US3997533A
Expired / Lapsed
US
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Process for the preparation of 7-acylamino-desacetoxycephalosporanic derivatives
Assignee: Bayer AG
•
Filing: 1974-02-14
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Granted: 1976-12-14
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Expires: 1994-02-14
Abstract
Abstract 7-Acylaminodesacetoxycephalosporanic acid derivatives are produced by heating a penicillin ester S-oxide to a temperature between 60° C and 150° C in the presence of a heavy metal salt.
Inventors
- 👤 Hans-Joachim Kabbe
- 👤 Uwe Petersen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 20:22
CPC Classifications
C; C07; C07D; C07D499/00; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D501/00
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
66 words
In the process for the preparation of a 7-acylamido-3-methylceph-3-em-4-carboxylate by heating the corresponding 6-acylamidopenicillanate sulfoxide at temperatures of from 60° to 150° C in an organic solvent with removal of the water formed, the improvement which comprises conducting the heating in the presence of from 1 to 20 mol percent, based on the sulfoxide present, of a heavy metal sulfonate of the formula: Me(R"SO.sub.3).sub.n in which
Claim 2
Dependent Claim
66 words
In the process for the preparation of a 7-acylamido-3-methylceph-3-em-4-carboxylate by heating the corresponding 6-acylamidopenicillanate sulfoxide at temperatures of from 60° to 150° C in an organic solvent with removal of the water formed, the improvement which comprises conducting the heating in the presence of from 1 to 20 mol percent, based on the sulfoxide present, of a heavy metal sulfonate of the formula: Me(R"SO.sub.3).sub.n in which
Claim 3
Dependent Claim
33 words
Me is a cation having a valence of 1 to 3 and selected from the group consisting of the copper, silver, gold, zinc, cadmium, mercury thallium, tin, lead, iron, cobalt and nickel cations;
Claim 4
Dependent Claim
33 words
Me is a cation having a valence of 1 to 3 and selected from the group consisting of the copper, silver, gold, zinc, cadmium, mercury thallium, tin, lead, iron, cobalt and nickel cations;
Claim 5
Dependent Claim
38 words
R" is alkyl of 1 to 4 carbon atoms, fluoroalkyl of 1 to 4 carbon atoms, phenyl, naphthyl or phenyl or naphthyl substituted by at least one substituent selected from the group consisting of methyl and halo; and
Claim 6
Dependent Claim
38 words
R" is alkyl of 1 to 4 carbon atoms, fluoroalkyl of 1 to 4 carbon atoms, phenyl, naphthyl or phenyl or naphthyl substituted by at least one substituent selected from the group consisting of methyl and halo; and
Claim 7
Dependent Claim
15 words
n has a value of 1 to 3 and corresponds to the valence of Me.
Claim 8
Dependent Claim
15 words
n has a value of 1 to 3 and corresponds to the valence of Me.
Claim 9
Dependent Claim
18 words
The process according to claim 1 wherein Me is an anion of copper, tin, silver, mercury or thallium.
Claim 10
Dependent Claim
19 words
The process according to claim 1 wherein 3 to 10 mol percent of the heavy metal sulfonates are present.
Claim 11
Dependent Claim
16 words
The process according to claim 1 wherein the temperatures are from 80° C to 130° C.
Claim 12
Dependent Claim
19 words
The process according to claim 1 wherein the heating is conducted from about 10 minutes to about 5 hours.
Claim 13
Dependent Claim
16 words
The process according to claim 1 wherein the solvent comprises two organic solvents of differing polarities.
Claim 14
Dependent Claim
13 words
The process according to claim 1 wherein 6-acylamidopenicillanate sulfoxide is a p-nitrobenzyl ester.
Claim 15
Dependent Claim
7 words
The process according to claim 1 wherein
Claim 16
Dependent Claim
15 words
Me is the tin (II), silver, copper (II), thallium (III) or mercury (II) anion; and
Claim 17
Dependent Claim
15 words
Me is the tin (II), silver, copper (II), thallium (III) or mercury (II) anion; and
Claim 18
Dependent Claim
6 words
R" is methyl, trifluoromethyl or methylphenyl.
Claim 19
Dependent Claim
6 words
R" is methyl, trifluoromethyl or methylphenyl.
Claim 20
Dependent Claim
35 words
The process according to claim 1 wherein said heavy metal sulfonate is selected from the group consisting of tin (II) methanesulfonate, silver methanesulfonate, copper (II) methanesulfonate, thallium (III) methanesulfonate, mercury (II) methanesulfonate and silver p-toluenesulfonate.
Claim 21
Dependent Claim
27 words
The process according to claim 9 wherein said 6-acylamidopenicillanate sulfoxide is the p-nitrobenzyl, p-methoxy-benzyl, cyanomethyl, p-bromophenacyl or p-chlorophenacyl ester of benzylpenicillin sulfoxide, α-azidobenzylpenicillin sulfoxide or phenoxymethylpenicillin sulfoxide.
Claim 22
Dependent Claim
15 words
The process according to claim 10 wherein said sulfoxide is an ester of benzylpenicillin sulfoxide.
Claim 23
Dependent Claim
16 words
The process according to claim 11 wherein said ester is the p-nitrobenzyl ester of benzylpenicillin sulfoxide.
Claim 24
Dependent Claim
15 words
The process according to claim 10 wherein said sulfoxide is an ester of phenoxymethylpenicillin sulfoxide.
Claim 25
Dependent Claim
16 words
The process according to claim 13 wherein said ester is the p-nitrobenzyl ester of phenoxymethylpenicillin sulfoxide.
References Cited (Backward Citations)
US3725399A
Cited
US3853861A
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US3725397A
Cited
US3852281A
Cited
US3799924A
Cited
US3781283A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-12-14 | 1980-06-14 | 1980-12-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-12-14 | 1984-06-14 | 1984-12-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-12-14 | 1988-06-14 | 1988-12-14 | $7700.00 | Window Closed / Lapsed |