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US3932398A Expired / Lapsed US ⏱️ 0.0 years remaining

3-Halo-cepham derivatives

Assignee: Wyeth LLC
•
Filing: 1973-04-19
•
Granted: 1976-01-13
•
Expires: 1993-04-19
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Abstract

Abstract Penicillin sulfoxides are converted to 3-halo-3-methyl-cepham-4-carboxylic acid esters and amides or the corresponding cephem derivatives by heating the penicillin sulfoxide precursor in a polyhaloalkane solvent to a temperature between 50° to about 150°C. in the presence of an equimolar amount of a neutral or basic catalyst, respectively. The catalysts employed are bases such as pyridine, picoline, lutidine, quinoline, isoquinoline, dimethylaniline or a quaternary ammonium salt. The 3-halo-cepham intermediates produced with a quaternary ammonium catalyst are dehydrohalogenated to afford known cephem derivatives or converted to the free 4-carboxylic acid and the alkali metal, alkaline earth metal or ammonium salts thereof to afford novel antibacterial agents.

Inventors

  • 👤 Abraham Nudelman
  • 👤 Ronald J. McCaully

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 07:54
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/04; C07D215/10; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07D213/16; C07D213/20

Claims Analysis

Total Claims: 3
Claim 1
Independent Claim 97 words
A compound of the formula: ##SPC7## in which R 3 is a member selected from the group consisting of hydroxy, lower alkoxy, 2,2,2-trichloroethoxy, aryloxy of 6 to 10 carbon atoms, aralkoxy of 7 to 12 carbon atoms, alkoxyaralkoxy of 9 to 14 carbon atoms, mono- or di-lower alkylamino, arylamino of 6 to 10 carbon atoms, saccarimido, phthalimido, and OM where M is an alkali metal cation, an alkaline earth metal cation or the ammonium cation; A is a member selected from the group consisting of --Cl, --Br and --I; and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim 97 words
A compound of the formula: ##SPC7## in which R 3 is a member selected from the group consisting of hydroxy, lower alkoxy, 2,2,2-trichloroethoxy, aryloxy of 6 to 10 carbon atoms, aralkoxy of 7 to 12 carbon atoms, alkoxyaralkoxy of 9 to 14 carbon atoms, mono- or di-lower alkylamino, arylamino of 6 to 10 carbon atoms, saccarimido, phthalimido, and OM where M is an alkali metal cation, an alkaline earth metal cation or the ammonium cation; A is a member selected from the group consisting of --Cl, --Br and --I; and the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim 11 words
The compound of claim 1 which is 7-amino-3-chloro-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid, p-nitrobenzyl ester.

References Cited (Backward Citations)

US3275626A Cited
US3725399A Cited
US3725397A Cited
US3668201A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-01-12 1979-07-14 1980-01-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-01-12 1983-07-14 1984-01-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-01-12 1987-07-14 1988-01-13 $7700.00 Window Closed / Lapsed

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