AU693144B2 - Taste masked composition containing a drug/polymer complex - Google Patents
Taste masked composition containing a drug/polymer complex Download PDFInfo
- Publication number
- AU693144B2 AU693144B2 AU12198/95A AU1219895A AU693144B2 AU 693144 B2 AU693144 B2 AU 693144B2 AU 12198/95 A AU12198/95 A AU 12198/95A AU 1219895 A AU1219895 A AU 1219895A AU 693144 B2 AU693144 B2 AU 693144B2
- Authority
- AU
- Australia
- Prior art keywords
- document
- chewable
- taste masked
- date
- copolymer
- 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.)
- Ceased
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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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Description
IL,- WO 95/15155 PCT/EP94/03903 TASTE MASKED COMPOSITION CONTAINING A DRUG/POLYMER
COMPLEX
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 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 tends to be a gum.
One particular drug, dimenhydrinate, is useful for treating the symptoms :oo associated with travel sickness. Dimenhydrinate has a numbing taste.
"o A preferred formulation of dimenhydrinate is in the form of a chewing gum or S a chewable tablet which means that the conventional coating techniques using polymers such as anionic copolymers based on methacrylic acid and S' 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 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 exc;pients to form conventional formulations.
Accordingly, the present invention provides a chewable taste masked formulation comprising paroxetine optionally in the form of a salt, which is reacted with a copolymer of methacrylic acid and methyl methacrylate to form a complex.
Suitable salts of paroxetine include acid addition salts which are suitably pharmaceutically acceptable salts such as the hydrochloride bemi-hydrate for paroxetine.
-1i -n I WO 95/15155 PCTiEP94/03903 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 term therapeutic agent in the form of a salt extends to both of these components.
Suitable copolymers 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 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 0 C, then for .o example adding a precipitating solvent such as n-hexane or evaporating the solvent So. 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 5 3C 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 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.
SRAL Example 1 SThe Complex of Dimenhydrinate and Copolymer of methacrylic acid and methyl methacrylate (CDC), was obtained by stepwise dissolving 10 g of Copolymer Tr o (Eudragit L) and 10 g of dimenhydrinate in 100 ml of isopropanol, which was heated
I
WO 95/15155 PCT/EP94/03903 to 40 0 C until dissolved then 200 ml ofn-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 Numbing taste Dimenhydrinate (HPLC assay) white powder 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 kg of Copolymer (Eudragit L) to 22.5 litres of water, stirring at room temperature (about 20 0 C) for 5 hours, heating to 50 0 C, stirring at 50 0 C for 4 hours, cooling to room temperaturc, stirring for 2 hours at room temperature, filtering and drying.
The 2.81 kg of CDC, gave the following analytical results: Appearance Numbing taste white powder absent Dimenhydrinate (HPLC assay) Moisture 46.27 mg/100 mg of CDC 0.54% I
A
r i WO 95/15155 PCT/EP94/03903
I
Chewable Tablets Examples 3 5 The following were granulated and admixed in a conventional manner and formed into tablets of 150 mg (Example 300 mg each (Example 4) and 600 mg each (Example Example No.
3 4 Complex of Dimenhydrinate and Copolymer of 50 100 200 methacrylic acid and methyl methacrylate (CDC)(g) Pregelatinized starch 12.5 25 Lactose 15 30 Saccharin sodium 5 10 Mint dry flavour 5 10 Sorbitol 58.5 117 234 Ammonium glycyrrhizinate 1.5 3 6 Magnesium stearate 2.5 5 Candies Example 6 Complex of Dimenhydrinate and Copolyner of methacrylic acid 100 and methyl methacrylate (CDC) (g) Sucrose 1944 Liquid glucose 1944 Mint flavour 12 -4- 11- 41; 1111 IF 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 pressed into candies of 4 g each.
Chewing Gums Examples 7 8 Example No.
Complex of Dimenhydrinate and Copolymer of methacrylic acid and methyl methacrylate (CDC) (g) Gum base (g) 50 100 Sorbitol (g) Mint oil (g) 637.5 587.5 Menthol (g) Aspartame (g) Magnesium stearate (g) 10.7 16.5 7.6 12.7 10.7 16.5 7.6 22.7 Milled gum base is mixed with sorbitol (ca 40% of total amount), menthol (ca 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 0 C. The dried granules are mixed with CDC, mint oil, magnesium stearate and the remaining 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.
F A 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 900 Glycerol 345 Saccharin sodium Orange flavour Purified water 450 The formulation of the Example 11 is prepared by dissolving the gelatin and glycerol in the purified water heated to 70 0 C and then, after cooling to 50 0 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 gelatin capsules of 1850 mg each.
The soft gelatin capsules are then dried at 20°C and 20% relative humidity for five days.
Example 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 Sunder vacuum and the residue was triturated with acetone. The precipitate was 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 :215-230°C Paroxetine (HPLC assay) 42.50mg/100mg of CPC Loss on drying :0.4% -6- L I_ -I 1 i WO 95/15155 PCT/EP94/03903 Example 11 The Complex of paroxetine and Copolymer of methacrylic acid and methyl methacrylate (CPC), was obtained by adding 10g of paroxetine hydrochloride hemihydrate, 10g 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 0 C and stirred at 60 0 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 :6.3% Chewable tablets Examples 12, 13 14 Example No.
12 13 14 Complex of paroxetine and Copolymer of methacrylic acid and methyl methacrylate (CPC) 23 46 69 Pregelatinized starch 5 10 Aspartame 10 10 Strawberry dry flavour 50 50 Sorbitol 409 381 353 Magnesium stearate 3 3 3 CDC and pregelatinized starch are mixed, wetted with purified water, kneeded, granulated and then dried at about 40 0 C. The dried granules are mixed with sorbitol, lactose, saccharin sodium, ammonium glycyrrhizinate, mint dried aroma and magnesium stearate, then the final mixture is pressed into tablets of 150 mg, 300 mg or 600 mg.
-7- WO 95/15155 PCTEP94/03903 Bioequivalence Studies In a cross-over single dose study on 12 healthy volunteers, chewable tablets 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.
Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" and "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps.
a o a o o00 A0 0 0 e 0 o, 00 ~f -8-
Claims (8)
1. A chewable taste masked formulation comprising paroxetine optionally in the form of a salt, which is reacted with 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 paroxetine is in the form of the hydrochloride hemi-hydrate.
3. A chewable taste masked formulation according to claim 1 or 2 in which the copolymer is Eudragit.
4. A chewable taste masked formulation according to claim 1 or 2 in which the polymer is Eudragit L.
5. A chewable taste masked formulation according to claim 1 to 4 in which the weight ratio of paroxetine to copolymer is 1:0.8 to 1:1.5.
6. A chewable taste masked formulation according to any one of claims 1 to 5 in which 20 the complex of paroxetine and copolymer 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 copolymer complex is in the form of chewing gums or chewable tablets. I o s, I 0 t o a 00 o a 0 00 0 00 a «oo o a* O 60 6 oB B B I I-" -i j ^l *J i 1 P:\OPER\PDB\ISPA.092 3/4/98
8. A chewable taste masked formulation according to claim 1 substantially as hereinbefore described with reference to the Examples. DATED this SECOND day of APRIL 1998 SmithKline Beecham p.l.c. by DAVIES C OLLISON CAVE Patent Attorneys for the applicant(s) *0 t ':r 4 INTERNATIONAL SEARCH REPORT International apolication No. PCT/EP 94/03903 A. CLASSIFICATION OF SUBJECT MATTER IPC 6 A61K9/16 A61K9/00 According to International Patent Classification (IPC) or to both national classification and IPC B. FIELDS SEARCHED Milmmum documentation searched (classtfication system followed by classfication symbols) IPC 6 A61K Documentation searched other than minimum documentation to the exts:nt that such documents are included in the fields searched Electronic data base consulted dunng the international search (name of data base and, where practical, search terms used) C. DOCUMENTS CONSIDERED TO BE RELEVANT Category' Citaton of document, with imdcation, where appropnate, of the relevant passages Relevant to claim No. X EP,A,O 212 641 D. SEARLE CO.) 4 1-7 March 1987 see claims 1-3,8,9 see example 6 SFurther documents are listed in the continuation of box C. Patent family members are listed in annex. SSpecial categories of cted documents: 'T later document published after the mternational filing date or priority date and not in conflict with the application but A document defning the general state of the art which is not cted to understand the pnncple or theory underlying the considered to be of particular relevance invenUon earlier document but published on or after the international document of particular relevance; the claimed invention filing date cannot be considered novel or cannot be considered to document which may throw doubts on priority claim(s) or involve an inventive step when the document is taken alone which is cited to establish the publication date of another document of particular relevance; the claimed invenon citation or other special reason (as specified) cannot be considered to involve an inventive step when the document refernng to an oral disclosure, use, exhibition or document is combined with one or more other such docu- other means ments, such combination being obvious to a person skilled document published pnor to the international filing date but in the art. later than the priority date claimed document member of the same patent family Date of the actual completion of the International search Date of mailing of the intemational search report 28 February 1995 1 5. 03. Name and mailing address of the ISA Authorized officer European Patent Office, P.B. 5818 Patentlaan 2 NL 2280 HV Rilswilk Tel. (31-70) 340-2040, Tx. 31 651 epo nl, en Am A Fax: 31-70) 340-3016 Ventura Amat, A 'orm PCT7ISA/;i10 (lecond sheet) (July 1992) Nj~e' I 1 INTERNATIONAL SEARCH REPORT Iinternational application No. Informion on patent family members PCT/EP 94/03903 Patent document Publication Patent family I Publication cited in search report date member(s) date EP-A-0212641 04-03-87 AU-B- 589991 26-10-89 AU-A- 6168086 05-03-87 IE-B- 58832 17-11-93 JP-A- 62051627 06-03-87 NO-C- 174032 09-03-94 US-A- 5286489 15-02-94 US-A- 4971791 20-11-90 Form PCT/ISA/210 (patnt family annex) (July 1993)
Applications Claiming Priority (3)
| 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 |
| ITMI93A2540 | 1993-12-03 | ||
| PCT/EP1994/003903 WO1995015155A1 (en) | 1993-12-03 | 1994-11-24 | Taste masked composition containing a drug/polymer complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1219895A AU1219895A (en) | 1995-06-19 |
| AU693144B2 true AU693144B2 (en) | 1998-06-25 |
Family
ID=11367288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU12198/95A Ceased AU693144B2 (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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6548084B2 (en) * | 1995-07-20 | 2003-04-15 | Smithkline Beecham Plc | Controlled release compositions |
| GB9514842D0 (en) * | 1995-07-20 | 1995-09-20 | Smithkline Beecham Plc | Novel formulation |
| AU748804B2 (en) * | 1995-07-20 | 2002-06-13 | Smithkline Beecham Plc | Paroxetine 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 |
| SK283394B6 (en) | 1997-06-10 | 2003-07-01 | Synthon B. V. | 4-phenylpiperidine compounds and its pharmaceutically acceptable salts, process for their preparation, medicament containing them and their use |
| US5955475A (en) * | 1997-06-30 | 1999-09-21 | Endo Pharmaceuticals Inc. | Process for manufacturing paroxetine solid dispersions |
| CA2315088A1 (en) * | 1997-12-19 | 1999-07-01 | Smithkline Beecham Corporation | 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. |
| JP4854115B2 (en) | 1999-03-12 | 2012-01-18 | エイシカ ファーマシューティカルス リミテッド | Stable formulation for anhydrous paroxetine |
| 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 |
| US9675551B2 (en) * | 2011-10-25 | 2017-06-13 | Expermed S.A. | Sublingual pharmaceutical composition containing an antihistamine agent and method for the preparation thereof |
Family Cites Families (1)
| 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 |
-
1993
- 1993-12-03 IT ITMI932540A patent/IT1274241B/en active IP Right Grant
-
1994
- 1994-11-24 JP JP7515376A patent/JPH09505818A/en active Pending
- 1994-11-24 CA CA002177721A patent/CA2177721A1/en not_active Abandoned
- 1994-11-24 WO PCT/EP1994/003903 patent/WO1995015155A1/en not_active Ceased
- 1994-11-24 NZ NZ277238A patent/NZ277238A/en unknown
- 1994-11-24 AU AU12198/95A patent/AU693144B2/en not_active Ceased
- 1994-11-24 CN CN94194885A patent/CN1145586A/en active Pending
- 1994-11-24 EP EP95903281A patent/EP0804168A1/en not_active Withdrawn
- 1994-12-01 ZA ZA949567A patent/ZA949567B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2177721A1 (en) | 1995-06-08 |
| ITMI932540A0 (en) | 1993-12-03 |
| IT1274241B (en) | 1997-07-15 |
| WO1995015155A1 (en) | 1995-06-08 |
| AU1219895A (en) | 1995-06-19 |
| NZ277238A (en) | 1998-04-27 |
| CN1145586A (en) | 1997-03-19 |
| EP0804168A1 (en) | 1997-11-05 |
| ITMI932540A1 (en) | 1995-06-03 |
| JPH09505818A (en) | 1997-06-10 |
| ZA949567B (en) | 1995-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |