DK167735B1 - FIXED PREPARATION CONTAINING AN ALUMINUM SALT OF A SUCCHAROSE SULFATESTER AND POLYETHYLENE LYCOL, AND PROCEDURE FOR PREPARING THE PREPARATION - Google Patents
FIXED PREPARATION CONTAINING AN ALUMINUM SALT OF A SUCCHAROSE SULFATESTER AND POLYETHYLENE LYCOL, AND PROCEDURE FOR PREPARING THE PREPARATION Download PDFInfo
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- DK167735B1 DK167735B1 DK218587A DK218587A DK167735B1 DK 167735 B1 DK167735 B1 DK 167735B1 DK 218587 A DK218587 A DK 218587A DK 218587 A DK218587 A DK 218587A DK 167735 B1 DK167735 B1 DK 167735B1
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- Prior art keywords
- tablets
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- acc
- aluminum salt
- sucralfate
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- 238000002360 preparation method Methods 0.000 title claims description 8
- -1 POLYETHYLENE Polymers 0.000 title claims description 5
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 239000004698 Polyethylene Substances 0.000 title 1
- 229920000573 polyethylene Polymers 0.000 title 1
- MNQYNQBOVCBZIQ-JQOFMKNESA-A sucralfate Chemical compound O[Al](O)OS(=O)(=O)O[C@@H]1[C@@H](OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](COS(=O)(=O)O[Al](O)O)O[C@H]1O[C@@]1(COS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)O1 MNQYNQBOVCBZIQ-JQOFMKNESA-A 0.000 claims description 21
- 229960004291 sucralfate Drugs 0.000 claims description 21
- 239000002202 Polyethylene glycol Substances 0.000 claims description 16
- 229920001223 polyethylene glycol Polymers 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 8
- 238000012360 testing method Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 5
- 229930006000 Sucrose Natural products 0.000 claims description 4
- 239000008247 solid mixture Substances 0.000 claims description 4
- 239000005720 sucrose Substances 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 3
- 230000001133 acceleration Effects 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 239000000725 suspension Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 208000007107 Stomach Ulcer Diseases 0.000 description 4
- 229940069428 antacid Drugs 0.000 description 4
- 239000003159 antacid agent Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 201000005917 gastric ulcer Diseases 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 210000004051 gastric juice Anatomy 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920003114 HPC-L Polymers 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000057297 Pepsin A Human genes 0.000 description 1
- 108090000284 Pepsin A Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 235000004252 protein component Nutrition 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000005303 weighing Methods 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Cephalosporin Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
i DK 167735 B1in DK 167735 B1
Opfindelsen angår et fast præparat indeholdende et aluminiumsalt af en saccharosesulfatester (almindelig kendt som sucralfat) og polyethylenglycol, .samt .en.-fremgangsmåde til fremstilling af et sådant sucralfatpræpa-5 rat. Ved fremgangsmåden ifølge opfindelsen blandes sucralfat med polyethylenglycol til opnåelse af forøget desintegrerbarhed og dispergerbarhed, hvilket gør sucralfat mere egnet som medicin.The invention relates to a solid composition containing an aluminum salt of a sucrose sulfate ester (commonly known as sucralfate) and polyethylene glycol, as well as to a process for preparing such sucralfate preparation. In the process of the invention, sucralfate is mixed with polyethylene glycol to give increased disintegrability and dispersibility, making sucralfate more suitable as a medicine.
Sucralfat anvendes i stor udstrækning til be-10 handling af mavesår, da det kan beskytte substratproteinet (evne til at beskytte maveslimhinden) og undertrykke aktiviteten af pepsin i mavesaft samt neutralisere syre indholdet i mavesaften. Det er almindeligt kendt, at sucralfat bindes kraftigt til protein-15 bestanddelen af vævet under et mavesår til dannelse af et lag, som kemisk beskytter det angrebne område mod mavevæskes kraftige fordøjelsesevne og derved fremmer helingsprocessen (Nakazawa, S. et al., Dig. Dis. Sci., 26, 297 (1981); og A. Ishimori et al., Igaku to 20 Yakugaku, 9,25 (1983).Sucralfate is widely used to treat gastric ulcers as it can protect the substrate protein (ability to protect the gastric mucosa) and suppress the activity of pepsin in gastric juice as well as neutralize the acid content of the gastric juice. It is well known that sucralfate binds strongly to the protein component of the tissue during a gastric ulcer to form a layer that chemically protects the affected area from the strong digestive power of the stomach and thereby promotes the healing process (Nakazawa, S. et al., Dig. Dis. Sci., 26, 297 (1981); and A. Ishimori et al., Igaku to Yakugaku, 9.25 (1983).
På den anden side er sucralfat uopløseligt i vand, og præparater af det skal nemt kunne désintegreres og dispergeres, for at de effektivt kan bindes til et område, der er angrebet af mavesår.On the other hand, sucralfate is insoluble in water, and preparations of it must be easily disintegrated and dispersed in order to effectively bind to an area affected by gastric ulcer.
25 Der er blevet udført forskellige undersøgelser for at udvikle et sucralfatpræparat med forbedret evne til at kunne desintegreres og dispergeres. Det har nu vist sig, at dette kan opnåes ved blanding af sucralfat ned polyethylenglycol. Opfindelsen bygger på denne op-30 dagelse.Various studies have been performed to develop a sucralfate preparation with improved ability to disintegrate and disperse. It has now been found that this can be achieved by mixing sucralfate with polyethylene glycol. The invention is based on this up-30 day.
Fra WO-A-8601406 (side 3, linie 8-14) kendes et præparat indeholdende sucralfat og polyethylenglycol.WO-A-8601406 (page 3, lines 8-14) discloses a composition containing sucralfate and polyethylene glycol.
Der er imidlertid tale om et vandigt suspensionspræparat indeholdende flydende polyethylenglycol.However, it is an aqueous suspension preparation containing liquid polyethylene glycol.
35 Fra H.P. Fielder: Lexikon der Hilfstoffe fur35 From H.P. Fielder: Lexikon der Hilfstoffe fur
Pharmazie, Kosmetik und angrenzenden Gebietes, vol. 2, 2. ed., side 726-731 (spec, side 729, 2. kolonne) er det kendt, at polyethylenglycol kan anvendes som hjælpemiddel iPharmazie, Kosmetik und angrenzenden Gebietes, vol. 2, 2nd ed., Pages 726-731 (spec, pages 729, second column), it is known that polyethylene glycol can be used as an aid in
urv ΙΌ/ /OO D Iurv ΙΌ // OO D I
2 tabletter indeholdende antacider, og vedrørende fremstillingen anføres det, at de antacide stoffer indføres i en smelte af polyethylenglycol (molvægt 3000-10000).2 tablets containing antacids, and regarding the preparation it is stated that the antacids are introduced into a melt of polyethylene glycol (molecular weight 3000-10000).
Der er her tale om egentlige antacider, hvortil sucral-5 fat ikke hører, idet det hører til de såkaldte mucosa-protektive midler med en anden virkningsmekanisme end antacider, jf. ovenfor.These are actual antacids which do not belong to sucralcate, as they belong to the so-called mucosa-protective agents with a different mechanism of action than antacids, cf. above.
Fig. 1 og 2 viser desintegrerings-og disperge-ringsprofilerne af sucralfatpræparater ifølge op-10 findelsen og af sammenligningspræparater.FIG. 1 and 2 show the disintegration and dispersion profiles of sucralfate compositions according to the invention and of comparative compositions.
Ved fremgangsmåden ifølge opfindelsen kan et su-cralfat blandes med 0,1 vægt% eller mere polyethylenglycol. Skønt den øvre grænse for mængden af polyethylenglycol ikke er kritisk, anvendes det sædvanligvis i en 15 mængde på mindre end 50 vægt%. Molekylvægten af den polyethylenglycol, som skal blandes med sulcralfatet, er ikke begrænset til nogen speciel værdi. Ved peroral administrering-tillader sucralfatpræparatet ifølge opfindelsen sucralfatet at 20 blive effektivt bundet til det af mavesår angrebne område. Sucralfatpræparatet ifølge opfindelsen kan formuleres i forskellige doseringsformer, såsom pulvere, fint granulat, granulat, tabletter og kapsler. Til dette formål kan anvendes forskellige tilsætningsstoffer, 25 såsom bindemidler, desintegreringsmidler, smøremidler, fortyndingsmidler og farvestoffer.In the process of the invention, a sucralfate can be mixed with 0.1% by weight or more of polyethylene glycol. Although the upper limit of the amount of polyethylene glycol is not critical, it is usually used in an amount of less than 50% by weight. The molecular weight of the polyethylene glycol to be mixed with the sulcral phosphate is not limited to any particular value. By oral administration, the sucralfate composition of the invention allows the sucralfate to be effectively bonded to the area affected by gastric ulcer. The sucralfate composition of the invention may be formulated in various dosage forms such as powders, fine granules, granules, tablets and capsules. For this purpose, various additives such as binders, disintegrants, lubricants, diluents and dyes can be used.
Opfindelsen belyses nærmere ved hjælp af de følgende eksempler.The invention is further illustrated by the following examples.
30 EKSEMPEL 1EXAMPLE 1
Et aluminiumsalt af saccharosesulfatester (sucralfat: 3920 g) blev omhyggeligt blandet med 2000 g af en vandig opløsning af 4% polyethylenglycol 35 (molvægt 1500) i et blandeapparat. Blandingen blev granuleret i en cylindrisk granulator forsynet med et net med maskestørrelse på 0,7 mm55. Granulatet blev tørret ved 3 DK 167735 B1 60°C i 3 timer i et tørreskab med bakker. Det tørrede granulat blev sigtet gennem en 16-mesh sigte til opnåelse af små korn. Små korn til sammenligning blev fremstillet ved samme fremgangsmåde som ovenfor, 5 bortset fra at den vandige opløsning af 4% polyethylen-glycol blev erstattet med vand.An aluminum salt of sucrose sulfate ester (sucralfate: 3920 g) was carefully mixed with 2000 g of an aqueous solution of 4% polyethylene glycol 35 (molecular weight 1500) in a mixer. The mixture was granulated in a cylindrical granulator fitted with a mesh of 0.7 mm55 mesh. The granulate was dried at 60 ° C for 3 hours in a tray drying cabinet. The dried granules were sieved through a 16-mesh sieve to obtain small grains. Comparable small grains were prepared by the same procedure as above except that the aqueous solution of 4% polyethylene glycol was replaced with water.
Evnen til at kunne desintegreres og dispergeres for de 2 prøver af små korn er vist i fig. 1 udtrvkt som den ændring i uklarhed som optrådte, når værdien af en 10 kontrolsuspension blev sat til 1. Kontrol suspensionen blev fremstillet ved grundig dispergering af 1 g sucralfat i 1000 ml vand med ultralyd, og uklarheden af denne kontrolsuspension blev målt ved 540 nm med en lagtykkelse i detektorcellen på 1 cm. Måling af uklar-15 hed er beskrevet nærmere nedenfor: suspensioner hver indeholdende 200 mg sucralfat blev anbragt i 5 rør i et apparat til afprøvning af_ desintegration (testvæske: 1000 ml vand ved 37 - 2°C) og uklarhederne af væskeprøver udtaget ca. 5 cm under 20 overfladen af testvæskerne blev målt. På grundlag af de opnåede resultater blev de specifikke uklarheder af de enkelte prøver derefter beregnet.The ability to disintegrate and disperse for the 2 samples of small grains is shown in FIG. 1 expressed as the change in cloudiness that occurred when the value of a 10 control suspension was added to 1. The control suspension was prepared by thoroughly dispersing 1 g of sucralfate in 1000 ml of ultrasonic water and the turbidity of this control suspension was measured at 540 nm with a layer thickness in the detector cell of 1 cm. Measurement of cloudiness is described in more detail below: suspensions each containing 200 mg of sucralfate were placed in 5 tubes in a disintegration test apparatus (test liquid: 1000 ml of water at 37 - 2 ° C) and the cloud samples of liquid samples taken approx. 5 cm below the surface of the test fluids was measured. Based on the results obtained, the specific ambiguities of the individual samples were then calculated.
De to prøver af små korn blev underkastet en accelereret prøvning ved 40°C og 75% relativ fugtighed 25 16 måneder, og deres dispersionsgrad blev bedømt ved hjælp af specifik uklarhed, som blev beregnet som beskrevet ovenfor. Resultaterne er vist i tabel 1.The two samples of small grains were subjected to an accelerated test at 40 ° C and 75% relative humidity for 25 months, and their degree of dispersion was assessed by specific turbidity calculated as described above. The results are shown in Table 1.
Tabel 1 20 Ændring i specifik uklarhed p.g.a. accelerering ved 40°C og 75% relativ fugtighed i 6 månederTable 1 20 Change in specific obscurity due to acceleration at 40 ° C and 75% relative humidity for 6 months
Prøve tid: 2 min. 5 min. 20 min.Sample time: 2 min. 5 min. 20 min.
Små korn ifølge før acc._0,93 0,95 0,96 35 eksempel 1_efter acc._0,85 0,92 0,95Small grains according to before acc. 0.93 0.95 0.96 Example 1 after acc. 0.85 0.92 0.95
Små korn til før acc._0,28_0,33_0,41 sammenligning efter acc. 0,16 0,18 0,19 DK 167735 Bl 4Small grains for before acc._0,28_0,33_0.41 comparison after acc. 0.16 0.18 0.19 DK 167735 Bl 4
Tallene viser den betydelig bedre desintegrerbar-hed og dispergerbarhed, som udvises af kornene . i det faste præparat ifølge opfindelsen.The figures show the significantly better disintegrability and dispersibility exhibited by the grains. in the solid composition of the invention.
5 EKSEMPEL 2 4.000 g sucralfat blev omhyggeligt blandet med 2.000 g af en vandig opløsning af 10% polyethylengly-col (mol vægt 6.000) i et blandéapparat. Blandingen 10 blev sigtet gennem en 16-mesh sigte til fremstilling af et granulat, som blev tørret ved 60°C i 3 timer i tørreskab med bakker og klasificeret ved passage gennem en 10-mesh sigte.EXAMPLE 2 4,000 g of sucralfate was carefully mixed with 2,000 g of an aqueous solution of 10% polyethylene glycol (mole weight 6,000) in a blender. Mixture 10 was sieved through a 16 mesh screen to produce a granulate which was dried at 60 ° C for 3 hours in a tray drying cabinet and classified by passage through a 10 mesh screen.
De resulterende små korn (4.000 g) blev blandet 15 med 1.376 g krystallinsk cellulose og 24 g magnesium-stearat, og der blev blandet i 5 minutter i et blande-apparat af V-type.The resulting small grains (4,000 g) were mixed with 1,376 g of crystalline cellulose and 24 g of magnesium stearate and mixed for 5 minutes in a V-type mixer.
Det resulterende pulver blev anbragt i en roterende tabletmaskine forsynet med forme og stempler 20 (12 mm^) og presset under et totalt tryk på ca. 2,5 ton til opnåelse af tabletter hver af en vægt på 700 mg.The resulting powder was placed in a rotary tablet machine provided with molds and pistons 20 (12 mm 2) and pressed under a total pressure of approx. 2.5 tons to obtain tablets each weighing 700 mg.
Tabletter til sammenligning blev fremstillet på samme måde som beskrevet ovenfor, bortset- fra at den vandige opløsning af 10% polyethylenglycol blev 25 erstattet med en vandig opløsning af 10% hydroxypro-pyl cellulose (Nisso HPC-L fra Nippon Soda Co., Ltd.)Comparative tablets were prepared in the same manner as described above except that the aqueous solution of 10% polyethylene glycol was replaced with an aqueous solution of 10% hydroxypropyl cellulose (Nisso HPC-L from Nippon Soda Co., Ltd. )
Evnen til at kunne desintegreres og dispergeres af de to tabletprøver er vist i fig. 2 som den ændring 1 uklarhed som optrådte, når værdien af en kontrol-30 suspension blev sat til 1. Kontrolsuspensionen blev fremstillet ved grundig dispergering af 1.000 mg sucralfat, 344 mg krystallinsk cellulose og 6 mg mågnesiumstearat i 1.000 ml vand med ultralyd, og uklarheden af denne kontrolsuspension blev målt ved 540 nm 35 i en derektorcelle med en lagtykkelse på 1 cm. Målinger af uklarheder er beskrevet mere specielt nedenfor: 2 tabletter fra hver prøve blev anbragt i et apparat til afprøvning af desintegration (testvæske: 1.000 mlThe ability to disintegrate and disperse by the two tablet samples is shown in FIG. 2 as the change 1 blur that occurred when the value of a control suspension was set to 1. The control suspension was prepared by thoroughly dispersing 1,000 mg sucralfate, 344 mg crystalline cellulose and 6 mg magnesium stearate in 1,000 ml water with ultrasound, and the blur of this control suspension was measured at 540 nm 35 in a detector cell with a layer thickness of 1 cm. Measurements of cloudiness are described more specifically below: 2 tablets from each sample were placed in a disintegration test apparatus (test liquid: 1,000 ml
Claims (2)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9990186 | 1986-04-30 | ||
| JP9990186 | 1986-04-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK218587D0 DK218587D0 (en) | 1987-04-29 |
| DK218587A DK218587A (en) | 1987-10-31 |
| DK167735B1 true DK167735B1 (en) | 1993-12-13 |
Family
ID=14259677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK218587A DK167735B1 (en) | 1986-04-30 | 1987-04-29 | FIXED PREPARATION CONTAINING AN ALUMINUM SALT OF A SUCCHAROSE SULFATESTER AND POLYETHYLENE LYCOL, AND PROCEDURE FOR PREPARING THE PREPARATION |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JP2542210B2 (en) |
| DE (1) | DE3714159C2 (en) |
| DK (1) | DK167735B1 (en) |
| ES (1) | ES2017805A6 (en) |
| FI (1) | FI89457C (en) |
| FR (1) | FR2598084B1 (en) |
| IT (1) | IT1208416B (en) |
| NO (1) | NO174085C (en) |
| SE (1) | SE503233C2 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2735559B2 (en) * | 1988-03-02 | 1998-04-02 | 中外製薬株式会社 | Suspension |
| ATE213635T1 (en) * | 1994-04-26 | 2002-03-15 | Chugai Pharmaceutical Co Ltd | METHOD FOR PRODUCING MELT-GRANULATED SUCRALFATE PREPARATION |
| US5968906A (en) * | 1995-02-02 | 1999-10-19 | Chugai Seiyaku Kabushiki Kaisha | Sucralfate preparations |
| ES2112765B1 (en) * | 1995-08-02 | 1999-03-01 | Cantabria Ind Farmaceutica Sa | PROCEDURE FOR OBTAINING RADIOLOGICAL CONTRAST FORMULATIONS, FOR GASTROINTESTINAL EXPLORATIONS FOR EXTEMPORARY AND DIRECT USE. |
| EP2540317A4 (en) * | 2010-02-22 | 2014-04-16 | Daiichi Sankyo Co Ltd | SOLID RELEASE PREPARATION FOR ORAL USE |
| WO2011102504A1 (en) | 2010-02-22 | 2011-08-25 | 第一三共株式会社 | Sustained-release solid preparation for oral use |
| KR102127625B1 (en) | 2012-09-03 | 2020-06-29 | 다이이찌 산쿄 가부시키가이샤 | Hydromorphone hydrochloride-containing oral sustained-release pharmaceutical composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3430809A1 (en) * | 1984-08-22 | 1986-03-06 | Merck Patent Gmbh, 6100 Darmstadt | SUCRALFAT SUSPENSION |
-
1987
- 1987-04-28 DE DE3714159A patent/DE3714159C2/en not_active Expired - Lifetime
- 1987-04-28 FI FI871852A patent/FI89457C/en not_active IP Right Cessation
- 1987-04-28 NO NO871759A patent/NO174085C/en unknown
- 1987-04-29 DK DK218587A patent/DK167735B1/en not_active IP Right Cessation
- 1987-04-29 IT IT8767365A patent/IT1208416B/en active
- 1987-04-29 SE SE8701787A patent/SE503233C2/en not_active IP Right Cessation
- 1987-04-29 ES ES8701280A patent/ES2017805A6/en not_active Expired - Lifetime
- 1987-04-30 FR FR878706196A patent/FR2598084B1/en not_active Expired - Lifetime
- 1987-04-30 JP JP62104612A patent/JP2542210B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63107933A (en) | 1988-05-12 |
| DK218587D0 (en) | 1987-04-29 |
| NO871759L (en) | 1987-11-02 |
| FI89457C (en) | 1993-10-11 |
| FR2598084A1 (en) | 1987-11-06 |
| NO174085B (en) | 1993-12-06 |
| NO871759D0 (en) | 1987-04-28 |
| IT1208416B (en) | 1989-06-12 |
| FI871852L (en) | 1987-10-31 |
| SE503233C2 (en) | 1996-04-22 |
| DK218587A (en) | 1987-10-31 |
| SE8701787L (en) | 1987-10-31 |
| FR2598084B1 (en) | 1991-04-26 |
| FI871852A0 (en) | 1987-04-28 |
| IT8767365A0 (en) | 1987-04-29 |
| JP2542210B2 (en) | 1996-10-09 |
| DE3714159A1 (en) | 1987-11-05 |
| FI89457B (en) | 1993-06-30 |
| SE8701787D0 (en) | 1987-04-29 |
| NO174085C (en) | 1994-03-16 |
| DE3714159C2 (en) | 1996-09-19 |
| ES2017805A6 (en) | 1991-03-01 |
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| Date | Code | Title | Description |
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| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |