公开(公告)号：US3925353A

公开(公告)日：1975-12-09

申请号：US39040373

申请日：1973-08-22

申请人： MICROBIAL CHEM RES FOUND

发明人： UMEZAWA HAMAO ,  UMEZAWA SUMIO ,  TSUCHIYA OSAMU

IPC分类号： A61K31/70 ,  A61K31/7028 ,  A61K31/7034 ,  A61K31/7036 ,  A61P31/04 ,  C07H15/224 ,  C07H15/23 ,  C07H15/234 ,  C07H15/236 ,  C08B19/00

CPC分类号： C07H15/224 ,  C07H15/23 ,  C07H15/234

摘要： 6''-N-alkyl derivatives of kanamycin, 3'',4''-dideoxykanamycin B, 3'',4''-dideoxyneamine and 3'', 4''-dideoxyvistamycin, typically represented by 6''-N-methylkanamycin, 6''-N-methyl-3'',4''dideoxykanamycin B and 6''-N-methyl-3'', 4''-dideoxyvistamycin are synthetized by 6''-N-alkyltalation of the parent substances kanamycin, 3'',4''-dideoxykanamycin B, 3'',4''-dideoxynamine and 3'', 4''-dideoxyvistamycin and are new semi-synthetic antibiotics which are usefully active even against Escherichia and Pseudomonas species resistant to the parent substances.

公开(公告)号：US3929761A

公开(公告)日：1975-12-30

申请号：US44999174

申请日：1974-03-11

申请人： MICROBIAL CHEM RES FOUND

发明人： UMEZAWA SUMIO ,  UMEZAWA HAMAO ,  TSUCHIYA TSUTOMU

IPC分类号： C07H15/04 ,  C07H15/18 ,  C07H15/236 ,  C07H15/22

CPC分类号： C07H15/18 ,  C07H15/04 ,  C07H15/234

摘要： 3''-DEOXYKANAMYCIN AS A NEW AND USEFUL KANAMYCIN DERIVATIVE WHICH IS EFFECTIVE EVEN AGAINST KANAMYCIN-RESISTANT STRAINS OF GRAMPOSITIVE AND GRAM-NEGATIVE BACTERIA, AND A PROCESS OF SYNTHETIZING 3''-DIOXYKANAMYCIN FROM KANAMYCIN.

摘要翻译： 作为一种新的有用的卡那霉素衍生物，可以有效地抵抗抗肿瘤抗药性的GRAM-POSITIVE和GRAM-Negative BACTERIA，以及从KAMAMYCIN合成3'-二氧嗪甲酰胺的方法。

公开(公告)号：US3929762A

公开(公告)日：1975-12-30

申请号：US42182173

申请日：1973-12-05

申请人： MICROBIAL CHEM RES FOUND

发明人： UMEZAWA HAMAO ,  UMEZAWA SUMIO ,  TSUCHIYA OSAMU

IPC分类号： C07H15/224 ,  C07G3/00

CPC分类号： C07H15/224

摘要： The 3''-hydroxyl group of neamine and related aminoglycosidic antibiotics is preferentially sulfonylated with an alkylsulfonyl halide, arylsulfonyl halide or benzylsulfonyl halide and the resultant 3''-sulfonic ester group halogenated with a concentrated solution of alkali metal bromide or iodide in an aprotic solvent to yield halogenated intermediates which can be hydrogenated to form corresponding 3''-deoxy derivatives which exhibit useful antibacterial activity even against bacteria resistant to the parent aminoglycosidic antibiotics.

摘要翻译： 神经胺和相关氨基糖苷类抗生素的3'-羟基优先用烷基磺酰卤，芳基磺酰卤或苄基磺酰卤磺酰化，所得的3'-磺酸酯基用碱金属溴化物或碘化物的浓溶液在非质子溶剂中卤化， 产生可被氢化形成相应的3'-脱氧衍生物的卤化中间体，其表现出有利的抗细菌活性，甚至对抗母体氨基糖苷类抗生素的细菌。

公开(公告)号：US3925354A

公开(公告)日：1975-12-09

申请号：US40208673

申请日：1973-10-01

申请人： MICROBIAL CHEM RES FOUND

发明人： UMEZAWA HAMAO ,  UMEZAWA SUMIO ,  TSUCHIYA OSAMU

IPC分类号： A61K31/70 ,  A61K31/7028 ,  A61K31/7034 ,  A61K31/7036 ,  A61K31/704 ,  A61P31/04 ,  C07H15/224 ,  C07H15/23 ,  C07H15/236 ,  C07H15/244 ,  C07H1/00

CPC分类号： C07H15/224 ,  C07H15/23 ,  C07H15/234

摘要： A new process of synthetizing an 1-N-((S)- Alpha -substitutedomega -aminoacyl) derivatives of aminoglycosidic antibiotic, including known compounds such as butirosin B as well as new compounds such as the derivatives of neamines and deoxyribostamycins, is provided according to this invention, in which process the initial aminoglycosidic antibiotic is poly-Nalkloxy- or -aralkyloxy- or aryloxy-carbonylated, the resulting poly-N-alkyloxy- or aralkyloxy- or aryloxy-carbonylated product is treated with a strong base such as sodium hydroxide or an alkali metal hydride to form the cyclic carbamate derivative according to new reactions and in which the cyclic carbamate derivative is treated with a weak base such as barium hydroxide to convert the 1-amino group of the antibiotic selectively into the free state while the other amino groups still remain in the protected condition. The 1-amino group of the antibiotic having the other amino groups protected is then acylated by reacting with the (S)- Alpha -substituted-107 -amino acid, and the acylation product is treated so as to remove the amino-protecting groups, giving the desired compound.