JP2008507532A5 - - Google Patents
Download PDFInfo
- Publication number
- 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- Withdrawn
Links
- 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 (https=) | 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 (https=) |
| EP (1) | EP1778638A1 (https=) |
| JP (1) | JP2008507532A (https=) |
| WO (1) | WO2006014704A1 (https=) |
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 |
| WO2006014704A1 (en) * | 2004-07-21 | 2006-02-09 | Theravance, Inc. | DIARYL ETHER β2 ADRENERGIC RECEPTOR AGONISTS |
| EP1786762A2 (en) * | 2004-09-10 | 2007-05-23 | Theravance, Inc. | Amidine substituted aryl aniline compounds |
| AU2006205933A1 (en) * | 2005-01-11 | 2006-07-20 | 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. |
| JP4778053B2 (ja) | 2005-07-14 | 2011-09-21 | リセラ，インコーポレイテッド | 局所的脂肪組織処置のための徐放性増強脂肪分解処方物 |
| GB0516313D0 (en) | 2005-08-08 | 2005-09-14 | Argenta Discovery Ltd | Azole derivatives and their uses |
| BRPI0614290A2 (pt) | 2005-08-08 | 2011-03-22 | Argenta Discovery Ltd | derivados de biciclo [ 2.2.1 ] hept-7-ilamina e seus usos |
| 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 |
| PL2077830T3 (pl) * | 2006-10-17 | 2013-04-30 | Lithera Inc | Sposoby, kompozycje i formulacje do leczenia orbitopatii tarczycowej |
| 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. |
| TW200833670A (en) | 2006-12-20 | 2008-08-16 | Astrazeneca Ab | Novel compounds 569 |
| GB0702458D0 (en) | 2007-02-08 | 2007-03-21 | Astrazeneca Ab | Salts 668 |
| ES2306595B1 (es) | 2007-02-09 | 2009-09-11 | Laboratorios Almirall S.A. | Sal de napadisilato de 5-(2-((6-(2,2-difluoro-2-feniletoxi)hexil)amino)-1-hidroxietil)-8-hidroxiquinolin-2(1h)-ona como agonista del receptor adrenergico beta2. |
| ES2320961B1 (es) | 2007-11-28 | 2010-03-17 | Laboratorios Almirall, S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor adrenergico beta2. |
| MX2010007604A (es) | 2008-01-11 | 2010-08-02 | Novartis Ag | Pirimidinas como inhibidores de cinasa. |
| EP2096105A1 (en) * | 2008-02-28 | 2009-09-02 | Laboratorios Almirall, S.A. | Derivatives of 4-(2-amino-1-hydroxyethyl)phenol as agonists of the b2 adrenergic receptor |
| WO2009154557A1 (en) | 2008-06-18 | 2009-12-23 | Astrazeneca Ab | Benzoxazinone derivatives acting as beta2-adrenoreceptor agonist for the treatment of respiratory disorders |
| US8236786B2 (en) | 2008-08-07 | 2012-08-07 | Pulmagen Therapeutics (Inflammation) Limited | Respiratory disease treatment |
| UY32297A (es) | 2008-12-22 | 2010-05-31 | Almirall Sa | Sal mesilato de 5-(2-{[6-(2,2-difluoro-2-fenilitoxi) hexil]amino}-1-hidroxietil)-8-hidroxiquinolin-2( 1h)-ona como agonista del receptor b(beta)2 acrenérgico |
| ES2442343T3 (es) | 2008-12-30 | 2014-02-11 | Pulmagen Therapeutics (Inflammation) Limited | Compuestos de sulfonamida para el tratamiento de trastornos respiratorios |
| EP2228368A1 (en) | 2009-03-12 | 2010-09-15 | Almirall, S.A. | Process for manufacturing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one |
| US9132084B2 (en) | 2009-05-27 | 2015-09-15 | Neothetics, Inc. | Methods for administration and formulations for the treatment of regional adipose tissue |
| WO2010150014A1 (en) | 2009-06-24 | 2010-12-29 | Pulmagen Therapeutics (Inflammation) Limited | 5r- 5 -deuterated glitazones for respiratory disease treatment |
| GB0918924D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Azaindole derivatives |
| GB0918923D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Aminothiazole derivatives |
| GB0918922D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Aminopyridine derivatives |
| GB2487868B (en) * | 2010-01-15 | 2014-12-10 | Neothetics Inc | Lyophilized cake formulations |
| WO2011098746A1 (en) | 2010-02-09 | 2011-08-18 | Pulmagen Therapeutics (Inflammation) Limited | Crystalline acid addition salts of ( 5r) -enanti0mer of pioglitazone |
| GB201002224D0 (en) | 2010-02-10 | 2010-03-31 | Argenta Therapeutics Ltd | Respiratory disease treatment |
| GB201002243D0 (en) | 2010-02-10 | 2010-03-31 | Argenta Therapeutics Ltd | Respiratory disease treatment |
| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| US8637516B2 (en) | 2010-09-09 | 2014-01-28 | Irm Llc | Compounds and compositions as TRK inhibitors |
| US9597531B2 (en) | 2010-11-24 | 2017-03-21 | Neothetics, Inc. | Selective, lipophilic, and long-acting beta agonist monotherapeutic formulations and methods for the cosmetic treatment of adiposity and contour bulging |
| WO2012116217A1 (en) | 2011-02-25 | 2012-08-30 | Irm Llc | Compounds and compositions as trk inhibitors |
| JO3192B1 (ar) | 2011-09-06 | 2018-03-08 | Novartis Ag | مركب بنزوثيازولون |
| EP2578570A1 (en) | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
| EP2641900A1 (en) | 2012-03-20 | 2013-09-25 | Almirall, S.A. | Novel polymorphic Crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one, heminapadisylate as agonist of the ß2 adrenergic receptor. |
| EP2647627A1 (en) * | 2012-04-02 | 2013-10-09 | Almirall, S.A. | Salts of 5-[(1r)-2-({2-[4-(2,2-difluoro-2-phenylethoxy)phenyl] ethyl}amino)-1-hydroxyethyl]-8-hydroxyquinolin-2(1h)-one. |
| CN106795366B (zh) * | 2014-07-02 | 2019-05-07 | 株式会社钟化 | 固化性组合物及其固化物 |
| WO2016027283A2 (en) * | 2014-08-22 | 2016-02-25 | Reddy G Pratap | A process for preparing indacaterol and salts thereof |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2266497B1 (https=) | 1974-04-03 | 1977-11-04 | Roussel Uclaf | |
| ZW6584A1 (en) * | 1983-04-18 | 1985-04-17 | Glaxo Group Ltd | Phenethanolamine derivatives |
| CA1262729A (en) * | 1983-10-19 | 1989-11-07 | Leo Alig | Phenoxypropanolamines |
| GB8334494D0 (en) | 1983-12-24 | 1984-02-01 | Tanabe Seiyaku Co | Carbostyril derivatives |
| US4894219A (en) * | 1988-03-29 | 1990-01-16 | University Of Florida | Beta-agonist carbostyril derivatives, assay method and pharmacological composition |
| ZA967892B (en) * | 1995-09-21 | 1998-03-18 | Lilly Co Eli | Selective β3 adrenergic agonists. |
| AU9462198A (en) * | 1997-10-17 | 1999-05-10 | Yamanouchi Pharmaceutical Co., Ltd. | Amide derivatives or salts thereof |
| US6541669B1 (en) * | 1998-06-08 | 2003-04-01 | Theravance, Inc. | β2-adrenergic receptor agonists |
| US6436914B1 (en) * | 1998-06-30 | 2002-08-20 | Bristol-Myers Squibb Company | 2-hydroxy-3—(4-hydroxy-3-sulfonamidophenyl)—propylamines useful as beta 3 adrenergic agonists |
| AUPP796798A0 (en) | 1998-12-30 | 1999-01-28 | Fujisawa Pharmaceutical Co., Ltd. | New compound |
| US20020143034A1 (en) * | 1998-12-30 | 2002-10-03 | Fujisawa Pharmaceutical Co. Ltd. | Aminoalcohol derivatives and their use as beta 3 adrenergic agonists |
| WO2001007026A2 (en) | 1999-07-22 | 2001-02-01 | Eli Lilly And Company | Improved method of treating type ii diabetes and obesity |
| CA2391654A1 (en) | 1999-11-15 | 2001-05-25 | Eli Lilly And Company | Aryloxy propanolamines for improving livestock production |
| WO2001035947A2 (en) | 1999-11-15 | 2001-05-25 | Eli Lilly And Company | Treating wasting syndromes with aryloxy propanolamines |
| OA11558A (en) | 1999-12-08 | 2004-06-03 | Advanced Medicine Inc | Beta 2-adrenergic receptor agonists. |
| UA73965C2 (en) * | 1999-12-08 | 2005-10-17 | Theravance Inc | b2 ADRENERGIC RECEPTOR ANTAGONISTS |
| BR0110331A (pt) * | 2000-04-27 | 2003-01-07 | Boehringer Ingelheim Pharma | Substâncias que mimetizam beta que têm uma atividade de longa duração, processos para prepará-las e o uso das mesmas como medicamentos |
| AUPQ841300A0 (en) | 2000-06-27 | 2000-07-20 | Fujisawa Pharmaceutical Co., Ltd. | New aminoalcohol derivatives |
| ES2398097T3 (es) | 2000-07-13 | 2013-03-13 | Eli Lilly And Company | Agonistas adrenérgicos beta3 |
| EP1341759B1 (en) | 2000-11-10 | 2006-06-14 | Eli Lilly And Company | 3-substituted oxindole beta 3 agonists |
| EP1366025B1 (en) * | 2001-03-08 | 2007-06-27 | Glaxo Group Limited | Agonists of beta-adrenoreceptors |
| DE10293174D2 (de) * | 2001-07-19 | 2004-07-01 | Luk Lamellen & Kupplungsbau | Übertragungsstrecke zum Ansteuern einer Kupplung |
| ES2438985T3 (es) | 2001-09-14 | 2014-01-21 | Glaxo Group Limited | Formulación de inhalación que comprende derivados de fenetanolamina para el tratamiento de enfermedades respiratorias |
| TWI249515B (en) * | 2001-11-13 | 2006-02-21 | Theravance Inc | Aryl aniline beta2 adrenergic receptor agonists |
| US6653323B2 (en) * | 2001-11-13 | 2003-11-25 | Theravance, Inc. | Aryl aniline β2 adrenergic receptor agonists |
| US20030229058A1 (en) * | 2001-11-13 | 2003-12-11 | Moran Edmund J. | Aryl aniline beta2 adrenergic receptor agonists |
| JP3852708B2 (ja) | 2002-06-27 | 2006-12-06 | アステラス製薬株式会社 | アミノアルコール誘導体 |
| GB0217225D0 (en) | 2002-07-25 | 2002-09-04 | Glaxo Group Ltd | Medicinal compounds |
| PE20050130A1 (es) * | 2002-08-09 | 2005-03-29 | Novartis Ag | Compuestos organicos |
| 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 |
| BRPI0511695A (pt) | 2004-06-03 | 2008-01-08 | Theravance Inc | agonistas de receptor (beta)2 adrenérgico diamina |
| WO2006014704A1 (en) * | 2004-07-21 | 2006-02-09 | Theravance, Inc. | DIARYL ETHER β2 ADRENERGIC RECEPTOR AGONISTS |
-
2005
- 2005-07-20 WO PCT/US2005/025690 patent/WO2006014704A1/en not_active Ceased
- 2005-07-20 JP JP2007522685A patent/JP2008507532A/ja not_active Withdrawn
- 2005-07-20 US US11/185,295 patent/US7317023B2/en not_active Expired - Lifetime
- 2005-07-20 EP EP05779346A patent/EP1778638A1/en not_active Withdrawn
-
2007
- 2007-11-19 US US11/985,987 patent/US7662815B2/en not_active Expired - Lifetime