Nisshin Flour Milling Co., Ltd.

Nisshin Pharma Inc.

Masahiro Tsuji

Hiroyasu Koyama

Kenji Mori

Yoshikuni Suzuki

Hiroyuki Yamazaki

Toshihiro Takahashi

Yoshiyuki Tahara

Noriyoshi Sueda

Toshiji Sugai

Yoji Tachibana

Shinji Yokoyama

Masao Nagase

Nobuo Ikekawa

Yasushi Okamoto

In a process for the preparation of pentaacetyl-&bgr;-D-glucopyranose by reacting D-glucose with acetic anhydride in the presence of sodium acetate catalyst, the improvement is provided wherein 5-10 mols of acetic anhydride are used per mol of D-glucose and the reaction is performed in an organic solvent. Pentaacetyl-&bgr;-D-glucopyranose is useful as intermediates for the synthesis of raw materials for industrial chemicals, medicines, cosmetics and the like.

Process for the preparation of pentaacetyl-&bgr;-D-glucopyranose

A process of making arbutin and its derivatives comprises solvolyzing an acylated precursor of arbutin or its derivative in a solution comprising an organic solvent and a base, neutralizing the solution with an acid, and crystillizing the product arbutin or its derivative. The process may be employed on an industrial scale and avoids the use of ion exchange columns. The process has the advantages of not requiring ion exchange columns and peripheral devices, which leads to cost and time savings, due to the elimination of column regeneration steps. Waste water from column regeneration is also eliminated.

Process for the preparation of tetrahydropyran derivatives

Disclosed are (S)-2,3-dihydropolyprenol of formula (I) ##STR1## wherein m is 7 or 8 and (S)-2,3-dihydropolyprenyl monophosphate of formula (II) ##STR2## wherein m is 7 or 8 as well as pharmaceutically acceptable salts thereof. They are useful as a medicament for inhibiting the growth and/or metastasis of cancers.

(S)-2,3-dihydropolyprenyl, monophosphate, and agents for inhibiting the

(24S)- and (24R)-1.alpha.,25-Dihydroxyvitamin D.sub.4 compounds and processes for preparing same. Ergosta-5,7-diene compounds which are useful intermediates in the synthesis of the 1.alpha.,25-dihydroxyvitamin D.sub.4 compounds. The D.sub.4 compounds are expected to possess an interesting pharmacological activity in association with the active-type vitamins D.sub.3 and D.sub.2.

1.alpha.,25-dihydroxyvitamin D4 compounds, ergosta-5,7-diene compounds

(22E)-5,7,22-Ergostatriene-1.alpha.,3.beta.,25-triol and the 24-epimer thereof which are new intermediates for the synthesis of 1.alpha.,25-dihydroxyvitamin D.sub.2 and the 24-epimer thereof. A new process for the preparation of 1.alpha.,25-dihydroxyvitamin D.sub.2 and the 24-epimer thereof is also described which comprises irradiation of (22E)-5,7,22-ergostatriene-1.alpha.,3.beta.,25-triol or the 24-epimer thereof followed by isomerization.

Process for the preparation of 1.alpha.,25-dihydroxyvitamin D.sub.2 and

New intermediate, an optically active (1S,5R)-7,7-alkylenedioxy-2-alkoxycarbonylbicyclo[3.3.0]octan-3-one which is useful for the synthesis of an optically active carbacyclin. This intermediate is prepared, as a non-reduced compound, from a racemic compound, (1SR,5RS)-7,7-alkylenedioxy-2-alkoxycarbonyl-cis-bicyclo[3.3.0]octan-3-one , by treatment of the racemic compound with a microorganism. The microorganism has an ability of specifically reducing the keto group of the (1R,5S) epimer of the racemic compound.

Optically active carbacyclin intermediates and processes for the

New intermediate, an optically active (1R,5S,6S,7R)-6-tert-butyldiphenylsilyloxmethyl-7-hydroxy-bicyclo[3.3.0]oc tan-3-one (I) having high optical purity which is useful for the synthesis of an optically active carbacyclin and an optically active pentalenolactone E methyl ester. The compound (I) is also an intermediate compound serving for the purpose of improving the optical purity of (1R,5S,6S,7R)-3,3-ethylenedioxy-6-hydroxymethyl-7-(2'-tetrahydropyranyloxy )bicyclo[3.3.0]octane. The compound (I) is prepared by reacting (1R,5S,6S,7R)-3,3-ethylenedioxy-6-hydroxymethyl-7-(2'-tetrahydropyranyloxy )bicyclo[3.3.0]octane with tert-butylchlorodiphenylsilane in the presence of a base and removing the ethylenedioxy and tetrahydropyranyl groups of the resultant compound under an acid condition.

Optically active bicyclo[3.3.0]octane and processes for the preparation

New intermediate, an optically active (1S,5R)-7,7-alkylenedioxy-2-alkoxycarbonylbicyclo[3.3.0]octan-3-one which is useful for the synthesis of an optically active carbacyclin. This intermediate is prepared, as a non-reduced compound, from a racemic compound, (1SR,5RS)-7,7-alkylenedioxy-2-alkoxycarbonyl-cis-bicyclo[3.3.0]octane-3-on e, by treatment of the racemic compound with a microorganism. The microorganism has an ability of specifically reducing the keto group of the (1R,5S) epimer of the racemic compound.

Four different optical isomers of a new compound, 1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4'-isocarbostyriloxy)-2-p ropanol are now provided as new substances. These four optical isomers are now named as (2R, 1'S)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4'-isocarbostyriloxy )-2-propanol, (2S, 1'S)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4'-isocarbostyriloxy )-2-propanol, (2S, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4'-isocarbostyriloxy )-2-propanol, and (2R, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4'-isocarbostyriloxy )-2-propanol, respectively. These four optical isomers have different activities for their .beta.-adrenergic-blocking effect and .alpha.-adrenergic-blocking effect and are useful as valuable agents for therapeutic treatment of various cardiovascular diseases, as compared to an optically inactive racemic mixture of said isomer compounds. These four optical isomers may be produced and isolated from each other by chromatographing (1'S)- or (1'R)-N-[2'-(o-methoxyphenoxy)-1'-methylethyl]-5-(4'-isocarbostyriloxymeth yl)-2-oxazolidones to isolate either its (5R, 1'S)-isomer and its (5S, 1'S)-isomer, or its (5S, 1'R)-isomer and its (5R, 1'R)-isomer therefrom separately and then hydrolyzing each of these isolated isomers under alkaline conditions to obtain separately (2R, 1'S)-, (2S, 1'S)-, (2S, 1'R)- and (2R, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4'-isocarbostyriloxy )-2-propanols.

Optically active isocarbostyril derivatives and a method of preparing

Compounds of the structure ##STR1## wherein X, R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are as herein defined, effective as .beta.-blockers and hypotensive agents, are described.

Isocarbostyril derivatives

Isocarbostyrils of the formula ##STR1## wherein R is a branched alkyl of 3 to 4 carbon atoms, and the acid addition salts thereof, having .beta.-adrenergic blocking activity, are described.

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Kawagoe, Japan

Masahiro Tsuji