Takeda Chemical Industries, Inc.

Takeda Pharmaceutical Company Limited

Hamari Chemicals, Ltd.

Toshio Miyawaki

Satoshi Yamamoto

Mitsuru Shiraishi

Mitsuo Numata

Masayoshi Yamaoka

Isao Minamida

Takehiko Naka

Shinji Terao

Zen-ichi Terashita

Hideto Fukushi

Isao Mimamida

Akira Morimoto

Michihiko Ochiai

Naoyuki Kanzaki

Masami Kusaka

Hirotomo Masuya

Sadayuki Maeda

Hiroshi Shimadzu

Marvin A Motsenbocker

Yasuhiko Kawano

Tatsunori Sato

Yoshio Imashiro

Takahito Hara

Mitsura Shiraishi

Provided are a novel chiral iridium(III) complex; and a method for producing optically active 2-substituted-1,2,3,4-tetrahydroquinolines from 2-substituted-quinolines with the use of the chiral iridium(III) complex through a more economical and easy production process. The disclosed method for producing optically active 2-substituted-1,2,3,4-tetrahydroquinolines comprises reducing a quinoline compound represented by formula [I]: in the presence of a hydrogen donor compound and an iridium (III) complex having a chiral prolinamide compound as a ligand to give an optically active 2-substituted-1,2,3,4-tetrahydroquinoline represented by formula [II]: 

Method for producing optically active tetrahydroquinolines

The present invention provides a compound represented by the general formula: [wherein Ring A represents an optionally substituted 5- to 8-membered ring, Ring B represents a further optionally substituted 4- to 10-membered ring, Ring C represents a further optionally substituted benzene ring, Xrepresents carbon atom, Xrepresents a carbon atom, an oxygen atom, etc., W represents a nitrogen atom, etc., Yrepresents a group represented by the formula CRR(wherein Rrepresents a hydrogen atom, a cyano group, a nitro group, etc., and Rrepresents a hydrogen atom, a cyano group, a nitro group, etc., respectively), Yrepresents a group represented by the formula CRR(wherein Rrepresents a hydrogen atom, a cyano group, a nitro group, etc., and Rrepresents a hydrogen atom, a cyano group, a nitro group, etc., respectively), etc., and Rrepresents an electron-withdrawing group, respectively. The formularepresents a single bond or a double bond] or a salt thereof, which is useful as an androgen receptor modulator.

Fused benzene derivative and use

The present invention provides compounds and medicines effective for prophylaxis and therapy of various diseases by controlling or inhibiting cell-adhesion. Especially, the compounds of this invention perform platelet aggregation action without remarkable elongation of hemorrhagic period and can be used as a safe and long-acting antithrombotic drug as compared with known substances showing the same activity. Compounds of this invention are piperazinones of the formula ##STR1##

Piperazinones, their production and use

There is disclosed a novel phenothiazine derivative of the general formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different and are a C.sub.1-6 alkyl group and at least one of them has as a substituent a group which can react with amino group, thiol group or carboxyl group, and X.sup.- is a counter ion of the phenazathionium. Their production and the intermediates used in the production are also disclosed. The compound (I) is a derivative of methylene blue and is applicable to photodynamic therapy of cancer or immunoassays utilizing chemiluminescence.

Phenothiazine derivatives, their production and use

A compound of the formula: ##STR1## wherein R.sup.1 represents hydrogen or an alkyl group, X represents oxygen or sulfur or a group of formula -NR.sup.2 (where R.sup.2 is hydrogen or an alkyl group and in the case of alkyl, it may form a ring jointed with R.sup.1), and Y represents acetoxy group or a group of formula -SR.sup.3 (where R.sup.3 is a nitrogen-containing heterocyclic group), or a pharmaceutically acceptable salt thereof, is found to have a broad antimicrobial spectrum and, in particular, effective against gram-negative bacteria including Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris, Proteus morganii, as well as gram positive ones. Thus, these compounds may be used for antimicrobial agents in therapeutical purposes.

Cephalosporin derivatives

A compound of the formula: ##STR1## wherein R.sup.1 represents hydrogen or an alkyl group, X represents oxygen or sulfur or a group of formula --NR.sup.2 (where R.sup.2 is hydrogen or an alkyl group and in the case of alkyl, it may form a ring jointed with R.sup.1), and Y represents acetoxy group or a group of formula --SR.sup.3 (where R.sup.3 is a nitrogen-containing heterocyclic group), or a pharmaceutically acceptable salt thereof, is found to have a broad antimicrobial spectrum and, in particular, effective against gram-negative bacteria including Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris, Proteus morganii, as well as gram positive ones. Thus, these compounds may be used for antimicrobial agents in therapeutical purposes.

A halogenoacetyl group is removed from a halogenoacetyl amino compound in a short period of reaction time by reacting the halogenoacetyl amino compound with an N-substituted dithiocarbamic acid or a salt thereof.

Method for removing protective groups

7-Alpha-(2-aminothiazole)-acetamido-cephalosporins

Novel cephalosporin compounds of the formula ##STR1## wherein R.sup.1 is an acyl group and R.sup.2 is an alkylene group which may be substituted with a lower alkoxyl group, or pharmaceutically acceptable salt thereof, have strong inhibitory actions on broad spectra of gram-positive and gram-negative bacteria and, particularly against Esherichia coli and Klebsiella pneumoniae. Thus, the compounds are useful as therapeutic agent for various bacterial infections of animals including human beings.

3-(Morpholinoalkoxyiminomethyl)cephem compounds

A 3-hydroxymethylcephalosporin which is not protected at the carboxyl group can be directly oxidized with a hexavalent chromium compound to give in good yield a lactol type cephalosporin represented by the general formula: ##SPC1## Wherein R.sup.1 is hydrogen or an alkoxy group and R.sup.2 is an acylamino, or imido group. The resulting compounds are very useful and important as intermediates for preparing, e.g. 3-alkoxyiminomethyl cephalosporins.

Process for producing lactol-type cephalosporins

Growing community of inventors

Hyogo, Japan

Toshio Miyawaki