EP0983065A1 - Arzneizusammensetzung mit verlängerter magenverweilzeit - Google Patents
Arzneizusammensetzung mit verlängerter magenverweilzeitInfo
- Publication number
- EP0983065A1 EP0983065A1 EP98920623A EP98920623A EP0983065A1 EP 0983065 A1 EP0983065 A1 EP 0983065A1 EP 98920623 A EP98920623 A EP 98920623A EP 98920623 A EP98920623 A EP 98920623A EP 0983065 A1 EP0983065 A1 EP 0983065A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon dioxide
- composition according
- benzamide
- salts
- dioxide generating
- 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.)
- Ceased
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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0065—Forms with gastric retention, e.g. floating on gastric juice, adhering to gastric mucosa, expanding to prevent passage through the pylorus
-
- 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
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- 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
- A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
- A61K9/0007—Effervescent
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
Definitions
- the present invention relates to pharmaceutical compositions with gastric residence comprising an active principle of the family of benzamides.
- Benzamides are chemical compounds whose structure includes the following motif:
- benzamides are useful as an active ingredient in medicaments intended for the treatment, in particular, of disorders of the central nervous system.
- Such benzamides may consist of amisulpride, tiapride, sulpiride, their salts, if any, their enantiomers and the salts of these enantiomers, as well as some of their derivatives.
- benzamides can be administered orally.
- bioavailability is understood here to mean the fraction of the active principle which is absorbed from its pharmaceutical form and which reaches the plasma.
- Low or irregular bioavailability can be the result of several factors, among which we can cite: low solubility or very slow dissolution of the active principle or of the dosage form which contains it; instability of the active ingredient, either over the entire length of the gastrointestinal tract, or in only one of its parts; the enzymatic degradation in the mucosa or in the liver of the active ingredient; slow or incomplete absorption of the active ingredient due to slow passive diffusion through the intestine or, in the case of an active mechanism, saturation of the transport system. It is known that the bioavailability of certain active ingredients can be modified by means of a sustained-release formulation which releases the active ingredient over the entire length of the gastrointestinal tract.
- the Applicant then considered improving the bioavailability of benzamides by formulating them in the form of a pharmaceutical composition with gastric residence promoting absorption in the small intestine, or even, more specifically, the upper parts of the small intestine.
- the invention thus consists of a pharmaceutical composition with gastric residence, characterized in that it comprises:
- (c) means allowing partial retention of the carbon dioxide generated by said carbon dioxide generating system.
- the figure represents the plasma release profile, in humans, of tiapride hydrochloride, this profile being obtained with a pharmaceutical composition according to the invention.
- the term "benzamide" within the meaning of the present invention, and unless otherwise indicated, covers the various enantiomers or diastereoisomers of these compounds, including their mixtures, in particular their racemic mixtures.
- a pharmaceutical composition with gastric residence is intended to reside for more than one hour in the stomach with a view to a prolonged and / or controlled release of the active principle.
- a pharmaceutical composition with gastric residence according to the invention has the advantage of being able to float on the surface of the liquids contained in the stomach, and this very quickly after having been absorbed. It has thus been found that a composition according to the invention can float for less than two minutes after being brought into contact with an aqueous liquid.
- the invention is more particularly suitable for the active principles consisting of sulpiride, 1 amisulpride, their salts, their enantiomers and the salts of these enantiomers, as well as tiapride, its oxide and its salts.
- Sulpiride is a neuroleptic useful in the treatment of acute and chronic psychoses (i) with a dehinibitating dosage: psychoses where predominantly withdrawal states, apragmatism, abuli or (ii) with dosage antiproductive: delusional or confusing psychoses, schizophrenia.
- Tiapride in particular in the form of hydrochloride, is a neuroleptic useful in the treatment of agitation and aggressiveness of the demented subject, behavioral disorders when they are manifested by phenomena of hyperactivity, aggressiveness, d irritability, especially in alcohol and the elderly, motor behavior disorders such as, for example, tremors, spontaneous or iatrogenic neuromuscular dyskinesia, abnormal movements such as chorea, tics, hemiballism, sensory behavior disorders such as for example headaches, migraines, various pain, especially intense and rebellious pain.
- the present invention is more particularly suitable for tiapride hydrochloride.
- Amisulpride or 4-amino-N [(1-ethyl-2-pyrrolidinyl) methyl] -5- (ethylsulfonyl) -2-methoxybenzamide, its enantiomers and some of its derivatives are described in French Patent No. 78,01632, the teaching of which is fully incorporated in this description.
- the invention is particularly suitable for amisulpride per se, ie 4 -amino-N- [(1-ethylpyrrolidin-2-yl) methyl] -5- (ethylsulfonyl) - 2-methoxybenzamide, its enantiomers levogyre
- 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-dihydroxybutanedioate du (S) - (-) -4-amino- N- [(1-ethylpyrrolidin-2-yl) methyl] -5- (ethylsulfonyl) -2- methoxybenzamide.
- Amisulpride is a neuroleptic used in the treatment of psychosis, more particularly in the treatment of paranoid and productive schizophrenia, acute delusional psychosis, as well as in the treatment of deficit states of schizophrenia, residual psychotic changes and states of inhibition with slowdown. Amisulpride is also useful in the treatment of dysthymia.
- benzamides can be used in the context of the present invention such as metoclopramide, veralipride, alizapride or clebopride.
- the main function of the carbon dioxide generating system is to form carbon dioxide in the form of bubbles. These bubbles contribute to quickly bringing, then to maintaining the pharmaceutical composition of the invention on the surface of the liquids contained in the stomach.
- a carbon dioxide generating system suitable in a pharmaceutical composition according to the invention generally comprises at least one carbon dioxide generating agent.
- the carbon dioxide generating agent is usually a carbonate of an alkali or alkaline earth metal, such as calcium carbonate, or a bicarbonate of an alkali metal, preferably sodium bicarbonate.
- Such a carbon dioxide generating system consisting only of a carbon dioxide generating agent, does not begin to form bubbles of carbon dioxide until after having been brought into contact with a medium at acidic pH, generally that of l 'stomach.
- a system that generates carbon dioxide. carbon independent of pH.
- a system can comprise a carbon dioxide generating agent such as those mentioned above, as well as at least one acid compound chosen from the group consisting of monocarboxylic acids such as lactic acid, polycarboxylic acids and the partial salts of polycarboxylic acids. Mention may more particularly be made, as acid compounds, of tartaric, maleic, malonic, malic, fumaric, succinic, adipic, citric acids and their partial salts, such as monosodium citrate.
- the acid compound content is generally chosen so that the number of moles in said acid compound relative to the number of moles in said carbon dioxide generating agent is between 0.7 and 1.4 times the stoichiometry.
- the active principle or any other component used in the formulation of the composition according to the invention has a basic character, it may be necessary to increase the content of acidic compound accordingly.
- the means allowing the partial retention of the carbon dioxide generated by the carbon dioxide generating system must allow the diffusion of the carbon dioxide in a controlled manner. It must prevent the too rapid diffusion of carbon dioxide which would lead to too short a flotation in time of the pharmaceutical composition according to the present invention. Conversely, it must allow sufficient diffusion of carbon dioxide to ensure a determined flotation time of said composition in the stomach, as well as sufficient diffusion of water or an aqueous compound within the composition according to the invention.
- This means can consist of a porous mineral matrix, in particular matrices based on silicates or calcium fluoride, or, preferably, in a polymer.
- said polymer consists of at least one hydrophilic polymer.
- the hydrophilic polymers suitable for a pharmaceutical composition according to the invention are those which can form a hydrocolloid gel in contact with an aqueous liquid, in particular the aqueous liquids contained in the stomach.
- hydrophilic polymers mention may be made of (i) natural polysaccharides such as alginates, xanthan gum, guar gum or locust bean gum, (ii) hemisynthetic polysaccharides, in particular cellulose derivatives such as methylcellulose, Ethylcellulose, methylhydroxyethylcellulose, carboxymethylcellulose and its salts such as sodium carboxymethylcellulose or carboxymethylcellulose calcium, and preferably hydroxypropylcellulose, hydroxypropylmethylcellulose and mixtures of hydroxypropylcellulose and hydroxypropylmethylcellulose or hydroxypropylmethylcellulose synthetic hydrophilic polymers such as polymers derived from acrylic and methacrylic acids and their salts, such polyacrylates include those sold under the Carbopol ® brand, amino acid polymers such as polylysine and (iv) certain proteins or derivatives thereof such as gelatins. Cellulose derivatives are particularly preferred.
- contents of the various constituent components of a pharmaceutical composition according to the invention are generally chosen so that the relative density in the stomach of this composition is less than 1.00.
- a pharmaceutical composition according to the invention comprises from 5 to 70%, preferably from 10 to 60% by weight of active principle, from 10 to 75%, preferably from 15 to 50% by weight in at least one hydrophilic polymer and from 5 to 50%, preferably 10 to 40% by weight of carbon dioxide generating agent, the percentages being expressed relative to the total weight of said composition.
- a pharmaceutical composition with gastric residence according to the invention can be in the form of capsules, granules or, preferably, tablets. These last are floating tablets, that is, they can float on stomach fluids.
- Such a pharmaceutical composition can be prepared by simple mixing of its components, followed by pharmaceutical shaping carried out in a conventional manner.
- the mixture comprising all or part of the constituent components of the composition according to the invention, may be granulated or agglomerated.
- the mixture of constituent components of the composition according to the invention can be compressed.
- Lubricants such as polyethylene glycols with a molecular weight between 1,500 and 10,000, magnesium stearate or sodium stearyl fumarate, as well as conventional excipients such as flow agents or compression agents, can be added to the tablet mixture.
- a pharmaceutical composition according to the invention comprising a given benzamide, can be used for the treatment of diseases already treated with the same benzamide in its conventional form.
- the pharmaceutical composition according to the invention can be used in the treatment of one of the pathologies mentioned above, respectively, for each of these benzamides.
- Example 1 floating tablets containing tiapride hydrochloride
- tiapride hydrochloride 37.0% hydroxypropyl methylcellulose 1 3 0.0% polyethylene glycol 6000 3.0% anhydrous sodium citrate 16.8% sodium bicarbonate 13.2%
- the homogeneous mixture thus formed was compressed on an alternative tableting machine, to obtain round, flat tablets, with a diameter of 15 mm and comprising 300 mg of tiapride hydrochloride.
- the tablets were placed in rotating baskets at 75 rpm, submerged in 1000 ml of 0.01 M hydrochloric acid at a temperature of 37 ⁇ 0.5 ° C.
- tiapride was determined for each sample by UV spectrophotometry, in comparison with the absorbance of a standard solution containing 300 ⁇ g / ml of tiapride hydrochloride, in 0.01M hydrochloric acid.
- tiapride hydrochloride 44.17% hydroxypropyl methylcellulose 1 28.68% magnesium stearate 0.50% sodium stearyl fumarate 2.87% anhydrous monosodium citrate 13.26% anhydrous monosodium carbonate 10.42% silica Aerosil 200 2 0.10%
- the homogeneous mixture thus formed was compressed on an alternative tableting machine, to obtain round, convex tablets, with a diameter of 10 mm and comprising 200 mg of tiapride expressed as tiapride base.
- the tablets were placed in cylindrical baskets, length 35 mm and diameter 19 mm, perforated in diameter 5 mm. They are immersed in 1000 mL of 0.01M hydrochloric acid at a temperature of 37 ⁇ 0.5 ° C. The dissolution medium was stirred by rotating vanes at 100 rpm. The medium was taken every 15 minutes in a closed circuit by a peristaltic pump, and the tiapride dosage determined by UV spectrophotometry in comparison with the absorption of a standard solution containing 200 ⁇ g / mL of tiapride base, in acid. 0.01M hydrochloric.
- the tablets to be tested were introduced into 6 tubes.
- the tiapride hydrochloride tablets of Example 2 started to float at 2 min, and continued to float for at least 120 min.
- Example 2 The tablets of Example 2 were administered to 12 volunteers. Plasma samples were taken every 30 min. from 0 to 3 h, every 2 h from 4 to 12 h, then at 16, 20, 24, 36 and 48 h after administration. The results are shown in Figure, which shows the average plasma levels of tiapride base for the tablets of Example 2.
- the mixture was then granulated with 10% water, and the granule dried in vacuo. After calibration, the granule was mixed with 13.7% sodium bicarbonate, then lubricated with 1% magnesium stearate and 0.2% Aerosil silica 200 (marketed by Degussa).
- the homogeneous mixture thus formed was compressed on an alternative tableting machine to obtain round convex tablets with a diameter of 10 mm and comprising 200 mg of amisulpride.
- Example 2 The dissolution method of Example 2 was used to determine the dissolution profile of the tablets thus prepared.
- the standard used was 200 ⁇ g / ml of amisulpride base. The following results were obtained:
- Amisulpride floating tablets were prepared according to the method described in Example 3. The tablets obtained included (% by mass) and were dosed at 50 mg in (D) -tartrate of (S) - ⁇ -) - amisulpride .
- Example 2 The dissolution method of Example 2 was used, to determine the dissolution profile of the tablets thus prepared.
- the standard used was 50 ⁇ g / mL of amisulpride base. The following results were obtained.
- Floating tablets of amisulpride were prepared according to the process described in Example 1.
- the tablets obtained included (% by mass):
- Example 1 The dissolution method of Example 1 was used, by modifying the sample collection times, to determine the dissolution profile of the tablets thus prepared. The following results were obtained:
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Psychology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9704803 | 1997-04-18 | ||
FR9704803A FR2762213B1 (fr) | 1997-04-18 | 1997-04-18 | Composition pharmaceutique a retention gastrique |
PCT/FR1998/000755 WO1998047506A1 (fr) | 1997-04-18 | 1998-04-15 | Composition pharmaceutique a residence gastrique |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0983065A1 true EP0983065A1 (de) | 2000-03-08 |
Family
ID=9506077
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP98920623A Ceased EP0983065A1 (de) | 1997-04-18 | 1998-04-15 | Arzneizusammensetzung mit verlängerter magenverweilzeit |
Country Status (19)
Country | Link |
---|---|
EP (1) | EP0983065A1 (de) |
JP (1) | JP2001523241A (de) |
KR (1) | KR20010006353A (de) |
CN (1) | CN1252720A (de) |
AR (1) | AR015586A1 (de) |
AU (1) | AU737634B2 (de) |
CA (1) | CA2286081A1 (de) |
FR (1) | FR2762213B1 (de) |
HU (1) | HUP0002455A3 (de) |
IL (1) | IL131995A0 (de) |
JO (1) | JO2017B1 (de) |
MA (1) | MA26482A1 (de) |
NO (1) | NO995039L (de) |
NZ (1) | NZ500288A (de) |
PE (1) | PE68199A1 (de) |
PL (1) | PL336273A1 (de) |
TN (1) | TNSN98049A1 (de) |
WO (1) | WO1998047506A1 (de) |
ZA (1) | ZA983258B (de) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6169094B1 (en) * | 1998-07-14 | 2001-01-02 | Sanofi-Synthelabo | Compositions of (S) (-)-amisulpride |
FR2784583B1 (fr) * | 1998-10-16 | 2002-01-25 | Synthelabo | Composition pharmaceutique a residence gastrique et a liberation controlee |
FR2790388B1 (fr) * | 1999-03-04 | 2001-04-13 | Synthelabo | Compositions pharmaceutiques comprenant un benzamide et au moins un promoteur d'absorption |
EP1245227A1 (de) | 2001-03-31 | 2002-10-02 | Jagotec Ag | Pharmazeutische, im Magen aufschwimmende Tablette für die programmierte Freisetzung des Wirkstoffes und Verfahren zur Herstellung des in der Tablette enthaltenen schwimmfähigen Materials |
WO2009157711A2 (ko) * | 2008-06-24 | 2009-12-30 | Park Eun-Seok | 위장체류형 다공성 정제 및 그의 제조 방법 |
FR2949061B1 (fr) * | 2009-08-12 | 2013-04-19 | Debregeas Et Associes Pharma | Microgranules flottants |
RS54024B1 (en) | 2012-10-12 | 2015-10-30 | Omya International Ag | GASTRORETENCY FORMULATION OF MEDICINES AND SYSTEMS FOR DELIVERY AND METHODS OF THEIR PREPARATION USING FUNCTIONALIZED CALCIUM CARBONATE |
WO2019113079A1 (en) | 2017-12-05 | 2019-06-13 | Sunovion Pharmaceuticals Inc. | Nonracemic mixtures and uses thereof |
EP3720435B1 (de) | 2017-12-05 | 2024-03-06 | Sunovion Pharmaceuticals Inc. | Kristallformen und herstellungsverfahren dafür |
JP7044649B2 (ja) * | 2018-06-28 | 2022-03-30 | 株式会社ファンケル | 胃内浮遊錠剤 |
US11160758B2 (en) | 2019-06-04 | 2021-11-02 | Sunovion Pharmaceuticals Inc. | Modified release formulations and uses thereof |
WO2023214018A1 (en) | 2022-05-06 | 2023-11-09 | Galenix Innovations | Gastro-retentive swellable sustained release composition |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2415099A1 (fr) * | 1978-01-20 | 1979-08-17 | Ile De France | Nouveaux derives de 4-amino-5-alkylsulfonyl ortho-anisamides, leurs procedes de preparation et leur application comme psychotropes |
FR2554718B1 (fr) * | 1983-11-14 | 1986-04-04 | Ethypharm Sa | Nouvelles formes galeniques du sulpiride utilisables par voie orale |
FR2556964A1 (fr) * | 1983-12-23 | 1985-06-28 | Ile De France | Nouvelles formes galeniques du sulpiride utilisables par voie orale |
JPS62178518A (ja) * | 1986-01-30 | 1987-08-05 | Toho Yakuhin Kogyo Kk | 新規持続性スルピリド錠剤 |
JPH0776172B2 (ja) * | 1986-04-16 | 1995-08-16 | 藤沢薬品工業株式会社 | マトリツクス錠 |
CA2039742A1 (en) * | 1990-04-23 | 1991-10-24 | Andrew B. Dennis | Tablet composition and method for problem pharmaceutical materials |
-
1997
- 1997-04-18 FR FR9704803A patent/FR2762213B1/fr not_active Expired - Fee Related
-
1998
- 1998-04-15 NZ NZ500288A patent/NZ500288A/xx unknown
- 1998-04-15 JP JP54514398A patent/JP2001523241A/ja active Pending
- 1998-04-15 KR KR1019997009438A patent/KR20010006353A/ko not_active Application Discontinuation
- 1998-04-15 AU AU73416/98A patent/AU737634B2/en not_active Ceased
- 1998-04-15 PL PL98336273A patent/PL336273A1/xx unknown
- 1998-04-15 EP EP98920623A patent/EP0983065A1/de not_active Ceased
- 1998-04-15 WO PCT/FR1998/000755 patent/WO1998047506A1/fr not_active Application Discontinuation
- 1998-04-15 CA CA002286081A patent/CA2286081A1/en not_active Abandoned
- 1998-04-15 IL IL13199598A patent/IL131995A0/xx unknown
- 1998-04-15 HU HU0002455A patent/HUP0002455A3/hu unknown
- 1998-04-15 CN CN98804269A patent/CN1252720A/zh active Pending
- 1998-04-16 TN TNTNSN98049A patent/TNSN98049A1/fr unknown
- 1998-04-17 MA MA25037A patent/MA26482A1/fr unknown
- 1998-04-17 AR ARP980101773A patent/AR015586A1/es unknown
- 1998-04-17 ZA ZA983258A patent/ZA983258B/xx unknown
- 1998-04-17 PE PE1998000281A patent/PE68199A1/es not_active Application Discontinuation
- 1998-04-18 JO JO19982017A patent/JO2017B1/en active
-
1999
- 1999-10-15 NO NO995039A patent/NO995039L/no not_active Application Discontinuation
Non-Patent Citations (1)
Title |
---|
See references of WO9847506A1 * |
Also Published As
Publication number | Publication date |
---|---|
AU737634B2 (en) | 2001-08-23 |
FR2762213B1 (fr) | 1999-05-14 |
NO995039D0 (no) | 1999-10-15 |
TNSN98049A1 (fr) | 2005-03-15 |
CN1252720A (zh) | 2000-05-10 |
HUP0002455A3 (en) | 2001-01-29 |
FR2762213A1 (fr) | 1998-10-23 |
JP2001523241A (ja) | 2001-11-20 |
KR20010006353A (ko) | 2001-01-26 |
AR015586A1 (es) | 2001-05-16 |
AU7341698A (en) | 1998-11-13 |
PL336273A1 (en) | 2000-06-19 |
HUP0002455A2 (hu) | 2000-12-28 |
NO995039L (no) | 1999-12-17 |
JO2017B1 (en) | 1999-05-15 |
IL131995A0 (en) | 2001-03-19 |
MA26482A1 (fr) | 2004-12-20 |
WO1998047506A1 (fr) | 1998-10-29 |
PE68199A1 (es) | 1999-07-15 |
NZ500288A (en) | 2001-03-30 |
CA2286081A1 (en) | 1998-10-29 |
ZA983258B (en) | 1998-10-19 |
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