American Home Products Corporation

Dieter H Klaubert

John H Sellstedt

Stanley Charles Bell

Charles J Guinosso

David A Shriver

Anthony F Kreft, Iii

Richard W Rees

Thomas W Pattison

John M Sellstedt

A novel process for producing a 1-H-tetrazole-5-thiol of the formula: ##STR1## in which R.sup.1 is hydrogen; lower alkyl; lower alkyl substituted with a carboxylic acid, a carboxylic acid lower alkyl ester, or an hydroxy group; phenyl or phenyl substituted with a halogen, a lower alkyl group, or a lower alkoxy group; benzyl or benzyl substituted with a halogen, a lower alkyl group, or 1-3 alkoxy groups of 1-3 carbon atoms; or trichloroethyl, which process comprises:

Process for preparing 1-H-tetrazole-5-thiols

A novel process for producing a 1-H-tetrazole-5-thiol of the formula ##STR1## in which R.sup.1 is hydrogen; lower alkyl; lower alkyl substituted with a carboxylic acid, a carboxylic acid lower alkyl ester, or an hydroxy group; phenyl or phenyl substituted with a halogen, a lower alkyl group, or a lower alkoxy group; benzyl or benzyl substituted with a halogen, a lower alkyl group, or 1-3 alkoxy groups of 1-3 carbon atoms; or trichloroethyl, which process comprises:

Process for preparing 1-H-tetrazole-5-thiols and intermediate compounds

2,6-Diaminobenzonitriles, useful in the production of N-(2-cyano-3-substituted or unsubstituted amino-phenyl)oxamate and N-(2-cyano-3-substituted or unsubstituted amino-phenyl)tetrazole-5-carboxamide antiallergy and antisecretory agents, are prepared by sequential displacement of the fluoro substituents from 2,6-difluorobenzonitrile with the appropriately substituted amine.

Process for the production of 2,6-diaminobenzonitrile derivatives

The compounds of the formula ##STR1## in which R is hydrogen, halogen, alkyl, alkoxy, hydroxyl, nitro or cyano; and

Antiinflammatory 5H-tetrazolo (5,1-c)(1,4)benzodiazepine derivatives

The compound of formula: ##STR1## where R.sub.1 and R.sub.2 are hydrogen or alkyl;

4,5-Dihydrothiadiazole 1,1-dioxide derivatives

The compounds ##STR1## wherein each X is, independently, --O-- or --NR.sub.5, in which R.sub.5 is hydrogen or alkyl; R is alkyl, R.sub.1 is hydrogen or alkyl, R.sub.2 is hydrogen, hydroxy, amino, alkylamino, dialkylamino or alkanoylamino and when m or n is O, R.sub.2 is hydroxymethyl, aminomethyl, alkylaminomethyl, dialkylaminomethyl or alkanoylaminomethyl; R.sub.3 is hydrogen, --CN, --CONH.sub.2 or --CO.sub.2 M in which M is hydrogen, alkyl or ##STR2## in which p is an integer from 2 to 6 and R.sub.6 and R.sub.7 are, independently, hydrogen or alkyl; R.sub.4 is --NH.sub.2, --NHCOR.sub.8 in which R.sub.8 is alkyl, --NHCOCO.sub.2 Z or --NHCOCH.sub.2 CH.sub.2 CO.sub.2 Z in which Z is hydrogen or alkyl; m and n are 0, 1, 2, 3 or 4 such that when n is from 1 to 4, m is 0 or 1 and when m is from 1 to 4, n is 0 or 1; or pharmaceutically acceptable salts thereof are leucotriene antagonists useful as antiallergy agents.

Leucotriene antagonists

Compounds of the formula ##STR1## wherein A is a moiety of the formula ##STR2## in which R.sub.1 and R.sub.2 may be hydrogen, lower alkyl, lower alkoxy, halogen or thioalkyl; and

Benzo-fused and heterocyclic fused imidazole anti-ulcer agents

N-Protected-tetrazole-5-carboxylic acid derivatives of the formula: ##STR1## in which R is --OM, halo or lower alkoxy wherein M is hydrogen, an alkali metal or an alkaline earth metal; and

N-Benzyl and N-substituted benzyl tetrazole-5-carboxylic acids and the

Anti-secretory, anti-hypertensive agents of the formula are presented: ##STR1## in which R is alkyl of 1 to 6 carbon atoms;

(1H-Imidazol-5-ylmethyl)isothioureas

Variously substituted oxanilic acid esters possessing anti-secretory activity are useful anti-ulcer agents.

Antisecretory oxamic acid esters

Variously substituted oxanilic acid esters possessing anti-secretary activity are useful anti-ulcer agents.

Anti-allergic agents of N-aromatic 1H-(or 2H) tetrazole-5-carboxamide derivation present the following formulae: ##STR1## in which R.sup.1 is --CN or --CONH.sub.2 ;

Process for preparing tetrazole-5-carboxamide derivatives

Tetrazole-5-carboxamide derivatives

Anti-allergic agents of N,N'-arylene-bis-tetrazole-5-carboxamide derivation, pharmaceutically acceptable salts thereof and N-protected intermediates therefor.

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West Chester, PA, United States of America

Dieter H Klaubert