RU2007134106A - Новые соединения ii, являющиеся производными 2-пиридина, в качестве ингибиторов - Google Patents
Новые соединения ii, являющиеся производными 2-пиридина, в качестве ингибиторов Download PDFInfo
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- RU2007134106A RU2007134106A RU2007134106/04A RU2007134106A RU2007134106A RU 2007134106 A RU2007134106 A RU 2007134106A RU 2007134106/04 A RU2007134106/04 A RU 2007134106/04A RU 2007134106 A RU2007134106 A RU 2007134106A RU 2007134106 A RU2007134106 A RU 2007134106A
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- Prior art keywords
- phenyl
- oxo
- carboxamide
- trifluoromethyl
- methyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- -1 nitro, methylcarbonyl Chemical group 0.000 claims abstract 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 12
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract 10
- 125000001424 substituent group Chemical group 0.000 claims abstract 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract 9
- 229910052717 sulfur Chemical group 0.000 claims abstract 9
- 150000002367 halogens Chemical class 0.000 claims abstract 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 7
- 239000001301 oxygen Chemical group 0.000 claims abstract 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 4
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 4
- 239000011593 sulfur Chemical group 0.000 claims abstract 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004429 atom Chemical group 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000004122 cyclic group Chemical group 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 4
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- DMVJCLKVSSYLLR-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 DMVJCLKVSSYLLR-UHFFFAOYSA-N 0.000 claims 2
- ZUIQRLIQXYYXHV-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfonyl-n,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC)=CC(S(=O)(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 ZUIQRLIQXYYXHV-UHFFFAOYSA-N 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- 102000016387 Pancreatic elastase Human genes 0.000 claims 2
- 108010067372 Pancreatic elastase Proteins 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000009267 bronchiectasis Diseases 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 210000001156 gastric mucosa Anatomy 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000003448 neutrophilic effect Effects 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 206010039083 rhinitis Diseases 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- GOWJROQOWDMVBZ-UHFFFAOYSA-N 1-(3-cyanophenyl)-5-(4-cyanophenyl)sulfinyl-6-methyl-n-[(5-methylsulfonylpyridin-2-yl)methyl]-2-oxopyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C#N)C(C)=C(S(=O)C=2C=CC(=CC=2)C#N)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=N1 GOWJROQOWDMVBZ-UHFFFAOYSA-N 0.000 claims 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- GYRJKDOPJGUSPE-UHFFFAOYSA-N 2-methyl-5-[(4-methylsulfonylphenyl)methylcarbamoyl]-6-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-sulfonic acid Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(O)(=O)=O)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 GYRJKDOPJGUSPE-UHFFFAOYSA-N 0.000 claims 1
- NSALXVMPIBZHHT-UHFFFAOYSA-N 5-(1h-imidazol-2-ylsulfinyl)-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2NC=CN=2)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 NSALXVMPIBZHHT-UHFFFAOYSA-N 0.000 claims 1
- MOTBECWQPPQDPL-UHFFFAOYSA-N 5-(2-cyanoethylsulfinyl)-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)CCC#N)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 MOTBECWQPPQDPL-UHFFFAOYSA-N 0.000 claims 1
- PAUGBMUDHIDLFV-UHFFFAOYSA-N 5-(4-acetamidophenyl)sulfinyl-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)C1=C(C)N(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C(C(=O)NCC=2C=CC(=CC=2)S(C)(=O)=O)=C1 PAUGBMUDHIDLFV-UHFFFAOYSA-N 0.000 claims 1
- YBHJQBHCNVLBBQ-UHFFFAOYSA-N 5-(4-acetamidophenyl)sulfonyl-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)C1=C(C)N(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C(C(=O)NCC=2C=CC(=CC=2)S(C)(=O)=O)=C1 YBHJQBHCNVLBBQ-UHFFFAOYSA-N 0.000 claims 1
- GSBCDEHBLZCQAA-UHFFFAOYSA-N 5-(4-bromophenyl)sulfinyl-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(Br)=CC=2)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 GSBCDEHBLZCQAA-UHFFFAOYSA-N 0.000 claims 1
- HQVWMCRXOFKKGL-UHFFFAOYSA-N 5-(4-bromophenyl)sulfinyl-n,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC)=CC(S(=O)C=2C=CC(Br)=CC=2)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 HQVWMCRXOFKKGL-UHFFFAOYSA-N 0.000 claims 1
- VOEWILCIPRQUFA-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfinyl-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(Cl)=CC=2)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 VOEWILCIPRQUFA-UHFFFAOYSA-N 0.000 claims 1
- MFIIUPQNQHZTRC-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfinyl-n,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC)=CC(S(=O)C=2C=CC(Cl)=CC=2)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 MFIIUPQNQHZTRC-UHFFFAOYSA-N 0.000 claims 1
- JWLGIQRRJSSKLE-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-1-(3,5-dichlorophenyl)-n,6-dimethyl-2-oxopyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC(Cl)=CC(Cl)=C1 JWLGIQRRJSSKLE-UHFFFAOYSA-N 0.000 claims 1
- HOGMYIXDMNBBIQ-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-1-(3,5-dichlorophenyl)-n-[(5-ethylsulfonylpyridin-2-yl)methyl]-6-methyl-2-oxopyridine-3-carboxamide Chemical compound N1=CC(S(=O)(=O)CC)=CC=C1CNC(=O)C(C1=O)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC(Cl)=CC(Cl)=C1 HOGMYIXDMNBBIQ-UHFFFAOYSA-N 0.000 claims 1
- VLJXGLTUOFMYLT-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-1-(3,5-difluorophenyl)-6-methyl-n-(2-morpholin-4-ylethyl)-2-oxopyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(F)C=C(F)C=2)C(C)=C(S(=O)C=2C=CC(=CC=2)C#N)C=C1C(=O)NCCN1CCOCC1 VLJXGLTUOFMYLT-UHFFFAOYSA-N 0.000 claims 1
- BYMZOLOJPBOJHJ-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-1-(3,5-difluorophenyl)-n,6-dimethyl-2-oxopyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC(F)=CC(F)=C1 BYMZOLOJPBOJHJ-UHFFFAOYSA-N 0.000 claims 1
- VFGWRXNWVNRFEE-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-1-(3,5-difluorophenyl)-n-[(5-ethylsulfonylpyridin-2-yl)methyl]-6-methyl-2-oxopyridine-3-carboxamide Chemical compound N1=CC(S(=O)(=O)CC)=CC=C1CNC(=O)C(C1=O)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC(F)=CC(F)=C1 VFGWRXNWVNRFEE-UHFFFAOYSA-N 0.000 claims 1
- DCBZAYLUTKGUSY-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-1-(3,5-difluorophenyl)-n-[2-(1h-imidazol-5-yl)ethyl]-6-methyl-2-oxopyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(F)C=C(F)C=2)C(C)=C(S(=O)C=2C=CC(=CC=2)C#N)C=C1C(=O)NCCC1=CNC=N1 DCBZAYLUTKGUSY-UHFFFAOYSA-N 0.000 claims 1
- GUZFBENKJIRRBH-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-6-methyl-1-(3-methylphenyl)-n-[(5-methylsulfonylpyridin-2-yl)methyl]-2-oxopyridine-3-carboxamide Chemical compound CC1=CC=CC(N2C(C(C(=O)NCC=3N=CC(=CC=3)S(C)(=O)=O)=CC(=C2C)S(=O)C=2C=CC(=CC=2)C#N)=O)=C1 GUZFBENKJIRRBH-UHFFFAOYSA-N 0.000 claims 1
- WCELYBQNMDUYPI-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound CC1=C(S(=O)C=2C=CC(=CC=2)C#N)C=C(C(N)=O)C(=O)N1C1=CC=CC(C(F)(F)F)=C1 WCELYBQNMDUYPI-UHFFFAOYSA-N 0.000 claims 1
- YDYDOJWRRZKZGN-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-6-methyl-2-oxo-n-[3-(2-oxopyrrolidin-1-yl)propyl]-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(=CC=2)C#N)C=C1C(=O)NCCCN1CCCC1=O YDYDOJWRRZKZGN-UHFFFAOYSA-N 0.000 claims 1
- ZMUFJLGATVEKRI-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-6-methyl-2-oxo-n-[3-(triazol-1-yl)propyl]-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(=CC=2)C#N)C=C1C(=O)NCCCN1C=CN=N1 ZMUFJLGATVEKRI-UHFFFAOYSA-N 0.000 claims 1
- MEYYJMGGAJGVIR-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-6-methyl-n-(2-morpholin-4-ylethyl)-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(=CC=2)C#N)C=C1C(=O)NCCN1CCOCC1 MEYYJMGGAJGVIR-UHFFFAOYSA-N 0.000 claims 1
- YOTZVYMIVMMKGQ-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(=CC=2)C#N)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 YOTZVYMIVMMKGQ-UHFFFAOYSA-N 0.000 claims 1
- OKCGFUAFULANFX-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-(1-hydroxy-2-methylpropan-2-yl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound CC1=C(S(=O)C=2C=CC(=CC=2)C#N)C=C(C(=O)NC(C)(C)CO)C(=O)N1C1=CC=CC(C(F)(F)F)=C1 OKCGFUAFULANFX-UHFFFAOYSA-N 0.000 claims 1
- XGSNKZPFXMVDRH-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-(2-hydroxy-2-methylpropyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound CC1=C(S(=O)C=2C=CC(=CC=2)C#N)C=C(C(=O)NCC(C)(C)O)C(=O)N1C1=CC=CC(C(F)(F)F)=C1 XGSNKZPFXMVDRH-UHFFFAOYSA-N 0.000 claims 1
- AXTKOOUFUDKUHQ-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-(2-hydroxyethyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound CC1=C(S(=O)C=2C=CC(=CC=2)C#N)C=C(C(=O)NCCO)C(=O)N1C1=CC=CC(C(F)(F)F)=C1 AXTKOOUFUDKUHQ-UHFFFAOYSA-N 0.000 claims 1
- NNFBDDCXLAIGQL-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-(2-hydroxypropyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NCC(O)C)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 NNFBDDCXLAIGQL-UHFFFAOYSA-N 0.000 claims 1
- KNOFFJVVPUYIBR-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-(2-methoxyethyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NCCOC)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 KNOFFJVVPUYIBR-UHFFFAOYSA-N 0.000 claims 1
- SAAHPVSQWALTKK-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-(2-methoxypropyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NCC(C)OC)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 SAAHPVSQWALTKK-UHFFFAOYSA-N 0.000 claims 1
- FYVYGVFLSFYYMY-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-(3-imidazol-1-ylpropyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(=CC=2)C#N)C=C1C(=O)NCCCN1C=CN=C1 FYVYGVFLSFYYMY-UHFFFAOYSA-N 0.000 claims 1
- AETHKXRZLNJOJN-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-[(1-hydroxycyclopropyl)methyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(=CC=2)C#N)C=C1C(=O)NCC1(O)CC1 AETHKXRZLNJOJN-UHFFFAOYSA-N 0.000 claims 1
- NNFBDDCXLAIGQL-OAMPWVDCSA-N 5-(4-cyanophenyl)sulfinyl-n-[(2r)-2-hydroxypropyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC[C@H](O)C)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 NNFBDDCXLAIGQL-OAMPWVDCSA-N 0.000 claims 1
- NNFBDDCXLAIGQL-XZRDNQIKSA-N 5-(4-cyanophenyl)sulfinyl-n-[(2s)-2-hydroxypropyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC[C@@H](O)C)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 NNFBDDCXLAIGQL-XZRDNQIKSA-N 0.000 claims 1
- QETUWPSKRBCSAT-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-[(5-ethylsulfonylpyridin-2-yl)methyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound N1=CC(S(=O)(=O)CC)=CC=C1CNC(=O)C(C1=O)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 QETUWPSKRBCSAT-UHFFFAOYSA-N 0.000 claims 1
- LCBOEUGSZHUWCQ-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-[2-(1h-imidazol-5-yl)ethyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(=CC=2)C#N)C=C1C(=O)NCCC1=CNC=N1 LCBOEUGSZHUWCQ-UHFFFAOYSA-N 0.000 claims 1
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- BNHQQOLRIMDHNM-UHFFFAOYSA-N n-ethyl-5-(4-fluorophenyl)sulfinyl-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NCC)=CC(S(=O)C=2C=CC(F)=CC=2)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 BNHQQOLRIMDHNM-UHFFFAOYSA-N 0.000 claims 1
- 229960003966 nicotinamide Drugs 0.000 claims 1
- 235000005152 nicotinamide Nutrition 0.000 claims 1
- 239000011570 nicotinamide Substances 0.000 claims 1
- 239000012038 nucleophile Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P11/16—Central respiratory analeptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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
- A61P35/00—Antineoplastic 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/83—Thioacids; Thioesters; Thioamides; Thioimides
-
- 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
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Otolaryngology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0500604 | 2005-03-16 | ||
| SE0500604-4 | 2005-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2007134106A true RU2007134106A (ru) | 2009-04-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| RU2007134106/04A RU2007134106A (ru) | 2005-03-16 | 2006-03-14 | Новые соединения ii, являющиеся производными 2-пиридина, в качестве ингибиторов |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US20090131483A1 (enExample) |
| EP (2) | EP1861371A4 (enExample) |
| JP (2) | JP2008533136A (enExample) |
| KR (1) | KR20070114154A (enExample) |
| CN (2) | CN101142188A (enExample) |
| AR (1) | AR053180A1 (enExample) |
| AU (1) | AU2006223675B2 (enExample) |
| BR (1) | BRPI0608636A2 (enExample) |
| CA (1) | CA2600038A1 (enExample) |
| IL (1) | IL184842A0 (enExample) |
| MX (1) | MX2007009372A (enExample) |
| NO (1) | NO20075059L (enExample) |
| RU (1) | RU2007134106A (enExample) |
| SA (1) | SA06270055B1 (enExample) |
| TW (1) | TW200700392A (enExample) |
| UY (1) | UY29420A1 (enExample) |
| WO (2) | WO2006098684A1 (enExample) |
| ZA (1) | ZA200706761B (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0302486D0 (sv) | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
| TW200808763A (en) | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds I |
| TW200808771A (en) * | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds II |
| EP2535330A3 (en) * | 2006-10-23 | 2012-12-26 | Takeda Pharmaceutical Company Limited | Iminopyridine derivative and use thereof |
| WO2009037413A1 (en) * | 2007-09-19 | 2009-03-26 | Argenta Discovery Limited | Dimers of 5- [ (4-cyanophenyl) sulfinyl] -6-methyl-2-oxo-1- [3- (trifluoromethyl)phenyl] -1,2-dihydropyridine-3-carboxamide as inhibitors of human neutrophil elastase for treating respiratory diseases |
| WO2009058076A1 (en) * | 2007-11-02 | 2009-05-07 | Astrazeneca Ab | 2-pyrazinone derivatives and their use as inhibitors of neutrophile elastase |
| BRPI0819258A2 (pt) | 2007-11-06 | 2017-05-02 | Astrazeneca Ab | alguns derivados de 2-pirazinona e seu uso como inibidores da elastase neutrófila |
| US20110039892A1 (en) * | 2008-04-23 | 2011-02-17 | Takeda Pharmaceutical Company Limited | Iminopyridine derivative and use thereof |
| JP5462803B2 (ja) * | 2008-04-23 | 2014-04-02 | 武田薬品工業株式会社 | イミノピリジン誘導体およびその用途 |
| US8481569B2 (en) | 2008-04-23 | 2013-07-09 | Takeda Pharmaceutical Company Limited | Iminopyridine derivatives and use thereof |
| EA201100311A1 (ru) | 2008-09-11 | 2011-10-31 | Пфайзер Инк. | Амидные производные гетероарилов и их применение в качестве активаторов глюкокиназы |
| CA2748587A1 (en) | 2009-01-20 | 2010-07-29 | Pfizer Inc. | Substituted pyrazinone amides |
| TW201036957A (en) | 2009-02-20 | 2010-10-16 | Astrazeneca Ab | Novel salt 628 |
| AU2010222589B2 (en) | 2009-03-11 | 2012-08-16 | Pfizer Inc. | Benzofuranyl derivatives used as glucokinase inhibitors |
| MX2012003644A (es) * | 2009-10-02 | 2012-04-30 | Astrazeneca Ab | Compuestos de 2-piridona empleados como inhibidores de la elastasa neutrofila. |
| US9458172B2 (en) * | 2012-03-02 | 2016-10-04 | Kenneth W Bair | Pyridinyl and pyrimidinyl sulfoxide and sulfone derivatives |
| US20140057926A1 (en) * | 2012-08-23 | 2014-02-27 | Boehringer Ingelheim International Gmbh | Substituted 4-pyridones and their use as inhibitors of neutrophil elastase activity |
| US20140057920A1 (en) | 2012-08-23 | 2014-02-27 | Boehringer Ingelheim International Gmbh | Substituted 4-pyridones and their use as inhibitors of neutrophil elastase activity |
| US9102624B2 (en) | 2012-08-23 | 2015-08-11 | Boehringer Ingelheim International Gmbh | Substituted 4-pyridones and their use as inhibitors of neutrophil elastase activity |
| EP3344615A1 (en) | 2015-09-02 | 2018-07-11 | GlaxoSmithKline Intellectual Property (No. 2) Limited | Pyridinone dicarboxamide for use as bromodomain inhibitors |
| EP3749697A4 (en) | 2018-02-05 | 2021-11-03 | Bio-Rad Laboratories, Inc. | CHROMATOGRAPHY RESIN WITH LIGAND MIXED MODE ANIONIC / HYDROPHOBIC EXCHANGE |
| WO2021053058A1 (en) | 2019-09-17 | 2021-03-25 | Mereo Biopharma 4 Limited | Alvelestat for use in the treatment of graft rejection, bronchiolitis obliterans syndrome and graft versus host disease |
| DK4106757T3 (da) | 2020-04-16 | 2023-10-23 | Mereo Biopharma 4 Ltd | Fremgangsmåder der involverer neutrofil elastase-inhibitor alvelestat til behandling af luftvejssygdom medieret af alpha-1-antitrypsin-mangel |
| AU2022373971A1 (en) | 2021-10-20 | 2024-04-04 | Mereo Biopharma 4 Limited | Neutrophil elastase inhibitors for use in the treatment of fibrosis |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2706977A1 (de) * | 1977-02-18 | 1978-08-24 | Hoechst Ag | Benzoesaeuren und deren derivate sowie verfahren zu ihrer herstellung |
| US5521179A (en) * | 1991-04-18 | 1996-05-28 | Zeneca Limited | Heterocyclic amides |
| US5441960A (en) * | 1992-04-16 | 1995-08-15 | Zeneca Limited | 1-pyrimidinylacetamide human leukocyte elastate inhibitors |
| KR20000075954A (ko) * | 1997-03-04 | 2000-12-26 | 죤 에이치. 뷰센 | Ｎ-히드록시 4-술포닐 부탄아미드 화합물 |
| CN1245386C (zh) * | 2000-06-12 | 2006-03-15 | 卫材株式会社 | 1,2－二氢吡啶化合物及其制备方法和用途 |
| ATE438624T1 (de) * | 2000-12-28 | 2009-08-15 | Shionogi & Co | 2-pyridonderivate mit affinität für den cannabinoid-typ-2-rezeptor |
| GB0129260D0 (en) * | 2001-12-06 | 2002-01-23 | Eisai London Res Lab Ltd | Pharmaceutical compositions and their uses |
| US7230017B2 (en) * | 2002-08-27 | 2007-06-12 | Bayer Healthcare Ag | Dihydropyridinone derivatives |
| TW200500341A (en) * | 2002-11-12 | 2005-01-01 | Astrazeneca Ab | Novel compounds |
| SE0302323D0 (sv) * | 2003-08-28 | 2003-08-28 | Astrazeneca Ab | Novel compounds |
| SE0302324D0 (sv) * | 2003-08-28 | 2003-08-28 | Astrazeneca Ab | Novel compounds |
| SE0302487D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
| SE0302486D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
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2006
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- 2006-03-14 JP JP2008501839A patent/JP2008533136A/ja active Pending
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- 2006-03-14 WO PCT/SE2006/000327 patent/WO2006098683A1/en not_active Ceased
- 2006-03-14 EP EP06717013A patent/EP1861371A4/en not_active Withdrawn
- 2006-03-14 CN CNA2006800085728A patent/CN101142189A/zh active Pending
- 2006-03-14 EP EP06717012A patent/EP1861370A1/en not_active Withdrawn
- 2006-03-14 KR KR1020077021054A patent/KR20070114154A/ko not_active Withdrawn
- 2006-03-14 RU RU2007134106/04A patent/RU2007134106A/ru not_active Application Discontinuation
- 2006-03-14 SA SA06270055A patent/SA06270055B1/ar unknown
- 2006-03-14 JP JP2008501840A patent/JP2008533137A/ja active Pending
- 2006-03-14 BR BRPI0608636-5A patent/BRPI0608636A2/pt not_active IP Right Cessation
- 2006-03-15 UY UY29420A patent/UY29420A1/es unknown
- 2006-03-16 AR ARP060101041A patent/AR053180A1/es unknown
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- 2007-07-26 IL IL184842A patent/IL184842A0/en unknown
- 2007-08-14 ZA ZA200706761A patent/ZA200706761B/xx unknown
- 2007-10-08 NO NO20075059A patent/NO20075059L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| UY29420A1 (es) | 2006-10-31 |
| JP2008533136A (ja) | 2008-08-21 |
| TW200700392A (en) | 2007-01-01 |
| CN101142188A (zh) | 2008-03-12 |
| ZA200706761B (en) | 2008-11-26 |
| KR20070114154A (ko) | 2007-11-29 |
| WO2006098683A1 (en) | 2006-09-21 |
| CN101142189A (zh) | 2008-03-12 |
| SA06270055B1 (ar) | 2009-02-07 |
| JP2008533137A (ja) | 2008-08-21 |
| WO2006098684A1 (en) | 2006-09-21 |
| EP1861370A1 (en) | 2007-12-05 |
| US20090131483A1 (en) | 2009-05-21 |
| EP1861371A1 (en) | 2007-12-05 |
| CA2600038A1 (en) | 2006-09-21 |
| AU2006223675A1 (en) | 2006-09-21 |
| BRPI0608636A2 (pt) | 2010-01-19 |
| AU2006223675B2 (en) | 2009-12-03 |
| US20090105239A1 (en) | 2009-04-23 |
| NO20075059L (no) | 2007-10-08 |
| MX2007009372A (es) | 2007-09-21 |
| IL184842A0 (en) | 2007-12-03 |
| AR053180A1 (es) | 2007-04-25 |
| EP1861371A4 (en) | 2011-08-10 |
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