Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-01-20
1996-12-17
Ford, John M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514202, 514208, 540216, C07D50162, A61K 31545
Patent
active
055853722
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT/EP94/01643, filed 17 May 1994.
The present invention relates to new cephalosporin sulphones, their preparation and to pharmaceutical and veterinary compositions containing them. The compounds disclosed in the present invention are tricyclic .beta.-lactam derivatives characterized by a cephem sulfone skeleton fused with a furane, thiophene or pyrrole ring. According to the invention there are provided compounds of formula (I) and the pharmaceutically and veterinarily acceptable salt thereof: ##STR2## wherein R.sub.1 is hydrogen or halogen or an optionally substituted C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 acyloxy or C.sub.1 -C.sub.6 carboxamido group; C.sub.3 -C.sub.6 cycloalkyl, C.sub.6 -C.sub.10 aryl or C.sub.7 -C.sub.14 aralkyl group; -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.7 -C.sub.14 aralkyl group or an optionally substituted --(CH.sub.2).sub.m S(O).sub.n R.sub.5 group wherein m is 0 or 1, n is 0, 1 or 2 and R.sub.5 is either a group defined as R.sub.2 above or an optionally substituted heterocyclyl group; or a group of the formula OCOA, wherein A is hydrogen or an optionally substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.6 -C.sub.10 aryl or C.sub.7-14 aralkyl or heterocyclyl group, together with R.sub.3 constitutes a C.sub.2 -C.sub.6 alkanediyl or an alkanediyl radical optionally substituted by methyl or phenyl, and X is either oxygen or sulphur or NR.sub.6, wherein R.sub.6 is either hydrogen or a group as defined for R.sub.2.
The term halogen preferably encompasses fluorine, chlorine or bromine.
The C.sub.1 -C.sub.6 alkyl group is a straight or branched alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl and so on.
The C.sub.2 -C.sub.6 alkenyl group is a straight or branched alkenyl group such as vinyl, allyl, crotyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl, butenyl, pentenyl and so on.
The C.sub.1 -C.sub.6 alkoxy group is a straight or branched alkoxy group such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, n-hexyloxy and so on.
The C.sub.1 -C.sub.6 alkylthio group is a straight or branched alkylthio group such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, n-pentylthio, n-hexylthio and so on.
The C.sub.1 -C.sub.6 acyloxy group is a straight or branched carboxylic acyloxy such as formyloxy, acetoxy, propionyloxy, butyryloxy, isobutyryloxy, valeryloxy and so on.
The C.sub.1 -C.sub.6 carboxamido group is a straight or branched carboxylic acylamino group such as formamido, acetamido, propionamido, butyramido, isobutyramido, valeramido and so on.
The C.sub.3 -C.sub.6 cycloalkyl group is a monocycloalkyl group such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and so on.
The C.sub.6 -C.sub.10 aryl group is a monocyclic or bicyclic aromatic hydrocarbon group such as phenyl and naphtyl.
The C.sub.7 -C.sub.14 aralkyl group is an alkyl group of 1 to 4 carbon atoms linked to a monocyclic or bicyclic aromatic hydrocarbon group of 6 to 10 carbon atoms. Examples of aralkyl groups are benzyl, phenylethyl and naphtylmethyl.
The heterocyclyl group is a 5- or 6-membered, saturated or unsaturated heterocyclyl ring, containing at least one heteroatom selected from O, S and N, which is optionally fused to a second 5- or 6-membered, saturated or unsaturated heterocyclyl group as above defined, or to a C.sub.3 -C.sub.6 cycloalkyl group, or to a phenyl group.
The above said alkyl, alkenyl, alkoxy, alkylthio, aryl, aralkyl, heterocyclyl groups can be either unsubstituted or substituted by one or more substituents selected from the following ones: be the same or different, are C.sub.1 -C.sub.6 straight or branched alkyl, phenyl or benzyl; wherein R' is as defined above and t is 0, 1, 2 or 3; (i.e., --C(O)CF.sub.3); N-carboxymethylcarbamoyl (i.e., --CONHCH.sub.2 COOH); (i.e., --OC(O)H); defined above;
REFERENCES:
patent: 4547371 (1985-10-01), Doherty et al.
Beeby et al, Tetrahedron Letters No. 37 pp. 3261-3264 (1976).
Alpegiani Marco
Bissolino Pierluigi
Perrone Ettore
Rizzo Vincenzo
Ford John M.
Pharmacia S.p.A.
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