(EP1446103) The present invention provides compositions and methods for extending the release times and lowering the toxicity of pharmacologically active compounds. The compounds comprise a salt of the pharmacologically active compound with a lipophilic counterion and a pharmaceutically acceptable water soluble solvent combined together to form an injectable composition. The lipophilic counterion may be a saturated or unsaturated C8-C22 fatty acid, and preferably may be a saturated or unsaturated C10-C18 fatty acid. When injected into a mammal, at least a portion of the composition precipitates and releases the active compound over time. Thus, the composition forms a slowly releasing drug depot of the active compound in the mammal. Therefore, the present invention enables one to provide a controlled dose administration of the active compound for a periods of up to 15 days or even longer. Many compounds can be administered according to the present invention including, but not limited to, tilmicosin, oxytetracycline, metoprolol, fluoxetine, roxithromycin, and turbinafine.
(EP1446103) 1. A composition for administration of a pharmacologically active compound to a mammal comprising a salt of a basic pharmacologically active compound and a lipophilic acid wherein the lipophilic acid is selected from the group consisting of saturated or unsaturated fatty acids, cholic acids, phospatidic acids, dicarboxylic acids (like sebacic acid), polysebacic acid and polybenzoic acid; and a pharmaceutically acceptable organic solvent, wherein the pharmaceutically acceptable solvent is selected from the group consisting of one or a combination of: pyrrolidone, N-methyl pyrrolidone, polyethylene glycol, propylene glycol, glycerol formal, isosorbide dimethyl ether, ethanol, dimethyl sulfoxide, tetrahydrofurfuryl alcohol, and triacetin; combined together to form an injectable composition, wherein the composition forms a precipitate when the composition is introduced or injected into an aqueous environment and wherein the composition releases the active compound over time when introduced or injected into the aqueous environment. 2. The composition of claim 1 wherein the pharmaceutically acceptable solvent is a water miscible solvent. 3. The composition of claim 1 wherein the pharmacologically active compound is an antibiotic. 4. The composition of claim 1 wherein the pharmacologically active compound is tilmicosin, oxytetracycline, doxycycline, fluoxetine, roxithromycin, turbinafine or metoprolol. 5. The composition of claim 1 wherein the pharmacologically active compound is selected from the group consisting of: trimethoprim, neomycin, streptomycin, gentamycin, dibucaine, bupivacaine, benzocaine, tetracaine, acepromazine, itraconazole, tetracyclines, sulfonamides, and aminoglycosides. 6. The composition of claim 1 wherein the lipophilic acid is a C 10-C 22 saturated or un-saturated fatty acid. 7. The composition of claim 1 wherein the lipophilic acid is a C 10-C 18 saturated or unsaturated fatty acid. 8. The composition of claim 7 wherein the fatty acid is selected from the group consisting of: lauric acid, decanoic acid, myristic acid, oleic acid and linoleic acid. 9. The composition of claim 1 wherein the pharmaceutically acceptable solvent comprises 10% propylene glycol in glycerol formal with or without stabilizers. 10. The composition of claim 1 wherein the pharmaceutically acceptable solvent is triacetin. 11. The composition of claim 1 wherein the pharmacologically active compound is oxytetracycline, the lipophilic acid is lauric acid, and the pharmaceutically acceptable solvent is selected from the group consisting of one or more of polyethylene glycol, propylene glycol, and glycerol formal. 12. The composition of claim 1 wherein the pharmacologically active compound is tilmicosin, the lipophilic acid is lauric acid, and the pharmaceutically acceptable solvent is selected from the group consisting of one or more of polyethylene glycol, propylene glycol, and glycerol formal. 13. A pharmacologically active composition comprising a salt of a basic pharmacologically active compound and a lipophilic acid, selected from the group consisting of saturated or unsaturated fatty acids, cholic acids, phosphatidic acids, and dicarboxylic acids; and a pharmaceutically acceptable organic solvent wherein the pharmaceutically acceptable solvent is selected from the group consisting of one or a combination of: pyrrolidone, N-methyl pyrrolidone, polyethylene glycol, propylene glycol, glycerol formal, isosorbide dimethyl ether, ethanol, dimethyl sulfoxide, tetrahydrofurfuryl alcohol, and triacetin; combined together to form an injectable composition for use in treating a condition in a mammal that is responsive to the pharmacologically active compound; wherein the composition forms a precipitate and releases the active compound over time when injected into the mammal. 14. The pharmacologically active composition for use of claim 13 wherein the pharmaceutically acceptable solvent is a water miscible solvent. 15. The pharmacologically active composition for use of claim 13 wherein the pharmacologically active compound is an antibiotic. 16. The pharmacologically active composition for use of claim 15 wherein the antibiotic is tilmicosin, tetracycline, or doxycycline. 17. The pharmacologically active composition for use of claim 15 wherein the antibiotic is selected from the group consisting of: trimethoprim, neomycin, streptomycin, gentamycin, tetracyclines, sulfonamides, and aminoglycosides. 18. The pharmacologically active composition for use of claim 13 wherein the lipophilic counterion is a fatty acid. 19. The pharmacologically active composition for use of claim 18 wherein the fatty acid is a C 10-C 22 fatty acid. 20. The pharmacologically active composition of for use claim 19 wherein the fatty acid is selected from the group consisting of: lauric acid, decanoic acid, myristic acid, oleic acid and linoleic acid. 21. The pharmacologically active composition for use of claim 13 wherein the lipophilic counterion is sebacic acid. 22. The pharmacologically active composition for use of claim 13 wherein the pharmaceutically acceptable carrier is triacetin. 23. The pharmacologically active composition for use of claim 13 wherein the pharmacologically active compound is oxytetracycline, the lipophilic counterion is lauric acid, and the pharmaceutically acceptable solvent is selected from the group consisting of one or more of polyethylene glycol, propylene glycol, and glycerol formal. 24. The pharmacologically active composition for use of claim 13 wherein pharmacologically active compound is tilmicosin, the lipophilic counterion is decanoic acid, and the pharmaceutically acceptable solvent is selected from the group consisting of one or more of polyethylene glycol, propylene glycol, and glycerol formal. 25. A method of manufacturing an injectable formulation for the administration of a pharmacologically active compound to a mammal comprising: providing a salt of a basic pharmacologically active compound and a lipophilic acid wherein the lipophilic acid is selected from the group consisting of saturated or unsaturated fatty acids, cholic acids, phospatidic acids, and dicarboxylic acids; and providing a pharmaceutically acceptable organic solvent wherein the pharmaceutically acceptable solvent is selected from the group consisting of one or a combination of: pyrrolidone, N-methyl pyrrolidone, polyethylene glycol, propylene glycol, glycerol formal, isosorbide dimethyl ether, ethanol, dimethyl sulfoxide, tetrahydrofurfuryl alcohol, and triacetin; combining together the salt and the pharmacologically acceptable organic solvent to provide an injectable composition, wherein the composition forms a precipitate when the composition is introduced or injected into an aqueous environment and wherein the composition releases the active compound over time when introduced or injected into the aqueous environment. 26. The method of claim 25 wherein the pharmaceutically acceptable solvent is a water miscible solvent. 27. The method of claim 25 wherein the pharmacologically active compound is an antibiotic. 28. The method of claim 27 wherein the antibiotic is tilmicosin, tetracycline, or doxycycline. 29. The method of claim 27 wherein the antibiotic is selected from the group consisting of: trimethoprim, neomycin, streptomycin, gentamycin, tetracyclines, sulfonamides, and aminoglycosides. 30. The method of claim 25 wherein the lipophilic acid is a C 8-C 22 fatty acid. 31. The method of claim 30 wherein the fatty acid is a C 10-C 22 fatty acid. 32. The method of claim 31 wherein the fatty acid is selected from the group consisting of: lauric acid, decanoic acid, myristic acid, oleic acid and linoleic acid. 33. The method of claim 25 wherein the lipophilic acid is sebacic acid. 34. The method of claim 25 wherein the pharmaceutically acceptable carrier is triacetin. 35. The method of claim 25 wherein the pharmacologically active compound is oxytetracycline, the lipophilic acid is lauric acid, and the pharmaceutically acceptable solvent is selected from the group consisting of one or more of polyethylene glycol, propylene glycol, and glycerol formal. 36. The method of claim 25 wherein the pharmacologically active compound is tilmicosin, the lipophilic acid is decanoic acid, and the pharmaceutically acceptable solvent is selected from the group consisting of one or more of polyethylene glycol, propylene glycol, and glycerol formal. 37. The method of claim 30 wherein the fatty acid is a C 10-C 18 fatty acid.
(EP1446103) LEGAL DETAILS FOR EP1446103 Actual or expected expiration date=2022-10-18 Legal state=ALIVE Status=GRANTED Event publication date=2002-10-18 Event code=EP/APP Event indicator=Pos Event type=Examination events Application details Application country=EP EP02802160 Application date=2002-10-18 Standardized application number=2002EP-0802160 Event publication date=2004-08-18 Event code=EP/A2 Event type=Examination events Application published without search report Publication country=EP Publication number=EP1446103 Publication stage Code=A2 Publication date=2004-08-18 Standardized publication number=EP1446103 Event publication date=2004-08-18 Event code=EP/17P Event indicator=Pos Event type=Examination events Request for examination filed Pruefungsantrag gestellt Effective date of the event=2004-05-18 Event publication date=2004-08-18 Event code=EP/AK Event indicator=Pos Event type=Designated states Designated contracting states: Benannte vertragsstaaten AT BE BG CH CY CZ DE DK 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