Anti-diarrheal oxadiazoles

Details Anti-diarrheal oxadiazoles Anti-diarrheal oxadiazoles

1975-04-16

1977-01-18

Jiles, Henry R.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602475R, 26029367, 260296R, 260296B, 260307G, 260308D, 4242484, 424263, 424267, 424269, 42424857, C07D 8554

Patent

active

040039048

ABSTRACT:
The present invention encompasses a compound of the formula ##STR1## and the pharmaceutically acceptable acid addition salts thereof wherein Y is alkylene having 1-4 carbon atoms; R.sub.1 and R.sub. 2 together with N is a heterocyclic ring system consisting of an azamonocyclic ring of the formula ##STR2## wherein Z is oxygen, methylene, phenylhydroxymethylene, phenylcarboxymethylene or, phenylloweralkoxymethylene, or an azabicycloalkane structure having 6-9 carbon atoms and having at least 5 atoms in each ring of the azabicycloalkane structure; X is hydrogen, halogen, loweralkyl having 1-7 carbon atoms, or loweralkoxy having 1-7 carbon atoms; and Ar is phenyl, pyridyl, or monosubstituted phenyl wherein the substituent is halogen, loweralkyl having 1-7 carbon atoms, or loweralkoxy having 1-7 carbon atoms when R.sub.3 is hydrogen or Ar is 3 or 4 pyridyl when R.sub.3 is lower alkyl having 1-7 carbon atoms.
The compounds of the present invention are prepared by converting the corresponding nitriles to 1H-tetrazoles and in turn reacting the 1H-tetrazole with ethyl chloroglyoxylate, hydrolyzing the resulting ester to the acid and decarboxylation to provide compounds wherein R.sub.3 is hydrogen. Compounds of the present invention are anti diarrheal agents.

REFERENCES:
patent: 3141019 (1964-07-01), Palazzo et al.
patent: 3299044 (1967-01-01), Cusic et al.
patent: 3502668 (1970-03-01), Palazzo et al.
patent: 3585209 (1971-06-01), Derappe
patent: 3655684 (1972-04-01), Osbond et al.
patent: 3720685 (1973-03-01), Breuer et al.
patent: 3917615 (1975-11-01), Adelstein

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