Process for preparing cephalosporin compounds

Details Process for preparing cephalosporin compounds Process for preparing cephalosporin compounds

1984-05-01

1987-05-12

Marantz, Sidney

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540 26, 540 29, C07D50136

Patent

active

046651667

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD AND DISCLOSURE OF THE INVENTION

This invention relates to a process for preparing cephalosporin compounds, and more particularly to a process for preparing cephalosporin compounds represented by the formula ##STR2## wherein R.sup.1 represents an alkyl group, alkenyl group, substituted or unsubstituted aryl group, substituted or unsubstituted arylmethyl group or substituted or unsubstituted phenoxymethyl group, R.sup.2 represents a carboxyl group or protected carboxyl group, and Y represents the residue of a nucleophilic reagent.
The cephalosporin compounds of the formula (V) have antibacterial activity and thus are useful as antibacterial agents. The compounds can be converted into cephalosporin type antibiotics in wide use by deacylating and reacylating the amide group at the 7-position and thus are important intermediates for synthesizing such antibiotics.
An object of the present invention is to provide a process for preparing the cephalosporin compounds of the formula (V) with high purities in high yields by a simple procedure from inexpensive and readily available starting compounds.
Examples of the alkyl groups represented by R.sup.1 in the formula (V) are methyl, ethyl, propyl, isopropyl, buty, tert-butyl and like lower alkyl groups having 1 to 4 carbon atoms. Examples of the alkenyl groups represented by R.sup.1 are allyl, butenyl, hexenyl and like lower alkenyl groups having 2 to 6 carbon atoms. Examples of the aryl groups represented by R.sup.1 are phenyl, naphthyl and the like. Examples of the substituted aryl groups represented by R.sup.1 are phenyl groups having as substituents lower alkyl, halogen, nitro, lower alkyloxy or the like on the aromatic ring, such as tolyl, xylyl, p-chlorophenyl, p-nitrophenyl, p-methoxyphenyl, etc. Examples of the arylmethyl groups represented by R.sup.1 are benzyl, naphthylmethyl, etc. Examples of the substituted arylmethyl groups represented by R.sup.1 are phenylmethyl groups having as substituents lower alkyl, halogen, nitro, lower alkyloxy or the like on the phenyl ring, such as tolylmethyl, p-chlorophenylmethyl, p-nitrophenylmethyl, p-methoxyphenylmethyl, etc. Examples of the substituted or unsubstituted phenoxymethyl groups represented by R.sup.1 are phenoxymethyl, and phenoxymethyl groups having as substituents lower alkyl, halogen, nitro, lower alkyloxy or the like on the phenyl ring, such as tolyloxymethyl, p-chlorophenoxymethyl, p-nitrophenoxymethyl, p-methoxyphenoxymethyl, etc.
Examples of the protected carboxyl groups represented by R.sup.2 are esters of the formula COOR' and acid amides of the formula CONHR' etc. Examples of the groups represented by R' in the foregoing formulae are methyl, 2,2,2-trichloroethyl, diphenylmethyl, benzyl, p-nitrobenzyl, isobutyl, tert-butyl or like carboxylic acid-protecting groups commonly used.
Examples of the residues of nucleophilic reagents represented by Y include groups ##STR3## groups --SR.sup.4, hydroxyl group, protected hydroxyl group, nitroxy group (--ONO.sub.2), etc. Examples of the groups represented by R.sup.3 are lower alkyl groups having 1 to 4 carbon atoms and optionally substituted with halogen, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, etc.; phenyl group; phenyl groups substituted with lower alkyl, halogen, nitro, lower alkyloxy or the like, such as tolyl, p-chlorophenyl, p-nitrophenyl, p-methoxyphenyl; etc. Examples of the groups represented by R.sup.4 are the same as those represented by R.sup.3 or substituted or unsubstituted residues of the aromatic heterocyclic ring, such as the following groups: ##STR4##
Examples of the groups represented by R.sup.5 are hydroxyl-, carboxyl- and amine-protecting groups, such as methyl, ethyl, propyl or like lower alkyl groups. Examples of the protected hydroxyl groups are groups ##STR5## etc. wherein R.sup.3 is as defined above.
According to the present invention, the cephalosporin compounds of the formula (V) can be prepared as follows.
First, a thiazolinoazetidinone derivative of the formula ##STR6## wherein R.sup.1 and R.sup.

REFERENCES:
patent: 4482491 (1984-11-01), Torii, II
Torii-I, Tetrahedron Letters 23(24), pp. 2495-2498, 1982.
Franceschi, Journal of the American Chemical Society, 99(1), pp. 248-250 (1977).

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