WO1996019489A1 - Composes - Google Patents
Composes Download PDFInfo
- Publication number
- WO1996019489A1 WO1996019489A1 PCT/IE1995/000065 IE9500065W WO9619489A1 WO 1996019489 A1 WO1996019489 A1 WO 1996019489A1 IE 9500065 W IE9500065 W IE 9500065W WO 9619489 A1 WO9619489 A1 WO 9619489A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- roxithromycin
- clarithromycin
- azithromycin
- acetylcystein
- compound
- Prior art date
Links
Classifications
-
- 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
-
- 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
Definitions
- the present invention relates to new antibiotic and mucolytic salts of roxithromycin, clarithromycin and azithromcyin.
- the invention is directed towards providing antibiotic and mucolytic salts.
- R is a radical selected from :
- Clarithromycin has the structure
- Azithromycin has the structure
- the compounds according to the invention are white microcrystalline powders .
- compositions will typically contain suitable excipients and/or vehicles which are conventionally used in galenical pharmacy.
- the method for the preparation of the new salts comprises reacting roxithromycin, clarithromycin or azithromycin base with N-acetylcystein in a stoichiometrical ratio or preferably with a slight excess of the antibiotic nucleus. Most preferably the reaction is carried out in an organic solvent, at a temperature of between 20 and 40°C and in the presence of water, preferably in an amount of not greater than 20%.
- the reactions may be carried out in a suspension of water at a temperature of 20 and 40°C, (with N-acetylcystein in a stoichiometrical ratio or in the presence of a slight excess of the antibiotic nucleus), and after building the salts, water is distilled off under very mild conditions (low vacuum, low temperature) .
- test organism was maintained through periodic inoculations on agar slants containing USP 23 Medium No. 1. The slants are incubated at 32-35°C for 24 hours, and stored under refrigeration.
- Assay plates Sterile plastic petri-dishes (ca. 20 x 100mm) with covers were used as assay plates. Assay cylinders were manufactured from stainless steel (o.d. 8mm ⁇ 0.1mm, i.d. 6mm + 0.1mm, length 10mm ⁇ 0.1mm).
- Buffer Solution No. 3 fUSP 23. (0.1M potassium phosphate buffer pH 8.0) Dibasic potassium phosphate 16.73g Monobasic potassium phosphate 0.523g Purified Water 1000ml
- Test Sample (Roxithromycin Stinoprate):
- Stinoprate test substance was compared to the standard curve obtained for the Erythromycin Stinoprate standard dilutions. This was calculated as a percentage of the potency of the 1.0 ⁇ g/ml Erythromycin Stinoprate standard dilution.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
L'invention porte sur des sels de roxithromycine, de clarithromycine et d'azithromycine, agissant comme antibiotique et fluidifiant. Elle porte notamment sur le stinoprate de roxithromycine qui s'avère plus actif que le stinoprate d'érythromycine.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU43993/96A AU4399396A (en) | 1994-12-19 | 1995-12-19 | Compounds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IE940973 | 1994-12-19 | ||
IE940973 | 1994-12-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996019489A1 true WO1996019489A1 (fr) | 1996-06-27 |
Family
ID=11040597
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IE1995/000065 WO1996019489A1 (fr) | 1994-12-19 | 1995-12-19 | Composes |
Country Status (2)
Country | Link |
---|---|
AU (1) | AU4399396A (fr) |
WO (1) | WO1996019489A1 (fr) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998005674A1 (fr) * | 1996-08-07 | 1998-02-12 | Russinsky Limited | Procede pour la production de sels d'erythromycine, de roxithromycine, de clarithromycine et d'azithromycine |
EP0925789A1 (fr) * | 1997-12-02 | 1999-06-30 | Pfizer Products Inc. | Composition topique contenant de l'azithromycine pour le traitement d'infections oculaires |
WO2000023081A1 (fr) * | 1998-10-20 | 2000-04-27 | Lauteral Limited | Derives d'erythromycine, de clarithromycine, de roxithromycine ou d'azithromycine ayant une activite antibiotique et mucolytique |
US6569443B1 (en) | 1999-03-31 | 2003-05-27 | Insite Vision, Inc. | Topical treatment or prevention of ocular infections |
EP1446010A2 (fr) * | 2001-10-18 | 2004-08-18 | Teva Pharmaceutical Industries Ltd. | Compositions d'azithromycine stabilisees |
US6861411B1 (en) | 1997-12-02 | 2005-03-01 | Pfizer, Inc. | Method of treating eye infections with azithromycin |
US7056893B2 (en) | 1999-03-31 | 2006-06-06 | Insite Vision, Inc. | Topical treatment for prevention of ocular infections |
US7723389B2 (en) * | 2001-03-30 | 2010-05-25 | The Board Of Trustees Of The Leland Stanford Junior University | N-acetylcysteine compositions and methods for the treatment and prevention of drug toxicity |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0057489A1 (fr) * | 1981-02-02 | 1982-08-11 | REFARMED, Recherches Pharmaceutiques et Médicales S.A. | Dérivés d'érythromycine contenant du soufre ayant une activité thérapeutique, procédé pour leur préparation et compositions pharmaceutiques les contenant |
FR2534588A2 (fr) * | 1982-10-15 | 1984-04-20 | Roussel Uclaf | Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments |
-
1995
- 1995-12-19 AU AU43993/96A patent/AU4399396A/en not_active Abandoned
- 1995-12-19 WO PCT/IE1995/000065 patent/WO1996019489A1/fr active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0057489A1 (fr) * | 1981-02-02 | 1982-08-11 | REFARMED, Recherches Pharmaceutiques et Médicales S.A. | Dérivés d'érythromycine contenant du soufre ayant une activité thérapeutique, procédé pour leur préparation et compositions pharmaceutiques les contenant |
FR2534588A2 (fr) * | 1982-10-15 | 1984-04-20 | Roussel Uclaf | Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments |
Non-Patent Citations (4)
Title |
---|
M. DE BERNARDI ET AL.: "Human pharmacokinetics of erythryomycin propionate-N-acetylcysteinate", INT. J. CLIN. PHARMACOL. THER. TOXICOL., vol. 26, 1988, pages 444 - 7, XP002002013 * |
M.F. PARRY AND H. NEU: "Effect of N-Acetylcysteine on Antibiotic Activity and Bacterial Growth In Vitro", J. CLIN. MICROBIOL., vol. 5, 1977, pages 58 - 61, XP002002481 * |
N. BAHAL AND M.C. NAHATA: "The new macrolide antibiotics: azithromycin, clarithromycin, dirithromycin and roxithromycin", ANNAL. PHARMACOTHER., vol. 26, 1992, pages 46 - 55, XP002002015 * |
O. PAULSEN ET AL.: "No effect of oral N-acetylcysteine on the bioavailability of erythromycin and bacampicillin", EUR. J. RESPIR., vol. 1, 1988, pages 171 - 5, XP002002014 * |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998005674A1 (fr) * | 1996-08-07 | 1998-02-12 | Russinsky Limited | Procede pour la production de sels d'erythromycine, de roxithromycine, de clarithromycine et d'azithromycine |
EP0925789A1 (fr) * | 1997-12-02 | 1999-06-30 | Pfizer Products Inc. | Composition topique contenant de l'azithromycine pour le traitement d'infections oculaires |
US6861411B1 (en) | 1997-12-02 | 2005-03-01 | Pfizer, Inc. | Method of treating eye infections with azithromycin |
WO2000023081A1 (fr) * | 1998-10-20 | 2000-04-27 | Lauteral Limited | Derives d'erythromycine, de clarithromycine, de roxithromycine ou d'azithromycine ayant une activite antibiotique et mucolytique |
AU760884B2 (en) * | 1998-10-20 | 2003-05-22 | Russinsky Limited | Derivatives of erythromycin, clarithromycin, roxithromycin or azithromycin with antibiotic and mucolytic activity |
US6599885B2 (en) | 1998-10-20 | 2003-07-29 | Russinsky Limited | Derivatives of erythromycin, clarithromycin, roxithromycin or azithromycin with antibiotic and mucolytic activity |
US7732415B2 (en) | 1999-03-31 | 2010-06-08 | Insite Vision Incorporated | Topical treatment or prevention of ocular infections |
US6569443B1 (en) | 1999-03-31 | 2003-05-27 | Insite Vision, Inc. | Topical treatment or prevention of ocular infections |
US7056893B2 (en) | 1999-03-31 | 2006-06-06 | Insite Vision, Inc. | Topical treatment for prevention of ocular infections |
US7749970B2 (en) | 1999-03-31 | 2010-07-06 | Insite Vision Incorporated | Topical treatment of prevention of ocular infections |
US7723389B2 (en) * | 2001-03-30 | 2010-05-25 | The Board Of Trustees Of The Leland Stanford Junior University | N-acetylcysteine compositions and methods for the treatment and prevention of drug toxicity |
EP1446010A2 (fr) * | 2001-10-18 | 2004-08-18 | Teva Pharmaceutical Industries Ltd. | Compositions d'azithromycine stabilisees |
EP1446010A4 (fr) * | 2001-10-18 | 2007-06-13 | Teva Pharma | Compositions d'azithromycine stabilisees |
Also Published As
Publication number | Publication date |
---|---|
AU4399396A (en) | 1996-07-10 |
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