CA2425688A1 - Extended release erythromycin derivatives - Google Patents
Extended release erythromycin derivatives Download PDFInfo
- Publication number
- CA2425688A1 CA2425688A1 CA002425688A CA2425688A CA2425688A1 CA 2425688 A1 CA2425688 A1 CA 2425688A1 CA 002425688 A CA002425688 A CA 002425688A CA 2425688 A CA2425688 A CA 2425688A CA 2425688 A1 CA2425688 A1 CA 2425688A1
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- composition
- long chain
- host
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- bacterial infection
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Abstract
An extended release pharmaceutical composition comprised of an erythromycin derivative and non-polymer material for providing for extended release, in particular, a member selected from the group consisting of clays, long chain hydrocarbons, long chain carboxylic acids, long chain carboxylic acid esters, long chain alcohols, and mixtures thereof, with said member being present in an amount to provide for extended release of the erythromycin derivative.
Description
EXTENDED RELEASE ERYTHROMYCIN DERIVATIVES
The invention relates to a pharmaceutical composition of erythromycin derivatives with an extended release profile.
Erythromycin, as well as derivatives thereof, have been used as an antibacterial agent, and are generally provided as an immediate release composition.
U.S. Patent 6,010,718 discloses a pharmaceutical composition having extended release characteristics wherein erythromycin or a derivative thereof is employed in a pharmaceutical composition wherein the pharmaceutically acceptable carrier for the erythromycin or derivative thereof is a polymer, with such polymer generally being in an amount from about 5% to about 50% by weight of the composition.
In accordance with an aspect the present invention, there is provided a pharmaceutical composition for extended release of an erythromycin derivative wherein such erythromycin derivative is combined with a non-polymer hydrophobic material. Such material provides for extended release of the erythromycin derivative and is preferably at least one of a clay, a long chain hydrocarbon, a long chain alcohol, a long chain ester or a long chain acid.
More particularly, the extended release characteristics for the erythromycin derivative are provided by coating the erythromycin derivative with a clay, a long chain hydrocarbon, a long chain alcohol, a long chain ester, or a long chain acid.
A long chain hydrocarbon is a hydrocarbon that contains at least 12 carbon atoms, and in general, such a hydrocarbon contains from about 12 to 22 carbon atoms. The hydrocarbon may be branched or unbranched, or may be saturated or unsaturated, and; when unsaturated, may contain one or more double bonds.
A long chain carboxylic acid and/or long chain carboxylic acid ester and/or a long chain alcohol also preferably contains at least 12 carbon atoms, and more preferably, contains from 12 to 22 carbon atoms. In general, such hydrocarbons are aliphatic hydrocarbons, and may be saturated or unsaturated and may be branched or unbranched. If unsaturated, the hydrocarbon portion may contain one or more double bonds. In addition, such long chain alcohols, esters and acids may contain three carbon rings or hydroxyl groups.
Thus, for example, a long chain alcohol is represented by an aliphatic hydrocarbon alcohol that preferably contains at least 12 carbon atoms, and may contain one or more hydroxyl groups.
As representative examples of long chain carboxylic acids, there may be mentioned:
n-dodecanoic acid, a-tetradecanoic acid, a-hexadecanoic acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, montanic acid and melissic acid. Also useful are unsaturated monoolefinic straight chain monocarboxylic acids. Examples of these are oleic acid, gadoleic acid and erucic acid. Also useful are unsaturated (polyolefinic) straight chain monocarboxyilic acid.
Examples of these are linoleic acid, ricinoleic acid, linolenic acid, arachidonic acid and behenolic acid. Useful branched acids include, for example, diacetyl tartaric acid.
As representative examples of long chain carboxylic acid esters, there may be mentioned: glyceryl monostearates; glyceryl monopalmitates; mixtures of glyceryl monostearate and glyceryl monopalmitate (Myvaplex 600. Eastman Fine Chemical Company); glyceryl monolinoleate; glyceryl monooleate; mixtures of glyceryl monopalmitate, glyceryl monostearate, glyceryl monooleate and glyceryl monolinoleate (Myverol 18-92, Eastman Fine Chemical Company); glyceryl monolinolenate;
glyceryl monogadoleate; mixtures of glyceryl monopalmitate, glyceryl monostearate, glyceryl monooleate, glyceryl monolinoleate, glyceryl monolinolenate and glyceryl monogadoleate (Myverol 18-99, Eastman Fine Chemical Company); acetylated glycerides such as distilled acetylated monoglycerides (Myvacet S-07, 7-07 and 9-45, Eastman Fine Chemical Company); mixtures of propylene glycol monoesters, distilled monoglycerides, sodium stearoyl lactylate and silicon dioxide (Myvatex TL, Eastman Fine Chemical Company);
mixtures of propylene glycol monoesters, distilled monoglycerides, sodium stearoyl lactylate and silicon dioxide (Myvatex TL, Eastman Fine Chemical Company) d-alpha tocopherol polyethylene glycol 1000 succinate (Vitamin E TPGS, Eastman Chemical Company);
mixtures of mono- and di-glyceride esters such as Atmul (Humko Chemical Division of Witco Chemical); calcium stearoyl lactylate; ethoxylated mono- and di-glycerides; lactated mono- and di-glycerides; lactylate carboxylic acid ester of glycerol and propylene glycol;
lactylic esters of long chain carboxylic acids; polyglycerol esters of long chain carboxylic acids, propylene glycol mono- and di-esters of long chain carboxylic acids;
sodium stearoyl lactylate; sorbitan monostearate; sorbitan monooleate; other sorbitan esters of long chain carboxylic acids; stearyl heptanoate; cetyl esters of waxes; stearyl octanoate; Clo-C3o cholesterol/lavosterol esters; and sucrose long chain carboxylic acid esters.
As representative examples of clays, there may be mentioned: Kaolin, Bentonite, magnesium aluminum silicate, magnesium trisilicate, talc, or calcium silicate.
The erythromycin derivative is coated with a material as hereinabove described to provide for sustained release of the erythromycin derivative.
The extended released material, as hereinabove described, is generally employed in an amount of from about 1 % to about 60%, by weight of the composition, and preferably from about 5% to about 50% of the composition.
The composition may further include pharmaceutically acceptable excipients and/or fillers and extenders such as lactose, starches, dicalcium phosphate, calcium sulfate, calcium carbonate, glucose, sucrose, mannitol and silicic acid, lubricants such as talc, calcium stearate, magnesium stearate, etc.
The invention relates to a pharmaceutical composition of erythromycin derivatives with an extended release profile.
Erythromycin, as well as derivatives thereof, have been used as an antibacterial agent, and are generally provided as an immediate release composition.
U.S. Patent 6,010,718 discloses a pharmaceutical composition having extended release characteristics wherein erythromycin or a derivative thereof is employed in a pharmaceutical composition wherein the pharmaceutically acceptable carrier for the erythromycin or derivative thereof is a polymer, with such polymer generally being in an amount from about 5% to about 50% by weight of the composition.
In accordance with an aspect the present invention, there is provided a pharmaceutical composition for extended release of an erythromycin derivative wherein such erythromycin derivative is combined with a non-polymer hydrophobic material. Such material provides for extended release of the erythromycin derivative and is preferably at least one of a clay, a long chain hydrocarbon, a long chain alcohol, a long chain ester or a long chain acid.
More particularly, the extended release characteristics for the erythromycin derivative are provided by coating the erythromycin derivative with a clay, a long chain hydrocarbon, a long chain alcohol, a long chain ester, or a long chain acid.
A long chain hydrocarbon is a hydrocarbon that contains at least 12 carbon atoms, and in general, such a hydrocarbon contains from about 12 to 22 carbon atoms. The hydrocarbon may be branched or unbranched, or may be saturated or unsaturated, and; when unsaturated, may contain one or more double bonds.
A long chain carboxylic acid and/or long chain carboxylic acid ester and/or a long chain alcohol also preferably contains at least 12 carbon atoms, and more preferably, contains from 12 to 22 carbon atoms. In general, such hydrocarbons are aliphatic hydrocarbons, and may be saturated or unsaturated and may be branched or unbranched. If unsaturated, the hydrocarbon portion may contain one or more double bonds. In addition, such long chain alcohols, esters and acids may contain three carbon rings or hydroxyl groups.
Thus, for example, a long chain alcohol is represented by an aliphatic hydrocarbon alcohol that preferably contains at least 12 carbon atoms, and may contain one or more hydroxyl groups.
As representative examples of long chain carboxylic acids, there may be mentioned:
n-dodecanoic acid, a-tetradecanoic acid, a-hexadecanoic acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, montanic acid and melissic acid. Also useful are unsaturated monoolefinic straight chain monocarboxylic acids. Examples of these are oleic acid, gadoleic acid and erucic acid. Also useful are unsaturated (polyolefinic) straight chain monocarboxyilic acid.
Examples of these are linoleic acid, ricinoleic acid, linolenic acid, arachidonic acid and behenolic acid. Useful branched acids include, for example, diacetyl tartaric acid.
As representative examples of long chain carboxylic acid esters, there may be mentioned: glyceryl monostearates; glyceryl monopalmitates; mixtures of glyceryl monostearate and glyceryl monopalmitate (Myvaplex 600. Eastman Fine Chemical Company); glyceryl monolinoleate; glyceryl monooleate; mixtures of glyceryl monopalmitate, glyceryl monostearate, glyceryl monooleate and glyceryl monolinoleate (Myverol 18-92, Eastman Fine Chemical Company); glyceryl monolinolenate;
glyceryl monogadoleate; mixtures of glyceryl monopalmitate, glyceryl monostearate, glyceryl monooleate, glyceryl monolinoleate, glyceryl monolinolenate and glyceryl monogadoleate (Myverol 18-99, Eastman Fine Chemical Company); acetylated glycerides such as distilled acetylated monoglycerides (Myvacet S-07, 7-07 and 9-45, Eastman Fine Chemical Company); mixtures of propylene glycol monoesters, distilled monoglycerides, sodium stearoyl lactylate and silicon dioxide (Myvatex TL, Eastman Fine Chemical Company);
mixtures of propylene glycol monoesters, distilled monoglycerides, sodium stearoyl lactylate and silicon dioxide (Myvatex TL, Eastman Fine Chemical Company) d-alpha tocopherol polyethylene glycol 1000 succinate (Vitamin E TPGS, Eastman Chemical Company);
mixtures of mono- and di-glyceride esters such as Atmul (Humko Chemical Division of Witco Chemical); calcium stearoyl lactylate; ethoxylated mono- and di-glycerides; lactated mono- and di-glycerides; lactylate carboxylic acid ester of glycerol and propylene glycol;
lactylic esters of long chain carboxylic acids; polyglycerol esters of long chain carboxylic acids, propylene glycol mono- and di-esters of long chain carboxylic acids;
sodium stearoyl lactylate; sorbitan monostearate; sorbitan monooleate; other sorbitan esters of long chain carboxylic acids; stearyl heptanoate; cetyl esters of waxes; stearyl octanoate; Clo-C3o cholesterol/lavosterol esters; and sucrose long chain carboxylic acid esters.
As representative examples of clays, there may be mentioned: Kaolin, Bentonite, magnesium aluminum silicate, magnesium trisilicate, talc, or calcium silicate.
The erythromycin derivative is coated with a material as hereinabove described to provide for sustained release of the erythromycin derivative.
The extended released material, as hereinabove described, is generally employed in an amount of from about 1 % to about 60%, by weight of the composition, and preferably from about 5% to about 50% of the composition.
The composition may further include pharmaceutically acceptable excipients and/or fillers and extenders such as lactose, starches, dicalcium phosphate, calcium sulfate, calcium carbonate, glucose, sucrose, mannitol and silicic acid, lubricants such as talc, calcium stearate, magnesium stearate, etc.
In accordance with the present invention, unlike U.S. Patent 6,010,718, extended release properties are achieved without using a polymer to provide such properties.
Although extended release properties are achieved in accordance with the invention by using the extended release agents as hereinabove described, whereby it is not necessary to add a polymer to the composition, it is possible to include a polymer in the composition for other purposes.
In general, if a polymer is present in the composition, such polymer is present in an amount of less than 5% by weight, generally in an amount less than 2% by weight, and more preferably in an amount less than 1% by weight. In most cases, the composition is free of a polymer in that a polymer is not required to achieve extended release properties.
The composition is preferably used as an oral dosage form; for example, in the form of a tablet or capsule.
The oral dosage form of the present invention which provides for extended release of an erythromycin derivative may also be employed in a liquid oral dosage form, which may include an emulsion, a micro-emulsion, a suspension, syrup, etc.
In general, the pharmaceutical composition of the present invention includes an erythromycin derivative in an amount from about 45% to about 60% by weight, and preferably contains about 50% by weight of the erythromycin derivative. The erythromycin derivative is preferably 6-0-methoxy erythromycin A, known as Clarithromycin.
The composition of the invention is administered to a host in an amount effective to treat a bacterial infection. A daily dose of the composition of the invention is preferably delivered in a single dose and can range from about 500 mg to 1000 mg per day, with the pharmaceutical generally being administered for periods of from 5 to 14 days.
It has been found that it is possible to provide an extended release pharmaceutical composition of an erythromycin derivative, without use of a polymer to provide for extended release, and that such a pharmaceutical composition has properties similar to those of the extended release composition of U.S. 6,010,718.
Although extended release properties are achieved in accordance with the invention by using the extended release agents as hereinabove described, whereby it is not necessary to add a polymer to the composition, it is possible to include a polymer in the composition for other purposes.
In general, if a polymer is present in the composition, such polymer is present in an amount of less than 5% by weight, generally in an amount less than 2% by weight, and more preferably in an amount less than 1% by weight. In most cases, the composition is free of a polymer in that a polymer is not required to achieve extended release properties.
The composition is preferably used as an oral dosage form; for example, in the form of a tablet or capsule.
The oral dosage form of the present invention which provides for extended release of an erythromycin derivative may also be employed in a liquid oral dosage form, which may include an emulsion, a micro-emulsion, a suspension, syrup, etc.
In general, the pharmaceutical composition of the present invention includes an erythromycin derivative in an amount from about 45% to about 60% by weight, and preferably contains about 50% by weight of the erythromycin derivative. The erythromycin derivative is preferably 6-0-methoxy erythromycin A, known as Clarithromycin.
The composition of the invention is administered to a host in an amount effective to treat a bacterial infection. A daily dose of the composition of the invention is preferably delivered in a single dose and can range from about 500 mg to 1000 mg per day, with the pharmaceutical generally being administered for periods of from 5 to 14 days.
It has been found that it is possible to provide an extended release pharmaceutical composition of an erythromycin derivative, without use of a polymer to provide for extended release, and that such a pharmaceutical composition has properties similar to those of the extended release composition of U.S. 6,010,718.
Tn particular, a pharmaceutical composition in accordance with the invention, (similarly to the pharmaceutical composition of U.S. Patent 6,010,718) can induce a statistically significantly lower mean fluctuation index in the plasma than ari immediate release composition while maintaining a similar bio-availability, or providing for increased bio-availability.
The invention will be further described with respect to the following examples;
however, the scope of the invention is not to be limited thereby. Unless otherwise specified, all parts and percentages are by weight.
Ingredient Conc.
Example 1: Clarithromycin 50 Lactose 19 Glyceryl monostearate 30 Magnesium Stearate 1.0 Method A: Melt the glyceryl monostearate and add the clarithromycin. Let cool and then mill through a screen. Blend the mixture with the lactose in a tumble blender for about 20 minutes. Add magnesium stearate and blend for 5 minutes. Compress the blend using a rotary tablet press.
Method B: Granulate lactose, glyceryl monostearate and clarithromycin together using a high shear granulator. Stop granulating when the gylceryl monosterate has completely melted. Screen the granulate. Blend the granulate and magnesium stearate for 5 minutes in a tumble blender. Compress the blend using a rotary tablet press.
Example 2: Clarithromycin 50 Lactose 19 Magnesium Stearate 1 Method A: Melt the ATMUL 84S and add the clarithromycin. Let cool and then mill through a screen. Blend the mixture with the lactose in a tumble blender for about 20 S
minutes. Add magnesium stearate and blend for 5 minutes. Compress the blend using a rotary tablet press.
Example 3: Clarithromycin 50 Lactose 35 Cetyl alcohol 10 Stearic Acid 5 Method A: Granulate lactose, cetyl alcohol and clarithromycin together using a high shear granulator. Stop granulating when the cetyl alcohol has completely melted.
Screen the granulate. Blend the granulate and magnesium stearate for 5 minutes in a tumble blender.
Compress the blend using a rotary tablet press.
Method B: Dissolve the cetyl alcohol in ethanol (95%). Granulate the clarithromycin and lactose with the cetyl alcohol solution. Screen the granulate and then dry.
Blend the dried granulate and stearic acid in a tumble blend for 5 minutes. Compress the blend using a rotary tablet press.
Example 4: Clarithromycin 50 Lactose 34 Kaolin 15 Magnesium Stearate 1 Example 5: Clarithromycin 50 Lactose 30 Starch 3 Kaolin 16 Magnesium Stearate 1 Example 6: Clarithromycin 50 Lactose 25 Starch 3 Cetyl alcohol 17 Stearic Acid 5 Example 7: Clarithromycin 50 Sucrose 25 Starch 3 Cetyl alcohol 17 Stearic Acid 5 Example 8: Clarithromycin 50 Dextrose 34 Kaolin 15 Magnesium Stearate 1 The compositions of Examples 4-8 are formulated in a manner similar to the previous examples.
Numerous modifications and variations of the present invention are possible in light of the above teachings and, therefore, Within the scope of the pending claims, the invention may be practiced otherwise then as particularly described.
The invention will be further described with respect to the following examples;
however, the scope of the invention is not to be limited thereby. Unless otherwise specified, all parts and percentages are by weight.
Ingredient Conc.
Example 1: Clarithromycin 50 Lactose 19 Glyceryl monostearate 30 Magnesium Stearate 1.0 Method A: Melt the glyceryl monostearate and add the clarithromycin. Let cool and then mill through a screen. Blend the mixture with the lactose in a tumble blender for about 20 minutes. Add magnesium stearate and blend for 5 minutes. Compress the blend using a rotary tablet press.
Method B: Granulate lactose, glyceryl monostearate and clarithromycin together using a high shear granulator. Stop granulating when the gylceryl monosterate has completely melted. Screen the granulate. Blend the granulate and magnesium stearate for 5 minutes in a tumble blender. Compress the blend using a rotary tablet press.
Example 2: Clarithromycin 50 Lactose 19 Magnesium Stearate 1 Method A: Melt the ATMUL 84S and add the clarithromycin. Let cool and then mill through a screen. Blend the mixture with the lactose in a tumble blender for about 20 S
minutes. Add magnesium stearate and blend for 5 minutes. Compress the blend using a rotary tablet press.
Example 3: Clarithromycin 50 Lactose 35 Cetyl alcohol 10 Stearic Acid 5 Method A: Granulate lactose, cetyl alcohol and clarithromycin together using a high shear granulator. Stop granulating when the cetyl alcohol has completely melted.
Screen the granulate. Blend the granulate and magnesium stearate for 5 minutes in a tumble blender.
Compress the blend using a rotary tablet press.
Method B: Dissolve the cetyl alcohol in ethanol (95%). Granulate the clarithromycin and lactose with the cetyl alcohol solution. Screen the granulate and then dry.
Blend the dried granulate and stearic acid in a tumble blend for 5 minutes. Compress the blend using a rotary tablet press.
Example 4: Clarithromycin 50 Lactose 34 Kaolin 15 Magnesium Stearate 1 Example 5: Clarithromycin 50 Lactose 30 Starch 3 Kaolin 16 Magnesium Stearate 1 Example 6: Clarithromycin 50 Lactose 25 Starch 3 Cetyl alcohol 17 Stearic Acid 5 Example 7: Clarithromycin 50 Sucrose 25 Starch 3 Cetyl alcohol 17 Stearic Acid 5 Example 8: Clarithromycin 50 Dextrose 34 Kaolin 15 Magnesium Stearate 1 The compositions of Examples 4-8 are formulated in a manner similar to the previous examples.
Numerous modifications and variations of the present invention are possible in light of the above teachings and, therefore, Within the scope of the pending claims, the invention may be practiced otherwise then as particularly described.
Claims (29)
- Claim 1. A pharmaceutical composition for an extended release of a erythromycin derivative in the gastrointestinal environment, comprising:
an erythromycin derivative, and at least one member selected from the group consisting of long chain hydrocarbons, long chain carboxylic acids, long chain carboxylic esters and long chain alcohols, said at least one member being present in an amount effective to provide for extended release of the erythromycin derivative in the composition, said erythromycin derivative in said composition having an extended release profile. - Claim 2. The pharmaceutical composition of claim 1 wherein said pharmaceutical composition is an oral dosage form.
- Claim 3. The pharmaceutical composition of claim 2 wherein said composition contains less than 1% of polymer, by weight.
- Claim 4. The pharmaceutical composition of claim 3 wherein said at least one member is present in an amount of about 1% to about 60% by weight.
- Claim 5. The pharmaceutical composition of claim 3 wherein said at least one member is a long chain carboxylic acid ester.
- Claim 6. The pharmaceutical composition of claim 3 wherein said at least one member is a long chain alcohol.
- Claim 7. The pharmaceutical composition of claim 3 wherein said at least one member is a long chain hydrocarbon.
- Claim 8. The pharmaceutical composition of claim 3 wherein said composition contains less than 3% of polymer, by weight.
- Claim 9. The pharmaceutical composition of claim 3 wherein said composition contains less than 1% by weight of polymer.
- Claim 10. The pharmaceutical composition of claim 4 wherein the erythromycin derivative is 6-0-methoxyerythromycin A.
- Claim 11. The pharmaceutical composition of claim 3 wherein the erythromycin derivative is present in the composition in an amount of from about 45% to 60%
by weight. - Claim 12. The composition of claim 3 wherein said composition provides a dose of the erythromycin derivative of from about 500 milligrams to about 1,000 milligrams.
- Claim 13. A tablet, comprising:
an erythromycin derivative; and at least one member selected from the group consisting of long chain hydrocarbons, long chain carboxylic acids, and long chain alcohols, said at least one member being present in an amount to provide for extended release of the erythromycin derivative, said erythromycin derivative in said tablet having an extended release profile. - Claim 14. The tablet of claim 13 wherein said composition contains less than 3% of polymer, by weight.
- Claim 15. The tablet of claim 14 said at least one member is a long chain carboxylic acid ester.
- Claim 16. The tablet of claim 14 wherein said at least one member is a long chain alcohol.
- Claim 17. The tablet of claim 14 wherein said at least one member is a long chain hydrocarbon.
- Claim 18. The tablet of claim 13 wherein the erythromycin derivative is 6-0-methoxyerythromycin A.
- Claim 19. The tablet of claim 13 wherein the erythromycin derivative is present in the composition in an amount of from about 45% to 60% by weight.
- Claim 20. The tablet of claim 19 wherein said composition provides a dose of the erythromycin derivative of from about 500 milligrams to about 1,000 milligrams.
- Claim 21. A process for treating a host for a bacterial infection, comprising:
treating a host with the composition of claim 1 in an amount effective to treat a bacterial infection. - Claim 22. A process for treating a host for a bacterial infection, comprising:
treating a host with the composition of claim 2 in an amount effective to treat a bacterial infection. - Claim 23. A process for treating a host for a bacterial infection, comprising:
treating a host with the composition of claim 8 in an amount effective to treat a bacterial infection. - Claim 24. A process for treating a host for a bacterial infection, comprising:
treating a host with the composition of claim 13 in an amount effective to treat a bacterial infection. - Claim 25. A process for treating a host for a bacterial infection, comprising:
treating a host with the composition of claim 18 in an amount effective to treat a bacterial infection. - Claim 26. A process for treating a host for a bacterial infection, comprising:
treating a host with the composition of claim 15 in an amount effective to treat a bacterial infection. - Claim 27. A process for treating a host for a bacterial infection, comprising:
treating a host with the composition of claim 16 in an amount effective to treat a bacterial infection. - Claim 28. A process for treating a host for a bacterial infection, comprising:
treating a host with the composition of claim 17 in an amount effective to treat a bacterial infection. - Claim 29. A process for treating a host for a bacterial infection, comprising:
treating a host with the composition of claim 19 in an amount effective to treat a bacterial infection.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68998800A | 2000-10-13 | 2000-10-13 | |
| US09/689,988 | 2000-10-13 | ||
| PCT/US2001/032055 WO2002038577A2 (en) | 2000-10-13 | 2001-10-12 | Extended release erythromycin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2425688A1 true CA2425688A1 (en) | 2002-05-16 |
Family
ID=24770642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002425688A Abandoned CA2425688A1 (en) | 2000-10-13 | 2001-10-12 | Extended release erythromycin derivatives |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1333807A4 (en) |
| JP (1) | JP2004528272A (en) |
| AU (1) | AU2002239232A1 (en) |
| CA (1) | CA2425688A1 (en) |
| MX (1) | MXPA03003146A (en) |
| WO (1) | WO2002038577A2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6544555B2 (en) | 2000-02-24 | 2003-04-08 | Advancis Pharmaceutical Corp. | Antibiotic product, use and formulation thereof |
| US20020068078A1 (en) | 2000-10-13 | 2002-06-06 | Rudnic Edward M. | Antifungal product, use and formulation thereof |
| US8062672B2 (en) | 2003-08-12 | 2011-11-22 | Shionogi Inc. | Antibiotic product, use and formulation thereof |
| WO2006050514A1 (en) | 2004-11-04 | 2006-05-11 | Xenoport, Inc. | Gabapentin prodrug sustained release oral dosage forms |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3108046A (en) * | 1960-11-25 | 1963-10-22 | Smith Kline French Lab | Method of preparing high dosage sustained release tablet and product of this method |
| JPS49107855A (en) * | 1973-02-03 | 1974-10-14 | ||
| JP2528652B2 (en) * | 1987-03-30 | 1996-08-28 | エスエス製薬株式会社 | Long-acting cefradine formulation |
| US4808411A (en) * | 1987-06-05 | 1989-02-28 | Abbott Laboratories | Antibiotic-polymer compositions |
| AU8219191A (en) * | 1990-06-14 | 1992-01-07 | Kalmo Enterprises, Inc. | Stable aqueous drug suspensions |
| JP3265680B2 (en) * | 1992-03-12 | 2002-03-11 | 大正製薬株式会社 | Oral pharmaceutical composition |
| JPH07267850A (en) * | 1994-03-28 | 1995-10-17 | Eisai Co Ltd | Medicine composition prevented in unpleasant taste and method for producing the same |
| EP0826376B1 (en) * | 1995-05-02 | 2007-01-24 | Taisho Pharmaceutical Co. Ltd | Composition for oral administration |
| US5858986A (en) * | 1996-07-29 | 1999-01-12 | Abbott Laboratories | Crystal form I of clarithromycin |
| US6010718A (en) * | 1997-04-11 | 2000-01-04 | Abbott Laboratories | Extended release formulations of erythromycin derivatives |
| US5780604A (en) * | 1997-09-26 | 1998-07-14 | Abbott Laboratories | 11,12-cyclic phosphite or phosphate derivatives of erythromycin and related macrolides |
| JP2000169364A (en) * | 1998-09-30 | 2000-06-20 | Taisho Pharmaceut Co Ltd | Granule for oral pharmaceutical preparation |
| RU2270695C2 (en) * | 1999-03-17 | 2006-02-27 | Дайити Фармасьютикал Ко., Лтд. | Pharmaceutical composition |
| SI20244A (en) * | 1999-05-19 | 2000-12-31 | LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. | Melt granulation |
-
2001
- 2001-10-12 CA CA002425688A patent/CA2425688A1/en not_active Abandoned
- 2001-10-12 MX MXPA03003146A patent/MXPA03003146A/en unknown
- 2001-10-12 JP JP2002541109A patent/JP2004528272A/en active Pending
- 2001-10-12 AU AU2002239232A patent/AU2002239232A1/en not_active Abandoned
- 2001-10-12 EP EP01986972A patent/EP1333807A4/en not_active Withdrawn
- 2001-10-12 WO PCT/US2001/032055 patent/WO2002038577A2/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002038577A2 (en) | 2002-05-16 |
| EP1333807A4 (en) | 2005-06-29 |
| WO2002038577A3 (en) | 2002-09-19 |
| EP1333807A2 (en) | 2003-08-13 |
| MXPA03003146A (en) | 2004-12-06 |
| AU2002239232A1 (en) | 2002-05-21 |
| JP2004528272A (en) | 2004-09-16 |
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