Warner-lambert Company

Max Von Strandtmann

David T Connor

Patricia A Young

Sylvester R Klutchko

John Shavel, Jr

Marvin P Cohen

This invention is concerned with a novel process for the production of 2-substituted chromones (I) from readily available 4-methoxycoumarins. ##STR1## These compounds are useful as antiallergy agents.

Process for the production of 2-substituted chromones

The present invention is concerned with 11-oxo-1-benzoxepino[4,3-c]pyridines of Formula I: ##STR1## wherein R.sub.1 and R.sub.2 may be hydrogen, lower alkyl, cyano, carboxamido, carboxy, ethoxycarbonyl or tetrazolyl and R.sub.3 may be hydrogen, lower alkyl, halogen, hydroxy or lower alkoxy. These compounds are indicated in the management of allergic conditions such as bronchial asthma, hay fever and the like.

1-Benzoxepino[4,3-c]pyridines

There is described 3-(1H-tetrazol-5-yl)chromones having the following structural formula: ##STR1## in which R is lower alkoxy having 1 to 3 carbon atoms, aryl such as phenyl, halogen or trihalo lower alkyl. These compounds exhibit anti-allergic properties and are indicated in the treatment of allergic conditions such as hay fever and asthma.

3-(1H-Tetrazol-5-yl)chromones

The present invention relates to compounds of the formula: ##STR1## wherein R.sub.1 is hydrogen, halogen, hydroxy, lower alkoxy or lower alkyl, R.sub.2 is hydrogen or lower alkyl; R.sub.3 is hydrogen or lower alkyl. These compounds, including their corresponding pharmaceutically acceptable salts, are useful in the management of allergic conditions such as hay fever and as a prophylactic in the treatment of bronchial asthma.

(4-Oxo-4H-1-benzopyran-3-yl)aminooxoacetic acids and their derivatives

The present invention relates to 4,10-dihydro-4,10-dioxo-1H-1-benzopyrano[3,2-b]pyridine-3-carboxylic acids, salts and esters having the formula: ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, halogen, hydroxy or lower alkoxy; R.sub.2 is hydrogen, aralkyl or lower alkyl; R.sub.3 is hydrogen or lower alkyl and their pharmaceutically acceptable salts. These compounds are indicated in the management of allergic conditions such as bronchial asthma, hay fever and the like.

4,10-Dihydro-4,10-dioxo-1H-1-benzopyrano[3,2-b]pyridine-3-carboxylic

There is disclosed 4,10-dihydro-4,10-dioxo-1H-1-benzopyrano[3,2-b]pyridine-2-carboxylic acids, salts and esters of the formula: ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, halogen, hydroxy or lower alkoxy; R.sub.2 is hydrogen, aralkyl or lower alkyl; R.sub.3 is hydrogen or lower alkyl and their pharmaceutically acceptable salts. These compounds are useful in the management of allergic conditions such as bronchial asthma, hay fever and so on.

4,10-Dihydro-4,10-dioxo-1H-1-benzopyrano[3,2-b]pyridine-2-carboxylic

The present invention relates to 2-[1-imino-2-(methylsulfinyl)ethyl]phenols and 3-[1-imino-2-(methylsulfinyl)ethyl]-2-naphthalenols having the following structural formulas: ##STR1## wherein X is hydrogen, lower alkyl, halogen, lower alkoxy or hydroxy; Y is hydrogen, lower alkyl or cycloalkyl. These compounds exhibit antibacterial activity, particularly against gram-positive bacteria, and are useful in the treatment of bacterial infections caused by these organisms.

2-[1-Imino-2-(methylsulfinyl)ethyl]phenols and

The present invention relates to [2-(4-oxo-4H-1-benzopyran-2-yl)ethenyl]benzonitrile and benzoic acids having the following structural formula: ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are hydrogen, lower alkyl, halogen or lower alkoxy, and A is COOH or CN. The compounds of this invention exhibit anti-allergy properties and are indicated in the management of allergic manifestations such as bronchial asthma.

[2-(4-Oxo-4H-1-benzopyran-2-yl)ethenyl]benzonitriles and benzoic acids

The present invention relates to substituted [4-oxo-4H-1-benzopyran-2-yl]cyclopropane carboxylic acids and esters having the following structural formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are hydrogen, alkyl, lower alkoxy, phenyl or when R.sub.1 and R.sub.2 are hydrogen, R.sub.3 and R.sub.4 taken together form an additional aromatic ring and A is hydrogen or ethyl. The compounds of this invention exhibit anti-allergy properties and are indicated in the management of allergic manifestations such as bronchial asthma.

Substituted (4-oxo-4H-1-benzopyran-2-yl)cyclopropane carboxylic acids

There is disclosed 2,3-dihydro-3-(2-pyridinyl)-4H-1-benzopyran-4-one N-oxides of the formula: ##STR1## in which R.sub.1 is hydrogen, halogen, lower alkyl, hydroxy, lower alkoxy or amino; R.sub.2 is hydrogen or --CH.sub.2 OH. These compounds are indicated in the treatment of gastric ulcers.

2,3-Dihydro-3-(2-pyridinyl)-4H-1-benzopyran-4-one N-oxides

Compounds of the formula: ##STR1## are disclosed wherein X is NH, O or S and the tautomers thereof when X is nitrogen, and Y is hydrogen, lower alkyl, hydroxy, lower alkoxy, chloro, bromo or aryl. These compounds are useful in the management of allergic manifestations such as bronchial asthma.

Heterocyclic annelated 1-benzoxepin-5-ones

There are disclosed 7-substituted-9-oxoxanthene-2-carboxaldehydes of the formula: ##STR1## in which R is lower alkoxy or hydroxy. These compounds are indicated in the management of allergic manifestations such as, for example, bronchial asthma or hay fever.

7-Substituted-9-oxoxanthene-2-carboxaldehydes

Compounds of the formula: ##STR1## are disclosed. In this structural formula X is ##STR2## and Y is hydrogen, lower alkyl, hydroxy, lower alkoxy, chloro, bromo or aryl. Included within the scope of this invention are tautomers of the above compound. These compounds and their tautomers are indicated in the management of allergic manifestations such as bronchial asthma.

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Rockaway, NJ, United States of America

Max Von Strandtmann