2-substituted cephem derivatives and process for preparing the s

Details 2-substituted cephem derivatives and process for preparing the s 2-substituted cephem derivatives and process for preparing the s

1984-05-08

1986-08-05

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540229, 540230, C07D50122

Patent

active

046044574

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD AND DISCLOSURE OF INVENTION

This invention relates to novel 2-substituted cephem derivatives and to a process for the preparation of the same. More specifically stated, the present invention provides 2-substituted cephem derivatives represented by the formula ##STR4## wherein R.sup.1 represents substituted or unsubstituted phenyl group, substituted or unsubstituted phenylmethyl group or substituted or unsubstituted phenoxymethyl group, R.sup.2 represents hydrogen atom or protective group for carboxylic acid and Y represents alkoxy group, allyloxy group, benzyloxy group, alkylthio group, carboxyalkylthio group or group of the formula ##STR5## wherein R.sup.4 represents hydrogen atom or lower alkyl group, X represents --O--, --S-- or ##STR6## R.sup.5 represents hydrogen atom, lower alkyl group or phenyl group and R.sup.6 represents hydrogen atom or lower alkyl group, and a process for preparing the derivatives.
The 2-substituted cephem derivatives of the formula (II) are novel compounds undisclosed in literature and can be converted into useful compounds having an antibacterial activity by, for example, the saponification of the carboxylic acid-protecting group or acyl exchange at the amido site in the 7-position. For example, the compound (II) can be converted into a compound of the formula (X) which is useful as the antibacterial agent, according to the following reaction equation. ##STR7##
In the above reaction equation, R.sup.1, R.sup.2 and Y are as defined above, M represents hydrogen atom or alkali metal and R represents a group such as that of ##STR8##
Examples of the substituted or unsubstituted phenyl groups represented by R.sup.1 in the formula (II) are phenyl, phenyl substituted with lower alkyl, lower alkoxy, halogen, nitro or the like on the benzene nucleus such as p-methoxyphenyl, p-chlorophenyl, m-chlorophenyl, o-chlorophenyl, p-methylphenyl, p-nitrophenyl, etc. Exemplary of the substituted or unsubstituted phenylmethyl groups are phenylmethyl, phenylmethyl substituted with lower alkyl, lower alkoxy, halogen, nitro or the like on the benzene nucleus such as p-chlorophenylmethyl, p-nitrophenylmethyl, p-methylphenylmethyl, etc. Representative of the substituted or unsubstituted phenoxymethyl groups are phenoxymethyl, phenoxymethyl substituted with lower alkyl, lower alkoxy, halogen, nitro or the like on the benzene nucleus such as p-chlorophenoxymethyl, etc.
Examples of the carboxylic acid-protecting groups represented by R.sup.2 are alkyl, halogenated alkyl, methyl substituted with phenyl optionally substituted and like protective groups commonly used. Preferred examples of the alkyl groups are those having 1 to about 4 carbon atoms such as methyl, tert-butyl, etc. Preferable halogenated alkyl groups are lower alkyl groups having 1 to about 4 carbon atoms and substituted with at least one halogen group such as 2,2,2-trichloroethyl, etc. Preferred methyl groups substituted with phenyl optionally substituted are benzyl, p-nitrophenylmethyl, diphenylmethyl, etc.
Examples of the alkoxy groups represented by Y are lower alkoxy groups having 1 to about 4 carbon atoms such as methoxy, ethoxy, etc. Representative of the alkylthio groups are lower alkylthio groups having 1 to about 4 carbon atoms such as methylthio, ethylthio, butylthio, isobutylthio, etc. Illustrative of the carboxyalkylthio groups are carboxy lower alkylthio groups having about 2 to about 4 carbon atoms such as --SCH.sub.2 COOH, --SCH.sub.2 CH.sub.2 COOH, --SCH.sub.2 CH.sub.2 CH.sub.2 COOH, etc. Exemplary of the groups ##STR9## are furanyl, 2-methylfuranyl, thiophene-2-yl, 2-methylthiophene-5-yl, N-methylpyrrole-2-yl, etc. Representative of the groups ##STR10## are 1,2,3,4-tetrazole-5-thio, 1-phenyl-1,2,3,4-tetrazole-5-thio, 1-methyl-1,2,3,4-tetrazole-5-thio, etc. Illustrative of the groups ##STR11## are 1,3,4-thiadiazole-5-thio, 2-methyl-1,3,4-thiadiazole-5-thio, etc.
The compound (II) can be prepared by reacting a cephem derivative of the formula ##STR12## wherein R.sup.1 and R.sup.2 are as defined above and R.sup.3

REFERENCES:
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