Nippon Shinyaku Company, Ltd.

Takara Shuzo Co., Inc.

Yoji Ezure

Yoshiaki Yoshikuni

Hiroshi Enomoto

Makoto Sugiyama

Nobutoshi Ojima

Yoshiaki Aoyagi

Teruya Nakamura

Shingo Matsumura

Masahiro Yagi

Kiyotaka Konno

Shigeaki Maruo

Katsushige Ikai

Masanobu Kawamata

Takayuki Ozaki

Yukio Fujita

Masashi Yamamoto

Katsunori Miyazaki

Shingo Matsumura, Deceased

Hiroyuki Kuroda

Manabu Itoh

Susumu Sano

Hideyuki Yasuda

Takashi Seto

A method of preparing crystals of a glucosylmoranoline formula (III) ##STR1## wherein R is hydrogen or lower alkyl by fractional cyrstallizatin using a polar solvent and an arylsulfonic acid.

Method of manufacturing moranoline derivatives

2-amino-2-deoxy-D-mannitol is produced from a microorganism strain of the genus Streptomyces or a mutant strain thereof in improved yields and purity.

Method for manufacturing 2-amino-2-deoxy-D-mannitol

Compounds of formula I are useful in the prophylaxis or treatment of hyperglycemic symptoms ##STR1## wherein R is alkyl substituted by one or more hydroxy.

Glucosylmoranoline derivatives and use thereof for inhibiting increase

A compound of formula (I) ##STR1## wherein: B is a divalent substituted or unsubstituted, cyclic or acyclic, saturated or unsaturated hydrocarbon group;

Glucosylmoranoline derivatives

A method of preparing a molecular compound of glucosylmoranoline of the formula I ##STR1## with methanol, which comprises stirring an aqueous solution comprising (I) and other moranoline derivatives with methanol, whereupon crystals of the molecular compound of (I) with methanol are formed.

A compound of the formula (I): ##STR1## in which:  is a single bond or a double bond,

Physiologically active substances named SEN-366

Compounds of the formula (I): ##STR1## and pharmaceutically acceptable salts thereof wherein R.sup.1 is hydrogen, alkyl of 1 to 10 carbon atoms or acyl of 1 to 6 carbon atoms; R.sup.2 is hydrogen or halo; R.sup.3 is hydrogen, alkyl of 1 to 6 carbon atoms or acyl of 1 to 6 carbon atoms; R.sup.4 is hydrogen or alkyl of 1 to 6 carbon atoms; R.sup.5 is hydrogen or acyl of 1 to 6 carbon atoms; X is CONH.sub.2, hydroxyalkyl of 1 to 4 carbon atoms or COOR.sup.6 wherein R.sup.6 is hydrogen or alkyl of 1 to 4 carbon atoms; and Y is CONH.sub.2, hydroxyalkyl of 1 to 4 carbon atoms or COOR.sup.7 wherein R.sup.7 is hydrogen, alkyl of 1 to 10 carbon atoms or benzyl are useful for inhibiting the activity of amino-peptidase B, exhibit immunomodulating action against living organisms and exhibit anti-inflammatory activity.

OF4949

Bisglucosyl moranoline of the formula (I) ##STR1## is useful in inhibiting increase of blood sugar in sugar-loaded animals and humans, and particularly for treatment of diabetes mellitus.

Moranoline derivatives

Moranoline, or 2-hydroxymethyl-3,4,5-trihydroxy piperidine, is prepared by directly reducing an actinomycetes culture solution containing nojirimycin, followed by isolation, as for example, through the utilization of an ion exchange resin. The corresponding N-methyl derivative can be obtained through the addition of formaldehyde to the culture solution prior to the reduction.

Method for the production of 2-hydroxymethyl-3,4,5-trihydroxy piperidine

Moranolines are produced which are useful for controlling blood sugar levels.

Moranoline derivatives and process for preparation thereof

2-Hydroxymethyl-3,4,5-trihydroxy piperidine, or moranoline, is prepared by culturing a moranoline-producing strain of microorganism of the genus Streptomyces in an appropriate culture medium and thereafter isolating moranoline from the culture medium.

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Otsu, Japan

Yoji Ezure