Fujisawa Pharmaceutical Company, Ltd.

Shizuo Maeno

Suminori Umio

Ikuo Ueda

Masaaki Matsuo

Yoshinari Sato

Takashi Kamiya

Yoshihiko Kitaura

Bicyclomycin derivatives having the general formula: ##STR1## wherein R.sub.I is ##STR2## R.sub.II and R.sub.III are hydrogens or aliphatic, R.sub.IV is hydrogen, aliphatic, acyl, or aliphatic heterocyclic, and Z is ##STR3##

Bicyclomycin derivatives

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

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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Osaka, Japan

Shizuo Maeno