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US 4,285,947 AGranted
Aldehyde adducts of triamterene
AssigneeINTERx Research Corporation
InventorsTakeru Higuchi, Anand C. Burman
Life of this patent
Estimating the term…
Abstract
The invention provides novel aldehyde adducts of triamterene having improved solubility and bioavailability as compared to triamterene. Pharmaceutical compositions containing the novel adducts and having diuretic activity are also described.
Claims60
An aldehyde adduct of triamterene having the formula:
- ##STR11## wherein R is selected from the group consisting of:
- hydrogen;
- alkyl of 1 to 20 carbon atoms;
- cycloalkyl of 3 to 8 carbon atoms;
- phenyl;
- naphthyl;
- alkenyl of 2 to 20 carbon atoms;
- alkynyl of 2 to 20 carbon atoms;
- cycloalkenyl of 4 to 8 carbon atoms;
- alkanoyl having 1 to 22 carbon atoms;
- alkenoyl having one or two double bonds and having 4 to 22 carbon atoms;
- ##STR12## having a total of 4 to 10 carbon atoms of which 3 to 7 are ring atoms in the cycloalkyl portion and wherein m is zero, one or two and cycloalkyl is unsubstituted or is substituted by 1 or 2 lower alkyl groups;
- phenoxyacetyl;
- 1-naphthalenecarbonyl;
- 2-naphthalenecarbonyl;
- 2-pyridinecarbonyl;
- 3-pyridinecarbonyl;
- 4-pyridinecarbonyl;
- ##STR13## wherein m is zero, one or two and phenyl is unsubstituted or is substituted by 1 to 3 substituents, each of which may be alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halo, trifluoromethyl, dialkylamino having 2 to 8 carbon atoms or alkanoylamino having 1 to 6 carbon atoms;
- substituted phenyl and naphthyl having 1 to 3 substituents, which may be the same or different, each of which is selected from the group consisting of lower alkylthio, lower alkyl, halo, lower alkoxy, nitro, cyano, lower alkanoyl, lower carbalkoxy, di(lower alkyl)amino, lower alkanoyloxy, lower haloalkyl, lower alkylsulfonyl, hydroxy, lower hydroxyalkyl, amino, lower alkanoylamino, lower alkylamino, carboxyl, lower carboxyalkyl, carbamoyl, lower alkylcarbamoyl, di(lower alkyl)carbamoyl, lower alkenyl, lower alkynyl, oxo, and -alkylene-aryl wherein the aryl portion is phenyl or naphthyl and the alkylene portion has up to 6 carbon atoms;
- substituted alkyl, cycloalkyl, alkenyl, alkynyl and cycloalkenyl wherein alkyl, cycloalkyl, alkenyl, alkynyl and cycloalkenyl are as defined above with respect to R, having 1 to 3 substituents, which may be the same or different, each of which is selected from the group consisting of halo, hydroxy, lower alkoxy, carboxy, oxo, lower alkanoyloxy, phenoxy, naphthoxy, and substituted phenoxy and naphthoxy having 1 to 3 substituents, which may be the same or different, each of which is selected from the group of substituents defined above with respect to substituted phenyl and naphthyl;
- saturated and unsaturated heterocyclic groups of 1 to 3 rings, at least one of said rings containing from 1 to 3 of any one or more of the hetero atoms N, S and O, each of said rings being 3- to 8-membered, all ring atoms in each of said rings which are other than N, S and O being carbon, with the proviso that when there are 2 or 3 of said rings, then said rings are fused;
- substituted derivatives of the aforesaid heterocyclic groups having 1 to 3 substituents, which may be the same or different, each of which is selected from the group consisting of lower alkyl, lower haloalkyl, halo, amino, oxo, nitro, hydroxy, lower hydroxyalkyl, carboxyl, lower carboxyalkyl, lower alkanoylamino, lower alkoxy, lower alkanoyl, lower alkanoyloxy, cyano, lower carbalkoxy, lower alkylthio, lower alkylamino, di(lower alkyl)amino, carbamoyl, lower alkylcarbamoyl, di(lower alkyl)carbamoyl, lower alkenyl, lower alkynyl, lower alkylsulfonyl, phenyl, naphthyl, and -alkylene-aryl wherein the aryl portion is phenyl or naphthyl and the alkylene portion has up to 6 carbon atoms;
- and
- a radical of the formula --Alk--Z wherein Alk is an alkylene, alkenylene or alkynylene group having up to 6 carbon atoms and wherein Z is selected from the group consisting of the unsubstituted and substituted cycloalkyl, cycloalkenyl, phenyl, naphthyl, and heterocyclic groups as defined above with respect to R;
- and wherein n is a number from 1 to 3 inclusive, with the proviso that when R is hydrogen, than n can be a number from 1 to 6 inclusive.
23 more elements
Dependencies are inferred from the claim text.