Yamanouchi Pharmaceutical Company Ltd.

Masuo Murakami

Kozo Takahashi

Ichiro Isaka

Toichi Takenaka

Masaru Iwanami

Masaharu Fujimoto

Kiyoshi Murase

Isao Souzu

Shiro Tachikawa

Teruaki Ozasa

Yasuo Isomura

Isao Yanagisawa

Noriki Ito

Kenichi Tomioka

Toshinari Tamura

Tadao Shibanuma

Hidenori Iwamoto

Hiroshige Homma

Kazuo Kubo

Yoshio Ishii

Teruya Kashiwagi

Noriyoshi Inukai

Ryutaro Kawai

Toshiyasu Mase

Kunihiro Niigata

Yoshinobu Nagano

Tetsuya Maeda

Shinji Usuda

Akio Koda

Masaaki Takeda

Jun Sekino

Mutsuo Takashima

Sumio Iwanami

Kiyoshi Okazaki

Hidemi Shimizu

Hisashi Ida

Kuniichiro Yano

Shigemi Kawahara

Osamu Hasegawa

Yoshihisa Nozaki

Norio Sato

Hiroitsu Kawata

Yukiyasu Murakami

Yasufumi Hirata

Hiroitsu Kawada

Tetsuya Shiozaki, Deceased

Norio Kawahara

Kohzi Nakano

Takashi Fujikura

Noriaki Nagano

Tadayoshi Ohmura

Tadao Kojima

Atsuki Yamazaki

Hiroshi Sugiura

Kazuharu Tamazawa

Hideya Matsuda

Soichi Kagami

Hidefumi Matsui

Khozi Nakano

Tetsuya Shizaoki

Tokuichi Takagi

Yasuhumi Hirata

Hiroyoshi Ino

Tetsuya Shiozaki

Teruya Ashiwagi

Yuji Kawashima

Isao Souzo

Hiroshi Horiguchi

Novel nitrogen-containing heterocyclic compounds shown by the formula ##STR1## wherein one of R.sub.1 and R.sub.2 represents a lower alkyl group, a phenyl group, a halophenyl group, or a lower alkoxyphenyl group and the other of them represents a hydrogen atom, a lower alkyl group, or a phenyl lower alkyl group; said R.sub.1 and R.sub.2 may combine with each other to form a trimethylene group or a tetramethylene group; R.sub.3 represents a hydrogen atom, a lower alkyl group, a phenyl group, or a phenyl lower alkyl group; X represents an oxygen atom, a sulfur atom, an imino group, or a group shown by ##STR2## (wherein m represents 1 or 2 and R.sub.4 represents a lower alkyl group, a hydroxy lower alkyl group, a cycloalkyl group or a phenyl lower alkyl group); and Y represents an ethylene group which may be substituted by lower alkyl group, a trimethylene group, a tetramethylene group, a vinylene group which may be substituted by a lower alkyl group, or ##STR3## (wherein R.sub.5 represents a hydrogen atom, a lower alkyl group, a trifluoromethyl group, or a phenyl group); said X is the group shown by ##STR4## when one of said R.sub.1 and R.sub.2 is a lower alkyl group and the other is a hydrogen atom, and said Y is an ethylene group, and the pharmacologically acceptable non-toxic salts thereof. The compounds described above are strong analgesic anti-inflammatory agents.

Nitrogen-containing heterocyclic ring derivatives and analgesic and

Novel nitrogen-containing heterocyclic compounds shown by the formula ##STR1## wherein one of R.sub.1 and R.sub.2 represents a lower alkyl group, a phenyl group, a halophenyl group, or a lower alkoxyphenyl group and the other of them represents a hydrogen atom, a lower alkyl group, or a phenyl lower alkyl group; said R.sub.1 and R.sub.2 may combine with each other to form a trimethylene group or a tetramethylene group; R.sub.3 represents a hydrogen atom, a lower alkyl group, a phenyl group, or a phenyl lower alkyl group; X represents an oxygen atom, a sulfur atom, an imino group, or a group shown by ##STR2## wherein m represents 1 or 2 and R.sub.4 represents a lower alkyl group, a hydroxy lower alkyl group, a cycloalkyl group or a phenyl lower alkyl group; and Y represents an ethylene group which may be substituted by a lower alkyl group, a trimethylene group, a tetramethylene group, a vinylene group which may be substituted by lower alkyl group, or ##STR3## wherein R.sub.5 represents a hydrogen atom, a lower alkyl group, a trifluoromethyl group, or a phenyl group; said X is the group shown by ##STR4## when one of said R.sub.1 and R.sub.2 is a lower alkyl group and the other is a hydrogen atom, and said Y is an ethylene group, and the pharmacologically acceptable non-toxic salts thereof. The compound described above are strong analgesic anti-inflammatory agents.

Nitrogen-containing heterocyclic ring derivatives

Novel nitrogen-containing heterocyclic compounds shown by the formula ##STR1## wherein one of R.sub.1 and R.sub.2 represents a lower alkyl group, a phenyl group, a halophenyl group, or a lower alkoxyphenyl group and the other of them represents a hydrogen atom, a lower alkyl group, or a phenyl lower alkyl group; said R.sub.1 and R.sub.2 may combine with each other to form a trimethylene group or a tetramethylene group; R.sub.3 represents a hydrogen atom, a lower alkyl group, a phenyl group, or a phenyl lower alkyl group; X represents an oxygen atom, a sulfur atom, an imino group, or a group shown by ##STR2## wherein m represents 1 or 2 and R.sub.4 represents a lower alkyl group, a hydroxy lower alkyl group, a cycloalkyl group or a phenyl lower alkyl group; and Y represents an ethylene group which may be substituted by lower alkyl group, a trimethylene group, a tetramethylene group, a vinylene group which may be substituted by a lower alkyl group, or ##STR3## wherein R.sub.5 represents a hydrogen atom, a lower alkyl group, a trifluoromethyl group, or a phenyl group; said X is the group shown by ##STR4## when one of said R.sub.1 and R.sub.2 is a lower alkyl group and the other is a hydrogen atom, and said Y is an ethylene group, 1/7 and the pharmacologically acceptable non-toxic salts thereof. The compounds described above are strong analgesic anti-inflammatory agents.

Nitrogen-containing heterocyclic compounds

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

##STR1## wherein R represents a hydrogen atom or a lower alkyl group; X represents a lower alkoxy group; Y represents a hydrogen atom, an amino group, or mono- or di-lower alkylamino group; Z represents a halogen atom, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a sulfamoyl group, or a lower alkylsulfamoyl group; said Y and Z may combine to form --N.dbd.N--NH--; W represents a group shown by the formula ##STR2## (wherein A represents a phenyl group, a cyclohexyl group, a furyl group, or a pyridyl group; R.sub.1, R.sub.2, and R.sub.4, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, or a phenyl group; R.sub.3 represents a lower alkyl group, a phenyl lower alkyl group, or a di-lower alkylamino lower alkyl group; R.sub.5, R.sub.6, and R.sub.7, which may be the same or different, each represents a hydrogen atom, a halogen atom, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, or a trifluoromethyl group; R.sub.8 represents a lower alkyl group; and n represents 1 or 2), a 1-ethyl-5-phenyl-2-pyrrolidinylmethyl group, a 1-ethyl-2-isoindolinylmethyl group, a 2-ethyl-1,2,3,4-tetrahydro-4-isoquinolyl group, a 2-(2-phenylpyrrolidino)ethyl group, a 2-(2-isoindolinyl)ethyl group, or a 2-(1,2,3,4-tetrahydro-2-isoquinolyl)ethyl group and the pharmaceutically acceptable nontoxic salts thereof. The compounds of this invention are strong central nervous system depressants, in particular strong antipsychotics.

N-1-Benzyl-3-pyrrolidinyl-4-dimethylamino benzamide derivatives

Novel nitrogen-containing heterocyclic compounds shown by the formula ##STR1## wherein one of R.sub.1 and R.sub.2 represents a lower alkyl group, a phenyl group, a halophenyl group, or a lower alkoxyphenyl group and the other of them represents a hydrogen atom, a lower alkyl group, or a phenyl lower alkyl group; said R.sub.1 and R.sub.2 may combine with each other to form a trimethylene group or a tetramethylene group; R.sub.3 represents a hydrogen atom, a lower alkyl group, a phenyl group, or a phenyl lower alkyl group; X represents an oxygen atom, a sulfur atom, an imino group, or a group shown by ##STR2## wherein m represents 1 or 2 and R.sub.4 represents a lower alkyl group, a hydroxy lower alkyl group, a cycloalkyl group or a phenyl lower alkyl group; and Y represents an ethylene group which may be substituted by lower alkyl group, a trimethylene group, a tetramethylene group, a vinylene group which may be substituted by a lower alkyl group, or ##STR3## wherein R.sub.5 represents a hydrogen atom, a lower alkyl group, a trifluoromethyl group, or a phenyl group; said X is the group shown by ##STR4##

Novel fused derivatives of 2-pyridones

Novel 7.alpha.-methoxy-7.beta.-heterocyclic thioacetamido-3-heterocyclic thiomethyl-.DELTA..sup.3 -cephem-4-carboxylic acid derivatives and pharmaceutically acceptable salts thereof. These compounds show high antibiotic activities against various microorganisms including gram positive and negative bacteria.

7.alpha.-METHOXY-CEPHALOSPORANIC ACID DERIVATIVES

There are disclosed novel 4-substituted amino-.alpha.-aminomethylbenzyl alcohol derivatives represented by the formula: ##STR1## wherein X represents a halogen atom; Y represents a hydrogen atom or a halogen atom; R.sub.1 represents a lower alkyl group, a carbamoyl group, a mono- or di-lower alkyl-substituted carbamoyl group, a phenyl-substituted carbamoyl group, a lower alkoxycarbonyl group, a lower alkoxy-substituted lower alkoxycarbonyl group, a phenyl-substituted lower alkoxycarbonyl group, or a cycloalkyloxycarbonyl group; and R.sub.2 represents a lower alkyl group, a cycloalkyl group, or the group shown by the ##STR2## wherein R.sub.3 represents a hydrogen atom or a lower alkyl group and R.sub.4 represents a hydrogen atom, a hydroxy group, or a lower alkoxy group and the pharmaceutically acceptable nontoxic salts thereof. These compounds are antiasthmatic agents useful for the prophylaxis and treatment of asthma.

4-Carbamoylamino-.alpha.-aminomethylbenzyl alcohol derivatives

A process of preparing a .DELTA..sup.3 -cephalosporanic acid ester derivative which comprises reacting a cephalosporanic acid sulfoxide ester derivative with thionyl halide or a phosphorous halide. The compounds prepared by the process of this invention are useful as intermediate compounds for preparing cephalosporin antibiotics and the compounds themselves are also potential antibacterials.

Process of preparing cephalosporanic acid ester derivatives

Novel indene derivatives represented by the general formula ##STR1## wherein R represents lower alkyl, phenylloweralkyl or lower cycloalkyl, and acid addition salts thereof useful as .beta.-receptor antagonists.

4-(Alkylamino-2-hydroxypropoxy)-indenes and method of use

There is disclosed a dry, stabilized oral pharmaceutical formulation containing a prostaglandin E group prepared from a lyophilized composition comprising a prostaglandin E group and at least a member selected from the group consisting of a thiol compound, dextrin, dextran, a lower alkyl cellulose, and a water-soluble salt of deoxycholic acid.

Stabilized oral prostaglandin formulation and the process for the

2-(Indenyloxymethyl) morpholine derivatives are disclosed. These derivatives are excellent in methamphetamine stereotyped increasing and antireserpine activities which are useful as antidepression agents.

2-(Indenyloxymethyl) morpholine derivatives

##STR1## wherein R represents a hydrogen atom or a lower alkyl group; X represents a lower alkoxy group; Y represents a hydrogen atom, an amino group, or a mono- or di-lower alkylamino group; Z represents a halogen atom, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a sulfamoyl group, or a lower alkylsulfamoyl group; said Y and Z may combine to form --N.dbd.N--NH--; W represents a group shown by the formula ##STR2## (wherein A represents a phenyl group, a cyclohexyl group, a furyl group, or a pyridyl group; R.sub.1, R.sub.2, and R.sub.4, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, or a phenyl group; R.sub.3 represents a lower alkyl group, a phenyl lower alkyl group, or a di-lower alkylamino lower alkyl group; R.sub.5, R.sub.6, and R.sub.7, which may be the same or different, each represents a hydrogen atom, a halogen atom, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, or a trifluoromethyl group; R.sub.8 represents a lower alkyl group; and n represents 1 or 2), a 1-ethyl-5-phenyl-2-pyrrolidinylmethyl group, a 1-ethyl-2-isoindolinylmethyl group, a 2-ethyl-1,2,3,4-tetrahydro-4-isoquinolyl group, a 2-(2-phenylpyrrolidino)ethyl group, a 2-(2-isoindolinyl)ethyl group, or a 2-(1,2,3,4-tetrahydro-2-isoquinolyl)-ethyl group and the pharmaceutically acceptable nontoxic salts thereof. The compounds of this invention are strong central nervous system depressants, in particular strong antipsychotics.

Pyrrolidinyl and piperidinyl benzamide derivatives

There is provided a process of preparing a prostaglandin E group-containing formulation by adding to a prostaglandin E group at least one additive selected from the group consisting of thiol compound, a water-soluble high molecular weight compound, and a water-soluble salt of deoxycholic acid and then subjecting the mixture to lyophilization.

Process of preparing stable prostaglandin E group-containing formulation

A novel cephalosporin derivative having at the 3-position of the cephem ring a heterocyclic thiomethyl group having a carboxy group or a sulfo group and at the 7-position of the cephem ring, an .alpha.-heterocyclic acylaminophenylacetamide group. The compounds of this invention have excellent antibacterial activity against Pseudomonas and Proteus strains of bacteria.

Cephalosporin derivatives having at the 3-position of the cephem ring a

Growing community of inventors

Tokyo, Japan

Masuo Murakami