Dainippon Ink and Chemicals, Incorporated

Shigenori Nakanishi

Hidetsugu Takagaki

Masayoshi Abe

Nobuyuki Kimura

Yasuo Aoki

Akihide Koda

Mitsuru Sakai

Michihiro Watanabe

Yasuyuki Tanaka

Yoshiyuki Sano

Osamu Misumi

Shinobu Yamaguchi

Hiromi Ohki

Yoriko Yonehara

Keiji Yamazaki

Yuuko Nakata

Kazuyuki Takeuchi

An object is to provide: novel quinolinone glycosides which are useful as medicines; processes for producing the quinolinone glycosides; intermediates for synthesis; and medicines, and particularly anti-allergic agents, which comprise the quinolinone glycoside as an active ingredient. The object is achieved by: a quinolinone glycoside or a physiologically acceptable salt thereof; processes for producing this quinolinone glycosides; intermediates for synthesis; and medicines, and particularly anti-allergic agents, which comprise the quinolinone glycoside as an active ingredient; the quinolinone glycoside being expressed by general formula (I):

Quinolinone glycoside, production process, and anti-allergic agent

The present invention offers 7-aminoquinolinone derivatives, physiologically acceptable salts thereof, anti-allergic agents having as an active ingredient a 7-aminoquinolinone derivative or physiologically acceptable salt thereof, and 7-nitroquinolinone derivatives, wherein the 7-aminoquinolinone derivative is expressed by the following general formula (I): ##STR1## wherein R.sub.1 is a hydrogen atom or an alkyl group;

Quinolinone derivative and anti-allergic agent with said quinolinone

The present invention offers a safe and effective drug for heart diseases and a safe and effective method for treating heart diseases such as ischemic heart disease and cardiac arrhythmia. The method comprises administering a pathologically effective amount of a benzopyran derivative expressed by the following general formula (I): ##STR1## wherein R.sup.1 is an alkyl group or an alkenyl group, R.sup.2 is a hydrogen atom, an alkyl group, an alkyl group having at least one hydroxyl group, an alkenyl group, an acyl group or a glycosyl group; or physiologically acceptable salts thereof.

Benzopyran derivative and method for treating heart disease using this

Chalcone derivatives having at least one tetrahydropyranyloxy group is disclosed. Typically, the compounds are represented by general formula (I) ##STR1## wherein X and X' each represent a tetrahydropyranyl group, R and R', which are then same or different, each represent an alkyl group or a hydrogen atom, n and n' each are an integer of from 0 to 5, m and m' each are integers of from 0 to 5, provided that n+n' is 1 or more, and that n+m is an integer of from 0 to 5 and n'+m' is an integer of from 0 to 5. Also, disclosed are processes for producing the chalcone derivatives starting from acetophenone or its derivative and benzaldehyde or its derivative at least one of which has at least one tetrahydropyranyloxy group. Further, disclosed is 2,3,4,2',4'-pentahydroxychalcone.

Chalcone derivatives and process for producing the same

Disclosed are steroid compounds represented by general formula (I) ##STR1## wherein X and W together as &gt;W-X represent a carbonyl group (&gt;C.dbd.O) or a hydroxymethylene group (&gt;CH(OH)), the hydroxy moiety of the hydroxymethylene group being of .beta.-arrangement, and OR.sup.1 and OR.sup.2 independently represent an ester residue, and Y and Z together as --Y--Z-- represent a --(PpSe)CH--CH.sub.2 -- group where Pp represent a phenyl group or a 2-pyridyl group, or Y and Z each represent an ethenylene group or a 1-bromoethylene group. Also disclosed is a process of preparing the compound (I) includes reacting 6.beta., 9.alpha.-difluoro-5.alpha.,17.alpha.,21-trihydroxypregna-3,11,20-trione-17 ,21-diesters or 6.beta.,9.alpha.-difluoro-5.alpha.,11.beta.,17.alpha.,21-tetrahydroxypregn a-3,20-dione-17,21-diesters as starting compound with an organic selenenyl halide selected from the group consisting of 2-pyridylselenenyl chloride, 2-pyridylselenenyl bromide, phenylselenenyl chlolride and phenylselenenyl bromide. Further disclosed is a process of preparing 2-bromo-6.beta.,9.alpha.-difluoro-11.beta.,17.alpha.,21-trihydroxy-1,4-pre gnadien-3,20-di-one-17,21-diester represented by general formula (VII) ##STR2## wherein OR.sup.1 and OR.sup.2 independently represent an ester residue, which comprises reacting with hydrogen chloride, or with thionyl chloride in the presence of a basic substance, the compound (V), and optionally reducing with a reducing agent when &gt;W-X represents a carbonyl group.

Steroid compounds and process of preparing the same

A novel process for preparing a steroid of the following formula (to be referred to as compound .circle.13 ) is provided. ##STR1## This compound is known to have marked anti-inflammatory and anti-rheumatoid arthritic activity with very much reduced side effects on humans, such as weight loss, sodium retention, potassium loss and adrenal and pituitary inhibition which are observed in many steroids. The process is characterized in that starting from hydrocortisone, it can produce the desired compound .circle.13  at low cost and that it goes through the following two novel compounds (I) and (II) as intermediates. ##STR2## In the above formulae, &gt;W--X represents &gt;C.dbd.O or &gt;CH--OH, &gt;Y--Z-- represents &gt;C.dbd.CH-- or ##STR3## Q represents a hydrogen or bromine atom, and OR.sup.1 and OR.sup.2 are identical or different and each represents an acyloxy group or a sulfuric or phosphoric acid ester residue.

Process for preparation of steroids

Growing community of inventors

Sakura, Japan

Shigenori Nakanishi