ES407852A1 - Penicillin compounds their production and their medicinal use - Google Patents

Abstract

Procedure for obtaining penicillins, of general formula I **(See formula)** in which they represent: To one of the groups **(See formula)** X one of the groups: **(See formula)** And one of the groups: **(See formula)** Z one of the groups: **(See formula)** Q1 one of the groups: **(See formula)** Q2 one of the groups: **(See formula)** R a linear and branched alkyl radical with up to 5 carbon atoms, R1 a member of the group consisting of alkyl with up to 10 carbon atoms, cycloalkyl with up to 10 carbon atoms, alkenyl with up to 10 carbon atoms and cycloalkenyl with up to 10 carbon, vinyl, aryl vinyl, mono-, di- and trihalogenoalkyl lower atoms, H2N-, R-NH-, (see formula), aryl-NH-, arylalkyl (lower) -amino, alkoxy, with up to 8 carbon atoms, provided that X2 is not simultaneously -SO2-, aralkoxy with up to 8 carbon atoms, provided that X2 does not be -SO2- at the same time, cycloalkoxy with up to 7 carbon atoms, provided that X2 is not simultaneously -SO2-, aryloxy provided that X2 is not -SO2- at the same time, as well as one of the groups: **(See formula)** V a bivalent organic radical with 1 to 3 carbon atoms, n an integer from 0 to 2 inclusive, R2 and R3 members of the group consisting of hydrogen; alkyl and alkenyl each with up to 8 carbon atoms; vinyl, allyl, propenyl, cycloalkyl, and cycloalkenyl each with up to 6 carbon atoms; mono-, di-, and trihalogenoalkyl, aryl; R4, R5 and R6 members of the group consisting of hydrogen, nitro, nitrile, (see formula), (see formula), R-CO-NH-, RO-CO-, R-CO-O- R-, RO-, H2N-SO2-, chlorine, bromine, iodine, fluorine and trifluoromethyl; G a member of the group consisting in hydrogen and R meaning the arrow in the divalent intermediate piece (see formula), that the bonding of two atoms produced by the two free valences of this intermediate piece is not arbitrary, but proceeds in the direction indicated by the arrow; B one of the groups: **(See formula)** R7, R8 and R9 members of the group consisting of hydrogen, halogen, R-, R-O-, R-S-, R-SO-, R-SO2-, nitro, (see formula), R-CO-NH-, HO and R-CO-O-, having R the meaning indicated above, and their non-toxic pharmaceutically tolerable salts, the penicillins of the general formula I and their non-toxic pharmaceutically tolerable salts being able to present as for the chirality center C (see formula), in the two possible configurations R and S and as mixtures of the resulting diastereomers; characterized in that a compound chosen from 6-aminopenicillanic acid (formula II) and compounds of general formulas III and IV are reacted **(See formula)** in which formulas, R10, R11 and R12 each represent alkyl with up to 6 carbon atoms; with carboxylic acids modified in the carboxyl group, of general formula V **(See formula)** in which, A, Z, B and (see formula) have the meanings defined above; the reaction being carried out, in the case of the application of 6-aminopenicillanic acid, in anhydrous or aqueous solvents, in the presence of a base and, in the case of the application of the compounds of general formulas III and IV, in anhydrous solvents and free of hydroxyl groups with or without the addition of a base, at a temperature of the order of about -70º to + 50ºC, preferably -50º to 0ºC. (Machine-translation by Google Translate, not legally binding)