Abstract: Novel derivatives of kanamycin, 1-N-(L-4-amino-2-hydroxy butyryl)-6'-N-alkylkanamycins, have been prepared which possess improved antibacterial activity against gram-positive and gram-negative bacteria including kanamycin-resistant strains.

Abstract: A clinically valuable antibiotic, 3',4'-dideoxykanamycin B is now produced by a reduced number of consecutive steps in an improved overall yield by new processes starting from kanamycin B via intermediate derivatives of kanamycin B in which all the five amino groups are protected with an unsubstituted or substituted benzyloxycarbonyl group and possibly the 2"-hydroxyl group may be protected with a lower alkylsufonyl, arylsulfonyl or aralkylsulfonyl group.

Abstract: A process for preparing a novel antibiotic, 5"-amino-3',5"-dideoxy-ribostamycin, which comprises subjecting a ribostamycin derivative represented by the formula: ##STR1## to selective sulfonylation to form a 3',5"-O-disulfonyl derivative, SUBJECTING THE THUS PRODUCED DERIVATIVE TO AZIDE-FORMING REACTION WITH SODIUM AZIDE,Subjecting the thus produced ribostamycin 3'-O-sulfonyl-5"-azido derivative to deoxylation by treating it with sodium borohydride in an aprotic and polar solvent,Subjecting the thus obtained 3' deoxy derivative to catalytic hydrogenation in the presence of a catalyst to form a 5"-amino derivativeAnd then, removing the remaining protective groups of the last-mentioned derivative.

Abstract: A useful antibiotic, 3',4'-dideoxykanamycin B can be prepared in shortened steps and in an improved overall yield by a new process starting from kanamycin B via new intermediate derivatives of kanamycin B in which all the amino groups and possibly the 2"-hydroxyl group are protected with sulfonyl-type protecting groups selected from lower alkyl-, aryl- and aralkyl-sulfonyl groups.

Abstract: A number of 1N-(.alpha.-hydroxy-.omega.-aminoalkanoyl)-6'N-methyl-3',4'-dideoxykanamyc in B derivatives have been found to possess excellent antibacterial activity against most kanamycin susceptible and resistant organisms. In particular, 1N-(DL-isoseryl)-6'N-methyl-3',4'-dideoxykanamycin B, 1N-(L-isoseryl)-6'-N-methyl-3',4'-dideoxykanamycin B, 1N-(L-4-amino-2-hydroxybutyryl)-6'N-methyl-3',4'-dideoxykanamycin B and 1N-(L-5-amino-2-hydroxyvaleryl)-6'N-methyl-3',4'-dideoxykanamycin B, or an acid addition salt thereof possess these highly desirable attributes.

Abstract: A 1-N-(.alpha.-substituted-.omega.-aminoacyl)-3'-deoxyribostamycin, which is a useful antibiotic active against various drug-resistant bacteria, can be prepared advantageously by a process starting from a protected derivative of ribostamycin in the form of 1,6-carbamate and comprising the 3'-deoxygenation, the splitting of the carbamate linkage and the 1-acylation.

Abstract: A new and useful 1-N-[(S)-.alpha.-hydroxy-.omega.-aminoacyl] derivative of an aminoglycosidic antibiotic, including its deoxy derivative, such as kanamycin B, 3'-deoxyneamine, 3',4'-dideoxyneamine, 3',4'-dideoxyribostamycin or 3',4'-dideoxykanamycin B is now synthetized from the parent substance, aminoglycosidic antiobiotic. The new 1-N-[(S)-.alpha.-hydroxy-.omega.-aminoacyl] derivative shows a wider and/or higher antibacterial activity than the parent substance and is useful in the treatment of infections by gram-negative and gram-positive bacteria, including drug-resistant strains thereof. The preparation of this new derivative may be made by 1-N-acylating the parent aminoglycosidic antibiotic with (S)-.alpha.-hydroxy-.omega.-aminocarboxylic acid with the amino group being protected, and chromatographically separating the acylated products to isolate the desired 1-N-acyl derivative, followed by the removal of the amino-protecting group.

Abstract: 1-N-(.alpha.-hydroxy-.omega.-aminoalkanoyl)-derivatives of 3'-deoxykanamycin A or 6'-N-methyl-3'-deoxykanamycin A are provided as new and useful compounds which are active against gram-negative and gram-positive bacteria, including drug-resistant strains of these bacteria. Examples of these compounds include 1-N-((SR)-.beta.-amino-.alpha.-hydroxypropionyl)-3'-deoxykanamycin A, 1-N-((S)-.gamma.-amino-.alpha.-hydroxybutyryl)-3'-deoxykanamycin A, 1-N-((S)-.delta.-amino-.alpha.-hydroxyvaleryl)-3'-deoxykanamycin A and 1-N-((S)-.gamma.-amino-.alpha.-hydroxybutyryl)-6'-N-methyl-3'-deoxykanamyc in A. The compounds may be prepared by selective acylation of the 1-amino group of 3'-deoxykanamycin A or 6'-N-methyl-3'-deoxykanamycin A with a corresponding .alpha.-hydroxy-.omega.-amino-alkanoic acid.

Abstract: As new semi-synthetic antibiotic derivative are provided N-methanesulfonic acid derivatives of 3',4'-dideoxykanamycin B which are less toxic than the parent antibiotic and have useful high antibacterial activity. They are produced by interacting 3',4'-dideoxykanamycin B, an aldehyde such as paraformaldehyde and sulfurous acid or an alkali metal sulfite reagent.

Abstract: 3',4'-.alpha.-Epoxyneamine and its related aminoglycosidic antibiotic derivatives containing 3',4'-.alpha.-epoxyneamine moiety in the molecule thereof are now provided, which may be in the form of their amino-protected and partially hydroxyl-protected product and which are useful as intermediates for use in the synthetic production of therapeutically valuable 3'-deoxy derivatives of aminoglycosidic antibiotics.

Abstract: This invention relates to new processes for the production of a 1-N-(.alpha.-hydroxy-.omega.-aminoalkanoyl)-3'-deoxy-5-O-pentofuranosylnea mine, including 3'-deoxybutirosins A and B, as a semi-synthetic antibiotic. This invention further relates to new and useful semi-synthetic antibiotics which are produced by the above new processes.

Abstract: 3'-Deoxy derivatives of neamine, 6'-N-alkylneamine, kanamycin B, 6'-N-alkylkanamycin B, ribostamycin, 6'-N-alkylribostamycin and paromamine may be produced by a new process comprising reducing the 3',4'-.alpha.-anhydro derivative (namely, the 3',4'-epoxide derivative) of the aminoglycosidic antibiotics with hydrogen in an alkaline lower alkanol medium containing an alkali metal hydroxide or alkoxide dissolved therein and in the presence of a reducing catalyst such as Raney nickel. The 3',4'-.alpha.-anhydro derivative may be prepared by treating the 3'-sulfonylated derivative of the amino-protected and hydroxyl-protected neamine, 6'-N-alkylneamine, kanamycin B, 6'-N-alkylkanamycin B, ribostamycin, 6'-N-alkylribostamycin or paromamine with an alkali metal hydroxide or alkoxide in a lower alkanol to effect epoxidation between the 4'-hydroxyl group and the carbon atom substituted by the 3'-sulfonic ester group.

Abstract: An 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula: ##STR1## wherein R is a hydrogen atom or .beta.-D-ribofuranosyl group of the formula ##STR2## and R.sub.3 is hydroxyl, amino-NH.sub.2 or acylamino group --NHR.sub.4 in which R.sub.4 is an acyl group, and n is a whole number of 1 to 4, may be produced by subjecting the corresponding O-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula ##STR3## or its hydroxyl-masked and amino-masked form, to the action of a basic medium to produce an acyl-migration product of the formula: ##STR4## and, optionally converting the amino-masking groups into hydrogen atoms and also the hydroxyl-masking group into hydrogen atom in a known manner if said amino-masking groups and said hydroxyl-masking groups are present in the acyl-migration product. The 1-N-((S)-.alpha.-substituted-.omega.

Abstract: An 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula ##STR1## wherein R is a hydrogen atom or .beta.-D-ribofuranosyl group of the formula ##STR2## and R.sub.3 is hydroxyl, amino-NH.sub.2 or acylamino group --NHR.sub.4 in which R.sub.4 is an acyl group, and n is a whole number of 1 to 4, may be produced by subjecting the corresponding O-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula ##STR3## or its hydroxyl-masked and maino-masked form, to the action of a basic medium to produce an acyl-migration product of the formula: ##STR4## and, optionally converting the amino-masking groups into hydrogen atoms and also the hydroxyl-masking group into hydroge atom in a known manner if said amino-masking groups and said hydroxyl-masking groups are present in the acyl-migration product. The 1-N-((S)-.alpha.-substituted-.omega.

Abstract: A new and useful 1-N-[(S)-.alpha.-hydroxy-.omega.-aminoacyl]derivative of an aminoglycosidic antiobiotic, including its deoxy derivative, such as kanamycin B, 3'-deoxyneamine, 3',4'-dideoxyneamine, 3',4'-dideoxyribostamycin or 3', 4'-dideoxykanamycin B is now synthetized from the parent substance, aminoglycosidic antibiotic. The new 1-N-[(S)-.alpha.-hydroxy-.omega.-aminoacyl] derivative shows a wider and/or higher antibacterial activity than the parent substance and is useful in the treatment of infections by gram-negative and gram-positive bacteria, including drug-resistant strains thereof. The preparation of this new derivative may be made by 1-N-acylating the parent aminoglycosidic antibiotic with (S)-.alpha.-hydroxy-.omega.-aminocarboxylic acid with the amino group being protected, and chromatographically separating the acylated products to isolate the desired 1-N-acyl derivative, followed by the removal of the amino-protecting group.

Abstract: Lividomycin B derivatives having enhanced antibacterial activity are provided; the 6'-deoxy-6' substituted or unsubstituted amino lividomycins are prepared by masking the functional groups other than the 4' - and 6' -hydroxyl groups, converting the 6' hydroxyl group to an amino group and then removing the remaining protective groups.

Abstract: Process of producing a 1-N-((S)-.alpha.-hydroxy-.omega.-aminoacyl)-3',4'-dideoxyneamine or -3',4'-dideoxyribostamycin, a useful semi-synthetic antibiotic in which the corresponding 6-O-((S)-.alpha.-hydroxy-.omega.-aminoacyl)-3',4'-dideoxyneamine or -3',4'-dideoxyribostamycine undergoes the acyl-migration reaction by treating with a basic medium.This invention relates to a process for the production of a 1-N-((S)-.alpha.-hydroxy-.omega.-aminoacyl)-3', 4'-dideoxyneamine or -3',4'-dideoxyribostamycin which is useful for the treatment of various bacterial infections. More particularly, this invention relates to a process for the production of 1-N-((S)-.alpha.-hydroxy-.gamma.-amino-n-butyryl)- 3',4'-dideoxyneamine or -3',4'-dideoxyribostamycin.Kanamycins and neamine (that is, neomycin A) are well known aminoglycosidic antibiotics, and riboostamycin is also a known aminoglycosidic antibiotic, originally designated vistamycin or Antibiotic SF-733 (see the "Journal of Antibiotics" Vol. 23, No.

Abstract: New antibacterial agents, 1,2'-di-N-(.alpha.-hydroxyaminoacyl)-kanamycin B and 1,2'-di-N-(.alpha.-hydroxyaminoacyl)-3',4'-dideoxy kanamycin B are described together with methods for their preparation and use.

Abstract: 1-N-isoseryl derivatives of kanamycin A, kanamycin B and 3',4'-dideoxykanamycin B are now synthesized, which are new and useful compounds active against gram-negative and gram-positive bacteria and also against drug-resistant strains of these bacteria. The production of the 1-N-isoserylkanamycins is made by reacting isoserine with the 1-N-amino group of kanamycin with the functional amino group(s) being protected, following by removal of the amino-protecting groups and by chromatographic separation of the desired 1-N-isoserylation product.