JP2013526520A5 - - Google Patents
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- JP2013526520A5 JP2013526520A5 JP2013510204A JP2013510204A JP2013526520A5 JP 2013526520 A5 JP2013526520 A5 JP 2013526520A5 JP 2013510204 A JP2013510204 A JP 2013510204A JP 2013510204 A JP2013510204 A JP 2013510204A JP 2013526520 A5 JP2013526520 A5 JP 2013526520A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- amino
- phenyl
- oxo
- carboxamide
- 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.)
- Granted
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
- 150000003839 salts Chemical class 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- -1 R 8 -phenylene Chemical group 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 36
- 125000002947 alkylene group Chemical group 0.000 claims description 30
- 206010035664 Pneumonia Diseases 0.000 claims description 29
- 125000004450 alkenylene group Chemical group 0.000 claims description 28
- 125000004419 alkynylene group Chemical group 0.000 claims description 28
- 125000001475 halogen functional group Chemical group 0.000 claims description 28
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 201000009890 sinusitis Diseases 0.000 claims description 20
- 201000009267 bronchiectasis Diseases 0.000 claims description 19
- 125000002619 bicyclic group Chemical group 0.000 claims description 18
- 206010006451 bronchitis Diseases 0.000 claims description 18
- 125000006413 ring segment Chemical group 0.000 claims description 18
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 16
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 16
- 208000006673 asthma Diseases 0.000 claims description 16
- 241000282412 Homo Species 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 11
- 208000000884 Airway Obstruction Diseases 0.000 claims description 10
- 206010006448 Bronchiolitis Diseases 0.000 claims description 10
- 206010011224 Cough Diseases 0.000 claims description 10
- 206010014561 Emphysema Diseases 0.000 claims description 10
- 208000036142 Viral infection Diseases 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 230000002427 irreversible effect Effects 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 230000002441 reversible effect Effects 0.000 claims description 10
- 230000009385 viral infection Effects 0.000 claims description 10
- 206010006482 Bronchospasm Diseases 0.000 claims description 9
- 206010044314 Tracheobronchitis Diseases 0.000 claims description 9
- 230000007885 bronchoconstriction Effects 0.000 claims description 9
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 208000007451 chronic bronchitis Diseases 0.000 claims description 8
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 208000009470 Ventilator-Associated Pneumonia Diseases 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 238000002054 transplantation Methods 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000006585 (C6-C10) arylene group Chemical group 0.000 claims description 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 2
- BAZJZUZCSUFLIL-UMSFTDKQSA-N 6-[11-[[(2r)-2-hydroxy-2-(6-hydroxy-3-oxo-4h-1,4-benzoxazin-8-yl)ethyl]amino]undecylsulfonyl]-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)CCCCCCCCCCCNC[C@H](O)C=2C=3OCC(=O)NC=3C=C(O)C=2)=C1 BAZJZUZCSUFLIL-UMSFTDKQSA-N 0.000 claims description 2
- HPDPEZZBIDKKJM-DHUJRADRSA-N 6-[11-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]undecylsulfonyl]-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)CCCCCCCCCCCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=C1 HPDPEZZBIDKKJM-DHUJRADRSA-N 0.000 claims description 2
- QFXGDIPAWLICMO-FAIXQHPJSA-N 6-[3-[4-[6-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]hexyl]piperazine-1-carbonyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)N2CCN(CCCCCCNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)CC2)=C1 QFXGDIPAWLICMO-FAIXQHPJSA-N 0.000 claims description 2
- OTTAFDMNHGMXRG-DHUJRADRSA-N 6-[3-[4-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]piperidine-1-carbonyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)N2CCC(CC2)NC[C@H](O)C=2C=C(CO)C(O)=CC=2)=C1 OTTAFDMNHGMXRG-DHUJRADRSA-N 0.000 claims description 2
- KNUCTQUGSIOVHR-QNGWXLTQSA-N 6-[3-[4-[[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]methyl]phenyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C=2C=CC(CNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)=C1 KNUCTQUGSIOVHR-QNGWXLTQSA-N 0.000 claims description 2
- IEIIHNLKSIYDKJ-QNGWXLTQSA-N 6-[3-[6-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]hexyl-methylcarbamoyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)N(C)CCCCCCNC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=C1 IEIIHNLKSIYDKJ-QNGWXLTQSA-N 0.000 claims description 2
- DQLVYPNGWDAROB-BHVANESWSA-N 6-[3-[6-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]hexylcarbamoyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)NCCCCCCNC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=C1 DQLVYPNGWDAROB-BHVANESWSA-N 0.000 claims description 2
- AAWGNVDUCBOTMY-BHVANESWSA-N 6-[3-[6-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]hexylcarbamoyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)NCCCCCCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=C1 AAWGNVDUCBOTMY-BHVANESWSA-N 0.000 claims description 2
- UOTHKCMRNDDYRD-BHVANESWSA-N 6-[3-[6-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]hexylcarbamoyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)NCCCCCCNC[C@H](O)C=2C=C(CO)C(O)=CC=2)=C1 UOTHKCMRNDDYRD-BHVANESWSA-N 0.000 claims description 2
- OUMRTOZVILWOLR-BHVANESWSA-N 6-[3-[6-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(methanesulfonamido)phenyl]ethyl]amino]hexylcarbamoyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)NCCCCCCNC[C@H](O)C=2C=C(NS(C)(=O)=O)C(O)=CC=2)=C1 OUMRTOZVILWOLR-BHVANESWSA-N 0.000 claims description 2
- RHAQDHOXCGXPBG-LHEWISCISA-N 6-[3-[8-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]octylcarbamoyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)NCCCCCCCCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=C1 RHAQDHOXCGXPBG-LHEWISCISA-N 0.000 claims description 2
- BNFVCZHASQMFAV-RWYGWLOXSA-N 6-[3-[[4-[5-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]pent-1-ynyl]phenyl]carbamoyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)NC=2C=CC(=CC=2)C#CCCCNC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=C1 BNFVCZHASQMFAV-RWYGWLOXSA-N 0.000 claims description 2
- UZWQWAVCZAHYNC-RWYGWLOXSA-N 6-[3-[[4-[5-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]pentyl]phenyl]carbamoyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)NC=2C=CC(CCCCCNC[C@H](O)C=3C=C(CO)C(O)=CC=3)=CC=2)=C1 UZWQWAVCZAHYNC-RWYGWLOXSA-N 0.000 claims description 2
- MYHMQIPZHWFYJG-JEDAGLGPSA-N 6-[3-[[[3-[2-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]propyl]benzoyl]-methylamino]methyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(CN(C)C(=O)C=3C=C(CC(C)NC[C@H](O)C=4C=5C=CC(=O)NC=5C(O)=CC=4)C=CC=3)C=CC=2)=C1 MYHMQIPZHWFYJG-JEDAGLGPSA-N 0.000 claims description 2
- LRYCIMLJMXVFEK-QNGWXLTQSA-N 6-[4-[4-[[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]methyl]phenyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC(CNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)=C1 LRYCIMLJMXVFEK-QNGWXLTQSA-N 0.000 claims description 2
- UZVOGBFMUWRXRG-UHFFFAOYSA-N COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)N2CCN(CCNCC(O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)CC2)=C1 Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)N2CCN(CCNCC(O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)CC2)=C1 UZVOGBFMUWRXRG-UHFFFAOYSA-N 0.000 claims description 2
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 2
- 229940126033 PPAR agonist Drugs 0.000 claims description 2
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 230000001387 anti-histamine Effects 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 239000000739 antihistaminic agent Substances 0.000 claims description 2
- 229960005475 antiinfective agent Drugs 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims description 2
- 210000000621 bronchi Anatomy 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000000812 cholinergic antagonist Substances 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000002713 epithelial sodium channel blocking agent Substances 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 229940043355 kinase inhibitor Drugs 0.000 claims description 2
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 2
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- XDSPWYYVNKDCOQ-QLKFWGTOSA-N 6-[3-[5-[5-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]pentyl]-2,3-dihydroindole-1-carbonyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)N2C3=CC=C(CCCCCNC[C@H](O)C=4C=5C=CC(=O)NC=5C(O)=CC=4)C=C3CC2)=C1 XDSPWYYVNKDCOQ-QLKFWGTOSA-N 0.000 description 1
- SBQUNTRLQMQGSF-UHFFFAOYSA-N Cc(cc1)c(C=CC(N2)=O)c2c1O Chemical compound Cc(cc1)c(C=CC(N2)=O)c2c1O SBQUNTRLQMQGSF-UHFFFAOYSA-N 0.000 description 1
- NIKFEMWKHIGQQN-UHFFFAOYSA-N Cc1cc(O)cc(N2)c1C=CC2=O Chemical compound Cc1cc(O)cc(N2)c1C=CC2=O NIKFEMWKHIGQQN-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33302010P | 2010-05-10 | 2010-05-10 | |
| US61/333,020 | 2010-05-10 | ||
| US40693010P | 2010-10-26 | 2010-10-26 | |
| US61/406,930 | 2010-10-26 | ||
| US201161477263P | 2011-04-20 | 2011-04-20 | |
| US61/477,263 | 2011-04-20 | ||
| PCT/US2011/035738 WO2011143105A1 (en) | 2010-05-10 | 2011-05-09 | Bifunctional quinoline derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015045538A Division JP2015131833A (ja) | 2010-05-10 | 2015-03-09 | 二機能キノリン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013526520A JP2013526520A (ja) | 2013-06-24 |
| JP2013526520A5 true JP2013526520A5 (https=) | 2014-04-03 |
| JP5807058B2 JP5807058B2 (ja) | 2015-11-10 |
Family
ID=44072535
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013510204A Expired - Fee Related JP5807058B2 (ja) | 2010-05-10 | 2011-05-09 | 二機能キノリン誘導体 |
| JP2015045538A Pending JP2015131833A (ja) | 2010-05-10 | 2015-03-09 | 二機能キノリン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015045538A Pending JP2015131833A (ja) | 2010-05-10 | 2015-03-09 | 二機能キノリン誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8394829B2 (https=) |
| EP (1) | EP2569285A1 (https=) |
| JP (2) | JP5807058B2 (https=) |
| AR (1) | AR081026A1 (https=) |
| AU (1) | AU2011253203A1 (https=) |
| CA (1) | CA2796826A1 (https=) |
| NZ (1) | NZ603136A (https=) |
| UY (1) | UY33372A (https=) |
| WO (1) | WO2011143105A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2569285A1 (en) * | 2010-05-10 | 2013-03-20 | Gilead Sciences, Inc. | Bifunctional quinoline derivatives |
| CN105121439A (zh) | 2013-02-19 | 2015-12-02 | 辉瑞公司 | 作为pde4亚型抑制剂用于治疗cns和其他病症的氮杂苯并咪唑化合物 |
| EP3102569A1 (en) * | 2014-02-06 | 2016-12-14 | AbbVie Inc. | 6-heteroaryloxy- and 6-aryloxy-quinoline-2-carboxamides and uses thereof |
| JP6125467B2 (ja) * | 2014-06-16 | 2017-05-10 | 富士フイルム株式会社 | プリント注文受付機とその作動方法および作動プログラム |
| WO2016012896A1 (en) | 2014-07-24 | 2016-01-28 | Pfizer Inc. | Pyrazolopyrimidine compounds |
| PL3177624T3 (pl) | 2014-08-06 | 2019-09-30 | Pfizer Inc. | Związki imidazopirydazynowe |
| DK3236972T3 (en) | 2014-12-26 | 2021-10-04 | Univ Emory | Antivirale N4-hydroxycytidin-derivativer |
| CN106554350B (zh) * | 2015-09-29 | 2019-12-20 | 四川海思科制药有限公司 | 具有β2激动活性的苯并杂环衍生物及其制法和应用 |
| WO2017089347A1 (en) | 2015-11-25 | 2017-06-01 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods and pharmaceutical compositions for the treatment of braf inhibitor resistant melanomas |
| JP6804790B1 (ja) | 2017-12-07 | 2020-12-23 | エモリー ユニバーシティー | Ｎ４−ヒドロキシシチジンおよび誘導体ならびにそれらに関連する抗ウイルス用途 |
| CN112250557A (zh) * | 2020-10-23 | 2021-01-22 | 徐州工程学院 | 一种高效合成1,6-二烯-3-酮衍生物的方法 |
Family Cites Families (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3361306A (en) | 1966-03-31 | 1968-01-02 | Merck & Co Inc | Aerosol unit dispensing uniform amounts of a medically active ingredient |
| US3565070A (en) | 1969-02-28 | 1971-02-23 | Riker Laboratories Inc | Inhalation actuable aerosol dispenser |
| US3885047A (en) | 1972-06-16 | 1975-05-20 | Mead Johnson & Co | Ocular hypotensive process employing dextrorotatory phenethanolamines |
| US4145542A (en) | 1974-06-13 | 1979-03-20 | Otsuka Pharmaceutical Co., Ltd. | 5- 1-Hydroxy-2-(heterocyclic-amino)!alkyl-8-hydroxy-3,4-dihydrocarbostyril derivatives |
| ZW6584A1 (en) | 1983-04-18 | 1985-04-17 | Glaxo Group Ltd | Phenethanolamine derivatives |
| US4805811A (en) | 1985-03-29 | 1989-02-21 | Aktiebolaget Draco | Dosage device |
| US4761421A (en) | 1985-05-08 | 1988-08-02 | Merck & Co., Inc. | Use of certain compounds in livestock food as growth promotants for better feed utilization and improved carcass composition |
| US4955371A (en) | 1989-05-08 | 1990-09-11 | Transtech Scientific, Inc. | Disposable inhalation activated, aerosol device for pulmonary medicine |
| DE4003272A1 (de) | 1990-02-03 | 1991-08-08 | Boehringer Ingelheim Kg | Neue treibgasmischungen und ihre verwendung in arzneimittelzubereitungen |
| GB9107196D0 (en) | 1991-04-05 | 1991-05-22 | Sandoz Ag | Improvements in or relating to organic compounds |
| WO1993000951A1 (en) | 1991-07-02 | 1993-01-21 | Inhale, Inc. | Method and device for delivering aerosolized medicaments |
| US7105152B1 (en) | 1991-12-18 | 2006-09-12 | 3M Innovative Properties Company | Suspension aerosol formulations |
| EP0617610B1 (en) | 1991-12-18 | 1997-03-19 | Minnesota Mining And Manufacturing Company | Suspension aerosol formulations |
| US5261538A (en) | 1992-04-21 | 1993-11-16 | Glaxo Inc. | Aerosol testing method |
| US5455252A (en) | 1993-03-31 | 1995-10-03 | Syntex (U.S.A.) Inc. | Optionally substituted 6,8-quinolines |
| ES2176252T3 (es) | 1993-07-02 | 2002-12-01 | Altana Pharma Ag | Benzamidas sustituidas con fluoro-alcoxi y su utilizacion como agentes inhibidores de fosfodiesterasas de nucleotidos ciclicos. |
| US5776983A (en) | 1993-12-21 | 1998-07-07 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| US5522385A (en) | 1994-09-27 | 1996-06-04 | Aradigm Corporation | Dynamic particle size control for aerosolized drug delivery |
| US5622163A (en) | 1994-11-29 | 1997-04-22 | Iep Group, Inc. | Counter for fluid dispensers |
| US5544647A (en) | 1994-11-29 | 1996-08-13 | Iep Group, Inc. | Metered dose inhalator |
| MX9707862A (es) | 1995-04-14 | 1997-11-29 | Glaxo Wellcome Inc | Inhalador de dosis medida para el propionato de fluticasona. |
| AU5772196A (en) | 1995-05-19 | 1996-11-29 | Chiroscience Limited | 3,4-disubstituted-phenylsulphonamides and their therapeutic use |
| GB9523267D0 (en) | 1995-11-14 | 1996-01-17 | Sandoz Ltd | Organic compounds |
| EP0912519A1 (en) | 1996-05-20 | 1999-05-06 | Darwin Discovery Limited | Quinoline sulfonamides as tnf inhibitors and as pde-iv inhibitors |
| EP0952832B1 (en) | 1996-05-20 | 2008-08-27 | Darwin Discovery Limited | Quinoline carboxamides as tnf inhibitors and as pde-iv inhibitors |
| GB9712761D0 (en) | 1997-06-17 | 1997-08-20 | Chiroscience Ltd | Quinolines and their therapeutic use |
| US6069151A (en) | 1996-11-06 | 2000-05-30 | Darwin Discovery, Ltd. | Quinolines and their therapeutic use |
| US20010031244A1 (en) | 1997-06-13 | 2001-10-18 | Chiesi Farmaceutici S.P.A. | Pharmaceutical aerosol composition |
| GB9807232D0 (en) | 1998-04-03 | 1998-06-03 | Univ Cardiff | Aerosol composition |
| JP2002523452A (ja) | 1998-08-26 | 2002-07-30 | スミスクライン・ビーチャム・コーポレイション | 肺疾患の治療方法 |
| US6262070B1 (en) | 1998-11-04 | 2001-07-17 | Darwin Discovery Ltd. | Heterocyclic compounds and their therapeutic use |
| US6329034B1 (en) | 1999-01-18 | 2001-12-11 | Roger L. Pendry | Label having tab member and methods for forming, applying and using the same |
| US6116234A (en) | 1999-02-01 | 2000-09-12 | Iep Pharmaceutical Devices Inc. | Metered dose inhaler agitator |
| MXPA01012533A (es) | 1999-06-05 | 2003-10-14 | Innovata Biomed Ltd | Sistema de suministro. |
| GB2353222B (en) | 1999-06-23 | 2001-09-19 | Cambridge Consultants | Inhalers |
| EP1212089B1 (en) | 1999-08-21 | 2006-03-22 | ALTANA Pharma AG | Synergistic combination of roflumilast and salmeterol |
| GB9920839D0 (en) | 1999-09-04 | 1999-11-10 | Innovata Biomed Ltd | Inhaler |
| AU1068401A (en) | 1999-10-12 | 2001-04-23 | Shl Medical Ab | Inhaler |
| GB9928265D0 (en) | 1999-12-01 | 2000-01-26 | Innovata Biomed Ltd | Inhaler |
| AU8030500A (en) | 1999-12-08 | 2001-06-18 | Qualcomm Incorporated | Monitoring user interaction with web advertisements |
| SE9904706D0 (sv) | 1999-12-21 | 1999-12-21 | Astra Ab | An inhalation device |
| US6410563B1 (en) | 1999-12-22 | 2002-06-25 | Merck Frosst Canada & Co. | Substituted 8-arylquinoline phosphodiesterase-4 inhibitors |
| US7171965B2 (en) | 2000-02-01 | 2007-02-06 | Valois S.A.S. | Breath actuated dry powder inhaler and tape dose strip |
| NZ522882A (en) | 2000-06-05 | 2004-07-30 | Altana Pharma Bv | Pyridazinone compounds effective as beta-2-adrenoreceptor agonists as well as PDE4-inhibitors |
| FR2813593B1 (fr) | 2000-09-07 | 2002-12-06 | Valois Sa | Dispositif de distribution de produit fluide de type multidose |
| GB0026647D0 (en) | 2000-10-31 | 2000-12-13 | Glaxo Group Ltd | Medicament dispenser |
| US6740666B2 (en) | 2000-12-20 | 2004-05-25 | Merck & Co., Inc. | Substituted 8-arylquinoline phosphodiesterase-4 inhibitors |
| EP1404330B1 (en) | 2001-06-27 | 2005-06-01 | Merck Frosst Canada & Co. | Substituted 8-arylquinoline pde4 inhibitors |
| US6858615B2 (en) | 2002-02-19 | 2005-02-22 | Parion Sciences, Inc. | Phenyl guanidine sodium channel blockers |
| US7144896B2 (en) | 2002-03-18 | 2006-12-05 | Merck Frosst Canada Ltd. | Hetero-bridge substituted 8-arylquinoline pde4 inhibitors |
| US6889690B2 (en) | 2002-05-10 | 2005-05-10 | Oriel Therapeutics, Inc. | Dry powder inhalers, related blister devices, and associated methods of dispensing dry powder substances and fabricating blister packages |
| EP1507754A1 (en) * | 2002-05-28 | 2005-02-23 | Theravance, Inc. | Alkoxy aryl beta-2 adrenergic receptor agonists |
| EP1517895B1 (en) | 2002-06-25 | 2007-03-14 | Merck Frosst Canada Ltd. | 8-(biaryl) quinoline pde4 inhibitors |
| AU2003286024A1 (en) | 2002-11-22 | 2004-06-18 | Daniel Dube | Use of phosphodiesterase-4 inhibitors as enhancers of cognition |
| US6903105B2 (en) | 2003-02-19 | 2005-06-07 | Parion Sciences, Inc. | Sodium channel blockers |
| JP2006524638A (ja) | 2003-04-30 | 2006-11-02 | メルク フロスト カナダ リミテツド | ８−（３−ビアリール）フェニルキノリン系ホスホジエステラーゼ−４阻害薬 |
| TWI328009B (en) | 2003-05-21 | 2010-08-01 | Glaxo Group Ltd | Quinoline derivatives as phosphodiesterase inhibitors |
| EP1488819A1 (en) | 2003-06-16 | 2004-12-22 | Rijksuniversiteit te Groningen | Dry powder inhaler and method for pulmonary inhalation of dry powder |
| ES2432529T3 (es) | 2003-08-18 | 2013-12-04 | Parion Sciences, Inc. | Bloqueadores del canal de sodio de pirazinoilguanidina rematada |
| GB0322722D0 (en) | 2003-09-27 | 2003-10-29 | Glaxo Group Ltd | Compounds |
| GB0322726D0 (en) | 2003-09-27 | 2003-10-29 | Glaxo Group Ltd | Compounds |
| US7569586B2 (en) | 2004-08-16 | 2009-08-04 | Theravance, Inc. | Compounds having β2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
| US7399766B2 (en) | 2004-08-18 | 2008-07-15 | Parion Sciences, Inc. | Soluble amide & ester pyrazinoylguanidine sodium channel blockers |
| GB0503955D0 (en) | 2005-02-25 | 2005-04-06 | Glaxo Group Ltd | Novel compounds |
| CN101198313A (zh) * | 2005-08-01 | 2008-06-11 | 奇斯药制品公司 | 通过喷雾施用的包含长效β2－激动剂的药物制剂 |
| US7807834B2 (en) | 2005-08-03 | 2010-10-05 | Parion Sciences, Inc. | Capped pyrazinoylguanidine sodium channel blockers |
| US20100004215A1 (en) | 2005-10-19 | 2010-01-07 | Abhijit Ray | Compositions of phosphodiesterase type iv inhibitors |
| KR101501780B1 (ko) | 2006-01-24 | 2015-03-16 | 넥스바이오, 인코퍼레이티드 | 고분자 미소 구체들의 조제를 위한 기술 |
| JP2009118740A (ja) | 2006-03-03 | 2009-06-04 | Ajinomoto Co Inc | Ｌ−アミノ酸の製造法 |
| GB0605462D0 (en) | 2006-03-17 | 2006-04-26 | Glaxo Group Ltd | Novel compounds |
| RS20080411A (sr) * | 2006-03-20 | 2009-07-15 | Pfizer Limited, | Derivati amina |
| PL2035004T3 (pl) | 2006-06-09 | 2013-01-31 | Parion Sciences Inc | Podstawione fenylem pirazynoiloguanidynowe blokery kanału sodowego o aktywności beta-agonistycznej |
| EP2037924A2 (en) | 2006-07-07 | 2009-03-25 | Steven P. Govek | Bicyclic heteroaryl inhibitors of pde4 |
| JP2010534563A (ja) | 2007-07-24 | 2010-11-11 | ネクスバイオ，インク． | マイクロ粒子の作製のための技術 |
| WO2009100169A1 (en) | 2008-02-06 | 2009-08-13 | Glaxo Group Limited | Dual pharmacophores - pde4-muscarinic antagonistics |
| WO2009142589A1 (en) | 2008-05-20 | 2009-11-26 | Astrazeneca Ab | Combination of (a) glucocorticoid receptor modulator and (b) a muscarinic antagonist |
| US8263623B2 (en) * | 2008-07-11 | 2012-09-11 | Pfizer Inc. | Triazol derivatives useful for the treatment of diseases |
| WO2010015792A1 (en) * | 2008-08-06 | 2010-02-11 | Argenta Discovery Limited | Nitrogen containing heterocyclic compounds useful as bifunctional modulators of m3 receptors and beta-2 receptors |
| UY32521A (es) | 2009-04-03 | 2010-10-29 | Astrazeneca Ab | Combinación para emplear en el tratamiento de enfermedades respiratorias |
| US8367829B2 (en) | 2010-05-10 | 2013-02-05 | Gilead Sciences, Inc. | Bi-functional pyrazolopyridine compounds |
| EP2569285A1 (en) * | 2010-05-10 | 2013-03-20 | Gilead Sciences, Inc. | Bifunctional quinoline derivatives |
-
2011
- 2011-05-09 EP EP11719748A patent/EP2569285A1/en not_active Withdrawn
- 2011-05-09 CA CA2796826A patent/CA2796826A1/en not_active Abandoned
- 2011-05-09 NZ NZ603136A patent/NZ603136A/en not_active IP Right Cessation
- 2011-05-09 AU AU2011253203A patent/AU2011253203A1/en not_active Abandoned
- 2011-05-09 US US13/103,577 patent/US8394829B2/en not_active Expired - Fee Related
- 2011-05-09 UY UY0001033372A patent/UY33372A/es not_active Application Discontinuation
- 2011-05-09 WO PCT/US2011/035738 patent/WO2011143105A1/en not_active Ceased
- 2011-05-09 AR ARP110101593A patent/AR081026A1/es unknown
- 2011-05-09 JP JP2013510204A patent/JP5807058B2/ja not_active Expired - Fee Related
-
2012
- 2012-09-14 US US13/619,636 patent/US20130012504A1/en not_active Abandoned
-
2015
- 2015-03-09 JP JP2015045538A patent/JP2015131833A/ja active Pending
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