NZ277238A - Taste masked composition containing paroxetine complexed with a polymer - Google Patents

Taste masked composition containing paroxetine complexed with a polymer

Info

Publication number
NZ277238A
NZ277238A NZ277238A NZ27723894A NZ277238A NZ 277238 A NZ277238 A NZ 277238A NZ 277238 A NZ277238 A NZ 277238A NZ 27723894 A NZ27723894 A NZ 27723894A NZ 277238 A NZ277238 A NZ 277238A
Authority
NZ
New Zealand
Prior art keywords
polymer
chewable
taste masked
therapeutic agent
paroxetine
Prior art date
Application number
NZ277238A
Inventor
Franco Francese
Massimo Maneschi
Diego Oldani
Tiziana Crolla
Original Assignee
Smithkline Beecham Spa Formerl
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 Smithkline Beecham Spa Formerl filed Critical Smithkline Beecham Spa Formerl
Publication of NZ277238A publication Critical patent/NZ277238A/en

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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

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  • 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)

Description

New Zealand Paient Spedficaiion for Paient Number £77238 vf"s New Zealand No. 277238 Int?-, national No. PCT/EPc/4/03903 TO BE ENTERED AFTER ACCEPTANCE AND PUBLICATION Priority dates: 03.12.1993; Complete Specification Filed: 24.11.1994 Classification:^) A61K31/20; A61K9/48.68; A61K47/48 Publication date: 27 April 1998 Journal No.: 1427 NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION Title of Invention: Taste masked composition containing a drug/polymer complex Name, address and nationality of applicant(s) as in international application form: SMITHKLINE BEECHAM SpA, an Italian company of Via Zambeletti, 1-20021 Baranzate, Milan, Italy WO 95/15155 PCT/EJS4/03903 TASTE MASKED COMPOSITION CONTAINING A DRUG/POLYMER COMPLY' ' J 8 2> The present invention relates to therapeutic agent/polymer matrix complexes which have improved taste characteristics.
Many therapeutically active substances have an unpleasant taste or cause a numbing effect when administered by mouth to a patient.
Many therapeutic agent/polymer combinations are known but the therapeutic agent is coated with the polymer. The problem with such products is that they are liable to be broken when orally administered by the patient, particularly when 10 chewed, thereby allowing the therapeutic agent to be in direct contact with the mouth, thus the taste and/or numbing sensation of the therapeutic agent is no longer effectively masked.
A further problem with copolymers of methacrylic acid and methyl methacrylate is that when complexed with therapeutic agents the product formed 15 tends to be a gum.
One particular drug, dimenhydrinate, is useful for treating the symptoms associated with travel sickness. Dimenhydrinate has a numbing taste.
A preferred formulation of dimenhydrinate is in the form of a chewing gum or a chewable tablet which means that the conventional coating techniques using 20 polymers such as anionic copolymers based on methacrylic acid and methylmethacrylate (such as Eudragit), are ineffective in masking the numbing taste because the conventional polymer coated dimenhydrinate complex is broken down when chewed by the patient Another drug, paroxetine, is useful for the treatment of depression, panic 25 disorders and obssessive compulsive disorders. Paroxetine has an unpleasant bitter taste.
The present invention provides a therapeutic agent/polymer complex with superior taste masking qualities and can be prepared as a powder which is more easily formulated with other excipients to form conventional formulations.
Accordingly, the present invention provides 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.
The preferred therapeutic agent is dimenhydrinate or paroxetine, more particularly paroxetine. 35 The term "basic group or atom" is understood to mean a group capable of donating electrons. Such groups include optionally substituted amino groups or optionally substituted thio groups.
Suitable salts of therapeutic agents include acid addition salts which are suitably pharmaceutical^ acceptable salts such as the hydrochloride hemi-hydrate for , RECEIVED Intalkotual Property Office ' 6 FEB 1998 WO 95/15155 PCT£gP94/03903 paroxetine. ^ It should be appreciated that in cases where the drug comprises two active ^ ^ components i.e. a basic one and an acidic one in the form of a salt, such as dimenhydrinate, which is the 8-chlorotheophylline salt of diphenhydramine then the 5 term therapeutic agent in the form of a salt extends to both of these components.
Preferred polymers include polymethacrylates such as Eudragit L and S which are copolymers of methacrylic acid and methyl methacrylate 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 preparation of complexes of therapeutic agents (including salts thereof) with polymers may suitably be carried 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 temperatures such as 40°C, then for example adding a precipitating solvent such as n-hexane or evaporating the solvent 20 and triturating the residue with a suitable solvent such as acetone. The resulting precipitated complex is suitably filtered and dried.
Alternatively, such complexes may be prepared by suspending and mixing the therapeutic agent (including salts thereof) and the polymer in water at ambient or elevated temperatures such as 25 to 60°C, preferably 50°C to 60°C, for 5 to 24 hrs. 25 The resulting complex is suitably filtered and dried.
Complexes of therapeutic agents (including salts thereof) and polymers may be formulated into conventional 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 examples.
Preferably dimenhydrinate/polymer complexes may be in the form of chewing gums or chewable tablets and paroxetine/polymer 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 Dimenhydrinate and Copolymer of methacrylic acid and methyl methacrylate (CDC), was obtained by stepwise dissolving 10 g of Copolymer (Eudragit L) and 10 g of dimenhydrinate in 100 ml of isopropanol, which was heated - 2 - .RECEIVED intellectual Property Office ' 6 FEB 1998 AI II.. ■— WO 95/15155 PCT/EP94/03903 to 40°C until dissolved then 200 ml of n-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.
Appearance white powder Numbing taste Dimenhydrinate (HPLC assay) absent 45.78 mg/100 mg of CDC.
Example 2 The Complex of Dimenhydrinate and Copolymer of methacrylic acid and methyl methacrylate (CDC), was obtained by adding 1.5 kg of Dimenhydrinate and 1.5 kg of Copolymer (Eudragit L) to 22.5 litres of water, stirring at room temperature (about 20°C) for 5 hours, heating to 50°C, stirring at 50°C for 4 hours, cooling to room temperature, stirring for 2 hours at room temperature, filtering and drying.
The 2.81 kg of CDC, gave the following analytical results: $ Appearance Numbing taste Dimenhydrinate (HPLC assay) white powder absent 46.27 mg/100 mgofCDC Moisture (K.F.) 0.54% Chewable Tablets Examples 3 - 5 The following were granulated and admixed in a conventional manner and formed into tablets of 150 mg (Example 3), 300 mg each (Example 4) and 600 mg each (Example 5).
Example No. 3 4 5 Complex of Dimenhydrinate and Copolymer of methacrylic acid and methyl methacrylate (CDC)(g) 50 100 200 Pregelatinized starch (g) 12.5 25 50 Lactose (g) Saccharin sodium (g) 30 60 5 10 20 Mint dry flavour (g) Sorbitol (g) 20 58.5 117 234 Ammonium glycyrrhizinate (g) Magnesium stearate (g) 1.5 3 6 2.5 5 10 Candies Example 6 Complex of Dimenhydrinate and Copolymer of methacrylic acid 100 and methyl methacrylate (CDC) (g) Sucrose (g) Liquid glucose (g) 1944 1944 Mint flavour (g) 12 WO 95/15155 PCT/EP94/03903 The formulation of example No. 6 was prepared by heating the sucrose and the liquid glucose dissolved in purified water, then drying the mass obtained and dispersing in the mass the CDC and the mint flavour. The final dispersion was 5 pressed into candies of 4 g each.
Chewing Gums Examples 7 & 8 Example No. 7 8 ' Complex of Dimenhydrinate and Copolymer of 50 100 methacrylic acid and methyl methacrylate (CDC) (g) Gum base (g) 495 495 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 Magnesium stearate (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 wetted with purified water, kneeded, granulated and then dried at about 40°C. The dried granules are mixed with CDC, mint oil, magnesium 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 conventional film coating procedures.
|WO 95/15155 PCT/EP94/03903 Soft Chewable Gelatin Capsule Example 9 Complex of Dimenhydrinate and Copolymer of methacrylic acid 100 and methyl methacrylate (CDC) (g) Gelatin (g) 900 Glycerol (g) 345 Saccharin sodium (g) 5 Orange flavour (g) 50 Purified water (g) 450 The formulation of the Example 11 is prepared by dissolving the gelatin and glycerol in the purified water heated to 70°C and then, after cooling to 50°C, adding the saccharin sodium, the orange flavour and the CDC. The mass obtained is continually stirred, and processed with a conventional rotary-die process, to obtain soft chewable 10 gelatin capsules of 1850 mg each.
The soft gelatin capsules are then dried at 20°C and 20% relative humidity for five days.
Example 10 The Complex of paroxetine and Copolymer of methacrylic acid and methyl metacrylate (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 temperature 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 Bitter taste Melting point Paroxetine (HPLC assay) Loss on drying : white powder : absent : 215-230°C : 42.50mg/100mg of CPC : 0.4% IWO 95/15155 Example 11 The Complex of paroxetine and Copolymer of methacrylic acid and methyl methacrylate (CPC), was obtained by adding lOg of paroxetine hydrochloride hemihydrate, lOg of Copolimer (Eudragit L) and 2.3g of sodium hydrogen carbonate to 300 ml of water. The mixture was stirred at room temperature for 12 hours, heated to 60°C and stirred at 60°C for 12 hours. After cooling to room temperature, 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 : 195-235°C Paroxetine (HPLC assay) : 43.53mg/100mg of CPC Moisture (K.F) : 6.3% Chewable tablets Examples 12,13 & 14 Example No.
Complex of paroxetine and Copolymer of methacrylic acid and methyl methacrylate (CPC) (g) Pregelatinized starch (g) Aspartame (g) Strawberry dry flavour (g) Sorbitol (g) Magnesium stearate (g) 12 13 14 23 46 69 50 50 50 409 381 353 3 3 3 CDC and pregelatinized starch are mixed, wetted with purified water, kneeded, granulated and then dried at about 40°C. The dried granules are mixed with sorbitol, lactose, saccharin sodium, ammonium glycyrrhizinate, mint dried aroma and 20 magnesium stearate, then the final mixture is pressed into tablets of 150 mg, 300 mg or 600 mg.
Bioequivalence Studies In a cross-over single dose study on 12 healthy volunteers, chewable tablets 50 mg (corresponding to 100 mg of complexed dimenhydrinate were demonstrated to be bio-equivalent to swallow soft gelatin capsules (50 mg) of non-complexed dimenhydrinate product.

Claims (5)

WHAT WE CLAIM IS:
1. A chewable taste masked formulation comprising a therapeutic agent, which is paroxetine optionally in the form of a salt, which is reacted with a polymer, which is a copolymer of methacrylic acid and methyl methacrylate, to form a complex.
2. 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.
3. A chewable taste masked formulation according to claim 1 or claim 2 in which the weight ratio of therapeutic agent to polymer is 1:0.8 to 1:1.5.
4. A chewable taste masked formulation according to any one of claims 1 to 3 in which the complex of therapeutic agent and polymer is formulated into chewable tablets, candies, chewing gums, or soft chewable gelatin capsules.
5. A chewable taste masked formulation according to claim 4 in which the polymer complex is in the form of chewing gums or chewable tablets. S END OF CLAIMS RECEIVED mtelleatuet Propdrty Office I 6 FEB 1998 _ 9 - of Nnw Zwtond
NZ277238A 1993-12-03 1994-11-24 Taste masked composition containing paroxetine complexed with a polymer NZ277238A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI932540A IT1274241B (en) 1993-12-03 1993-12-03 THERAPEUTIC AGENT / POLYMER MATRIX COMPLEXES EQUIPPED WITH IMPROVED FLAVOR CHARACTERISTICS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
PCT/EP1994/003903 WO1995015155A1 (en) 1993-12-03 1994-11-24 Taste masked composition containing a drug/polymer complex

Publications (1)

Publication Number Publication Date
NZ277238A true NZ277238A (en) 1998-04-27

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ID=11367288

Family Applications (1)

Application Number Title Priority Date Filing Date
NZ277238A NZ277238A (en) 1993-12-03 1994-11-24 Taste masked composition containing paroxetine complexed with a polymer

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
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
US6548084B2 (en) 1995-07-20 2003-04-15 Smithkline Beecham Plc Controlled release compositions
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
ES2155995T3 (en) 1997-06-10 2001-06-01 Synthon Bv 4-PHENYLPIPERIDINE COMPOUNDS.
US5955475A (en) * 1997-06-30 1999-09-21 Endo Pharmaceuticals Inc. Process for manufacturing paroxetine solid dispersions
EP1047407A4 (en) * 1997-12-19 2007-05-02 Smithkline Beecham Corp Process for manufacturing bite-dispersion tablets
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.
ATE311883T1 (en) 1999-03-12 2005-12-15 Aesica Pharmaceuticals Ltd STABLE PHARMACEUTICAL USE FORM FOR PAROXETINE ANHYDRATE
GB0119467D0 (en) * 2001-08-09 2001-10-03 Smithkline Beecham Plc Novel compound
EP1414408B1 (en) * 2001-08-09 2006-03-29 Smithkline Beecham Plc Composition comprising paroxetine and a pharmaceutically acceptable glycyrrhizinate salt
AU2011379627B2 (en) * 2011-10-25 2015-09-10 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
DE3678640D1 (en) * 1985-08-26 1991-05-16 Procter & Gamble TASTE-COVERING COMPOSITIONS.

Also Published As

Publication number Publication date
ITMI932540A0 (en) 1993-12-03
AU693144B2 (en) 1998-06-25
ZA949567B (en) 1995-10-10
CN1145586A (en) 1997-03-19
WO1995015155A1 (en) 1995-06-08
IT1274241B (en) 1997-07-15
JPH09505818A (en) 1997-06-10
EP0804168A1 (en) 1997-11-05
CA2177721A1 (en) 1995-06-08
ITMI932540A1 (en) 1995-06-03
AU1219895A (en) 1995-06-19

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