Lipophilic polyamine esters for the site specific delivery of nitric oxide in pharmaceutical use
AssigneeThe University of Akron
InventorsDaniel J. Smith, Dominick Roselle
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Abstract
A pharmaceutical composition of matter for delivering nitric oxide. The composition is an amine that was reacted with nitric oxide. The composition of matter is lipophilic and insoluble and therefore delivers nitric oxide to the specific area of the body where it is introduced. Also, a method of synthesizing an amine and reacting it with nitric oxide to form the pharmaceutical composition of matter. Finally, a method of using the pharmaceutical composition of matter to deliver nitric oxide to the body.
Claims28
A NONOate compound that releases nitric oxide when introduced to physiological mediums, where said NONOate is defined by the formula (II) ##STR18## wherein R.sub.2 is selected from the group consisting of hydrogen, organic radicals having between 2 and 20 carbon atoms, and steroid radicals, R.sub.3 can be selected from the group consisting of organic radicals having between 2 and 20 carbon atoms and steroid radicals, and R.sub.4 is selected from the group consisting of organic radicals having between 2 and 3 carbon atoms, wherein said NONOate is insoluble in physiological mediums, and wherein said NONOate defined by formula (II) is electronically balanced with a pharmaceutically acceptable cation.
A NONOate compound that releases nitric oxide when introduced to physiological mediums, where said NONOate is defined by the formula (III) ##STR19## wherein R.sub.5 is selected from the group consisting of organic radicals having between 1 and 20 carbon atoms, and steroid radicals, R.sub.6 is selected from the group consisting of organic radicals having between 2 and 6 carbon atoms, and R.sub.7 is selected from the group consisting of hydrogen, an organic radical having between 1 and 20 carbon atoms, and steroid radicals, wherein said NONOate is insoluble in physiological mediums.
A method of synthesizing a NONOate comprising the steps of:
- reacting an acyl chloride with an alcohol to form an acrylate;
- reacting the acrylate with an amine having at least one terminal amine group to form an amine ester derivative;
- and
- reacting the amine ester derivative with nitric oxide to form a NONOate.
A method of providing nitric oxide to a specific area of the body comprising the step of delivering a composition of matter to a specific area of the body, the composition of matter comprising a NONOate, wherein the NONOate is insoluble in physiological mediums.
Dependencies are inferred from the claim text.