CA2559203A1 - Composes convenant pour le traitement de maladies - Google Patents
Composes convenant pour le traitement de maladies Download PDFInfo
- Publication number
- CA2559203A1 CA2559203A1 CA002559203A CA2559203A CA2559203A1 CA 2559203 A1 CA2559203 A1 CA 2559203A1 CA 002559203 A CA002559203 A CA 002559203A CA 2559203 A CA2559203 A CA 2559203A CA 2559203 A1 CA2559203 A1 CA 2559203A1
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- phenyl
- ethyl
- hydroxymethyl
- amino
- 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
- 229940124748 beta 2 agonist Drugs 0.000 title description 10
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims abstract description 423
- 150000001875 compounds Chemical class 0.000 claims abstract description 386
- 238000000034 method Methods 0.000 claims abstract description 180
- 239000000203 mixture Substances 0.000 claims abstract description 137
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 35
- 201000010099 disease Diseases 0.000 claims abstract description 26
- 208000035475 disorder Diseases 0.000 claims abstract description 9
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 160
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 150
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 118
- 150000001412 amines Chemical class 0.000 claims description 98
- -1 N-[2-fluoro-5-(trifluoromethyl)benzyl]-3-[(2R)-2-({(2R)-2-hydroxy-2-[4-hydroxy-(hydroxymethyl)phenyl]ethyl}amino)propyl]benzamide Chemical compound 0.000 claims description 64
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 45
- 208000006673 asthma Diseases 0.000 claims description 41
- 239000000556 agonist Substances 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 29
- 206010006451 bronchitis Diseases 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 27
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 24
- 102000005962 receptors Human genes 0.000 claims description 23
- 108020003175 receptors Proteins 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 201000009267 bronchiectasis Diseases 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 229940079593 drug Drugs 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 15
- 239000005557 antagonist Substances 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 11
- 230000001404 mediated effect Effects 0.000 claims description 11
- 229940124597 therapeutic agent Drugs 0.000 claims description 11
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000012453 solvate Substances 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- 230000008506 pathogenesis Effects 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 201000010659 intrinsic asthma Diseases 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 6
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 6
- 206010006482 Bronchospasm Diseases 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 5
- 230000007885 bronchoconstriction Effects 0.000 claims description 5
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims description 4
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims description 4
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 4
- 206010014561 Emphysema Diseases 0.000 claims description 4
- 229940122694 Muscarinic M3 receptor antagonist Drugs 0.000 claims description 4
- 208000027771 Obstructive airways disease Diseases 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000812 cholinergic antagonist Substances 0.000 claims description 4
- 208000007451 chronic bronchitis Diseases 0.000 claims description 4
- 208000024711 extrinsic asthma Diseases 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229940043355 kinase inhibitor Drugs 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 239000003681 muscarinic M3 receptor antagonist Substances 0.000 claims description 4
- 230000000414 obstructive effect Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 4
- 229940044551 receptor antagonist Drugs 0.000 claims description 4
- 239000002464 receptor antagonist Substances 0.000 claims description 4
- 125000000565 sulfonamide group Chemical group 0.000 claims description 4
- FCPHJRLWZDAJBF-SANMLTNESA-N 2-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]phenyl]-n-[(2-methylsulfanylphenyl)methyl]acetamide Chemical compound CSC1=CC=CC=C1CNC(=O)CC1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=C(CO)C(O)=CC=2)=C1 FCPHJRLWZDAJBF-SANMLTNESA-N 0.000 claims description 3
- ZUBOJZNZOGLRLT-MHZLTWQESA-N 2-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]ethyl]phenyl]-n-(3-phenylpropyl)acetamide Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCC=2C=C(CC(=O)NCCCC=3C=CC=CC=3)C=CC=2)=C1 ZUBOJZNZOGLRLT-MHZLTWQESA-N 0.000 claims description 3
- GJYYZUNZPYBLAU-HRFSGMKKSA-N 3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]-n-(3-phenylpropyl)benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(CO)C(O)=CC=1)C(C=1)=CC=CC=1C(=O)NCCCC1=CC=CC=C1 GJYYZUNZPYBLAU-HRFSGMKKSA-N 0.000 claims description 3
- NQIIDCDWCCHNTB-OSPHWJPCSA-N 3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]-n-phenylbenzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(CO)C(O)=CC=1)C(C=1)=CC=CC=1C(=O)NC1=CC=CC=C1 NQIIDCDWCCHNTB-OSPHWJPCSA-N 0.000 claims description 3
- ZPPQHXIVILOCJF-PMERELPUSA-N 3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]-n-(2-naphthalen-2-ylethyl)benzamide Chemical compound C1([C@@H](O)CNC(C)(CC=2C=C(C=CC=2)C(=O)NCCC=2C=C3C=CC=CC3=CC=2)C)=CC=C(O)C(CO)=C1 ZPPQHXIVILOCJF-PMERELPUSA-N 0.000 claims description 3
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
- 108090000695 Cytokines Proteins 0.000 claims description 3
- 102000004127 Cytokines Human genes 0.000 claims description 3
- 208000000059 Dyspnea Diseases 0.000 claims description 3
- 206010013975 Dyspnoeas Diseases 0.000 claims description 3
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 3
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 3
- 101100545004 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YSP2 gene Proteins 0.000 claims description 3
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 3
- 102000000551 Syk Kinase Human genes 0.000 claims description 3
- 108010016672 Syk Kinase Proteins 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 239000002465 adenosine A2a receptor agonist Substances 0.000 claims description 3
- 239000013566 allergen Substances 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 claims description 3
- 230000000155 isotopic effect Effects 0.000 claims description 3
- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 claims description 3
- GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 claims description 3
- OTZRAYGBFWZKMX-JUDRUQEKSA-N leukotriene E4 Chemical compound CCCCCC=CCC=C\C=C\C=C\[C@@H](SC[C@H](N)C(O)=O)[C@@H](O)CCCC(O)=O OTZRAYGBFWZKMX-JUDRUQEKSA-N 0.000 claims description 3
- AKGAYMDCLUSCDA-QLYZNEQGSA-N n-(1-adamantyl)-2-[3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]phenyl]acetamide Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C(CC(=O)NC34CC5CC(CC(C5)C3)C4)C=CC=2)C)=CC=C(O)C(CO)=C1 AKGAYMDCLUSCDA-QLYZNEQGSA-N 0.000 claims description 3
- PNZQBIROPDWCJZ-GRBSEGRKSA-N n-(1-adamantylmethyl)-2-[3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]phenyl]acetamide Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C(CC(=O)NCC34CC5CC(CC(C5)C3)C4)C=CC=2)C)=CC=C(O)C(CO)=C1 PNZQBIROPDWCJZ-GRBSEGRKSA-N 0.000 claims description 3
- UDKRUUILMOKVIK-MHZLTWQESA-N n-(2,3-dihydro-1h-inden-2-yl)-2-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]ethyl]phenyl]acetamide Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCC=2C=C(CC(=O)NC3CC4=CC=CC=C4C3)C=CC=2)=C1 UDKRUUILMOKVIK-MHZLTWQESA-N 0.000 claims description 3
- YPAXWASYYBIKJZ-CLYVBNDRSA-N n-(2,3-dihydro-1h-inden-2-yl)-3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]benzamide Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C(C=CC=2)C(=O)NC2CC3=CC=CC=C3C2)C)=CC=C(O)C(CO)=C1 YPAXWASYYBIKJZ-CLYVBNDRSA-N 0.000 claims description 3
- ZQXBHDHFEVNRFK-QJWGWKRISA-N n-(5,6-diethyl-2,3-dihydro-1h-inden-2-yl)-3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]benzamide Chemical compound C1([C@@H](O)CN[C@H](C)CC=2C=CC=C(C=2)C(=O)NC2CC=3C=C(C(=CC=3C2)CC)CC)=CC=C(O)C(CO)=C1 ZQXBHDHFEVNRFK-QJWGWKRISA-N 0.000 claims description 3
- CYGNCYLPSZBGFX-OSPHWJPCSA-N n-(cyclobutylmethyl)-2-[3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]phenyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(CO)C(O)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1CCC1 CYGNCYLPSZBGFX-OSPHWJPCSA-N 0.000 claims description 3
- JJXUFDHQIOWCIN-HRFSGMKKSA-N n-(cycloheptylmethyl)-2-[3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]phenyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(CO)C(O)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1CCCCCC1 JJXUFDHQIOWCIN-HRFSGMKKSA-N 0.000 claims description 3
- MMBWTVISHPNRTJ-MHZLTWQESA-N n-(cycloheptylmethyl)-2-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]phenyl]acetamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1CCCCCC1 MMBWTVISHPNRTJ-MHZLTWQESA-N 0.000 claims description 3
- JQXXGJTUPRTBOU-JVAFGIKQSA-N n-[(1s)-1-cyclohexylethyl]-2-[3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]phenyl]acetamide Chemical compound C1([C@H](C)NC(=O)CC=2C=CC=C(C=2)C[C@@H](C)NC[C@H](O)C=2C=C(CO)C(O)=CC=2)CCCCC1 JQXXGJTUPRTBOU-JVAFGIKQSA-N 0.000 claims description 3
- AFIOFXCVSBSKLM-NDEPHWFRSA-N n-[(2,3-dimethylphenyl)methyl]-2-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]phenyl]acetamide Chemical compound CC1=CC=CC(CNC(=O)CC=2C=C(CC(C)(C)NC[C@H](O)C=3C=C(CO)C(O)=CC=3)C=CC=2)=C1C AFIOFXCVSBSKLM-NDEPHWFRSA-N 0.000 claims description 3
- DNVCSQNMHJUIKE-WINIVTDRSA-N n-[(2,3-dimethylphenyl)methyl]-3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(CO)C(O)=CC=1)C(C=1)=CC=CC=1C(=O)NCC1=CC=CC(C)=C1C DNVCSQNMHJUIKE-WINIVTDRSA-N 0.000 claims description 3
- ZIOSVVYISLVGFY-VWLOTQADSA-N n-[(2,6-dimethoxyphenyl)methyl]-2-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]ethyl]phenyl]acetamide Chemical compound COC1=CC=CC(OC)=C1CNC(=O)CC1=CC=CC(CCNC[C@H](O)C=2C=C(CO)C(O)=CC=2)=C1 ZIOSVVYISLVGFY-VWLOTQADSA-N 0.000 claims description 3
- GQNNVVBEBUYOCC-CJAUYULYSA-N n-[(2,6-dimethoxyphenyl)methyl]-3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]benzamide Chemical compound COC1=CC=CC(OC)=C1CNC(=O)C1=CC=CC(C[C@@H](C)NC[C@H](O)C=2C=C(CO)C(O)=CC=2)=C1 GQNNVVBEBUYOCC-CJAUYULYSA-N 0.000 claims description 3
- GNVLWQPRWDBHAM-NSYGIPOTSA-N n-[(4-chlorophenyl)methyl]-3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(CO)C(O)=CC=1)C(C=1)=CC=CC=1C(=O)NCC1=CC=C(Cl)C=C1 GNVLWQPRWDBHAM-NSYGIPOTSA-N 0.000 claims description 3
- CWAACZPVXVGKHR-SANMLTNESA-N n-[2-(2-chlorophenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=CC=C1Cl CWAACZPVXVGKHR-SANMLTNESA-N 0.000 claims description 3
- RDYLUGILNAARKF-SANMLTNESA-N n-[2-(3,4-dichlorophenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=C(Cl)C(Cl)=C1 RDYLUGILNAARKF-SANMLTNESA-N 0.000 claims description 3
- PKNXVXJXAHAMLG-SANMLTNESA-N n-[2-(4-chlorophenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=C(Cl)C=C1 PKNXVXJXAHAMLG-SANMLTNESA-N 0.000 claims description 3
- GUHCKFLYXCEWTE-NDEPHWFRSA-N n-[2-(4-chlorophenyl)ethyl]-n-ethyl-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C=1C=CC(CC(C)(C)NC[C@H](O)C=2C=C(CO)C(O)=CC=2)=CC=1C(=O)N(CC)CCC1=CC=C(Cl)C=C1 GUHCKFLYXCEWTE-NDEPHWFRSA-N 0.000 claims description 3
- VDXPMHIBENBYPX-SANMLTNESA-N n-[[3-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]phenyl]acetamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC(F)=CC(C(F)(F)F)=C1 VDXPMHIBENBYPX-SANMLTNESA-N 0.000 claims description 3
- ZBSVGVLDLFLNAE-MHZLTWQESA-N n-benzyl-2-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]phenyl]-n-methylacetamide Chemical compound C=1C=CC(CC(C)(C)NC[C@H](O)C=2C=C(CO)C(O)=CC=2)=CC=1CC(=O)N(C)CC1=CC=CC=C1 ZBSVGVLDLFLNAE-MHZLTWQESA-N 0.000 claims description 3
- RJMSFLODFKHYEI-SANMLTNESA-N n-benzyl-2-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]phenyl]acetamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=CC=C1 RJMSFLODFKHYEI-SANMLTNESA-N 0.000 claims description 3
- POSFHIVNIDUNQY-CJAUYULYSA-N n-benzyl-3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(CO)C(O)=CC=1)C(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1 POSFHIVNIDUNQY-CJAUYULYSA-N 0.000 claims description 3
- GEIDJLKNCBQHFI-MWTRTKDXSA-N n-cyclobutyl-2-[3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]phenyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(CO)C(O)=CC=1)C(C=1)=CC=CC=1CC(=O)NC1CCC1 GEIDJLKNCBQHFI-MWTRTKDXSA-N 0.000 claims description 3
- SETDBYMQDZOVOP-BCHFMIIMSA-N n-cycloheptyl-2-[3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]phenyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(CO)C(O)=CC=1)C(C=1)=CC=CC=1CC(=O)NC1CCCCCC1 SETDBYMQDZOVOP-BCHFMIIMSA-N 0.000 claims description 3
- LKGZTZVDZTUHRM-CJAUYULYSA-N n-cyclohexyl-2-[3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]phenyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(CO)C(O)=CC=1)C(C=1)=CC=CC=1CC(=O)NC1CCCCC1 LKGZTZVDZTUHRM-CJAUYULYSA-N 0.000 claims description 3
- ZFXPCRGTGFGHFD-OSPHWJPCSA-N n-cyclopentyl-2-[3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]phenyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(CO)C(O)=CC=1)C(C=1)=CC=CC=1CC(=O)NC1CCCC1 ZFXPCRGTGFGHFD-OSPHWJPCSA-N 0.000 claims description 3
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 3
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- MVRURRNRPLZDIK-SANMLTNESA-N n-[(2,6-dichlorophenyl)methyl]-2-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]phenyl]acetamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=C(Cl)C=CC=C1Cl MVRURRNRPLZDIK-SANMLTNESA-N 0.000 claims description 2
- FJICPAMLQXLHFW-VWLOTQADSA-N n-[(2-chlorophenyl)methyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1Cl FJICPAMLQXLHFW-VWLOTQADSA-N 0.000 claims description 2
- IDPYYGGCBMNXIA-SANMLTNESA-N n-[(3,4-dichlorophenyl)methyl]-2-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]phenyl]acetamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=C(Cl)C(Cl)=C1 IDPYYGGCBMNXIA-SANMLTNESA-N 0.000 claims description 2
- MZALAYJHTIRPMB-VWLOTQADSA-N n-[(3,4-dichlorophenyl)methyl]-2-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]ethyl]phenyl]acetamide Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCC=2C=C(CC(=O)NCC=3C=C(Cl)C(Cl)=CC=3)C=CC=2)=C1 MZALAYJHTIRPMB-VWLOTQADSA-N 0.000 claims description 2
- IVMBOTQYZSYTEI-CPJLOUKISA-N n-[(3,4-dichlorophenyl)methyl]-3-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(CO)C(O)=CC=1)C(C=1)=CC=CC=1C(=O)NCC1=CC=C(Cl)C(Cl)=C1 IVMBOTQYZSYTEI-CPJLOUKISA-N 0.000 claims description 2
- ROMBYVIMRWLLKH-MHZLTWQESA-N n-[(3,4-dichlorophenyl)methyl]-3-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]phenyl]propanamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CCC(=O)NCC1=CC=C(Cl)C(Cl)=C1 ROMBYVIMRWLLKH-MHZLTWQESA-N 0.000 claims description 2
- DRCSWVCVCPAIKZ-SANMLTNESA-N n-[(3,5-dichlorophenyl)methyl]-2-[3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]phenyl]acetamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC(Cl)=CC(Cl)=C1 DRCSWVCVCPAIKZ-SANMLTNESA-N 0.000 claims description 2
- DVDRGAAXAWZUPI-VWLOTQADSA-N n-[(3-chlorophenyl)methyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCC1=CC=CC(Cl)=C1 DVDRGAAXAWZUPI-VWLOTQADSA-N 0.000 claims description 2
- ABBSCQVNYNKCKM-DEOSSOPVSA-N n-[(4-chlorophenyl)methyl]-3-[2-[[(2r)-2-(3,4-dihydroxy-2-methylphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]benzamide Chemical compound CC1=C(O)C(O)=CC=C1[C@@H](O)CNC(C)(C)CC1=CC=CC(C(=O)NCC=2C=CC(Cl)=CC=2)=C1 ABBSCQVNYNKCKM-DEOSSOPVSA-N 0.000 claims description 2
- MDYITIGLWYBSBH-SANMLTNESA-N n-[2-(1h-benzimidazol-2-yl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C1([C@@H](O)CNC(C)(CC=2C=C(C=CC=2)C(=O)NCCC=2NC3=CC=CC=C3N=2)C)=CC=C(O)C(CO)=C1 MDYITIGLWYBSBH-SANMLTNESA-N 0.000 claims description 2
- CXWLRXJQFIATGO-VWLOTQADSA-N n-[2-(2,3-dichlorophenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=CC(Cl)=C1Cl CXWLRXJQFIATGO-VWLOTQADSA-N 0.000 claims description 2
- BXICLUZZMZQGCM-NDEPHWFRSA-N n-[2-(2,3-dimethylphenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound CC1=CC=CC(CCNC(=O)C=2C=C(CC(C)(C)NC[C@H](O)C=3C=C(CO)C(O)=CC=3)C=CC=2)=C1C BXICLUZZMZQGCM-NDEPHWFRSA-N 0.000 claims description 2
- KPPUJQHFYZOEGH-NDEPHWFRSA-N n-[2-(2,4-dimethylphenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound CC1=CC(C)=CC=C1CCNC(=O)C1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=C(CO)C(O)=CC=2)=C1 KPPUJQHFYZOEGH-NDEPHWFRSA-N 0.000 claims description 2
- SXSBACKBZBCSJP-SANMLTNESA-N n-[2-(2,6-dichlorophenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=C(Cl)C=CC=C1Cl SXSBACKBZBCSJP-SANMLTNESA-N 0.000 claims description 2
- ULUYDYMBCANPRB-NDEPHWFRSA-N n-[2-(2,6-dimethylphenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound CC1=CC=CC(C)=C1CCNC(=O)C1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=C(CO)C(O)=CC=2)=C1 ULUYDYMBCANPRB-NDEPHWFRSA-N 0.000 claims description 2
- RBKCFSPJOINSPU-SANMLTNESA-N n-[2-(2-chloro-4-fluorophenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=C(F)C=C1Cl RBKCFSPJOINSPU-SANMLTNESA-N 0.000 claims description 2
- CKMSDVHPMRVYQB-SANMLTNESA-N n-[2-(2-chloro-6-fluoro-3-methylphenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound CC1=CC=C(F)C(CCNC(=O)C=2C=C(CC(C)(C)NC[C@H](O)C=3C=C(CO)C(O)=CC=3)C=CC=2)=C1Cl CKMSDVHPMRVYQB-SANMLTNESA-N 0.000 claims description 2
- IFELYYYVEUCMJU-SANMLTNESA-N n-[2-(3,4-difluorophenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=C(F)C(F)=C1 IFELYYYVEUCMJU-SANMLTNESA-N 0.000 claims description 2
- FSGJVSXVMUBIMA-NDEPHWFRSA-N n-[2-(3,4-dimethylphenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C1=C(C)C(C)=CC=C1CCNC(=O)C1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=C(CO)C(O)=CC=2)=C1 FSGJVSXVMUBIMA-NDEPHWFRSA-N 0.000 claims description 2
- DFPWRNNRRMRDOV-SANMLTNESA-N n-[2-(3-fluorophenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=CC(F)=C1 DFPWRNNRRMRDOV-SANMLTNESA-N 0.000 claims description 2
- QVNLWOFHDTVWMQ-VWLOTQADSA-N n-[2-(4,6-dimethylpyrimidin-2-yl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound CC1=CC(C)=NC(CCNC(=O)C=2C=C(CC(C)(C)NC[C@H](O)C=3C=C(CO)C(O)=CC=3)C=CC=2)=N1 QVNLWOFHDTVWMQ-VWLOTQADSA-N 0.000 claims description 2
- GOLSHQBJZLCLCF-SANMLTNESA-N n-[2-(4-chloro-2-fluorophenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(CO)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=C(Cl)C=C1F GOLSHQBJZLCLCF-SANMLTNESA-N 0.000 claims description 2
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- AUTKKFHQUBFCSY-NDEPHWFRSA-N n-[2-(4-hydroxy-2,3-dimethylphenyl)ethyl]-3-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-2-methylpropyl]benzamide Chemical compound CC1=C(O)C=CC(CCNC(=O)C=2C=C(CC(C)(C)NC[C@H](O)C=3C=C(CO)C(O)=CC=3)C=CC=2)=C1C AUTKKFHQUBFCSY-NDEPHWFRSA-N 0.000 claims description 2
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- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229950004351 telenzepine Drugs 0.000 description 1
- KCICIERONJJKMJ-UHFFFAOYSA-N tert-butyl n-[1-(3-bromophenyl)-2-methylpropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(C)CC1=CC=CC(Br)=C1 KCICIERONJJKMJ-UHFFFAOYSA-N 0.000 description 1
- FZSSOIODHOHQQO-UHFFFAOYSA-N tert-butyl n-[3-(2-ethyl-2,3-dihydro-1-benzofuran-5-yl)propyl]-n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)CCCC1=CC=C2OC(CC)CC2=C1 FZSSOIODHOHQQO-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical class O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940074410 trehalose Drugs 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- FEVFLQDDNUQKRY-UHFFFAOYSA-N tris(4-methylphenyl) phosphite Chemical compound C1=CC(C)=CC=C1OP(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 FEVFLQDDNUQKRY-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 229950000339 xinafoate Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
- A61P11/06—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
- A61P11/16—Central respiratory analeptics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pulmonology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04290725.3 | 2004-03-17 | ||
| EP04290725A EP1577291A1 (fr) | 2004-03-17 | 2004-03-17 | Dérivés béta-2 agonistes de la phényléthanolamine |
| US59179004P | 2004-07-27 | 2004-07-27 | |
| US60/591,790 | 2004-07-27 | ||
| GB0425064A GB0425064D0 (en) | 2004-11-12 | 2004-11-12 | Compounds useful for the treatment of diseases |
| GB0425064.3 | 2004-11-12 | ||
| PCT/IB2005/000640 WO2005090287A2 (fr) | 2004-03-17 | 2005-03-10 | Composes convenant pour le traitement de maladies |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2559203A1 true CA2559203A1 (fr) | 2005-09-29 |
Family
ID=56290672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002559203A Abandoned CA2559203A1 (fr) | 2004-03-17 | 2005-03-10 | Composes convenant pour le traitement de maladies |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1727789A2 (fr) |
| JP (1) | JP4054366B2 (fr) |
| AU (1) | AU2005223488A1 (fr) |
| BR (1) | BRPI0508927A (fr) |
| CA (1) | CA2559203A1 (fr) |
| EA (1) | EA200601510A1 (fr) |
| WO (1) | WO2005090287A2 (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0425054D0 (en) * | 2004-03-23 | 2004-12-15 | Pfizer Ltd | Formamide derivatives for the treatment of diseases |
| UA87854C2 (en) | 2004-06-07 | 2009-08-25 | Мерк Энд Ко., Инк. | N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| ES2320961B1 (es) * | 2007-11-28 | 2010-03-17 | Laboratorios Almirall, S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor adrenergico beta2. |
| PL2231642T3 (pl) | 2008-01-11 | 2014-04-30 | Novartis Ag | Pirymidyny jako inhibitory kinazy |
| JP5801997B2 (ja) | 2009-07-07 | 2015-10-28 | ファイザー・リミテッドＰｆｉｚｅｒ Ｌｉｍｉｔｅｄ | 薬品の組合せを吸入するための投薬ユニット、投薬ユニットのパック、および吸入器 |
| US8637516B2 (en) | 2010-09-09 | 2014-01-28 | Irm Llc | Compounds and compositions as TRK inhibitors |
| WO2012034095A1 (fr) | 2010-09-09 | 2012-03-15 | Irm Llc | Composés et compositions comme inhibiteurs de trk |
| AU2012220572A1 (en) | 2011-02-25 | 2013-08-29 | Irm Llc | Compounds and compositions as trk inhibitors |
| CN116033893A (zh) | 2020-06-26 | 2023-04-28 | 迈兰制药英国有限公司 | 包含5-[3-(3-羟基苯氧基)氮杂环丁烷-1-基]-5-甲基-2,2-二苯基己酰胺的制剂 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1529972A (en) * | 1975-07-29 | 1978-10-25 | Allen & Hanburys Ltd | Basic alcohols |
| DE2965655D1 (en) * | 1978-06-28 | 1983-07-21 | Beecham Group Plc | Secondary amines, their preparation, pharmaceutical compositions containing them and their use |
| GR850936B (fr) * | 1984-04-17 | 1985-11-25 | Glaxo Group Ltd | |
| GB8528633D0 (en) * | 1985-11-21 | 1985-12-24 | Beecham Group Plc | Compounds |
| OA11558A (en) * | 1999-12-08 | 2004-06-03 | Advanced Medicine Inc | Beta 2-adrenergic receptor agonists. |
| WO2003042160A1 (fr) * | 2001-11-13 | 2003-05-22 | Theravance, Inc. | Agonistes de recepteur d'aryl aniline beta-2 adrenergique |
| DE60318193T2 (de) * | 2002-04-25 | 2008-12-04 | Glaxo Group Ltd., Greenford | Phenethanolaminderivate |
| EP1477167A1 (fr) * | 2003-05-15 | 2004-11-17 | Pfizer Limited | Dérivés de [(2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)-ethylamino)-propyl] phenyl come agonistes de beta2 |
-
2005
- 2005-03-10 AU AU2005223488A patent/AU2005223488A1/en not_active Abandoned
- 2005-03-10 BR BRPI0508927-1A patent/BRPI0508927A/pt not_active Application Discontinuation
- 2005-03-10 EA EA200601510A patent/EA200601510A1/ru unknown
- 2005-03-10 WO PCT/IB2005/000640 patent/WO2005090287A2/fr active Application Filing
- 2005-03-10 CA CA002559203A patent/CA2559203A1/fr not_active Abandoned
- 2005-03-10 EP EP05708731A patent/EP1727789A2/fr not_active Withdrawn
- 2005-03-10 JP JP2007503437A patent/JP4054366B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EA200601510A1 (ru) | 2007-04-27 |
| BRPI0508927A (pt) | 2007-08-14 |
| JP4054366B2 (ja) | 2008-02-27 |
| AU2005223488A1 (en) | 2005-09-29 |
| EP1727789A2 (fr) | 2006-12-06 |
| WO2005090287A3 (fr) | 2006-02-16 |
| JP2007529501A (ja) | 2007-10-25 |
| WO2005090287A2 (fr) | 2005-09-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |