US4093625A
Expired / Lapsed
US
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6-Sulfur analogs of penicillins and cephalosporins
Assignee: Massachusetts Institute of Technology
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Filing: 1976-08-09
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Granted: 1978-06-06
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Expires: 1996-08-09
Abstract
Abstract Sulfur analogs of 6-aminopenicillanic acid and biologically active derivatives thereof are formed in a photochemical reaction of the esters of 6-diazopenicillanic acid with thiol compounds. Sulfur analogs of 7-aminocephalosporanic acid and biologically active derivatives thereof may be analogously formed in a photochemical reaction of the esters of 7-diazocephalosporanic acid with thiol compounds, or preferably, are formed from the corresponding sulfur analogs of 6-aminopenicillanic acid and derivatives thereof, through sulfoxide rearrangement of the thiazolidine ring of penicillins to the dihydrothiazine ring system of cephalosporins. These sulfur analogs of penicillins and cephalosporins are new antibacterial agents and display antibacterial activity against a wide variety of organisms.
Inventors
- 👤 Thomas J. Commons
- 👤 John C. Sheehan
- 👤 Young-Sek Lo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:03
CPC Classifications
C; C07; C07D; C07D499/00; A; A61; A61P; A61P31/00; A61P31/04
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
59 words
A compound having the formula: ##STR13## wherein R 2 is a conventional penicillin pharmaceutically acceptable group and R 3 is hydrogen or an organic moiety which is electrophyllic as compared to the sulfur to which it is attached, selected from the group of lower alkyl cyclopentyl, cyclohexyl, methycyclohexyl, phenyl, benzyl, tolyl, and a conventional pencillin side chain acyl radicals.
Claim 2
Dependent Claim
59 words
A compound having the formula: ##STR13## wherein R 2 is a conventional penicillin pharmaceutically acceptable group and R 3 is hydrogen or an organic moiety which is electrophyllic as compared to the sulfur to which it is attached, selected from the group of lower alkyl cyclopentyl, cyclohexyl, methycyclohexyl, phenyl, benzyl, tolyl, and a conventional pencillin side chain acyl radicals.
Claim 3
Dependent Claim
32 words
The compound of claim 1 wherein R 2 is selected from the group of hydrogen, substituted and unsubstituted aliphatic, alicyclic, aromatic, acyl and organosilyl radicals, alkali metal ions and quaternary ammonium ions.
Claim 4
Dependent Claim
28 words
The compound of claim 1 wherein R 2 is selected from the group of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkaryl, acyl, acylamino, acylaminoalkyl, imino and acrylacyl.
Claim 5
Dependent Claim
10 words
The compound of claim 1 wherein R 2 is βββ-trichloroethyl.
Claim 6
Dependent Claim
10 words
The compound of claim 1 wherein R 2 is benzyl.
Claim 7
Dependent Claim
10 words
The compound of claim 1 wherein R 2 is benzhydral.
Claim 8
Dependent Claim
10 words
The compound of claim 1 wherein R 2 is hydrogen.
Claim 9
Dependent Claim
17 words
The compound of claim 1 wherein R 2 is selected from the group of sodium and potassium.
Claim 10
Dependent Claim
10 words
The compound of claim 1 wherein R 2 is t-butyl.
Claim 11
Dependent Claim
10 words
The compound of claim 2 wherein R 2 is trialkylsilyl.
Claim 12
Dependent Claim
15 words
The compound of claim 1 wherein R 3 is a conventional penicillin, sidechain acyl radical.
Claim 13
Dependent Claim
38 words
The compound of claim 1 wherein R 3 is selected from the group of hydrogen, formyl, acetyl, phenyl, phenylacetyl, phenoxyacetyl, p-aminophenylacetyl, α-carboxylphenylacetyl, benzyl, benzoyl, 2-thienylacetyl, aminocarbamyl, phenylglycyl, methyl sulfonyl, benzyl sulfonyl, o-aminophenylsulfonyl, p-aminobenzylsulfonly, carbobenzoxy, α-carbonaphthoxy, carbo(2-thienylmethoxy), and (1-phenyl,2-formylamino)ethoxycarbonyl.
Claim 14
Dependent Claim
10 words
The compound of claim 11 wherein R 3 is hydrogen.
Claim 15
Dependent Claim
10 words
The compound of claim 11 wherein R 3 is benzoyl.
Claim 16
Dependent Claim
10 words
The compound of claim 11 wherein R 3 is phenylacetyl.
Claim 17
Dependent Claim
10 words
The compound of claim 11 wherein R 3 is benzyl.
Claim 18
Dependent Claim
10 words
The compound of claim 11 wherein R 3 is chloroacetyl.
Claim 19
Dependent Claim
10 words
The compound of claim 11 wherein R 3 is phenoxyacetyl.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-05 | 1981-12-05 | 1982-06-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-05 | 1985-12-05 | 1986-06-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-05 | 1989-12-05 | 1990-06-06 | $7700.00 | Window Closed / Lapsed |