US4294958A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Water-soluble salts of trimethylammonium derivatives of polyene macrolide antibiotics and the preparation thereof
Assignee: Gdańsk University of Technology
•
Filing: 1979-07-25
•
Granted: 1981-10-13
•
Expires: 1999-07-25
Abstract
Abstract Inorganic salts of trimethylammonium derivatives of polyene macrolides, particularly the inorganic salts of methyl esters of these derivatives having the general formula: <IMAGE> wherein R is the residue of a polyene macrolide and X is an anion of a salt selected from the group consisting of methylsulphate, sulphate, chloride, phosphate and acetate. The preparation of salts of formula (I) or formula (II) is also disclosed.
Inventors
- 👤 Leonard Falkowski
- 👤 Barbara Stefanska
- 👤 Jan Zielinski
- 👤 Elzbieta Troka
- 👤 Jerzy Golik
- 👤 Pawel Kolodziejczyk
- 👤 Andrzej Jarzebski
- 👤 Emilia Cybulska
- 👤 Edward Borowski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 07:22
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08; A; A61; A61P; A61P31/00; A61P31/04
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
66 words
An antibiotically-active water-soluble salt of a trimethylammonium derivative of a polyene macrolide having the general formula: ##STR4## wherein R is the residue of a polyene macrolide selected from the group consisting of nystatin, polyfungin, amphotericin B, candicidin, pimaricin, trichomycin, levorin, rimocidin, candidin, aureofacin, perimycin and mycoheptin, and X is an anion of a salt selected from the group consisting of methylsulphate, sulphate, chloride, phosphate and acetate.
Claim 2
Dependent Claim
66 words
An antibiotically-active water-soluble salt of a trimethylammonium derivative of a polyene macrolide having the general formula: ##STR4## wherein R is the residue of a polyene macrolide selected from the group consisting of nystatin, polyfungin, amphotericin B, candicidin, pimaricin, trichomycin, levorin, rimocidin, candidin, aureofacin, perimycin and mycoheptin, and X is an anion of a salt selected from the group consisting of methylsulphate, sulphate, chloride, phosphate and acetate.
Claim 3
Dependent Claim
170 words
A process for the preparation of an antibiotically-active water soluble-salt of a trimethylammonium derivative of a polyene macrolide having the general formula: ##STR5## wherein R is the residue of a polyene macrolide selected from the group consisting of nystatin, polyfungin, amphotericin B, candicidin, pimaricin, trichomycin, levorin, rimocidin, candidin, auerofacin, perimycin and mycoheptin, and X is an anion of a salt selected from the group consisting of methylsulphate, sulphate, chloride, phosphate and acetate, which comprises reacting a solution of the polyene macrolide in an organic solvent with dimethylsulphate in the presence of a neutralizing agent at room temperature with continuous stirring until the reaction is substantially complete, precipitating the resulting methylsulphate of N,N,N-trimethyl polyene macrolide methyl ester of formula (I) or methylsulphate of N,N,N-trimethyl polyene macrolide of formula (II) by the addition of ethyl ether, dissolving the precipitate in butanol, washing the organic solvent with water and concentrating under reduced pressure the resulting solution of the desired product of formula (I) or (II) in the form of the methylsulphate salt thereof.
Claim 4
Dependent Claim
170 words
A process for the preparation of an antibiotically-active water soluble-salt of a trimethylammonium derivative of a polyene macrolide having the general formula: ##STR5## wherein R is the residue of a polyene macrolide selected from the group consisting of nystatin, polyfungin, amphotericin B, candicidin, pimaricin, trichomycin, levorin, rimocidin, candidin, auerofacin, perimycin and mycoheptin, and X is an anion of a salt selected from the group consisting of methylsulphate, sulphate, chloride, phosphate and acetate, which comprises reacting a solution of the polyene macrolide in an organic solvent with dimethylsulphate in the presence of a neutralizing agent at room temperature with continuous stirring until the reaction is substantially complete, precipitating the resulting methylsulphate of N,N,N-trimethyl polyene macrolide methyl ester of formula (I) or methylsulphate of N,N,N-trimethyl polyene macrolide of formula (II) by the addition of ethyl ether, dissolving the precipitate in butanol, washing the organic solvent with water and concentrating under reduced pressure the resulting solution of the desired product of formula (I) or (II) in the form of the methylsulphate salt thereof.
Claim 5
Dependent Claim
25 words
A process according to claim 2, in which the organic solvent is dimethylacetamide, dimethylformamide, dimethylsulphoxide or an aliphatic alcohol containing 1 to 5 carbon atoms.
Claim 6
Dependent Claim
15 words
A process according to claim 2, in which the neutralizing agent is sodium hydrogen carbonate.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-10-12 | 1985-04-13 | 1985-10-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-12 | 1989-04-13 | 1989-10-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-12 | 1993-04-13 | 1993-10-13 | $7700.00 | Window Closed / Lapsed |