JP2006526613A5 - - Google Patents
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- JP2006526613A5 JP2006526613A5 JP2006508431A JP2006508431A JP2006526613A5 JP 2006526613 A5 JP2006526613 A5 JP 2006526613A5 JP 2006508431 A JP2006508431 A JP 2006508431A JP 2006508431 A JP2006508431 A JP 2006508431A JP 2006526613 A5 JP2006526613 A5 JP 2006526613A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- propyl
- aminopyridin
- phenyl
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- -1 3- {2-[(2R) -2- (6-amino-pyridin-3-yl) -2-hydroxy-ethylamino] -propyl} -phenyl Chemical group 0.000 claims 113
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 70
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 40
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 38
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 34
- 150000001875 compounds Chemical class 0.000 claims 32
- 208000006673 asthma Diseases 0.000 claims 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 16
- 206010006451 bronchitis Diseases 0.000 claims 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 201000009267 bronchiectasis Diseases 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 6
- 239000003112 inhibitor Substances 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 4
- 239000005557 antagonist Substances 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 201000010659 intrinsic asthma Diseases 0.000 claims 4
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 208000023504 respiratory system disease Diseases 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 208000000884 Airway Obstruction Diseases 0.000 claims 2
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims 2
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 208000007451 chronic bronchitis Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000002458 infectious effect Effects 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 2
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 230000000414 obstructive effect Effects 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims 2
- HLUFJKVIOGXFLE-CJAUYULYSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(2,3-dihydro-1h-inden-2-yl)acetamide Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C(CC(=O)NC3CC4=CC=CC=C4C3)C=CC=2)C)=CC=C(N)N=C1 HLUFJKVIOGXFLE-CJAUYULYSA-N 0.000 claims 1
- MMZJKMJQAVXSPB-DVECYGJZSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(2-phenylethyl)acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCCC1=CC=CC=C1 MMZJKMJQAVXSPB-DVECYGJZSA-N 0.000 claims 1
- XESNJJXNSNRFDW-NLFFAJNJSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(3-phenylpropyl)acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCCCC1=CC=CC=C1 XESNJJXNSNRFDW-NLFFAJNJSA-N 0.000 claims 1
- XGAOFZOAEPBTRU-DVECYGJZSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(2-ethoxyphenyl)methyl]acetamide Chemical compound CCOC1=CC=CC=C1CNC(=O)CC1=CC=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 XGAOFZOAEPBTRU-DVECYGJZSA-N 0.000 claims 1
- OEBAFKHZOOOJFF-JPYJTQIMSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(2-methoxyphenyl)methyl]acetamide Chemical compound COC1=CC=CC=C1CNC(=O)CC1=CC=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 OEBAFKHZOOOJFF-JPYJTQIMSA-N 0.000 claims 1
- AEFMLSXFSRUOAN-MWTRTKDXSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(3,4-dichlorophenyl)methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC=C(Cl)C(Cl)=C1 AEFMLSXFSRUOAN-MWTRTKDXSA-N 0.000 claims 1
- SBGFKFIFWKTORP-NLFFAJNJSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(3,4-dimethylphenyl)methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC=C(C)C(C)=C1 SBGFKFIFWKTORP-NLFFAJNJSA-N 0.000 claims 1
- FTFZJGUKLJRXDO-JPYJTQIMSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-benzylacetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC=CC=C1 FTFZJGUKLJRXDO-JPYJTQIMSA-N 0.000 claims 1
- LQBJKTDDUSJZEW-VWLOTQADSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(2,3-dihydro-1h-inden-2-yl)acetamide Chemical compound C1([C@@H](O)CNC(C)(CC=2C=C(CC(=O)NC3CC4=CC=CC=C4C3)C=CC=2)C)=CC=C(N)N=C1 LQBJKTDDUSJZEW-VWLOTQADSA-N 0.000 claims 1
- FRSKICZSOVEZJD-DEOSSOPVSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(2-phenylethyl)acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCCC1=CC=CC=C1 FRSKICZSOVEZJD-DEOSSOPVSA-N 0.000 claims 1
- KANMKKLTVIMZTE-VWLOTQADSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(3-phenylpropyl)acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCCCC1=CC=CC=C1 KANMKKLTVIMZTE-VWLOTQADSA-N 0.000 claims 1
- JWMKEGVOSSRVSG-DEOSSOPVSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(2-ethoxyphenyl)methyl]acetamide Chemical compound CCOC1=CC=CC=C1CNC(=O)CC1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 JWMKEGVOSSRVSG-DEOSSOPVSA-N 0.000 claims 1
- ZCMOQGZWQJCPTB-QHCPKHFHSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(3,4-dichlorophenyl)methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=C(Cl)C(Cl)=C1 ZCMOQGZWQJCPTB-QHCPKHFHSA-N 0.000 claims 1
- KLJXQQGRQKJFCX-VWLOTQADSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(3,4-dimethylphenyl)methyl]acetamide Chemical compound C1=C(C)C(C)=CC=C1CNC(=O)CC1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 KLJXQQGRQKJFCX-VWLOTQADSA-N 0.000 claims 1
- XKWFZRDOLVRRPS-QHCPKHFHSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(3,5-dichlorophenyl)methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC(Cl)=CC(Cl)=C1 XKWFZRDOLVRRPS-QHCPKHFHSA-N 0.000 claims 1
- BOZURQMZWFCEBE-QHCPKHFHSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-benzylacetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=CC=C1 BOZURQMZWFCEBE-QHCPKHFHSA-N 0.000 claims 1
- XIUIDNNUSWLERE-IMMUGOHXSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(3,4,5-trimethoxyphenyl)methyl]acetamide Chemical compound COC1=C(OC)C(OC)=CC(CNC(=O)CC=2C=C(CC(C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 XIUIDNNUSWLERE-IMMUGOHXSA-N 0.000 claims 1
- GSYFRMJARSANCF-KESSSICBSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC(C(F)(F)F)=CC=C1F GSYFRMJARSANCF-KESSSICBSA-N 0.000 claims 1
- PYIRKRDWPLLOFQ-VXLWULRPSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[3-(trifluoromethoxy)phenyl]methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=CC(OC(F)(F)F)=C1 PYIRKRDWPLLOFQ-VXLWULRPSA-N 0.000 claims 1
- OYSNGYJFJSOGIK-KESSSICBSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[3-fluoro-4-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=C(C(F)(F)F)C(F)=C1 OYSNGYJFJSOGIK-KESSSICBSA-N 0.000 claims 1
- DVNRJVHCQZTSEB-VXLWULRPSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[4-(trifluoromethoxy)phenyl]methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=C(OC(F)(F)F)C=C1 DVNRJVHCQZTSEB-VXLWULRPSA-N 0.000 claims 1
- GVXZASNOAYOREY-KESSSICBSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[4-fluoro-2-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=C(F)C=C1C(F)(F)F GVXZASNOAYOREY-KESSSICBSA-N 0.000 claims 1
- VLQAVCAPEAIPRO-QHCPKHFHSA-N 2-[4-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(2,6-dimethoxyphenyl)methyl]acetamide Chemical compound COC1=CC=CC(OC)=C1CNC(=O)CC(C=C1)=CC=C1CC(C)(C)NC[C@H](O)C1=CC=C(N)N=C1 VLQAVCAPEAIPRO-QHCPKHFHSA-N 0.000 claims 1
- PJBCMWNFRRXAKY-DEOSSOPVSA-N 2-[4-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(3-methoxyphenyl)methyl]acetamide Chemical compound COC1=CC=CC(CNC(=O)CC=2C=CC(CC(C)(C)NC[C@H](O)C=3C=NC(N)=CC=3)=CC=2)=C1 PJBCMWNFRRXAKY-DEOSSOPVSA-N 0.000 claims 1
- 150000003930 2-aminopyridines Chemical class 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- UVFVAKJMQXHLIL-ZHRRBRCNSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(2-hydroxy-5-methylphenyl)benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NC1=CC(C)=CC=C1O UVFVAKJMQXHLIL-ZHRRBRCNSA-N 0.000 claims 1
- QTINNCGAARTPJK-QRQCRPRQSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(3-hydroxy-2-methylphenyl)benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NC1=CC=CC(O)=C1C QTINNCGAARTPJK-QRQCRPRQSA-N 0.000 claims 1
- BXTQSBJWMMSWBU-VFNWGFHPSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(3-hydroxy-4-methoxyphenyl)benzamide Chemical compound C1=C(O)C(OC)=CC=C1NC(=O)C1=CC=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 BXTQSBJWMMSWBU-VFNWGFHPSA-N 0.000 claims 1
- APPVRYWZAFXGQX-VFNWGFHPSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(3-hydroxyphenyl)benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NC1=CC=CC(O)=C1 APPVRYWZAFXGQX-VFNWGFHPSA-N 0.000 claims 1
- CPBMOWXLMAIYRD-VFNWGFHPSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(4-hydroxyphenyl)benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NC1=CC=C(O)C=C1 CPBMOWXLMAIYRD-VFNWGFHPSA-N 0.000 claims 1
- UUEQNTWXVVSGRW-QFSZVTIDSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(5-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C(C=CC=2)C(=O)NC2C3=CC=CC(O)=C3CCC2)C)=CC=C(N)N=C1 UUEQNTWXVVSGRW-QFSZVTIDSA-N 0.000 claims 1
- YPVODFPCTDEFJD-OSPHWJPCSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[(2-chloro-4-hydroxyphenyl)methyl]-n-ethylbenzamide Chemical compound C=1C=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=CC=1C(=O)N(CC)CC1=CC=C(O)C=C1Cl YPVODFPCTDEFJD-OSPHWJPCSA-N 0.000 claims 1
- ZMZRHPKCSOPLNR-OSPHWJPCSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[(2-chloro-5-hydroxyphenyl)methyl]-n-ethylbenzamide Chemical compound C=1C=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=CC=1C(=O)N(CC)CC1=CC(O)=CC=C1Cl ZMZRHPKCSOPLNR-OSPHWJPCSA-N 0.000 claims 1
- FBSQYSNPBGQPDZ-HXOBKFHXSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[(2-hydroxyphenyl)methyl]-n-methylbenzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)N(C)CC1=CC=CC=C1O FBSQYSNPBGQPDZ-HXOBKFHXSA-N 0.000 claims 1
- OXYMFVCGRSKNLM-OSPHWJPCSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[(3-chloro-5-hydroxyphenyl)methyl]-n-ethylbenzamide Chemical compound C=1C=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=CC=1C(=O)N(CC)CC1=CC(O)=CC(Cl)=C1 OXYMFVCGRSKNLM-OSPHWJPCSA-N 0.000 claims 1
- GEIDDDLGOYNGHJ-HXOBKFHXSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[2-(2-hydroxyphenyl)ethyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCCC1=CC=CC=C1O GEIDDDLGOYNGHJ-HXOBKFHXSA-N 0.000 claims 1
- JBTSTUYGGAJQOD-HXOBKFHXSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[2-(4-hydroxyphenyl)ethyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCCC1=CC=C(O)C=C1 JBTSTUYGGAJQOD-HXOBKFHXSA-N 0.000 claims 1
- NLKDZJIWBSKQGE-CLOONOSVSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-ethyl-n-[2-(4-hydroxyphenyl)ethyl]benzamide Chemical compound C=1C=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=CC=1C(=O)N(CC)CCC1=CC=C(O)C=C1 NLKDZJIWBSKQGE-CLOONOSVSA-N 0.000 claims 1
- XKGMBJQFLBSAMN-NRFANRHFSA-N 3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-(3-hydroxyphenyl)benzamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NC1=CC=CC(O)=C1 XKGMBJQFLBSAMN-NRFANRHFSA-N 0.000 claims 1
- HHGFCHFVLBYWML-QHCPKHFHSA-N 3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-[2-(2-hydroxyphenyl)ethyl]benzamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=CC=C1O HHGFCHFVLBYWML-QHCPKHFHSA-N 0.000 claims 1
- PFZWHJXQOCKLDN-QHCPKHFHSA-N 3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-[2-(3-hydroxyphenyl)ethyl]benzamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=CC(O)=C1 PFZWHJXQOCKLDN-QHCPKHFHSA-N 0.000 claims 1
- SJAWPIAGCDYKTR-QFIPXVFZSA-N 3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethyl]benzamide Chemical compound COC1=C(O)C(OC)=CC(CCNC(=O)C=2C=C(CC(C)(C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 SJAWPIAGCDYKTR-QFIPXVFZSA-N 0.000 claims 1
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| EP1830837B1 (en) | 2004-09-20 | 2013-09-04 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
| AU2005286728A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase |
| AR051090A1 (es) | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| JP5149009B2 (ja) | 2004-09-20 | 2013-02-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | ヒトステアロイル−ＣｏＡデサチュラーゼを阻害するためのピリダジン誘導体 |
| MX2007003332A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de estearoil-coa-desaturasa. |
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| EP2029138A1 (en) | 2005-06-03 | 2009-03-04 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| GB0514809D0 (en) | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
| GB0516313D0 (en) | 2005-08-08 | 2005-09-14 | Argenta Discovery Ltd | Azole derivatives and their uses |
| RU2442771C2 (ru) | 2005-08-08 | 2012-02-20 | Арджента Дискавери Лтд | Производные бицикло[2,2,1]гепт-7-иламина и их применения |
| MY144906A (en) | 2005-10-21 | 2011-11-30 | Novartis Ag | Human antibodies against il13 and therapeutic uses |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| AR060607A1 (es) | 2006-04-21 | 2008-07-02 | Novartis Ag | Derivados de purina,composiciones farmaceuticas que los contienen, metodo de preparacion y usos en enfermedades obstructivas o inflamatorias de las vias respiratorias. |
| US8163758B2 (en) * | 2006-06-09 | 2012-04-24 | Parion Sciences, Inc. | Phenyl substituted pyrazinoylguanidine sodium channel blockers possessing beta agonist activity |
| EP2535330A3 (en) | 2006-10-23 | 2012-12-26 | Takeda Pharmaceutical Company Limited | Iminopyridine derivative and use thereof |
| AU2008248598B2 (en) | 2007-05-07 | 2011-11-17 | Novartis Ag | Organic compounds |
| ES2654395T3 (es) | 2007-12-10 | 2018-02-13 | Novartis Ag | Análogos de amilorida espirocíclicos como bloqueantes de ENaC |
| JP5584138B2 (ja) | 2008-01-11 | 2014-09-03 | ノバルティス アーゲー | キナーゼ阻害剤としてのピリミジン類 |
| US8481569B2 (en) | 2008-04-23 | 2013-07-09 | Takeda Pharmaceutical Company Limited | Iminopyridine derivatives and use thereof |
| EP2300010B1 (en) | 2008-06-10 | 2015-03-04 | Novartis AG | Pyrazine derivatives as epithelial sodium channel blockers |
| US8236786B2 (en) | 2008-08-07 | 2012-08-07 | Pulmagen Therapeutics (Inflammation) Limited | Respiratory disease treatment |
| DE102008049675A1 (de) | 2008-09-30 | 2010-04-01 | Markus Dr. Heinrich | Verfahren zur Herstellung von 3-Aminobiphenylen |
| WO2010076553A1 (en) | 2008-12-30 | 2010-07-08 | Dr. Reddy's Laboratories Ltd | Sulfonamide compounds for the treatment of respiratory disorders |
| WO2010150014A1 (en) | 2009-06-24 | 2010-12-29 | Pulmagen Therapeutics (Inflammation) Limited | 5r- 5 -deuterated glitazones for respiratory disease treatment |
| MX2012004792A (es) | 2009-10-22 | 2013-02-01 | Vertex Pharma | Composiciones para el tratamiento de fibrosis quistica y otras enfermedades cronicas. |
| GB0918923D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Aminothiazole derivatives |
| GB0918924D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Azaindole derivatives |
| GB0918922D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Aminopyridine derivatives |
| WO2011098746A1 (en) | 2010-02-09 | 2011-08-18 | Pulmagen Therapeutics (Inflammation) Limited | Crystalline acid addition salts of ( 5r) -enanti0mer of pioglitazone |
| GB201002224D0 (en) | 2010-02-10 | 2010-03-31 | Argenta Therapeutics Ltd | Respiratory disease treatment |
| GB201002243D0 (en) | 2010-02-10 | 2010-03-31 | Argenta Therapeutics Ltd | Respiratory disease treatment |
| US8247436B2 (en) | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
| UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| US8372845B2 (en) | 2010-09-17 | 2013-02-12 | Novartis Ag | Pyrazine derivatives as enac blockers |
| JP5959541B2 (ja) | 2011-02-25 | 2016-08-02 | ノバルティス アーゲー | Ｔｒｋ阻害剤としてのピラゾロ［１，５−ａ］ピリジン |
| UY34305A (es) | 2011-09-01 | 2013-04-30 | Novartis Ag | Derivados de heterociclos bicíclicos para el tratamiento de la hipertensión arterial pulmonar |
| WO2013038381A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine/pyrazine amide derivatives |
| WO2013038378A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| WO2013038373A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| US9034879B2 (en) | 2011-09-16 | 2015-05-19 | Novartis Ag | Heterocyclic compounds for the treatment of CF |
| ES2882807T3 (es) | 2011-09-16 | 2021-12-02 | Novartis Ag | Heterociclil carboxamidas N-sustituidas |
| US8809340B2 (en) | 2012-03-19 | 2014-08-19 | Novartis Ag | Crystalline form |
| US9073921B2 (en) | 2013-03-01 | 2015-07-07 | Novartis Ag | Salt forms of bicyclic heterocyclic derivatives |
| WO2015162461A1 (en) | 2014-04-24 | 2015-10-29 | Novartis Ag | Pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| MX2016013812A (es) | 2014-04-24 | 2017-03-09 | Novartis Ag | Derivados de amino-pirazina como inhibidores de fosfatidil-inositol-3-cinasa. |
| EA201692140A1 (ru) | 2014-04-24 | 2017-04-28 | Новартис Аг | Производные аминопиридина в качестве ингибиторов фосфатидилинозитол 3-киназы |
| JP2022537667A (ja) | 2019-06-10 | 2022-08-29 | ノバルティス アーゲー | Ｃｆ、ｃｏｐｄ、及び気管支拡張症の治療のためのピリジン及びピラジン誘導体 |
| EP4021572A1 (en) | 2019-08-28 | 2022-07-06 | Novartis AG | Substituted 1,3-phenyl heteroaryl derivatives and their use in the treatment of disease |
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| US4358455A (en) * | 1980-12-23 | 1982-11-09 | Merck & Co., Inc. | Aralkylamindethanol heterocyclic compounds |
| WO1996035671A1 (en) * | 1995-05-10 | 1996-11-14 | Pfizer Inc. | β-ADRENERGIC AGONISTS |
| EP1078924B1 (en) * | 1999-07-23 | 2004-10-20 | Pfizer Products Inc. | Intermediates and a process for producing beta-adrenergic receptor agonists |
| TWI249515B (en) * | 2001-11-13 | 2006-02-21 | Theravance Inc | Aryl aniline beta2 adrenergic receptor agonists |
| GB0217225D0 (en) * | 2002-07-25 | 2002-09-04 | Glaxo Group Ltd | Medicinal compounds |
| DE60320439T2 (de) * | 2002-10-11 | 2009-05-20 | Pfizer Inc. | INDOLDERIVATE ALS ß2-AGONISTEN |
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