WO2005067895A1 - Controlled release pharmaceutical compositions - Google Patents

Controlled release pharmaceutical compositions Download PDF

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Publication number
WO2005067895A1
WO2005067895A1 PCT/EP2005/000322 EP2005000322W WO2005067895A1 WO 2005067895 A1 WO2005067895 A1 WO 2005067895A1 EP 2005000322 W EP2005000322 W EP 2005000322W WO 2005067895 A1 WO2005067895 A1 WO 2005067895A1
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WO
WIPO (PCT)
Prior art keywords
controlled release
water soluble
soluble hydrophilic
formulation according
sodium
Prior art date
Application number
PCT/EP2005/000322
Other languages
French (fr)
Inventor
Seetharaman Sritharan
Harsha M. Dabhade
Sunilendu Bhushan Roy
Original Assignee
Sandoz Ag
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Filing date
Publication date
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Publication of WO2005067895A1 publication Critical patent/WO2005067895A1/en

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    • 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
    • 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
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
    • A61K31/546—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine containing further heterocyclic rings, e.g. cephalothin
    • 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
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • 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
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • 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
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
    • 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
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose

Definitions

  • This invention relates to pharmaceutical compositions of the I-acetoxyethyl ester of the antibiotic compound cefuroxime, known as cefuroxime axetil. More particularly this invention relates to controlled release formulations of cefuroxime axetil and a process for the preparation thereof.
  • Drugs containing an active ingredient with a relatively short biological half life often need to be administered several times a day in order to achieve the desired therapeutic effect.
  • controlled delivery systems have been developed which avoid the need for such multiple administrations. Controlled release systems not only reduce the frequency of administration but also contribute to improved patient compliance and can reduce side effects.
  • one object of the present invention is the provision of a controlled release formulation of cefuroxime axetil.
  • the present invention provides a controlled release pharmaceutical formulation comprising cefuroxime axetil and a water soluble hydrophilic agent.
  • a suitable water soluble hydrophilic agent according to the present invention is sodium chloride.
  • the present invention provides a process for the preparation of a controlled release pharmaceutical formulation of cefuroxime axetil comprising mixing cefuroxime axetil with a water soluble hydrophilic agent.
  • the cefuroxime axetil may be in any form, e.g. in a crystalline form, an amorphous form, or in the form of a solid solution in a polymer.
  • the cefuroxime axetil is in the form of a solid solution in a polymer.
  • Suitable polymers include homo- and copolymers of a polyvinylpyrrolidone, polyethylene glycol, polyethylene oxide and cellulose.
  • Suitable water soluble hydrophilic agents are those having a solubility in water at room temperature of at least 1mg/1000ml.
  • Suitable water soluble hydrophilic agents include sodium chloride, potassium chloride, sulphates of sodium, potassium or magnesium, citric acid and salts thereof, lactic acid and salts thereof, fumaric acid and salts thereof, sodium carbonate, sodium bicarbonate, sodium lauryl sulphate, lactose, sucrose, tween, polyethylene glycol, mannitol, sorbitol and cetrimide.
  • Preferred water soluble hydrophilic agents include sodium chloride, potassium chloride, sulphates of sodium, potassium or magnesium, citric acid and salts thereof, lactic acid and salts thereof, fumaric acid and salts thereof, sodium carbonate and sodium bicarbonate,. More preferred water soluble hydrophilic agents include sodium chloride, potassium chloride, sulphates of sodium, potassium or magnesium. In particular preferred water soluble hydrophilic agents are sodium chloride or potassium chloride.
  • the cefuroxime axetil active ingredient and the water soluble hydrophilic agent are preferably present in a ratio between the range of 1 :0.1 to 0.1:1.
  • the amount of water soluble hydrophilic agent in the formulations of the present invention is preferably at least 5% by weight, e.g. at least 10% by weight.
  • a formulation according to the present invention may optionally comprise a rate controlling polymer or a mixture of rate controlling polymers.
  • Suitable rate controlling polymers include water soluble polymers, for instancecellulose derivatives, acrylic acid derivatives, polyoxyethylene glycols and polyvinyl alcohols. Polysaccharides or N-vinyl-2- pyrrolidone/vinyl acetate copolymers are excluded.
  • Preferred rate controlling polymers are cellulose derivatives and acrylic acid derivatives. Suitable cellulose derivatives include carboxymethyl cellulose, calcium carboxymethyl cellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, hydroxypropylmethyl cellulose and ethyl cellulose.
  • a preferred rate controlling polymer is a commercially available hydroxypropylmethyl cellulose e.g. Methocel K 4 MCR, Methocel K 4 M Premium. If desired, variation of the dissolution profile can be achieved by adjusting the ratio between the water soluble hydrophilic agent(s) and a rate controlling polymer(s).
  • a formulation according to the present invention may comprise additional ingredients such as one or more further active drug compound(s) and/or one or more pharmaceutically acceptable excipients as conventionally used, such as for instance diluents, e.g. lactose, , mannitol, starch; binders, e.g. polyvinyl pyrrolidone (PVP),; lubricants/glidants.e.g. magnesium stearate, talc, stearic acid, colloidal sodium dioxide; and also flavoring agents, taste masking agents, colouring agents, pigments, and preservatives.
  • diluents e.g. lactose, , mannitol, starch
  • binders e.g. polyvinyl pyrrolidone (PVP),
  • lubricants/glidants e.g. magnesium stearate, talc, stearic acid, colloidal sodium dioxide
  • flavoring agents taste masking agents, colouring
  • the controlled release formulations of the present invention are particularly suitable for oral administration.
  • Any orally administrable dosage form is contemplated by the present invention, in particular a tablet, a capsule, a pellet, or a sachet form.
  • the dosage form may be prepared according to conventional methods. For instance methods for the preparation of tablets or capsules may include direct compression, dry granulation, wet granulation. For dry granulation processes one suitable method of granule formation is compaction.
  • the controlled release formulation is in the form a tablet or capsule.
  • a tablet according to the present invention may be uncoated or coated, e.g. by a film or other conventional coating, using known methods.
  • the formulation is a once daily administrable formulation, e.g. a tablet for once daily administration.
  • a unit dosage form of a formulation according to the present invention may comprise an amount of cefuroxime axetil as conventional.
  • the pharmaceutical formulations according to the present invention provide controlled release of cefuroxime axetil.
  • the present invention is further illustrated by the following non-limiting examples.
  • cefuroxime axetil, Mg. Stearate, Avicel and sodium chloride are mixed and compressed into tablet form using a 16 mm round punch.
  • the resulting tablets are then passed through a sieve number 16 to get granules.
  • the granules are then lubricated with the remaining ingredients.
  • the lubricated material is compressed into tablets using a 19X9 mm caplet shape punch.
  • cefuroxime axetil, Sodium chloride and Avicel are mixed and compacted using roller compactor.
  • Compacted ribbons passed through a sieve number 16 to get granules.
  • the granules are then mixed with the remaining ingredients.
  • the mixed material is compressed into tablets using a 19 X 9 mm caplet shape punch.
  • Dissolution medium USP II; 0.1 N HCL; 100 rpm Time (Hrs) % of drug release 1 6 2 13 4 26 6 36 8 43 10 49 12 52 16 57
  • cefuroxime axetil, Sodium chloride and Avicel are mixed and compacted using roller compactor.
  • Compacted ribbons passed through a sieve number 16 to get granules.
  • the granules are then mixed with the remaining ingredients.
  • the mixed material is compressed into tablets using a 19X9 mm caplet shape punch.
  • Dissolution medium USP II; 0.1 N HCL; 100 rpm Time (Hrs) % of drug release 1 13 2 46 4 73 6 81 8 83 10 84
  • cefuroxime axetil, Mg. Stearate, and Avicel are mixed and compressed into tablet form using a 16 mm round punch.
  • the resulting tablets are then passed through a sieve number 16 to get granules.
  • the granules are then lubricated with the remaining ingredients.
  • the lubricated material is compressed into tablets using a 19X9 mm caplet shape punch.
  • Dissolution medium USP II; Phosphate buffer pH 6.8; 50 rpm
  • cefuroxime axetil, Mg. Stearate, Avicel and Methocel are mixed and compressed into tablet form using a 16 mm round punch.
  • the resulting tablets are then passed through a sieve number 16 to get granules.
  • the granules are then lubricated with the remaining ingredients.
  • the lubricated material is compressed into tablets using a 19X9 mm caplet shape punch.

Abstract

This invention relates to pharmaceutical compositions of the I-acetoxyethyl ester of the antibiotic compound cefuroxime, known as cefuroxime axetil. The invention more prticularly relates to controlled release formulations of cefuroxime axetil, containing one or more water soluble hydrophilic agents.

Description

Controlled Release Pharmaceutical Compositions
This invention relates to pharmaceutical compositions of the I-acetoxyethyl ester of the antibiotic compound cefuroxime, known as cefuroxime axetil. More particularly this invention relates to controlled release formulations of cefuroxime axetil and a process for the preparation thereof.
Drugs containing an active ingredient with a relatively short biological half life often need to be administered several times a day in order to achieve the desired therapeutic effect. For many such drugs controlled delivery systems have been developed which avoid the need for such multiple administrations. Controlled release systems not only reduce the frequency of administration but also contribute to improved patient compliance and can reduce side effects.
It is known that some drugs, such as cefuroxime axetil, inherently form a gel upon contact with water. Such gel formulation can lead to poor dissolution and reduced absorption of the active ingredient. Instant release tablet formulations have been developed by incorporating the active ingredient with disintegrating agents (Superdisintegrants). These disintegrating agents cause almost immediate bursting of the tablet, allowing rapid dispersion and dissolution of the drug before gel formation with water can occur. However, this inherent gel forming property is problematic for the production of useful controlled release formulations of cefuroxime axetil.
Thus one object of the present invention is the provision of a controlled release formulation of cefuroxime axetil.
According to one aspect the present invention provides a controlled release pharmaceutical formulation comprising cefuroxime axetil and a water soluble hydrophilic agent.
A suitable water soluble hydrophilic agent according to the present invention is sodium chloride. ln another aspect the present invention provides a process for the preparation of a controlled release pharmaceutical formulation of cefuroxime axetil comprising mixing cefuroxime axetil with a water soluble hydrophilic agent.
The cefuroxime axetil may be in any form, e.g. in a crystalline form, an amorphous form, or in the form of a solid solution in a polymer. Preferably the cefuroxime axetil is in the form of a solid solution in a polymer. Suitable polymers include homo- and copolymers of a polyvinylpyrrolidone, polyethylene glycol, polyethylene oxide and cellulose.
Any water soluble hydrophilic agent, or mixture of water soluble hydrophilic agents, is contemplated by the present invention. Suitable water soluble hydrophilic agents are those having a solubility in water at room temperature of at least 1mg/1000ml. Suitable water soluble hydrophilic agents include sodium chloride, potassium chloride, sulphates of sodium, potassium or magnesium, citric acid and salts thereof, lactic acid and salts thereof, fumaric acid and salts thereof, sodium carbonate, sodium bicarbonate, sodium lauryl sulphate, lactose, sucrose, tween, polyethylene glycol, mannitol, sorbitol and cetrimide.
Preferred water soluble hydrophilic agents include sodium chloride, potassium chloride, sulphates of sodium, potassium or magnesium, citric acid and salts thereof, lactic acid and salts thereof, fumaric acid and salts thereof, sodium carbonate and sodium bicarbonate,. More preferred water soluble hydrophilic agents include sodium chloride, potassium chloride, sulphates of sodium, potassium or magnesium. In particular preferred water soluble hydrophilic agents are sodium chloride or potassium chloride.
The cefuroxime axetil active ingredient and the water soluble hydrophilic agent are preferably present in a ratio between the range of 1 :0.1 to 0.1:1. The amount of water soluble hydrophilic agent in the formulations of the present invention is preferably at least 5% by weight, e.g. at least 10% by weight.
A formulation according to the present invention may optionally comprise a rate controlling polymer or a mixture of rate controlling polymers. Suitable rate controlling polymers include water soluble polymers, for instancecellulose derivatives, acrylic acid derivatives, polyoxyethylene glycols and polyvinyl alcohols. Polysaccharides or N-vinyl-2- pyrrolidone/vinyl acetate copolymers are excluded.. Preferred rate controlling polymers are cellulose derivatives and acrylic acid derivatives. Suitable cellulose derivatives include carboxymethyl cellulose, calcium carboxymethyl cellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, hydroxypropylmethyl cellulose and ethyl cellulose. A preferred rate controlling polymer is a commercially available hydroxypropylmethyl cellulose e.g. Methocel K 4 MCR, Methocel K 4 M Premium. If desired, variation of the dissolution profile can be achieved by adjusting the ratio between the water soluble hydrophilic agent(s) and a rate controlling polymer(s).
A formulation according to the present invention may comprise additional ingredients such as one or more further active drug compound(s) and/or one or more pharmaceutically acceptable excipients as conventionally used, such as for instance diluents, e.g. lactose, , mannitol, starch; binders, e.g. polyvinyl pyrrolidone (PVP),; lubricants/glidants.e.g. magnesium stearate, talc, stearic acid, colloidal sodium dioxide; and also flavoring agents, taste masking agents, colouring agents, pigments, and preservatives.
The controlled release formulations of the present invention are particularly suitable for oral administration. Any orally administrable dosage form is contemplated by the present invention, in particular a tablet, a capsule, a pellet, or a sachet form. The dosage form may be prepared according to conventional methods. For instance methods for the preparation of tablets or capsules may include direct compression, dry granulation, wet granulation. For dry granulation processes one suitable method of granule formation is compaction.
Preferably the controlled release formulation is in the form a tablet or capsule. A tablet according to the present invention may be uncoated or coated, e.g. by a film or other conventional coating, using known methods.
In a preferred embodiment the formulation is a once daily administrable formulation, e.g. a tablet for once daily administration.
A unit dosage form of a formulation according to the present invention may comprise an amount of cefuroxime axetil as conventional.
The pharmaceutical formulations according to the present invention provide controlled release of cefuroxime axetil. The present invention is further illustrated by the following non-limiting examples.
EXAMPLE 1 Cefuroxime axetil + water soluble hydrophilic agent Tablets are prepared according to the following process:
Figure imgf000005_0001
The cefuroxime axetil, Mg. Stearate, Avicel and sodium chloride are mixed and compressed into tablet form using a 16 mm round punch. The resulting tablets are then passed through a sieve number 16 to get granules. The granules are then lubricated with the remaining ingredients. The lubricated material is compressed into tablets using a 19X9 mm caplet shape punch.
Dissolution:
Medium for dissolution: USP II; 0.1 N HCI; 50 rpm
Results Time % of drug release 1 11 2 _ 22 4 43 6 58 8 70 12 86 16 91 20 94 24 99
Controlled drug release is observed over 24 hours. Complete drug release is observed after 24 hours. The above dissolution profile illustrates controlled release of cefuroxime axetil formulations according to the invention.
EXAMPLE 2 Cefuroxime axetil + rate controlling polymer + water soluble hydrophilic agent
Figure imgf000006_0001
The cefuroxime axetil, Sodium chloride and Avicel are mixed and compacted using roller compactor. Compacted ribbons passed through a sieve number 16 to get granules. The granules are then mixed with the remaining ingredients. The mixed material is compressed into tablets using a 19 X 9 mm caplet shape punch.
Dissolution: Dissolution medium: USP II; 0.1 N HCL; 100 rpm Time (Hrs) % of drug release 1 6 2 13 4 26 6 36 8 43 10 49 12 52 16 57
EXAMPLE 3 Cefuroxime axetil + rate controlling polymer + water soluble hydrophilic agent
Figure imgf000007_0001
The cefuroxime axetil, Sodium chloride and Avicel are mixed and compacted using roller compactor. Compacted ribbons passed through a sieve number 16 to get granules. The granules are then mixed with the remaining ingredients. The mixed material is compressed into tablets using a 19X9 mm caplet shape punch.
Dissolution: Dissolution medium: USP II; 0.1 N HCL; 100 rpm Time (Hrs) % of drug release 1 13 2 46 4 73 6 81 8 83 10 84
COMPARATIVE EXAMPLE 4 Cefuroxime axetil (no water soluble hydrophilic agent)
Figure imgf000008_0001
The cefuroxime axetil, Mg. Stearate, and Avicel are mixed and compressed into tablet form using a 16 mm round punch. The resulting tablets are then passed through a sieve number 16 to get granules. The granules are then lubricated with the remaining ingredients. The lubricated material is compressed into tablets using a 19X9 mm caplet shape punch.
Dissolution: Dissolution medium: USP II; Phosphate buffer pH 6.8; 50 rpm
Time % of drug release 1 8 2 13 3 18 4 22 5 26 6 28 24 47
COMPARATIVE EXAMPLE 5 Cefuroxime axetil + rate controlling polymer (no water soluble hydrophilic agent)
Figure imgf000009_0001
The cefuroxime axetil, Mg. Stearate, Avicel and Methocel are mixed and compressed into tablet form using a 16 mm round punch. The resulting tablets are then passed through a sieve number 16 to get granules. The granules are then lubricated with the remaining ingredients. The lubricated material is compressed into tablets using a 19X9 mm caplet shape punch.
Dissolution:
Dissolution medium:
USP II; Phosphate buffer pH 6.8; 50 rpm
Time % of drug release 1 7
2 10
3 13
4 15
5 17
6 18
25 30

Claims

1. A controlled release pharmaceutical formulation consisting of cefuroxime axetil, a water soluble hydrophilic agent, and optionally of a rate controlling polymer selected from the group consisting of cellulose derivatives, polyoxyethylene glycols, polyvinyl alcohols and acrylic acid derivatives, and/or diluents, and/or binders, and/or lubricants/glidants, and/or flavoring agents, and/or taste masking agents, and/or colouring agents, and/or pigments, and/or preservatives.
2. A controlled release formulation according to claim 1 comprising one or more water soluble hydrophilic agents selected from sodium chloride, potassium chloride, sulphates of sodium, potassium or magnesium, citric acid and salts thereof, lactic acid and salts thereof, fumaric acid and salts thereof, sodium carbonate and sodium bicarbonate.
3. A controlled release formulation according to claim 2 wherein the water soluble hydrophilic agent is sodium chloride or potassium chloride.
4. A controlled release formulation according to any one of the preceding claims wherein the amount of water soluble hydrophilic agent is at least 5% by weight.
5. A controlled release formulation according to any one of the preceding claims comprising a rate controlling polymer selected from cellulose derivatives, acrylic acid derivatives or a mixture thereof.
6. A formulation according to claim 5 wherein the rate controlling polymer is hydroxypropylmethyl cellulose.
7. A controlled release pharmaceutical formulation comprising cefuroxime axetil and a water soluble hydrophilic agent selected from sodium chloride, potassium chloride, sulphates of sodium, potassium or magnesium, citric acid and salts thereof, lactic acid and salts thereof, fumaric acid and salts thereof, sodium carbonate and sodium bicarbonate or any mixture thereof, and optionally a rate controlling polymer with the exception of polysaccharides or N- vinyl-2-pyrrolidone/vinyl acetate copolymers.
8. A controlled release formulation according to claim 7 wherein the water soluble hydrophilic agent is selected from sodium chloride, potassium chloride, sulphates of sodium, potassium or magnesium, or any mixture thereof.
9. A controlled release formulation according to claim 8 wherein the water soluble hydrophilic agent is selected from sodium chloride or potassium chloride.
10. A controlled release formulation according to any one of claims 7 to 9 wherein the rate controlling polymer is selected from cellulose derivatives, acrylic acid derivatives or a mixture thereof.
11. A controlled release pharmaceutical formulation comprising cefuroxime axetil together with a water soluble hydrophilic agent, and optionally a rate controlling polymer selected from cellulose derivatives, polyoxyethylene glycols, polyvinyl alcohols and acrylic acid derivatives as the sole rate controlling agents.
12. A formulation according to any one of the preceding claims wherein the formulation is for oral administration.
13. A formulation according to claim 12 wherein the formulation is a tablet dosage form for administration once a day.
14. A process for the preparation of a controlled release pharmaceutical formulation of cefuroxime axetil comprising mixing cefuroxime axetil with a water soluble hydrophilic agent.
PCT/EP2005/000322 2004-01-16 2005-01-14 Controlled release pharmaceutical compositions WO2005067895A1 (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009026725A1 (en) * 2007-08-31 2009-03-05 Noveko Inc. Antimicrobial compositions and fibres incorporating the same
US8905034B2 (en) 2010-11-05 2014-12-09 Salutaris Llp Ergonomic protective air filtration devices and methods for manufacturing the same

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999062559A1 (en) * 1998-05-29 1999-12-09 Bernard Charles Sherman Pharmaceutical tablets comprising cefuroxime axetil
WO2000056286A1 (en) * 1999-03-19 2000-09-28 Ranbaxy Laboratories Limited Process for the preparation of a bioavailable oral dosage form of cefuroxime axetil
WO2002036126A1 (en) * 2000-10-30 2002-05-10 Lupin Limited Rapidly disintegrating sustained release cefuroxime axetil composition
US20020136764A1 (en) * 2000-02-24 2002-09-26 Rudnic Edward M. Antibiotic product, use and formulation thereof
US6534494B1 (en) * 1997-09-29 2003-03-18 Ranbaxy Laboratories Limited Process for the preparation of cefuroxime axetil in an amorphous form
WO2004019901A2 (en) * 2002-08-30 2004-03-11 Orchid Chemicals & Pharmaceuticals Ltd. Sustained release pharmaceutical composition

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6534494B1 (en) * 1997-09-29 2003-03-18 Ranbaxy Laboratories Limited Process for the preparation of cefuroxime axetil in an amorphous form
WO1999062559A1 (en) * 1998-05-29 1999-12-09 Bernard Charles Sherman Pharmaceutical tablets comprising cefuroxime axetil
WO2000056286A1 (en) * 1999-03-19 2000-09-28 Ranbaxy Laboratories Limited Process for the preparation of a bioavailable oral dosage form of cefuroxime axetil
US20020136764A1 (en) * 2000-02-24 2002-09-26 Rudnic Edward M. Antibiotic product, use and formulation thereof
WO2002036126A1 (en) * 2000-10-30 2002-05-10 Lupin Limited Rapidly disintegrating sustained release cefuroxime axetil composition
WO2004019901A2 (en) * 2002-08-30 2004-03-11 Orchid Chemicals & Pharmaceuticals Ltd. Sustained release pharmaceutical composition

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009026725A1 (en) * 2007-08-31 2009-03-05 Noveko Inc. Antimicrobial compositions and fibres incorporating the same
US8905034B2 (en) 2010-11-05 2014-12-09 Salutaris Llp Ergonomic protective air filtration devices and methods for manufacturing the same

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