US3945993A
Expired / Lapsed
US
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Derivatives of polyene macrolide antibiotics
Assignee: PRINTEK CORP 33 EGLANTINE AVE PENNINGTON NJ 08534 A CORP OF DE
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Filing: 1971-06-07
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Granted: 1976-03-23
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Expires: 1991-06-07
Abstract
Abstract Derivatives of amphoteric polyene macrolide antibiotics which carry, on the lactone ring, a carboxyl group and an amino sugar characterized by a primary amine group, consist of (a) the methyl, ethyl or propyl ester formed by esterification of the carboxyl group, and (b) salts of such polyene esters constituted as acid addition salts formed with the amine group. The derivatives (a) and (b) have effective antimicrobial activity, e.g. antifungal potency, comparable to the base antibiotics, and the acid salts (b), produced by suitable acids, e.g. hydrochlorides, can be made to have good water solubility which is normally unattainable with the base compounds and is of special advantage in a compound which retains strong activity. Other addition salts are also of value, for example to provide lipid-soluble forms of these antifungal polyenes. Esterification of these chemically sensitive antibiotics is unusually successful using diazomethane, diazoethane or diazopropane with tetrahydrofurane as solvent to produce the ester dissolved therein, avoiding degradation of the base antibiotic or of its potency.
Inventors
- 👤 Carl P. Schaffner
- 👤 Witold Mechlinski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 05:17
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08; C07C; C07C245/00; C07C245/12; C07C245/14; C07C245/16
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
5 words
Amphotericin B methyl ester hydrochloride.
Claim 2
Dependent Claim
5 words
Amphotericin B methyl ester hydrochloride.
Claim 3
Dependent Claim
4 words
Candicidin methyl ester hydrochloride.
Claim 4
Dependent Claim
4 words
Candicidin methyl ester hydrochloride.
Claim 5
Dependent Claim
4 words
Trichomycin methyl ester hydrochloride.
Claim 6
Dependent Claim
4 words
Trichomycin methyl ester hydrochloride.
Claim 7
Dependent Claim
4 words
Mediocidin methyl ester hydrochloride.
Claim 8
Dependent Claim
4 words
Mediocidin methyl ester hydrochloride.
Claim 9
Dependent Claim
4 words
Pimaricin methyl ester hydrochloride.
Claim 10
Dependent Claim
4 words
Pimaricin methyl ester hydrochloride.
Claim 11
Dependent Claim
23 words
An antimicrobially active product of the group consisting of the methyl, ethyl and propyl esters of amphotericin B and their acid addition salts.
Claim 12
Dependent Claim
23 words
An antimicrobially active product of the group consisting of the methyl, ethyl and propyl esters of amphotericin B and their acid addition salts.
Claim 13
Dependent Claim
22 words
An antimicrobially active product of the group consisting of the methyl, ethyl and propyl esters of candicidin and their acid addition salts.
Claim 14
Dependent Claim
22 words
An antimicrobially active product of the group consisting of the methyl, ethyl and propyl esters of candicidin and their acid addition salts.
Claim 15
Dependent Claim
22 words
An antimicrobially active product of the group consisting of the methyl, ethyl and propyl esters of trichomycin and their acid addition salts.
Claim 16
Dependent Claim
22 words
An antimicrobially active product of the group consisting of the methyl, ethyl and propyl esters of trichomycin and their acid addition salts.
Claim 17
Dependent Claim
22 words
An antimicrobially active product of the group consisting of the methyl, ethyl and propyl esters of mediocidin and their acid addition salts.
Claim 18
Dependent Claim
22 words
An antimicrobially active product of the group consisting of the methyl, ethyl and propyl esters of mediocidin and their acid addition salts.
Claim 19
Dependent Claim
22 words
An antimicrobially active product of the group consisting of the methyl, ethyl and propyl esters of pimaricin and their acid addition salts.
Claim 20
Dependent Claim
22 words
An antimicrobially active product of the group consisting of the methyl, ethyl and propyl esters of pimaricin and their acid addition salts.
Claim 21
Dependent Claim
111 words
An antimicrobially active, polyene macrolide antibiotic product which is selected from the class consisting of: A. alkyl esters, wherein the alkyl group has one to three carbon atoms, of an amphoteric, polyene, macrolide antibiotic a. which has a macrolide ring including an uninterrupted series of 4 to 7 conjugated double bonds and b. which has substituents on said ring that are respectively a carboxyl group, and an amino glycoside moiety in which the amino group is primary (--NH 2 ) and which has the composition --(C 6 H 12 O 4 N); c. said carboxyl group being esterified to constitute said alkyl ester; and B. acid addition salts of said esters.
Claim 22
Dependent Claim
111 words
An antimicrobially active, polyene macrolide antibiotic product which is selected from the class consisting of: A. alkyl esters, wherein the alkyl group has one to three carbon atoms, of an amphoteric, polyene, macrolide antibiotic a. which has a macrolide ring including an uninterrupted series of 4 to 7 conjugated double bonds and b. which has substituents on said ring that are respectively a carboxyl group, and an amino glycoside moiety in which the amino group is primary (--NH 2 ) and which has the composition --(C 6 H 12 O 4 N); c. said carboxyl group being esterified to constitute said alkyl ester; and B. acid addition salts of said esters.
Claim 23
Dependent Claim
22 words
A polyene antibiotic product as defined in claim 11, which is an alkyl ester as recited in section (A) of said claim.
Claim 24
Dependent Claim
17 words
A polyene antibiotic product as defined in claim 11, in which the said alkyl group is methyl.
Claim 25
Dependent Claim
23 words
A polyene antibiotic product as defined in claim 11, which is an acid addition salt as defined in section (B) of said claim.
Claim 26
Dependent Claim
24 words
A polyene antibiotic product as defined in claim 14, which is a water-soluble acid addition salt, and in which the alkyl group is methyl.
Claim 27
Dependent Claim
26 words
An antimicrobially active product selected from the group consisting of the methyl, ethyl and propyl esters of the antibiotics amphotericin B, candicidin, trichomycin, mediocidin and pimaricin.
Claim 28
Dependent Claim
26 words
An antimicrobially active product selected from the group consisting of the methyl, ethyl and propyl esters of the antibiotics amphotericin B, candicidin, trichomycin, mediocidin and pimaricin.
Claim 29
Dependent Claim
36 words
An antimicrobially active product which is a water-soluble acid addition salt of a compound selected from the group consisting of the methyl, ethyl and propyl esters of the antibiotics amphotericin B, candicidin, trichomycin, mediocidin and pimaricin.
Claim 30
Dependent Claim
36 words
An antimicrobially active product which is a water-soluble acid addition salt of a compound selected from the group consisting of the methyl, ethyl and propyl esters of the antibiotics amphotericin B, candicidin, trichomycin, mediocidin and pimaricin.
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) | 1979-03-23 | 1979-09-22 | 1980-03-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-23 | 1983-09-22 | 1984-03-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-23 | 1987-09-22 | 1988-03-23 | $7700.00 | Window Closed / Lapsed |