JP2007524696A5 - - Google Patents
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- Publication number
- JP2007524696A5 JP2007524696A5 JP2007500099A JP2007500099A JP2007524696A5 JP 2007524696 A5 JP2007524696 A5 JP 2007524696A5 JP 2007500099 A JP2007500099 A JP 2007500099A JP 2007500099 A JP2007500099 A JP 2007500099A JP 2007524696 A5 JP2007524696 A5 JP 2007524696A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- substituted
- alkoxycarbonyl
- alkoxy
- 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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- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 67
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 58
- -1 C 1 -C 6 - alkyl Chemical group 0.000 claims 49
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 35
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 30
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 18
- 125000004043 oxo group Chemical group O=* 0.000 claims 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims 16
- 125000001153 fluoro group Chemical group F* 0.000 claims 16
- 125000001246 bromo group Chemical group Br* 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000002757 morpholinyl group Chemical group 0.000 claims 6
- 125000003386 piperidinyl group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 4
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims 2
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 2
- 206010007556 Cardiac failure acute Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 206010000891 acute myocardial infarction Diseases 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims 2
- 238000007634 remodeling Methods 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 108010028275 Leukocyte Elastase Proteins 0.000 claims 1
- 102000016799 Leukocyte elastase Human genes 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 230000002849 elastaseinhibitory effect Effects 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000010490 three component reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2007524696A JP2007524696A (ja) | 2007-08-30 |
| JP2007524696A5 true JP2007524696A5 (https=) | 2008-04-03 |
| JP4825194B2 JP4825194B2 (ja) | 2011-11-30 |
Family
ID=34895952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007500099A Expired - Fee Related JP4825194B2 (ja) | 2004-02-26 | 2005-02-15 | １，４−ジアリール−ジヒドロピリミジン−２−オン化合物およびヒト好中球エラスターゼ阻害剤としてのそれらの使用 |
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
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