WO1996025151A1 - Feste wirkstoff-zubereitungen - Google Patents
Feste wirkstoff-zubereitungen Download PDFInfo
- Publication number
- WO1996025151A1 WO1996025151A1 PCT/EP1996/000417 EP9600417W WO9625151A1 WO 1996025151 A1 WO1996025151 A1 WO 1996025151A1 EP 9600417 W EP9600417 W EP 9600417W WO 9625151 A1 WO9625151 A1 WO 9625151A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- naproxen
- water
- weight
- hydroxypropyl cellulose
- preparations according
- Prior art date
Links
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- 239000000155 melt Substances 0.000 claims abstract description 7
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- 239000004480 active ingredient Substances 0.000 claims description 24
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 9
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- 238000000034 method Methods 0.000 claims description 7
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- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 1
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- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
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- 229960000401 tranexamic acid Drugs 0.000 description 1
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 1
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
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- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-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
-
- 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
- A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
Definitions
- the present invention relates to solid preparations obtainable by joint melt extrusion of
- the invention further relates to a method for producing such preparations and their use as medicaments.
- JP-A 58-192817 and JP-A 58-79915 disclose the melt extrusion of preparations containing active ingredients based on thermoplastic polymers such as hydroxypropyl cellulose as binders.
- L-HPC Low-substituted hydroxypropyl cellulose
- L-HPC Low-substituted hydroxypropyl cellulose
- the object of the present invention was to find active substance preparations which can be produced by polymer-active substance melt extrusion and which allow a targeted adjustment of the active substance release.
- Suitable active ingredients are, for example:
- Vitamins such as vitamin C, ⁇ -carotene and other carotenoids or plant protection agents are also suitable as active ingredients.
- the active substances are preferably in the form of so-called “solid solutions”, i.e. distributed molecularly in the matrix, or in the form of a solid dispersion.
- the amount of active ingredient component A) in the overall preparation can vary within wide limits depending on the effectiveness and rate of release.
- the active substance content can be in the range from 0.1 to 90% by weight, preferably from 0.5 to 60% by weight, based on the overall preparation. The only condition is that the preparation can still be processed thermoplastically.
- the preparations according to the invention contain a mixture of polymer components B)
- Bl 10 to 90 wt .-%, preferably 20 to 80 wt .-% of a water-soluble, thermoplastic polymer
- water-soluble polymers B1) The following may be mentioned as water-soluble polymers B1):
- Alkyl celluloses such as methyl cellulose
- Hydroxyalkyl celluloses such as hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl cellulose,
- Hydroxyalkylalkyl celluloses such as hydroxyethylmethyl and hydroxypropylmethyl cellulose
- Carboxyalkyl celluloses such as carboxymethyl celluloses
- Polysaccharides such as alginic acid and its alkali and ammonium salts,
- Component B1 should soften or melt in the total mixture of all components in the range from 50 to 180 ° C., preferably 60 to 150 ° C., so that the mass can be extruded.
- the glass transition temperature of the polymers should accordingly be below 180 ° C.
- Water-soluble means that at least 0.5 g, preferably at least 2 g, of the polymer dissolve in 100 g of water at 20 ° C., possibly also colloidally.
- Hydroxypropyl cellulose with a molar degree of substitution of 3.0 to 4.4 is preferably used as polymer component A).
- Component B2) according to the invention is a low-substituted hydroxypropyl cellulose with a molar degree of substitution of 0.5 to 2, preferably 1.5 to 1.8, the so-called low-substituted hydroxypropyl cellulose (L-HPC) as described in US Pharmacopoeia / NF XVII and the Japanese pharmacopoeia JP XI.
- L-HPC low-substituted hydroxypropyl cellulose
- Such L-HPC is water-insoluble, but water-swellable and does not behave thermoplastic.
- the amount of component B2) used preferably depends on what active ingredient release rate is desired. In the event of rapid release, the use of smaller amounts is recommended, for example 5 to 30% by weight. In the event that a delayed release of active ingredient is desired, the use of 30 to 90% by weight of B2) is recommended.
- the grain size of the L-HPC used is not critical according to the invention.
- fillers e.g. the oxides of magnesium, aluminum, silicon and titanium as well as lactose, mannitol, sorbitol, xylitol, pentaerythritol and its derivatives, the amount of filler being about 0.02 to 50, preferably 0.2 to 20,% by weight .-% lies.
- Flow regulators which may be mentioned are, for example, the mono-, di- and triglycerides of long-chain fatty acids such as C 12 -, C 1 -, C 6 and C 8 -fatty acid, waxes such as Camauba wax and the lecithins, the amount being about 0 , 1 to 30, preferably 0.1 to 5 wt .-%.
- plasticizers for example in addition to low molecular weight polyalkylene oxides such as polyethylene glycol, polypropylene glycol and polyethylene propylene glycol.
- the amount of plasticizer is about 0.5 to 15, preferably 0.5 to 5 wt .-%.
- lubricants which may be mentioned are stearates of aluminum or calcium, as well as talc and silicones, their amount being about 0.1 to 5, preferably 0.1 to 3,% by weight.
- stabilizers are light stabilizers,
- Antioxidants, radical scavengers and stabilizers against microbial attack are mentioned, the amount of which is preferably about 0.01 to 0.05% by weight.
- the active ingredient component can either be melted directly in the form of a physical mixture with the polymers B or mixed with the polymer melt already present.
- component A) is mixed with the
- the active ingredient-containing polymer melt can be shaped, for example, by calendering the extrudate by the method described in EP-A 240 906 and by the processing method known from DE-A 38 30 355 by comminuting the extrudate with rotating knives in the same volume - still deformable - pieces with a solidified surface and then pressed into tablets in the usual tableting machines.
- auxiliary substances can be incorporated into the polymer melt together with the active ingredient.
- Mixtures of auxiliaries, the active ingredient and the polymers B can also be melted directly. In general, it is common to fuse together a physical mixture of auxiliaries, active ingredients and the polymers B.
- the preparations according to the invention are used as medicaments and are used in the form of tablets, pellets, granules or capsules.
- Pharmaceutical forms with delayed active ingredient release are preferably produced with the preparations according to the invention.
- the solid pharmaceutical form can also be provided with a customary coating to improve the appearance and / or taste (dragee) or to further delay the release of the active ingredient.
- a customary coating to improve the appearance and / or taste (dragee) or to further delay the release of the active ingredient.
- the tablet is produced in a closed-cell porous form according to one of the known techniques, so that it floats in the stomach and thus remains there for a longer time.
- the present invention enables a targeted adjustment of the active ingredient release profile of the solid dosage forms according to the invention, in particular in the manufacture of solid dosage forms with delayed release of the active ingredient. Surprisingly, this succeeds regardless of the particle size of the L-HPC and process parameters during shaping.
- the amounts of active ingredient and the polymers B1) and B2) given in the table were mixed, introduced into a twin-screw extruder (ZSK 30, Werner & Pfleiderer) and extruded over 5 temperature zones.
- the temperatures of the individual temperature zones ("shots" 1-5) are given in Table I.
- the melt strands emerging via the extruder die bar were pelletized by air-cooled hot cutting with a knife roller granulator.
- the drug release was measured using the paddle method according to USP XXI, US pharmacopoeia. This in vitro method is used to determine the dissolution rate of active substance-containing formations (e.g. tablets, pellets, etc.).
- Hydroxypropyl cellulose with a molar degree of substitution from 3.0 to 4.4 (Klucel EF, Hercules, USA)
- Hydroxypropyl cellulose with a molar degree of substitution from 1.5 to 1.8 (LH 31, Shin-Etsu Chemical Comp. Ltd. Japan)
Abstract
Description
Claims
Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT96903958T ATE220541T1 (de) | 1995-02-14 | 1996-02-01 | Feste wirkstoff-zubereitungen |
CA002211033A CA2211033C (en) | 1995-02-14 | 1996-02-01 | Solid active compound preparations |
DE59609451T DE59609451D1 (de) | 1995-02-14 | 1996-02-01 | Feste wirkstoff-zubereitungen |
AU47860/96A AU4786096A (en) | 1995-02-14 | 1996-02-01 | Solid active agent preparations |
NZ302243A NZ302243A (en) | 1995-02-14 | 1996-02-01 | Solid active preparation obtained by joint melt extrusion of active compound(s), water soluble polymer and water-insoluble hydroxypropylcellulose |
US08/875,514 US5939099A (en) | 1995-02-14 | 1996-02-01 | Solid active extrusion compound preparations containing low-substituted hydroxypropylcellulose |
SK1043-97A SK104397A3 (en) | 1995-02-14 | 1996-02-01 | Solid active agent preparations |
PL96321755A PL321755A1 (en) | 1995-02-14 | 1996-02-01 | Soil preparations of active substances |
DK96903958T DK0809488T3 (da) | 1995-02-14 | 1996-02-01 | Faste formuleringer af aktivt stof |
EP96903958A EP0809488B1 (de) | 1995-02-14 | 1996-02-01 | Feste wirkstoff-zubereitungen |
JP52461596A JP4049810B2 (ja) | 1995-02-14 | 1996-02-01 | 固体の作用物質製剤 |
BR9606957A BR9606957A (pt) | 1995-02-14 | 1996-02-01 | Preparação sólida processo para sua produção uso da mesma e forma farmacéutica sólida |
BG101781A BG101781A (en) | 1995-02-14 | 1997-07-17 | Active substance-containing solid preparation |
FI973320A FI973320A (fi) | 1995-02-14 | 1997-08-13 | Kiinteitä aktiiviainetta sisältäviä valmisteita |
NO973730A NO973730L (no) | 1995-02-14 | 1997-08-13 | Faste virkestofftilberedninger |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19504832.6 | 1995-02-14 | ||
DE19504832A DE19504832A1 (de) | 1995-02-14 | 1995-02-14 | Feste Wirkstoff-Zubereitungen |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996025151A1 true WO1996025151A1 (de) | 1996-08-22 |
Family
ID=7753890
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1996/000417 WO1996025151A1 (de) | 1995-02-14 | 1996-02-01 | Feste wirkstoff-zubereitungen |
Country Status (25)
Country | Link |
---|---|
US (1) | US5939099A (de) |
EP (1) | EP0809488B1 (de) |
JP (1) | JP4049810B2 (de) |
KR (1) | KR19980702193A (de) |
CN (1) | CN1177584C (de) |
AT (1) | ATE220541T1 (de) |
AU (1) | AU4786096A (de) |
BG (1) | BG101781A (de) |
BR (1) | BR9606957A (de) |
CA (1) | CA2211033C (de) |
CZ (1) | CZ239497A3 (de) |
DE (2) | DE19504832A1 (de) |
DK (1) | DK0809488T3 (de) |
ES (1) | ES2180738T3 (de) |
FI (1) | FI973320A (de) |
HU (1) | HUP9702424A3 (de) |
IL (1) | IL117112A0 (de) |
NO (1) | NO973730L (de) |
NZ (1) | NZ302243A (de) |
PL (1) | PL321755A1 (de) |
PT (1) | PT809488E (de) |
SK (1) | SK104397A3 (de) |
TR (1) | TR199700786T1 (de) |
WO (1) | WO1996025151A1 (de) |
ZA (1) | ZA961137B (de) |
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- 1996-02-01 CZ CZ972394A patent/CZ239497A3/cs unknown
- 1996-02-01 DK DK96903958T patent/DK0809488T3/da active
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- 1996-02-01 SK SK1043-97A patent/SK104397A3/sk unknown
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- 1996-02-01 WO PCT/EP1996/000417 patent/WO1996025151A1/de active IP Right Grant
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WO1997012604A1 (de) * | 1995-09-29 | 1997-04-10 | Basf Aktiengesellschaft | Verfahren zur herstellung von vitaminhaltigen festen zubereitungen |
DE19916383A1 (de) * | 1999-03-31 | 2000-10-05 | Schering Ag | Pharmazeutische Zusammensetzung mit einem Extrusionsstoff |
WO2001007015A2 (de) * | 1999-07-23 | 2001-02-01 | Bayer Aktiengesellschaft | Schnellfreisetzende extrudate und verfahren zu ihrer herstellung sowie daraus erhältliche zubereitungen |
WO2001007015A3 (de) * | 1999-07-23 | 2001-12-06 | Bayer Ag | Schnellfreisetzende extrudate und verfahren zu ihrer herstellung sowie daraus erhältliche zubereitungen |
US6569455B1 (en) | 1999-07-23 | 2003-05-27 | Bayer Aktiengesellschaft | Quick-release extrudates, method for preparing the same and compositions obtained from said extrudates |
EP3141248A1 (de) | 2006-03-24 | 2017-03-15 | Auxilium International Holdings, Inc. | Stabilisierte zusammensetzungen mit basischen, labilen wirkstoffen |
WO2012085236A1 (en) | 2010-12-23 | 2012-06-28 | Abbott Gmbh & Co. Kg | Solid retard formulations based on solid dispersions |
Also Published As
Publication number | Publication date |
---|---|
TR199700786T1 (xx) | 1998-02-21 |
ES2180738T3 (es) | 2003-02-16 |
CA2211033C (en) | 2005-04-26 |
FI973320A0 (fi) | 1997-08-13 |
ZA961137B (en) | 1997-09-16 |
EP0809488B1 (de) | 2002-07-17 |
PL321755A1 (en) | 1997-12-22 |
BG101781A (en) | 1998-03-31 |
EP0809488A1 (de) | 1997-12-03 |
BR9606957A (pt) | 1997-10-28 |
DE19504832A1 (de) | 1996-08-22 |
US5939099A (en) | 1999-08-17 |
NZ302243A (en) | 1999-01-28 |
FI973320A (fi) | 1997-10-13 |
JP4049810B2 (ja) | 2008-02-20 |
KR19980702193A (ko) | 1998-07-15 |
CN1177584C (zh) | 2004-12-01 |
ATE220541T1 (de) | 2002-08-15 |
DK0809488T3 (da) | 2002-09-02 |
DE59609451D1 (de) | 2002-08-22 |
NO973730D0 (no) | 1997-08-13 |
IL117112A0 (en) | 1996-06-18 |
PT809488E (pt) | 2002-11-29 |
CZ239497A3 (cs) | 1998-01-14 |
HUP9702424A2 (hu) | 1998-06-29 |
NO973730L (no) | 1997-08-13 |
CN1174503A (zh) | 1998-02-25 |
AU4786096A (en) | 1996-09-04 |
SK104397A3 (en) | 1998-04-08 |
HUP9702424A3 (en) | 2001-03-28 |
CA2211033A1 (en) | 1996-08-22 |
JPH10513477A (ja) | 1998-12-22 |
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