CA2177721A1 - Taste masked composition containing a drug/polymer complex - Google Patents

Taste masked composition containing a drug/polymer complex

Info

Publication number
CA2177721A1
CA2177721A1 CA002177721A CA2177721A CA2177721A1 CA 2177721 A1 CA2177721 A1 CA 2177721A1 CA 002177721 A CA002177721 A CA 002177721A CA 2177721 A CA2177721 A CA 2177721A CA 2177721 A1 CA2177721 A1 CA 2177721A1
Authority
CA
Canada
Prior art keywords
chewable
taste masked
complex
therapeutic agent
drug
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.)
Abandoned
Application number
CA002177721A
Other languages
French (fr)
Inventor
Franco Francese
Massimo Maneschi
Diego Oldani
Tiziana Crolla
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GlaxoSmithKline SpA
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2177721A1 publication Critical patent/CA2177721A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6943—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a pill, a tablet, a lozenge or a capsule

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Zoology (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

A chewable taste masked formulation comprising a therapeutic agent (or drug) containing at least one basic group or atom optionally in the form of a salt, which is reacted with a polymer containing at least one acidic group to form a complex.

Description

TASTE MASKED COMPOSITION CONTAINING A DRUG/POLYMER COMPLEX
The presenl invention relates to therapeutic agent/polymer matrix complexes which have improved t. ste ~ a~Lli~Li~.
Many Ll~ ~r~ y active substances have an unpleasant taste or cause a numbing effect when adl~ L~I~d by mouth to a patient.
Many Lll~la~ uLic a~llL/L~ol~ cl~mh;no~ nc are known but the therapeutic âgent is coated with the polymer. The problem with such products is that Lhey are liable to be broken when orally ~ r ~d by the patient, palLi~ulally when chewed, thereby allowing the therapeutic agent to be in direct contact with the mouth, thus the toste and/or numbing sensation of the therapeutic agent is no longer effectively masked.
A further problem with Cv~01~ of methacrylic acid and methyl methacrylate is Lhat when complexed with therapeutic agents the product formed tends to be a gum.
One particular drug"~im ' yvl~ tu, is useful for treating the symptoms associated with travel sickness. ~;...~..llr,' has a numbing taste.
A preferred fnrrn~ th~n of dilh~.hydlilla~r~ is in the form of a chewing gum or a chewable tabiet which means that the ~u~ I coaLing techniques using 20 polymers such as anionic copolymers based on Illt:Llla.,-~liC acid and m~L~ Lha~lylat~ (such as Eudragit), are ineffective in masking the numbing tastebecause the ~ .lLi~llàl polymer coated ' ' y,' complex is broken down when chewed by the patient.
Another drug, paroxetine, is useful for the treatment of iPrr~.cci~m panic 25 disorders and obssessive ~ JUIi>i~. disorders. Paroxetine has an unplea~cant bitLer tashe.
The present invention provides a therapeutic z~,~l.L/yOI~ ,I complex with superior tash masking qualities and can be prepared as a powder which is more easily formulahd with otherexcipients to form cu,,~. I r~... -1-~;....~
Accordingly, the present invention provides a chewable tash masked r.... 1 ~ l " . C~ .g a Lh~ t;u~;~, agent (or drug) containing at least One basic - group or atom optionally in the form of a salt which is reachd with a polymer containing at least one acidic group to form a complex.
A preferred L~l~la~ agent is ~" ' ~lli-l~h or paroxetine.
The herm "basic group or atom" is understood to mean â group capable of donating electrons. Such groups include optionally substituhd amino groups or optionally substituted thio groups.
Suitable salts of therapeutic agents include acid addition salts which are suiLably rl ~ v~ lly acceptable salts such as the hydrochloride hemi-hydrahe for I

2l7772' wo 95/1515~ r~ 903 paroxetine.
It should ~e ~ .l that in cases where the dru~ comprises two active C~ i e- a basic one and an acidic one in the form of a salt, such as d~ yl' which is the 8-chlorotheophylline salt of ~i~)}lc~ ydl~ c then the S ter~n therapeutic agent in the form of a salt extends to both of tbese ~ F - ~Suitable polymers include pol~ l..t~," such as Eudragit L and S which are copolymers of ' ~1;-, acid and methyl l~ yld~C and have a mean molecular weight of about 135,000.
The term "acidic group" is understood to mean a group capable of receiving 10 electrons such as a carboxylic acid group.
The complexes of therapeutic agent (including salts thereof) with polymers can be in different weight ratios. For paroxetine and dimenhydrinate, the complexes are preferably in a weight ratio of therapeutic agent to polymer of 1:0.8 to 1:1.5.
Preferably the weight ratio is 1:1.
The ~ of complexes of tberapeutic agents (including salts thereof~
with polymers may suitably be ca~ied out by dissolving the polymer and the therapeutic agent (including salts thereof) in suitable solvents, such as iso-propanol.
ethanol or diethyl ether, optionally at elevated ~ ulllrc such as 40C, then forexample adding a 1, ~ g solvent such as n-hexane om,v~l~o.~.~;l.& the solvent0 and triturating the residue with a suitable solvent such as acetone. The resulting ;~d complex is suitably filtered and dried.
Al~.ll~liivcly, such complexes may be prepared by suspending and mixing the therapeutic agent (including salts thereof) and the polymer in water at ambient or elevated . such as 25 to 60C, preferably 50C to 60C, for 5 to 24 hrs.
25 The resulting complex is suitably filtered and dried.
Complexes of tberapeutic agents (including salts thereof) and polymers may be formulated into c~ , ' chewable dosage forms such as chewable tablets.
candies, chewing gums, or soft chewable gelatin capsules using techniques generally known in the art or methods described or analogious to those described in the 30 exat~ples.
Preferably ' ' ~,' /poly.l.~. complexes may be in the form of chewing gums or chewable tablets and ~UAC~ Oly~ complexes may be in the form of chewable tablets or chewing gums.
The following examples are illustrative of the present invention.
Example 1 The Complex of D ' ~.' and Copolymer of Ir.~ l.,.ylic acid and methyl ~ dl.l~ ' ' (CDC), was obtained by stepwise dissolving 10 g of Copolymer (Eudragit L) and 10 g of d;lll~.l}l,~' ' in 100 ml of ;so~,lul ~1, which was heated
- 2-2 ~ 7772 1 ~VO 95/15155 PCT/EP94103903 to 40C until dissolved then 200 ml of ~-hexane were added to precipitate the resulting product which was then filtered and dried.
The 16.8 g of CDC gave the following analytical results.
S Appearance : white powder Numbing taste : absent D ` ydli~ (HPLC assay) : 45.78 mg/100 mg of CDC.
Example 2 The Complex of D ' yd~ and Copolymer of methacrylic acid and methyl .l.~ ' (CDC), was obtained by adding 1.5 kg of D ' ydlil.~t., and 1.5 kg of Copolymer (Eudragit L) to 22.5 Iitres of water, stirring at room t~ Lu(about 20C) for 5 hours, heating to 50C, stirring at 50C for 4 hours, cooling to room l~ l,r~ r, stirring for 2 hours at room t~ p~ ulr" filtering and drying.
The 2.81 kg of CDC, gave the following analytical results:
Appearance : whitepowder Numbingtaste : absent D; ' yl' (~PLC assay) : 46.27 mg/100 mg of CDC
~5 Moi.hlre(K.F.) : ~.5491o WO95/15155 2 1 77721 Pcr/EP941039~3 ~
Chewable Tablets Ex.~4rnples 3 - 5 S The following were granulated and admixed in a ~,o~ iulldl manner and formed into tablets of lSû mg (Example 3), 300 mg each (Example 4) and 600 mg each (Example 5).
Example No.
3 4 5 Complex of Di~ ydlill~L~ and Copolymer of 50 100 200 .,lyliC acid and methyl I.~ lyld~ (CDC)(g) st~rch (g) 12.5 25 50 Lactose (g) 15 30 60 Saccharin sodium (g) 5 10 20 Mint dry flavour (g) 5 10 20 Sorbitol (g) 58.5 117 234 Ammonium gly-,~ ' (g) 1.5 3 6 M. c,.~ ~: ,-- stearate(g) 2.5 5 10 Candies Example 6 Complex of Dimenhydrinate and Copolymer of ~ yli~, acid 100 andmethyl ~- (CDC) (g) Sucrûse (g) 1944 Liquid glucose (g) 1944 Mint navour (g) 12 ~wo 9S/lSlSS 2 1 7 7 7 2 1 PCT/EP9.1/03903 The formula~ion of example No. 6 was prepared by heating the sucrose and the liquid glucose dissolved in purified water, then drying the mass obt~ined and dispersing in the mass the CDC and the mint flavour. The final dispe}sion was 5 pres5ed into candies of 4 g each.
Chewing Gums Examples 7 & 8 Example No.
Complex of D;.. ,.,.~ d~ t., and Copolymer of 50 100 methacrylic acid and methyl methacrylate (CDC) (g) Gum base (g) 495 4g5 Sorbitol (g) 637.5 587.5 Mint oil (g) 10.7 10.7 Menthol (g) 16.5 16.5 Aspartame (g) 7.6 7.6 r~,, stearaoe (g) 12.7 22.7 Milled gum base is mixed with sorbitol (ca 40% of total amount), menthol (ca 90% of total amount) and aspartame (ca 25% of total amount). The blend is wettedwith purified water, kneeded, granulated and then dried at about 40C. The driedgranules are mixed with CDC, mint oil, ~" stearate and the remaining 15 amounts of sorbitol, menthol and aspartame. This final mixture is pressed into chewing gums of 1230 mg each. The chewing gums can be film coated by .,~,..~. I film coating procedures.

WO 95115155 2 1 7 7 7 ~ 1 PCTIEP9 U03903 Soft Chewable Gelabn Capsule Example ~
Complex of D;.lle..l.yl' and Copolymer of ~ a~lylic acid 100 and methyl ' yl, .~ (CDC) (g) Gelatin (g) ` 900 Glycerol (g) 345 Saccharin sodium (g) 5 Orange flavour (g) 50 Purified water (g) 450 The r, of the Example 11 is prepared by dissolving the gelatin and glycerol in the purified water heated to 70C and then, after cooling to 50C, adding thesaccharin sodium, the orange flavour and the CDC. The mass obtained is continually stirred, and processed with a c~ ".Londl rotary-die process, to obtain soft chewable 10 gelatin capsules of 1850 mg each.
The soft gelatin capsules are then dried at 20C and 20% relative humidity for five days.
Example 10 The Complex of paroxetine and Copolymer of Ill~,L~àwylic acid and methyl Ill~.~a~lylat~ (CPC), was obtained by mixing a solution of 3g of Copolymer (Eudragit L) in 150 ml of ethanol with a solution of 3 g of paroxetine base in 100ml of diethyl ether and stirring at room ~ . r for 12 hours. The solvent was then evaporated under vacuum and the residue was triturated with acetone. The precipitate was 20 collected by suction filtration, washed with acetone and dried.
The 4.6 g of CPC gave the following analytical results.
Appearance : white powder Bitter taste : absent Melting point : 215-230C
Paroxetine (HPLC assay) : 42.50mg/lOOmg of CPC
Loss on drying : 0.4%

~wo ss/lslsS 2 1 7 7 7 2 1 r~ A~903 Example 11 The Complex of paroxetine and Copolymer of methacrylic acid and methyl ldt~ (CPC), was obtained by adding lOg of paroxetine hydrochloride , 5 I~ dl~, lOg of Copolimer (Eudragit L) and 2.3g of sodium hydrogen carbonate to 300 ml of water, The mixture was stirred at room t~.a~ Lu-~ for 12 hours, heated to 60C and stirred at 60C for 12 hours. After cooling to room t~ , the precipitate was collected by suction filtration, washed with water and dried.
The 18 g of CPC gave the following analytical results.
Appearance : off-white powder Bitter taste : absent Melting point : 195-235C
Paroxetine (HPLC assay) : 43.53mg/lOOmg of CPC
Moisture (K.F) : 6.3%
Chewable tablets Examples 12,13 & 14 E~:ample No.

Complex of paroxetine and Copolymer of methacrylic acid and methyl 1.l~ laL~
(CPC) (g) 23 46 69 r,~ starch (g) 5 10 15 Aspartame (g) 10 10 10 Strawberry dry flavour (g) 50 50 50 Sorbitol (g) 409 381 353 r~ ~ stearate (g) 3 3 3 CDC aad pl~ starch are mixed, wetted with purified water, kneeded, granulated and then dried at about 40C. The dried granules are mixed with sorbitol, lactose, saccharin sodium"~m. r onillm gly. ~ , mint dried aroma and ~ stearate, then the final mixture is pressed into tablets of 150 mg, 300 mg or 600 mg.

wo gsllSlss 2 1 7 7 7 2 1 PCTII~P9 1/03903 ~
Bi~y ;~ ' Studies In a cross-over single dose study on 12 healthy volunteers, chewable tablets 50 mg ( ~ e to 100 mg of complexed dil~ ydlillG~ were ~Pr~nctr~tpd to be bio-equivalent to swallow soft gelatin capsules (50 mg) of non-complexed product.

Claims (7)

Claims
1. A chewable taste masked formulation comprising a therapeutic agent (or drug) containing at least one basic group or atom optionally in the form of a salt which is reacted with a polymer containing at least one acidic group to form a complex.
2. A chewable taste masked formulation according to claim 1 in which the therapeutic agent is dimenhydrinate or paroxetine.
3. A chewable taste masked formulation according to claim 1 in which the therapeutic agent is in the form of the hydrochloride hemi-hydrate of paroxetine.
4. A chewable taste masked formulation according to claim 1 to 3 in which the polymer is Eudragit.
5. A chewable taste masked formulation accoding to claim 1 to 4 in which the weight ratio of therapeutic agent to drug is 1:0.8 to 1:1.5.
6. A chewable taste masked formulation according to claim 1 to 5 in which the complex of therapeutic agent and polymer is formulated into chewable tablets, candies, chewing gums, or soft chewable gelatin capsules.
7. A chewable taste masked formulation according to claim 6 in which the polymer complex is in the form of chewing gums or chewable tablets.
CA002177721A 1993-12-03 1994-11-24 Taste masked composition containing a drug/polymer complex Abandoned CA2177721A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI93A002540 1993-12-03
ITMI932540A IT1274241B (en) 1993-12-03 1993-12-03 THERAPEUTIC AGENT / POLYMER MATRIX COMPLEXES EQUIPPED WITH IMPROVED FLAVOR CHARACTERISTICS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Publications (1)

Publication Number Publication Date
CA2177721A1 true CA2177721A1 (en) 1995-06-08

Family

ID=11367288

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002177721A Abandoned CA2177721A1 (en) 1993-12-03 1994-11-24 Taste masked composition containing a drug/polymer complex

Country Status (9)

Country Link
EP (1) EP0804168A1 (en)
JP (1) JPH09505818A (en)
CN (1) CN1145586A (en)
AU (1) AU693144B2 (en)
CA (1) CA2177721A1 (en)
IT (1) IT1274241B (en)
NZ (1) NZ277238A (en)
WO (1) WO1995015155A1 (en)
ZA (1) ZA949567B (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6548084B2 (en) * 1995-07-20 2003-04-15 Smithkline Beecham Plc Controlled release compositions
AU748804B2 (en) * 1995-07-20 2002-06-13 Smithkline Beecham Plc Paroxetine controlled release compositions
GB9514842D0 (en) * 1995-07-20 1995-09-20 Smithkline Beecham Plc Novel formulation
CA2206592A1 (en) * 1996-05-30 1997-11-30 Shu-Zhong Wang Method of producing amorphous paroxetine hydrochloride
US5965555A (en) * 1996-06-07 1999-10-12 Hoechst Aktiengesellschaft Xanthine compounds having terminally animated alkynol side chains
DE19631084A1 (en) * 1996-08-01 1998-02-05 Basf Ag Use of (meth) acrylic acid copolymers to increase the permeability of the mucosa
US6638948B1 (en) 1996-09-09 2003-10-28 Pentech Pharmaceuticals, Inc. Amorphous paroxetine composition
EE03970B1 (en) 1997-06-10 2003-02-17 Synthon B.V. 4-Phenylpiperidine Compound, its preparation and use, and medicament containing it
US5955475A (en) * 1997-06-30 1999-09-21 Endo Pharmaceuticals Inc. Process for manufacturing paroxetine solid dispersions
NZ505123A (en) * 1997-12-19 2003-07-25 Smithkline Beecham Corp Process for manufacturing bite-dispersion tablets by compressing medicaments and other ingredients into granulates then compressing the granulates and other ingredients into tablets, and the tablets thereof
IT1298732B1 (en) * 1998-03-13 2000-02-02 Recordati Chem Pharm ORAL PHARMACEUTICAL COMPOSITIONS ASSUMABLE WITHOUT LIQUIDS, CONTAINING INCLUSION COMPLEXES
CH689805A8 (en) * 1998-07-02 2000-02-29 Smithkline Beecham Plc Paroxetine methanesulfonate, process for its preparation and pharmaceutical compositions containing it.
AU3810100A (en) 1999-03-12 2000-10-04 Basf Aktiengesellschaft Stable pharmaceutical application form for paroxetin anhydrate
GB0119467D0 (en) * 2001-08-09 2001-10-03 Smithkline Beecham Plc Novel compound
ES2261726T3 (en) * 2001-08-09 2006-11-16 Smithkline Beecham Plc COMPOSITION THAT INCLUDES PAROXETINE AND A PHARMACEUTICALLY ACCEPTABLE GLICIRRICINATE SALT.
PT2802311T (en) * 2011-10-25 2019-03-19 Expermed S A Sublingual pharmaceutical composition containing an antihistamine agent and method for the preparation thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ217326A (en) * 1985-08-26 1990-02-26 Searle & Co A porous, active drug-polymer matrix having masked taste properties, wherein the active drug contains amine or amido groups

Also Published As

Publication number Publication date
EP0804168A1 (en) 1997-11-05
WO1995015155A1 (en) 1995-06-08
JPH09505818A (en) 1997-06-10
NZ277238A (en) 1998-04-27
ITMI932540A0 (en) 1993-12-03
AU1219895A (en) 1995-06-19
CN1145586A (en) 1997-03-19
AU693144B2 (en) 1998-06-25
IT1274241B (en) 1997-07-15
ITMI932540A1 (en) 1995-06-03
ZA949567B (en) 1995-10-10

Similar Documents

Publication Publication Date Title
CA2177721A1 (en) Taste masked composition containing a drug/polymer complex
CA1320192C (en) Pharmaceutical compositions
CA2377916C (en) Taste masked pharmaceutical liquid formulations
US6649187B2 (en) Use of polyalkylamine polymers in controlled release devices
US8758779B2 (en) Pharmaceutical composition of duloxetine
US20080095842A1 (en) Rapidly Disintegrating Taste Masked Compositions and a Process for Its Preparations
CA1146545A (en) Pharmaceutical composition comprising bencyclane fumarate and cyclodextrin
DE69419281T2 (en) Flavor-masked solid preparation and manufacturing method
CA2163111C (en) Process for the preparation of an oral solid dosage form containing diclofenac
CA2618187C (en) Novel resinate complex of s-clopidogrel and production method thereof
CZ20014379A3 (en) Composition for masking taste and process for preparing thereof
US5968906A (en) Sucralfate preparations
AU739295B2 (en) Eprosartan arginyl charge-neutralization-complex and a process for its production and formulation
KR100675081B1 (en) Acetylcysteine oral dosage forms
CN1222316C (en) Oral liquor composition with reduced bitter taste
US5834492A (en) Water soluble orally effective iron chelator
WO1996002531A1 (en) Water soluble orally effective iron chelator
HU204997B (en) Process for producing carrier system suitable for ensuring controlled biological access to dihydropyridines, as well as new oral dosage form ensuring improved biological access
AU732785B2 (en) Process for the preparation of an oral solid dosage form containing diclofenac
GB1596166A (en) Pharmaceutical compositions
EP0535269A1 (en) Pharmaceutical compositions containing thiazolidinedione derivatives
IE990009A1 (en) Taste-masked composition
SK278519B6 (en) Water soluble inclusive complex of silybinine together with cyclodextrine, preparation method thereof and pharmaceutical composition contaning that complex

Legal Events

Date Code Title Description
FZDE Discontinued