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
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- 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)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Obesity (AREA)
- Communicable Diseases (AREA)
- Oncology (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 |
|---|---|---|---|---|
| CA2796826A1 (en) * | 2010-05-10 | 2011-11-17 | Gilead Sciences, Inc. | Bifunctional quinoline derivatives |
| EA201591360A1 (ru) | 2013-02-19 | 2016-03-31 | Пфайзер Инк. | Азабензимидазолы в качестве ингибиторов изозимов фдэ4 для лечения цнс и других расстройств |
| WO2015119998A1 (en) * | 2014-02-06 | 2015-08-13 | 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 |
| EP3172210B1 (en) | 2014-07-24 | 2020-01-15 | Pfizer Inc | Pyrazolopyrimidine compounds |
| AU2015298378B2 (en) | 2014-08-06 | 2018-08-02 | Pfizer Inc. | Imidazopyridazine compounds |
| CN118286245A (zh) | 2014-12-26 | 2024-07-05 | 埃莫里大学 | N4-羟基胞苷和衍生物及与其相关的抗病毒用途 |
| 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 |
| RS66222B1 (sr) | 2017-12-07 | 2024-12-31 | Univ Emory | N4-hidroksicitidin i derivati i antivirusne upotrebe povezane sa njim |
| 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 |
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-
2011
- 2011-05-09 CA CA2796826A patent/CA2796826A1/en not_active Abandoned
- 2011-05-09 AR ARP110101593A patent/AR081026A1/es unknown
- 2011-05-09 US US13/103,577 patent/US8394829B2/en not_active Expired - Fee Related
- 2011-05-09 JP JP2013510204A patent/JP5807058B2/ja not_active Expired - Fee Related
- 2011-05-09 EP EP11719748A patent/EP2569285A1/en not_active Withdrawn
- 2011-05-09 NZ NZ603136A patent/NZ603136A/en not_active IP Right Cessation
- 2011-05-09 WO PCT/US2011/035738 patent/WO2011143105A1/en not_active Ceased
- 2011-05-09 AU AU2011253203A patent/AU2011253203A1/en not_active Abandoned
- 2011-05-09 UY UY0001033372A patent/UY33372A/es not_active Application Discontinuation
-
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 |
| JP2015131833A (ja) | 2015-07-23 |
| NZ603136A (en) | 2014-11-28 |
| JP2013526520A (ja) | 2013-06-24 |
| US20110275622A1 (en) | 2011-11-10 |
| EP2569285A1 (en) | 2013-03-20 |
| AU2011253203A1 (en) | 2012-11-22 |
| AR081026A1 (es) | 2012-05-30 |
| UY33372A (es) | 2011-12-30 |
| US8394829B2 (en) | 2013-03-12 |
| WO2011143105A1 (en) | 2011-11-17 |
| US20130012504A1 (en) | 2013-01-10 |
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| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20140507 |
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| FZDE | Discontinued |
Effective date: 20170109 |