US3725399A
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METHOD OF PRODUCING 7{62 -ACYLAMIDO-3-METHYLCEPH-3-Em-4-CARBOXYLIC ACID ESTERS
Assignee: Glaxo Laboratories Ltd
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Filing: 1970-03-10
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Granted: 1973-04-03
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Expires: 1990-03-10
Abstract
Abstract The invention relates to a process for the preparation of 7 Beta -acylamido-3-methylceph-3-em-4-carboxylic acid esters from 6 Beta -acylamido penicillanic acid 1-oxide esters in the presence of catalysts which are salts or complexes of acids with nitrogen bases having a pKb of not less than 4. The salts or complexes may be formed in situ.
Inventors
- 👤 P Sandford
- 👤 N Ellerton
- 👤 W Paradise
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 13:11
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/3804; C07F9/3808; C07D; C07D499/00
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
36 words
A process as defined in claim 1 wherein said catalyst is a salt of an acid selected from the group consisting of methane sulphonic acid, toluene-p-sulphonic acid, p-xylene sulphonic acid, naphthalene-2-sulphonic acid and pyridyl sulphonic acid.
Claim 2
Dependent Claim
16 words
A process as defined in claim 1 wherein said catalyst is a salt of orthophosphoric acid.
Claim 3
Dependent Claim
38 words
A process as defined in claim 1 wherein said catalyst is a salt of an acid selected from the group consisting of a lower alkyl phosphonic acid an a chloro-, bromo- or iodo- substituted lower alkyl phosphonic acid.
Claim 4
Dependent Claim
38 words
A process as defined in claim 1 wherein said catalyst is a salt of an acid selected from the group consisting of methane phosphonic acid, ethane phosphonic acid, trichloromethane phosphonic acid, iodomethane phosphonic acid and dichloromethane phosphonic acid.
Claim 5
Dependent Claim
37 words
A process as defined in claim 1 wherein said catalyst is a salt of an acid selected from the group consisting of benzene phosphonic acid, a chloro-, bromo- or iodo-benzene phosphonic acid and a mitro-benzene phosphonic acid.
Claim 6
Dependent Claim
41 words
A process as defined in claim 1 wherein said catalyst is a salt of an unsaturated heterocyclic tertiary base selected from the group consisting of pyridine, quinoline, isoquinoline, benzimidazole and pyridine, quinoline, isoquinoline or benzimidazole substituted by a lower alkyl group.
Claim 7
Dependent Claim
45 words
A process as defined in claim 1 wherein said catalyst is a salt of a member selected from the group consisting of aniline, a chloroaniline, a lower alkyl aniline, a hydroxy aniline, a lower alkoxy aniline, a nitroaniline, a carboxyaniline and a N-lower alkyl aniline.
Claim 8
Dependent Claim
47 words
A process as defined in claim 1 wherein said salt is obtained by the reaction of substantially molar equivalents of an acid selected from the group consisting of a phosphorus acid, methane sulphonic acid, toluene p-sulphonic acid, p-xylene sulphonic acid and pyridine sulphonic acid with said amine.
Claim 9
Dependent Claim
55 words
A process as defined in claim 1 wherein said salt is formed from an amine selected from the group consisting of pyridine; 2-methyl-, 3-methyl- and 4-methyl-pyridines; quinoline and isoquinoline and an acid selected from the group consisting of orthophosphoric, methane phosphonic, ethane phosphonic, iodomethane phosphonic, dichloromethane phosphonic, trichloromethane phosphonic, bromobenzene phosphonic and nitrobenzene phosphonic acids.
Claim 10
Dependent Claim
26 words
A process as defined in claim 1 wherein said salt is obtained in situ by the reaction of substantially molar equivalents of pyridine and orthophosphoric acid.
Claim 11
Dependent Claim
25 words
A process as defined in claim 1 wherein said salt is obtained by the reaction of substantially molar equivalents of pyridine and dichloromethane phosphonic acid.
Claim 12
Dependent Claim
30 words
A process as defined in claim 1 wherein said salt is obtained by the reaction of about two molar equivalents of pyridine and one molar equivalent of dichloromethane phosphonic acid.
Claim 13
Dependent Claim
25 words
A process as defined in claim 1 in which a proportion of said salt not exceeding 1.0 mole per mole of penicillin oxide is used.
Claim 14
Dependent Claim
24 words
A process as defined in claim 14 wherein the proportion of said salt is from 0.01 to 0.2 mole per mole of penicillin oxide.
Claim 15
Dependent Claim
13 words
A process as defined in claim 1 wherein the organic solvent is dioxan.
Claim 16
Dependent Claim
40 words
A process as defined in claim 1 wherein said solvent selected from the group consisting of ethyl methyl ketone, iso-butyl methyl ketone, methyl n-propyl ketone, n-propyl acetate, n-butyl acetate, iso-butyl acetate, sec-butyl acetate, diethyl carbonate and diethylene glycol dimethyl ether.
Claim 17
Dependent Claim
46 words
A process as defined in claim 1 in which the reaction is effected at the boiling point of the solvent and wherein a desiccating agent, which is inert under the reaction conditions, is inserted in a reflux return line to remove water formed during the reaction.
References Cited (Backward Citations)
US3275626A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1976-04-02 | 1976-10-02 | 1977-04-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1980-04-02 | 1980-10-02 | 1981-04-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1984-04-02 | 1984-10-02 | 1985-04-03 | $7700.00 | Window Closed / Lapsed |