Diazeniumdiolate cyclohexyl derivatives

1. A compound of the formula I:

or a pharmaceutically acceptable salt thereof, wherein

R 3 is hydrogen, deuterium, —OH, —OC 1-6 alkyl, or halogen;

R 8 is hydrogen, deuterium, or —C 1-6 alkyl;

R 11 and R 12 are independently hydrogen, —C 1-6 alkyl, —OH, —OC 1-6 alkyl, or halogen;

R 13 and R 14 are independently —C 1-6 alkyl, —(CH 2 ) 1-2 OH, or —OC 1-6 alkyl, or, together with the nitrogen atom to which they are attached, form a 4- to 7-membered heterocyclic ring containing one nitrogen atom and 0 or 1 oxygen atoms, wherein said ring is unsubstituted or mono-, di- or tri-substituted with halogen or —C 1-6 alkyl;

—C(O)OCH 2 CH 2 N + (CH 3 ) 3 ,

—C(O)NHCH(R 17 )OR 16 , or

—C(O)NHCH(R 17 )C(O)NHCH(R 18 )C(O)OR 16 ;

R 16 is hydrogen, —C 1-6 alkyl, or —(CH 2 ) 1-2 N + R 19 R 20 R 21 ; and

R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 9 , R 10 , R 17 , R 18 , R 19 , R 20 , and R 21 are independently hydrogen or —C 1-6 alkyl.

2. A compound of claim 1 , wherein R 1 and R 2 are hydrogen, or a pharmaceutically acceptable salt thereof.

3. A compound of claim 1 , wherein R 3 is hydrogen or deuterium, or a pharmaceutically acceptable salt thereof.

4. A compound of claim 1 , wherein R 5 is hydrogen or methyl, or a pharmaceutically acceptable salt thereof.

5. A compound of claim 1 , wherein R 4 , R 6 , R 7 , R 8 , R 9 , and R 10 , are hydrogen, or a pharmaceutically acceptable salt thereof.

6. A compound of claim 1 , wherein R 13 is —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 2 CH 3 , or —CH 2 CH 2 OH, or a pharmaceutically acceptable salt thereof.

7. A compound of claim 1 , wherein R 14 is —CH(CH 3 ) 2 , —CH 2 CH 3 , or —C(CH 3 ) 3 , or a pharmaceutically acceptable salt thereof.

8. A compound of claim 1 , wherein R 15 is —C(O)OH, or a pharmaceutically acceptable salt thereof.

9. A compound of claim 1 , wherein R 15 is —C(O)OCH 2 CH 2 N + (CH 3 ) 3 , or a pharmaceutically acceptable salt thereof.

10. A compound of claim 1 , wherein R 15 is —C(O)NHCH(CH(CH 3 ) 2 )OR 16 , or —C(O)NHCH(CH(CH 3 ) 2 )C(O)NHCH(CH(CH 3 ) 2 )C(O)OR 16 , and wherein R 16 is hydrogen or —CH 3 , or a pharmaceutically acceptable salt thereof.

11. A compound of claim 1 , which is

Cis-4-({[(1Z)-2-tert-butyl-2-ethyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)-cyclohexanecarboxylic acid,

Trans-4-({[(1Z)-2-tert-butyl-2-ethyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)-cyclohexanecarboxylic acid,

Cis-4-({[(1Z)-2-tert-butyl-2-methyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)-cyclohexanecarboxylic acid,

Cis-4-({[(1Z)-2-butyl-2-tert-butyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)-cyclohexanecarboxylic acid,

Cis-4-({[(1Z)-2-methyl-1-oxido-(2-propan-2-yl)-1λ 5 -diazan-1-ylidene]amino}oxy)-cyclohexanecarboxylic acid,

Trans-4-({[(1Z)-2-tert-butyl-2-methyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)-cyclohexanecarboxylic acid,

Trans-4-({[(1Z)-2-tert-butyl-2-(2-hydroxyethyl)-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)-cyclohexanecarboxylic acid,

Trans-4-({[(1Z)-2-butyl-2-tert-butyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)-cyclohexanecarboxylic acid,

Trans-4-({[(1Z)-2-methyl-1-oxido-(2-propan-2-yl)-1λ 5 -diazan-1-ylidene]amino}oxy)-cyclohexanecarboxylic acid,

Trans-4-({[(1Z)-2,2-diethyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)-cyclohexanecarboxylic acid,

Cis-4-({[(1Z)-2-tert-butyl-2-methyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)(1- 2 H)cyclohexanecarboxylic acid,

Trans-4-({[(1Z)-2-tert-butyl-2-methyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)(1- 2 H)cyclohexanecarboxylic acid,

(1RS,2SR,4RS)-4-({[(1Z)-2-tert-butyl-2-methyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)-2-methylcyclohexanecarboxylic acid,

(1RS,2SR,4RS)-4-({[(1Z)-2-tert-butyl-2-methyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)-2-methylcyclohexanecarboxylic acid,

(1RS,2RS,4RS)-4-({[(1Z)-2-tert-butyl-2-methyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)-2-methylcyclohexanecarboxylic acid,

(1RS,2RS,4RS)-4-({[(1Z)-2-tert-butyl-2-methyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)-2-methylcyclohexanecarboxylic acid,

(1RS,3SR)-3-({[(1Z)-2-tert-butyl-2-methyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)cyclohexanecarboxylic acid,

[4-{([(1Z)-2-tert-butyl-2-methyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)cyclohexyl]acetic acid,

3-[4-({[(1Z)-2-tert-butyl-2-methyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)cyclohexyl]propanoic acid,

2-({[cis-4-({[(1Z)-2-tert-butyl-2-methyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)cyclohexyl]carbonyl}oxy)-N,N,N-trimethylethanaminium trifluoroacetate,

2-({[cis-4-({[(1Z)-2-tert-butyl-2-ethyl-1-oxido-1λ 5 -diazan-1-ylidene]amino}oxy)cyclohexyl]carbonyl}oxy)-N,N,N-trimethylethanaminium trifluoroacetate,

or a pharmaceutically acceptable salt thereof.

12. A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier.

13. A pharmaceutical composition comprising a compound of claim 11 and a pharmaceutically acceptable carrier.

14. A pharmaceutical composition comprising a compound of claim 11 , a diuretic, and a pharmaceutically acceptable carrier.

15. A method for treating hypertension in a patient which comprises administering to the patient a therapeutically effective amount of the composition of claim 13 .