EP0927026A1 - Pharmaceutical compositions containing amisulpride and their therapeutic applications - Google Patents
Pharmaceutical compositions containing amisulpride and their therapeutic applicationsInfo
- Publication number
- EP0927026A1 EP0927026A1 EP97919108A EP97919108A EP0927026A1 EP 0927026 A1 EP0927026 A1 EP 0927026A1 EP 97919108 A EP97919108 A EP 97919108A EP 97919108 A EP97919108 A EP 97919108A EP 0927026 A1 EP0927026 A1 EP 0927026A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- amisulpride
- isomers
- levorotatory
- composition according
- dextrorotatory
- 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.)
- Withdrawn
Links
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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
-
- 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
Definitions
- the present invention relates to new pharmaceutical compositions, mainly intended for oral administration, comprising 4 -am ⁇ no-N- [(1-ethylpyrrol ⁇ dm- 2-yl) methyl] -5- (ethylsulfonyl) -2- methoxybenzam ⁇ de or amisulpnde, its isomers and some of their derivatives, these compositions having improved bioavailability.
- Amisulpnde its isomers and some of their derivatives are described in French patent 78,01632, the teaching of which is fully incorporated in the present description.
- Amisulpride is an antipsychotic used in the treatment of psychoses, particularly in the treatment of paranoid and productive schizophrenia, psychoses acute delusions as well as in the treatment of deficiency states of schizophrenia, residual psychotic changes and states of 1 inhibition with slowdown. Amisulpnde is also useful in the treatment of dysthymia.
- Amisulpnde can be administered orally, generally in the form of tablets, dosed at 50 or 200 mg each (see Vidal, section Solian, pages 1463 and 1464, ed. Du Vidal, 1996).
- the daily doses of amisulpride thus administered are often very high and can exceed 1 g / day.
- patients treated with amisulpnde should take several of these tablets daily.
- some of these patients by reason of their condition, may find it difficult to regularly absorb, without forgetting, a high number of tablets and therefore to follow their treatment correctly.
- the plaintiff sought to develop a new form of amisulpnde, intended mainly for oral administration, requiring only a limited number of daily doses (or number of doses / day), or even a single daily dose.
- Tablets comprising a higher dose of amisulpnde, for example doses greater than 600 mg, were first considered. However, such tablets have been found to be too large to be easily swallowed by patients.
- the Applicant has been able to observe that the limited biodispombility (of the order of 35 to 45%) of 1 amisulpnde administered orally could be attributed to a partial and irregular passage of this compound at the gastrointestinal level and, thus, its passage to the cerebral level could sometimes be insufficient.
- the main object of the invention is therefore new forms of amisulpnde with improved bioavailability, in particular when they are administered orally.
- the invention consists of new pharmaceutical compositions, mainly intended for oral administration, characterized in that they comprise a lipophilic phase and at least one active principle consisting of 1 amisulpnde, one of its levorotatory isomers and dextrorotatory or a derivative of 1 amisulpnde or one of its levorotatory and dextrorotatory isomers, this derivative being chosen from an addition salt with a pharmacologically acceptable acid, a quaternary ammonium salt or an oxide, 1 amisulpride or one of its levorotatory and dextrorotatory isomers.
- active principle consisting of 1 amisulpnde, one of its levorotatory isomers and dextrorotatory or a derivative of 1 amisulpnde or one of its levorotatory and dextrorotatory isomers, this derivative being chosen from an addition salt with a pharmacologically acceptable acid, a quaternary ammonium salt or an oxide, 1 amisulpride or
- FIG. 1 represents the plasma concentrations of amisulpride measured in the rat after absorption of various formulations comprising the same dose of amisulprid.
- FIG. 2 represents the plasma concentrations of amisulpride measured in the rat after absorption of formulations comprising variable doses of amisulpride.
- said active ingredient is dissolved, partially or completely, in the lipophilic phase.
- a composition according to the invention is very particularly suitable for 1 amisulpride per se, ie 4 -amino-N- [(1-ethylpyrrolidin-2-yl) methyl] -5- (ethylsulfonyl) - 2-methoxybenzamide , its levogyre isomers
- a preferred tartrate consists of the compound described in Example IV of patent FR 78 01632, that is to say the (D) -tartrate of (S) - (, -) - amisulpride, in other words the [S- (R *, R *)] -2,3-dihydroxybutaned ⁇ oate du (S) - (-) -4-amino- N- [(1-ethylpyrrolidin-2-yl) methyl] -5- (ethylsulfonyl) -2-methoxybenzamide.
- a composition according to the invention may also be suitable for the other derivatives mentioned above. These derivatives and their process of obtaining, are described in more detail in the French patent 78,01632, already cited.
- acids suitable for forming salts of 1 • amisulpride per se and of its isomers mention may more particularly be made of hydrochloric, bromhydric, sulfunic, phosphoric, oxalic, acetic, tart ⁇ que, citric, methane-sulphonic acids.
- amisulpride will be understood to mean both amisulpride per se and its isomers and derivatives mentioned above.
- compositions according to the invention make it possible to significantly increase the bioavailability of 1 amisulpnde compared to the oral forms known hitherto.
- bioavailability means the fraction of the active principle which is absorbed from its pharmaceutical form and which reaches the site of action.
- a pharmaceutical composition according to the invention can comprise from 25 to 300 mg, more generally from 100 to 250 mg of amisulp ⁇ de / unit dose. Such a content authorizes the administration of one to three unit doses per day only, preferably one to two unit doses per day.
- the concentration of amisulpride in a composition pharmaceutical of the invention can be between 1 mg / ml and 350 mg / ml, preferably between 10 mg / ml and 310 mg / ml.
- the lipophilic phase can be solid or, preferably, liquid at room temperature.
- the lipophilic phase may consist of (i) one or more fatty acids, (ii) one or more monoglycerides or acetylated or polyethoxylated derivatives of monoglycerides, (iii) one or more diglycerides or acetylated or polyethoxylated derivatives of diglycerides, (iv) one or more several oils, such as mineral, animal, vegetable, transesterified and / or polyethoxylated or synthetic oils or (v) a mixture comprising two or more of the compounds mentioned under points (i), (ii), (iii) and (iv ), in particular, a mixture comprising a fatty acid and an oil.
- fatty acids of those comprising from 12 to 22 carbon atoms, in particular oleic, arachidonic, linolenic, linoleic or ricinoleic acids.
- monoglycerides diglycerides or acetylated or polyethoxylated derivatives of these compounds, mention may in particular be made of those comprising, respectively) one or two fatty chains comprising from 12 to 24 carbon atoms, and more particularly, those marketed by the companies Abitec and Eastman under the brands Capmul ® and Myvacet ® , in particular mono glycerol caprylate, mono glycerol stearate, monoacetylated monoglycerides and diacetylated monoglycerides.
- mineral oils suitable in the context of the invention there may be mentioned paraffin oils and petrolatum oil.
- vegetable oils mention may be made of olive, peanut, soybean, rapeseed, palm, sesame, grape seed, corn, walnut or sunflower oils.
- vegetable oils transesterified and / or polyethoxylated include polyethoxylated olive oils, sunflower polyethoxylated, palm polyethoxylated or polyethoxylated castor, including those sold under the trademark Labrafil ® by Gattefossé.
- liver oils in particular cod or halibut liver oils.
- synthetic oils mention may be made of silicone oils.
- Oleic acid constitutes a particularly preferred lipophilic phase.
- the lipophilic phase can be in the form of either an emulsion or a self-emulsifiable mixture.
- Such an emulsion in addition to the lipophilic phase, comprises a hydrophilic phase and, generally, at least one surfactant.
- the emulsion can be of the water in oil (W / O) type or, preferably, oil in water (O / W).
- the emulsion can be of the submicron emulsion type.
- Such an emulsion has a discontinuous phase in the form of particles with an average diameter of less than 1 ⁇ m, generally between 0.3 and 0.7 ⁇ m.
- the emulsion can also be of the microemulsion type, for which the discontinuous phase is generally in the form of particles with an average diameter of between 0.05 and 0.250 ⁇ m.
- the hydrophilic phase can consist of one or more compounds chosen from alcohols such as glycerol, propylene glycol, polyethylene glycols whose weight molecular is between 100 and 3000, or water. This is preferred in the context of the present invention.
- the dispersed phase of an emulsion according to the invention can represent from 5 to 30% by weight, generally from 10 to 20% by weight of the total weight of the emulsion.
- the surfactant is chosen according to the nature of the emulsion. Those skilled in the art know, in particular according to their HLB (Hydrophilic-Lipophilic Balance), which surfactant to choose to obtain a W / O, O / W emulsion or a micro-emulsion.
- HLB Hydrophilic-Lipophilic Balance
- surfactant which may be suitable in the context of the present invention include sorbitan esters and polyoxyethylene sorbitan esters such as those sold under the T een ® and Span ®, the lécithmes of animal or vegetable origin, castor oil polyoxyethylene, such as those sold under the Cremophor ® brand, sucrose fatty acid esters (sugar esters or), esters of fatty alcohols and polyethylene glycol, esters fatty acids and polyethylene glycol, bile acids, these surfactants can be used alone or as a mixture.
- An emulsion according to the invention can comprise from 0.01 to 5% by weight of surfactants relative to the dispersed phase.
- self-emulsifying mixture means a mixture consisting of a lipophilic phase, consisting of at least one oil and / or at least one fatty acid such as those described above, with at least one surfactant, this mixture being able to form an emulsion by simple mechanical stirring with an aqueous phase.
- a self-emulsifying mixture according to the invention can, after oral administration, form emulsions with the hydrophilic phases of the organism.
- the constituent surfactants of such a self-emulsifiable mixture may be selected from sorbitan esters and polyoxyethylene sorbitan esters such as those sold under the T een ® and Span ®, in particular polysorbate 80.
- the content of surfactants in the self-emulsifying mixture can be between 0.5 and 10% by weight relative to the lipophilic phase.
- the pharmaceutical composition according to the invention is in the form of a lipid solution.
- a lipid solution essentially comprises a lipophilic phase, generally consisting of at least one fatty acid and / or at least one oil, such as those mentioned above, the amisulpride being dissolved in this lipophilic phase.
- a lipid solution is substantially free of hydrophilic phase and of surfactant.
- the lipophilic phase of the lipid solution consists of a fatty acid, more preferably oleic acid.
- a pharmaceutical composition according to the invention may also comprise pharmaceutically acceptable excipients, such as diluents, preserving agents, osmotic agents, antioxidants, thickening agents, stabilizing agents, viscosity-reducing agents such as ethanol. , gelling agents and pH buffers.
- pharmaceutically acceptable excipients such as diluents, preserving agents, osmotic agents, antioxidants, thickening agents, stabilizing agents, viscosity-reducing agents such as ethanol. , gelling agents and pH buffers.
- compositions of the invention can be prepared in a conventional manner for a person skilled in the art.
- a lipid solution according to the invention can be prepared by dissolving, with stirring, the amisulpnde in the lipophilic phase. If necessary, other excipients can then be added, such as those mentioned above.
- the lipophilic phase containing 1 amisulpride can be introduced, with stirring, into the hydrophilic phase in which the surfactant (s) and (s) have been previously added and, where appropriate , hydrophilic excipients. Agitation may be achieved by means of a device of the Ultra-Turrax ® kind.
- a high pressure die for example of the type APV-Gaulm ®
- a self-emulsifying mixture according to the invention can be prepared conventionally, by introducing, with stirring, the required surfactant (s) into a lipophilic phase containing 1 amisulpride, this lipophilic phase being itself prepared as indicated above.
- a composition according to the invention can be presented in liquid form, divided or not, accompanied or not with a dosing device such as a spoon, in gelled form, in the form of soft capsules, of globules or, preferably, in the form of capsules.
- a dosing device such as a spoon
- gelled form in the form of soft capsules, of globules or, preferably, in the form of capsules.
- These capsules can consist of gelatin or starch and are usually sealed in a conventional manner.
- compositions according to the invention are mainly and preferably intended for oral administration. They can however be administered by other routes, for example by the rectal route.
- the invention relates to the use of 1 amisulpnde to prepare pharmaceutical compositions described above, for the treatment of dysthymia, the treatment of psychoses, more particularly for the treatment of paranoid and productive schizophrenia, acute delusional psychosis, as well as for the treatment of deficit states of schizophrenia, residual psychotic changes and inhibition states with slowing down.
- Said pharmaceutical compositions can also be used in the therapeutic treatment of delusional flushes, 1 hebephreno-catatonia, migraines, with or without photophobia or nausea.
- they can be used in the treatment of autism. They are still useful in withdrawal linked to the consumption of alcohol and / or narcotics and / or tobacco; more particularly, they reduce the risk of relapse during the post-weaning deficit period.
- the invention relates to new pharmaceutical compositions comprising 1 amisulpride and at least one pharmaceutically acceptable excipient, said compositions allowing the prolongation and / or the intensification of the gastrointestinal absorption of 1 amisulpride from so that the biodispombility of 1 amisulpride is greater than 50%, more generally between 60 and 75%.
- These pharmaceutical compositions are mainly intended for oral administration.
- Example 1 Self-emulsifying mixture suitable for rats
- a self-emulsifying mixture according to the invention is prepared by introducing 100 mg of amisulpride per se, as well as 4 mg of polysorbate 80, in oleic acid (qs 100 ml). Then, it is stirred slowly until complete dissolution.
- Example 2 Submicron O / W emulsion suitable for rats
- O / W submicronic emulsion according to the invention is prepared in the following manner:
- a hydrophilic phase is prepared by mixing 3.3 g of soya lecithin, 5.6 g of glycerin, 2 g of solidified polyoxyethylene castor oil (Cremophor ® RH 40) and 0.1 g of sodium hydrogen sulfite. This mixture is dissolved or dispersed in 82 g of water and heated to 70-80 ° C.
- the lipophilic phase is added to the hydrophilic phase and stirred with an Ultra-Turrax ® stirrer at 5000 revolutions / min. for ten minutes.
- a coarse emulsion which is refined by means of a homogenizer type high pressure APV Gaulm ®, in order to obtain a liquid emulsion in which the average diameter of lipophilic particle is less than 1 .mu.m.
- Example 3 O / W hydrophilic emulsion suitable for rats
- a hydrophilic O / W emulsion according to the invention is prepared in the following manner:
- a 2.25 mg / ml solution of polysorbate 80 in double-distilled glycerol is mixed with a lipid solution of amisulpnde per se in oleic acid. This mixture is then stirred with an Ultra-Turrax ® agitator, at 5000 rpm. for ten minutes.
- Example 4 O / W aqueous emulsion suitable for rats
- O / W aqueous emulsion according to the invention is prepared in the following manner:
- a hydrophilic phase is prepared by mixing lécithme of n a, polyoxyethylenated castor oil solidified (Cremophor ® RH 40) and one sodium hvdrogénosulfite. This mixture is dissolved or dispersed in water (qs 100 ml) and heated to 70-80 ° C.
- a lipophilic phase is prepared consisting of a solution of amisulpride per se in oleic acid.
- the lipophilic phase is added to the hydrophilic phase and stirred with an Ultra-Turrax ® stirrer at 5000 revolutions / min. for ten minutes.
- Amisulpide per se in oleic acid was introduced with slow stirring so as to obtain a lipid solution of amisulpride per se at 10 mg / ml in accordance with the invention.
- Amisulpride per se was introduced with oleic acid under slow stirring so as to obtain a 25 mg / ml solution of amisulpride lipid.
- This solution was divided into size 1 capsules at a rate of 0.4 g per capsule. Each capsule contained 100 mg of amisulpride per se.
- Example 6 was reproduced by replacing 1 amisulpride per se with (D) -tartrate from (S) - (-) - amisulpride, that is to say the compound of Example IV of patent FR 78 01632. There were thus obtained capsules containing 100 mg of active principle.
- compositions in accordance with the invention were tested in rats, according to the following protocol:
- the rats were Spragues Da ley OFA, males from 200 to
- T 0 After administration of the pharmaceutical composition (T 0 ), whether or not in accordance with the invention, the animals were replaced in their cage. They were kept on hold for a maximum of four hours after treatment. Samples were taken from the vena cava below time 0; 0.08; 0.25; 1; 2; 4; 6; 8; 16 and 24 hours. The tubes containing the collected blood were centrifuged and the recovered plasma was stored in the freezer.
- the concentration of amisulpnde per se in the plasma was measured by HPLC with fluorimetric detection.
- compositions according to the invention were tested, each comprising 10 mg / ml of amisulpride per se.
- compositions tested were those of Examples 1, 3, 4 and 5.
- compositions were compared with a reference solution, not in accordance with the invention, consisting of an aqueous 0.9% sodium chloride solution comprising 10 mg / ml of amisulpnde per se, the pH of which was adjusted to 3.5-6.5 using 1M hydrochloric acid.
- Form T max (hours) C max (ng / ml) AUC (ng / ml / h) pharmaceutical (Tl T2) solution of 1 82 287 reference (0.08-16) solution 0.08 108 410 lipid (0.08 -16) emulsion 0.08 110 213 aqueous (0.08-8) emulsion 0.08 107 310 hydrophilic (0.08-16) self-mixing 4 63 324 emulsifiable (0.08-24)
- Lipid solutions comprising increasing concentrations of amisulpnde per se were tested according to the protocol described in Example 8.
- the lipid solutions were prepared by stirring until the required dose of amisulpride per se was dissolved in 10 ml of oleic acid.
- the lipid solutions were compared with a reference solution consisting of an aqueous solution of sodium chloride comprising 50 mg / ml of amisulpride per se, the pH of which was adjusted to 3.5-6.5 using acid. hydrochloric 1M.
- the results obtained are shown in FIG. 2.
- the plasma concentrations of amisulpride per are expressed in ng / ml.
- T max , C max and the areas under the curve (AUC) obtained for each composition tested are grouped in Table II below.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth 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)
- Dispersion Chemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9611391 | 1996-09-18 | ||
FR9611391A FR2753376B1 (en) | 1996-09-18 | 1996-09-18 | PHARMACEUTICAL COMPOSITIONS COMPRISING AMISULPRIDE AND THERAPEUTIC APPLICATIONS THEREOF |
PCT/FR1997/001633 WO1998011881A1 (en) | 1996-09-18 | 1997-09-17 | Pharmaceutical compositions containing amisulpride and their therapeutic applications |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0927026A1 true EP0927026A1 (en) | 1999-07-07 |
Family
ID=9495859
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP97919108A Withdrawn EP0927026A1 (en) | 1996-09-18 | 1997-09-17 | Pharmaceutical compositions containing amisulpride and their therapeutic applications |
Country Status (8)
Country | Link |
---|---|
US (1) | US6069165A (en) |
EP (1) | EP0927026A1 (en) |
JP (1) | JP2001501192A (en) |
AU (1) | AU729707B2 (en) |
CA (1) | CA2265894A1 (en) |
FR (1) | FR2753376B1 (en) |
WO (1) | WO1998011881A1 (en) |
ZA (1) | ZA978383B (en) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6423334B1 (en) | 1997-10-01 | 2002-07-23 | Elan Corporation, Plc | Composition and method for enhancing transport across gastrointestinal tract cell layers |
AU3843999A (en) * | 1998-05-07 | 1999-11-23 | Elan Corporation, Plc | Solvent/cosolvent free microemulsion and emulsion preconcentrate drug delivery systems |
US6169094B1 (en) * | 1998-07-14 | 2001-01-02 | Sanofi-Synthelabo | Compositions of (S) (-)-amisulpride |
FR2790388B1 (en) * | 1999-03-04 | 2001-04-13 | Synthelabo | PHARMACEUTICAL COMPOSITIONS COMPRISING A BENZAMIDE AND AT LEAST ONE ABSORPTION PROMOTER |
JP5723287B2 (en) * | 2008-12-15 | 2015-05-27 | バナー ライフ サイエンシズ エルエルシー | Method for enhancing the release and absorption of water-insoluble active agents |
US20150018360A1 (en) * | 2011-09-13 | 2015-01-15 | Biomed Valley Discoveries, Inc. | Compositions and methods for treating metabolic disorders |
US11377421B2 (en) | 2016-11-28 | 2022-07-05 | Lb Pharmaceuticals Inc. | Psychotropic agents and uses thereof |
WO2018098497A1 (en) | 2016-11-28 | 2018-05-31 | Lb Pharmaceuticals Inc. | Psychotropic agents and uses thereof |
EP3625212A4 (en) * | 2017-05-18 | 2021-03-31 | LB Pharmaceuticals Inc. | Psychotropic agents and uses thereof |
WO2019113084A1 (en) | 2017-12-05 | 2019-06-13 | Sunovion Pharmaceuticals Inc. | Crystal forms and production methods thereof |
BR112020011189A2 (en) | 2017-12-05 | 2020-11-17 | Sunovion Pharmaceuticals Inc. | non-racemic mixtures and uses thereof |
FR3081350B1 (en) * | 2018-05-24 | 2020-08-28 | Paris Sciences Lettres Quartier Latin | COLLOIDAL PARTICLES HOMOGENEOUSLY FUNCTIONALIZED BY BIOMOLECULES |
EP3856156A2 (en) * | 2018-09-28 | 2021-08-04 | Medizinische Hochschule Hannover (MHH) | 5-ht7 antagonist for the treatment of dementia-associated tauopathies |
GB201904771D0 (en) * | 2019-04-04 | 2019-05-22 | Orexo Ab | New pharmaceutical compositions |
US11160758B2 (en) | 2019-06-04 | 2021-11-02 | Sunovion Pharmaceuticals Inc. | Modified release formulations and uses thereof |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2415099A1 (en) * | 1978-01-20 | 1979-08-17 | Ile De France | NEW DERIVATIVES OF 4-AMINO-5-ALKYLSULFONYL ORTHO-ANISAMIDES, THEIR METHODS OF PREPARATION AND THEIR APPLICATION AS PSYCHOTROPES |
US5446070A (en) * | 1991-02-27 | 1995-08-29 | Nover Pharmaceuticals, Inc. | Compositions and methods for topical administration of pharmaceutically active agents |
US5980882A (en) * | 1997-04-16 | 1999-11-09 | Medeva Pharmaceuticals Manufacturing | Drug-resin complexes stabilized by chelating agents |
-
1996
- 1996-09-18 FR FR9611391A patent/FR2753376B1/en not_active Expired - Fee Related
-
1997
- 1997-09-17 ZA ZA9708383A patent/ZA978383B/en unknown
- 1997-09-17 JP JP10514342A patent/JP2001501192A/en active Pending
- 1997-09-17 AU AU43058/97A patent/AU729707B2/en not_active Ceased
- 1997-09-17 WO PCT/FR1997/001633 patent/WO1998011881A1/en not_active Application Discontinuation
- 1997-09-17 US US09/254,686 patent/US6069165A/en not_active Expired - Fee Related
- 1997-09-17 CA CA002265894A patent/CA2265894A1/en not_active Abandoned
- 1997-09-17 EP EP97919108A patent/EP0927026A1/en not_active Withdrawn
Non-Patent Citations (1)
Title |
---|
See references of WO9811881A1 * |
Also Published As
Publication number | Publication date |
---|---|
US6069165A (en) | 2000-05-30 |
FR2753376A1 (en) | 1998-03-20 |
AU4305897A (en) | 1998-04-14 |
ZA978383B (en) | 1998-03-24 |
JP2001501192A (en) | 2001-01-30 |
CA2265894A1 (en) | 1998-03-26 |
WO1998011881A1 (en) | 1998-03-26 |
FR2753376B1 (en) | 1998-10-16 |
AU729707B2 (en) | 2001-02-08 |
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