Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1990-05-09
1992-07-28
Rizzo, Nicholas S.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540226, 540227, C07D50136, A61K 31545
Patent
active
051341379
DESCRIPTION:
BRIEF SUMMARY
INTRODUCTION
This invention relates to new cephalosporin antibiotics having a 7.beta.-[2-(2-amino-1,3-thiazol-4-yl)-2-(Z)-(methoxyimino)acetamido]ceph-3 -em-4-carboxylic acid or a pharmaceutically acceptable salt thereto, nucleus, and having part of its novelty focused on the 3-thiomethylceph-3-em position thereof, which compounds are useful as antibiotics, primarily for treating valuable warm-blooded animals to resist, ward off or combat pathogenic infections caused by bacteria susceptible to these cephalosporin compounds.
BACKGROUND OF THE INVENTION
The cephalosporin antibiotic ceftiofur, named as 7-[2-(amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(fur-2-ylcarbo nyl)thiomethyl]-3-cephem-4-carboxylic acid, its alkali metal, alkaline earth metal and amine salts of the carboxylic acid group and easily hydrolyzable ester groups thereof are described and claimed in Labeeuw et al U.S. Pat. No. 4,464,367.
A hydrohalide salt of ceftiofur, particularly the hydrochloride salt thereof, was described and claimed in U.S. patent application Ser. No. 664,651 filed 25 Oct. 1984. A corresponding South African Patent No. 85/7613 has been published disclosing such ceftiofur hydrohalide salts.
Ochiai U.S. Pat. No. 4,278,671 and related U.S. Pat. Nos. 4,510,138 and 4,520,194 disclose some 7-[2-(2-aminothiazol-4-yl)-2-(syn)methoxyiminoacetamido]cephalosporins. Many groups are described for positioning in the R.sub.3 or 3-(R.sub.3 --CH.sub.2 --) cephalosporin molecule position. Among the many such R.sub.3 groups are mentioned hydroxy and mercapto at column 1, lines 67 and 68, but no specific compound such 3-mercaptomethyl type is named therein.
Desacetyl cefotaxime, 7-[2-(2-amino-1,3-thiazol-4-yl)-(syn)-2-methoxyiminoacetamido]-3-hydroxyme thylceph-3-em-4-carboxylic acid, is disclosed in a publication entitled "Disposition of Cefotaxime in Rat, Dog and Man" by C. M. Macdonald, et al in Arzneimittel Forschung Drug Research, 34 (II), No. 12 (1984), pp. 1719 to 1723, but such publication does not disclose the 3-mercaptomethyl compound of this invention or suggest the advantages which we have discovered according to this invention.
Published PCT application WO 82/03395 published Oct. 14, 1982 discloses some therapeutically active organic compounds which exhibit at least one group comprising the structure --S'S"--R, but it does not disclose the cephalosporin compounds claimed here.
Derwent Abstract No. 91799 D/50 of Japanese published application No. J56139-494 published Oct. 30, 1981 of Japanese application No. 042864 filed Apr. 3, 1980 discloses cephamycin disulfide symmetrical dimer compounds but it does not disclose the compounds claimed here.
OBJECTS OF THE INVENTION
It is an object of this invention to provide some new 7.beta.-[-(2-amino-1,3-thiazol-4-yl)-2-(Z)-(methoxyimino)acetamido]ceph-3- em-4-carboxylic acid 3-position derivative antibiotic compounds as compounds per se.
It is another object of this invention to provide useful, veterinary pharmaceutical compositions containing as an active cephalosporin antibiotic component thereof one of the new 7.beta.-[2-(2-amino-1,3-thiazol-4-yl)-2-(Z)-(methoxyimino)acetamido]ceph-3 -em-4-carboxylic acid derivative, compounds of this invention, or a salt thereof.
It is another object of this invention to provide a method or process or use for treating a valuable warm-blooded animal to assist such animal to resist, ward-off or combat infections caused by bacteria susceptible to destruction, neutralization or elimination by administering to such animal an effective antibiotic amount of one of the new 7.beta.-[-(2-amino-1,3-thiazol-4-yl)-2-(Z)-(methoxyimino)acetamido]ceph-3- em-4-carboxylic acid derivative compound of this invention or a pharmaceutically acceptable salt thereof.
SUMMARY OF THE INVENTION
Briefly, this invention provides some new cephalosporin antibiotic compounds, defined by formulas I or II on the STRUCTURE SHEET hereinafter, wherein latter case R.sub.1 is not present, or acceptable acid addition salt anion, and R.sub.2 position so that the total form
REFERENCES:
patent: 4278671 (1981-07-01), Ochiai
patent: 4464367 (1984-08-01), Labeeuw
patent: 4487767 (1984-12-01), Takaya et al.
patent: 4510138 (1985-04-01), Ochiai
patent: 4520194 (1985-05-01), Ochiai
patent: 4950661 (1990-08-01), Olliero et al.
Derwent Abstract of J56139-494 Japanese published application Oct. 30, 1981 of Japanese application 042864 filed Apr. 3, 1980.
C. M. Macdonald et al., "Disposition of Cefotaxime in Rat, Dog and Man", Arzneimittel Forschung Drug Research, 34:1719-1723, (1984).
Arnold Thomas S.
Cazers Alexander R.
Gatchell Catherine L.
Gilbertson Terry J.
Jaglan Prem S.
Gammill Martha A.
Rizzo Nicholas S.
The Upjohn Company
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