Nitric oxide-releasing amidine- and enamine-derived diazeniumdiolates, compositions and uses thereof and method of making same

A compound selected from the group consisting of:

• wherein
• R1-R3 are independently hydrogen, an unsubstituted or substituted C1-12 straight chain alkyl, an unsubstituted or substituted C3-12 branched chain alkyl, an unsubstituted or substituted C3-12 straight chain olefinic, an unsubstituted or substituted C3-12 branched chain olefinic, a substituted or unsubstituted C3-8 cycloalkyl, a C3-8 heterocyclic ring bound through a carbon atom and in which the heteroatom is oxygen or nitrogen, a substituted or unsubstituted naphthyl, a substituted or unsubstituted tetrahydronaphthyl, a substituted or unsubstituted octahydronaphthyl, benzyl or substituted benzyl, substituted with up to three substituents, or phenyl or substituted phenyl, substituted with up to three substituents;
• R4 and R5 are independently chosen from hydrogen, an unsubstituted or substituted C1-12 straight chain alkyl, an unsubstituted or substituted C3-12 branched chain alkyl, an unsubstituted or substituted C3-12 straight chain olefinic, an unsubstituted or substituted C3-12 branched chain olefinic, a substituted or unsubstituted benzyl, an unsubstituted or substituted phenyl, a substituted or unsubstituted piperazino, a substituted or unsubstituted morpholino, amino, an unsubstituted or substituted alkylamino, an unsubstituted or substituted arylamino, an unsubstituted or substituted dialkylamino, an unsubstituted or substituted diarylamino, carboxyalkylamino, carboxydialkylamino, unsubstituted or substituted tolyl, xylyl, anisyl, mesityl, an unsubstituted or substituted acetyl, an unsubstituted or substituted acetoxy, carboxy, an unsubstituted or substituted carboxymethyl, an unsubstituted or substituted carboxyethyl, an unsubstituted or substituted alkylcarbonyl, thiol, an unsubstituted or substituted alkylthio, an unsubstituted or substituted alkoxy, carboxamido, an unsubstituted or substituted alkylcarboxamido, or an unsubstituted or substituted dialkylcarboxamido, an unsubstituted or substituted phenoxy, an unsubstituted or substituted benzyloxy, phenylcarbonyl, benzylcarbonyl, an unsubstituted or substituted nitrophenyl, trialkylsilyl or nitro;
• and
• R1 and R2 together with the nitrogen atoms to which they are bonded and with the intervening carbon atom form a substituted or unsubstituted five-membered heterocyclic ring comprising, in addition to the nitrogen atoms to which R1 and R2 are bonded, 0 to 1 heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur, or
• R2 and R3 together with the nitrogen atom to which they are bonded form a substituted or unsubstituted five-membered heterocyclic ring comprising, in addition to the nitrogen atom to which R2 and R3 are bonded, 0 to 1 heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur, or
• R1 and R4 together with the nitrogen atom to which R1 is bonded and with the carbon atom to which R4 is bonded and with the intervening carbon atom form a substituted or unsubstituted five-membered heterocyclic ring comprising, in addition to the nitrogen atom to which R1 is bonded, 0 to 2 heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur, or
• R4 and R5 together with the carbon atom to which they are bonded form a five-membered heterocyclic ring in which the heteroatom is nitrogen.