Bristol-Myers Company

Aldo A Algieri

Ronnie R Crenshaw

Robert F Farney

The present invention relates to novel intermediates of the formula ##STR1## wherein R.sup.1 is hydrogen or lower alkyl and R is ##STR2## --CH.sub.2 OH or --CH.sub.2 X in which X is a conventional leaving group and Y is lower alkyl and the use thereof in a process for the preparation of certain histamine H.sub.2 -antagonists.

Chemical intermediates and process

Compounds of the formula ##STR1## wherein R.sup.12 is a leaving group, Z is S, O or CH.sub.2 and A is a phenyl, furyl, thienyl or pyridyl ring substituted by a ##STR2## moiety, in which R.sup.8 and R.sup.9 are various substituents or, when taken together with the nitrogen, may be a specified heterocyclic ring, are intermediates in the preparation of histamine H.sub.2 -antagonist anti-ulcer agents of the formula ##STR3## in which R.sup.1 and R.sup.2 are any of several specified substituents.

Substituted 3-cyclobutene-1,2-diones as anti-ulcer agents

Histamine H.sub.2 -antagonists of the formula: ##STR1## wherein m is an integer of from zero to 2, inclusive;

2,5-disubstituted-4(3H)-pyrimidones having histamine H.sub.2 -receptor

Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.1 are as defined herein, and their nontoxic pharmaceutically acceptable salts are novel anti-ulcer agents which are prepared by ring closure of a substituted ethanediimidamide of the formula ##STR2##

Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H.sub.2

Certain 1-(substituted amino)-2-(amino or substituted amino)cyclobutene-3,4-diones are potent histamine H.sub.2 -antagonists useful in the treatment of peptic ulcers.

3-cyclobutene-1,2-dione intermediates

Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.1 are as defined herein, and their nontoxic pharmaceutically acceptable salts, hydrates and solvates are novel anti-ulcer agents which are prepared by ring closure of a substituted ethanediimidamide of the formula ##STR2##

Ethanediimidamide intermediates

Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.1 are as defined herein, and their nontoxic pharmaceutically acceptable salts, hydrates and solvates are novel anti-ulcer agents which are prepared by ring closure of a substitutted ethanediimidamide of the formula ##STR2##

Substituted amino alkyl pyridyl ethanediimidamides

Substituted 1,2-diaminocyclobutene-3,4-diones

Pyridine derivatives of 1,2-diaminocyclobutene-3,4-diones

Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.1 are as defined herein, and their nontoxic pharmaceutically acceptable salts, hydrates and solvates are novel anti-ulcer agents which are prepared by ring closure of a substituted ethanediimidamide of the formula ##STR2## .

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Fayetteville, NY, United States of America

Aldo A Algieri