ES428638A1 - Procedure for the preparation of derivatives of 7acilamido-3-cefem-4-carboxilico acid. (Machine-translation by Google Translate, not legally binding) - Google Patents

Abstract

Procedure for the preparation of derivatives of 7-acylamido-3-cephem-4-carboxylic acid, of the general formula (I) **(See formula)** in which x can be zero, 1 or 2, Z can be: 1) a cyano group, a group -CONH2 or a group -COOR or -COR, where R can be a hydrogen atom or a C1-C6 alkyl group, 2) a group R1-SO2-, wherein R1 is a C1-C6 alkyl, amino or hydroxyl group, unsalted or salified with an alkali metal, 3) a group R1-W-, where R1 has the meaning set forth above, and W is an oxygen or sulfur atom, 4) a group (see formula) each of the same or different radicals A and A1 represents a branched or straight chain saturated aliphatic hydrocarbon radical, which may be substituted by one or more substituents chosen from the group consisting of: a) hydroxyl, b) halogen, c) cyano, d) amino, e) -COR- -COOR, where R has the meaning explained above, f) phenyl unsubstituted or substituted by one or more substituents chosen from the group consisting of hydroxyl, halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, and (see formula) where each of the R groups are the same or different, have the aforementioned meaning, g) a heteromonocyclic, pentatomic or hexatomic radical, containing at least one double bond and at least one hetero atom belonging to the class consisting of N, S and O, the radical of which may be unsubstituted or substituted by one or more substituents selected from the group consisting of hydroxyl, halogen, C1-C6 alkyl, mercapto, C1-C6 aliphatic acyl, -CH2CN and (see formula) where each of the R groups, the same or different, has the meaning above exposed And it can be -NH-, -S-, -O-, B represents a pentatomic heteromonocyclic radical containing at least one double bond and at least one heteroatom belonging to the class consisting of I, S and O, the radical of which may be unsubstituted or substituted by one or more substituents chosen from the group consisting of by: a') hydroxyl, cyano, mercapto, C1-C6 alkoxy, halogen, C1-C6 aliphatic acyl, -CH2-CN; b') amino unsubstituted or substituted by a C1-C6 aliphatic acyl group, c') a C1-C6 alkyl group, unsubstituted or substituted by one or more substituents chosen from the group consisting of hydroxyl and halogen, d') a C1-C6 alkenyl group, unsubstituted or substituted by one or more substituents chosen from the group consisting of hydroxyl and halogen, (e') - - (CH2) x1 pH, where x1 is chlorine or 1 and pH is a phenyl radical, which may be substituted or unsubstituted by one or more substituents chosen from the group consisting of C1-C6 alkyl, C1 alkoxy -C6, hydroxyl, halogen and (see formula) where each of the R groups, the same or different, have the aforementioned meaning, (f') a hydrocarbon or cycloaliphatic radical containing from 4 to 7 ring carbon atoms, which may be unsubstituted or substituted by one or more substituents chosen from the group consisting of C1-C6 alkyl and C1-C6 alkoxy, (g') - (see formula), where X2 is zero, 1 or 2 and where each of the R groups, the same or different, has the aforementioned meaning, or the two R groups, taken together with the atom nitrogen, represent a morpholino, pyridyl or piperidinium radical, (h') - -S-R1, -SO2 -R1, where R1 has the meaning set out above, S-CH2-CN, (see formula), - (S) x- -CH2-COOR where R and x1 have the above meaning, - (S-CH2) x-Py, where x1 has the above meaning and Py is a pyridyl radical, M may be hydrogen or a pharmaceutically acceptable non-toxic cation, and its pharmaceutically acceptable salts, characterized in that it comprises: reacting a compound of formula (IV): **(See formula)** in which Y, B and M have the meaning set out above, or a respective reactive derivative, with an acid of the formula (V): **(See formula)** in which x, Z, A and A1 have the meaning indicated above, or with a respective reactive derivative. (Machine-translation by Google Translate, not legally binding)