JP2009525993A - 統合失調症の症状を治療または軽減するためにkcnq開口薬を使用する方法 - Google Patents
統合失調症の症状を治療または軽減するためにkcnq開口薬を使用する方法 Download PDFInfo
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- JP2009525993A JP2009525993A JP2008553621A JP2008553621A JP2009525993A JP 2009525993 A JP2009525993 A JP 2009525993A JP 2008553621 A JP2008553621 A JP 2008553621A JP 2008553621 A JP2008553621 A JP 2008553621A JP 2009525993 A JP2009525993 A JP 2009525993A
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- QCEHDLKQWVGPFI-UHFFFAOYSA-N ethyl n-[4-[(4-chlorophenyl)methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)C=C1 QCEHDLKQWVGPFI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/136—Amines having aromatic rings, e.g. ketamine, nortriptyline having the amino group directly attached to the aromatic ring, e.g. benzeneamine
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- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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- 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
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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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
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
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- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77130406P | 2006-02-07 | 2006-02-07 | |
| DKPA200600175 | 2006-02-07 | ||
| PCT/DK2007/050013 WO2007090409A1 (en) | 2006-02-07 | 2007-02-02 | Use of kcnq-openers for threating or reducing the symptoms of schizophrenia |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009525993A true JP2009525993A (ja) | 2009-07-16 |
| JP2009525993A5 JP2009525993A5 (enExample) | 2010-03-25 |
Family
ID=38055396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008553621A Ceased JP2009525993A (ja) | 2006-02-07 | 2007-02-02 | 統合失調症の症状を治療または軽減するためにkcnq開口薬を使用する方法 |
Country Status (16)
| Country | Link |
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Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011513196A (ja) * | 2007-08-01 | 2011-04-28 | ハー・ルンドベック・アクチエゼルスカベット | ドーパミン作動系が破壊された障害もしくは状態の症状を軽減するためまたはその障害もしくは状態を処置するためのkcnqカリウムチャネル開口薬の使用 |
| CA2804165C (en) | 2010-07-08 | 2015-02-24 | Pfizer Inc. | Piperidinyl pyrimidine amides as kv7 potassium channel openers |
| WO2016077724A1 (en) * | 2014-11-13 | 2016-05-19 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | (2-amino-4(arylamino)phenyl) carbamates |
| US10590067B2 (en) | 2018-02-20 | 2020-03-17 | H. Lundbeck A/S | Alcohol derivatives of carboxamides as Kv7 potassium channel openers |
| MA51881B1 (fr) | 2018-02-20 | 2023-08-31 | H Lundbeck As | Dérivés d'alcool utilisés en tant qu'agents d'ouverture du canal potassique kv7 |
| WO2019203951A1 (en) | 2018-04-20 | 2019-10-24 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Selective potassium channel agonists |
| RS66130B1 (sr) | 2019-08-02 | 2024-11-29 | H Lundbeck As | Derivati alkohola kao otvarači kv7 kalijumovih kanala |
| CN119490430A (zh) | 2019-08-02 | 2025-02-21 | H.隆德贝克有限公司 | 用于在癫痫或癫痫发作中使用的作为Kv7钾通道开放剂的醇衍生物 |
| AR119521A1 (es) | 2019-08-02 | 2021-12-22 | H Lundbeck As | DERIVADOS DE ALCOHOL COMO ABRIDORES DEL CANAL DE POTASIO Kv7 |
| US20230015539A1 (en) * | 2019-12-06 | 2023-01-19 | Icahn School Of Medicine At Mount Sinai | Method of treatment with kcnq channel openers |
Citations (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05345752A (ja) * | 1992-01-08 | 1993-12-27 | Asta Medica Ag | 新規の1,2,4−トリアミノベンゼン誘導体およびその製造方法 |
| WO2002062295A2 (en) * | 2001-02-02 | 2002-08-15 | Icagen, Inc. | Pyridine-substituted benzanilides as potassium ion channel openers |
| JP2003503447A (ja) * | 1999-07-01 | 2003-01-28 | グラクソ グループ リミテッド | カリウムチャンネルオープナーの新規用途 |
| US20030166650A1 (en) * | 2001-05-31 | 2003-09-04 | Yong-Jin Wu | Cinnamide derivatives as KCNQ potassium channel modulators |
| US20040106621A1 (en) * | 2002-11-22 | 2004-06-03 | Yong-Jin Wu | 3-Heterocyclic benzylamide derivatives as potassium channel openers |
| WO2004058739A1 (en) * | 2002-12-27 | 2004-07-15 | H. Lundbeck A/S | 1,2,4-triaminobenzene derivatives useful for treating disorders of the central nervous system |
| WO2004060880A1 (en) * | 2002-12-20 | 2004-07-22 | Bristol-Myers Squibb Company | Aminoalkyl thiazole derivatives as kcnq modulators |
| WO2004080377A2 (en) * | 2003-03-11 | 2004-09-23 | Neurosearch A/S | Kcnq channel modulating compounds and their pharmaceutical use |
| WO2004080950A1 (en) * | 2003-03-14 | 2004-09-23 | H. Lundbeck A/S | Substituted aniline derivatives |
| WO2004082677A1 (en) * | 2003-03-21 | 2004-09-30 | H. Lundbeck A/S | Substituted p-diaminobenzene derivatives |
| WO2004096767A1 (en) * | 2003-04-25 | 2004-11-11 | H. Lundbeck A/S | Sustituted indoline and indole derivatives |
| WO2005025293A2 (en) * | 2003-09-10 | 2005-03-24 | Icagen, Inc. | Fused ring heterocycles as potassium channel modulators |
| WO2005085276A1 (en) * | 2004-02-20 | 2005-09-15 | National Centre For Biological Sciences | A novel potassium channel modulator peptide |
| WO2005087754A1 (en) * | 2004-03-12 | 2005-09-22 | H. Lundbeck A/S | Substituted morpholine and thiomorpholine derivatives |
| WO2006029623A1 (en) * | 2004-09-13 | 2006-03-23 | H. Lundbeck A/S | Substituted aniline derivatives |
| WO2006092143A1 (en) * | 2005-03-03 | 2006-09-08 | H. Lundbeck A/S | Substituted pyridine derivatives |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4294142B2 (ja) | 1999-02-02 | 2009-07-08 | 株式会社日立製作所 | ディスクサブシステム |
| US6472165B1 (en) * | 1999-08-03 | 2002-10-29 | Arzneimittelwerk Dresden Gmbh | Modulatory binding site in potassium channels for screening and finding new active ingredients |
| CA2438868A1 (en) * | 2001-02-20 | 2002-09-19 | Valentin K. Gribkoff | Modulators of kcnq potassium channels and use thereof in treating migraine and mechanistically related diseases |
| US6469042B1 (en) * | 2001-02-20 | 2002-10-22 | Bristol-Myers Squibb Company | Fluoro oxindole derivatives as modulators if KCNQ potassium channels |
| DE10228103A1 (de) | 2002-06-24 | 2004-01-15 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| US7563748B2 (en) | 2003-06-23 | 2009-07-21 | Cognis Ip Management Gmbh | Alcohol alkoxylate carriers for pesticide active ingredients |
| WO2006000020A1 (en) | 2004-06-29 | 2006-01-05 | European Nickel Plc | Improved leaching of base metals |
| WO2007063418A2 (en) * | 2005-04-13 | 2007-06-07 | Neuraxon, Inc. | Substituted indole compounds having nos inhibitory activity |
-
2007
- 2007-02-02 EP EP12190206A patent/EP2554162A1/en not_active Withdrawn
- 2007-02-02 EP EP07702527A patent/EP1983974A1/en not_active Withdrawn
- 2007-02-02 BR BRPI0707495-6A patent/BRPI0707495A2/pt not_active IP Right Cessation
- 2007-02-02 JP JP2008553621A patent/JP2009525993A/ja not_active Ceased
- 2007-02-02 CA CA2641564A patent/CA2641564C/en not_active Expired - Fee Related
- 2007-02-02 KR KR1020087019396A patent/KR20080096659A/ko not_active Ceased
- 2007-02-02 AU AU2007214128A patent/AU2007214128B2/en not_active Ceased
- 2007-02-02 TW TW096103826A patent/TWI453013B/zh not_active IP Right Cessation
- 2007-02-02 CN CN2007800046484A patent/CN101378742B/zh not_active Expired - Fee Related
- 2007-02-02 EA EA200870232A patent/EA017915B1/ru not_active IP Right Cessation
- 2007-02-02 WO PCT/DK2007/050013 patent/WO2007090409A1/en not_active Ceased
- 2007-02-02 MX MX2008009655A patent/MX2008009655A/es active IP Right Grant
- 2007-02-02 NZ NZ569517A patent/NZ569517A/en not_active IP Right Cessation
- 2007-02-02 US US12/278,394 patent/US20090118285A1/en not_active Abandoned
- 2007-02-05 AR ARP070100469A patent/AR059319A1/es not_active Application Discontinuation
-
2008
- 2008-07-10 IL IL192745A patent/IL192745A0/en unknown
- 2008-09-05 NO NO20083838A patent/NO20083838L/no not_active Application Discontinuation
Patent Citations (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05345752A (ja) * | 1992-01-08 | 1993-12-27 | Asta Medica Ag | 新規の1,2,4−トリアミノベンゼン誘導体およびその製造方法 |
| JP2003503447A (ja) * | 1999-07-01 | 2003-01-28 | グラクソ グループ リミテッド | カリウムチャンネルオープナーの新規用途 |
| WO2002062295A2 (en) * | 2001-02-02 | 2002-08-15 | Icagen, Inc. | Pyridine-substituted benzanilides as potassium ion channel openers |
| US20030166650A1 (en) * | 2001-05-31 | 2003-09-04 | Yong-Jin Wu | Cinnamide derivatives as KCNQ potassium channel modulators |
| US20040106621A1 (en) * | 2002-11-22 | 2004-06-03 | Yong-Jin Wu | 3-Heterocyclic benzylamide derivatives as potassium channel openers |
| WO2004060880A1 (en) * | 2002-12-20 | 2004-07-22 | Bristol-Myers Squibb Company | Aminoalkyl thiazole derivatives as kcnq modulators |
| WO2004058739A1 (en) * | 2002-12-27 | 2004-07-15 | H. Lundbeck A/S | 1,2,4-triaminobenzene derivatives useful for treating disorders of the central nervous system |
| WO2004080377A2 (en) * | 2003-03-11 | 2004-09-23 | Neurosearch A/S | Kcnq channel modulating compounds and their pharmaceutical use |
| WO2004080950A1 (en) * | 2003-03-14 | 2004-09-23 | H. Lundbeck A/S | Substituted aniline derivatives |
| WO2004082677A1 (en) * | 2003-03-21 | 2004-09-30 | H. Lundbeck A/S | Substituted p-diaminobenzene derivatives |
| WO2004096767A1 (en) * | 2003-04-25 | 2004-11-11 | H. Lundbeck A/S | Sustituted indoline and indole derivatives |
| WO2005025293A2 (en) * | 2003-09-10 | 2005-03-24 | Icagen, Inc. | Fused ring heterocycles as potassium channel modulators |
| WO2005085276A1 (en) * | 2004-02-20 | 2005-09-15 | National Centre For Biological Sciences | A novel potassium channel modulator peptide |
| WO2005087754A1 (en) * | 2004-03-12 | 2005-09-22 | H. Lundbeck A/S | Substituted morpholine and thiomorpholine derivatives |
| WO2006029623A1 (en) * | 2004-09-13 | 2006-03-23 | H. Lundbeck A/S | Substituted aniline derivatives |
| WO2006092143A1 (en) * | 2005-03-03 | 2006-09-08 | H. Lundbeck A/S | Substituted pyridine derivatives |
Non-Patent Citations (4)
| Title |
|---|
| JPN6012033283; AKHONDZADEH,S. et al: 'Diazoxide in the treatment of schizophrenia: novel application of potassium channel openers in the t' J Clin Pharm Ther Vol.27, No.6, 2002, p.453-9 * |
| JPN6012033287; ZHANG,L. et al: 'Possible role of potassium channel, big K in etiology of schizophrenia' Med Hypotheses Vol.67, No.1, 2006, p.41-3 * |
| JPN6013008049; GRIBKOFF,V.K.: 'The therapeutic potential of neuronal KCNQ channel modulators' Expert Opin Ther Targets Vol.7, No.6, 2003, p.737-48 * |
| JPN6013008052; CZAPINSKI,P. et al: 'Mechanisms of action of antiepileptic drugs' Curr Top Med Chem Vol.5, No.1, 2005, p.3-14 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2554162A1 (en) | 2013-02-06 |
| AR059319A1 (es) | 2008-03-26 |
| EA200870232A1 (ru) | 2009-02-27 |
| IL192745A0 (en) | 2009-02-11 |
| AU2007214128B2 (en) | 2012-05-17 |
| CN101378742B (zh) | 2013-07-10 |
| NZ569517A (en) | 2011-07-29 |
| EA017915B1 (ru) | 2013-04-30 |
| CN101378742A (zh) | 2009-03-04 |
| MX2008009655A (es) | 2008-09-03 |
| CA2641564C (en) | 2012-06-12 |
| TWI453013B (zh) | 2014-09-21 |
| US20090118285A1 (en) | 2009-05-07 |
| KR20080096659A (ko) | 2008-10-31 |
| TW200808296A (en) | 2008-02-16 |
| NO20083838L (no) | 2008-10-31 |
| BRPI0707495A2 (pt) | 2011-05-03 |
| EP1983974A1 (en) | 2008-10-29 |
| CA2641564A1 (en) | 2007-08-16 |
| AU2007214128A1 (en) | 2007-08-16 |
| WO2007090409A1 (en) | 2007-08-16 |
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