Yamanouchi Pharmaceutical Company Ltd.

Zaidan Hojin Biselbutsu Kagaku Kenkyu Kai (microbial Chemistry Research

Hidenori Iwamoto

Toshinari Tamura

Masuo Murakami

Isao Yanagisawa

Kenichi Tomioka

Yoshio Ishii

Minoru Yamamoto

Makoto Yoshida

Noriyoshi Inukai

Tetsuya Shiozaki, Deceased

Hamao Umezawa

Tomio Takeuchi

Akihiro Tanaka

Sumio Umezawa

Tsutomu Tsuchiya

Shuichi Sakamoto

Shin-ichi Tsukamoto

Osamu Hasegawa

Hideya Matsuda

Soichi Kagami

Tetsuya Shiozaki

Tetsuya Shizaoki

Tokuichi Takagi

Substituted azetidinone compounds are provided which have the formula: ##STR1## wherein one of R.sup.1 and R.sup.2 represents a substituted lower alkyl group, an azido group, an amino group, a lower acylamino group, a mercapto group or a lower alkylthio group and the other represents a hydrogen group, or, both represent hydrogen atoms or lower alkyl groups; R.sup.3 represents a hydrogen atom or a group shown by formula: ##STR2## (wherein X represents ##STR3## (wherein R.sup.5 represents a hydrogen atom or a lower alkyl group) and Y represents a hydroxy group, a lower alkoxy group, an amino group, a mono- or di-lower alkylamino group); R.sup.4 represents a hydrogen atom, a substituted or unsubstituted lower alkyl group or a group shown by formula: --CH.sub.2 CO--A (wherein A represents an amino group or a group shown by formula: ##STR4## (wherein X and Y are as defined above), provided that when R.sup.1 and R.sup.2 are both hydrogen atoms, at least R.sup.4 represents a group other than a hydrogen atom and provided that either R.sup.3 or R.sup.4 represents a group other than a hydrogen atom. The compounds have strong CNS action.

CNS active substituted azetidinone compounds

A novel-4-substituted-2-azetidinone compound shown by the general formula ##STR1## and salts thereof. The compounds of this invention have a strong CNS activity and are useful for improving a disturbance of consciousness in schizophrenia, a head injury, etc., or improving hypobulia, memory loss, etc.

4-substituted-2-azetidinone compound

A novel 4-substituted-2-azetidinone compound shown by the general formula ##STR1## and salts thereof. The compounds of this invention have a strong CNS activity and are useful for improving a disturbance of consciousness in shizophrenia, a head injury, etc., or improving hypobulia, memory loss, etc.

4-substituted-2-azetidinone compound, process of producing the

A novel 4-substituted-2-azetidinone compound shown by the general formula ##STR1## and salts thereof. The compounds of this invention have a strong CNS activity and are useful for improving a disturbance of consciousness in schizophrenia, a head injury, etc., or improving hypobulia, memory loss, etc.

4-Substituted-2-azetidinone compound, process of producing the

Tylosin compounds of the formula ##STR1## wherein R.sub.1 represents a hydroxyl group; a halogen atom; ##STR2## group (wherein R.sub.5 is a hydrogen atom or a lower alkyl group which may be substituted by a hydroxyl group and R.sub.6 is a hydrogen atom, a lower alkyl group which may be substituted by a hydroxyl group, an aryl group, an aralkyl group, a cycloalkyl group having 3-10 carbon atoms, --CO(O).sub.m --R.sub.7 group (wherein m is 0 or 1 and R.sub.7 is a lower alkyl group, an aryl group, an aralkyl group, a furanyl group, or a pyridyl group), or --CH.sub.2 --R.sub.13 group (wherein R.sub.13 is a mono-, di-, or trifluoromethyl group)); --N(CH.sub.2).sub.n group (wherein n is an integer of 2-15) which may be substituted by an oxo group, a hydroxyl group, a lower alkyl group, or a hydroxy lower alkyl group; an imidazolyl group, a morpholino group, or a piperazino group each may be substituted by a lower alkyl group; or --OOCCH.sub.2 --R.sub.8 group (wherein R.sub.8 is ##STR3## group (wherein R.sub.9 and R.sub.10, which may be the same or different, each is a hydrogen atom or a lower alkyl group; said R.sub.9 and R.sub.10 may be combined with each other to form an alkylene group having 3-7 carbon atoms) or --S--R.sub.11 group (wherein R.sub.11 is a furanyl group or a pyridyl group)); R.sub.2 represents a hydrogen atom or a lower alkanoyl group; R.sub.3 represents a methyl group or --CH.sub.2 CHO group; R.sub.4 represents a hydrogen atom or a hydroxyl group; A represents 0.dbd., ##STR4## line  represents a single bond or a double bond; and line ---- represents a single bond, a double bond, or  ; however, when said R.sub.1 is a hydroxyl group, said R.sub.3 is a methyl group and R.sub.4 is a hydrogen atom, or said line ---- is  ; or when said R.sub.1 is a halogen atom, said R.sub.3 is a methyl group of said line ---- is  . The foregoing compounds of this invention are useful as antibiotics.

Tylosin derivatives, their preparation and pharmaceutical compositions

There are disclosed 20-alkoxy-16-alkyl-prostadienoic acid derivatives of the formula: ##STR1## wherein A represents ##STR2## R and R.sup.5, which may be the same or different, each represents a hydrogen atom or a lower alkyl group; and R.sup.1 and R.sup.4, which may be the same or different, each represents a lower alkyl group, and the pharmaceutically acceptable non-toxic salts thereof. These compounds have excellent pharmacological effects as prostaglandin E.sub.2 and prostaglandin F.sub.2.alpha..

20-Alkoxy-16-alkyl-prostadienoic acid derivatives

3,15-Dilower alkyl prostaglandin E.sub.2 derivatives and 3,15-dilower alkyl prostaglandin D.sub.2 derivatives are disclosed. These compounds have antigastric ulcer activity without undesirable side effects to intestinal organs.

Novel 3,15-dilower alkyl PGE.sub.2 derivatives

A 20-alkoxy-16-alkyl-prostadienoic acid derivative shown by the formula ##STR1## wherein A represents ##STR2## R and R.sup.5, which may be the same or different, each represents a hydrogen atom or a lower alkyl group; and R.sup.1 and R.sup.4, which may be the same or different, each represents a lower alkyl group, And the pharmacologically acceptable nontoxic salts thereof. The compounds have excellent effects as prostaglandin E.sub.2 and prostaglandin F.sub.2.alpha..

20-Alkoxy-16-alkyl prostadienoic acid derivatives

Novel prostaglandin derivatives are provided having the formula: ##STR1## wherein A represents ##STR2## one of R.sub.3 and R.sub.4 represents a hydrogen atom and the other of them represents a lower alkyl group; one of R.sub.5 and R.sub.6 represents a hydrogen atom and the other of them represents a hydroxyl group; and one of R.sub.7 and R.sub.8 represents a hydrogen atom and the other of them represents a lower alkyl group. The compounds of this invention have excellent effects as prostaglandin E.sub.2 and prostaglandin F.sub.2.sub..alpha..

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Saitama, Japan

Hidenori Iwamoto