NO156153B - PROCEDURE FOR PREPARING A PHARMACEUTICAL PREPARATION WITH LONG-TERM RELEASE. - Google Patents
PROCEDURE FOR PREPARING A PHARMACEUTICAL PREPARATION WITH LONG-TERM RELEASE. Download PDFInfo
- Publication number
- NO156153B NO156153B NO810062A NO810062A NO156153B NO 156153 B NO156153 B NO 156153B NO 810062 A NO810062 A NO 810062A NO 810062 A NO810062 A NO 810062A NO 156153 B NO156153 B NO 156153B
- Authority
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- Norway
- Prior art keywords
- dispersant
- polyolefin
- weight
- heating
- double bonds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 230000007774 longterm Effects 0.000 title 1
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 229920000098 polyolefin Polymers 0.000 claims description 21
- 239000002270 dispersing agent Substances 0.000 claims description 18
- -1 alkyl radical Chemical class 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 150000001451 organic peroxides Chemical class 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 150000002898 organic sulfur compounds Chemical class 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 150000003377 silicon compounds Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 2
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- ARNIBHATWCFIIK-UHFFFAOYSA-N dodecyl 3-sulfanylpropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCS ARNIBHATWCFIIK-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
Description
Fremgangsmåte til avmetning av dobbeltbindinger i polyolefiner. Procedure for desaturating double bonds in polyolefins.
Det er kjent at man i henhold til den såkalte lavtrykks-polyraeriseringsmetode kan fremstille høymolekylære polyolefiner med gunstige egenskaper. Disse produkter lar seg videre bearbeide til f.eks. tråder, folier og andre formlegemer. Ved siden av sin store styrke, motstandsevne overfor kjemikalier og andre fordelaktige egenskaper, oppviser polyolefinene imidlertid en lav stabilitet overfor oksydative angrep, særlig når polyolefinet samtidig utsettes for varme eller UV-bestråling. De beskadigelser som polyolefinene får under slike betingelser, skyldes bl.a. dobbeltbindinger i kjede-molekylene. Etter de erfaringer man har hittil, synes det ikke å It is known that, according to the so-called low-pressure polymerization method, high molecular weight polyolefins with favorable properties can be produced. These products can be further processed into e.g. threads, foils and other shaped bodies. Alongside their great strength, resistance to chemicals and other advantageous properties, the polyolefins, however, exhibit a low stability against oxidative attack, especially when the polyolefin is simultaneously exposed to heat or UV radiation. The damage that the polyolefins get under such conditions is due, among other things, to double bonds in the chain molecules. Based on the experiences one has had so far, it does not seem to
være mulig å unngå dannelsen av dobbeltbindinger ved polymeriseringen. be possible to avoid the formation of double bonds during the polymerization.
Derfor har man anstrengt seg for å gi det ferdige polymerisat en etterbehandling, hvorved oppnås en metning av dobbéltbindingene og dermed en økning av polyolefinenes stabilitet. Efforts have therefore been made to give the finished polymer a post-treatment, whereby a saturation of the double bonds is achieved and thus an increase in the stability of the polyolefins.
Por dette formål har man gjennomført en behandling med silisiumforbindelser, hvortil det var bundet minst ett H-atom umiddelbart på Si-atomet. I henhold til denne kjente metode må polyolefinene løses opp og røres i lengere tid sammen med silisiumforbindelsen og en egnet katalysator. Bortsett fra at det til dette trenges betraktelige mengder oppløsnings- og fellingsmidler, krever metoden meget arbeide, idet man etter den egentlige behandling må foreta en utfelling og rensing av polymerisatet. Ifølge et alternativ kan behandlingen imidlertid også foretas på den måte at polyolefinet blandes med en silisiumforbindelse ved høyere temperaturer, f.eks. 250-300°C, i et ekstruderingsapparat. Ved denne fremgangmåte kan man ikke oppnå noen jevn stabilisering. Dessuten finnes overskudd av silisiumforbindelsen fortsatt i polymerisatet etter behandlingen, hvilket må sees som en ulempe. For this purpose, a treatment was carried out with silicon compounds, to which at least one H atom was bound immediately on the Si atom. According to this known method, the polyolefins must be dissolved and stirred for a longer time together with the silicon compound and a suitable catalyst. Apart from the fact that considerable amounts of dissolving and precipitating agents are needed for this, the method requires a lot of work, since after the actual treatment the polymer must be precipitated and purified. According to an alternative, however, the treatment can also be carried out in such a way that the polyolefin is mixed with a silicon compound at higher temperatures, e.g. 250-300°C, in an extrusion apparatus. With this method, no uniform stabilization can be achieved. Furthermore, an excess of the silicon compound is still found in the polymer after the treatment, which must be seen as a disadvantage.
I henhold til en annen fremgangsmåte forsøker man å løse problemet ved en hydrogenering av dobbeltbindingen. Polyolefinet blir i oppløsning, emulsjon eller suspensjon sammen med hydrogen ført gjennom et hydreringsapparat, hvori det blir bragt sammen med en egnet hydrogeneringskatalysator. Metoden krever ganske mye apparatur og tid, og er ikke egnet for behandling av store polyolefinmengder. Endelig har metoden også den ulempe, at hydreringskatalysatoren må fjernes, fordi den ellers ville forstyrre ved polyolefinets videre bearbeidelse. According to another method, an attempt is made to solve the problem by hydrogenating the double bond. The polyolefin in solution, emulsion or suspension together with hydrogen is passed through a hydrogenation apparatus, in which it is brought together with a suitable hydrogenation catalyst. The method requires quite a lot of equipment and time, and is not suitable for processing large quantities of polyolefin. Finally, the method also has the disadvantage that the hydrogenation catalyst must be removed, because it would otherwise interfere with the further processing of the polyolefin.
Oppfinnelsen vedrører en fremgangsmåte til avmetning av dobbeltbindinger i kjedemolekyler av polyolefiner ved oppvarmning av en dispersjon av renset polyolefinpulver i et inert hydrokarbon i nærvær av 0,1 - 1 vektprosent (referert til polyolefinet) av en forbindelse som er istand til å tilleire seg til dobbéltbindingene, The invention relates to a method for desaturating double bonds in chain molecules of polyolefins by heating a dispersion of purified polyolefin powder in an inert hydrocarbon in the presence of 0.1 - 1 percent by weight (referred to the polyolefin) of a compound which is capable of adhering to the double bonds ,
.frasugning av dispergeringsmidlet og flere gangers ettervasking av polyolefinet med dispergeringsmidlet, idet fremgangsmåten er karakterisert ved at man som tilleiringsdyktig forbindelse anvender en organisk svovelforbindelse med den generelle formel .extraction of the dispersant and several subsequent washings of the polyolefin with the dispersant, the method being characterized by the use of an organic sulfur compound with the general formula
H-S-R, H-S-R,
hvor R betyr en alkylrest med fra 1 til 18 C-atomer, en arylrest, where R means an alkyl radical with from 1 to 18 carbon atoms, an aryl radical,
en aralkyl- eller en cykloalkylrest eller en alkylestergruppe, an aralkyl or a cycloalkyl residue or an alkyl ester group,
og oppvarmer mellom 60°C og dispergeringsmidlets kokepunkt i nærvær av 0,01 - 0,1 vektprosent av et organisk peroksyd (vektprosent jav and heats between 60°C and the boiling point of the dispersant in the presence of 0.01 - 0.1% by weight of an organic peroxide (% by weight jav
polyolefin) i løpet av 30 minutter til 5 timer eller oppvarmer til mellom 20°C og dispergeringsmidlets kokepunkt under innvirkning av UV-lys i løpet av mellom 30 og 60 minutter under omrøring. polyolefin) during 30 minutes to 5 hours or heat to between 20°C and the boiling point of the dispersant under the influence of UV light during between 30 and 60 minutes with stirring.
Egnede svovelforbindelser er f.eks.: alifatiske merkaptaner fra 2-18 C-atomer, cykloheksylmerkaptan, tiofenol, benzylmerkaptan, merkaptoeddiksyremetylester, 3-merkaptopropionsyrelaurylester. På grunn av den meget ubehagelige lukt foretrekkes de tungtflyktige høymolekylære forbindelser. Suitable sulfur compounds are, for example: aliphatic mercaptans from 2-18 C atoms, cyclohexyl mercaptan, thiophenol, benzyl mercaptan, mercaptoacetic acid methyl ester, 3-mercaptopropionic acid lauryl ester. Due to the very unpleasant smell, the highly volatile high molecular weight compounds are preferred.
Brukbare organiske peroksyder er: di-t-butyl-peroksy, dibenzoyl, dikumyl-, diacetyl-, dilauroyl-, cykloheksanon-, metyl-etylketonperoksyd, t-butylperacetat, t-butylperacetat, t-butylperbenzoat, t-butylperbenzoat. Useful organic peroxides are: di-t-butyl peroxy, dibenzoyl, dicumyl, diacetyl, dilauroyl, cyclohexanone, methyl ethyl ketone peroxide, t-butyl peracetate, t-butyl peracetate, t-butyl perbenzoate, t-butyl perbenzoate.
Som dispergeringsmidler egner seg inerte hydrokarboner Inert hydrocarbons are suitable as dispersants
som pentan, heksan, heptan, bensin, benzen, toluen, cylen, dekalin, tetralin, dieselolje. Som dispergeringsmiddel foretrekkes lett-flyktige forbindelser på grunn av den lettere regenerering og fordi de raskere lar seg fjerne fra den polymere. such as pentane, hexane, heptane, gasoline, benzene, toluene, cylene, decalin, tetralin, diesel oil. As a dispersant, easily volatile compounds are preferred because of the easier regeneration and because they can be removed from the polymer more quickly.
Det kan i enkelte tilfeller være fordelaktig å arbeide In some cases, it can be advantageous to work
ved temperaturer som ligger over dispergeringsmidlets kokepunkt ved normaltrykk. I disse tilfeller må trykket forhøyes tilsvarende. at temperatures above the dispersant's boiling point at normal pressure. In these cases, the pressure must be increased accordingly.
Overfor'de kjente metoder frembyr foreliggende arbeids-måte den fordel at behandlingen av den polymere kan foretas umiddelbart i tilknytning til rensingen, i den samme apparatur hvori rensingen ble gjennomført. Samtlige av de dispergeringsmidler som er anvendelig til fremgangsmåten er også oppløsningsmidler som kan brukes ved rensingen. Det overskytende behandlingsmiddel kan fjernes ved avsugning og den polymere kan lett rense vasking ved dispergeringsmiddel. Det er her ikke nødvendig å rense polymerisatet for en heterogen katalysator, som ved den ovennevnte hydrogeneringsmetode. Compared to the known methods, the present working method offers the advantage that the treatment of the polymer can be carried out immediately in connection with the cleaning, in the same apparatus in which the cleaning was carried out. All of the dispersants that are applicable to the method are also solvents that can be used in the cleaning. The excess treatment agent can be removed by suction and the polymer can be easily cleaned by washing with a dispersant. It is not necessary here to purify the polymer for a heterogeneous catalyst, as in the above-mentioned hydrogenation method.
Fremgangsmåten skal belyses ved eksempler: The procedure must be illustrated by examples:
1. Peroksydkatalyse. 1. Peroxide catalysis.
I en 1 liters tohalskolbe med rører og tilbakeløpskjøler dispergeres under nitrogenatmosfære 100 g polypropylen, som er fremstilt ved anvendelse av en katalysator som består av trietyl-aluminium og TiCl^ og etter avsluttet polymerisering renset med heksan og deretter med saltsur metanol, vasket til nøytralitet og tørket. Det anvendes 600 ml dispergeringsmiddel (se tabellen). In a 1 liter two-necked flask with stirrer and reflux condenser, 100 g of polypropylene, which has been prepared using a catalyst consisting of triethylaluminum and TiCl^ and, after completion of polymerization, purified with hexane and then with hydrochloric acid methanol, washed to neutrality and then with hydrochloric acid methanol, is dispersed under a nitrogen atmosphere dried. 600 ml of dispersant is used (see the table).
Til dispersjonen settes peroksyd og behandlingsmiddel. Man opp- Peroxide and treatment agent are added to the dispersion. One up-
varmer under røring. Deretter suges dispergeringsmidlet fra, pulveret heats while stirring. The dispersant is then sucked off, the powder
vaskes to ganger med hver gang 100 ml dispergeringsmiddel, og tørkes under nitrogen i vakuum tørkeskap. Den tørre prøve er dermed ferdig til stabilitetsbestemmelse. washed twice with 100 ml dispersant each time, and dried under nitrogen in a vacuum drying cabinet. The dry sample is thus ready for stability determination.
2. UV- bestråling. 2. UV irradiation.
I en 1 liters tohalskolbe med rører og belyst med en kvikksølvlampe (70 W), dispergeres under nitrogenatmosfære 100 g polypropylen i 600 ml dispergeringsmiddel. Polypropylenet er'fremstilt som beskrevet i eksempel 1. Til dispersjonen settes behandlingsmiddel. Deretter settes røreren igang og UV-lampen slåes på. På In a 1 liter two-necked flask with stirrer and illuminated with a mercury lamp (70 W), disperse 100 g of polypropylene in 600 ml of dispersing agent under a nitrogen atmosphere. The polypropylene is produced as described in example 1. Treatment agent is added to the dispersion. The stirrer is then started and the UV lamp is switched on. On
grunn av lampens varmeutvikling kjøles kolben utenifra med vann. due to the heat generated by the lamp, the flask is cooled from the outside with water.
For å hindre en for sterk avbygning, blir lampen slått av i 5 min. perioder etter å ha brent i 2 minutters perioder. Deretter blir den polymere frasuget væske, vasket to ganger med hver gang 100 ml dispergeringsmiddel, tørket, og er ferdig til stabilitetsmåling. To prevent excessive degradation, the lamp is switched off for 5 min. periods after burning for 2 minute periods. Then, the polymeric aspirated liquid is washed twice with each time 100 ml of dispersant, dried, and is ready for stability measurement.
Data angående fremgangsmåten sees av følgende tabell: Data regarding the procedure can be seen from the following table:
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11143080A | 1980-01-11 | 1980-01-11 | |
| US06/194,453 US4308251A (en) | 1980-01-11 | 1980-10-17 | Controlled release formulations of orally-active medicaments |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO810062L NO810062L (en) | 1981-07-13 |
| NO156153B true NO156153B (en) | 1987-04-27 |
| NO156153C NO156153C (en) | 1987-08-05 |
Family
ID=26808896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO810062A NO156153C (en) | 1980-01-11 | 1981-01-09 | PROCEDURE FOR PREPARING A PHARMACEUTICAL PREPARATION WITH LONG-TERM RELEASE. |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS56103110A (en) |
| AT (1) | AT374681B (en) |
| AU (1) | AU542824B2 (en) |
| BE (1) | BE886998A (en) |
| CA (1) | CA1140466A (en) |
| CH (1) | CH646604A5 (en) |
| DE (1) | DE3100191A1 (en) |
| DK (1) | DK6181A (en) |
| ES (2) | ES8205353A1 (en) |
| FI (1) | FI76927C (en) |
| FR (1) | FR2473308B1 (en) |
| GB (1) | GB2067072B (en) |
| GR (1) | GR73843B (en) |
| IE (1) | IE50806B1 (en) |
| IN (1) | IN151913B (en) |
| IT (1) | IT1221041B (en) |
| LU (1) | LU83052A1 (en) |
| NL (1) | NL8100037A (en) |
| NO (1) | NO156153C (en) |
| NZ (1) | NZ195933A (en) |
| SE (1) | SE447450B (en) |
| ZA (1) | ZA81136B (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2496082A (en) * | 1947-05-24 | 1950-01-31 | Ashenfelter William | Scaffold structure |
| IT1144911B (en) * | 1981-03-19 | 1986-10-29 | Pharmatec Spa | CONTROLLED RELEASE PHARMACEUTICAL COMPOSITION CONTAINING IBUPROFEN |
| JPS59227817A (en) * | 1983-06-07 | 1984-12-21 | Toyo Jozo Co Ltd | Long-acting bredinin preparation for oral administration |
| JPH0662404B2 (en) * | 1983-06-14 | 1994-08-17 | シンテックス・ファーマシユーテイカルズ・インターナシヨナル・リミテツド | Controlled-release naproxen and naproxen sodium tablets |
| ZA836031B (en) * | 1983-08-16 | 1985-02-27 | Verex Lab | Constant release rate solid dosage theophylline formulation |
| ZA836030B (en) * | 1983-08-16 | 1985-02-27 | Verex Lab | Constant order release solid dosage indomethacin formulation and method of treating arthritis and other inflammatory conditions |
| US5385738A (en) * | 1983-10-14 | 1995-01-31 | Sumitomo Pharmaceuticals Company, Ltd. | Sustained-release injection |
| EP0138216B1 (en) * | 1983-10-14 | 1993-01-07 | Sumitomo Pharmaceuticals Company, Limited | Sustained-release ifn preparation for parenteral administration |
| US4855134A (en) * | 1983-10-14 | 1989-08-08 | Sumitomo Pharmaceuticals Company, Limited | Sustained-release preparation |
| US4774091A (en) * | 1983-10-14 | 1988-09-27 | Sumitomo Pharmaceuticals Company, Ltd. | Long-term sustained-release preparation |
| DE3688188T2 (en) * | 1985-12-27 | 1993-10-14 | Sumitomo Pharma | Process for the preparation of a sustained release formulation. |
| GB8601204D0 (en) * | 1986-01-18 | 1986-02-19 | Boots Co Plc | Therapeutic agents |
| US4968508A (en) * | 1987-02-27 | 1990-11-06 | Eli Lilly And Company | Sustained release matrix |
| NZ223619A (en) * | 1987-02-27 | 1990-10-26 | Lilly Co Eli | Sustained release tablet containing cefaclor, a hydrophilic polymer and an acrylic polymer |
| US5855915A (en) * | 1995-06-30 | 1999-01-05 | Baylor University | Tablets or biologically acceptable implants for long-term antiinflammatory drug release |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2953497A (en) * | 1953-06-03 | 1960-09-20 | Howard A Press | Therapeutic tablets |
| NL128902C (en) * | 1960-06-06 | |||
| US3577514A (en) * | 1968-06-10 | 1971-05-04 | Pfizer | Sustained release pharmaceutical tablets |
| US3773920A (en) * | 1971-07-14 | 1973-11-20 | Nikken Chemicals Co Ltd | Sustained release medicinal composition |
| US3906086A (en) * | 1971-07-19 | 1975-09-16 | Richard G Powers | Timed-release aspirin |
| GB1500300A (en) * | 1975-01-06 | 1978-02-08 | Ciba Geigy Ag | Pharmaceutical preparation for the treatment of circulatory disorders |
| JPS5411226A (en) * | 1977-06-24 | 1979-01-27 | Shin Etsu Chem Co Ltd | Disintegratable granule |
-
1980
- 1980-12-23 IN IN1418/CAL/80A patent/IN151913B/en unknown
- 1980-12-23 NZ NZ195933A patent/NZ195933A/en unknown
-
1981
- 1981-01-05 AU AU65976/81A patent/AU542824B2/en not_active Ceased
- 1981-01-06 FR FR8100087A patent/FR2473308B1/en not_active Expired
- 1981-01-07 DE DE19813100191 patent/DE3100191A1/en active Granted
- 1981-01-07 NL NL8100037A patent/NL8100037A/en not_active Application Discontinuation
- 1981-01-08 GB GB8100522A patent/GB2067072B/en not_active Expired
- 1981-01-08 DK DK6181A patent/DK6181A/en not_active Application Discontinuation
- 1981-01-08 ES ES498369A patent/ES8205353A1/en not_active Expired
- 1981-01-08 BE BE0/203426A patent/BE886998A/en unknown
- 1981-01-08 JP JP157881A patent/JPS56103110A/en active Pending
- 1981-01-08 CH CH9281A patent/CH646604A5/en not_active IP Right Cessation
- 1981-01-09 FI FI810056A patent/FI76927C/en not_active IP Right Cessation
- 1981-01-09 LU LU83052A patent/LU83052A1/en unknown
- 1981-01-09 CA CA000368219A patent/CA1140466A/en not_active Expired
- 1981-01-09 NO NO810062A patent/NO156153C/en unknown
- 1981-01-09 ZA ZA00810136A patent/ZA81136B/en unknown
- 1981-01-09 IE IE36/81A patent/IE50806B1/en unknown
- 1981-01-09 SE SE8100104A patent/SE447450B/en not_active IP Right Cessation
- 1981-01-09 AT AT0005481A patent/AT374681B/en not_active IP Right Cessation
- 1981-01-09 GR GR63828A patent/GR73843B/el unknown
- 1981-01-09 IT IT47537/81A patent/IT1221041B/en active
-
1982
- 1982-01-29 ES ES509179A patent/ES8301629A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3100191A1 (en) | 1981-12-10 |
| AT374681B (en) | 1984-05-25 |
| IT1221041B (en) | 1990-06-21 |
| ES509179A0 (en) | 1982-12-16 |
| GB2067072A (en) | 1981-07-22 |
| DE3100191C2 (en) | 1988-09-01 |
| FI810056L (en) | 1981-07-12 |
| JPS56103110A (en) | 1981-08-18 |
| CA1140466A (en) | 1983-02-01 |
| IT8147537A0 (en) | 1981-01-09 |
| NO156153C (en) | 1987-08-05 |
| ZA81136B (en) | 1982-01-27 |
| ATA5481A (en) | 1983-10-15 |
| NO810062L (en) | 1981-07-13 |
| DK6181A (en) | 1981-07-12 |
| AU542824B2 (en) | 1985-03-14 |
| ES498369A0 (en) | 1982-06-01 |
| NZ195933A (en) | 1982-11-23 |
| IN151913B (en) | 1983-09-03 |
| GB2067072B (en) | 1983-08-10 |
| FI76927C (en) | 1989-01-10 |
| IE50806B1 (en) | 1986-07-23 |
| GR73843B (en) | 1984-05-07 |
| FI76927B (en) | 1988-09-30 |
| IE810036L (en) | 1981-07-11 |
| LU83052A1 (en) | 1982-09-10 |
| CH646604A5 (en) | 1984-12-14 |
| ES8301629A1 (en) | 1982-12-16 |
| ES8205353A1 (en) | 1982-06-01 |
| NL8100037A (en) | 1981-08-03 |
| SE447450B (en) | 1986-11-17 |
| BE886998A (en) | 1981-07-08 |
| AU6597681A (en) | 1981-07-16 |
| FR2473308A1 (en) | 1981-07-17 |
| FR2473308B1 (en) | 1985-07-19 |
| SE8100104L (en) | 1981-07-12 |
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