WO1990014089A1 - Nouvelles compositions a base d'imipramine - Google Patents
Nouvelles compositions a base d'imipramine Download PDFInfo
- Publication number
- WO1990014089A1 WO1990014089A1 PCT/FR1990/000359 FR9000359W WO9014089A1 WO 1990014089 A1 WO1990014089 A1 WO 1990014089A1 FR 9000359 W FR9000359 W FR 9000359W WO 9014089 A1 WO9014089 A1 WO 9014089A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cyclodextrin
- imipramine
- derivatives
- trimipramine
- new
- Prior art date
Links
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 229960004801 imipramine Drugs 0.000 title claims abstract description 12
- 239000000203 mixture Substances 0.000 title claims description 13
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 19
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 13
- ZSCDBOWYZJWBIY-UHFFFAOYSA-N trimipramine Chemical compound C1CC2=CC=CC=C2N(CC(CN(C)C)C)C2=CC=CC=C21 ZSCDBOWYZJWBIY-UHFFFAOYSA-N 0.000 claims description 12
- 229960002431 trimipramine Drugs 0.000 claims description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 6
- 239000001116 FEMA 4028 Substances 0.000 claims description 5
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 5
- 229960004853 betadex Drugs 0.000 claims description 5
- 235000019658 bitter taste Nutrition 0.000 claims description 3
- 239000008247 solid mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000019640 taste Nutrition 0.000 description 3
- 230000009967 tasteless effect Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- -1 flavorings Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940118176 surmontil Drugs 0.000 description 1
- 229940041597 tofranil Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- YDGHCKHAXOUQOS-BTJKTKAUSA-N trimipramine maleate Chemical compound [O-]C(=O)\C=C/C([O-])=O.C1CC2=CC=CC=C2[NH+](CC(C[NH+](C)C)C)C2=CC=CC=C21 YDGHCKHAXOUQOS-BTJKTKAUSA-N 0.000 description 1
Classifications
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
Definitions
- the present invention relates to a new pharmaceutical composition based on imipramine or one of its derivatives. It relates more particularly to a new solid pharmaceutical composition intended for the oral administration of imipramine or one of its derivatives.
- Ipramine is currently marketed under the brand TOFRANIL in the form of tablets or hydrochloride-based solutions.
- Trimipramine which is a derivative of imipramine is marketed under the brand name SURMONTIL in the form of tablets or solution, the tablets consist of trimi ⁇ pramine maleate while the solutions consist of methane sulfonate.
- aqueous solutions of imipramine or trimipramine have two drawbacks: on the one hand they have a very strong bitterness which makes their administration by the oral route hardly acceptable especially for children and the elderly, on the other hand the division of the aqueous forms is always a problem in outpatient treatment, especially for the elderly.
- These solutions also exhibit an astonishing phenomenon, when they are evaporated to dryness, the product obtained, initially crystallized, is in the form of a gum whose re-solution is impossible and which no longer allows any pharmaceutical formatting. .
- the nature of the transformation product after aqueous solution is unknown to date.
- This solution consists in including imipramine or its derivatives and its salts in the cyclodextrin.
- cyclo ⁇ dextrin per mole of imipramine, its derivatives or its salts. It is preferred to use between two and fifteen moles of cyclodextrin per mole of imipramine, its derivatives or its salts.
- Mimipramine derivatives include trimipramine and its salts include hydrochloride, methane sulfonate.
- the cyclodextrin used is chosen from a cyclodextrin, B cyclodextrin and ⁇ cyclodextrin. It is preferred to use ⁇ cyclodextrin.
- the process for including imipramine or its derivatives and its salts in the cyclodextrin consists in dissolving the imipramine, its derivative or its salt and the cyclodextrin in a small amount of water or solvent, to be mixed carefully mix the resulting mixture and evaporate said mixture.
- This evaporation can be carried out indifferently by lyophilization, without the need to add either diluent or binder, or by drying by any means such as for example the oven.
- the pulverulent composition obtained after evaporation can undergo pharmaceutical shaping such as bagging, compression or granulation. It is always possible before final shaping to add sweeteners, flavorings, sweetening agents, preservatives and coloring agents.
- pharmaceutical shaping such as bagging, compression or granulation. It is always possible before final shaping to add sweeteners, flavorings, sweetening agents, preservatives and coloring agents.
- sweeteners, flavorings, sweetening agents, preservatives and coloring agents in the context of the present invention we prefer a formatting in ready-to-use sachets which have the advantages of an easy oral intake especially in children and an advantageous unitary distribution for the child as for the elderly.
- compositions after redissolving have a tasteless taste and a presentation that is entirely acceptable to the consumer.
- trimipramine methane sulfonate 6 64 g 3.38 g 1.66 g ⁇ cyclodextrin 50.00 g 50.00 g 50.00 g water 26.90 g 26.71 g 26.80 g cyclodextrin molar ratio --- 2, 6 5.2 10.4 trimipramine
- trimipramine methane sulfonate is dissolved in water, the cyclodextrin is wetted with the preceding solution. Mixed with magnetic stirring for two hours at room temperature.
- the mixture is divided into 1.6 ml cells at a rate of 1.67 g
- Another test is carried out in which the dough is placed in a crystallizer and the whole is placed in a heated desiccator at
- Example 1 is reproduced according to the first composition indicated, but in the absence of cyclodextrin, that is to say that 6.64 g of trimipramine methane sulfonate are put in 26.9 ml of water and the solution obtained is dried. . A mass is obtained in the form of a gum which cannot be dissolved in water.
- trimipramine methane sulfonate 0.44 g ⁇ cyclodextrin 6.20 g water 2.50 g isopropanol 2.50 g
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nanotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Materials For Medical Uses (AREA)
- Filtering Materials (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8906781A FR2647343B1 (fr) | 1989-05-24 | 1989-05-24 | Nouvelle forme pharmaceutique poreuse et sa preparation |
| FR89/06781 | 1989-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1990014089A1 true WO1990014089A1 (fr) | 1990-11-29 |
Family
ID=9381955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FR1990/000359 WO1990014089A1 (fr) | 1989-05-24 | 1990-05-22 | Nouvelles compositions a base d'imipramine |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5244881A (forum.php) |
| EP (2) | EP0399902B1 (forum.php) |
| JP (1) | JP2948271B2 (forum.php) |
| KR (1) | KR0163423B1 (forum.php) |
| AT (2) | ATE83663T1 (forum.php) |
| AU (2) | AU631888B2 (forum.php) |
| CA (2) | CA2017360A1 (forum.php) |
| DD (1) | DD297915A5 (forum.php) |
| DE (2) | DE69000641T2 (forum.php) |
| DK (2) | DK0399902T3 (forum.php) |
| ES (2) | ES2054289T3 (forum.php) |
| FI (1) | FI103712B1 (forum.php) |
| FR (1) | FR2647343B1 (forum.php) |
| GR (1) | GR3006655T3 (forum.php) |
| IE (2) | IE64370B1 (forum.php) |
| IL (2) | IL94460A0 (forum.php) |
| NO (1) | NO180517C (forum.php) |
| NZ (2) | NZ233766A (forum.php) |
| PL (1) | PL285327A1 (forum.php) |
| PT (2) | PT94139B (forum.php) |
| TW (1) | TW257672B (forum.php) |
| WO (1) | WO1990014089A1 (forum.php) |
| YU (1) | YU100790A (forum.php) |
| ZA (2) | ZA903895B (forum.php) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004017949A3 (de) * | 2002-08-23 | 2004-04-29 | Erich Gulbins | Prophylaxe und therapie von infektionserkrankungen mit amitryptilin oder imipramin oder desipramin oder fgf oder einem anticeramid antikörper oder cyclodextrin oder nystatin oder filipin |
| RU2609198C1 (ru) * | 2016-01-25 | 2017-01-30 | Закрытое Акционерное Общество "БИОКОМ" | Твердая лекарственная форма имипрамина немедленного высвобождения и способ ее получения |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69231457T2 (de) * | 1991-06-21 | 2001-05-23 | Takeda Chemical Industries Ltd | Zyklodextrin-Zusammensetzung enthaltend Fumagillol-Derivate |
| KR100256147B1 (ko) | 1991-12-24 | 2000-08-01 | 오노다 마사요시 | 구강내 붕해성 제제 및 이의 제조방법 |
| GB9318880D0 (en) * | 1993-09-11 | 1993-10-27 | Smithkline Beecham Plc | Pharmaceutical composition |
| CA2190598A1 (en) * | 1994-05-27 | 1995-12-07 | Lawrence John Penkler | Pharmaceutical composition |
| US6471992B1 (en) * | 1997-02-20 | 2002-10-29 | Therics, Inc. | Dosage form exhibiting rapid disperse properties, methods of use and process for the manufacture of same |
| BE1011251A3 (fr) * | 1997-07-03 | 1999-06-01 | Ucb Sa | Compositions pharmaceutiques administrables par voie orale, comprenant une substance active et une cyclodextrine. |
| TW527195B (en) | 1997-10-09 | 2003-04-11 | Ssp Co Ltd | Fast-soluble solid pharmaceutical combinations |
| JP4644364B2 (ja) * | 1998-02-05 | 2011-03-02 | ノバルティス アーゲー | エポシロン組成物 |
| IT1304190B1 (it) * | 1998-12-18 | 2001-03-08 | Euphar Group Srl | Clatrati di deidroepiandrosterone e relative composizionifarmaceutiche |
| US6287603B1 (en) * | 1999-09-16 | 2001-09-11 | Nestec S.A. | Cyclodextrin flavor delivery systems |
| PL212123B1 (pl) | 2002-01-15 | 2012-08-31 | Ucb Farchim Sa | Doustna kompozycja farmaceutyczna |
| US7759506B2 (en) | 2002-02-25 | 2010-07-20 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
| HUP0500134A3 (en) | 2002-02-25 | 2009-12-28 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
| DE10248314A1 (de) * | 2002-10-16 | 2004-04-29 | Dr. Suwelack Skin & Health Care Ag | Verwendung von Formkörpern zur äußeren Anwendung |
| FR2876910B1 (fr) * | 2004-10-21 | 2007-04-13 | Pierre Fabre Medicament Sa | Complexe comprenant la mequitazine, une cyclodextrine et un agent d'interaction |
| NZ561664A (en) | 2005-02-24 | 2011-02-25 | Diffusion Pharmaceuticals Llc | Trans carotenoids, their synthesis, formulation and uses |
| DE102005041860A1 (de) * | 2005-09-02 | 2007-03-08 | Schering Ag | Nanopartikulärer Einschluss- und Ladungskomplex für pharmazeutische Formulierungen |
| US8293804B2 (en) | 2007-04-13 | 2012-10-23 | Diffusion Pharmaceuticals Llc | Use of bipolar trans carotenoids as a pretreatment and in the treatment of peripheral vascular disease |
| JP2009091309A (ja) * | 2007-10-10 | 2009-04-30 | Japan Organo Co Ltd | バコパモニエラエキスを含有する組成物およびその製造方法ならびに飲食品 |
| EA201070544A1 (ru) | 2007-10-31 | 2010-12-30 | Диффьюжн Фармасьютикалз Ллс | Новый класс терапевтических веществ, усиливающих диффузию низкомолекулярных соединений |
| BRPI0918906A2 (pt) * | 2008-09-05 | 2015-12-01 | Mcneil Ppc Inc | método para a produção de comprimidos de cetirizina |
| US10130689B2 (en) | 2009-06-22 | 2018-11-20 | Diffusion Pharmaceuticals Llc | Diffusion enhancing compounds and their use alone or with thrombolytics |
| US8974822B2 (en) | 2010-06-02 | 2015-03-10 | Diffusion Pharmaceuticals Llc | Oral formulations of bipolar trans carotenoids |
| WO2012037117A1 (en) * | 2010-09-13 | 2012-03-22 | Bev-Rx, Inc. | Aqueous drug delivery system comprising off - flavor masking agent |
| JP7032320B2 (ja) | 2016-03-24 | 2022-03-08 | ディフュージョン・ファーマシューティカルズ・エルエルシー | 癌を処置するための、化学療法及び放射線療法を伴う二極性トランスカロテノイドの使用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5443570B2 (forum.php) * | 1972-10-27 | 1979-12-20 | ||
| IE45770B1 (en) * | 1976-10-06 | 1982-11-17 | Wyeth John & Brother Ltd | Pharmaceutical dosage forms |
| US4165382A (en) * | 1977-10-17 | 1979-08-21 | Jose Pozuelo | Method of pharmacologically treating schizophrenia with alpha-methyl-para-tyrosine |
| US4284555A (en) * | 1979-04-27 | 1981-08-18 | Schering Corporation | 7-Chloro-8(substituted amino carbonyloxy)-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines |
| US4349472A (en) * | 1979-04-27 | 1982-09-14 | Schering Corporation | (S)-8(1-Adamantanecarbonyloxy)-7-chloro-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine |
| US4477378A (en) * | 1980-02-05 | 1984-10-16 | Schering Corp. | Esters of substituted 8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines |
| WO1986003198A1 (en) * | 1984-11-27 | 1986-06-05 | Dainippon Pharmaceutical Co., Ltd. | 2-(1-piperazinyl)-4-substituted phenylquinoline derivatives, process for their preparation, and medicinal composition containing same |
| GB8506792D0 (en) * | 1985-03-15 | 1985-04-17 | Janssen Pharmaceutica Nv | Derivatives of y-cyclodextrin |
| GB8613688D0 (en) * | 1986-06-05 | 1986-07-09 | Euro Celtique Sa | Pharmaceutical composition |
-
1989
- 1989-05-24 FR FR8906781A patent/FR2647343B1/fr not_active Expired - Fee Related
-
1990
- 1990-05-21 ZA ZA903895A patent/ZA903895B/xx unknown
- 1990-05-21 IE IE182190A patent/IE64370B1/en not_active IP Right Cessation
- 1990-05-21 IL IL94460A patent/IL94460A0/xx unknown
- 1990-05-21 IL IL9445990A patent/IL94459A/en not_active IP Right Cessation
- 1990-05-22 EP EP90401369A patent/EP0399902B1/fr not_active Expired - Lifetime
- 1990-05-22 DE DE9090401370T patent/DE69000641T2/de not_active Expired - Fee Related
- 1990-05-22 AU AU57433/90A patent/AU631888B2/en not_active Ceased
- 1990-05-22 ES ES90401370T patent/ES2054289T3/es not_active Expired - Lifetime
- 1990-05-22 AT AT90401370T patent/ATE83663T1/de not_active IP Right Cessation
- 1990-05-22 US US07/776,344 patent/US5244881A/en not_active Expired - Fee Related
- 1990-05-22 DK DK90401369.5T patent/DK0399902T3/da active
- 1990-05-22 DE DE90401369T patent/DE69005359T2/de not_active Expired - Lifetime
- 1990-05-22 DK DK90401370.3T patent/DK0399903T3/da active
- 1990-05-22 ES ES90401369T patent/ES2062437T3/es not_active Expired - Lifetime
- 1990-05-22 NZ NZ233766A patent/NZ233766A/xx unknown
- 1990-05-22 AT AT90401369T patent/ATE98867T1/de not_active IP Right Cessation
- 1990-05-22 AU AU55828/90A patent/AU623779B2/en not_active Ceased
- 1990-05-22 WO PCT/FR1990/000359 patent/WO1990014089A1/fr unknown
- 1990-05-22 KR KR1019900007369A patent/KR0163423B1/ko not_active Expired - Fee Related
- 1990-05-22 EP EP90401370A patent/EP0399903B1/fr not_active Expired - Lifetime
- 1990-05-23 ZA ZA903978A patent/ZA903978B/xx unknown
- 1990-05-23 CA CA002017360A patent/CA2017360A1/fr not_active Abandoned
- 1990-05-23 NO NO902280A patent/NO180517C/no unknown
- 1990-05-23 DD DD90340952A patent/DD297915A5/de not_active IP Right Cessation
- 1990-05-23 PT PT94139A patent/PT94139B/pt not_active IP Right Cessation
- 1990-05-23 YU YU01007/90A patent/YU100790A/xx unknown
- 1990-05-23 CA CA002017355A patent/CA2017355A1/fr not_active Abandoned
- 1990-05-23 IE IE186290A patent/IE63317B1/en not_active IP Right Cessation
- 1990-05-23 JP JP2131437A patent/JP2948271B2/ja not_active Expired - Lifetime
- 1990-05-23 FI FI902553A patent/FI103712B1/fi not_active IP Right Cessation
- 1990-05-23 NZ NZ233784A patent/NZ233784A/xx unknown
- 1990-05-23 PT PT94138A patent/PT94138B/pt not_active IP Right Cessation
- 1990-05-24 PL PL28532790A patent/PL285327A1/xx unknown
- 1990-05-30 TW TW079104379A patent/TW257672B/zh active
-
1992
- 1992-12-24 GR GR920401770T patent/GR3006655T3/el unknown
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| STN INTERNATIONAL INFORMATION SERVICES, Database, Chemical Abstracts, Access. Number 108(14):118829d, C. BARBERO et al., "Thermodynamic Study of Interactions Between Cyclohepta-Amylose and Dibenzazepines in Aqueous Solution"; & AN. QUIM. SER. A, 83(3), 285-9. * |
| STN INTERNATIONAL INFORMATION SERVICES, Database, Chemical Abstracts, Access. Number 111(21):194557r, T. HOSHINO et al., "Change in Photochemical Reaction of Clomipramine by Inclusion Complexations of .beta.- and dimethyl-.beta.-Cyclodextrins"; & YAKUGAKU ZASSHI, 109(2), 107-12, 1989. * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004017949A3 (de) * | 2002-08-23 | 2004-04-29 | Erich Gulbins | Prophylaxe und therapie von infektionserkrankungen mit amitryptilin oder imipramin oder desipramin oder fgf oder einem anticeramid antikörper oder cyclodextrin oder nystatin oder filipin |
| US7812015B2 (en) | 2002-08-23 | 2010-10-12 | Erich Gülbins | Prophylaxis and treatment of infectious diseases |
| RU2609198C1 (ru) * | 2016-01-25 | 2017-01-30 | Закрытое Акционерное Общество "БИОКОМ" | Твердая лекарственная форма имипрамина немедленного высвобождения и способ ее получения |
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