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US 3,974,212 AGranted
[1-Hydroximino-2,2-disubstituted-5-indanyloxy-(or thio)]alkanoic acids
AssigneeMerck & Co., Inc.
InventorsEdward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
Life of this patent
Estimating the term…
Abstract
[1-Hydroximino-2,2-disubstituted-5-indanyloxy-(or thio)]alkanoic acids and their salt, ester, anhydride, amide and 5-tetrazolyl derivatives are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity. The acid products are prepared by treating a 1-oxo-2,2-disubstituted-5-indanyloxy(or thio)alkanoic acids or derivatives thereof with hydroxylamine in the presence of a base.
Claims18
A compound of the formula:
- ##SPC24##
- wherein
- A is oxygen or sulphur;
- R is lower alkyl, cycloalkyl having from 3 to 6 carbon atoms, phenyl, or halo-, hydroxy-, lower alkoxy-, nitro or lower alkyl-substituted phenyl;
- R.sup.1 is lower alkyl, lower alkenyl having from 3 to 5 carbon atoms, lower alkynyl, containing from 3 to 5 carbon atoms, phenyl lower alkyl, phenyl lower alkenyl, hydroxy lower alkyl, lower alkoxy lower alkyl, oxo lower alkyl, hydroxy cycloalkyl having from 4 to 6 carbon atoms and cycloalkyl lower alkyl having 4 to 7 carbon atoms;
- R and R.sup.1 may be joined together with the carbon atom to which they are attached to form a cycloalkyl radical containing from 3 to 7 nuclear carbon atoms, or a hydroxy, or lower alkyl substituted cycloalkyl radical having from 3 to 7 nuclear carbon atoms;
- R.sup.2 is hydrogen, lower alkyl, phenyl, or lower alkyl substituted phenyl;
- R.sup.n is hydrogen, or methyl;
- R.sup.1 and R.sup.2 may be joined together to form a hydrocarbylene ring having up to 5 carbon atoms;
- X.sup.1 is hydrogen, methyl or halo;
- and
- X.sup.2 is methyl or halo;
- or
- X.sup.1 and X.sup.2 may be joined to form a hydrocarbylene chain containing 3 to 4 carbon atoms;
- and
- Y is alkylene or haloalkylene containing from 1 to about 4 carbon atoms, and the non-toxic pharmacologically acceptable salt derivatives thereof.
13 more elements
A compound of the formula:
- ##SPC25##
- wherein
- R.sup.3 is phenyl or halo, hydroxy, lower alkyl or lower alkoxy substituted phenyl, lower alkyl having from 1 to 3 carbon atoms, cycloalkyl containing 5 or 6 carbon atoms, hydroxy cycloalkyl containing 4 to 6 carbon atoms, or phenyl lower alkyl;
- R.sup.4 is lower alkyl having from 1 to 3 carbon atoms;
- R.sup.3 and R.sup.4 may be joined together with the carbon atom to which they are attached to form a cycloalkyl containing 5 to 6 carbon atoms;
- X.sup.3 and X.sup.4 are the same or different radicals selected from methyl or chloro;
- and the non-toxic, pharmacologically acceptable salt, derivatives thereof.
4 more elements
Dependencies are inferred from the claim text.