JP2009536197A5 - - Google Patents
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- Publication number
- JP2009536197A5 JP2009536197A5 JP2009509486A JP2009509486A JP2009536197A5 JP 2009536197 A5 JP2009536197 A5 JP 2009536197A5 JP 2009509486 A JP2009509486 A JP 2009509486A JP 2009509486 A JP2009509486 A JP 2009509486A JP 2009536197 A5 JP2009536197 A5 JP 2009536197A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- alkyl
- formula
- oxo
- compound
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 16
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 125000001153 fluoro group Chemical group F* 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 239000001301 oxygen Chemical group 0.000 claims 6
- 229910052717 sulfur Chemical group 0.000 claims 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 4
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 claims 4
- 208000027418 Wounds and injury 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
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- 206010006451 bronchitis Diseases 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- 108010028275 Leukocyte Elastase Proteins 0.000 claims 2
- 102000016799 Leukocyte elastase Human genes 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000008469 Peptic Ulcer Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 206010052428 Wound Diseases 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 230000009286 beneficial effect Effects 0.000 claims 2
- 201000009267 bronchiectasis Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 208000007451 chronic bronchitis Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 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
- 230000002496 gastric effect Effects 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 208000011906 peptic ulcer disease Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 206010039083 rhinitis Diseases 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- XEHNFWVIZMCCBK-UHFFFAOYSA-N (5-methylsulfonylpyridin-2-yl)methanamine Chemical compound CS(=O)(=O)C1=CC=C(CN)N=C1 XEHNFWVIZMCCBK-UHFFFAOYSA-N 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 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
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical group OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims 1
- MZANAXJJGALDLS-UHFFFAOYSA-N 2-[[6-[2-(4-cyanophenyl)pyrazol-3-yl]-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carbonyl]amino]acetic acid Chemical compound CC1=C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)N=C(C(=O)NCC(O)=O)C(=O)N1C1=CC=CC(C(F)(F)F)=C1 MZANAXJJGALDLS-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims 1
- WUSFKVQGOLXKQK-UHFFFAOYSA-N 6-[2-(4-chlorophenyl)pyrazol-3-yl]-n,5-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carboxamide Chemical compound CC=1N(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C(C(=O)NC)=NC=1C1=CC=NN1C1=CC=C(Cl)C=C1 WUSFKVQGOLXKQK-UHFFFAOYSA-N 0.000 claims 1
- SCQULGSHZWJDPM-UHFFFAOYSA-N 6-[2-(4-cyanophenyl)pyrazol-3-yl]-5-methyl-n-[(5-methylsulfonylpyridin-2-yl)methyl]-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)N=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=N1 SCQULGSHZWJDPM-UHFFFAOYSA-N 0.000 claims 1
- CZXQVSBHQWORIR-UHFFFAOYSA-N 6-[2-(4-cyanophenyl)pyrazol-3-yl]-n,5-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carboxamide Chemical compound CC=1N(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C(C(=O)NC)=NC=1C1=CC=NN1C1=CC=C(C#N)C=C1 CZXQVSBHQWORIR-UHFFFAOYSA-N 0.000 claims 1
- TVMRPCPJKYZXFG-UHFFFAOYSA-N 6-[2-(4-cyanophenyl)pyrazol-3-yl]-n,n,5-trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carboxamide Chemical compound CC=1N(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C(C(=O)N(C)C)=NC=1C1=CC=NN1C1=CC=C(C#N)C=C1 TVMRPCPJKYZXFG-UHFFFAOYSA-N 0.000 claims 1
- LCUYXVNEQVXZIJ-UHFFFAOYSA-N 6-[2-(4-cyanophenyl)pyrazol-3-yl]-n-(1-hydroxy-2-methylpropan-2-yl)-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carboxamide Chemical compound CC1=C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)N=C(C(=O)NC(C)(C)CO)C(=O)N1C1=CC=CC(C(F)(F)F)=C1 LCUYXVNEQVXZIJ-UHFFFAOYSA-N 0.000 claims 1
- VXFVIAPZULVIFL-UHFFFAOYSA-N 6-[2-(4-cyanophenyl)pyrazol-3-yl]-n-cyclopropyl-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)N=C1C(=O)NC1CC1 VXFVIAPZULVIFL-UHFFFAOYSA-N 0.000 claims 1
- ZRJDPTREGVHMGQ-UHFFFAOYSA-N 6-[2-(4-cyanophenyl)pyrazol-3-yl]-n-ethyl-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carboxamide Chemical compound CC=1N(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C(C(=O)NCC)=NC=1C1=CC=NN1C1=CC=C(C#N)C=C1 ZRJDPTREGVHMGQ-UHFFFAOYSA-N 0.000 claims 1
- SGUPMZFLRHPHQI-UHFFFAOYSA-N 6-[2-(5-cyanopyridin-2-yl)pyrazol-3-yl]-n,5-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carboxamide Chemical compound CC=1N(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C(C(=O)NC)=NC=1C1=CC=NN1C1=CC=C(C#N)C=N1 SGUPMZFLRHPHQI-UHFFFAOYSA-N 0.000 claims 1
- DVIYHBLIUWYHST-UHFFFAOYSA-N 6-[2-(5-cyanopyridin-2-yl)pyrazol-3-yl]-n-cyclopropyl-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(C=2N(N=CC=2)C=2N=CC(=CC=2)C#N)N=C1C(=O)NC1CC1 DVIYHBLIUWYHST-UHFFFAOYSA-N 0.000 claims 1
- CHRGDTSVXIPUHY-UHFFFAOYSA-N 6-[2-(6-cyanopyridin-3-yl)pyrazol-3-yl]-n,5-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carboxamide Chemical compound CC=1N(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C(C(=O)NC)=NC=1C1=CC=NN1C1=CC=C(C#N)N=C1 CHRGDTSVXIPUHY-UHFFFAOYSA-N 0.000 claims 1
- LMWQVAJRBJDDOE-UHFFFAOYSA-N 6-[2-(6-cyanopyridin-3-yl)pyrazol-3-yl]-n-cyclopropyl-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(C=2N(N=CC=2)C=2C=NC(=CC=2)C#N)N=C1C(=O)NC1CC1 LMWQVAJRBJDDOE-UHFFFAOYSA-N 0.000 claims 1
- QQQNWVOBRASKAV-UHFFFAOYSA-N 6-[3-(4-chlorophenyl)triazol-4-yl]-n,5-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carboxamide Chemical compound CC=1N(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C(C(=O)NC)=NC=1C1=CN=NN1C1=CC=C(Cl)C=C1 QQQNWVOBRASKAV-UHFFFAOYSA-N 0.000 claims 1
- OBMLGXKIHVSLHG-UHFFFAOYSA-N 6-[3-(4-cyanophenyl)triazol-4-yl]-n,5-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]pyrazine-2-carboxamide Chemical compound CC=1N(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C(C(=O)NC)=NC=1C1=CN=NN1C1=CC=C(C#N)C=C1 OBMLGXKIHVSLHG-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000012038 nucleophile Substances 0.000 claims 1
- 150000007524 organic acids Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 150000002926 oxygen Chemical class 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
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 0 CC(N=C1C(N(*)**)=O)=C(*)N(*)C1=O Chemical compound CC(N=C1C(N(*)**)=O)=C(*)N(*)C1=O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79878406P | 2006-05-08 | 2006-05-08 | |
| US60/798,784 | 2006-05-08 | ||
| PCT/SE2007/000442 WO2007129963A1 (en) | 2006-05-08 | 2007-05-07 | 2-pyrazinone derivatives for the treatment of disease or condition in which inhibition of neutrophil elastase activity is beneficial. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009536197A JP2009536197A (ja) | 2009-10-08 |
| JP2009536197A5 true JP2009536197A5 (https=) | 2010-06-03 |
| JP5527739B2 JP5527739B2 (ja) | 2014-06-25 |
Family
ID=38667998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009509486A Expired - Fee Related JP5527739B2 (ja) | 2006-05-08 | 2007-05-07 | 好中球エラスターゼ活性の阻害が有益である疾患または状態の処置のための２−ピリドン誘導体 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US8114881B2 (https=) |
| EP (1) | EP2018377A4 (https=) |
| JP (1) | JP5527739B2 (https=) |
| KR (1) | KR101429303B1 (https=) |
| CN (1) | CN101490040B (https=) |
| AR (1) | AR060874A1 (https=) |
| AU (2) | AU2007248951B2 (https=) |
| BR (1) | BRPI0711362A2 (https=) |
| CA (1) | CA2650553C (https=) |
| CL (1) | CL2007001283A1 (https=) |
| CO (1) | CO6140058A2 (https=) |
| EC (1) | ECSP088869A (https=) |
| IL (1) | IL194949A0 (https=) |
| MX (1) | MX2008013837A (https=) |
| NO (1) | NO20084845L (https=) |
| RU (2) | RU2448098C2 (https=) |
| SG (1) | SG170101A1 (https=) |
| TW (1) | TW200808771A (https=) |
| UY (1) | UY30327A1 (https=) |
| WO (1) | WO2007129963A1 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0302486D0 (sv) | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
| TW200808771A (en) | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds II |
| TW200808763A (en) * | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds I |
| JP5140154B2 (ja) | 2007-06-27 | 2013-02-06 | アストラゼネカ・アクチエボラーグ | ピラジノン誘導体および肺疾患の処置におけるそれらの使用 |
| WO2009058076A1 (en) * | 2007-11-02 | 2009-05-07 | Astrazeneca Ab | 2-pyrazinone derivatives and their use as inhibitors of neutrophile elastase |
| EP2217591A4 (en) | 2007-11-06 | 2011-10-26 | Astrazeneca Ab | CERTAIN 2-PYRAZINONE DERIVATIVES AND THEIR USE AS NEUTROPHILES ELASTASE INHIBITORS |
| AR073711A1 (es) | 2008-10-01 | 2010-11-24 | Astrazeneca Ab | Derivados de isoquinolina |
| TW201036957A (en) * | 2009-02-20 | 2010-10-16 | Astrazeneca Ab | Novel salt 628 |
| GB0913345D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | New combination 802 |
| AU2010302420B2 (en) | 2009-10-02 | 2013-07-04 | Astrazeneca Ab | 2-pyridone compounds used as inhibitors of neutrophil elastase |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| WO2011110852A1 (en) | 2010-03-10 | 2011-09-15 | Astrazeneca Ab | Polymorphic forms of 6- [2- (4 -cyanophenyl) - 2h - pyrazol - 3 - yl] - 5 -methyl - 3 - oxo - 4 - (trifluoromethyl - phenyl) 3,4-dihydropyrazine-2-carboxylic acid ethylamide |
| DE102010030187A1 (de) | 2010-06-16 | 2011-12-22 | Bayer Schering Pharma Aktiengesellschaft | 4-Cyan-2-sulfonylphenyl)pyrazolyl-substituierte Pyridinone und Pyrazinone und ihre Verwendung |
| JP2013177318A (ja) * | 2010-06-30 | 2013-09-09 | Dainippon Sumitomo Pharma Co Ltd | ジヒドロピリミジノン誘導体およびその医薬用途 |
| GB201016912D0 (en) | 2010-10-07 | 2010-11-24 | Astrazeneca Ab | Novel combination |
| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| TW201247631A (en) | 2011-04-28 | 2012-12-01 | Du Pont | Herbicidal pyrazinones |
| US9102624B2 (en) | 2012-08-23 | 2015-08-11 | Boehringer Ingelheim International Gmbh | Substituted 4-pyridones and their use as inhibitors of neutrophil elastase activity |
| 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 |
| KR20180074793A (ko) * | 2015-11-13 | 2018-07-03 | 바이엘 파마 악티엔게젤샤프트 | 만성 상처 치료를 위한 4-(4-시아노-2-티오아릴)다이하이드로피리미디논 |
| WO2017207430A1 (en) * | 2016-05-31 | 2017-12-07 | Chiesi Farmaceutici S.P.A. | Imidazolone compounds as human neutrophil elastase inhibitors |
| EP3749697A4 (en) | 2018-02-05 | 2021-11-03 | Bio-Rad Laboratories, Inc. | CHROMATOGRAPHY RESIN WITH LIGAND MIXED MODE ANIONIC / HYDROPHOBIC EXCHANGE |
| CN108440508B (zh) * | 2018-04-04 | 2020-03-20 | 河南科技大学第一附属医院 | 吡嗪药物及其制备方法、组合物及在胃肠病人护理的应用 |
| JP7672641B2 (ja) | 2019-09-17 | 2025-05-08 | メレオ バイオファーマ ４ リミテッド | 移植片拒絶反応、閉塞性細気管支炎症候群、及び移植片対宿主病の治療に使用するためのアルベレスタット |
| IL297211B2 (en) | 2020-04-16 | 2025-12-01 | Mereo Biopharma 4 Ltd | Methods involving neutrophil elastase inhibitor alvelestat for treating respiratory disease mediated by alpha-1 antitrypsin deficiency |
| KR20240090272A (ko) | 2021-10-20 | 2024-06-21 | 메레오 바이오파마 4 리미티드 | 섬유화 치료에 사용하기 위한 호중구 엘라스테이스 억제제 |
| EP4447960A1 (en) * | 2021-12-16 | 2024-10-23 | Orixa Therapeutics LLC | Small molecule inhibitors of pr3 and hne and uses thereof |
| CN118724801B (zh) * | 2024-09-03 | 2024-12-03 | 中节能万润股份有限公司 | 一种甲苯磺酸艾多沙班中间体的制备方法 |
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| FR2358891A1 (fr) * | 1976-07-22 | 1978-02-17 | Yamanouchi Pharma Co Ltd | Composes heterocycliques contenant un azote, utilise comme agents analgesiques et anti-inflammatoires |
| DE2706977A1 (de) * | 1977-02-18 | 1978-08-24 | Hoechst Ag | Benzoesaeuren und deren derivate sowie verfahren zu ihrer herstellung |
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| GB0129260D0 (en) | 2001-12-06 | 2002-01-23 | Eisai London Res Lab Ltd | Pharmaceutical compositions and their uses |
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| TW200500341A (en) * | 2002-11-12 | 2005-01-01 | Astrazeneca Ab | Novel compounds |
| SE0302324D0 (sv) | 2003-08-28 | 2003-08-28 | Astrazeneca Ab | Novel compounds |
| SE0302323D0 (sv) | 2003-08-28 | 2003-08-28 | Astrazeneca Ab | Novel compounds |
| SE0302486D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
| SE0302487D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
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| TW200700392A (en) * | 2005-03-16 | 2007-01-01 | Astrazeneca Ab | Novel compounds |
| JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
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| TW200808763A (en) * | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds I |
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| TW201036957A (en) * | 2009-02-20 | 2010-10-16 | Astrazeneca Ab | Novel salt 628 |
| AU2010302420B2 (en) * | 2009-10-02 | 2013-07-04 | Astrazeneca Ab | 2-pyridone compounds used as inhibitors of neutrophil elastase |
-
2007
- 2007-04-27 TW TW096115050A patent/TW200808771A/zh unknown
- 2007-05-07 CN CN2007800259264A patent/CN101490040B/zh not_active Expired - Fee Related
- 2007-05-07 BR BRPI0711362-5A patent/BRPI0711362A2/pt not_active IP Right Cessation
- 2007-05-07 MX MX2008013837A patent/MX2008013837A/es active IP Right Grant
- 2007-05-07 EP EP07748106A patent/EP2018377A4/en not_active Withdrawn
- 2007-05-07 US US12/299,878 patent/US8114881B2/en not_active Expired - Fee Related
- 2007-05-07 UY UY30327A patent/UY30327A1/es unknown
- 2007-05-07 WO PCT/SE2007/000442 patent/WO2007129963A1/en not_active Ceased
- 2007-05-07 AU AU2007248951A patent/AU2007248951B2/en not_active Ceased
- 2007-05-07 CA CA2650553A patent/CA2650553C/en not_active Expired - Fee Related
- 2007-05-07 JP JP2009509486A patent/JP5527739B2/ja not_active Expired - Fee Related
- 2007-05-07 RU RU2008143457/04A patent/RU2448098C2/ru not_active IP Right Cessation
- 2007-05-07 CL CL2007001283A patent/CL2007001283A1/es unknown
- 2007-05-07 KR KR1020087029813A patent/KR101429303B1/ko not_active Expired - Fee Related
- 2007-05-07 SG SG201101743-1A patent/SG170101A1/en unknown
- 2007-05-08 AR ARP070101993A patent/AR060874A1/es not_active Application Discontinuation
-
2008
- 2008-10-27 IL IL194949A patent/IL194949A0/en unknown
- 2008-10-28 CO CO08115221A patent/CO6140058A2/es unknown
- 2008-11-06 EC EC2008008869A patent/ECSP088869A/es unknown
- 2008-11-18 NO NO20084845A patent/NO20084845L/no not_active Application Discontinuation
-
2010
- 2010-10-26 AU AU2010236027A patent/AU2010236027B2/en not_active Ceased
-
2011
- 2011-07-27 RU RU2011131170/04A patent/RU2011131170A/ru not_active Application Discontinuation
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2012
- 2012-01-06 US US13/344,658 patent/US8410114B2/en not_active Expired - Fee Related
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