CA2796826A1 - Bifunctional quinoline derivatives - Google Patents
Bifunctional quinoline derivatives Download PDFInfo
- Publication number
- CA2796826A1 CA2796826A1 CA2796826A CA2796826A CA2796826A1 CA 2796826 A1 CA2796826 A1 CA 2796826A1 CA 2796826 A CA2796826 A CA 2796826A CA 2796826 A CA2796826 A CA 2796826A CA 2796826 A1 CA2796826 A1 CA 2796826A1
- Authority
- CA
- Canada
- 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.)
- Abandoned
Links
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- 230000001588 bifunctional effect Effects 0.000 title 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 34
- 206010035664 Pneumonia Diseases 0.000 claims abstract 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 13
- 238000000034 method Methods 0.000 claims abstract 12
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 10
- 239000000203 mixture Substances 0.000 claims abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 6
- 206010006482 Bronchospasm Diseases 0.000 claims abstract 5
- 230000007885 bronchoconstriction Effects 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims 33
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 125000001475 halogen functional group Chemical group 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 12
- 125000006413 ring segment Chemical group 0.000 claims 10
- 201000003883 Cystic fibrosis Diseases 0.000 claims 8
- 201000009267 bronchiectasis Diseases 0.000 claims 8
- 206010006451 bronchitis Diseases 0.000 claims 8
- 201000009890 sinusitis Diseases 0.000 claims 8
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 6
- 208000006673 asthma Diseases 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 208000000884 Airway Obstruction Diseases 0.000 claims 4
- 206010006448 Bronchiolitis Diseases 0.000 claims 4
- 206010006458 Bronchitis chronic Diseases 0.000 claims 4
- 206010011224 Cough Diseases 0.000 claims 4
- 206010014561 Emphysema Diseases 0.000 claims 4
- 206010044314 Tracheobronchitis Diseases 0.000 claims 4
- 208000009470 Ventilator-Associated Pneumonia Diseases 0.000 claims 4
- 125000004450 alkenylene group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000004419 alkynylene group Chemical group 0.000 claims 4
- 208000007451 chronic bronchitis Diseases 0.000 claims 4
- 230000002427 irreversible effect Effects 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 230000002441 reversible effect Effects 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- -1 (R)-6-[[3-[[6-[[2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino] hexyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-carboxamide Chemical compound 0.000 claims 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 3
- HJBZAZITZDSWKD-RWYGWLOXSA-N 6-[3-[[4-[5-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]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=3C=CC(=O)NC=3C(O)=CC=2)=C1 HJBZAZITZDSWKD-RWYGWLOXSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 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 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000006585 (C6-C10) arylene group Chemical group 0.000 claims 1
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- LTKBBSNKJIAAPS-CWXYTELWSA-N 6-[3-[4-[3-[2-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]propyl]benzoyl]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(CC2)C(=O)C=2C=C(CC(C)NC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)C=CC=2)=C1 LTKBBSNKJIAAPS-CWXYTELWSA-N 0.000 claims 1
- IQKANIPRKUAYIX-KDXMTYKHSA-N 6-[3-[4-[5-[[(2r)-2-hydroxy-2-(5-hydroxy-3-oxo-4h-1,4-benzoxazin-8-yl)ethyl]amino]pentyl]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(CCCCCNC[C@H](O)C=3C=4OCC(=O)NC=4C(O)=CC=3)=CC=2)=C1 IQKANIPRKUAYIX-KDXMTYKHSA-N 0.000 claims 1
- ZKWWIMHQUIQBEL-RWYGWLOXSA-N 6-[3-[4-[6-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]hexoxy]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)OCCCCCCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=C1 ZKWWIMHQUIQBEL-RWYGWLOXSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 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 claims 1
- 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 1
- 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 1
- YPAKSYXPOCKTIM-DHUJRADRSA-N 6-[3-[6-[[(2r)-2-hydroxy-2-(5-hydroxy-3-oxo-4h-1,4-benzoxazin-8-yl)ethyl]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=3OCC(=O)NC=3C(O)=CC=2)=C1 YPAKSYXPOCKTIM-DHUJRADRSA-N 0.000 claims 1
- QHEGFUPFICUWLH-UMSFTDKQSA-N 6-[3-[6-[[(2r)-2-hydroxy-2-(5-hydroxy-3-oxo-4h-1,4-benzoxazin-8-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=3OCC(=O)NC=3C(O)=CC=2)=C1 QHEGFUPFICUWLH-UMSFTDKQSA-N 0.000 claims 1
- QSQQZINIKDYYPL-DHUJRADRSA-N 6-[3-[6-[[(2r)-2-hydroxy-2-(6-hydroxy-3-oxo-4h-1,4-benzoxazin-8-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=3OCC(=O)NC=3C=C(O)C=2)=C1 QSQQZINIKDYYPL-DHUJRADRSA-N 0.000 claims 1
- 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 1
- 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 1
- ZDFDVHNJXKVUAX-RWYGWLOXSA-N 6-[3-[[3-[5-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]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=C(C=CC=2)C#CCCCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=C1 ZDFDVHNJXKVUAX-RWYGWLOXSA-N 0.000 claims 1
- OKIPDLXQVHJCEV-SJARJILFSA-N 6-[3-[[4-[2-[6-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]hexoxy]ethyl]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(CCOCCCCCCNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)=C1 OKIPDLXQVHJCEV-SJARJILFSA-N 0.000 claims 1
- YANXZTLDJZIJCE-LHEWISCISA-N 6-[3-[[4-[2-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]ethyl]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(CCNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)=C1 YANXZTLDJZIJCE-LHEWISCISA-N 0.000 claims 1
- HUFHLGZXMJTLLA-DXQCBLCSSA-N 6-[3-[[4-[4-[6-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]hexoxy]butyl]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(CCCCOCCCCCCNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)=C1 HUFHLGZXMJTLLA-DXQCBLCSSA-N 0.000 claims 1
- WZESSWXGJWGUFT-QLKFWGTOSA-N 6-[3-[[4-[4-[[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]methyl]phenyl]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=2C=CC(CNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)=C1 WZESSWXGJWGUFT-QLKFWGTOSA-N 0.000 claims 1
- 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 1
- KJHIWVKNSQEKBZ-WBCKFURZSA-N 6-[3-[[4-[5-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]-methylamino]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#CCCCN(C)C[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=C1 KJHIWVKNSQEKBZ-WBCKFURZSA-N 0.000 claims 1
- HGMLAXYLPHPJPU-WBCKFURZSA-N 6-[3-[[4-[5-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]pent-1-ynyl]phenyl]-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)C=2C=CC(=CC=2)C#CCCCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=C1 HGMLAXYLPHPJPU-WBCKFURZSA-N 0.000 claims 1
- NVAIXOWXIOGRRQ-RWYGWLOXSA-N 6-[3-[[4-[5-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)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=4C=CC(=O)NC=4C(O)=CC=3)=CC=2)=C1 NVAIXOWXIOGRRQ-RWYGWLOXSA-N 0.000 claims 1
- 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 1
- LQGFARIRZVIMAL-WBCKFURZSA-N 6-[3-[[4-[6-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]hex-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#CCCCCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=C1 LQGFARIRZVIMAL-WBCKFURZSA-N 0.000 claims 1
- 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 1
- NKSGDKCFKVQWKQ-QNGWXLTQSA-N 6-[4-[4-[3-[[(2r)-2-hydroxy-2-(5-hydroxy-3-oxo-4h-1,4-benzoxazin-8-yl)ethyl]amino]propyl]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(CCCNC[C@H](O)C=3C=4OCC(=O)NC=4C(O)=CC=3)=CC=2)=C1 NKSGDKCFKVQWKQ-QNGWXLTQSA-N 0.000 claims 1
- DMARIDXGSAIIPJ-KDXMTYKHSA-N 6-[4-[4-[5-[[(2r)-2-hydroxy-2-(5-hydroxy-3-oxo-4h-1,4-benzoxazin-8-yl)ethyl]amino]pentyl]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(CCCCCNC[C@H](O)C=3C=4OCC(=O)NC=4C(O)=CC=3)=CC=2)=C1 DMARIDXGSAIIPJ-KDXMTYKHSA-N 0.000 claims 1
- 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 1
- FRIWAAALHURGFN-QNGWXLTQSA-N 6-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]hexyl n-[[3-[3-carbamoyl-4-(3-methoxyanilino)-8-methylquinolin-6-yl]sulfonylphenyl]methyl]carbamate Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(CNC(=O)OCCCCCCNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)C=CC=2)=C1 FRIWAAALHURGFN-QNGWXLTQSA-N 0.000 claims 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 1
- JLFGYGWNIKNTBF-UHFFFAOYSA-N OC(CNCCN1CCN(CC1)C(=O)C=1C=C(C=CC=1)S(=O)(=O)C=1C=C2C(=C(C=NC2=C(C=1)C)CC(=O)N)NC1=CC(=CC=C1)OC)C1=C2C=CC(NC2=C(C=C1)O)=O Chemical compound OC(CNCCN1CCN(CC1)C(=O)C=1C=C(C=CC=1)S(=O)(=O)C=1C=C2C(=C(C=NC2=C(C=1)C)CC(=O)N)NC1=CC(=CC=C1)OC)C1=C2C=CC(NC2=C(C=C1)O)=O JLFGYGWNIKNTBF-UHFFFAOYSA-N 0.000 claims 1
- YXNHHCXSSOWLFU-GWHBCOKCSA-N [3-[3-carbamoyl-4-(3-methoxyanilino)-8-methylquinolin-6-yl]sulfonylphenyl]methyl 4-[4-[4-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]butyl]phenyl]piperazine-1-carboxylate Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(COC(=O)N3CCN(CC3)C=3C=CC(CCCCNC[C@H](O)C=4C=5C=CC(=O)NC=5C(O)=CC=4)=CC=3)C=CC=2)=C1 YXNHHCXSSOWLFU-GWHBCOKCSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 229940125715 antihistaminic agent Drugs 0.000 claims 1
- 239000000739 antihistaminic agent Substances 0.000 claims 1
- 229960005475 antiinfective agent Drugs 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000002713 epithelial sodium channel blocking agent Substances 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 1
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2796826A1 true CA2796826A1 (en) | 2011-11-17 |
Family
ID=44072535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2796826A Abandoned CA2796826A1 (en) | 2010-05-10 | 2011-05-09 | Bifunctional quinoline derivatives |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8394829B2 (enExample) |
| EP (1) | EP2569285A1 (enExample) |
| JP (2) | JP5807058B2 (enExample) |
| AR (1) | AR081026A1 (enExample) |
| AU (1) | AU2011253203A1 (enExample) |
| CA (1) | CA2796826A1 (enExample) |
| NZ (1) | NZ603136A (enExample) |
| UY (1) | UY33372A (enExample) |
| WO (1) | WO2011143105A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ603136A (en) * | 2010-05-10 | 2014-11-28 | Gilead Sciences Inc | Bifunctional quinoline derivatives |
| AP2015008663A0 (en) | 2013-02-19 | 2015-08-31 | Pfizer | Azabenzimidazole compounds as inhibitors of PDE4 isozymes for the treatment of cns and other disorders |
| JP6532474B2 (ja) * | 2014-02-06 | 2019-06-19 | アッヴィ・インコーポレイテッド | ６−ヘテロアリールオキシ−および６−アリールオキシ−キノリン−２−カルボキシアミドならびにその使用 |
| 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 |
| EP3172210B1 (en) | 2014-07-24 | 2020-01-15 | Pfizer Inc | Pyrazolopyrimidine compounds |
| SG11201700243YA (en) | 2014-08-06 | 2017-02-27 | Pfizer | Imidazopyridazine compounds |
| IL296496B2 (en) | 2014-12-26 | 2024-10-01 | Univ Emory | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| 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 |
| KR102626210B1 (ko) | 2017-12-07 | 2024-01-18 | 에모리 유니버시티 | N4-하이드록시사이티딘 및 유도체 및 이와 관련된 항-바이러스 용도 |
| 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 |
| DK0617610T3 (da) | 1991-12-18 | 1997-10-06 | Minnesota Mining & Mfg | Suspensionsaerosolformuleringer. |
| 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 |
| DE59410119D1 (de) | 1993-07-02 | 2002-06-20 | Byk Gulden Lomberg Chem Fab | Fluoralkoxy substituierte benzamide und ihre verwendung als zyklisch-nukleotid phosphodiesterase-inhibitoren |
| 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 |
| US5544647A (en) | 1994-11-29 | 1996-08-13 | Iep Group, Inc. | Metered dose inhalator |
| US5622163A (en) | 1994-11-29 | 1997-04-22 | Iep Group, Inc. | Counter for fluid dispensers |
| BR9604978A (pt) | 1995-04-14 | 1998-06-09 | Glaxo Wellcome Inc | Inalador com dose medida |
| US5728712A (en) | 1995-05-19 | 1998-03-17 | Chiroscience Limited | 3,4-disubstituted-phenylsulphonamides and their therapeutic use |
| GB9523267D0 (en) | 1995-11-14 | 1996-01-17 | Sandoz Ltd | Organic compounds |
| WO1997044322A1 (en) | 1996-05-20 | 1997-11-27 | Darwin Discovery Limited | Quinoline sulfonamides as tnf inhibitors and as pde-iv inhibitors |
| NZ332341A (en) | 1996-05-20 | 2000-05-26 | Darwin Discovery Ltd | 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 |
| CZ293735B6 (cs) | 1998-08-26 | 2004-07-14 | Smithkline Beecham Corporation | Farmaceutický prostředek pro léčbu plicní nemoci |
| 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 |
| ATE294608T1 (de) | 1999-06-05 | 2005-05-15 | Innovata Biomed Ltd | Verabreichungsystem für medikamente |
| GB2353222B (en) | 1999-06-23 | 2001-09-19 | Cambridge Consultants | Inhalers |
| CA2715683A1 (en) | 1999-08-21 | 2001-03-01 | Nycomed Gmbh | Synergistic combination |
| GB9920839D0 (en) | 1999-09-04 | 1999-11-10 | Innovata Biomed Ltd | Inhaler |
| US6880555B1 (en) | 1999-10-12 | 2005-04-19 | 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 |
| CZ20023997A3 (cs) * | 2000-06-05 | 2003-05-14 | Altana Pharma Ag | Pyridazinonové deriváty |
| 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 |
| ATE296630T1 (de) | 2001-06-27 | 2005-06-15 | Merck Frosst Canada Inc | Substituierte 8-arylchinoline als pde4-hemmer |
| 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 |
| ATE356808T1 (de) | 2002-06-25 | 2007-04-15 | Merck Frosst Canada Ltd | 8-(biaryl)chinolin-pde4-inhibitoren |
| 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 |
| SI1663235T1 (sl) | 2003-08-18 | 2013-12-31 | Parion Sciences, Inc. | Zaščiteni pirazinoilgvanidinski blokatorji natrijevega kanala |
| GB0322722D0 (en) | 2003-09-27 | 2003-10-29 | Glaxo Group Ltd | Compounds |
| GB0322726D0 (en) | 2003-09-27 | 2003-10-29 | Glaxo Group Ltd | Compounds |
| WO2006023460A2 (en) | 2004-08-16 | 2006-03-02 | 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 |
| AU2006275137A1 (en) * | 2005-08-01 | 2007-02-08 | Chiesi Farmaceutici S.P.A. | Pharmaceutical formulations comprising a long-acting beta2-agonist for administration by nebulisation |
| 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 |
| EP1981483A1 (en) | 2006-01-24 | 2008-10-22 | Nexbio, Inc. | Technology for preparation of macromolecular microspheres |
| 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 |
| MX2008011963A (es) * | 2006-03-20 | 2008-10-01 | Pfizer Ltd | Derivados de amina. |
| PL2035004T3 (pl) | 2006-06-09 | 2013-01-31 | Parion Sciences Inc | Podstawione fenylem pirazynoiloguanidynowe blokery kanału sodowego o aktywności beta-agonistycznej |
| WO2008006050A2 (en) | 2006-07-07 | 2008-01-10 | Govek Steven P | Bicyclic heteroaryl inhibitors of pde4 |
| CN103784408A (zh) | 2007-07-24 | 2014-05-14 | 安迅生物制药公司 | 用于制备微粒的技术 |
| 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 |
| WO2011143106A1 (en) * | 2010-05-10 | 2011-11-17 | Gilead Sciences, Inc. | Bi - functional pyrazolopyridine compounds |
| NZ603136A (en) * | 2010-05-10 | 2014-11-28 | Gilead Sciences Inc | Bifunctional quinoline derivatives |
-
2011
- 2011-05-09 NZ NZ603136A patent/NZ603136A/en not_active IP Right Cessation
- 2011-05-09 CA CA2796826A patent/CA2796826A1/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 AR ARP110101593A patent/AR081026A1/es unknown
- 2011-05-09 WO PCT/US2011/035738 patent/WO2011143105A1/en not_active Ceased
- 2011-05-09 EP EP11719748A patent/EP2569285A1/en not_active Withdrawn
- 2011-05-09 AU AU2011253203A patent/AU2011253203A1/en not_active Abandoned
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| JP5807058B2 (ja) | 2015-11-10 |
| WO2011143105A1 (en) | 2011-11-17 |
| JP2013526520A (ja) | 2013-06-24 |
| EP2569285A1 (en) | 2013-03-20 |
| JP2015131833A (ja) | 2015-07-23 |
| UY33372A (es) | 2011-12-30 |
| NZ603136A (en) | 2014-11-28 |
| US20110275622A1 (en) | 2011-11-10 |
| AR081026A1 (es) | 2012-05-30 |
| AU2011253203A1 (en) | 2012-11-22 |
| US8394829B2 (en) | 2013-03-12 |
| US20130012504A1 (en) | 2013-01-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013526520A5 (enExample) | ||
| CO6310968A2 (es) | Derivados de 3,5-diamino sustituido-n-tetrahidropirimidin/imidazolin/diazepam-2-ilidenpirazin-2-carboxamida, utiles como bloqueadores de la actividad del canal de sodio epitelial (enac) | |
| RU2483072C2 (ru) | Производные фосфоновой кислоты и их применение в качестве антагонистов рецептора p2y12 | |
| JP2022548250A5 (enExample) | ||
| JP2014530900A5 (enExample) | ||
| JP2005509024A5 (enExample) | ||
| JP2014525426A5 (enExample) | ||
| RU2007132262A (ru) | Соединения и композиции в качестве ингибиторов протеинкиназ | |
| JP2022544714A5 (enExample) | ||
| RU2007101236A (ru) | Новые гидантоиновые производные для лечения обструктивных заболеваний дыхательных путей | |
| RU2016115803A (ru) | Замещенные никотинимидные ингибиторы втк, их получение и применение в терапии раковых, воспалительных и аутоиммунных заболеваний | |
| JP2014525937A5 (enExample) | ||
| JP2021514001A5 (enExample) | ||
| RU2009148673A (ru) | Производные пиразинона и их применение для лечения легочных заболеваний | |
| RU2004117887A (ru) | Ариланилиновые агонисты бета2 адренергических рецепторов | |
| JP2022504620A5 (enExample) | ||
| JP2014525427A5 (enExample) | ||
| JP2015514794A5 (enExample) | ||
| JP2016515606A (ja) | キナーゼ阻害剤として有用な尿素誘導体 | |
| KR20080094957A (ko) | 아민 유도체 | |
| JP2013503903A5 (enExample) | ||
| KR20110022611A (ko) | 베타２－아드레날린수용체 활성의 조절을 위한, ４－히드록시－２－옥소－２,３－디히드로－１,３－벤조티아졸－７－일 화합물을 포함하는 제약 조성물 | |
| EA025158B1 (ru) | Гетероциклические соединения, лекарственные средства, содержащие указанные соединения, их применение и способы их получения | |
| JP2015536974A5 (enExample) | ||
| EP2569285A1 (en) | Bifunctional quinoline derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140507 |
|
| FZDE | Discontinued |
Effective date: 20170109 |