GB2151920A - Oral compositions containing sulpiride - Google Patents
Oral compositions containing sulpiride Download PDFInfo
- Publication number
- GB2151920A GB2151920A GB08408978A GB8408978A GB2151920A GB 2151920 A GB2151920 A GB 2151920A GB 08408978 A GB08408978 A GB 08408978A GB 8408978 A GB8408978 A GB 8408978A GB 2151920 A GB2151920 A GB 2151920A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulpiride
- type
- weight
- compositions
- eudragit
- 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.)
- Granted
Links
- BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 title claims description 24
- 229960004940 sulpiride Drugs 0.000 title claims description 24
- 239000000203 mixture Substances 0.000 title claims description 14
- 238000000338 in vitro Methods 0.000 claims description 8
- 229920003134 Eudragit® polymer Polymers 0.000 claims description 7
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 5
- 230000002496 gastric effect Effects 0.000 claims description 5
- 230000000968 intestinal effect Effects 0.000 claims description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 4
- 239000000454 talc Substances 0.000 claims description 4
- 229910052623 talc Inorganic materials 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
- 235000013681 dietary sucrose Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- 229960004793 sucrose Drugs 0.000 claims description 3
- 239000001856 Ethyl cellulose Substances 0.000 claims description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 2
- 229920001800 Shellac Polymers 0.000 claims description 2
- 229920001249 ethyl cellulose Polymers 0.000 claims description 2
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 2
- 239000004208 shellac Substances 0.000 claims description 2
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 claims description 2
- 229940113147 shellac Drugs 0.000 claims description 2
- 235000013874 shellac Nutrition 0.000 claims description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims 4
- 229920003136 Eudragit® L polymer Polymers 0.000 claims 1
- 229920003151 Eudragit® RL polymer Polymers 0.000 claims 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 239000008101 lactose Substances 0.000 claims 1
- DNKKLDKIFMDAPT-UHFFFAOYSA-N n,n-dimethylmethanamine;2-methylprop-2-enoic acid Chemical compound CN(C)C.CC(=C)C(O)=O.CC(=C)C(O)=O DNKKLDKIFMDAPT-UHFFFAOYSA-N 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 239000002775 capsule Substances 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- 239000007891 compressed tablet Substances 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- -1 N-(l-ethyl-2-pyrrolidinyl)methyl-2-methoxy-6sulphamoylbenzamide Chemical compound 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000004531 microgranule Substances 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 231100000683 possible toxicity Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—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
- A61K9/14—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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
- A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
1 GB 2 151920 A 1
SPECIFICATION
Oral compositions containing sulpiride The present invention concerns orally administrable pharmaceutical forms of Sulpiricle and their preparation.
Sulpiride, viz. N-(l-ethyl-2-pyrrolidinyl)methyl-2-methoxy-6sulphamoylbenzamide, is known as an excel lent neuroleptic disinhibitor, having as its main therapeutic indication the treatmnt of acute and chronic psychoses. Its characteristics and properties are described in particular in French Patents Nos. 1,472 025, 4879 M and 5916 M.
Available orally active medicaments containing Sulpiride include compressed tablets, capsules and drinkable aqueous solutions, but as set out below these forms require a plurality of daily doses and sometimes are incompletely absorbed by the organism. Consequently, attempts have been made to modify the form of composition to substantially enhance acceptance by patients while reducing the number of daily doses required.
The plasmatic half-line of the active ingredient Sulpiride is about eight and a half hours. Ittherefore seems possible to produce a form of the product enabling the average daily dose to be reduced to two capsules or tablets each containing 100 mg of Sulpiride, one being taken in the morning and one on the evening, or even to one capsule or one tablet containing 200 mg of Sulpiride.
For that purpose, microgranules having a prolonged effect were produced, in accordance with the 20 conventional processes described in particular in French Patents Nos. 2 313 915 and 2 453 642. Neutral grains about 0.50 mm in diameter and comprising 25% of starch and 75% of saccharose were used. The Sulpiride was directed onto them in a turbine process, by means of an alcoholic solution of polyvinylpyrroliclone, and then conventional coating fibres were applied, based on polymer of the shellac; methacrylate or ethylcellulose type, so as to produce pre-established standard kinetics for liberation of the Sulpiride in vitro 25 in gastric and intestinal media, in accordance with the following specifications:
1 st hour: liberation less than 40%.
4th hour: liberation less than 75%.
8th hour: liberation more than 75%.
Liberation at the first hour is effected in an artificial gastric juice having a pH of 1.3, and at the fourth and at 30 eighth hours in artificial intestinal juices having pHs of 4.5 and 7 respectively. The operating conditions for studying the liberation of the active ingredient are known and described in the above-mentioned patents.
Those microgranules were then used to produce capsules and compressed tablets giving a dosage of 100 mg; the absorption of the Sulpiride was studied by determining the plasmatic amounts of Sulpiride in circulation by means of radio-immunology; and the results obtained were compared with those obtained 35 from the capsule form at present on the market.
The results are set out in Table A below and show that, with the two formulations of microgranules used (form I and form 11), the loss in the amount of active ingredient is too substantial with respect to that with the normal form of capsules (form IV) to make it possible to provide an effective prolonged-effect medicament.
Forms I and 11 used had the following kinetics in respect of liberation in vitro in artificial media:
form 1 form 11 Liberation at the first hour in a medium of pH 1.3 20.0% 29.2% 45 Liberation at the fourth hour in a medium of pH 4.5 68.6% 58.4% Liberation at the eighth hour in a medium of pH 7 90.8% 98.2% 50 After studying a series of prolonged-effect formulations which all gave results incompatible with producing a good properly absorbed oral form, the idea was conceived of retaining the microgranule form (substantially spherical grains of a diameter of between 0.2 and 2 mm), which in practice should permit of better absorption of the active ingredient than a conventional powder of the capsule or the tablet, while having kinetics in respect of liberation in vitro much closer to those forms, that is to say, liberating substantially 90% of the active ingredient after one hour in an artificial gastric medium having a pH of 1.3.
Surprisingly, the results of the microgranules using those in vitro kinetics showed that, in dependence on the comparative plasmatic proportions, the form III formed by microgranules put into capsule form with a dosage of 100 mg makes it possible to achieve a degree of absorption double that obtained with the conventional capsules of Sulpiride (form IV), while retaining a slightly greater period of action and substantially reducing the differences in absorption form one subject to another. The above-indicated improvement in the absorption of Sulpiricle, both in the quantitative respect and in respect of its regularity, permits of a reduction in the doses used and the number of daily doses to be taken.
Those results are set out in Table A, and also in Figure 1, showing the variation in the plasmatic proportions in circulation between 0 and 32 hours, expressed in ng/ml of Sulpiride, by comparison between 65 2 GB 2 151920 A 2 form III and form IV.
Complementary experiments, in the course of which the external coatings of the microogranules according to the invention are varied, made it possible to acertain that the preferential form with improved absorption of the Sulpiride should substantially correspond to the following analytical conditions in respect 5 of liberation in vitro:
minutes: liberation between 35 and 50% in an artificial gastric medium of pH 1.3 minutes: liberation between 60 and 75% in an artificial gastric medium of pH 1.3 60minutes: liberation between 80 and 95% in an artificial intestinal medium of pH 4.5.
Moreover, an overall liberation rate of higher than 90% is noted in an artificial intestinal medium of pH 6.9.
The production formula for-2500 capsules with a dosage of 100 mg; of form 111, and the process for their 10 manufacture is set out below byway of example.
250 g of Sulpiride in a 20% ethanolic solution of polyvinyl pyrrol idone is applied by a turbine process to 50 g of neutral grains substantially 0. 50 mm in diameter and comprising about 25% of starch and 75% of saccharose.
After drying and sieving, outside layers are applied, comprising methacrylic polymers marketed under the 15 registered trade mark Eudragit by Rohm and Haas in alcoholic solutions in proportions of 4 parts by weight of Eudragittype Lfor 1 part by weight of Eudragit type RL.
Drying is then effected with small proportions of talc until microgranules are produced, which liberate substantially 100% Sulpiride in an hour in accordance with the analytical conditions defined above.
Drying is then effected in a drying oven at 37'C for abouttwo days, and then the outside layer is completed 20 by projecting 40 g of a 13.5% ethanolic solution of Eudragit type RL. The titre found is about 730 mg of active ingredient per gram of microgranules.
The microgranules produced in that way comply with the standards in respect of in vitro liberation as set out above, as representative of the novel forms of Sulpiricle in accordance with the invention.
Their accelerated and natural stabilities are found to be excellent, without the appearance of potential toxicity.
They may be used in the form of capsules, compressed tablets or suspensions in neutral media.
It will be appreciated that variations may be introduced, in particular with regard to the proportions of the excipients and the active ingredient, the composition of the neutral grains, and the nature of the polymers forming the outer layers.
In the foregoing description, parts and percentages are by weight unless otherwise stated.
TABLE A
Kinetics Mean maximum Time corresponding Area under the curve observed (A U0 35 parameters concentration to mean Cmax (Cmax) in ngImI Mean (Tmax) O-Bhours 0-24 hours in hours in ngImI -1h in ngImI -1h Form 1 75 40 4 1.50 3.40 75 720 190 40 Form 11 80 -t 45 3.90 -t 1.40 3.65 80 780-t200 Form Ill 315:h 65 3.30 -t 1.30 1280 -t: 230 2970 -t 400 45 Form W 150-60 3.20 --t 1.30 715 -i: 320 1565 -t: 430
Claims (8)
1. Pharmaceutical oral compositions containing Sulpiride and in the form of microgranules formed by a 50 neutral grain of the type comprising a mixture of saccharose, starch, lactose, talc or stearic acid, to which the Sulpiride is applied, followed by an outer layer of microporous polymers of the ethylcellulose, shellac, methacrylate, cellulose acetophthalate or polyvinylpyrrolidone type, in which liberation in vitro of the Sulpiride in artificial gastric and intestinal media is substantially as follows:
after 15 minutes, 35 to 50% of a medium of a pH 1.3; after 30 minutes, 60 to 75% in a medium of pH 1.3; after 60 minutes, 80 to 95% in a medium of pH 4.5; after more than 2 hours, more than 90% in a medium of pH 6.9.
2. Compositions as claimed in Claim 1 in which the polymer is one or more methacrylates.
3. Compositions as claimed in Claim 2 in which the methacrylate(s) islare of the type sold under the trade 60 mark Eudragit.
4. Compositions as claimed in Claim 3 in which the methacrylates comprise 3 to 4 parts by weight of methacrylates of the type Eudragit L and 0.5 to 2 parts by weight of methacrylates of the type Eudragit RL.
5. Compositions as claimed in any preceding claim in which the layer containing the Sulpiride applied to the neutral grain comprises from 0.5 to 5% by weight of polyvinyl pyrrolidone.
3 GB 2 151 920 A 3
6. Compositions as claimed in any preceding claim in which the layer containing the Sulpiride contains small proportions of talc.
7. A process for preparing compositions as claimed in any preceding claim, comprising projecting in a turbine process about 70 parts by weight of Sulpiride in solution onto 20 parts by weight of neutral grains, drying and sifting the microgranules, applying a solution of the desired polymers to form the outer layer in quantity so as to adjust the Sulpiride in vitro liberation kinetics in accordance with the said characteristic values.
8. A process as claimed in Claim 7 in which the Sulpiride is applied in an alcoholic solution of polyvinyl pyrrolidone, an alcoholic solution of methacrylic polymers comprising about 4 parts by weight of lo Eudragit of type L and 1 part by weight of Eudragit of type RL is applied, drying is effected with talc and then 10 in a drying oven at 370C and the outer layer is completed by means of an alcoholic solution of Eudragit of type RL.
Printed in the UK for HMSO, D8818935, 6185, 7102. Published by The Patent Office, 25 Southampton Buildings, London, WC2A lAY, from which copies may be obtained.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8320635A FR2556964A1 (en) | 1983-12-23 | 1983-12-23 | NEW GALENIC FORMS OF SULPIRIDE USED ORALALLY |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8408978D0 GB8408978D0 (en) | 1984-05-16 |
| GB2151920A true GB2151920A (en) | 1985-07-31 |
| GB2151920B GB2151920B (en) | 1987-09-23 |
Family
ID=9295477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08408978A Expired GB2151920B (en) | 1983-12-23 | 1984-04-06 | Oral compositions containing sulpiride |
Country Status (38)
| Country | Link |
|---|---|
| EP (1) | EP0147244A1 (en) |
| JP (1) | JPS60139616A (en) |
| KR (1) | KR910004570B1 (en) |
| AR (1) | AR231398A1 (en) |
| AU (1) | AU569516B2 (en) |
| BE (1) | BE899331A (en) |
| BG (1) | BG49707A3 (en) |
| CH (1) | CH659386A5 (en) |
| CZ (1) | CZ262984A3 (en) |
| DD (1) | DD220782A5 (en) |
| DE (1) | DE3412868A1 (en) |
| DK (1) | DK165729C (en) |
| ES (1) | ES8502332A1 (en) |
| FI (1) | FI82603C (en) |
| FR (1) | FR2556964A1 (en) |
| GB (1) | GB2151920B (en) |
| GR (1) | GR79584B (en) |
| HU (1) | HU190924B (en) |
| IE (1) | IE57164B1 (en) |
| IL (1) | IL71470A (en) |
| IN (1) | IN160415B (en) |
| IS (1) | IS1364B6 (en) |
| IT (1) | IT1177655B (en) |
| LU (1) | LU85290A1 (en) |
| MA (1) | MA20088A1 (en) |
| MX (1) | MX7715E (en) |
| NO (1) | NO169575C (en) |
| NZ (1) | NZ207753A (en) |
| OA (1) | OA07700A (en) |
| PH (1) | PH21938A (en) |
| PL (1) | PL144356B1 (en) |
| PT (1) | PT78382B (en) |
| RO (1) | RO89437A (en) |
| SU (1) | SU1478993A3 (en) |
| YU (1) | YU44762B (en) |
| ZA (1) | ZA842573B (en) |
| ZM (1) | ZM2084A1 (en) |
| ZW (1) | ZW6084A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4806361A (en) * | 1984-06-04 | 1989-02-21 | Sterling Drug Inc. | Medicaments in sustained release unit dose form |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3678643D1 (en) * | 1985-08-16 | 1991-05-16 | Procter & Gamble | PARTICLES WITH CONSTANT RELEASE OF ACTIVE SUBSTANCES. |
| US4853229A (en) * | 1987-10-26 | 1989-08-01 | Alza Corporation | Method for adminstering tiny pills |
| JPH0791184B2 (en) * | 1988-03-31 | 1995-10-04 | 田辺製薬株式会社 | Controlled release formulation and process for producing the same |
| GB8903328D0 (en) * | 1989-02-14 | 1989-04-05 | Ethical Pharma Ltd | Nifedipine-containing pharmaceutical compositions and process for the preparation thereof |
| PH30929A (en) * | 1992-09-03 | 1997-12-23 | Janssen Pharmaceutica Nv | Beads having a core coated with an antifungal and a polymer. |
| FR2762213B1 (en) * | 1997-04-18 | 1999-05-14 | Synthelabo | PHARMACEUTICAL COMPOSITION WITH GASTRIC RETENTION |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1472025A (en) * | 1964-01-13 | 1967-03-10 | Merck & Co Inc | Manufacturing process of new heterocyclic benzamides |
| FR2313915A1 (en) * | 1976-01-26 | 1977-01-07 | Corneille Gilbert | Sustained release vincamine microcapsules - with inert core, vincamine (deriv.) intermediate layer and microporous outer coating |
| FR2453642A1 (en) * | 1979-04-12 | 1980-11-07 | Sanofi Sa | Controlled release of ergo-toxin methane sulphonate - from micro-granules coated with anionic and cationic methacrylic! polymers and a plasticiser |
| GB2047096A (en) * | 1979-04-09 | 1980-11-26 | Sanofi Sa | Naftidrofuryl composition for immediate and delayed release |
| WO1981001652A1 (en) * | 1979-12-07 | 1981-06-25 | D Panoz | Improvements to methods for preparing galenical preparation with delayed action and programmed release and galenical preparations for drugs obtained thereby |
| WO1982001468A1 (en) * | 1980-10-28 | 1982-05-13 | Claude Laruelle | New galenical administration form of metoclopramide,method for its preparation and medicament comprising this new form |
| WO1982001649A1 (en) * | 1980-11-19 | 1982-05-27 | Laruelle Claude | New galenic preparation of phenofibrate,method for the obtention thereof,its application as a medicine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4285665A (en) * | 1978-05-08 | 1981-08-25 | Johnson, Matthey & Co., Limited | Engines |
| FR2454804B1 (en) * | 1979-04-26 | 1986-11-21 | Sanofi Sa | DIHYDROERGOTOXIN-BASED MEDICINAL PRODUCT AND PROCESS FOR PREPARING THE SAME |
| SE8003805L (en) * | 1980-05-21 | 1981-11-22 | Haessle Ab | A PHARMACEUTICAL PREPARATION WITH IMPROVED EMISSION PROPERTY |
| JPS5753326A (en) * | 1980-09-17 | 1982-03-30 | Dainippon Printing Co Ltd | Manufacture of biaxially stretching blow molded vessel of saturated polyester |
| FR2534139B1 (en) * | 1982-10-07 | 1986-08-29 | Laruelle Claude | NOVEL GALENIC FORM OF SULPIRIDE, METHOD FOR PREPARING SAME, AND MEDICINAL PRODUCT COMPRISING THIS NEW FORM |
-
1983
- 1983-12-23 FR FR8320635A patent/FR2556964A1/en not_active Withdrawn
-
1984
- 1984-03-30 IS IS2900A patent/IS1364B6/en unknown
- 1984-04-02 IE IE817/84A patent/IE57164B1/en not_active IP Right Cessation
- 1984-04-04 MA MA20309A patent/MA20088A1/en unknown
- 1984-04-04 EP EP84400661A patent/EP0147244A1/en not_active Withdrawn
- 1984-04-05 ZA ZA842573A patent/ZA842573B/en unknown
- 1984-04-05 DE DE19843412868 patent/DE3412868A1/en not_active Withdrawn
- 1984-04-05 NZ NZ207753A patent/NZ207753A/en unknown
- 1984-04-05 BE BE1/10992A patent/BE899331A/en not_active IP Right Cessation
- 1984-04-05 CZ CS842629A patent/CZ262984A3/en unknown
- 1984-04-06 IN IN242/MAS/84A patent/IN160415B/en unknown
- 1984-04-06 PL PL1984247098A patent/PL144356B1/en unknown
- 1984-04-06 CH CH1755/84A patent/CH659386A5/en not_active IP Right Cessation
- 1984-04-06 DD DD84261741A patent/DD220782A5/en not_active IP Right Cessation
- 1984-04-06 JP JP59069883A patent/JPS60139616A/en active Granted
- 1984-04-06 PH PH30510A patent/PH21938A/en unknown
- 1984-04-06 BG BG064985A patent/BG49707A3/en unknown
- 1984-04-06 OA OA58273A patent/OA07700A/en unknown
- 1984-04-06 FI FI841376A patent/FI82603C/en not_active IP Right Cessation
- 1984-04-06 AR AR296218A patent/AR231398A1/en active
- 1984-04-06 SU SU843728542A patent/SU1478993A3/en active
- 1984-04-06 GB GB08408978A patent/GB2151920B/en not_active Expired
- 1984-04-06 NO NO841367A patent/NO169575C/en unknown
- 1984-04-06 DK DK180784A patent/DK165729C/en not_active IP Right Cessation
- 1984-04-06 HU HU841362A patent/HU190924B/en not_active IP Right Cessation
- 1984-04-06 YU YU640/84A patent/YU44762B/en unknown
- 1984-04-06 LU LU85290A patent/LU85290A1/en unknown
- 1984-04-06 GR GR74337A patent/GR79584B/el unknown
- 1984-04-06 IT IT48001/84A patent/IT1177655B/en active
- 1984-04-06 PT PT78382A patent/PT78382B/en not_active IP Right Cessation
- 1984-04-07 KR KR1019840001840A patent/KR910004570B1/en not_active Expired
- 1984-04-07 RO RO84114201A patent/RO89437A/en unknown
- 1984-04-08 IL IL71470A patent/IL71470A/en unknown
- 1984-04-10 ZW ZW60/84A patent/ZW6084A1/en unknown
- 1984-04-16 MX MX84101994U patent/MX7715E/en unknown
- 1984-04-24 ZM ZM20/84A patent/ZM2084A1/en unknown
- 1984-05-03 ES ES532125A patent/ES8502332A1/en not_active Expired
- 1984-05-31 AU AU28904/84A patent/AU569516B2/en not_active Ceased
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1472025A (en) * | 1964-01-13 | 1967-03-10 | Merck & Co Inc | Manufacturing process of new heterocyclic benzamides |
| FR2313915A1 (en) * | 1976-01-26 | 1977-01-07 | Corneille Gilbert | Sustained release vincamine microcapsules - with inert core, vincamine (deriv.) intermediate layer and microporous outer coating |
| GB2047096A (en) * | 1979-04-09 | 1980-11-26 | Sanofi Sa | Naftidrofuryl composition for immediate and delayed release |
| FR2453642A1 (en) * | 1979-04-12 | 1980-11-07 | Sanofi Sa | Controlled release of ergo-toxin methane sulphonate - from micro-granules coated with anionic and cationic methacrylic! polymers and a plasticiser |
| WO1981001652A1 (en) * | 1979-12-07 | 1981-06-25 | D Panoz | Improvements to methods for preparing galenical preparation with delayed action and programmed release and galenical preparations for drugs obtained thereby |
| WO1982001468A1 (en) * | 1980-10-28 | 1982-05-13 | Claude Laruelle | New galenical administration form of metoclopramide,method for its preparation and medicament comprising this new form |
| WO1982001649A1 (en) * | 1980-11-19 | 1982-05-27 | Laruelle Claude | New galenic preparation of phenofibrate,method for the obtention thereof,its application as a medicine |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4806361A (en) * | 1984-06-04 | 1989-02-21 | Sterling Drug Inc. | Medicaments in sustained release unit dose form |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4459279A (en) | Retard form of pharmaceuticals with insoluble porous diffusion coatings | |
| CA1228546A (en) | Oral mopidamol preparations | |
| SU1151193A3 (en) | Method of obtaining dipyridamol peroral preparation | |
| US4524060A (en) | Slow release pharmaceutical composition | |
| IE60352B1 (en) | Press coated dhp tablets | |
| JP2881442B2 (en) | Slow-release acid-free pharmaceutical preparation of diltiazem and its preparation | |
| KR20160054216A (en) | Pharmaceutical tablet comprising Choline Alphoscerate and method for manufacturing the same | |
| CY1653A (en) | Pharmaceutical compositions with analgesic properties and the preparation and use thereof | |
| GB2151920A (en) | Oral compositions containing sulpiride | |
| US4777044A (en) | Therapeutic preparation having ammonium nitrate as its active substance | |
| EP0393572A2 (en) | Controlled release tablets containing flavoxate | |
| EP0416248A2 (en) | Use of vitamine B6 for reducing elevated serotonin levels | |
| CA2309542A1 (en) | Novel oral dosage form for carvedilol | |
| US4206214A (en) | Antithrombotic pharmaceutical compositions containing dipyridamole and sulfinpyrazone | |
| EP0145558B1 (en) | Galenic forms of sulpiride for oral administration | |
| US5077294A (en) | Products containing verapamil or gallopamil and prazosin | |
| EP1233758A2 (en) | Sodium valproate granulate with reduced hygroscopicity | |
| US3482021A (en) | Anti-phlogistic and analgesic compositions and methods for relieving inflammatory conditions | |
| US3784695A (en) | Production of an hypotensive effect with esters of gallic acid | |
| EP0219737A1 (en) | Preparation on the basis of a mixture |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |