Takeda Chemical Industries, Inc.

Kentaro Hiraga

Kouichi Yoshioka

Yoshiaki Saji

Giichi Goto

Tetsuya Okutani

Tsunehiko Asako

Tetsuo Okauchi

Yasuo Sato

Takuichi Miki

Michio Masuoka

Ryo Nakayama

The compound of the formula ##STR1## wherein X is a cyclic group which may optionally be substituted; Y is a carboxyl group which may optionally be esterified or amidated; Z is --CH.dbd.CH--CH.dbd.CH--, --S--(CH.sub.2).sub.l --S-- is an integer of 1 to 3), --N.dbd.CH--CH.dbd.N-- or --(CH.sub.2).sub.m --(m is an integer of 3 to 5); ring A may optionally be substituted with halogen, nitro, amino, alkanoylamino, alkoxycarbonyl, carboxyl or carbamoyl; and n is an integer of 1 to 3, and salts thereof. The compounds display a strong antianxiety effect to mammalian animals and are useful for the prevention or treatment of a disease such as psychoromatic disease and anxiety neurosis.

Pyrrols [3,4-8]pyrazine derivatives, their production and use as

The compound of the formula ##STR1## wherein X is a cyclic group which may optionally be substituted; Y is a carboxyl group which may optionally be esterified or amidated; Z is --CH.dbd.CH--CH.dbd.CH--, --S--(CH.sub.2).sub.l --S-- (l is an integer of 1 to 3), --N.dbd.CH--CH.dbd.N-- or --(CH.sub.2).sub.m -- (m is an integer of 3 to 5); ring A may optionally be substituted with halogen, nitro, amino, alkanoylamino, alkoxycarbonyl, carboxyl or carbamoyl; and n is an integer of 1 to 3, and salts thereof. The compounds display a strong antianxiety effect to mammalian animals and are useful for the prevention or treatment of a disease such as psychoromatic disease and anxiety neurosis.

1,3-dithiolano-, 1,4-dithiino- and 1,4-dithiepino[2,3-C]pyrrole

The compound of the formula ##STR1## wherein X is a cyclic group which may optionally be substituted; Y is a carboxyl group which may optionally be esterified or amidated; Z is --CH.dbd.CH--CH.dbd.CH--, --S--(CH.sub.2).sub.l --S--(l is an integer of 1 to 3), --N.dbd.CH--CH.dbd.N-- or --(CH.sub.2).sub.m --(m is an integer of 3 to 5); ring A may optionally be substituted with halogen, nitro, amino, alkanoylamino, alkoxycarbonyl, carboxyl or carbamoyl; and n is an integer of 1 to 3, and salts thereof. The compounds display a strong antianxiety effect to mammalian animals and are useful for the prevention or treatment of a disease such as psychosomatic disease and anxiety neurosis.

Condensed pyrrolinone derivatives, their production and use

Novel acaricidal agents which contains, as an active ingredient, a pyrroline derivative of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each hydrogen, halogen or lower alkyl;

Acaricidal agents

Novel estradiol derivatives of the formula ##STR1## wherein R.sup.1 means an alkyl group of two or more carbon atoms, and R.sup.2 is hydrogen or an acyl group, have antiestrogen activity and are useful as antiestrogen drugs.

Estradiol derivatives

Dehydroxylation of aminoglycoside antibiotics is carried out by halogenation of phosphorylated aminoglycoside antibiotics followed by reduction of thus halogenated antibiotics. The dehydroxylation process is entirely new and gives the final product in a high yield. The resulting deoxyaminoglycoside antibiotics are effective against microorganisms including aminoglycoside antiobiotics-resistant microorganisms.

Dehydroxylation of aminosugars

Deoxyaminoglycoside antibiotics are prepared in a high yield from phosphorylated aminoglycosides by reacting a phosphorylated aminoglycoside (a) with a silylating agent, or (b) successively with (i) a silylating or acylating agent and (ii) a halogenating agent; then subjecting thus obtained intermediate to reduction. Deoxyaminoglycoside antibiotics are useful for treating infections caused by microorganisms which are resistant or non-resistant to the corresponding aminoglycoside antibiotics.

Epiminodeaminodeoxyaminoglycoside antibiotics and intermediates

Novel steroid compounds are provided represented by the formula: ##SPC1## Wherein each of R.sup.1 and R.sup.2 represents hydrogen or methyl group or R.sup.1 and R.sup.2 may be combined with each other to represent methylene group, n is 2 or 3 and the dotted line means a double bond at 6-exo-position when n is 2 or between 6- and 7-position when n is 3. These novel compounds show a strong anti-androgenic activity, especially by oral administration, and can be used as a remedy for the prostatomegaly.

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Nagaokakyo, Japan

Kentaro Hiraga