3,4-dihydrobenzopyran derivatives and medicinal uses thereof

A pharmaceutical composition for the treatment of peptic ulcer, cough or sputum, said composition comprising an amount effective to treat peptic ulcer, cough or sputum of a 3,4-dihydrobenzopyran derivative of the formula ##STR108## wherein R.sup.1 and R.sup.4 each represent a hydrogen atom or a lower alkyl group;

• R.sup.2 represents a hydrogen atom, a halogen atom, a lower alkoxyl group or a lower alkenyloxy group;
• R.sup.3 represents a hydrogen atom, a lower alkyl group or a lower alkoxyl group;
• R represents a group of the following formula (2) ##STR109## wherein n represents an integer of 0, 1 or 2;
• X.sup.2 represents a methylene group or a carbonyl group;
• when X.sup.2 represents a methylene group, R.sup.6 represents a lower alkyl group or a lower alkyl group substituted by a hydroxyl group, ##STR110## and when X.sup.2 represents a carbonyl group, R.sup.6 represents ##STR111## where p and q each represent an integer of 0 to 4;
• X.sup.3 represents a methylene group or a carbonyl group;
• Q.sup.1 represents a nitrogen atom (.dbd.N--), a carbon atom ##STR112## where R.sup.111 represents a hydrogen atom, a lower alkoxyl group, a halogen atom, a di-lower alkylamino group or a nitro group;
• R.sup.71, R.sup.81, R.sup.91 and R.sup.101 each represent a hydrogen atom or a lower alkoxyl group;
• Q.sup.2 represents a nitrogen atom (.dbd.N--), a substituted carbon atom ##STR113## where R.sup.112 represents a hydrogen atom, a lower alkoxyl group, a halogen atom, a di-lower alkylamino group or a nitro group;
• and R.sup.72, R.sup.82, R.sup.92 and R.sup.102 each represent a hydrogen atom or a lower alkoxyl group;
• or a pharmacologically acceptable salt thereof and a pharmaceutically acceptable diluent or carrier.

A pharmaceutical composition for the treatment of peptic ulcer which comprises an effective amount to treat peptic ulcer of a 3,4-dihydrobenzopyran derivative of the formula ##STR114## wherein R.sup.1 and R.sup.4 each represent a hydrogen atom or a lower alkyl group;

• R.sup.2 represents a hydrogen atom, a halogen atom, a lower alkoxyl group or a lower alkenyloxy group;
• R.sup.3 represents a hydrogen atom, a lower alkyl group or a lower alkoxyl group;
• n represents an integer of 0, 1 or 2;
• R.sup.61 represents ##STR115## where p represents an integer of 0 to 4, X.sup.3 represents a methylene group or a carbonyl group, Q.sup.1 represents a nitrogen atom (.dbd.N--), a carbon atom ##STR116## where R.sup.111 represents a hydrogen atom, a lower alkoxyl group, a halogen atom, a di-lower alkylamino group or a nitro group;
• R.sup.71, R.sup.81, R.sup.91 and R.sup.101 each represent a hydrogen atom or a lower alkoxyl group;
• or a pharmacologically acceptable salt thereof and a pharmaceutically acceptable diluent or carrier.

A pharmaceutical composition useful as an antitussive and/or expectorant which comprises as an active ingredient an amount effective as an antitussive and/or expectorant of 3,4-dihydrobenzopyran derivative of the formula ##STR117## wherein R.sup.1 and R.sup.4 each represent a hydrogen atom or a lower alkyl group;

• R.sup.2 represents a hydrogen atom, a halogen atom, a lower alkoxyl group or a lower alkenyloxy group;
• R.sup.3 represents a hydrogen atom, a lower alkyl group or a lower alkoxyl group;
• n-represents an integer of 0, 1 or 2;
• X.sup.2 represents a methylene group or a carbonyl group;
• when X.sup.2 represents a methylene group, R.sup.63 represents a lower alkyl group or a lower alkyl group substituted by a hydroxyl group, ##STR118## and when X.sup.2 represents a carbonyl group, R.sup.63 represents ##STR119## where q represents an integer of 0 to 4, Q.sup.1 represents a nitrogen atom (.dbd.N--), a carbon atom ##STR120## where R.sup.111 represents a hydrogen atom, a lower alkoxyl group, a halogen atom, a di-lower alkylamino group or a nitro group;
• R.sup.71, R.sup.81, R.sup.91 and R.sup.101 each represent a hydrogen atom or a lower alkoxyl group;
• Q.sup.2 represents a nitrogen atom (.dbd.N--), a carbon atom ##STR121## where R.sup.112 represents a hydrogen atom, a lower alkoxyl group, a halogen atom, a di-lower alkylamino group or a nitro group;
• R.sup.72, R.sup.82, R.sup.92 and R.sup.102 each represent a hydrogen atom or a lower alkoxyl group;
• or a pharmacologically acceptable salt thereof and a pharmaceutically acceptable diluent or carrier.

A method for treating peptic ulcer, cough or sputum, which comprises administering an effective amount to treat peptic ulcer, cough or sputum, of a 3,4-dihydrobenzopyran derivative of the formula ##STR122## wherein R.sup.1 and R.sup.4 each represent a hydrogen atom or a lower alkyl group;

• R.sup.2 represents a hydrogen atom, a halogen atom, a lower alkoxyl group or a lower alkenyloxy group;
• R.sup.3 represents a hydrogen atom, a lower alkyl group or a lower alkoxyl group;
• R represents a group of the following formula (2) ##STR123## wherein n represents an integer of 0, 1 or 2;
• X.sup.2 represents a methylene group or a carbonyl group;
• when X.sup.2 represents a methylene group, R.sup.6 represents a lower alkyl group or a lower alkyl group substituted by a hydroxyl group, ##STR124## and when X.sup.2 represents a carbonyl group, R.sup.6 represents ##STR125## where p and q each represent an integer of 0 to 4;
• X.sup.3 represents a methylene group or a carbonyl group;
• Q.sup.1 represents a nitrogen atom (.dbd.N--), a carbon atom ##STR126## where R.sup.111 represents a hydrogen atom, a lower alkoxyl group, a halogen atom, a di-lower alkylamino group or a nitro group;
• R.sup.71, R.sup.81, R.sup.91 and R.sup.101 each represent a hydrogen atom or a lower alkoxyl group;
• Q.sup.2 represents a nitrogen atom (.dbd.N--), a carbon atom ##STR127## where R.sup.112 represents a hydrogen atom, a lower alkoxyl group, a halogen atom, a di-lower alkylamino group or a nitro group;
• and R.sup.72, R.sup.82, R.sup.92 and R.sup.102 each represent a hydrogen atom or a lower alkoxyl group;
• or a pharmacologically acceptable salt thereof.