The Upjohn Co.

Charles M Hall

John B Wright

Herbert G Johnson

Eldridge Myles Glenn

Anthony A Sinkula

Richard S Hsi

Novel compounds of the formula ##STR1## wherein X and Y are the same or different and are hydrogen, fluora, chloro, bromo, alkyl of one to six carbon atoms, inclusive, alkoxy of one to six carbon atoms, inclusive, nitro, cyano, amino, trifluoromethyl, ##STR2## wherein R.sub.1 is alkyl of one to six carbon atoms, inclusive, ##STR3## wherein R.sub.2 and R.sub.3 are the same or different and are hydrogen or alkyl of one to three carbon atoms inclusive, or CO.sub.2 Q where Q is alkyl of one to six carbon atoms, inclusive, hydrogen or a physiologically acceptable metal or amine cation; and R is hydrogen, alkyl of one to eight carbon atoms, inclusive, --CH.sub.2).sub.m phenyl wherein m is 0, 1 or 2 or (CH.sub.2).sub.n NR.sub.4 R.sub.5 wherein n is 1 or 2, and R.sub.4 and R.sub.5 are the same or different and are alkyl of one to three carbon atoms, inclusive, and a physiologically acceptable metal or amine cation; and physiologically acceptable acid addition salts thereof are formulated into pharmaceutical compositions suitable for oral, parenteral or inhalation administration which are used as prophylactic inhibitors of allergic manifestations in sensitized mammals.

Benzothiazole derivatives

Compounds represented below ##STR1## and pharmaceutical compositions thereof, the compositions including the non-substituted phenylene dioxamates are useful in the prophylactic treatment of sensitized mammals for allergy and all anaphylactic reactions of a reagin or non-reagin mediated nature.

Phenylene dioxamate esters

A process for treating inflammation locally or topically by administering a compound of the formula: ##STR1## wherein M and M' are hydrogen, hydroxy, halogen, lower alkyl of from 1 to 3 carbon atoms, lower alkoxy of from 1 to 3 carbon atoms; NH.sub.2, RNH, R'.sub.2 N where R is lower alkyl of from 1 to 3 carbon atoms or lower acyl of from 1 to 3 carbon atoms and R' is lower alkyl of from 1 to 3 carbon atoms; X, Y and Z are hydrogen, hydroxy, halogen, lower alkoxy of from 1 to 3 carbon atoms or lower acyloxy of from 1 to 6 carbon atoms, in association with appropriate pharmaceutical carriers.

Process for treating inflammation

Compounds of the formula below are useful for expanding the lumina of air passages in a mammal in need of said treatment. The compounds are also useful for treating atopic eczema and urticaria. ##STR1## wherein X and Y are the same or different and are hydrogen, fluoro, chloro, bromo, nitro, trifluoromethyl, alkyl of one to four carbon atoms, inclusive, alkoxy of one to four carbon atoms, inclusive, and cyano;

Quinoxalinones

Quinoxalinones useful for treating atopic eczema and urticaria

N-Hetero substituted dioxamic acid compounds

Compounds of the formula below are useful for expanding the lumina or air passages in a mammal in need of said treatment. The compounds are also useful for treating atopic eczema and urticaria. ##STR1## wherein X and Y are the same or different and are hydrogen, fluoro, chloro, bromo, nitro, trifluoromethyl, alkyl of one to four carbon atoms, inclusive, alkoxy of one to four carbon atoms, inclusive, and cyano;

Quinoxalinone compounds useful for expanding the lumina or air passages

Novel compounds of the formula ##STR1## wherein R is alkyl of one to eight carbon atoms, inclusive, are formulated into pharmaceutical compositions suitable for oral or parenteral administration which are used as agents to prophylactically inhibit the allergic manifestations of a sensitized mammal.

3,5-Dinitro oxanilic acid ester compounds, compositions and methods

A method of treating mammals for allergy and anaphylactic reactions of a reagin or non-reagin mediated nature which comprises administering prophylactically to said mammal an anti-allergy or anaphylactic reaction effective amount of a compound of the formula ##STR1## Novel compositions are also claimed.

Anti-allergic bis-phenylene compositions and methods of using same

Dioxamic acids and salts

Anti-allergic bis phenylene compositions and uses

Compounds of the formula ##STR1## wherein X and Y are the same or different and are hydrogen, fluoro, chloro, bromo, alkyl of one to six carbon atoms, inclusive, alkoxy of one to six carbon atoms, inclusive, nitro, cyano, amino, trifluoromethyl, ##STR2## wherein R.sub.1 is alkyl of one to six carbon atoms, inclusive, ##STR3## wherein R.sub.2 and R.sub.3 are the same or different and are hydrogen or alkyl of one to three carbon atoms inclusive, or CO.sub.2 Q where Q is alkyl of one to six carbon atoms, inclusive, hydrogen or a physiologically acceptable metal or amine cation; and R is hydrogen, alkyl of one to eight carbon atoms, inclusive, --CH.sub.2).sub.m phenyl wherein m is 0, 1 or 2 or (CH.sub.2).sub.n NR.sub.4 R.sub.5 wherein n is 1 or 2, and R.sub.4 and R.sub.5 are the same or different and are alkyl of one to three carbon atoms, inclusive, and a physiologically acceptable metal or amine cation; and physiologically acceptable acid addition salts thereof are formulated into pharmaceutical compositions suitable for oral, parenteral or inhalation administration which are used as prophylactic inhibitors of allergic manifestations in sensitized mammals.

Benzothiazolyl oxanic acids, esters and salts

Pharmaceutical composition having as the active agent a compound of the formula ##STR1## wherein R is hydrogen, a physiologically acceptable metal or amine cation and alkyl of one to eight carbon atoms inclusive, useful for preventing allergic manifestations in sensitized mammals.

Anti-allergic aminooxanilic acids and esters

A method of treating mammals for allergy and anaphylactic reactions of a reagin or non-reagin mediated nature which comprises administering prophylactically to said mammal an anti-allergy or anaphylactic reaction effective amount of a compound of the formula ##STR1## Novel compounds and compositions are also claimed.

Anti-allergic oxanil compounds

Novel chemical compounds of the formula: ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl from one to three carbon atoms, inclusive, phenyl, alkali metal, or an amine cation;

Growing community of inventors

Kalamazoo, MI, United States of America

Charles M Hall