Novel 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:

• 20
• 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 form a substituted or unsubstituted C2-8 heterocyclic ring, or
• R2 and R3 together with the nitrogen atom to which they are bonded form a substituted or unsubstituted C3-8 heterocyclic ring, 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 C2-6 heterocyclic ring, or
• R4 and R5 together with the carbon atom to which they are bonded form an unsubstituted or substituted C3-8 cycloalkyl, or a C4-8 heterocyclic ring in which the heteroatom is 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 an unsubstituted or substituted 1,4-benzodioxane, 1,3-benzodioxole, tetrahydronaphthlene, octahydronaphthalene, piperazine, morpholine, tetrahydroquinoline, tetrahydroquinoxaline, tetrahydroisoquinoline;
• with the proviso that the heterocyclic ring formed by R1 and R2, R2 and R3, R1 and R4, or R4 and R5 is not a five-membered heterocyclic ring in which the heteroatom is oxygen, nitrogen, or sulfur, or six-membered heterocyclic ring in which the heteroatom is nitrogen.

A compound selected from the group consisting of

• 24
• wherein R1, R2, R5 and R6 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 benzyl, a substituted or unsubstituted 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, cyano, a substituted or unsubstituted 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, anunsubstituted or substituted alkylcarboxamido, or an unsubstituted or substituted dialkylcarboxamido, a substituted or unsubstituted phenoxy, a substituted or unsubstituted benzyloxy, phenylcarbonyl, benzylcarbonyl, a substituted or unsubstituted nitrophenyl, trialkylsilyl or nitro,
• R1 and R2 together with the carbon to which they are bonded can form a substituted or unsubstituted C4-C8 cycloalkyl,
• R2 and R3 together with the nitrogen atom to which they are bonded form a substituted or unsubstituted C3-8 cycloalkyl,
• R3 and R4 are 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 substituted or unsubstituted 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, or
• R3 and R4 together with the nitrogen atom to which they are bonded can form a C3-8 heterocyclic ring or a C3-8 substituted heterocyclic ring or a C3-8 unsubstituted or substituted heterocyclic ring containing up to two additional heteroatoms selected from the group O, S, N, or
• R1 and R6 together with the C═C—C through which they are bonded form an unsubstituted or substituted cycloalkyl, or
• R5 and R6 together with the carbon to which they are bonded can form a substituted or unsubstituted C4-8 cycloalkyl.

A compound of

• 25
• wherein R1 and R2 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 benzyl, a substituted or unsubstituted 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, cyano, a substituted or unsubstituted 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, a substituted or unsubstituted phenoxy, a substituted or unsubstituted benzyloxy, phenylcarbonyl, benzylcarbonyl, a substituted or unsubstituted nitrophenyl, trialkylsilyl or nitro,
• R3 and R4 are 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 substituted or unsubstituted 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.

A compound of

• 26
• wherein R5 and R6 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 benzyl, a substituted or unsubstituted 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, cyano, a substituted or unsubstituted 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, a substituted or unsubstituted phenoxy, a substituted or unsubstituted benzyloxy, phenylcarbonyl, benzylcarbonyl, a substituted or unsubstituted nitrophenyl, trialkylsilyl or nitro,
• R3 and R4 are 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 substituted or unsubstituted 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.