2-[2-[4-[3-[2-(dimethylamino)ethyl]-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound C1=C(CCN(C)C)C(OC)=CC=C1OC(C=C1)=CC=C1CCNC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 YZWQATVPGZTCBD-MHZLTWQESA-N 0.000 claims 1
- XJFXXNRPCNSPIJ-HKBQPEDESA-N 5-[(1r)-2-[2-[4-[3-[3-(2-aminoethyl)phenyl]-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound COC1=CC=C(OC=2C=CC(CCNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)C=C1C1=CC=CC(CCN)=C1 XJFXXNRPCNSPIJ-HKBQPEDESA-N 0.000 claims 1
- KLKXMOLYQIGTCM-SANMLTNESA-N 5-[(1r)-2-[2-[4-[4-(2-amino-2-methylpropoxy)phenoxy]phenyl]ethylamino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound C1=CC(OCC(C)(N)C)=CC=C1OC(C=C1)=CC=C1CCNC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 KLKXMOLYQIGTCM-SANMLTNESA-N 0.000 claims 1
- AHLFSKLVFVYVKD-DEOSSOPVSA-N 5-[(1r)-2-[2-[4-[4-(2-aminoethoxy)-3-(trifluoromethyl)phenoxy]phenyl]ethylamino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound C1=C(C(F)(F)F)C(OCCN)=CC=C1OC(C=C1)=CC=C1CCNC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 AHLFSKLVFVYVKD-DEOSSOPVSA-N 0.000 claims 1
- ZTNDVILTNKGXJI-SANMLTNESA-N 5-[(1r)-2-[2-[4-[4-(3-aminopropoxy)phenoxy]phenyl]ethylamino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound C1=CC(OCCCN)=CC=C1OC(C=C1)=CC=C1CCNC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 ZTNDVILTNKGXJI-SANMLTNESA-N 0.000 claims 1
- BAYIKWRKACUIDC-MHZLTWQESA-N 5-[(1r)-2-[2-[4-[4-[2-(2-aminoethoxy)ethoxy]phenoxy]phenyl]ethylamino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound C1=CC(OCCOCCN)=CC=C1OC(C=C1)=CC=C1CCNC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 BAYIKWRKACUIDC-MHZLTWQESA-N 0.000 claims 1
- HASPUVUEEXNVQR-UHFFFAOYSA-N 5-[2-[2-[4-[3-(3-chlorophenyl)-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound COC1=CC=C(OC=2C=CC(CCNCC(O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)C=C1C1=CC=CC(Cl)=C1 HASPUVUEEXNVQR-UHFFFAOYSA-N 0.000 claims 1
- QJHFTPQALJUGNJ-UHFFFAOYSA-N 5-[2-[2-[4-[3-[3-(aminomethyl)phenyl]-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound COC1=CC=C(OC=2C=CC(CCNCC(O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)C=C1C1=CC=CC(CN)=C1 QJHFTPQALJUGNJ-UHFFFAOYSA-N 0.000 claims 1
- BTPGXMRGUSJMIG-UHFFFAOYSA-N 5-[2-[2-[4-[3-[4-(aminomethyl)phenyl]-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound COC1=CC=C(OC=2C=CC(CCNCC(O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)C=C1C1=CC=C(CN)C=C1 BTPGXMRGUSJMIG-UHFFFAOYSA-N 0.000 claims 1
- QSYYCQBSKYPHSB-LJAQVGFWSA-N 8-hydroxy-5-[(1r)-1-hydroxy-2-[2-[4-(3-phenylphenoxy)phenyl]ethylamino]ethyl]-1h-quinolin-2-one Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCC(C=C1)=CC=C1OC(C=1)=CC=CC=1C1=CC=CC=C1 QSYYCQBSKYPHSB-LJAQVGFWSA-N 0.000 claims 1
- GBGVPLDZRAUBBA-LJAQVGFWSA-N 8-hydroxy-5-[(1r)-1-hydroxy-2-[2-[4-(4-methoxy-3-phenylphenoxy)phenyl]ethylamino]ethyl]-1h-quinolin-2-one Chemical compound COC1=CC=C(OC=2C=CC(CCNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)C=C1C1=CC=CC=C1 GBGVPLDZRAUBBA-LJAQVGFWSA-N 0.000 claims 1
- QTVLQXVLVMAMDH-MHZLTWQESA-N 8-hydroxy-5-[(1r)-1-hydroxy-2-[2-[4-(4-morpholin-4-ylphenoxy)phenyl]ethylamino]ethyl]-1h-quinolin-2-one Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCC(C=C1)=CC=C1OC(C=C1)=CC=C1N1CCOCC1 QTVLQXVLVMAMDH-MHZLTWQESA-N 0.000 claims 1
- CUNUUUZDIGCWDT-PMERELPUSA-N 8-hydroxy-5-[(1r)-1-hydroxy-2-[2-[4-[3-(4-methoxyphenyl)phenoxy]phenyl]ethylamino]ethyl]-1h-quinolin-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(OC=2C=CC(CCNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)=C1 CUNUUUZDIGCWDT-PMERELPUSA-N 0.000 claims 1
- GLRBGNJHTNVYML-LJAQVGFWSA-N 8-hydroxy-5-[(1r)-1-hydroxy-2-[2-[4-[4-(2-morpholin-4-ylethoxy)phenoxy]phenyl]ethylamino]ethyl]-1h-quinolin-2-one Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCC(C=C1)=CC=C1OC(C=C1)=CC=C1OCCN1CCOCC1 GLRBGNJHTNVYML-LJAQVGFWSA-N 0.000 claims 1
- ZMHUSGJOZCHZBM-LJAQVGFWSA-N 8-hydroxy-5-[(1r)-1-hydroxy-2-[2-[4-[4-(2-piperazin-1-ylethoxy)phenoxy]phenyl]ethylamino]ethyl]-1h-quinolin-2-one Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCC(C=C1)=CC=C1OC(C=C1)=CC=C1OCCN1CCNCC1 ZMHUSGJOZCHZBM-LJAQVGFWSA-N 0.000 claims 1
- CIJIYHHKRIIRRI-UMSFTDKQSA-N 8-hydroxy-5-[(1r)-1-hydroxy-2-[2-[4-[4-methoxy-3-[3-(morpholin-4-ylmethyl)phenyl]phenoxy]phenyl]ethylamino]ethyl]-1h-quinolin-2-one Chemical compound COC1=CC=C(OC=2C=CC(CCNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)C=C1C(C=1)=CC=CC=1CN1CCOCC1 CIJIYHHKRIIRRI-UMSFTDKQSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 230000001078 anti-cholinergic effect Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 229960001334 corticosteroids Drugs 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- MCANLJLDYKNECQ-LJAQVGFWSA-N n-[2-hydroxy-5-[(1r)-1-hydroxy-2-[2-[4-(3-phenylphenoxy)phenyl]ethylamino]ethyl]phenyl]formamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NCCC(C=C1)=CC=C1OC(C=1)=CC=CC=1C1=CC=CC=C1 MCANLJLDYKNECQ-LJAQVGFWSA-N 0.000 claims 1
- SIVLLCMFRSBPLH-MHZLTWQESA-N n-[5-[(1r)-2-[2-[4-[3-[2-(dimethylamino)ethyl]-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]formamide Chemical compound C1=C(CCN(C)C)C(OC)=CC=C1OC(C=C1)=CC=C1CCNC[C@H](O)C1=CC=C(O)C(NC=O)=C1 SIVLLCMFRSBPLH-MHZLTWQESA-N 0.000 claims 1
- RLNZXSZYXZNWGQ-VWLOTQADSA-N n-[5-[(1r)-2-[2-[4-[4-(2-aminoethoxy)phenoxy]phenyl]ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]formamide Chemical compound C1=CC(OCCN)=CC=C1OC(C=C1)=CC=C1CCNC[C@H](O)C1=CC=C(O)C(NC=O)=C1 RLNZXSZYXZNWGQ-VWLOTQADSA-N 0.000 claims 1
- ASMRTVSGUNPMHW-UHFFFAOYSA-N n-[5-[2-[2-[4-[3-(3-chlorophenyl)-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]formamide Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=CC=C1OC(C=C1)=CC=C1CCNCC(O)C1=CC=C(O)C(NC=O)=C1 ASMRTVSGUNPMHW-UHFFFAOYSA-N 0.000 claims 1
- RFRFJILDRYFSSN-UHFFFAOYSA-N n-[5-[2-[2-[4-[3-[3-(aminomethyl)phenyl]-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]formamide Chemical compound C1=C(C=2C=C(CN)C=CC=2)C(OC)=CC=C1OC(C=C1)=CC=C1CCNCC(O)C1=CC=C(O)C(NC=O)=C1 RFRFJILDRYFSSN-UHFFFAOYSA-N 0.000 claims 1
- WJLANEUKLAWUQB-UHFFFAOYSA-N n-[5-[2-[2-[4-[3-[4-(aminomethyl)phenyl]-4-methoxyphenoxy]phenyl]ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]formamide Chemical compound C1=C(C=2C=CC(CN)=CC=2)C(OC)=CC=C1OC(C=C1)=CC=C1CCNCC(O)C1=CC=C(O)C(NC=O)=C1 WJLANEUKLAWUQB-UHFFFAOYSA-N 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 0 CC*(c1c(*=*)c(*)cc(C(C(C)*)OC)c1C(C)=*)=C Chemical compound CC*(c1c(*=*)c(*)cc(C(C(C)*)OC)c1C(C)=*)=C 0.000 description 3
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58972804P | 2004-07-21 | 2004-07-21 | |
| PCT/US2005/025690 WO2006014704A1 (en) | 2004-07-21 | 2005-07-20 | DIARYL ETHER β2 ADRENERGIC RECEPTOR AGONISTS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008507532A JP2008507532A (ja) | 2008-03-13 |
| JP2008507532A5 true JP2008507532A5 (enExample) | 2008-08-07 |
Family
ID=35064743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007522685A Withdrawn JP2008507532A (ja) | 2004-07-21 | 2005-07-20 | ジアリールエーテルβ２アドレナリン作用性レセプターアゴニスト |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US7317023B2 (enExample) |
| EP (1) | EP1778638A1 (enExample) |
| JP (1) | JP2008507532A (enExample) |
| WO (1) | WO2006014704A1 (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI249515B (en) * | 2001-11-13 | 2006-02-21 | Theravance Inc | Aryl aniline beta2 adrenergic receptor agonists |
| TW200526547A (en) * | 2003-09-22 | 2005-08-16 | Theravance Inc | Amino-substituted ethylamino β2 adrenergic receptor agonists |
| TW200531692A (en) * | 2004-01-12 | 2005-10-01 | Theravance Inc | Aryl aniline derivatives as β2 adrenergic receptor agonists |
| EP1778638A1 (en) * | 2004-07-21 | 2007-05-02 | Theravance, Inc. | Diaryl ether beta2 adrenergic receptor agonists |
| EP1786762A2 (en) * | 2004-09-10 | 2007-05-23 | Theravance, Inc. | Amidine substituted aryl aniline compounds |
| EP1846374A1 (en) * | 2005-01-11 | 2007-10-24 | Glaxo Group Limited | Cinnamate salts of a beta-2 adrenergic agonist |
| ES2265276B1 (es) | 2005-05-20 | 2008-02-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
| BRPI0613034A8 (pt) | 2005-07-14 | 2018-01-02 | Lipothera Inc | formulação injetável para acúmulo de tecido adiposo, formulação injetável e método para o tratamento de acúmulo de gordura, e, método para reduzir o tecido adiposo. |
| RU2442771C2 (ru) | 2005-08-08 | 2012-02-20 | Арджента Дискавери Лтд | Производные бицикло[2,2,1]гепт-7-иламина и их применения |
| GB0516313D0 (en) | 2005-08-08 | 2005-09-14 | Argenta Discovery Ltd | Azole derivatives and their uses |
| TW200738658A (en) | 2005-08-09 | 2007-10-16 | Astrazeneca Ab | Novel compounds |
| US8653145B2 (en) * | 2005-09-22 | 2014-02-18 | Eaton Scientific Systems, Ltd. | Method for alleviating climacteric symptoms |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| TW200745067A (en) | 2006-03-14 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| MX2009004198A (es) * | 2006-10-17 | 2009-10-19 | Lithera Inc | Metodos, composiciones y formulaciones para el tratamiento de enfermedad ocular tiroidea. |
| ES2302447B1 (es) * | 2006-10-20 | 2009-06-12 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
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2005
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2007
- 2007-11-19 US US11/985,987 patent/US7662815B2/en active Active