EA011290B1 - Препаративные формы пероральных лекарственных форм мемантина с немедленным высвобождением - Google Patents
Препаративные формы пероральных лекарственных форм мемантина с немедленным высвобождением Download PDFInfo
- Publication number
- EA011290B1 EA011290B1 EA200700055A EA200700055A EA011290B1 EA 011290 B1 EA011290 B1 EA 011290B1 EA 200700055 A EA200700055 A EA 200700055A EA 200700055 A EA200700055 A EA 200700055A EA 011290 B1 EA011290 B1 EA 011290B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- dosage form
- immediate release
- oral dosage
- memantine
- solid oral
- Prior art date
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
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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
- A61K31/13—Amines
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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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58124404P | 2004-06-17 | 2004-06-17 | |
| PCT/US2005/021284 WO2006096194A2 (en) | 2004-06-17 | 2005-06-16 | Drinkable immediate release tablet made with direct compression of memantine or neramexane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200700055A1 EA200700055A1 (ru) | 2007-10-26 |
| EA011290B1 true EA011290B1 (ru) | 2009-02-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200700055A EA011290B1 (ru) | 2004-06-17 | 2005-06-16 | Препаративные формы пероральных лекарственных форм мемантина с немедленным высвобождением |
Country Status (11)
| Country | Link |
|---|---|
| EP (3) | EP2601937A1 (enExample) |
| JP (1) | JP5025468B2 (enExample) |
| KR (1) | KR20090033410A (enExample) |
| CN (1) | CN101389315A (enExample) |
| AU (1) | AU2005328701B2 (enExample) |
| BR (1) | BRPI0512263A (enExample) |
| CA (1) | CA2568445C (enExample) |
| EA (1) | EA011290B1 (enExample) |
| ES (1) | ES2483126T3 (enExample) |
| IL (1) | IL179992A (enExample) |
| WO (1) | WO2006096194A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2203163B1 (en) * | 2007-09-12 | 2014-08-27 | Merz Pharma GmbH & Co. KGaA | Titration package for neramexane and its use in the treatment of an inner ear disorder |
| CA2765609A1 (en) * | 2009-06-29 | 2011-01-06 | Merz Pharma Gmbh & Co. Kgaa | Method of preparing neramexane |
| DK2448910T3 (da) * | 2009-06-29 | 2013-06-03 | Merz Pharma Gmbh & Co Kgaa | Fremgangsmåde til fremstilling af neramexan |
| PL2448909T3 (pl) * | 2009-06-29 | 2013-09-30 | Merz Pharma Gmbh & Co Kgaa | Sposób wytwarzania 1-amino-1,3,3,5,5-pentametylocykloheksanu |
| EP2316434A1 (en) * | 2009-10-22 | 2011-05-04 | Abdi Ibrahim Ilac Sanayi Ve Ticaret Anonim Sirketi | Orally disintegrating tablets of memantine |
| US20110294890A1 (en) * | 2010-05-28 | 2011-12-01 | Merz Pharma Gmbh & Co. Kgaa | Neramexane for the treatment or prevention of inner ear disorders |
| US8980318B2 (en) * | 2010-06-24 | 2015-03-17 | Merz Pharma Gmbh & Co. Kgaa | Neramexane multiple unit dosage form |
| MX2013004123A (es) | 2010-10-12 | 2013-12-16 | Univ Johns Hopkins | Composiciones antitusigenas que comprenden memantina. |
| WO2012048871A1 (en) | 2010-10-12 | 2012-04-19 | Merz Pharma Gmbh & Co. Kgaa | Memantine for improving cognitive performance in subjects |
| EP2526925A1 (en) | 2011-05-23 | 2012-11-28 | Deva Holding Anonim Sirketi | A dose adjustable oral pump spray or aerosol spray containing memantine |
| CN107334744B (zh) * | 2017-07-24 | 2020-09-04 | 湖南洞庭药业股份有限公司 | 盐酸美金刚药物组合物和制法 |
| EP4238555A3 (en) * | 2019-05-31 | 2023-09-20 | Tecnimede, Sociedade Técnico-Medicinal, SA | Immediate release fixed-dose combination of memantine and donepezil |
| CN114199812A (zh) * | 2021-12-28 | 2022-03-18 | 南通联亚药业有限公司 | 一种盐酸美金刚缓释制剂中盐酸美金刚的检测方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4346112A (en) * | 1981-06-29 | 1982-08-24 | University Patents Inc. | Composition and method for treating patients having Parkinson's Disease |
| US5382601A (en) * | 1992-08-04 | 1995-01-17 | Merz + Co. Gmbh & Co. | Memantine-containing solid pharmaceutical dosage forms having an extended two-stage release profile and production thereof |
| WO1997014415A1 (en) * | 1995-10-19 | 1997-04-24 | F.H. Faulding & Co. Limited | Analgesic immediate and controlled release pharmaceutical composition |
| RU2189226C2 (ru) * | 1995-08-18 | 2002-09-20 | Ар.Пи.Шерер Лимитед | Оральные быстрорастворяющиеся композиции агонистов дофамина |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7305644A (enExample) | 1972-04-20 | 1973-10-23 | ||
| DE2856393C2 (de) | 1978-12-27 | 1983-04-28 | Merz + Co GmbH & Co, 6000 Frankfurt | Arzneimittel zur Behandlung von Morbus Parkinson |
| JPS6216413A (ja) * | 1985-07-12 | 1987-01-24 | Teijin Ltd | キチン類誘導体を用いた徐放性医薬品組成物 |
| US5506231A (en) | 1989-03-31 | 1996-04-09 | The Children's Medical Center Corporation | Treatment of aids dementia, myelopathy and blindness |
| US5334618A (en) | 1991-04-04 | 1994-08-02 | The Children's Medical Center Corporation | Method of preventing NMDA receptor-mediated neuronal damage |
| DE58905637D1 (de) | 1989-04-14 | 1993-10-21 | Merz & Co Gmbh & Co | Verwendung von Adamantan-Derivaten zur Prävention und Behandlung der cerebralen Ischämie. |
| DE4014672A1 (de) * | 1990-05-08 | 1991-11-14 | Werner E G Prof Dr Mueller | Verwendung von adamantan-derivaten zur zytoprotektion von nicht-infizierten und virus-infizierten lymphozyten als auch anderen zelltypen |
| US5614560A (en) | 1991-04-04 | 1997-03-25 | Children's Medical Center Corporation | Method of preventing NMDA receptor-mediated neuronal damage |
| US5455279A (en) | 1991-04-19 | 1995-10-03 | The Children's Medical Center Corporation | Regimen method of mediating neuronal damage using nitroglycerine |
| EP0581856B1 (en) | 1991-04-19 | 1999-07-14 | The Children's Medical Center Corporation | Method of preventing nmda receptor complex-mediated neuronal damage |
| JPH0971523A (ja) * | 1995-09-07 | 1997-03-18 | Riyuukakusan:Kk | 口腔内で崩壊性の速い錠剤 |
| JP3963488B2 (ja) * | 1997-06-30 | 2007-08-22 | メルツ ファーマ ゲゼルシャフト ミット ベシュレンクテル ハフツンク ウント コンパニー コマンディゲゼルシャフト アウフ アクチェン | １−アミノ−アルキルシクロヘキサンｎｍｄａ受容体拮抗薬 |
| US6071966A (en) | 1997-06-30 | 2000-06-06 | Merz + Co. Gmbh & Co. | 1-amino-alkylcyclohexane NMDA receptor antagonists |
| US6413556B1 (en) | 1999-01-08 | 2002-07-02 | Sky High, Llc | Aqueous anti-apoptotic compositions |
| SE9901077D0 (sv) | 1999-03-23 | 1999-03-23 | Astra Ab | Novel use |
| US6444702B1 (en) | 2000-02-22 | 2002-09-03 | Neuromolecular, Inc. | Aminoadamantane derivatives as therapeutic agents |
| TW593223B (en) * | 2000-06-20 | 2004-06-21 | Merz Pharma Gmbh & Co Kgaa | 1-amino-alkylcyclohexanes as 5-HT3 and neuronal nicotinic receptor antagonists |
| US6828462B2 (en) * | 2001-11-07 | 2004-12-07 | Merz Pharma Gmbh & Co. Kgaa | Unsaturated 1-amino-alkylcyclohexane NMDA, 5HT3, and neuronal nicotinic receptor antagonists |
| CA2473536A1 (en) * | 2002-01-16 | 2003-07-31 | Endo Pharmaceuticals, Inc. | Pharmaceutical composition and method for treating disorders of the central nervous system |
| TW200306189A (en) | 2002-03-21 | 2003-11-16 | Merz Pharma Gmbh & Co Kgaa | Azabicyclic, azatricyclic and azaspirocyclic derivatives of aminocyclohexane NMDA, 5HT3, and neuronal nicotinic receptor antagonists |
| FR2841138B1 (fr) * | 2002-06-25 | 2005-02-25 | Cll Pharma | Composition pharmaceutique solide contenant un principe actif lipophile, son procede de preparation |
| US20040127541A1 (en) * | 2002-07-31 | 2004-07-01 | Janet Codd | Bicifadine formulation |
| AU2004249151A1 (en) * | 2003-06-16 | 2004-12-29 | Allergan, Inc. | Memantine oral dosage forms |
| AR046314A1 (es) * | 2003-11-05 | 2005-11-30 | Merz Pharma Gmbh & Co Kgaa | Composiciones que comprenden ciclohexilaminas y aminoadamantanos |
| NZ548351A (en) * | 2004-01-20 | 2009-08-28 | Novartis Ag | Direct compression formulation and process |
| CA2554959A1 (en) * | 2004-01-29 | 2005-08-11 | Neuromolecular, Inc. | Combination of a nmda receptor antagonist and a mao-inhibitor or a gadpf-inhibitor for the treatment of central nervous system-related conditions |
| GT200600008A (es) * | 2005-01-18 | 2006-08-09 | Formulacion de compresion directa y proceso |
-
2005
- 2005-06-16 CA CA2568445A patent/CA2568445C/en not_active Expired - Fee Related
- 2005-06-16 EP EP13153135.2A patent/EP2601937A1/en not_active Withdrawn
- 2005-06-16 BR BRPI0512263-5A patent/BRPI0512263A/pt not_active IP Right Cessation
- 2005-06-16 EA EA200700055A patent/EA011290B1/ru not_active IP Right Cessation
- 2005-06-16 CN CNA2005800198789A patent/CN101389315A/zh active Pending
- 2005-06-16 AU AU2005328701A patent/AU2005328701B2/en not_active Ceased
- 2005-06-16 WO PCT/US2005/021284 patent/WO2006096194A2/en not_active Ceased
- 2005-06-16 KR KR1020097005872A patent/KR20090033410A/ko not_active Withdrawn
- 2005-06-16 JP JP2007516731A patent/JP5025468B2/ja not_active Expired - Lifetime
- 2005-06-16 EP EP05857458A patent/EP1765287A2/en not_active Withdrawn
- 2005-06-16 ES ES11179637.1T patent/ES2483126T3/es not_active Expired - Lifetime
- 2005-06-16 EP EP11179637.1A patent/EP2397122B1/en not_active Expired - Lifetime
-
2006
- 2006-12-11 IL IL179992A patent/IL179992A/en not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4346112A (en) * | 1981-06-29 | 1982-08-24 | University Patents Inc. | Composition and method for treating patients having Parkinson's Disease |
| US5382601A (en) * | 1992-08-04 | 1995-01-17 | Merz + Co. Gmbh & Co. | Memantine-containing solid pharmaceutical dosage forms having an extended two-stage release profile and production thereof |
| RU2189226C2 (ru) * | 1995-08-18 | 2002-09-20 | Ар.Пи.Шерер Лимитед | Оральные быстрорастворяющиеся композиции агонистов дофамина |
| WO1997014415A1 (en) * | 1995-10-19 | 1997-04-24 | F.H. Faulding & Co. Limited | Analgesic immediate and controlled release pharmaceutical composition |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006096194A8 (en) | 2007-01-11 |
| CN101389315A (zh) | 2009-03-18 |
| AU2005328701B2 (en) | 2009-08-13 |
| WO2006096194A2 (en) | 2006-09-14 |
| BRPI0512263A (pt) | 2008-02-26 |
| IL179992A (en) | 2012-02-29 |
| ES2483126T3 (es) | 2014-08-05 |
| EP2397122B1 (en) | 2014-05-14 |
| EP1765287A2 (en) | 2007-03-28 |
| WO2006096194A3 (en) | 2007-11-22 |
| KR20090033410A (ko) | 2009-04-02 |
| EP2601937A1 (en) | 2013-06-12 |
| IL179992A0 (en) | 2007-05-15 |
| EA200700055A1 (ru) | 2007-10-26 |
| JP5025468B2 (ja) | 2012-09-12 |
| JP2008509089A (ja) | 2008-03-27 |
| EP2397122A3 (en) | 2012-01-25 |
| AU2005328701A1 (en) | 2006-09-14 |
| EP2397122A2 (en) | 2011-12-21 |
| CA2568445C (en) | 2011-05-24 |
| CA2568445A1 (en) | 2006-09-14 |
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