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US 4,544,751 AGranted
Thiadiazole derivatives
AssigneeFujisawa Pharmaceutical Co., Ltd.
InventorsTakao Takaya, Hisashi Takasugi, Toshiyuki Chiba, Zenzaburo Tozuka
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AssigneeFujisawa Pharmaceutical Co., Ltd.
InventorsTakao Takaya, Hisashi Takasugi, Toshiyuki Chiba, Zenzaburo Tozuka
Estimating the term…
3,7-disubstituted-3-cephem-4-carboxylic acid compounds having bacteriostatic properties and the following formula: ##STR1## in which R.sup.1 is thiadiazolyl or isothiazolyl, each of which may have suitable substituent(s), or thiazolyl; R.sup.2 is hydrogen or lower alkyl; R.sup.3 is carboxy or protected carboxy; R.sup.4 is hydrogen, acyloxy or a heterocyclicthio group which may have suitable substituent(s); and R.sup.5 is hydrogen or lower alkoxy, process for making same and treating infectious diseases therewith.
The compounds of the formula:
Dependencies are inferred from the claim text.
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From the US filing history. Foreign family members aren’t listed.
Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings: not condensed with other rings
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antibacterial agents
Not condensed with other rings: 1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
Not condensed with other rings: 1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
Term ended 1 Oct 2002 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
The present invention relates to new 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and pharmaceutically acceptable salts thereof. More particularly, it relates to new 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and pharmaceutically acceptable salts thereof which have antimicrobial activites and to processes for the preparation thereof, to pharmaceutical composition comprising the same, and to a method of using the same therapeutically for treatment of infectious diseases in human being and animals.
Accordingly, it is one object of the present invention to provide 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and pharmaceutically acceptable salts thereof, which are highly active against a number of pathogenic microorganisms.
Another object of the present invention is to provide processes for the preparation of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and pharmaceutically acceptable salts thereof.
The following examples are given for the purpose of illustrating the present invention:
(1) Pulverized potassium carbonate (160 g.) was added to a solution of ethyl 2-hydroxyiminoacetoacetate (a mixture of syn and anti isomers) (152 g.) in acetone (500 ml.). Dimethyl sulfate (130 g.) was dropwise added thereto with stirring over 1 hour at 45.degree. to 50.degree. C. and the mixture was stirred for 2 hours. An insoluble material was filtered off and the filtrate was concentrated under reduced pressure. The filtered insoluble material was dissolved in water (500 ml.) and this solution was added to the residue. The mixture was extracted twice with ethyl acetate (300 ml.). The extract was washed twice with water (200 ml.) and with a saturated sodium chloride aqueous solution (200 ml.) and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was distilled under reduced pressure to give colorless oil of ethyl 2-methoxyiminoacetoacetate (a mixture of syn and anti isomers) (145.3 g.), bp 55.degree. to 64.degree. C./0.5 mm Hg.
I.R. spectrum (Film): 1745, 1695, 1600 cm.sup.-1.