US4144328A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N,N,N-Trimethyl derivatives of polyene amphoteric antibiotics, process of producing same and pharmaceutical composition
Assignee: Individual
•
Filing: 1977-02-28
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Granted: 1979-03-13
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Expires: 1997-02-28
Abstract
Abstract The present invention relates to novel substances; namely, to N,N,N-trimethyl derivatives of polyene amphoteric antibiotics, and to a process of producing same, said substances having the following general formula: ##STR1## wherein R is aglycone of a polyene amphoteric antibiotic, without the carboxyl group. The process of producing N,N,N-trimethyl derivatives of polyene amphoteric antibiotics is carried out in an organic solvent medium wherein said polyene amphoteric antibiotics are subjected to complete amino-group methylation by means of a methylating agent with subsequent separation of the end product. N,N,N-trimethyl derivatives of polyene amphoteric antibiotics possess high antibiotic activity thus inhibiting the growth of yeast, yeast-like microorganisms, and filamentous fungi. Said compounds are used in medicine to treat fungal diseases.
Inventors
- 👤 Viktor A. Vainshtein
- 👤 Valter O. Kulbakh
- 👤 Evgeny D. Etingov
- 👤 Grigory N. Naumchik
- 👤 Oleg N. Ekzemplyarov
- 👤 Georgy A. Mikhailets
- 👤 Grigory E. Grinberg
- 👤 Alla N. Egorenkova
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 13:15
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
42 words
N,N,N-trimethyl derivatives of a fungicidal non-aromatic polyene macrolide antibiotic selected from the group consisting of amphotericyn B, mycoheptin, and nystatin heptaenes and tetraenes of the formula: ##STR6## wherein R is aglycone of a fungicidal non-aromatic polyene macrolide antibiotic without the carboxyl group.
Claim 2
Dependent Claim
42 words
N,N,N-trimethyl derivatives of a fungicidal non-aromatic polyene macrolide antibiotic selected from the group consisting of amphotericyn B, mycoheptin, and nystatin heptaenes and tetraenes of the formula: ##STR6## wherein R is aglycone of a fungicidal non-aromatic polyene macrolide antibiotic without the carboxyl group.
Claim 3
Dependent Claim
14 words
N,N,N-trimethyl amphotericyn B as the composition of claim 1, having the following formula: ##STR7##
Claim 4
Dependent Claim
13 words
N,N,N-trimethyl mycoheptin as the composition of claim 1 having the following formula: ##STR8##
Claim 5
Dependent Claim
13 words
N,N,N-trimethyl nystatin as the composition of claim 1 having the following formula: ##STR9##
Claim 6
Dependent Claim
97 words
A process for preparing N,N,N-trimethyl derivatives of fungicidal non-aromatic polyene macrolide antibiotics selected from the group consisting of amphotericyn B, mycoheptin, and nystatin heptaenes and tetraenes having the formula: ##STR10## wherein R is aglycone of a fungicidal non-aromatic polyene macrolide antibiotic without the carboxyl group, comprising subjecting said polyene antibiotic macrolide to exhaustive amino sugar-mycosamine methylation in a medium of an organic solvent with a methylating agent selected from the group consisting of methyl halides, methyl sulfates, or methyl esters of organic sulfonic acids; in the presence of sodium bicarbonate followed by isolation of the desired product.
Claim 7
Dependent Claim
97 words
A process for preparing N,N,N-trimethyl derivatives of fungicidal non-aromatic polyene macrolide antibiotics selected from the group consisting of amphotericyn B, mycoheptin, and nystatin heptaenes and tetraenes having the formula: ##STR10## wherein R is aglycone of a fungicidal non-aromatic polyene macrolide antibiotic without the carboxyl group, comprising subjecting said polyene antibiotic macrolide to exhaustive amino sugar-mycosamine methylation in a medium of an organic solvent with a methylating agent selected from the group consisting of methyl halides, methyl sulfates, or methyl esters of organic sulfonic acids; in the presence of sodium bicarbonate followed by isolation of the desired product.
Claim 8
Dependent Claim
27 words
The process of claim 5, wherein the methylating agent is selected from the group consisting of methyl iodide, dimethyl sulfate, and methyl esters of toluene sulfonic acids.
Claim 9
Dependent Claim
19 words
The process of claim 5, wherein the organic solvent is selected from the group consisting of dimethylsulfoxide and dimethylformamide.
Claim 10
Dependent Claim
30 words
The process of claim 5, wherein the amount of sodium bicarbonate varies from 0.5 to 2.5 parts by weight per part by weight of the fungicidal non-aromatic polyene macrolide antibiotic.
Claim 11
Dependent Claim
20 words
The process of claim 5, wherein the methylation reaction is conducted at a temperature varying from 25 to 45° C.
Claim 12
Dependent Claim
57 words
A medicinal composition comprising as an active ingredient, N,N,N-trimethyl derivatives of a fungicidal non-aromatic polyene macrolide antibiotic selected from the group consisting of amphotericyn B, mycoheptin, and nystatin, heptaenes and tetraenes of the formula: ##STR11## wherein R is aglycone of a fungicidal non-aromatic polyene macrolide antibiotic without the carboxyl group, in combination with a pharmaceutically acceptable carrier.
Claim 13
Dependent Claim
57 words
A medicinal composition comprising as an active ingredient, N,N,N-trimethyl derivatives of a fungicidal non-aromatic polyene macrolide antibiotic selected from the group consisting of amphotericyn B, mycoheptin, and nystatin, heptaenes and tetraenes of the formula: ##STR11## wherein R is aglycone of a fungicidal non-aromatic polyene macrolide antibiotic without the carboxyl group, in combination with a pharmaceutically acceptable carrier.
References Cited (Backward Citations)
US3945993A
Cited
US4002741A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-03-12 | 1982-09-11 | 1983-03-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-03-12 | 1986-09-11 | 1987-03-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-03-12 | 1990-09-11 | 1991-03-13 | $7700.00 | Window Closed / Lapsed |