EP0593573A1 - Pharmaceutical formulation of a beta-lactam antibiotic and clavulanic acid or a water-soluble salt thereof - Google Patents
Pharmaceutical formulation of a beta-lactam antibiotic and clavulanic acid or a water-soluble salt thereofInfo
- Publication number
- EP0593573A1 EP0593573A1 EP92914294A EP92914294A EP0593573A1 EP 0593573 A1 EP0593573 A1 EP 0593573A1 EP 92914294 A EP92914294 A EP 92914294A EP 92914294 A EP92914294 A EP 92914294A EP 0593573 A1 EP0593573 A1 EP 0593573A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- pharmaceutical formulation
- acid
- salt
- formulation according
- dicarboxylic acid
- 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.)
- Withdrawn
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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
Definitions
- This invention relates to pharmaceutical formulations, in particular to formulations containing ⁇ -lactam antibiotics and the ⁇ -lactamase inhibitor clavulanic acid or derivatives thereof, especially aqueous suspension formulations.
- compositions containing a ⁇ -lactam antibiotic and clavulanic acid or derivatives such as its salts are known.
- Clavulanic acid in aqueous suspension or solution is known to suffer to some extent from instability, and one significant determinant of stability is the pH of the aqueous medium of the suspension or solution, pH 5.8 - 6.2 being known to be the optimum.
- This invention provides novel improved pharmaceutical formulations containing clavulanic acid or derivatives thereof in which these problems have to some extent been alleviated, and further unexpected advantages have been achieved.
- the invention provides a pharmaceutical formulation comprising;
- the formulation may be an aqueous suspension or solution formulation, eg for oral administration or may alternatively be a dry powder, granular or tablet formulation provided primarily for reconstitution into an aqueous suspension or solution formulation.
- the one or more ⁇ -lactam antibiotics may be penicillins or cephalosporins, especially amox cillin and ampicillin, preferably amoxycillin in the form of its trihydrate.
- the clavulanic acid is preferably in the form of one of its salts with a pharmaceutically acceptable cation, especially potassium clavulanate.
- the weight ratio of antibiotic: clavulanic acid or clavulanate anion equivalent is in the range 12 : 1 to 1 : 1, suitably 8 : 1 to 1.5 : 1.
- concentration of antibiotic and clavulanic acid or clavulanate equivalent will vary depending upon the size of the unit dose in which it is intended to be administered.
- formulations for oral administration are administered in unit doses of around 5ml spoonfuls or as paediatric drops for small children.
- the total combined concentration of antibiotic and clavulanic acid or equivalent in such suspensions or solutions may be in the range 25 - 250 mg/ml, for example 30-125 mg/ml.
- the formulation is in the form of dry powder, granules or tablets for reconstitution the quantity of antibiotic and clavulanic acid or equivalent may be derived accordingly.
- the dicarboxylic acid salt eg. a succinic acid salt may be of a divalent cation such as calcium or other pharmaceutically acceptable cation, eg of a Group II metal, in which case a single such cation may replace both of the acidic hydrogen atoms.
- each acidic hydrogen atom may be replaced by a monovalent cation such as sodium, potassium or other pharmaceutically acceptable monovalent cation.
- Disodium succinate is preferred on account of its low cost, used in combination with succinic acid.
- the weight ratio of succinic acid : disodium succinate may be in the range 1 : 50 to 1 : 0.05 representing a molar ratio of succinic acid : succinic acid salt in the range 1 : 33 to 3 : 1.
- Suitable weight ratios of succinic acid : disodium succinate are around 1 : 30 to 1 : 15, for example 1 : 19 ⁇ 1.
- Typical weight ranges for other salts may be calculated from these ranges on the basis of the corresponding weight of succinate anion.
- the total molarity of succinic acid and succinate salt may be in the range 0.001M to 0.01M, suitably 0.001M to 0.0052 M, for example 0.005 ⁇ 0.0001 M.
- the formulation is in the form of dry powder, granules or tablets for reconstitution the quantity of succinic acid and succinate salt may be derived accordingly.
- the formulation may also optionally contain excipients which may be essentially conventional in the art.
- aqueous suspension or solution formulations may typically contain suspending agents such as Xantham gum, for example 0.25-5 mg/ml, suitably 0.5 - 2.5 mg/ml, thickening agents such as cellulose derivatives, for example 1 - 100 mg/ml if present, sweeteners such as aspartame or equivalent sugars, eg 0.5-5 mg/ml, and flavouring agents such as fruit flavourings and syrup flavourings, eg 10-20 mg/ml etc.
- suspending agents such as Xantham gum, for example 0.25-5 mg/ml, suitably 0.5 - 2.5 mg/ml
- thickening agents such as cellulose derivatives, for example 1 - 100 mg/ml if present
- sweeteners such as aspartame or equivalent sugars, eg 0.5-5 mg/ml
- flavouring agents such as fruit flavourings and syrup flavourings, eg 10-20 mg
- Silicas such as "Aerosil” may be present as thickening agents and/or as a powder flow aid, and other silicas such as "Syloid” may be present as an internal dessicant and bulking agent. Typically silicas may be present at eg 1-100 mg/ml. Dry powder, granule or tablet formulations for reconstitution may contain corresponding weights of these and/or other conventional excipients.
- Aqueous suspension and solution formulations of this invention may be provided in entirely conventional bottles etc, and dry powder or granule formulations for reconstitution may be provided in conventional jars, sachets etc which are advisedly airtight.
- the formulations of the invention appear to offer a number of advantages over known formulations which contain a ⁇ -lactam antibiotic in combination with clavulanic acid or clavulanate equivalent. These include improvement of stability in solution for example by 2-4% of the initial concentration on storage for 7 days at 5°C. The stability in solution is more robust in terms of pH differences in the water used to make up the suspension or solution and the quality of raw materials such as amoxycillin trihydrate. The presence of succinate ion appears to inhibit the colour change from white to pale cream that sometimes follows reconstitution, and there appears to be some enhancement of the flavour of reconstituted suspensions and solutions.
- the invention also provides a process for the preparation of such a pharmaceutical formulation, comprising admixing the ⁇ -lactam antibiotic, the clavulanic acid or salt thereof, the dicarboxylic acid and the salt thereof, and optionally any excipients, and optionally making the product up with water or an aqueous medium to form a suspension or solution formulation.
- the invention also provides a process for the use of a pharmaceutical formulation as described above in the manufacture of a medicament for the treatment of bacterial infections.
- the invention also provides a pharmaceutical formulation as described above for use in the treatment of bacterial infections.
- the invention also provides a method of treatment of bacterial infections in humans or animals which comprises the administration of a therapeutically effective amount of a pharmaceutical formulation as described above.
- a unit dose of 5ml of this suspension contains 156 mg of amoxycillin clavulanic acid combination.
- This suspension contains 112.5 mg per ml of amoxycillin clavulanic acid combination.
- a unit dose of 5 ml of this suspension contains 312 mg of amoxycillin/clavulanic acid combination.
- a unit dose of 5ml of this suspension contains 187 mg of amoxycillin clavulanic acid combination.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
Formulation pharmaceutique comprenant une ou plusieurs bêta-lactamines, de l'acide clavulanique ou un sel de celui-ci, soluble dans l'eau, un acide dicarboxylique pharmaceutiquement acceptable, et un sel de l'acide dicarboxylique, dans lequel les deux atomes d'hydrogène acides sont remplacés par un cation.A pharmaceutical formulation comprising one or more beta-lactams, clavulanic acid or a salt thereof, soluble in water, a pharmaceutically acceptable dicarboxylic acid, and a salt of the dicarboxylic acid, in which the two atoms of hydrogen acids are replaced by a cation.
Description
PHARMACEUTICAL FORMULATION OF A BETA-LACTAM ANTIBIOTIC AND CLAVULANIC ACID OR A WATER SOLUABLE SALT THEREOF
This invention relates to pharmaceutical formulations, in particular to formulations containing β-lactam antibiotics and the β-lactamase inhibitor clavulanic acid or derivatives thereof, especially aqueous suspension formulations.
Pharmaceutical formulations containing a β-lactam antibiotic and clavulanic acid or derivatives such as its salts are known. Clavulanic acid in aqueous suspension or solution is known to suffer to some extent from instability, and one significant determinant of stability is the pH of the aqueous medium of the suspension or solution, pH 5.8 - 6.2 being known to be the optimum.
At present the pH of pharmaceutical formulations containing clavulanic acid in suspension or solution is modified by including succinic acid in the formulation. Attempts have been made to further control the pH by the use of buffer salts, but it is found that many commonly used pharmaceutically acceptable buffer salts such as phosphate, citrate, carbonate etc have a catalytic effect deleterious to the stability of the clavulanic acid, and moreover the increased ionic strength of the suspension is also believed to be deleterious to clavulanic acid stability.
This invention provides novel improved pharmaceutical formulations containing clavulanic acid or derivatives thereof in which these problems have to some extent been alleviated, and further unexpected advantages have been achieved.
Accordingly the invention provides a pharmaceutical formulation comprising;
one or more β-lactam antibiotics;
clavulanic acid or a water-soluble salt thereof;
a pharmaceutically acceptable dicarboxylic acid, and;
a salt of the dicarboxylic acid in which both acidic hydrogen atoms are
replaced by a cation.
The formulation may be an aqueous suspension or solution formulation, eg for oral administration or may alternatively be a dry powder, granular or tablet formulation provided primarily for reconstitution into an aqueous suspension or solution formulation.
The one or more β-lactam antibiotics may be penicillins or cephalosporins, especially amox cillin and ampicillin, preferably amoxycillin in the form of its trihydrate. The clavulanic acid is preferably in the form of one of its salts with a pharmaceutically acceptable cation, especially potassium clavulanate.
Typically the weight ratio of antibiotic: clavulanic acid or clavulanate anion equivalent is in the range 12 : 1 to 1 : 1, suitably 8 : 1 to 1.5 : 1. In an aqueous suspension or solution formulation the concentration of antibiotic and clavulanic acid or clavulanate equivalent will vary depending upon the size of the unit dose in which it is intended to be administered. Typically formulations for oral administration are administered in unit doses of around 5ml spoonfuls or as paediatric drops for small children. Typically the total combined concentration of antibiotic and clavulanic acid or equivalent in such suspensions or solutions may be in the range 25 - 250 mg/ml, for example 30-125 mg/ml. When the formulation is in the form of dry powder, granules or tablets for reconstitution the quantity of antibiotic and clavulanic acid or equivalent may be derived accordingly.
Typical pharmaceutically acceptable dicarboxylic acids are those having a general formula HOOC.(CH2)nCOOH wherein n is 1-6 and in which two adjacent (CH2) groups may be replaced by CH=CH, for example succinic acid, malonic acid, maleic acid and fumaric acid. Of these succinic acid is preferred.
The dicarboxylic acid salt, eg. a succinic acid salt may be of a divalent cation such as calcium or other pharmaceutically acceptable cation, eg of a Group II metal, in which case a single such cation may replace both of the acidic hydrogen atoms. Alternatively each acidic hydrogen atom may be replaced by a monovalent cation such as sodium, potassium or other
pharmaceutically acceptable monovalent cation. Disodium succinate is preferred on account of its low cost, used in combination with succinic acid.
Typically the weight ratio of succinic acid : disodium succinate may be in the range 1 : 50 to 1 : 0.05 representing a molar ratio of succinic acid : succinic acid salt in the range 1 : 33 to 3 : 1. Suitable weight ratios of succinic acid : disodium succinate are around 1 : 30 to 1 : 15, for example 1 : 19 ± 1. Typical weight ranges for other salts may be calculated from these ranges on the basis of the corresponding weight of succinate anion. Typically in an aqueous suspension or solution formulation the total molarity of succinic acid and succinate salt may be in the range 0.001M to 0.01M, suitably 0.001M to 0.0052 M, for example 0.005 ± 0.0001 M. When the formulation is in the form of dry powder, granules or tablets for reconstitution the quantity of succinic acid and succinate salt may be derived accordingly.
The formulation may also optionally contain excipients which may be essentially conventional in the art. For example aqueous suspension or solution formulations may typically contain suspending agents such as Xantham gum, for example 0.25-5 mg/ml, suitably 0.5 - 2.5 mg/ml, thickening agents such as cellulose derivatives, for example 1 - 100 mg/ml if present, sweeteners such as aspartame or equivalent sugars, eg 0.5-5 mg/ml, and flavouring agents such as fruit flavourings and syrup flavourings, eg 10-20 mg/ml etc. Silicas such as "Aerosil" may be present as thickening agents and/or as a powder flow aid, and other silicas such as "Syloid" may be present as an internal dessicant and bulking agent. Typically silicas may be present at eg 1-100 mg/ml. Dry powder, granule or tablet formulations for reconstitution may contain corresponding weights of these and/or other conventional excipients.
Aqueous suspension and solution formulations of this invention may be provided in entirely conventional bottles etc, and dry powder or granule formulations for reconstitution may be provided in conventional jars, sachets etc which are advisedly airtight.
The formulations of the invention appear to offer a number of advantages over known formulations which contain a β-lactam antibiotic in
combination with clavulanic acid or clavulanate equivalent. These include improvement of stability in solution for example by 2-4% of the initial concentration on storage for 7 days at 5°C. The stability in solution is more robust in terms of pH differences in the water used to make up the suspension or solution and the quality of raw materials such as amoxycillin trihydrate. The presence of succinate ion appears to inhibit the colour change from white to pale cream that sometimes follows reconstitution, and there appears to be some enhancement of the flavour of reconstituted suspensions and solutions.
The invention also provides a process for the preparation of such a pharmaceutical formulation, comprising admixing the β-lactam antibiotic, the clavulanic acid or salt thereof, the dicarboxylic acid and the salt thereof, and optionally any excipients, and optionally making the product up with water or an aqueous medium to form a suspension or solution formulation.
The invention also provides a process for the use of a pharmaceutical formulation as described above in the manufacture of a medicament for the treatment of bacterial infections.
The invention also provides a pharmaceutical formulation as described above for use in the treatment of bacterial infections.
The invention also provides a method of treatment of bacterial infections in humans or animals which comprises the administration of a therapeutically effective amount of a pharmaceutical formulation as described above.
The invention will now be described by way of example only. In these examples the abbreviation (fa) as used in connection with amoxycillin trihydrate and potassium clavulanate indicates that the weight is expressed as the equivalent of free acid, ie respectively amoxycillin and clavulanic acid.
A unit dose of 5ml of this suspension contains 156 mg of amoxycillin clavulanic acid combination.
This suspension contains 112.5 mg per ml of amoxycillin clavulanic acid combination.
A unit dose of 5 ml of this suspension contains 312 mg of amoxycillin/clavulanic acid combination.
The above three suspensions were made up in an entirely conventional manner by adding the ingredients to cold water and stirring. Shaking of the reconstituted suspension immediately prior to administration was found to be desirable to ensure resuspension.
A unit dose of 5ml of this suspension contains 187 mg of amoxycillin clavulanic acid combination.
Claims
1. A pharmaceutical formulation comprising; one or more β-lactam antibiotics; clavulanic acid or a water-soluble salt thereof; a pharmaceutically acceptable dicarboxylic acid, and; a salt of the dicarboxylic acid in which both acidic hydrogen atoms are replaced by a cation.
2. A pharmaceutical formulation according to claim 1 wherein the β- lactam antibiotic is amoxycillin or ampicillin.
3. A pharmaceutical formulation according to claim 1 or 2 wherein the clavulanic acid is in the form of potassium clavulanate.
4. A pharmaceutical formulation according to any one of the preceding claims wherein the ratio of antibiotic : clavulanic acid is in the range 12 :
1 to 1 : 1.
5. A pharmaceutical formulation according to any one of the preceding claims wherein the dicarboxylic acid has a general formula HOOC.(CH2)n-COOH wherein n is 1-6 and in which two adjacent (CH2) groups may be replaced by CH = CH.
6. A pharmaceutical formulation according to claim 5 wherein the dicarboxylic acid is selected from succinic acid, maleic acid, malonic acid and fumaric acid.
7. A pharmaceutical formulation according to any one of the preceding claims wherein the dicarboxylic acid salt is of a divalent cation which replaces both acidic hydrogen atoms.
8. A pharmaceutical formulation according to any one of claims 1-6 in which in the salt of the dicarboxylic acid each acidic hydrogen atom is replaced by a single monovalent cation.
9. A pharmaceutical formulation according to claim 8 wherein the salt of the dicarboxylic acid is disodium succinate.
10. A pharmaceutical formulation according to claim 9 wherein the molar ratio succinic acid : disodium succinate is in the range 1 : 33 to 3 : 1.
11. A pharmaceutical formulation according to claim 9 or 10 being an aqueous solution or suspension and having a total molarity of succinic acid and succinate salt in the range 0.001M to 0.01M.
12. A pharmaceutical formulation according to any one of the preceding claims substantially as hereinbefore described with reference to examples l to 4.
13. A process for the preparation of a pharmaceutical formulation as claimed in any one of claims 1 to 12, comprising admixing the β-lactam antibiotic, the clavulanic acid or salt thereof, the dicarboxylic acid and the salt thereof, and optionally any excipients, and optionally making the product up with water or an aqueous medium to form a suspension or solution formulation.
14. A process for the use of a pharmaceutical formulation as claimed in any one of claims 1 to 12 in the manufacture of a medicament for the treatment of bacterial infections.
15. A pharmaceutical formulation as claimed in any one of claims 1 to 12 for use in the treatment of bacterial infections.
16. A method of treatment of bacterial infections in humans or animals which comprises the administration of a therapeutically effective amount of a pharmaceutical formulation as claimed in any one of claims 1 to 12.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9114950 | 1991-07-11 | ||
| GB919114950A GB9114950D0 (en) | 1991-07-11 | 1991-07-11 | Pharmaceutical formulation |
| PCT/GB1992/001207 WO1993000898A1 (en) | 1991-07-11 | 1992-07-03 | Pharmaceutical formulation of a beta-lactam antibiotic and clavulanic acid or a water-soluble salt thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0593573A1 true EP0593573A1 (en) | 1994-04-27 |
Family
ID=10698173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP92914294A Withdrawn EP0593573A1 (en) | 1991-07-11 | 1992-07-03 | Pharmaceutical formulation of a beta-lactam antibiotic and clavulanic acid or a water-soluble salt thereof |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0593573A1 (en) |
| JP (1) | JPH06508844A (en) |
| AU (1) | AU2230692A (en) |
| GB (1) | GB9114950D0 (en) |
| WO (1) | WO1993000898A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011142730A1 (en) | 2010-05-14 | 2011-11-17 | Mahmut Bilgic | Pharmaceutical composition comprising cefixime and clavulanic acid derivative compound |
| WO2011142731A2 (en) | 2010-05-14 | 2011-11-17 | Mahmut Bilgic | Formulations comprising a third generation cephalosporin and clavulanic acid |
| WO2011152808A1 (en) | 2010-06-03 | 2011-12-08 | Mahmut Bilgic | Formulation comprising cefpodoxime proxetil and clavulanic acid |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3501289B2 (en) | 1995-09-07 | 2004-03-02 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | Pharmaceutical prescription |
| US5759579A (en) * | 1996-12-05 | 1998-06-02 | American Home Products Corporation | Pharmaceutical suspension systems |
| DE19706978A1 (en) * | 1997-02-21 | 1998-08-27 | Ulrich Dr Posanski | Combination preparation for oral antibiotics |
| US20010016577A1 (en) * | 1998-08-24 | 2001-08-23 | Douglas Joseph Dobrozsi | Oral mucoadhesive compositions containing gastrointestinal actives |
| US6878386B1 (en) | 1999-04-13 | 2005-04-12 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection comprising amoxycillin and potassium clavulanate |
| US7250176B1 (en) | 1999-04-13 | 2007-07-31 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection |
| US6294199B1 (en) | 1999-04-13 | 2001-09-25 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection comprising administering amoxycillin |
| AU2001292185A1 (en) | 2000-10-12 | 2002-04-22 | Beecham Pharmaceuticals (Pte) Limited | Formulation containing amoxicillin |
| US6756057B2 (en) | 2000-10-12 | 2004-06-29 | Beecham Pharmaceuticals (Pte) Limited | Amoxicillin and potassium clavulanate dosage form |
| CN101267815B (en) | 2005-09-22 | 2013-11-06 | 明治制果药业株式会社 | Metal-beta-lactamase inhibitor |
| TR201000688A2 (en) * | 2010-01-29 | 2011-08-22 | B�Lg�� Mahmut | Effervescent formulations containing cefaclor and clavulanic acid as active ingredient. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3266580D1 (en) * | 1981-12-02 | 1985-10-31 | Beecham Group Plc | Pharmaceutical formulation comprising beta-lactam antibiotics |
| GB9007945D0 (en) * | 1990-04-07 | 1990-06-06 | Beecham Group Plc | Pharmaceutical formulation |
-
1991
- 1991-07-11 GB GB919114950A patent/GB9114950D0/en active Pending
-
1992
- 1992-07-03 WO PCT/GB1992/001207 patent/WO1993000898A1/en not_active Application Discontinuation
- 1992-07-03 AU AU22306/92A patent/AU2230692A/en not_active Abandoned
- 1992-07-03 JP JP5502080A patent/JPH06508844A/en active Pending
- 1992-07-03 EP EP92914294A patent/EP0593573A1/en not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9300898A1 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011142730A1 (en) | 2010-05-14 | 2011-11-17 | Mahmut Bilgic | Pharmaceutical composition comprising cefixime and clavulanic acid derivative compound |
| WO2011142731A2 (en) | 2010-05-14 | 2011-11-17 | Mahmut Bilgic | Formulations comprising a third generation cephalosporin and clavulanic acid |
| WO2011152808A1 (en) | 2010-06-03 | 2011-12-08 | Mahmut Bilgic | Formulation comprising cefpodoxime proxetil and clavulanic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06508844A (en) | 1994-10-06 |
| AU2230692A (en) | 1993-02-11 |
| WO1993000898A1 (en) | 1993-01-21 |
| GB9114950D0 (en) | 1991-08-28 |
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Legal Events
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|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
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|
| 17P | Request for examination filed |
Effective date: 19931116 |
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| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): BE CH DE FR GB IT LI NL |
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| 17Q | First examination report despatched |
Effective date: 19980203 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 19980814 |