Taisho Pharmaceutical Co., Ltd.

Other

Kuraray Co., Ltd.

Takehiro Amano

Fumie Sato

Tohru Tanami

Jun Goto

Naoya Ono

Kazuya Kameo

Masaru Mutoh

Kensei Yoshikawa

Jiro Sawada

Yutaka Ohuchi

Tatsuhiko Sano

Takashi Nishida

Yoshiji Fujita

Manzo Shiono

Michihiro Ishiguro

Michitada Sasajima

Katsuaki Miyaji

Kaoru Sota

Masami Goi

Kazuto Sekiuchi

Toshihisa Ogawa

Susumu Otomo

Shoichi Ito

Jozi Nakagami

Tomomichi Yoshida

Yoshihiro Migita

Yukinari Kumazawa

Jinsaku Sakakibara

Tadashi Eguchi

Masahiro Hasegawa

Yoshinori Shiobara

Seiichi Takano

A cis-olefin of the formula: R,&mdash;CH&boxH;CH&mdash;R,is prepared by reducing an alkyne of the formula: R,&mdash;C&equiv;C&mdash;R,with formic acid in the presence of a palladium catalyst. R,and R,are independently selected from the group consisting of a hydrogen atom, ester group, substituted silyl group, carboxyl group, cyano group, aliphatic C1-C20 hydrocarbon group, and phenyl group. The cis-olefin which is a useful intermediate for the synthesis of fine chemicals is selectively produced in high yields.

Preparation of cis&mdash;olefins

Process for the preparation of E-prostaglandins

Prostaglandin E.sub.1 analogues

A prostaglandin derivative represented by the formula: ##STR1## wherein X is halogen atom R.sup.1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R.sup.2 is a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkylmethyl group having 4 to 10 carbon atoms or a cycloalkylethyl group having 5 to 12 carbon atoms, or a salt thereof, which has an excellent lowering action of intraocular pressure and improving actions of renal diseases, ischemic heart diseases and heart failure.

Prostaglandin derivatives

A process for preparing erythromycin A oxime or a salt thereof which comprises reacting erythromycin A with hydroxylamine using an acid, is disclosed. Erythromycin A oxime and the salts thereof are useful as intermediates for the synthesis of macrolide antibiotics.

Process for preparing erythromycin A oxime or a salt thereof

Novel benzo[.alpha.]phenazine derivatives of the formula ##STR1## wherein R.sup.1 is hydrogen, halogen, methyl, hydroxyl or alkoxy, R.sup.2 is --COOR.sup.5 (wherein R.sup.5 is hydrogen, straight or branched chain alkyl, cycloalkyl having 3-6 carbon atoms, benzyl or phenyl) or ##STR2## wherein R.sup.6 and R.sup.7 are the same or different and are each hydrogen or lower alkyl, or R.sup.6 and R.sup.7 together with the nitrogen atom to which they are attached form pyrrolidine or piperidine), R.sup.3 and R.sup.4 are the same or different and are each hydrogen or lower alkyl, and n is an integer of 2 or 3, and the salts thereof are disclosed. These compounds have antitumor activity in mammals.

Benzo[.alpha.]phenazine antitumor agents

A process for producing 1-(p-prenylphenyl)ethanol, which comprises reacting p-chloroprenylbenzene with magnesium at a temperature between 100.degree. C. and 150.degree. C. to form a Grignard reagent, and then reacting it with acetaldehyde.

Process for producing 1-(p-prenylphenyl)ethanol

A process for producing an .alpha.-arylalkanoic acid ester represented by the general formula ##STR1## wherein Ar represents an aryl group which may optionally be substituted, and R.sup.1 and R.sup.2, independently from each other, represent a lower alkyl group, which comprises reacting a Grignard reagent prepared from an aryl halide of the general formula

Process for producing .alpha.-arylalkanoic acid ester

A novel carboxylic acid ester having the following general formula ##STR1## wherein R is alkoxyalkyl having 2 to 6 carbon atoms, cycloalkyl having 5 or 6 carbon atoms, tetrahydrofurfuryl, or alkyl having 1 to 6 carbon atoms optionally substituted with 1 or 2 hydroxyl groups, is a useful anti-inflammatory and analgesic agent.

Esters of the carboxylic acid

A novel thiazolidine derivative having the following general formula ##STR1## wherein R.sup.1 and R.sup.2 are each lower alkyl having 1 to 3 carbon atoms, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached form a heterocyclic ring selected from the group consisting of morpholino, piperazino, piperidino and pyrrolidino, or said heterocyclic ring substituted with 1 or 2 methyl groups, and the pharmaceutically acceptable salts thereof are useful immunomodulators.

4-Carboxy-2-acetamido thiazolidine derivatives

2-(p-prenylphenyl)propionic acid and pharmaceutically acceptable salts thereof are disclosed. They exhibit anti-inflammatory and analgesic activity with low gastrointestinal action.

2-(p-Prenylphenyl)propionic acid

Growing community of inventors

Tokyo, Japan

Takehiro Amano