CA2557271C - 1,4-diaryl-dihydropyrimidin-2-ones and their use as human neutrophil elastase inhibitors - Google Patents
1,4-diaryl-dihydropyrimidin-2-ones and their use as human neutrophil elastase inhibitors Download PDFInfo
- Publication number
- CA2557271C CA2557271C CA2557271A CA2557271A CA2557271C CA 2557271 C CA2557271 C CA 2557271C CA 2557271 A CA2557271 A CA 2557271A CA 2557271 A CA2557271 A CA 2557271A CA 2557271 C CA2557271 C CA 2557271C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- group
- substituted
- alkoxycarbonyl
- alkyl
- 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.)
- Expired - Fee Related
Links
- 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 title 1
- 102000052502 human ELANE Human genes 0.000 title 1
- 239000003591 leukocyte elastase inhibitor Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 9
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims abstract 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract 4
- 206010000891 acute myocardial infarction Diseases 0.000 claims abstract 4
- 239000003814 drug Substances 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims 31
- 150000003839 salts Chemical class 0.000 claims 16
- 239000012453 solvate Substances 0.000 claims 16
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- -1 benzyloxy, benzyloxycarbonyl Chemical group 0.000 claims 8
- 125000001246 bromo group Chemical group Br* 0.000 claims 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 3
- 208000011191 Pulmonary vascular disease Diseases 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 239000002552 dosage form Substances 0.000 claims 3
- 230000002757 inflammatory effect Effects 0.000 claims 3
- 230000000302 ischemic effect Effects 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 230000002685 pulmonary effect Effects 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 239000007943 implant Substances 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 206010007556 Cardiac failure acute Diseases 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- 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
- 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
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D413/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04004314.3 | 2004-02-26 | ||
| EP04004314 | 2004-02-26 | ||
| PCT/EP2005/001486 WO2005082864A1 (en) | 2004-02-26 | 2005-02-15 | 1,4-diaryl-dihydropyrimidin-2-ones and their use as human neutrophil elastase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2557271A1 CA2557271A1 (en) | 2005-09-09 |
| CA2557271C true CA2557271C (en) | 2012-08-21 |
Family
ID=34895952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2557271A Expired - Fee Related CA2557271C (en) | 2004-02-26 | 2005-02-15 | 1,4-diaryl-dihydropyrimidin-2-ones and their use as human neutrophil elastase inhibitors |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8101615B2 (https=) |
| EP (1) | EP1723121B1 (https=) |
| JP (1) | JP4825194B2 (https=) |
| CA (1) | CA2557271C (https=) |
| ES (1) | ES2394177T3 (https=) |
| WO (1) | WO2005082864A1 (https=) |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0302486D0 (sv) | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
| WO2005080372A1 (en) * | 2004-02-19 | 2005-09-01 | Bayer Healthcare Ag | Dihydropyridinone derivatives |
| ES2428503T3 (es) | 2004-02-26 | 2013-11-08 | Bayer Intellectual Property Gmbh | 1,4-Diaril-dihidropirimidin-2-onas y su uso como inhibidores de elastasa de neutrófilos humanos |
| CA2590851A1 (en) * | 2004-12-16 | 2006-06-22 | Bayer Healthcare Ag | Crystal structure of enzyme and uses thereof |
| GB0502258D0 (en) * | 2005-02-03 | 2005-03-09 | Argenta Discovery Ltd | Compounds and their use |
| GB0516313D0 (en) | 2005-08-08 | 2005-09-14 | Argenta Discovery Ltd | Azole derivatives and their uses |
| JP2009504624A (ja) | 2005-08-08 | 2009-02-05 | アージェンタ ディスカバリー リミテッド | ビシクロ［２．２．１］ヘプタ−７−イルアミン誘導体およびその使用 |
| 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 |
| DE102006031314A1 (de) * | 2006-07-01 | 2008-01-03 | Bayer Healthcare Aktiengesellschaft | Verwendung von 1,4-Diaryl-dihydropyrimidin-2-on-Derivaten zur Behandlung der pulmonalen arteriellen Hyptertonie |
| WO2008104752A1 (en) * | 2007-02-26 | 2008-09-04 | Astrazeneca Ab | Dihydropyridones as elastase inhibitors |
| DE102007019691A1 (de) | 2007-04-26 | 2008-10-30 | Bayer Healthcare Ag | Verwendung von acyclisch substituierten Furopyrimidin-Derivaten zur Behandlung der pulmonalen arteriellen Hypertonie |
| DE102007019690A1 (de) | 2007-04-26 | 2008-10-30 | Bayer Healthcare Ag | Verwendung von cyclisch substituierten Furopyrimidin-Derivaten zur Behandlung der pulmonalen arteriellen Hypertonie |
| DE102007027800A1 (de) | 2007-06-16 | 2008-12-18 | Bayer Healthcare Ag | Substituierte bicyclische Heteroaryl-Verbindungen und ihre Verwendung |
| DE102007027799A1 (de) | 2007-06-16 | 2008-12-18 | Bayer Healthcare Ag | Substituierte Furopyrimidine und ihre Verwendung |
| DE102007051762A1 (de) | 2007-10-30 | 2009-05-07 | Bayer Healthcare Ag | Substituierte Pyrrolotriazine und ihre Verwendung |
| EP2217591A4 (en) | 2007-11-06 | 2011-10-26 | Astrazeneca Ab | CERTAIN 2-PYRAZINONE DERIVATIVES AND THEIR USE AS NEUTROPHILES ELASTASE INHIBITORS |
| DE102007054786A1 (de) | 2007-11-16 | 2009-05-20 | Bayer Healthcare Ag | Trisubstituierte Furopyrimidine und ihre Verwendung |
| DE102007061766A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | 4-(4-Cyano-2-thioaryl)-dihydropyrimidinone und ihre Verwendung |
| DE102008022521A1 (de) * | 2008-05-07 | 2009-11-12 | Bayer Schering Pharma Aktiengesellschaft | 1,4-Diaryl-pyrimidopyridazin-2,5-dione und ihre Verwendung |
| CN101903356B (zh) * | 2007-12-20 | 2013-05-22 | 拜耳知识产权有限责任公司 | 4-(4-氰基-2-硫代芳基)二氢嘧啶酮和它们的使用 |
| DE102008052013A1 (de) | 2008-10-17 | 2010-04-22 | Bayer Schering Pharma Aktiengesellschaft | 4-(4-Cyano-2-thioaryl)-dihydropyrimidinone und ihre Verwendung |
| DE102008007400A1 (de) | 2008-02-04 | 2009-08-06 | Bayer Healthcare Ag | Substituierte Furane und ihre Verwendung |
| WO2009149836A1 (en) * | 2008-06-09 | 2009-12-17 | Bayer Schering Pharma Aktiengesellschaft | Annellated 4- (indazolyl) -1,4-dihydropyridine derivatives and methods of use thereof |
| DE102009004197A1 (de) | 2009-01-09 | 2010-07-15 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch anellierte Diaryldihydropyrimidin-Derivate und ihre Verwendung |
| TW201036957A (en) | 2009-02-20 | 2010-10-16 | Astrazeneca Ab | Novel salt 628 |
| DE102009016553A1 (de) | 2009-04-06 | 2010-10-07 | Bayer Schering Pharma Aktiengesellschaft | Sulfonamid- und Sulfoximin-substituierte Diaryldihydropyrimidinone und ihre Verwendung |
| CN102639537B (zh) * | 2009-07-10 | 2015-07-22 | 拜耳知识产权有限责任公司 | 吲唑基取代的二氢异*唑并吡啶及其使用方法 |
| AU2010302420B2 (en) | 2009-10-02 | 2013-07-04 | Astrazeneca Ab | 2-pyridone compounds used as inhibitors of neutrophil elastase |
| GB0918924D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Azaindole derivatives |
| GB0918923D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Aminothiazole derivatives |
| GB0918922D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Aminopyridine derivatives |
| DE102010030187A1 (de) | 2010-06-16 | 2011-12-22 | Bayer Schering Pharma Aktiengesellschaft | 4-Cyan-2-sulfonylphenyl)pyrazolyl-substituierte Pyridinone und Pyrazinone und ihre Verwendung |
| US20140221335A1 (en) | 2013-02-06 | 2014-08-07 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9115093B2 (en) | 2013-03-04 | 2015-08-25 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9924721B2 (en) * | 2013-08-28 | 2018-03-27 | Bayer Cropscience Aktiengesellschaft | Malonic ester derivatives of heteroarylpiperidines and -piperazines as fungicides |
| KR102284938B1 (ko) * | 2013-11-27 | 2021-08-02 | 선샤인 레이크 파르마 컴퍼니 리미티드 | 다이하이드로피리미딘 유도체 및 이의 중간산물의 제조 방법 |
| USRE47493E1 (en) | 2014-02-20 | 2019-07-09 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US20170022171A1 (en) | 2014-04-03 | 2017-01-26 | Bayer Pharma Aktiengesellschaft | 2,5-disubstituted cyclopentanecarboxylic acids and their use |
| US20170119776A1 (en) | 2014-04-03 | 2017-05-04 | Bayer Pharma Aktiengesellschaft | Chiral 2,5-disubstituted cyclopentanecarboxylic acid derivatives and use thereof |
| CA2944614A1 (en) | 2014-04-03 | 2015-10-08 | Bayer Pharma Aktiengesellschaft | 2,5-disubstituted cyclopentane carboxylic acids for the treatment of respiratoy tract diseases |
| US9290457B2 (en) * | 2014-07-31 | 2016-03-22 | Boehringer Ingelheim International Gmbh | Substituted dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9440930B2 (en) | 2014-07-31 | 2016-09-13 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9657015B2 (en) | 2014-07-31 | 2017-05-23 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9475779B2 (en) | 2014-07-31 | 2016-10-25 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9458113B2 (en) | 2014-07-31 | 2016-10-04 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| KR20170129191A (ko) | 2015-03-18 | 2017-11-24 | 바이엘 파마 악티엔게젤샤프트 | (4s)-4-[4-사이아노-2-(메틸설폰일)페닐]-3,6-다이메틸-2-옥소-1-[3-(트라이플루오로메틸)페닐]-1,2,3,4-테트라하이드로 피리미딘-5-카보나이트릴의 생성 방법 |
| TWI810220B (zh) | 2017-11-17 | 2023-08-01 | 德商拜耳廠股份有限公司 | 經取代之巨環吲哚衍生物 |
| US12030879B2 (en) | 2018-03-02 | 2024-07-09 | Inflazome Limited | Sulfonyl acetamides as NLRP3 inhibitors |
| US11834433B2 (en) | 2018-03-02 | 2023-12-05 | Inflazome Limited | Compounds |
| US12168653B2 (en) | 2018-03-02 | 2024-12-17 | Inflazome Limited | Sulfonamide derivates as NLRP3 inhibitors |
| WO2019166632A1 (en) | 2018-03-02 | 2019-09-06 | Inflazome Limited | Novel compounds |
| EP3759078A1 (en) | 2018-03-02 | 2021-01-06 | Inflazome Limited | Novel compounds |
| 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 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9214053D0 (en) | 1992-07-02 | 1992-08-12 | Ici Plc | Heterocyclic amides |
| DE60214428T2 (de) * | 2001-12-20 | 2007-09-20 | Bayer Healthcare Ag | 1, 4-dihydro-1, 4-diphenylpyridin-derivate |
| GB2392910A (en) * | 2002-09-10 | 2004-03-17 | Bayer Ag | 2-Oxopyrimidine derivatives and their use as human leukocyte elastase inhibitors |
| EP1546113B1 (en) * | 2002-09-10 | 2013-05-01 | Bayer Intellectual Property GmbH | Pyrimidinone derivatives as therapeutic agents against acute and chronic inflammatory, ischaemic and remodelling processes |
| WO2005037799A1 (en) | 2003-10-16 | 2005-04-28 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| US7435837B2 (en) * | 2003-10-24 | 2008-10-14 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| WO2005080372A1 (en) | 2004-02-19 | 2005-09-01 | Bayer Healthcare Ag | Dihydropyridinone derivatives |
| ES2428503T3 (es) | 2004-02-26 | 2013-11-08 | Bayer Intellectual Property Gmbh | 1,4-Diaril-dihidropirimidin-2-onas y su uso como inhibidores de elastasa de neutrófilos humanos |
-
2005
- 2005-02-15 JP JP2007500099A patent/JP4825194B2/ja not_active Expired - Fee Related
- 2005-02-15 WO PCT/EP2005/001486 patent/WO2005082864A1/en not_active Ceased
- 2005-02-15 EP EP05707386A patent/EP1723121B1/en not_active Expired - Lifetime
- 2005-02-15 CA CA2557271A patent/CA2557271C/en not_active Expired - Fee Related
- 2005-02-15 ES ES05707386T patent/ES2394177T3/es not_active Expired - Lifetime
- 2005-02-15 US US10/590,770 patent/US8101615B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US8101615B2 (en) | 2012-01-24 |
| JP4825194B2 (ja) | 2011-11-30 |
| US20080064704A1 (en) | 2008-03-13 |
| CA2557271A1 (en) | 2005-09-09 |
| EP1723121A1 (en) | 2006-11-22 |
| ES2394177T3 (es) | 2013-01-23 |
| EP1723121B1 (en) | 2012-07-25 |
| WO2005082864A1 (en) | 2005-09-09 |
| JP2007524696A (ja) | 2007-08-30 |
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| EEER | Examination request | ||
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