CA2519987A1 - Benzofuro-1,4-diazepin-2-one derivatives - Google Patents
Benzofuro-1,4-diazepin-2-one derivatives Download PDFInfo
- Publication number
- CA2519987A1 CA2519987A1 CA002519987A CA2519987A CA2519987A1 CA 2519987 A1 CA2519987 A1 CA 2519987A1 CA 002519987 A CA002519987 A CA 002519987A CA 2519987 A CA2519987 A CA 2519987A CA 2519987 A1 CA2519987 A1 CA 2519987A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compounds
- bromine
- chlorine
- hydrogen
- 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.)
- Abandoned
Links
- SLIFXYAKJLAJKJ-UHFFFAOYSA-N [1]benzofuro[3,2-e][1,4]diazepin-2-one Chemical class O=C1C=NC=C2OC3=CC=CC=C3C2=N1 SLIFXYAKJLAJKJ-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000003814 drug Substances 0.000 claims abstract description 9
- 238000011282 treatment Methods 0.000 claims abstract description 9
- 206010003210 Arteriosclerosis Diseases 0.000 claims abstract description 8
- 208000011775 arteriosclerosis disease Diseases 0.000 claims abstract description 8
- 208000037803 restenosis Diseases 0.000 claims abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- 238000011321 prophylaxis Methods 0.000 claims abstract description 7
- 201000010099 disease Diseases 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Chemical group 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
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- 241001465754 Metazoa Species 0.000 claims description 2
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- -1 alkyl radical Chemical class 0.000 description 23
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- 238000012360 testing method Methods 0.000 description 9
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- 230000014509 gene expression Effects 0.000 description 6
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- 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]
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- 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
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Animal Behavior & Ethology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10312969.3 | 2003-03-24 | ||
| DE10312969A DE10312969A1 (de) | 2003-03-24 | 2003-03-24 | Benzofuro-1,4-diazepin-2-on-Derivate |
| PCT/EP2004/002580 WO2004085440A1 (de) | 2003-03-24 | 2004-03-12 | Benzofuro-1,4-diazepin-2-on-derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2519987A1 true CA2519987A1 (en) | 2004-10-07 |
Family
ID=32946087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002519987A Abandoned CA2519987A1 (en) | 2003-03-24 | 2004-03-12 | Benzofuro-1,4-diazepin-2-one derivatives |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1608659A1 (de) |
| JP (1) | JP2006521308A (de) |
| CA (1) | CA2519987A1 (de) |
| DE (1) | DE10312969A1 (de) |
| WO (1) | WO2004085440A1 (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9969700B2 (en) | 2012-01-13 | 2018-05-15 | Nippon Chemiphar Co., Ltd. | P2X4 receptor antagonist |
| WO2021198745A1 (ja) * | 2020-03-30 | 2021-10-07 | ルーカ アントニオーリ | 過敏性腸症候群又は炎症性腸疾患の予防又は治療のための医薬 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009057281A (ja) * | 2005-12-19 | 2009-03-19 | Nippon Chemiphar Co Ltd | Ｐ２ｘ４受容体拮抗剤 |
| JP2009062278A (ja) * | 2005-12-29 | 2009-03-26 | Nippon Chemiphar Co Ltd | Ｐ２ｘ４受容体拮抗剤 |
| WO2008020651A1 (fr) * | 2006-08-17 | 2008-02-21 | Kyushu University, National University Corporation | antagoniste de récepteur P2X4 |
| US20100256123A1 (en) | 2006-08-25 | 2010-10-07 | Nippon Chemiphar Co., Ltd. | P2x4 receptor antagonist |
| WO2009022731A1 (ja) | 2007-08-10 | 2009-02-19 | Nippon Chemiphar Co., Ltd. | Ｐ２ｘ４受容体拮抗剤 |
| KR101727761B1 (ko) | 2009-02-16 | 2017-04-17 | 닛뽕 케미파 가부시키가이샤 | 디아제핀디온 유도체 |
| JP5843770B2 (ja) * | 2010-07-13 | 2016-01-13 | 日本ケミファ株式会社 | Ｐ２ｘ４受容体拮抗剤 |
| EP2631229B1 (de) | 2010-07-29 | 2014-12-03 | Nippon Chemiphar Co., Ltd. | P2x4-rezeptorantagonist |
| EP2617717B1 (de) | 2010-08-03 | 2016-03-02 | Nippon Chemiphar Co., Ltd. | P2x4-rezeptor-antagonisten |
| CA2819997C (en) | 2010-11-05 | 2019-06-25 | Kyushu University | Preventive or therapeutic agent for pain associated with herpes zoster in acute phase |
| WO2012161301A1 (ja) * | 2011-05-25 | 2012-11-29 | 国立大学法人九州大学 | ギラン・バレー症候群に伴う神経因性疼痛の予防又は治療剤 |
| CA2864606C (en) | 2012-02-15 | 2021-06-15 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Methods of treating and preventing diseases and disorders of the central nervous system |
| AU2014288115C1 (en) | 2013-07-12 | 2018-11-15 | Kyushu University | P2X4 receptor antagonist |
| EP3020717B1 (de) | 2013-07-12 | 2021-12-15 | Nippon Chemiphar Co., Ltd. | P2x4-rezeptor-antagonist |
| WO2015088565A1 (en) * | 2013-12-13 | 2015-06-18 | Sunovion Pharmaceuticals Inc. | P2x4 receptor modulating compounds and methods of use thereof |
| JP7116679B2 (ja) * | 2016-04-28 | 2022-08-10 | 日本ケミファ株式会社 | 多発性硬化症の治療のための医薬 |
| US10695355B2 (en) | 2017-03-30 | 2020-06-30 | University Of Connecticut | Methods for pharmacologic treatment of stroke |
| WO2023239767A2 (en) * | 2022-06-07 | 2023-12-14 | University Of Connecticut | Compositions and methods for pharmacologic treatment of stroke and myocardial ischemia reperfusion injury |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW219896B (de) * | 1988-07-07 | 1994-02-01 | Duphar Int Res | |
| ATE336492T1 (de) * | 2000-01-14 | 2006-09-15 | Us Gov Health & Human Serv | Methonocarbacycloalkylanaloga von nucleosiden |
-
2003
- 2003-03-24 DE DE10312969A patent/DE10312969A1/de not_active Withdrawn
-
2004
- 2004-03-12 WO PCT/EP2004/002580 patent/WO2004085440A1/de active Application Filing
- 2004-03-12 EP EP04719947A patent/EP1608659A1/de not_active Withdrawn
- 2004-03-12 CA CA002519987A patent/CA2519987A1/en not_active Abandoned
- 2004-03-12 JP JP2006504663A patent/JP2006521308A/ja active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9969700B2 (en) | 2012-01-13 | 2018-05-15 | Nippon Chemiphar Co., Ltd. | P2X4 receptor antagonist |
| US10633349B2 (en) | 2012-01-13 | 2020-04-28 | Nippon Chemiphar Co., Ltd | P2X4 receptor antagonist |
| US11434207B2 (en) | 2012-01-13 | 2022-09-06 | Nippon Chemiphar Co., Ltd | P2X4 receptor antagonist |
| WO2021198745A1 (ja) * | 2020-03-30 | 2021-10-07 | ルーカ アントニオーリ | 過敏性腸症候群又は炎症性腸疾患の予防又は治療のための医薬 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1608659A1 (de) | 2005-12-28 |
| DE10312969A1 (de) | 2004-10-07 |
| JP2006521308A (ja) | 2006-09-21 |
| WO2004085440A1 (de) | 2004-10-07 |
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