NO333610B1 - Anvendelse av alfa-aminamidderivater ved fremstilling av et medikament for behandling av hodepinetilstander - Google Patents
Anvendelse av alfa-aminamidderivater ved fremstilling av et medikament for behandling av hodepinetilstander Download PDFInfo
- Publication number
- NO333610B1 NO333610B1 NO20053780A NO20053780A NO333610B1 NO 333610 B1 NO333610 B1 NO 333610B1 NO 20053780 A NO20053780 A NO 20053780A NO 20053780 A NO20053780 A NO 20053780A NO 333610 B1 NO333610 B1 NO 333610B1
- Authority
- NO
- Norway
- Prior art keywords
- propanamide
- headache
- benzylamino
- hydrogen
- alkyl
- Prior art date
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Classifications
-
- 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
-
- 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
-
- 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
- A61P25/06—Antimigraine agents
-
- 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]
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03000921A EP1438956A1 (en) | 2003-01-16 | 2003-01-16 | Alpha-aminoamide derivatives useful as antimigraine agents |
| PCT/EP2003/012889 WO2004062655A1 (en) | 2003-01-16 | 2003-11-18 | Alpha-aminoamide derivatives useful as antimigraine agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20053780D0 NO20053780D0 (no) | 2005-08-09 |
| NO20053780L NO20053780L (no) | 2005-10-13 |
| NO333610B1 true NO333610B1 (no) | 2013-07-22 |
Family
ID=32524140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20053780A NO333610B1 (no) | 2003-01-16 | 2005-08-09 | Anvendelse av alfa-aminamidderivater ved fremstilling av et medikament for behandling av hodepinetilstander |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7709523B2 (ja) |
| EP (2) | EP1438956A1 (ja) |
| JP (1) | JP4885455B2 (ja) |
| KR (1) | KR101049694B1 (ja) |
| CN (1) | CN100418517C (ja) |
| AT (1) | ATE380026T1 (ja) |
| AU (1) | AU2003279399B8 (ja) |
| BR (1) | BRPI0317795B8 (ja) |
| CA (1) | CA2510514C (ja) |
| CY (1) | CY1107274T1 (ja) |
| DE (1) | DE60317935T2 (ja) |
| DK (1) | DK1585510T3 (ja) |
| ES (1) | ES2295658T3 (ja) |
| HK (1) | HK1086487A1 (ja) |
| MX (1) | MXPA05007339A (ja) |
| NO (1) | NO333610B1 (ja) |
| NZ (1) | NZ541117A (ja) |
| PT (1) | PT1585510E (ja) |
| RU (1) | RU2336077C2 (ja) |
| SI (1) | SI1585510T1 (ja) |
| WO (1) | WO2004062655A1 (ja) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9727523D0 (en) | 1997-12-31 | 1998-02-25 | Pharmacia & Upjohn Spa | Alpha-aminoamide derivatives useful as analgesic agents |
| JP4350508B2 (ja) * | 2001-09-03 | 2009-10-21 | ニユーロン・フアーマシユーテイカルズ・エツセ・ピー・アー | ガバペンチンまたはその類似体とα−アミノアミドとを含む薬剤組成物およびその鎮痛用途 |
| CA2536764C (en) * | 2003-08-25 | 2013-09-17 | Newron Pharmaceuticals, S.P.A. | .alpha.-aminoamide derivatives useful as anti-inflammatory agents |
| BRPI0515154A (pt) * | 2004-09-10 | 2008-07-08 | Newron Pharm Spa | uso de (halobenzilóxi)benzilamino-propanamidas para a fabricação de medicamentos ativos, compostos e composição farmacêutica |
| EP1963280B1 (en) * | 2005-12-22 | 2015-10-28 | Newron Pharmaceuticals S.p.A. | 2-phenylethylamino derivatives as calcium and/or sodium channel modulators |
| PT2029524E (pt) | 2006-06-19 | 2015-03-09 | Newron Pharm Spa | Processo para a produção de 2-[4-(3- e 2-fluorobenziloxi benzilamino]propanamidas |
| FR2903985B1 (fr) | 2006-07-24 | 2008-09-05 | Sanofi Aventis Sa | Derives de n-(amino-heteroaryl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
| AU2008261325B2 (en) | 2007-06-15 | 2012-12-06 | Newron Pharmaceuticals S.P.A. | Substituted 2- [2- (phenyl) ethylamino] alkaneamide derivatives and their use as sodium and/or calcium channel modulators |
| CN104523668B (zh) * | 2007-12-11 | 2020-06-09 | 纽朗制药有限公司 | 高纯度的2-[4-(3-或2-氟苄氧基)苄氨基]丙酰胺类及其用途 |
| EP2314569A1 (en) | 2009-10-22 | 2011-04-27 | Merck Patent GmbH | Novel polymorphic forms of (S)-2-[4-(3-Fluoro-benzyloxy)-benzylamino]-propionamide mesylate salt and processes of manufacturing thereof |
| WO2011134763A1 (en) | 2010-04-27 | 2011-11-03 | Newron Pharmaceuticals S.P.A. | Process for the production of ralfinamide methanesulfonate salts or their r-enantiomers |
| WO2015102390A1 (ko) * | 2013-12-30 | 2015-07-09 | 이화여자대학교 산학협력단 | 신규한 아미드 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 포함하는 통증의 예방 또는 치료용 약학적 조성물 |
| CN107522654B (zh) * | 2016-06-21 | 2020-09-01 | 中国人民解放军军事医学科学院毒物药物研究所 | 新的α-氨基酰胺衍生物及其医药用途 |
| WO2019205147A1 (zh) * | 2018-04-28 | 2019-10-31 | 上海璃道医药科技有限公司 | 包含苯并含氧脂肪环结构的氨基乙酰胺类化合物及其用途 |
| CN112716927B (zh) * | 2020-10-12 | 2022-10-14 | 复旦大学 | α-氨基酰胺类化合物及其制备方法与应用 |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3658967A (en) | 1966-06-23 | 1972-04-25 | Ici Ltd | Carboxylic acid derivatives for lowering the concentration of triglycerides in the blood |
| GB1140748A (en) | 1966-06-23 | 1969-01-22 | Ici Ltd | New carboxylic acid derivatives |
| CH480308A (de) | 1966-08-11 | 1969-10-31 | Ciba Geigy | Verfahren zur Herstellung von Thiosemicarbazid-Verbindungen |
| US4049663A (en) | 1972-06-06 | 1977-09-20 | Allen & Hanburys Limited | Ethylene diamine derivatives |
| US4311853A (en) | 1979-02-06 | 1982-01-19 | The Radiochemical Centre Limited | Selenium derivatives of thyroxine and tri-iodothyronine |
| DE3010599A1 (de) | 1979-03-22 | 1980-10-09 | Continental Pharma | Derivate von glycinamid, deren herstellung und verwendung |
| US4267354A (en) | 1979-04-25 | 1981-05-12 | E. R. Squibb & Sons, Inc. | Substituted amides having antiinflammatory activity and intermediates |
| ZA805476B (en) | 1979-09-26 | 1981-11-25 | Robins Co Inc A H | 2-amino-3-benzoyl-phenylacetamides and cyclic homologues |
| FR2480747A1 (fr) | 1980-04-17 | 1981-10-23 | Roques Bernard | Derives d'acides amines et leur application therapeutique |
| DE3483308D1 (de) | 1983-11-21 | 1990-10-31 | Fujisawa Pharmaceutical Co | Semicarbazid-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen. |
| US4839369A (en) | 1985-04-16 | 1989-06-13 | Rorer Pharmaceutical Corporation | Aryl and heteroaryl ethers as agents for the treatment of hypersensitive ailments |
| US4631287A (en) | 1985-04-16 | 1986-12-23 | Usv Pharmaceutical Corp. | Aryl and heteroaryl ethers as agents for the treatment of hypersensitive ailments |
| US4725619A (en) | 1985-04-16 | 1988-02-16 | Usv Pharmaceutical Corporation | Aryl and heteroaryl ethers as agents for the treatment of hypersensitive ailments |
| GB8714901D0 (en) | 1986-07-23 | 1987-07-29 | Ici Plc | Amide derivatives |
| GB2216515A (en) | 1988-03-04 | 1989-10-11 | Nippon Shinyaku Co Ltd | Acylphenol derivatives |
| IL94466A (en) | 1989-05-25 | 1995-01-24 | Erba Carlo Spa | Pharmaceutical preparations containing the history of A-amino carboxamide N-phenylalkyl are converted into such new compounds and their preparation |
| DE3928488A1 (de) | 1989-08-29 | 1991-03-07 | Standard Elektrik Lorenz Ag | Interferometrisches messsystem |
| EP0525360B1 (en) | 1991-07-30 | 1998-03-25 | Korea Research Institute Of Chemical Technology | Novel phenylacetamide derivatives and processes for the preparation thereof |
| US5498610A (en) | 1992-11-06 | 1996-03-12 | Pfizer Inc. | Neuroprotective indolone and related derivatives |
| GB9306886D0 (en) | 1993-04-01 | 1993-05-26 | Erba Carlo Spa | Substituted (arylakoxybenzyl) aminopropanamide derivatives and process for their preparation |
| GB9306899D0 (en) | 1993-04-01 | 1993-05-26 | Erba Carlo Spa | Substituted (arylalkylaminobenzyl) aminopropionamide derivatives and process for their preparation |
| US5475007A (en) | 1993-05-28 | 1995-12-12 | The Regents Of The University Of California | 1,2,3,4-tetrahydroquinoline-2,3,4-trione-3 or 4-oximes and the use thereof |
| US5482964A (en) | 1994-10-11 | 1996-01-09 | Warner-Lambert Company | Substituted phenoxyhydroxypropyl amines as central nervous system agents |
| US5541204A (en) | 1994-12-02 | 1996-07-30 | Bristol-Myers Squibb Company | Aryloxypropanolamine β 3 adrenergic agonists |
| KR0147963B1 (ko) | 1995-01-10 | 1998-08-17 | 강박광 | 엔-아릴알킬페닐아세트아미드 유도체와 그의 제조방법 |
| US5849737A (en) | 1995-04-14 | 1998-12-15 | The Regents Of The University Of California | Compositions and methods for treating pain |
| US5741818A (en) | 1995-06-07 | 1998-04-21 | University Of Saskatchewan | Semicarbazones having CNS activity and pharmaceutical preparations containing same |
| GB9515411D0 (en) | 1995-07-27 | 1995-09-27 | Pharmacia Spa | N-(4-substituted-benzyl)-2-aminolactam derivatives |
| GB9515412D0 (en) * | 1995-07-27 | 1995-09-27 | Pharmacia Spa | 2-(4-substituted)-benzylamino-2-methyl-propanamide derivatives |
| US5688830A (en) | 1996-01-25 | 1997-11-18 | Syntex (U.S.A.) Inc. | Treatment of neuropathic pain |
| JP4160136B2 (ja) * | 1996-08-29 | 2008-10-01 | 武田薬品工業株式会社 | 縮合環状エーテル類、その製造法および剤 |
| TW492957B (en) | 1996-11-07 | 2002-07-01 | Novartis Ag | N-substituted 2-cyanopyrrolidnes |
| GB9625795D0 (en) | 1996-12-12 | 1997-01-29 | Smithkline Beecham Plc | Novel treatment |
| GB9706730D0 (en) | 1997-04-03 | 1997-05-21 | Pharmacia & Upjohn Spa | 2-[(3-substituted)-5-Isoxazolymethylaminojalkanamid derivatives |
| JP2001526648A (ja) | 1997-04-22 | 2001-12-18 | コセンシス・インコーポレイテッド | 炭素環及びヘテロ環で置換されたセミカルバゾン及びチオセミカルバゾン、及びその使用 |
| WO1999026614A1 (en) * | 1997-11-21 | 1999-06-03 | Euro-Celtique S.A. | Substituted 2-aminoacetamides and the use thereof |
| GB9727521D0 (en) | 1997-12-31 | 1998-02-25 | Pharmacia & Upjohn Spa | Substituted 2-benzylamino-2-phenyl-acetamide compounds |
| GB9727523D0 (en) | 1997-12-31 | 1998-02-25 | Pharmacia & Upjohn Spa | Alpha-aminoamide derivatives useful as analgesic agents |
| JP2002511387A (ja) * | 1998-02-04 | 2002-04-16 | ユーロ−セルティック エス． ア． | 置換セミカルバジドおよびその使用 |
| JP2000191533A (ja) * | 1998-10-19 | 2000-07-11 | Eisai Co Ltd | 鎮痛剤 |
| CN1148188C (zh) * | 1998-10-19 | 2004-05-05 | 卫材株式会社 | 镇痛剂 |
| US6281211B1 (en) | 1999-02-04 | 2001-08-28 | Euro-Celtique S.A. | Substituted semicarbazides and the use thereof |
| AR023171A1 (es) * | 1999-03-26 | 2002-09-04 | Cocensys Inc | Pirazoles, imidazoles, oxazoles, tiazoles, y pirroles sustituidos por arilo, y el uso de los mismos. |
| EP1169060B1 (en) | 1999-04-09 | 2005-08-31 | Euro-Celtique S.A. | Sodium channel blocker compositions and the use thereof |
| JP4350508B2 (ja) * | 2001-09-03 | 2009-10-21 | ニユーロン・フアーマシユーテイカルズ・エツセ・ピー・アー | ガバペンチンまたはその類似体とα−アミノアミドとを含む薬剤組成物およびその鎮痛用途 |
| AR044007A1 (es) | 2003-04-11 | 2005-08-24 | Newron Pharmaceuticals Inc | Metodos para el tratamiento de la enfermedad de parkinson |
| EP1588704A1 (en) | 2004-04-22 | 2005-10-26 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful in the treatment of restless legs syndrome and addictive disorders |
| BRPI0515154A (pt) | 2004-09-10 | 2008-07-08 | Newron Pharm Spa | uso de (halobenzilóxi)benzilamino-propanamidas para a fabricação de medicamentos ativos, compostos e composição farmacêutica |
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2003
- 2003-01-16 EP EP03000921A patent/EP1438956A1/en not_active Withdrawn
- 2003-11-18 DE DE60317935T patent/DE60317935T2/de not_active Expired - Lifetime
- 2003-11-18 MX MXPA05007339A patent/MXPA05007339A/es active IP Right Grant
- 2003-11-18 DK DK03772344T patent/DK1585510T3/da active
- 2003-11-18 PT PT03772344T patent/PT1585510E/pt unknown
- 2003-11-18 EP EP03772344A patent/EP1585510B1/en not_active Expired - Lifetime
- 2003-11-18 RU RU2005125919/15A patent/RU2336077C2/ru active
- 2003-11-18 AU AU2003279399A patent/AU2003279399B8/en not_active Expired
- 2003-11-18 JP JP2004565939A patent/JP4885455B2/ja not_active Expired - Lifetime
- 2003-11-18 AT AT03772344T patent/ATE380026T1/de active
- 2003-11-18 US US10/541,195 patent/US7709523B2/en active Active
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- 2003-11-18 WO PCT/EP2003/012889 patent/WO2004062655A1/en active IP Right Grant
- 2003-11-18 NZ NZ541117A patent/NZ541117A/en not_active IP Right Cessation
- 2003-11-18 KR KR1020057013090A patent/KR101049694B1/ko active IP Right Grant
- 2003-11-18 SI SI200331074T patent/SI1585510T1/sl unknown
- 2003-11-18 BR BRPI0317795A patent/BRPI0317795B8/pt active IP Right Grant
- 2003-11-18 CN CNB2003801088908A patent/CN100418517C/zh not_active Expired - Lifetime
- 2003-11-18 CA CA2510514A patent/CA2510514C/en not_active Expired - Lifetime
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| MK1K | Patent expired |