US3668202A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for preparing cepham compounds
Assignee: Eli Lilly and Co
•
Filing: 1970-02-24
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Granted: 1972-06-06
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Expires: 1990-02-24
Abstract
Abstract Preparing a 3-hydroxy-3-methyl-cepham-4-carboxylic acid, salt or ester in improved yields by heating a penicillin sulfoxide acid, salt, or ester in the presence of sulfuric or sulfamic acid, or a salt or ester thereof in a solvent system containing a tertiary carboxamide.
Inventors
- 👤 Bennie J Foster
- 👤 Gerald E Gutowski
- 👤 Lowell D Hatfield
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 13:55
CPC Classifications
C; C07; C07D; C07D501/00; C07D501/02; C07D501/08; C07D501/10
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
36 words
at least one of R1, R2, and R3 alkyl, and not more than two of R1, R2, and R3 are phenyl, tolyl, xylyl, and R1, R2, and R3 together contain up to about 18 carbon atoms;
Claim 2
Dependent Claim
60 words
A process as defined in claim 1 wherein a penicillin sulfoxide ester is heated in the presence of sulfuric acid to from about 90* C. to about 120* C. in a reaction mixture containing a tertiary carboxamide wherein each of R1, R2, and R3 is alkyl, such that R1, R2, and R3 together contain up to about 18 carbon atoms.
Claim 3
Dependent Claim
23 words
A process as defined in claim 2 wherein a penicillin sulfoxide ester is heated in the presence of sulfuric acid in N, N-dimethylacetamide.
Claim 4
Dependent Claim
64 words
R1 is hydrogen or alkyl, R2 and R3 are taken together with the nitrogen to which they are bonded to form a saturated monocyclic ring which contains from four to six carbon atoms in the ring, which ring can also contain an oxygen ring member, gamma to the ring nitrogen, and R1, R2, and R3 together contain not more than 12 carbon atoms; and/or
Claim 5
Dependent Claim
32 words
A process as defined in claim 2 wherein 4-nitrobenzyl phenoxymethylpenicillin sulfoxide ester is heated in the presence of sulfuric acid in a mixture of N,N-dimethylacetamide and benzene to form 4-nitrobenzyl 3-hydroxy-3-methyl 7-(phenoxyacetamido)cepham-4-carboxylate.
Claim 6
Dependent Claim
61 words
R1 and R2 are taken together with the amide grouping (-C(O)-N-) to which they are bonded to form a saturated carbonyl containing monocyclic ring having from four to six ring carbon atoms, R3 is alkyl, phenyl, tolyl, or xylyl, and R1, R2, and R3 together contain not more than 14 carbon atoms; to form as product a 3-hydroxy-3-methylcepham-4-carboxylic acid or ester.
Claim 7
Dependent Claim
55 words
A process as defined in claim 1 wherein a penicillin sulfoxide acid is heated in the presence of sulfuric acid in a reaction mixture containing a tertiary carboxamide of the indicated formula wherein each of R1, R2, and R3 is alkyl, such that R1, R2, and R3 together contain up to about 18 carbon atoms.
Claim 8
Dependent Claim
22 words
A process as defined in claim 5 wherein phenoxymethyl penicillin sulfoxide acid is heated in the presence of sulfuric acid in N,N-dimethylacetamide.
Claim 9
Dependent Claim
66 words
A process as defined in claim 1 wherein a penicillin sulfoxide ester is heated in the presence of sulfamic acid to from about 90* C to about 120* C in a reaction mixture containing a tertiary carboxamide of the formula in claim 1 wherein each of R1, R2, and R3 is alkyl, such that R1, R2, and R3 together contain up to about 18 carbon atoms.
Claim 10
Dependent Claim
26 words
A process as defined in claim 7 wherein 4-nitrobenzyl phenoxymethyl penicillin sulfoxide ester is heated in the presence of sulfamic acid in solvent system containing N,N-dimethylacetamide.
Claim 11
Dependent Claim
55 words
A process as defined in claim 1 wherein a penicillin sulfoxide acid is heated in the presence of sulfamic acid in a solvent medium containing a tertiary carboxamide of the indicated formula wherein each of R1, R2, and R3 is alkyl such that R1, R2, and R3 together contain up to about 18 carbon atoms.
Claim 12
Dependent Claim
26 words
A process as defined in claim 8 wherein phenoxymethyl penicillin sulfoxide acid is heated in the presence of sulfamic acid in a solvent system containing N,N-dimethylacetamide.
References Cited (Backward Citations)
US3275626A
Cited
US3507861A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1975-06-06 | 1975-12-06 | 1976-06-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-06-06 | 1979-12-06 | 1980-06-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-06-06 | 1983-12-06 | 1984-06-06 | $7700.00 | Window Closed / Lapsed |