2-acyloxycephem derivatives

Details 2-acyloxycephem derivatives 2-acyloxycephem derivatives

1994-11-04

1996-12-24

Tsang, Cecilia

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

514204, 514207, 504230, 5041223, 504226, C07D50104, C07D50114, C07D50160, A61K 31545

Patent

active

055873731

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to new cephalosporins, their preparation and to pharmaceutical and veterinary compositions containing them.
The compounds disclosed in the present invention are cephem sulphones or sulphoxides featuring the simultaneous presence on the cephem skeleton of an acyl group at C-4 and an acyloxy group at C-2.
According to the invention there are provided cephalosporin sulphones of formula (I) and the pharmaceutically and veterinarily acceptable salts thereof: ##STR2## wherein n is one or two: A and B are each, independently, hydrogen or an organic radical selected from optionally substituted C.sub.1 -C.sub.12 straight or branched alkyl, C.sub.2 -C.sub.12 alkenyl, C.sub.2 -C.sub.12 alkynyl, C.sub.6 -C.sub.14 aryl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.5 -C.sub.8 cycloalkenyl, or C.sub.7 -C.sub.18 aralkyl, C.sub.8 -C.sub.18 aralkenyl, C.sub.8 -C.sub.18 aralkynyl, (cycloalkyl)alkyl, (cycloalkyl)alkenyl, heterocyclyl, (heterocyclyl)alkyl and (heterocyclyl)alkenyl groups; zero, one or two and A is as defined above; --NH--Z wherein Z is a mono, di- or tripeptide composed of D or L .alpha.-aminoacids chosen from Ala, Gly, Val, Leu, Ile and Phe, and in which .alpha.-amino acids the terminal amino group is either free or acylated by a group --C(O)A or --C(O)OA wherein A is as defined above; defined above; above; S(O).sub.m A wherein m and A are as defined above; and Z are as defined above; above; and A', being the same or different, is as defined above for A; or A and A' taken together with the nitrogen atom to which they are attached represent a heterocyclic ring; defined above and A", being the same or different, is as defined for A; or A is alkyl and A' and A" together with the nitrogen atom to which they are attached represent a heterocyclic ring, or A and A' and A" together with the nitrogen atom to which they are attached represent a heterocyclic ring; wherein A and Z are as defined above.
As referred to herein a C.sub.1 -C.sub.12 alkyl group is straight or branched, for instance C.sub.1 -C.sub.10 alkyl, typically C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.4 alkyl. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl and so on.
A C.sub.2 -C.sub.12 alkenyl group is straight or branched, for instance C.sub.2 -C.sub.10 alkenyl, typically C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.4 alkenyl. Examples include vinyl, allyl, crotyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl, butenyl, pentenyl and so on.
A C.sub.2 -C.sub.12 alkynyl group is straight or branched, for instance C.sub.2 -C.sub.10 alkynyl, typically C.sub.2 -C.sub.6 alkynyl or C.sub.2 -C.sub.4 alkynyl. Examples include ethynyl, propargyl, 1-propynyl, 1-butynyl, 2-butynyl and so on.
A C.sub.6 -C.sub.14 aryl group is preferably a monocyclic, bicyclic or tricyclic aromatic hydrocarbon group of 6 to 14 carbon atoms, such as phenyl, naphthyl, phenanthryl or anthryl.
A C.sub.3 -C.sub.8 cycloalkyl group is preferably a saturated carbocyclic group of 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and so on.
A C.sub.5 -C.sub.8 cycloalkenyl group is preferably an unsaturated carbocyclic group such as cyclopentenyl, cyclohexenyl and so on.
A C.sub.7 -C.sub.18 aralkyl group is preferably an alkyl group of 1 to 4 carbon atoms linked to a monocyclic, bicyclic or tricyclic aromatic hydrocarbon group of 6 to 14 carbon atoms. Examples of aralkyl groups are benzyl, phenylethyl, naphthylmethyl, naphthylethyl and anthrylmethyl.
A C.sub.8 -C.sub.18 aralkenyl group is preferably an alkenyl group of 2 to 4 carbon atoms linked to a monocyclic, bicyclic or tricyclic aromatic hydrocarbon group of 6 to 14 carbon atoms. Examples of aralkenyl groups are styryl, 2-phenyl-1-propenyl, 3-phenyl-2-butenyl, 2-naphthylethenyl, anthrylethenyl and so on.
A C.sub.8 -C.sub.14 aralkynyl group is preferably an alkynyl group of 2 to 4 carbon atoms linked to a monocyclic, bicyclic or tricyclic aromatic hydrocarbon group of 6 to 10 carbon atoms. Examples of aralkynyl groups are 2-phenylethyny

REFERENCES:
patent: 5077286 (1991-12-01), Bissolino et al.
patent: 5348952 (1994-09-01), Bissolino et al.

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