Adamantane analogs

1. A compound having the formula (I):

wherein

X is carbon, —NH(H + Cl − ), alkylene, or alkyleneamino;

R 1 is hydrogen, deuterium, halo, hydroxyl, nitro, guanidinyl, —(R 6 )-guanidine, fonnamidinyl, carbonyl, oxime, amino, aminocarbonyl, aminooxy, aralkoxy, or aralkylaminooxy;

R 2 and R 3 are each independently hydrogen, deuterium, hydroxyl, carbonyl, amino, nitro, alkyl, trifluoromethyl, aryl, aminocarbonyl, or —C(═Y)—Z,

or

R 2 and R 3 taken together along with the atom to which they are both attached form a six-membered carbocyclic ring or a dithanyl ring optionally substituted with up to three substituents independently selected from alkyl, aryl, aralkyl, hydroxyl, nitro, amino, and

carbonyl;

Y is O, S, or NH;

Z is amino, —NH—NH 2 , methyloxy, or methylthio;

R 4 is hydrogen, deuterium, or amino;

R 5 is hydrogen or carbonyl; and,

R 6 is —CH(CH 3 )— or —NH—C(═NH)—;

or a stereoisomer, partial stereoisomer, prodrug, pharmaceutically acceptable salt, hydrate, solvate, acid hydrate, or N-oxide thereof,

with the proviso that if R 1 is amino and X is methylene or ethylene, R 2 , R 3 , R 4 , and R 5 cannot all be hydrogen.

2. The compound according to claim 1 wherein X is carbon, and R 2 , R 3 , R 4 , and R 5 are each hydrogen.

3. The compound according to claim 2 wherein R 1 is guanidinyl, —(R 6 )-guanidine, formamidinyl, carbonyl, oxime, nitro, aminocarbonyl, aminooxy, aralkoxy, or aralkylaminooxy.

4. The compound according to claim 3 wherein R 6 is —CH(CH 3 )— or —NH—C(═NH)—.

5. The compound according to claim 3 wherein R 1 is (5-methyl-3H-imidazol-4-ylmethylene)-amineoxy or hydroxyamino(imino)methyl.

6. The compound according to claim 1 wherein R 1 and R 5 are both hydrogen.

7. The compound according to claim 6 wherein R 2 is hydrogen and R 3 is hydrogen, hydroxyl, carbonyl, amino, nitro, or —C(═Y)—Z.

8. The compound according to claim 7 wherein X is —NH(H + Cl − ) and R 3 is hydrogen, hydroxyl, amino, or —C(═Y)—Z.

9. The compound according to claim 6 wherein R 2 and R 3 taken together along with the atom to which they are both attached form a six-membered carbocyclic ring or a dithanyl ring optionally substituted with up to three substituents independently selected from alkyl, aryl, aralkyl, hydroxyl, nitro, amino, and carbonyl.

10. The compound according to claim 9 wherein R 2 and R 3 taken together form [1,3]Dithian-5-ylamine.

11. The compound according to claim 9 wherein R 2 and R 3 taken together form cyclohexane optionally substituted with up to three substituents independently selected from alkyl, aryl, aralkyl, hydroxyl, nitro, amino, and carbonyl.

12. The compound according to claim 6 wherein R 4 is hydrogen, and R 2 and R 3 are independently selected from hydroxyl, trifluoromethyl, alkyl, amino, nitro, or aryl.

13. The compound according to claim 1 wherein said compound is

N-Adamantan-1-yl-guanidine;

N-(1-Adamantan-1-yl-ethyl)-guanidine;

O-Adamantan-1-yl-hydroxylamine;

5-Methyl-3H-imidazole-4-carbaldehyde O-adamantan-1-yl-oxime;

Adamantane-1-carboxamidine;

Adamantane amidine hydrochloride;

2,2-spiro adamantyl-1,3-dithian-5-aminium chloride;

N-Hydroxy-adamantane-1-carboxamidine;

4-Aza-tricyclo[4.3.1.13,8]undecane;

4-Azonia-tricyclo[4.3.1.13,8]undecane chloride;

Adamantane-1-carbaldehyde;

Adamantan-2-lamine; Adamantane-2,6-dione;

2-Trifluoromethyl-adamantan-2-ol;

2-(4-amino-cyclyhexyl)-adamantane;

1-Nitro-adamantane;

2-Nitro-adamantane;

2-Methyl-adamantan-2-ol;

2-Methyl-adamantan-2-ylamine;

2-Methyl-2-nitro-adamantane;

2-Trifluoromethyl-adamantan-2-ylamine;

2-(1H-Pyrazol-3-yl)-adamantan-2-ol;

2-Aza-tricyclo[3.3.1.13,7]decan-2-ol; Adamantane-1-carboximidic acid methyl ester;

2-Aza-tricyclo[3.3.1.13,7]decane;

2-Aza-tricyclo[3.3.1.13,7]decan-2-ol;

2-Aza-tricyclo[3.3.1.13,7]dec-2-ylamine;

2-Aza-tricyclo[3.3.1.13,7]decane-2-carboxylic acid amide;

2-Aza-tricyclo[3.3.1.13,7]decane-2-carbothioic acid amide;

2-Aza-tricyclo[3.3.1.13,7]decane-2-carboxamidine;

2-Aza-tricyclo[3.3.1.13,7]decane-2-carboximidic acid methyl ester;

2-Aza-tricyclo[3.3.1.13,7]decane-2-carboximidothioic acid methyl ester;

2-Aza-tricyclo[3.3.1.13,7]decan-1-ol;

1-Chloro-2-aza-tricyclo[3.3.1.13,7]decane;

or a stereoisomer, partial stereoisomer, prodrug, pharmaceutically acceptable salt, hydrate, solvate, acid hydrate, and N-oxide thereof.

14. A composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier, diluent, or excipient.