Azaadamantane ester and carbamate derivatives and methods of use thereof

1. A compound of formula (I)

wherein

Y 1 is A, —N(R X )-A, or —C(R Y )═C(R Z )-A; with the proviso that Y 1 is other than unsubstituted benzothien-3-yl or 4-chlorophenyl;

A is an unsubstituted aryl, heteroaryl, unsubstituted arylalkyl, heteroarylalkyl, or heterocyclealkyl, wherein heteroaryl, the heteroaryl moiety of the heteroarylalkyl, and the heterocycle moiety of the heterocyclealkyl, are each independently unsubstituted or substituted; and

R X , R Y , and R Z , at each occurrence, are each independently hydrogen, alkyl, or haloalkyl;

or a pharmaceutically acceptable salt, amide or ester thereof.

2. The compound of claim 1 , wherein Y 1 is A, or a pharmaceutically acceptable salt, amide or ester thereof.

3. The compound of claim 2 , wherein A is aryl or heteroaryl, or a pharmaceutically acceptable salt, amide or ester thereof.

4. The compound of claim 3 , wherein the aryl or heteroaryl is substituted with at least one aryl, heteroaryl or heterocycle, or a pharmaceutically acceptable salt, amide, or ester thereof.

5. The compound of claim 1 , wherein Y 1 is —N(R X )A, or a pharmaceutically acceptable salt, amide, or ester thereof.

6. The compound of claim 5 , wherein A is aryl or heteroaryl, or a pharmaceutically acceptable salt, amide, or ester thereof.

7. The compound according to claim 5 , wherein R X is hydrogen, or a pharmaceutically acceptable salt, amide, or ester thereof.

8. The compound of claim 5 , wherein A is arylalkyl, or a pharmaceutically acceptable salt, amide, or ester thereof.

9. The compound according to claim 1 , selected from the group consisting of

(4s)-(6-chloronicotinoyloxy)-1-azatricyclo[3.3.1.1. 3,7 ]decane;

(4r)-(6-chloronicotinoyloxy)-1-azatricyclo[3.3.1.1. 3,7 ]decane;

(4r)-(6-phenylnicotinoyloxy)-1-azatricyclo[3.3.1.1. 3,7 ]decane;

(4s)-[6-(indol-5-yl)nicotinoyloxy]-1-azatricyclo[3.3.1.1. 3,7 ]decane;

(4r)-[6-(indol-5-yl)nicotinoyloxy]-1-azatricyclo[3.3.1.1. 3,7 ]decane;

(4s)-(5-bromonicotinoyloxy)-1-azatricyclo[3.3.1.1. 3,7 ]decane;

(4r)-(5-bromonicotinoyloxy)-1-azatricyclo[3.3.1.1. 3,7 ]decane;

(4r)-(5-phenylnicotinoyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-[5-(indol-5-yl)nicotinoyloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-[5-(indol-5-yl)nicotinoyloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(furan-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(furan-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(5-bromofuran-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(5-bromofuran-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(4,5-dimethylfuran-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(4,5-dimethylfuran-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(thiophen-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(thiophen-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(thiophen-3-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(thiophen-3-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(5-chlorothiophen-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(5-chlorothiophen-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(5-methylthiophen-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(5-methylthiophen-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(5-bromothiophen-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(5-bromothiophen-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(3-bromothiophen-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(3-bromothiophen-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(5-(2-thienyl)thiophen-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(5-(2-thienyl)thiophen-2-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-1-azatricyclo[3.3.1.1 3,7 ]decan-4-yl 2-(thiophen-2-yl)thiazole-4-carboxylate;

(4r)-1-azatricyclo[3.3.1.1 3,7 ]decan-4-yl 2-(thiophen-2-yl)thiazole-4-carboxylate;

(4s)-(2-naphthoyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(benzothiophen-5-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(benzothiophen-5-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(thieno[2,3-c]pyridine-5-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(thieno[2,3-c]pyridine-5-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(5-bromoindol-3-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(4-bromoindol-3-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(indol-3-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(indol-6-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(benzofuran-5-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(5-methoxy-2-methylbenzofuran-3-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(benzothien-5-ylcarbamoyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(benzothien-5-ylcarbamoyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(4-bromophenylcarbamoyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(4-bromophenylcarbamoyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(2-hydroxyphenylcarbamoyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(benzylcarbamoyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4r)-(benzylcarbamoyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yl 5-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)nicotinate;

(4r)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yl 5-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)nicotinate;

(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yl 2-bromothiazole-4-carboxylate;

(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yl 5-fluoronicotinate;

(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yl 5-(1H-pyrrol-1-yl)nicotinate;

(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yl 3,4′-bipyridine-5-carboxylate;

(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yl 5-(4-chlorophenyl)nicotinate;

(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yl 5-(4-(trifluoromethyl)phenyl)nicotinate;

(4r)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yl 5-(pyridin-2-yl)thiophene-2-carboxylate; and

(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yl nicotinate;

or a pharmaceutically acceptable salt, amide or ester thereof.

10. The compound according to claim 1 , selected from the group consisting of

(4s)-(2-naphthoyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(benzothiophen-5-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(indol-3-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(indol-6-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

(4s)-(benzofuran-5-oyloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;

or pharmaceutically acceptable salts, amides or esters thereof.

11. A pharmaceutical composition comprising a therapeutically effective amount of the compound of claim 1 , or a pharmaceutically acceptable salt, amide or ester thereof, in combination with one or more pharmaceutically acceptable carriers.

12. The pharmaceutical composition of claim 11 , further comprising one or more atypical antipsychotics.