ES296840A1 - A procedure for the preparation of antibiotics (Machine-translation by Google Translate, not legally binding) - Google Patents

Abstract

The invention relates to antibiotically active l-substituted-3-cyclohexene compounds of Formul[mu] I, II and III:- wherein R is H, an alkali metal, an alkaline earth metal or C 1-3 alkyl wherein R is OH, C 1-10 alkoxyl, phenoxyl, alkylsubstituted phenoxyl containing up to 10 carbon atoms, benzyloxy, amino or monoalkylamino containing up to 10 C atoms, and R 1 is H, C 1-10 alkanoyl, benzoyl, C 1-10 alkyl-substituted benzoyl or benzyloxycarbonyl in which R is OH, C 1-10 alkoxyl, phenoxyl, C 1-10 alkyl-substituted phenoxyl, benzyoxyl, amino or C 1-10 monoalkylamino, R 1 is H, C 1-10 alkanoyl, benzoyl or C 1-10 alkyl-substituted benzoyl. The acids (+)-3-cyclohexene-1-glyoxylic acid, (+)- 3-cyclohexene-1-glycine and (+)-3-cyclohexene- 1-hydroxyacetic acid are obtained by cultivating Streptomyces antibioticus ATCC 14890 or ATCC 14891, or a mutant thereof capable of producing said acids, in an aqueous nutrient medium and, where appropriate, converting the acid form of the antibiotic to one of the above salts or treating with an esterifying, amidating or acylating agent. The acids are recovered from the fermentation broth by extraction or adsorption. Antibiotically active pharmaceutical compositions contain a 1-substituted-3-cyclohexene of Formul[mu] I, II or III.The invention relates to antibiotically active 1-substituted-3-cyclohexene compounds of Formulae I, II and III:- <FORM:1050371/C2/1> wherein R is H, an alkali metal, an alkaline earth metal or C1- 3 alkyl <FORM:1050371/C2/2> wherein R is OH, C1- 10 alkoxyl, phenoxyl, alkyl-substituted phenoxyl containing up to 10 carbon atoms, benzyloxy, amino or monoalkylamino containing up to 10 C atoms, and R1 is H, C1- 10 alkanoyl, benzoyl, C1- 10 alkyl-substituted benzoyl or benzyloxycarbonyl <FORM:1050371/C2/3> in which R is OH, C1- 10 alkoxyl, phenoxyl, C1- 10 alkyl-substituted phenoxyl, benzyoxyl, amino or C1- 10 monoalkylamino, R1 is H, C1- 10 alkanoyl, benzoyl or C1- 10 alkyl-substituted benzoyl. The acids (+)-3-cyclohexene-1-glyoxylic acid, (+)-3-cyclohexene-1-glycine and (+)-3-cyclohexene-1-hydroxyacetic acid are obtained by cultivating Streptomyces antibioticus ATCC 14890 or ATCC 14891, or a mutant thereof capable of producing said acids, in an aqueous nutrient medium and, where appropriate, converting the acid form of the antibiotic to one of the above salts or treating with an esterifying, amidating or acylating agent. The acids are recovered from the fermentation broth by extraction or adsorption. Antibiotically active pharmaceutical compositions contain a 1-substituted-3-cyclohexene of Formulae I, II or III.