Meiji Seika Kaisha, Ltd.

Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

Sakai Engineering Co., Ltd.

Toshio Yoneta

Hamao Umezawa

Sumio Umezawa

Shunzo Fukatsu

Seiji Shibahara

Katsuharu Iinuma

Tsutomu Tsuchiya

Masao Koyama

Yasushi Murai

Shigeo Seki

Eiichi Akita

Osamu Sakanaka

Yumiko Okada

Takeo Miyazawa

Tadashi Wakazawa

Yukio Horiuchi

Makoto Ohyama

Masayuki Takagi

Shinjiro Sumi

Tadaaki Okada

Kimiaki Yasuda

Hidehi Takebe

Matsuko Katayama

Maki Ohishi

Derivatives of cyclodepsipeptide PF 1022

An antibacterial and deodorant processing agent for the sanitary processing, in particular, for the sanitary processing of a fiber material having a hydrophobic surface, which comprises a derivative of an aminoglycoside antibiotic, and a method for the antibacterial and deodorant processing of a fiber material having a hydrophobic surface with the use of said antibacterial and deodorant processing agent.

Antibacterial and deodorant processing agent and processing method using

1-N-(L-3-amino-2-hydroxypropionyl)-2',-3'-dideoxykanamycin A and 1-N-(L-4-amino-2-hydroxybutyryl)-2',3'-dideoxykanamycin A are now provided which each is a new compound useful as antibacterial agent. The new compounds each is produced by acylating the 1-amino group of 2',3'-dideoxykanamycin A with L-3-amino-2-hydroxypropionic or L-4-amino-2-hydroxybutyric acid.

1-N-(.omega.-Amino-.alpha.-hydroxyalkanoyl-2',3'-dideoxykanamycin A and

3'-Deoxykanamycin A useful as an antibacterial agent can be produced by a new process comprising reacting a 2',2'-di-O-acylated-3'-O-sulfonylated-tetra-N-protected derivative of kanamycin A with a base such as alkali metal alcoholate in a lower alkanol to effect 2',3'- and 3',4'-epoxidation and concurrently removal of the 2'- and 2'-acyl groups, reducing the resultant N-protected 2',3'-anhydro-3'-epi derivative and 3',4'-anhydro-3'-epi derivative of kanamycin A either with hydrogen in the presence of a known hydrogenation catalyst or with sodium borohydride to afford the corresponding N-protected 3'-deoxygenated derivative of kanamycin A and then removing the residual amino-protecting groups therefrom to give 3'-deoxykanamycin A.

Process for the production of 3'-deoxykanamycin A and intermediate

There are provided new compounds, 3',4'-anhydro-4'-epi derivatives of kanamycin A of the formula: ##STR1## wherein R represents an alkyl, aralkyl or aryl group and Y represents an alkylidene, aralkylidene, cycloalkylidene or tetrahydropyranylidene group which are useful as an intermediate for the synthesis of 3',4'-dideoxykanamycin A and 4'-deoxykanamycin A from kanamycin A. The compounds of formula (I) can be prepared by treating the corresponding 4'-O-sulfonyl derivative with an alkali metal alcoholate in a lower alkanol under an alkaline condition.

Derivative of kanamycin A and a process for the preparation thereof

4-Amino-2-hydroxybutyric acid or 2,4-diaminobutyric acid may be readily produced by a new process comprising reacting a propionic acid compound containing a .beta.-carboxamido substituent (-CONH.sub.2) on the carbon atom at the 3-position and optionally containing hydroxyl substituent and protected or unprotected amino substituent on the .alpha.-carbon atom thereof, with an alkanoic acid anhydride in liquid pyridine to convert the carboxamido group into a nitrile group, with occasional acylation of a .alpha.-hydroxyl group, occasionally removing the alkanoyl group from the .alpha.-acyloxyl group of the resulting nitrile intermediate, and then reducing the resultant nitrile compound with hydrogen to convert the nitrile group into an aminomethyl group, and further optionally removing the residual amino-protecting group from the resultant 4-aminobutyric acid compound.

Process for the production of 4-aminobutyric acid or its derivatives

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.

3'-Epi-4'deoxykanamycin B

Growing community of inventors

Yokohama, Japan

Toshio Yoneta