GB2248185A - Ranitidine formulations - Google Patents
Ranitidine formulations Download PDFInfo
- Publication number
- GB2248185A GB2248185A GB9119284A GB9119284A GB2248185A GB 2248185 A GB2248185 A GB 2248185A GB 9119284 A GB9119284 A GB 9119284A GB 9119284 A GB9119284 A GB 9119284A GB 2248185 A GB2248185 A GB 2248185A
- Authority
- GB
- United Kingdom
- Prior art keywords
- composition
- methyl
- ranitidine
- bismuth
- salt
- 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.)
- Granted
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/245—Bismuth; Compounds thereof
-
- 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
- A61K9/2009—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Abstract
Pharmaceutical prepn. comprises: (a) a salt of ranitidine (I) with a bismuth complex of tartaric or citric acid; and (b) an alkali salt. Pref., the salt is e.g. -N-(Q)-N'-methyl-2-nitro -1,1-ethenediamine-2-hydroxy -1,2,3-propanetricarboxylate -bismuth (3+).
Description
PHARMACEUTICAL COMPOSITIONS CONTAINING FURAN DERIVATIVES The present
invention relates to improvements in the formulation of derivatives of the H2-receptor antagonist ranitidine, particularly for oral administration. More especially the invention is concerned with pharmaceutical compositions in which the active ingredient is a salt of ranitidine and a complex of bismuth with a carboxylic acid.
Published UK Patent Specification No. 2220937A describes and claims salts formed between ranitidine and a complex of bismuth with a carboxylic acid, particularly tartaric acid and, more especially, citric acid. Such salts possess the 112 antagonist antisecretory properties associated with ranitidine, together with antibacterial activity against HelicobacterMyLori (formerly Campylobacter pvlori). In addition, such salts possess cytoprotective properties, and display activity against the human gastric pepsins, with preferential inhibition of pepsin 1, a pepsin isozyme associated with peptic ulcer.
The salts disclosed in UK Patent Specification No. 2220937A thus possess a particularly advantageous combination of properties for the treatment of gastrointestinal disorders, especially peptic ulcer disease and other gastroduodenal conditions, for example gastritis and non-ulcer dyspepsia.
UK Patent Specification No. 2220937A also discloses pharmaceutical compositions containing salts formed between ranitidine and a complex of bismuth with a carboxylic acid. Such compositions are primarily intended for oral administration, and may take the form of for example tablets, capsules, solutions, syrups, suspensions or dry products for constitution with water or other suitable vehicle before use.
One of the important properties associated with pharmaceutical compositions in solid form for oral administration is that, once swallowed by the patient, they should disintegrate and/or dissolve in order to release the active ingredient. It has now been found that the rate of disintegration and/or dissolution of such HA156 compositions, in particular tablets, containing a salt of the type described in UK Patent Specification No. 2220937A as the active ingredient, may be significantly improved, particularly under acid conditions, by incorporating an alkaline salt into the formulation. This in turn serves to increase the extent to which the active ingredient is released from the composition.
Thus the present invention provides a pharmaceutical composition in solid unit dosage form for oral administration, comprising a salt formed between ranitidine and a complex of bismuth with a carboxylic acid selected from tartaric acid or citric acid, and an alkaline salt.
Compositions containing solvates, including hydrates, of the ranitidine salts are also included within the scope of the invention.
The salt of ranitidine may be for example N-[2-[[[5[(dimethylamino)methyl]- 2 -furanyl]methyl] thio] ethyl] -N'-methyl-2-nitro- 1, 1 -ethenediamine 2- hydroxy-1,2,3 prop an etri c arboxyl ate bismuth (3+) complex, also known as ranitidine bismuth citrate; or N- [2- [ [ [5- [ (dimethyl amin o)meth yll -2-furanyl] methyl] thio] ethyl] -N' methyl -2-nitro- 1, 1-ethenediamine [R-(RR)]-2,3-dihydroxybutanedioate bismuth (3+) complex, also known as ranitidine bismuth tartrate. Such salts may be formed by reacting ranitidine with an appropriate bismuth carboxylic acid complex, e.g.
bismuth citrate or bismuth tartrate.
Compositions containing ranitidine bismuth citrate as the active ingredient are particularly preferred.
The alkaline salt may be for example a carbonate, bicarbonate, citrate, phosphate, acetate, or chloride salt. The use of an alkali metal (e.g. sodium or potassium) or alkaline earth metal (e.g. magnesium or calcium) carbonate or bicarbonate, or mixtures thereof is preferred. Sodium bicarbonate and/or sodium carbonate is particularly preferred, more especially sodium carbonate, which may conveniently be used in its anhydrous form. Examples of other suitable alkaline salts that may be used include ammonium citrate, ammonium carbonate, ammonium phosphate, ammonium chloride, sodium acetate, sodium citrate, sodium phosphate, potassium acetate, potasssium citrate and dipotassium phosphate.
HA156 The amount of ranitidine bismuth carboxylate in the composition according to the invention may be for example 15Orng to 1.5g, preferably 200 to 80Orng.
The alkaline salt may constitute for example 2% to 20% of the composition on a weight-to-weight (w/w) basis, preferably 2% to 8%.
The ranitidine bismuth carboxylate content of the composition may be for example 20% to 95%, preferably 50% to 95%, more particularly 80% to 95%, on a w/w basis.
A preferred composition comprises ranitidine bismuth citrate and sodium carbonate.
The compositions according to the invention are intended for use in human or veterinary medicine.
The composition may be administered, for exam le, one to four times daily, p 1 preferably once or twice. The dosage will however depend on the nature and severity of the condition being treated, and it will also be appreciated that it may be necessary to make routine variations to the dosage depending on the age and weight of the patient.
The composition may take the form of for example tablets (including chewable tablets), capsules (of either the hard or soft type), powders or granules.
Tablets are preferred.
The composition according to the invention may be formulated using additional physiologically acceptable carriers or excipients as appropriate. Such additional carriers or excipients may be for example binding agents (e.g.
pregelatinised maize starch, polyvinylpyrrolidone or hydroxypropyl methylcellulose); fillers (e.g. lactose, n-ficrocrystalline cellulose or calcium hydrogen phosphate); lubricants (e.g. magnesium stearate, talc or silica); disintegrants (e.g.
starch or sodium starch glycollate); or wetting agents (e.g. sodium lauryl sulphate).
Tablets may be coated by methods well known in the art. The preparations may also contain flavouring, colouring and/or sweetening agents as appropriate.
Compositions according to the invention may be prepared according to conventional techniques well known in the pharmaceutical industry for the manufacture of solid dosage forms for oral administration. Thus the ranitidine HA156 bismuth carboxylate and alkaline salt may, for example, be blended with suitable excipients and, if desired, granulated. Tablets may be prepared, for example, by compression of the blend or granulate, using a lubricant as an aid to tabletting.
The following Examples illustrate tablets and capsules according to the invention in which the active ingredient is in particular ranitidine bismuth citrate.
Tablets may be film coated with suitable film forming materials, such as hydroxypropyl methyleellulose, using standard techniques.
Example I mg/tablet Active ingredient 200.0 400.0 800.0 Anhydrous sodium carbonate USNF 19.0 25.0 46.0 Microcrystalline cellulose Ph. Eur. 149.6 60.0 46.0 Polyvinylpyrrolidone 7.6 10.0 18.4 Magnesium stearate Ph. Eur. 3.8 5.0 9.2 Compression weight 380.0 500.0 919.6 The active ingredient, sodium carbonate and microcrystalline cellulose were blended together, granulated using a solution of the polyvinylpyrrolidone in isopropyl C5 alcohol, and dried. The granule was blended with magnesium stearate and compressed into tablets using suitable punches.
Example 2 mg/tablet Active ingredient 400.0 400.0 Sodium bicarbonate USNF 85.0 21.7 Polyvinylpyrrolidone 10.0 8.7 Magnesium stearate Ph. Eur. 5.0 4.4 Compression weight 500.0 434.8 HA156 The active ingredient and sodium bicarbonate were blended together, granulated using a solution of the polyvinylpyrrolidone in isopropyl alcohol, and dried. The granule was blended with magnesium stearate and compressed into tablets using suitable punches.
1 E) Examle 3 Active ingredient Anhydrous sodium carbonate USNF Sodium bicarbonate USNF Microcrystalline cellulose Ph. Eur. Polyvinylpyrrolidone Magnesium stearate Ph. Eur.
Compression weight mdtablets
400.0 2.5 22.5 60.0 10.0 5.0 500.0 Tablets were prepared according to the method described in Example 1, using the sodium carbonate and sodium bicarbonate in place of sodium carbonate alone.
Example 4
Active ingredient Anhydrous sodium carbonate USNF Lactose Polyvinylpyrrolidone Magnesium stearate Compression weight mg/tablets
600.0 36.0 60.0 15.0 8.0 719.0 The active ingredient, sodium carbonate and lactose are blended together, granulated using a solution of the polyvinylpyrrolidone in ethyl alcohol, and dried. The granule is blended with magnesium stearate and compressed into tablets using suitable punches.
HA156 Example 5 Active ingredient Sodium bicarbonate USNF Lactose Polyvinylpyrrolidone Magnesium.stearate Compression weight mOtablets 600.0 36.0 60.0 15.0 8.0 719.0 The active ingredient, sodium bicarbonate and lactose are blended together, granulated using a solution of the polyvinylpyrrolidone in isopropyl alcohol, and dried. The granule is blended with magnesium stearate and compressed into tablets using suitable punches.
Example 6
Active ingredient Anhydrous sodium carbonate USNIF Sodium bicarbonate USNF NEcrocrystalline cellulose Ph. Eur.
Polyvinylpyrrolidone Magnesium stearate Silicon dioxide Fill weight mp-lcaDsule 400.0 2.5 22.5 57.5 10.0 5.0 2.5 500.0 The active ingredient, sodium carbonate, sodium bicarbonate and microcrystalline cellulose are blended together, granulated using a solution of the polyvinylpyrrolidone in isopropyl alcohol, and dried. The granule is blended with magnesium stearate and silcon dioxide, and filled into hard gelatin capsules of a suitable size using conventional capsule filling machinery.
HA156 1 1 ExamDle 7 Active ingredient Anhydrous sodium carbonate USNF Microcrystalline cellulose Silicon dioxide mgtcai)sule 400.0 25.0 72.5 2.5 Fill 1 weight 500.0 The microcrystalline cellulose and silicon dioxide are blended to form a pre-blend.
This in turn is blended with the active ingredient and sodium carbonate. The resulting blend is filled into hard gelatin capsules of a suitable size using conventional capsule filling machinery.
Example 8 met 800.0 46.0 46.0 18.4 9.2 Active ingredient Anhydrous Sodium Carbonate USNF lyficrocrystalline Cellulose Ph.Eur Polyvinylpyrrolidone Magnesium Stearate 918.6 The active ingredient, sodium carbonate and microcystalline cellulose were blended together, granulated with a solution of the polyvinylpyrrolidone in a mixture of isopropyl alcohol and water (90:10) and dried. The granule was blended with magnesium stearate and compressed into tablets using suitable punches.
HA156 i I Example 9
Active ingredient Sodium Carbonate Lactose Polyvinylpyrrolidone Magnesium Stearate m,Jtablet 750.0 45.0 78.0 18.0 9.0 900.0 The active ingredient, sodium carbonate and lactose are blended together, granulated using a solution of polyvinylpyrrolidone in isopropyl alcohol and dried. The granule is blended with magnesium stearate and compressed into tablets using suitable punches.
310 HA156 1 9
Claims (13)
1. A pharmaceutical composition in solid unit dosage form adapted for oral administration, comprising a salt formed between ranitidine and a complex of bismuth with a carboxylic acid selected from tartaric acid and citric acid together with an alkaline salt.
2. A composition as claimed in claim 1, containing f rom 200 to 80Ong of ranitidine bismuth carboxylate per unit dose.
3. A composition as claimed in claim 1 or 2, containing from 2 to 20% w/w of the alkaline salt.
4. A composition as claimed in claim 1 or 2, containing from 2 to 8% w/w of the alkaline salt.
5. A composition as claimed in any of claims 1 to 4, containing from 50 to 95% w/w of ranitidine bismuth carboxylate.
6. A composition as claimed in any of claims 1 to 5, wherein the salt of ranitidine is:
N-[2-[[[5-[(dimethylanino)methyl]-2-furanyl]methyl) thio]ethyl]-Ni-methyl-2-nitro-l,l-ethenediamine 2-hydroxy1,2,3-propanetricarboxylate bismuth (3+) complex; or N-[2-[[[5-[(dinethylamino)methyl]-2-furanyl]methyl) thio]ethyl]-NI-methyl2-nitro-l,l-ethenediamine [R-(RR)]2,3-dihydroxybutanedioate bismuth (3+) complex.
7. A composition as claimed in any of claims 1 to 6 wherein the alkaline salt is a carbonate, bicarbonate, citrate, phosphate, acetate or chloride salt.
8. A composition as claimed in any of claims 1 to 6, wherein the alkaline salt is an alkali metal or an alkaline earth metal carbonate or bicarbonate or a mixture thereof.
9. A composition as claimed in any of claims 1 to 6, wherein the alkaline salt is sodium carbonate and/or sodium bicarbonate..
10. A composition as claimed in any of claims 1 to 5, wherein the ranitidine bismuth carboxylate is N-[2-[[[5[ (dimethylamino) methyl] -2 -f uranyl]methyl] thio] ethyl] -Nt - 7007/1 j 4 methyl-2-nitro-l,l-ethenediamine 2-hydroxy-1,2,3propanetricarboxylate bismuth (3+) complex and the alkaline salt is sodium carbonate.
11. A composition as claimed in any of claims 1 to 10 in the form of tablets.
12. A composition as claimed in any of claims 1 to 11, also containing one or more physiologically acceptable carriers or excipients.
13. A process for the preparation of a pharmaceutical composition as claimed in any of claims 1 to 12, which comprises processing the ranitidine bismuth carboxylate and the alkaline salt into a solid unit dosage form suitable for oral administration.
7007/1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909019875A GB9019875D0 (en) | 1990-09-11 | 1990-09-11 | Pharmaceutical compositions |
| NO920408A NO179694C (en) | 1990-09-11 | 1992-01-30 | Pharmaceutical preparations containing ranitidine derivatives |
| PCT/EP1992/000498 WO1993017679A1 (en) | 1990-09-11 | 1992-03-05 | Compositions containing ranitidine/bismuth carboxylates salts |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9119284D0 GB9119284D0 (en) | 1991-10-23 |
| GB2248185A true GB2248185A (en) | 1992-04-01 |
| GB2248185B GB2248185B (en) | 1994-02-02 |
Family
ID=47884627
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB909019875A Pending GB9019875D0 (en) | 1990-09-11 | 1990-09-11 | Pharmaceutical compositions |
| GB9119284A Expired - Fee Related GB2248185B (en) | 1990-09-11 | 1991-09-10 | Pharmaceutical compositions containing furan derivatives |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB909019875A Pending GB9019875D0 (en) | 1990-09-11 | 1990-09-11 | Pharmaceutical compositions |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US5456925A (en) |
| EP (1) | EP0558779B1 (en) |
| JP (1) | JPH0692849A (en) |
| KR (1) | KR100196308B1 (en) |
| AT (2) | AT405134B (en) |
| AU (2) | AU640816B2 (en) |
| BE (1) | BE1005115A5 (en) |
| BG (1) | BG61931B1 (en) |
| CA (1) | CA2050970C (en) |
| CH (1) | CH683068A5 (en) |
| CY (1) | CY1988A (en) |
| DE (2) | DE4130061A1 (en) |
| DK (1) | DK159191A (en) |
| ES (1) | ES2072647T3 (en) |
| FI (1) | FI944047A0 (en) |
| FR (1) | FR2666508B1 (en) |
| GB (2) | GB9019875D0 (en) |
| HK (1) | HK60894A (en) |
| HU (1) | HU211846A9 (en) |
| IE (1) | IE65049B1 (en) |
| IL (1) | IL99428A (en) |
| IT (1) | IT1249696B (en) |
| MX (1) | MX9101009A (en) |
| NL (1) | NL194907C (en) |
| NO (1) | NO179694C (en) |
| NZ (1) | NZ239731A (en) |
| OA (1) | OA10093A (en) |
| RO (1) | RO112084B1 (en) |
| RU (1) | RU2108097C1 (en) |
| SE (1) | SE509694C2 (en) |
| SK (1) | SK279591B6 (en) |
| WO (1) | WO1993017679A1 (en) |
| ZA (1) | ZA917176B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0558779A1 (en) * | 1990-09-11 | 1993-09-08 | Glaxo Group Limited | Compositions containing ranitidine/bismuth carboxylates salts |
| US5466436A (en) * | 1991-12-06 | 1995-11-14 | Glaxo Group Limited | Medicaments for treating inflammatory conditions or for analgesia |
| US5629297A (en) * | 1991-09-20 | 1997-05-13 | Glaxo Group Limited | Medicament for treating gastrointestinal disorders |
| US5817289A (en) * | 1995-01-26 | 1998-10-06 | Nycomed Imaging As | Non-cluster type bismuth compounds |
| US6117412A (en) * | 1995-01-26 | 2000-09-12 | Nycomed Imaging As | Non-cluster type bismuth compounds |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9127150D0 (en) * | 1991-12-20 | 1992-02-19 | Smithkline Beecham Plc | Novel treatment |
| AU1513699A (en) * | 1998-08-18 | 2000-03-14 | Nikolai Borisovich Leonidov | Physically stable and x-ray amorphous form of hydrochloride ranitidine having anincreased antitumoral activity and method for producing the same |
| EP1104673A1 (en) * | 1999-11-30 | 2001-06-06 | Bayer Classics | A hydrogen carbonate-containing, desintegrating agent-free pharmaceutical composition |
| KR100412290B1 (en) * | 2001-11-27 | 2003-12-31 | 주식회사 동구제약 | Composition of suspension containing ranitidine and its manufacturing process |
| US20060100271A1 (en) * | 2004-11-08 | 2006-05-11 | Keith Whitehead | Stabilized aqueous ranitidine compositions |
| US9629809B2 (en) | 2008-07-21 | 2017-04-25 | Si Group, Inc. | High content sodium ibuprofen granules, their preparation and their use in preparing non-effervescent solid dosage forms |
| MX337488B (en) * | 2008-07-21 | 2016-03-08 | Si Group Inc | High content sodium ibuprofen granules, their preparation and their use in preparing non-effervescent solid dosage forms. |
| CN115697354A (en) * | 2020-06-01 | 2023-02-03 | 香港大学 | Compositions and methods for treating SARS-COV-2 infection |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2220937A (en) * | 1988-07-18 | 1990-01-24 | Glaxo Group Ltd | Ranitidine derivatives |
| EP0367484A1 (en) * | 1988-10-26 | 1990-05-09 | Glaxo Group Limited | Carboxylic acid derivates |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4608257A (en) * | 1984-01-03 | 1986-08-26 | Board Of Regents For Oklahoma State University | Composition and method for treating heat stress |
| GB8629781D0 (en) * | 1986-12-12 | 1987-01-21 | Glaxo Group Ltd | Pharmaceutical compositions |
| ATE81011T1 (en) * | 1987-03-09 | 1992-10-15 | Procter & Gamble | COMPOSITIONS AND THEIR USE IN THE TREATMENT OF GASTROINTESTINAL DISORDERS. |
| DE3710462A1 (en) * | 1987-03-30 | 1988-10-13 | Heumann Pharma Gmbh & Co | PHARMACEUTICAL PREPARATION FOR THE TREATMENT OF DISEASES OF THE gastrointestinal tract |
| FR2633181B1 (en) * | 1988-06-24 | 1992-01-10 | Glaxo Lab Sa | RANITIDINE-BASED PHARMACEUTICAL COMPOSITION AND PROCESS FOR PREPARING THE SAME |
| EP0363502B1 (en) * | 1988-10-08 | 1991-09-25 | Dr. R. Pfleger Chemische Fabrik Gmbh | Liquid formulation containing bismuth, process to prepare it and use thereof |
| US5013560A (en) * | 1989-03-17 | 1991-05-07 | The Procter & Gamble Company | Microbially-stable bismuth-containing liquid pharmaceutical suspensions |
| GB9019875D0 (en) * | 1990-09-11 | 1990-10-24 | Glaxo Group Ltd | Pharmaceutical compositions |
-
1990
- 1990-09-11 GB GB909019875A patent/GB9019875D0/en active Pending
-
1991
- 1991-09-06 IL IL9942891A patent/IL99428A/en not_active IP Right Cessation
- 1991-09-09 CA CA002050970A patent/CA2050970C/en not_active Expired - Fee Related
- 1991-09-10 AU AU83757/91A patent/AU640816B2/en not_active Ceased
- 1991-09-10 NZ NZ239731A patent/NZ239731A/en unknown
- 1991-09-10 FR FR9111146A patent/FR2666508B1/en not_active Expired - Fee Related
- 1991-09-10 DK DK159191A patent/DK159191A/en not_active Application Discontinuation
- 1991-09-10 AT AT0180191A patent/AT405134B/en not_active IP Right Cessation
- 1991-09-10 GB GB9119284A patent/GB2248185B/en not_active Expired - Fee Related
- 1991-09-10 KR KR1019910015760A patent/KR100196308B1/en not_active IP Right Cessation
- 1991-09-10 ZA ZA917176A patent/ZA917176B/en unknown
- 1991-09-10 BE BE9100841A patent/BE1005115A5/en not_active IP Right Cessation
- 1991-09-10 DE DE4130061A patent/DE4130061A1/en not_active Withdrawn
- 1991-09-10 SE SE9102604A patent/SE509694C2/en not_active IP Right Cessation
- 1991-09-10 IT ITRM910673A patent/IT1249696B/en active IP Right Grant
- 1991-09-10 JP JP3230571A patent/JPH0692849A/en active Pending
- 1991-09-10 IE IE319191A patent/IE65049B1/en not_active IP Right Cessation
- 1991-09-10 CH CH2655/91A patent/CH683068A5/en not_active IP Right Cessation
- 1991-09-10 NL NL9101533A patent/NL194907C/en not_active IP Right Cessation
-
1992
- 1992-01-30 NO NO920408A patent/NO179694C/en not_active IP Right Cessation
- 1992-03-05 ES ES92103741T patent/ES2072647T3/en not_active Expired - Lifetime
- 1992-03-05 WO PCT/EP1992/000498 patent/WO1993017679A1/en active IP Right Grant
- 1992-03-05 AU AU13347/92A patent/AU1334792A/en not_active Abandoned
- 1992-03-05 SK SK1060-94A patent/SK279591B6/en unknown
- 1992-03-05 DE DE69202696T patent/DE69202696D1/en not_active Expired - Lifetime
- 1992-03-05 RO RO94-01459A patent/RO112084B1/en unknown
- 1992-03-05 AT AT92103741T patent/ATE122883T1/en not_active IP Right Cessation
- 1992-03-05 EP EP92103741A patent/EP0558779B1/en not_active Expired - Lifetime
- 1992-03-05 RU RU94040869A patent/RU2108097C1/en active
- 1992-03-05 MX MX9101009A patent/MX9101009A/en unknown
-
1994
- 1994-03-22 US US08/215,658 patent/US5456925A/en not_active Expired - Lifetime
- 1994-06-23 HK HK60894A patent/HK60894A/en not_active IP Right Cessation
- 1994-08-12 OA OA60553A patent/OA10093A/en unknown
- 1994-09-01 BG BG99021A patent/BG61931B1/en unknown
- 1994-09-02 FI FI944047A patent/FI944047A0/en unknown
-
1995
- 1995-06-28 HU HU95P/P00511P patent/HU211846A9/en unknown
-
1997
- 1997-09-05 CY CY198897A patent/CY1988A/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2220937A (en) * | 1988-07-18 | 1990-01-24 | Glaxo Group Ltd | Ranitidine derivatives |
| EP0367484A1 (en) * | 1988-10-26 | 1990-05-09 | Glaxo Group Limited | Carboxylic acid derivates |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0558779A1 (en) * | 1990-09-11 | 1993-09-08 | Glaxo Group Limited | Compositions containing ranitidine/bismuth carboxylates salts |
| WO1993017679A1 (en) * | 1990-09-11 | 1993-09-16 | Glaxo Group Limited | Compositions containing ranitidine/bismuth carboxylates salts |
| US5629297A (en) * | 1991-09-20 | 1997-05-13 | Glaxo Group Limited | Medicament for treating gastrointestinal disorders |
| US5466436A (en) * | 1991-12-06 | 1995-11-14 | Glaxo Group Limited | Medicaments for treating inflammatory conditions or for analgesia |
| US5817289A (en) * | 1995-01-26 | 1998-10-06 | Nycomed Imaging As | Non-cluster type bismuth compounds |
| US6117412A (en) * | 1995-01-26 | 2000-09-12 | Nycomed Imaging As | Non-cluster type bismuth compounds |
| US6303101B1 (en) | 1995-01-26 | 2001-10-16 | Nycomed Imaging As | Bismuth compounds |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20090910 |