Fujisawa Pharmaceutical Company, Ltd.

Research Institute for Production Developement

Toko Yakuhin Kogyo Co., Ltd.

Hoei Pharmaceutical Co., Ltd.

Suminori Umio

Ikuo Ueda

Masaaki Matsuo

Yoshinari Sato

Shizuo Maeno

Masakazu Kobayashi

Osamu Nakaguti

Takuzo Kamishita

Takahiro Yabuuchi

Yasuhiro Mine

Toshiaki Kamimura

Shizuo Kozasa

Benzothiazolone Derivatives represented by the formula: ##STR1## in which X is halogen, A is alkylene and R is alkoxy, amino, substituted amino, carboxyalkyl or carboxyalkylene, which are useful as antiallergic or antiinflammatory agents.

Antiallergic and antiinflammatory benzothiazolinone derivatives

This invention relates to an antifungal composition containing pyrrolnitrin and an antimycotic imidazole compound as active ingredients.

Antifungal composition employing pyrrolnitrin in combination with an

Chromone compounds having the structure ##STR1## wherein R is aryl, substituted aryl, thienyl, furyl or pyridyl, Y is hydroxy (lower) alkylene, R.sub.1 is hydrogen, lower alkyl, aryl, substituted aryl or a heterocyclic group, R.sub.2 is hydrogen or lower alkoxy, Y.sub.1 is lower alkylene or hydroxyl (lower) alkylene, Z is oxygen or sulfur and R.sub.3 is hydrogen, lower alkyl, aryl, substituted aryl, or ar (lower) alkyl have anti-allergic activity and are useful in the treatment of asthma. Compounds of the structure [I] are prepared by reacting ##STR2## wherein Y' is hydroxy (lower) alkylene whose hydroxy group is optimally protected or a reactive derivative of [II] with a carboxylic acid of the formula R--COOH in the presence of a basic catalyst. The resulting compound is then reacted with an acid. Compounds of the structure [I'] are prepared by reacting the compound ##STR3## with the compound X--Y.sub.1 '--Z--R.sub.3 ' wherein X is an acid residue, Y' is lower alkylene or hydroxy (lower) alkylene whose hydroxy group is optionally protected by a protective group, R.sub.3 ' is hydrogen, lower alkyl, aryl, substituted aryl, or ar (lower) alkyl and Z is as defined above. When R.sub.3 ' is hydrogen, --Z--R.sub.3 ' is optionally protected by a protective group. The resultant compound is subjected to an elimination reaction when Y' is a protected group or when --Z--R.sub.3 ' is protected to split off the protective group.

Chromone compounds and preparation thereof

Chromone compounds having the structure ##STR1## wherein R is aryl, substituted aryl, thienyl, furyl or pyridyl, Y is hydroxy (lower) alkylene, R.sub.1 is hydrogen, lower alkyl, aryl, substituted aryl or a heterocyclic group, R.sub.2 is hydrogen or lower alkoxy, Y.sub.1 is lower alkylene or hydroxyl (lower) alkylene, Z is oxygen or sulfur and R.sub.3 is hydrogen, lower alkyl, aryl, substituted aryl, or ar(lower)alkyl have anti-allergic activity and are useful in the treatment of asthma. Compounds of the structure [I] are prepared by reacting ##STR2## wherein Y' is hydroxy (lower) alkylene whose hydroxy group is optimally protected or a reactive derivative of [II] with a carboxylic acid of the formula R--COOH in the presence of a basic catalyst. The resulting compound is then reacted with an acid. Compounds of the structure [I] are prepared by reacting the compound ##STR3## with the compound X--Y.sub.1 '--Z--R.sub.3 ' wherein X is an acid residue, Y' is lower alkylene or hydroxy (lower) alkylene whose hydroxy group is optionally protected by a protective group, R.sub.3 ' is hydrogen, lower alkyl, aryl, substituted aryl, or ar(lower)alkyl and Z is defined above. When R.sub.3 ' is hydrogen, --Z--R.sub.3 ' is optionally protected by a protective group. The resultant compound is subjected to an elimination reaction when Y' is a protected group or when --Z--R.sub.3 ' is protected to split off the protective group.

Chromone compounds

Chromone derivatives of the formula: ##STR1## wherein R.sup.1 is alkoxy, an N,S-containing heterocyclic group or aryloxy in which heterocyclic group may be substituted with halogen or acyl, and aryl may be substituted with amino, alkylamino, acylamino, nitro or alkylenedioxy; R.sup.2 is alkylene; R.sup.3 is hydroxy, alkoxy or a group of the formula ##STR2## in which R.sup.4 is hydrogen, R.sup.5 is hydroxy or amino or R.sup.4 and R.sup.5 means taken together with the adjacent nitrogen atom, piperazinyl substituted with alkyl or hydroxyalkyl; provided that when R.sup.3 is hydroxy or alkoxy, R.sup.1 is an N,S-containing heterocyclic group or aryloxy in which heterocyclic group is substituted with halogen or acyl, and aryl is substituted with amino, alkylamino, acylamino, nitro or alkylenedioxy, and nontoxic, pharmaceutically acceptable salt thereof. These compounds are useful as anti-allergic agents.

Chromone derivatives

This invention relates to novel 1-alkanesulfonyloxyalkyl-2-alkyl-3-diphenylmethylenepyrrolidines, their acid addition salts and preparation thereof, having anticolinergic activity.

1-Alkanesulfonyloxyalkyl-2-alkyl-3-diphenylmethylenepyrrolidines

Chromone compounds having the structure ##SPC1## Wherein R is aryl, substituted aryl, thienyl, furyl or pyridyl, Y is hydroxy(lower)alkylene, R.sub.1 is hydrogen, lower alkyl, aryl, substituted aryl or a heterocyclic group, R.sub.2 is hydrogen or lower alkoxy, Y.sub.1 is lower alkylene or hydroxyl(lower)alkylene, Z is oxygen or sulfur and R.sub.3 is hydrogen, lower alkyl, aryl, substituted aryl, or ar(lower)alkyl have anti-allergic activity and are useful in the treatment of asthma. Compounds of the structure [I] are prepared by reacting ##SPC2## Wherein Y' is hydroxy(lower)alkylene whose hydroxy group is optimally protected or a reactive derivative of [II] with a carboxylic acid of the formula R--COOH in the presence of a basic catalyst. The resulting compound is then reacted with an acid. Compounds of the structure [I'] are prepared by reacting the compound ##SPC3## With the compound X--Y.sub.1 '--Z--R.sub.3 ' wherein X is an acid residue, Y' is lower alkylene or hydroxy(lower)alkylene whose hydroxy group is optionally protected by a protective group, R.sub.3 ' is hydrogen, lower alkyl, aryl, substituted aryl, or ar(lower)alkyl and Z is as defined above. When R.sub.3 ' is hydrogen, --Z--R.sub.3 ' is optionally protected by a protective group. The resultant compound is subjected to an elimination reaction when Y' is a protected group or when --Z--R.sub.3 ' is protected to split off the protective group.

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Kawanishi, Japan

Suminori Umio