Gruppo Lepetit

The Dow Chemical Company

Renato Cricchio

Giancarlo Lancini

Vittorio Arioli

Marisa Berti

Francis Johnson

The invention relates to new water soluble 3-formylrifamycin SV hydrazones wherein the hydrazone moiety contains a phosphonoxy lower alkyl radical which imparts water solubility. The compositions containing said rifamycin derivatives are also an object of this invention. The new rifamycin derivatives and their pharmaceutical compositions are particularly suitable for parenteral administration.

Water soluble hydrazones of 3-formylrifamycin SV, antibacterial

Novel 4-desoxy-thiazole[5,4-c]rifamycin derivatives of formula I ##STR1## wherein R stands for a group --OR.sub.1, --NR.sub.2 R.sub.3 or --NHCOR.sub.4 wherein R.sub.1 represents alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl, R.sub.2 and R.sub.3 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl and aralkyl or R.sub.2 and R.sub.3 taken together with the adjacent nitrogen atom may represent a 5 to 7 membered heterocyclic ring and R.sub.4 is a radical selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, aryl and aralkyl; R.sub.5 is hydrogen or acetyl; and a process for preparing them. The novel compounds have an antibacterial utility.

Process for preparing 4-desoxy-thiazolo[5,4-c]rifamycin derivatives

Novel 4-desoxy-thiazolo[5,4-c]rifamycin derivatives of formula I ##STR1## wherein R stands for a group --OR.sub.1, --NR.sub.2 R.sub.3 or --NHCOR.sub.4 wherein R.sub.1 represents alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl, R.sub.2 and R.sub.3 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl and aralkyl or R.sub.2 and R.sub.3 taken together with the adjacent nitrogen atom may represent a 5 to 7 membered heterocyclic ring and R.sub.4 is a radical selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, aryl and aralkyl; R.sub.5 is hydrogen or acetyl; and a process for preparing them. The novel compounds have an antibacterial utility.

4-Desoxy-thiazolo[5,4-c]rifamycin derivatives and their use as

A process for preparing 4-deoxy-thiazolo[5,4-c]rifamycin SV derivatives of the following general formula ##STR1## wherein R represents hydrogen or a straight or branched alkyl chain containing from 1 to 10 carbon atoms, R.sub.1 is selected from hydrogen and acetyl. Compounds of formula I above, wherein R is a straight or branched alkyl chain containing from 1 to 10 carbon atoms, R.sub.1 is selected from hydrogen and acetyl. These compounds possess antimicrobial utility.

Rifamycin derivatives

A method for preparing thiazolorifamycin derivatives from rifamycin S and a cysteine ester to produce an intermediate product which is cyclized to thiazolorifamycin and the novel products formed therefrom.

Preparation of rifamycin P and Q derivatives

Novel 4-desoxy-thiazolo[5,4-c]rifamycin SV derivatives having antibacterial activity and a method of preparing same by the reaction of rifamycin S with a cysteine derivative followed by the oxidation of the resulting product.

Thiazolo-rifamycin derivatives and a method for their preparation

Hydrazones of 3-formylrifamycin SV of the general formula ##STR1## wherein R.sub.1 is selected from the group hydrogen; alkyl; phenyl; and benzyl; R.sub.2 is selected from the group alkyl; alkenyl; phenyl; and substituted phenyl; with the proviso that when R.sub.1 is hydrogen or alkyl having 1 to 4 carbons, R.sub.2 may not be phenyl; and the 16, 17; 18, 19; 28, 29-hexahydro and 27-demethoxy-27-hydroxy derivatives thereof.

Hydrazones of 3-formylrifamycin SV

Novel rifamycins characterized by the following structural formula ##STR1## WHEREIN Me represents a methyl group, n represents 3, 4, 5 or 6; g represents 0, 1 or 2; and each R represents a lower alkyl group selected from methyl or ethyl substituting for a hydrogen atom of a --CH.sub.2 -- group; and wherein, when g is 2, the two lower alkyl groups may replace hydrogen atoms of two different methylene groups as well as hydrogen atoms of the same methylene group. The compounds of this invention possess a broad spectrum antibacterial utility accompanied by a low toxicity.

Piperazinylimino rifamycins

Substituted piperazinyliminorifamycins having the following structural formula: ##STR1## wherein Me represents a methyl group and Z represents alkenyl of 3 to 5 carbon atoms, alkynyl of 3 to 5 carbon atoms, 5- or 7-membered cycloalkenyl, cycloalkyl-(C.sub.1 -C.sub.2) alkyl wherein the cycloalkyl moiety is a 3- or 7-membered ring or cycloalkenyl-(C.sub.1 -C.sub.2)alkyl wherein the cycloalkenyl moiety is a 5- or 7-membered ring. The compounds have a broad spectrum antibacterial utility accompanied by a low toxicity.

Substituted piperazinyliminorifamycins

Mono- and poly-phenols and derivatives thereof are ring acylated by a Friedel-Crafts acylation reaction in which the hydroxy groups are protected by prior silylation.

Process for ring acylation of phenols

The present invention is concerned with new derivatives of 3-formylrifamycin SV. More particularly the invention relates to O-substituted oximes of 3-formylrifamycin SV of formula I. ##SPC1## wherein R is selected from the group consisting of alkyl of at least 2 carbon atoms, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl, cycloalkoxyalkyl, hydroxyalkyl, carboxyalkyl, carboalkoxyalkyl, carbamylalkyl, cyanoalkyl, nitroalkyl, aryloxyalkyl, aralkoxyalkyl, heterocycloxyalkyl, aminoalkyl, mono- and di-lower alkylaminoalkyl, substituted benzyl, mono- or poly-aryl substituted C.sub.2 -C.sub.8 alkyl and lower alkyl substituted with mono- or polynuclear heterocyclic rings containing at least one 1 to 3 heteroatom selected from oxygen, nitrogen and sulfur, with the exclusion of morpholine; R.sub.1 is H or CH.sub.3 CO; and the derivatives of the same oximes hydrogenated in at least one of the positions 16, 17; 18, 19; and 28, 29. These compounds have antimicrobial activity.

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Varese, Italy

Renato Cricchio