Azaadamantane derivatives and methods of use

Abstract

The invention relates to compounds that are azaadamantane derivatives, particularly ether- or amine-substituted azaadamantane derivatives and salts and prodrugs thereof, compositions comprising such compounds, methods of using such compounds and compositions, processes for preparing such compounds, and intermediates obtained during such processes.

What is claimed is: 
     
         1 . A compound of formula (I) 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof, wherein
 L 1  is —O— or —NR a —; 
 A is —Ar 1 , —Ar 2 -L 2 -Ar 3  or —Ar 4 -L 3 -Ar 5 ; 
 Ar 1  is aryl or heteroaryl; 
 Ar 2  is aryl or monocyclic heteroaryl; 
 Ar 3  is aryl or heteroaryl; 
 Ar 4  is a bicyclic heteroaryl; 
 Ar 3  is aryl or heteroaryl; 
 L 2  is a bond, —O—, —NR a —, —CH 2 —, or —C(O)NR a —; 
 L 3  is a bond, —O—, —NR a — or —CH 2 —; and 
 R a  is hydrogen or alkyl. 
 
     
     
         2 . The compound according to  claim 1 , wherein
 A is Ar 1 .   
     
     
         3 . The compound according to  claim 2 , wherein Ar 1  is selected from 
       
         
           
           
               
               
           
         
         wherein D 1 , E 1 , F 1 , J 1 , K 1 , X 8 , X 9 , X 10 , and X 11  are each independently —CR 1  or N; 
         X 12 , X 13 , X 14 , X 15 , M 1 , and M 2  are each independently —CR 1 , N or C; 
         G 1  is O, —NR 1a , or S; 
         Y 1  is —CR 1  or N; 
         Y 2  is —CR 1  or N; 
         Y 3  is NH, O, or S 
         R 1  is hydrogen, alkyl, alkoxy, alkoxycarbonyl, cyano, halo, nitro, —NR b R c , haloalkyl, or —C(O)NR b R c ; 
         R 1a  is hydrogen or alkyl; 
         R b  and R c  are each independently hydrogen, alkyl, alkoxycarbonyl, or alkylcarbonyl; 
         one of X 12 -X 15  is C; and 
         M 1  or M 2  is C. 
       
     
     
         4 . The compound according to  claim 3 , wherein
 L 1  is —O—.   
     
     
         5 . The compound according to  claim 3 , wherein
 L 1  is —NR a —.   
     
     
         6 . The compound according to  claim 1 , wherein
 A is —Ar 2 -L 2 -Ar 3 .   
     
     
         7 . The compound according to  claim 6 , wherein
 Ar 2  is a group selected from   
       
         
           
           
               
               
           
         
         D 2 , E 2 , F 2 , J 2 , and K 2  are each independently —CT 2  or N; 
         G 2  is O, —NR 2a , or S; 
         in each group of (i), (ii), and (iii), one substituent represented by T 2 , or R 2a  wherein R 2a  is T 2 , is -L 2 -Ar 3  and the other substituents represented by T 2  are hydrogen, alkyl, alkoxy, alkoxycarbonyl, cyano, halo, nitro, or —NR b R c ; 
         R 2a  is hydrogen, alkyl, or T 2 ; and 
         R b  and R c  are each independently hydrogen, alkyl, alkoxycarbonyl or alkylcarbonyl. 
       
     
     
         8 . The compound according to  claim 6 , wherein
 Ar 3  is a group selected from   
       
         
           
           
               
               
           
         
         wherein D 3 , E 3 , F 3 , J 3 , K 3 , X 8 , X 9 , X 10 , and X 11  are each independently —CR 3  or N; 
         X 16 , X 17 , X 18 , X 19 , M 1 , and M 2  are each independently —CR 3 , N, or C; 
         G 3  is O, —NR 3a , or S; 
         Y 1  is —CR 3  or N; 
         Y 2  is —CR 3  or N; 
         Y 3  is NH, O, or S; 
         R 3  is hydrogen, alkyl, alkoxy, alkoxylalkyl, alkoxycarbonyl, alkylcarbonyl, cyano, halo, haloalkoxy, haloalkyl, hydroxy, nitro, R e R f N—, or aryl, wherein aryl is preferably phenyl optionally substituted with halo, alkyl or cyano; 
         R 3a  is hydrogen, alkyl, alkylcarbonyl, tritylaryl, wherein aryl is preferably phenyl; 
         R e  and R f  are each independently hydrogen, alkyl, alkoxycarbonyl, or alkylcarbonyl, or R e  and R f  are each taken together with the nitrogen atom to which they are attached form a heterocyclic ring, wherein the heterocyclic ring is preferably pyrrolidinyl, piperidinyl or piperazinyl; 
         one of X 16 , X 17 , X 18 , and X 19 , is C; and 
         M 1  or M 2  is C; 
       
     
     
         9 . The compound according to  claim 6 , wherein
 L 1  is —NR a —; and   L 2  is a bond.   
     
     
         10 . The compound according to  claim 6 , wherein
 L 1  is —O—; and   L 2  is a bond.   
     
     
         11 . The compound according to  claim 1 , wherein
 A is —Ar 4 -L 3 -Ar 5 .   
     
     
         12 . The compound according to  claim 1 , wherein —Ar 4 -L 3 -Ar 5  is 
       
         
           
           
               
               
           
         
         Y 4  is —NR 4a , O or S; 
         Ys is N, C or —CR 4 ; 
         Y 6  is N, C or —CR 4 ; 
         provided that one of Y 5  and Y 6  is C; 
         R 4  is hydrogen, alkyl, alkoxy, alkoxylalkyl, alkoxycarbonyl, alkylcarbonyl, cyano, halo, haloalkoxy, haloalkyl, hydroxy, nitro, oxo, or R e R f N—; 
         R 4a  is hydrogen or alkyl; 
         R e  and R f  are each independently hydrogen, alkyl, alkoxycarbonyl or alkylcarbonyl, or R e  and R f  are each taken together with the nitrogen atom to which they are attached form a heterocyclic ring, wherein the heterocyclic ring is preferably pyrrolidinyl, piperidinyl or piperazinyl; 
         X 4  is N, C, or —CR X4 ; 
         X 5  is N, C, or —CR X5 ; 
         X 6  is N, C, or —CR X6 ; 
         X 7  is N, C, or —CR X7 ; 
         provided that only one of X 4 , X 5 , X 6 , or X 7  may be N, only one is C, and the remaining must be other than N; and 
         R X4 , R X5 , R X6 , and R X7  are each independently hydrogen or alkyl. 
       
     
     
         13 . A compound of  claim 1 , wherein the compound is
 (4s)-4-(6-chloropyridazin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-(6-chloropyridazin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(6-phenylpyridazin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-(6-phenylpyridazin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[6-(1H-indol-5-yl)pyridazin-3-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-[6-(1H-indol-5-yl)pyridazin-3-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[6-(1-benzothien-5-yl)pyridazin-3-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-[6-(1-benzothien-5-yl)pyridazin-3-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-(5-bromopyridin-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(5-phenylpyridin-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-(5-phenylpyridin-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(1H-indol-5-yl)pyridin-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-[5-(1H-indol-5-yl)pyridin-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-[5-(benzothien-5-yl)pyridin-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(6-chloropyridin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(6-nitropyridin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(6-aminopyridin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-(6-nitropyridin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-(6-aminopyridin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(5-bromothiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(thiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(5-phenylthiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(4-methoxyphenyl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(3-chlorophenyl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(3-chloro-4-methoxyphenyl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(4-fluorophenyl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(3,5-difluorophenyl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(1H-indol-5-yl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(1H-indol-5-yl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane-1-oxide; 5-[2-(1-azatricyclo[3.3.1.1 3,7 ]decan-(4s)-yloxy)thiazol-5-yl]-indolin-2-one;   5-[2-(1-azatricyclo[3.3.1.1 3,7 ]decan-1-oxide-(4s)-yloxy)thiazol-5-yl]-indolin-2-one;   (4s)-4-[5-(2-trifluoromethyl-1H-indol-5-yl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(1H-indol-4-yl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(1H-indol-6-yl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(1H-indol-3-yl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(pyridin-4-yl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(furan-2-yl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(furan-3-yl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(thien-3-yl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(pyrazol-4-yl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(5-bromo-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(5-phenyl-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(5-phenyl-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane-1-oxide;   (4r)-4-(5-phenyl-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(3-fluorophenyl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-[5-(3-fluorophenyl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(1H-indol-5-yl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(1H-indol-6-yl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(1H-indol-4-yl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(benzothien-5-yl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(pyrazol-4-yl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(5-phenoxy-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(5-tert-butyl-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-(5-tert-butyl-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(5-phenyl-1,3,4-oxadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-(5-phenyl-1,3,4-oxadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(benzothiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-(benzothiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(6-chlorobenzothiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-(6-chlorobenzothiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(benzoxazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-N-(6-chloropyridin-3-yl)-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4r)-N-(6-chloropyridin-3-yl)-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-N-(6-phenylpyridin-3-yl)-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-N-[6-(indol-5-yl)-pyridin-3-yl]-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-N-(5-bromopyridin-3-yl)-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-N-[5-(indol-5-yl)-pyridin-3-yl]-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-N-[5-(indol-6-yl)-pyridin-3-yl]-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-N-[5-(indol-4-yl)-pyridin-3-yl]-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-N-[5-(3-methylphenyl)-pyridin-3-yl]-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-N-[5-(3-chlorophenyl)-pyridin-3-yl]-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-4N-[5-(3-chlorophenylphen-3-yl)-pyridin-3-yl]-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-4-(pyridin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(1-oxidopyridin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-(pyridin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(2-chloropyridin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(2-bromopyridin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(4-chloropyridin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(4-methylpyridin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[4-(trifluoromethyl)pyridin-3-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(5-fluoropyridin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(5-chloropyridin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(5-bromopyridin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(5-iodopyridin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   5-[(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yloxy]nicotinamide;   (4s)-4-{[5-(1H-pyrazol-4-yl)pyridin-3-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(1H-pyrazol-1-yl)pyridin-3-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(4-chlorophenyl)pyridin-3-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(3,4′-bipyridin-5-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(5-pyrimidin-5-ylpyridin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-[(6-chloropyridin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(6-bromopyridin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   5-[(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yloxy]pyridine-2-carbonitrile;   (4s)-4-[(5-thien-2-ylpyridin-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[6-(1H-indol-5-yl)pyridin-3-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-{[6-(1H-indol-5-yl)pyridin-3-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[6-(1H-indol-6-yl)pyridin-3-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-{[6-(1H-indol-6-yl)pyridin-3-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   5-{5-[(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yloxy]pyridin-2-yl}-1,3-dihydro-2H-indol-2-one;   (4r)-4-{[6-(1-benzofuran-5-yl)pyridin-3-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(5,6-dibromopyridin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(pyridin-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(5-fluoropyridin-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(5-bromopyridin-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(4-bromopyridin-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(3,3′-bipyridin-6-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(3,4′-bipyridin-6-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-(3,4′-bipyridin-6-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(5-pyrimidin-5-ylpyridin-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(1H-pyrazol-4-yl)pyridin-2-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   6-[(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yloxy]-N-pyridin-4-ylpyridin-2-carboxamide;   (4s)-4-[(2-chloropyridin-4-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(6-methylpyridazin-3-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(pyrimidin-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(5-bromopyrimidin-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(pyrimidin-5-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(pyrimidin-4-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(6-chloropyrimidin-4-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[6-(1-trityl-1H-pyrazol-4-yl)pyrimidin-4-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[6-(1H-pyrazol-4-yl)pyrimidin-4-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(6-pyridin-4-ylpyrimidin-4-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-(pyrazin-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   4-[(6-methylpyrazin-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-[(6-phenylpyrazin-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-(1,3-thiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-[(5-bromo-1,3-thiazol-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-({5-[4-(trifluoromethoxy)phenyl]-1,3-thiazol-2-yl}oxy)-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(4-chlorophenyl)-1,3-thiazol-2-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   4-{2-[(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yloxy]-1,3-thiazol-5-yl}aniline;   (4s)-4-[(5-pyridin-3-yl-1,3-thiazol-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-[(5-pyridin-3-yl-1,3-thiazol-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(5-pyrimidin-5-yl-1,3-thiazol-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(2-methoxypyrimidin-5-yl)-1,3-thiazol-2-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(2-pyrrolidin-1-ylpyrimidin-5-yl)-1,3-thiazol-2-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(6-piperazin-1-ylpyridin-3-yl)-1,3-thiazol-2-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(1H-pyrazol-1-yl)-1,3-thiazol-2-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(1-trityl-1H-pyrazol-4-yl)-1,3-thiazol-2-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(1-propyl-1H-pyrazol-4-yl)-1,3-thiazol-2-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(1-isobutyl-1H-pyrazol-4-yl)-1,3-thiazol-2-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(1-acetyl-1H-pyrazol-4-yl)-1,3-thiazol-2-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-1,3-thiazol-2-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(5-isoxazol-4-yl-1,3-thiazol-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(4-bromo-1,3-thiazol-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-[(4-bromo-1,3-thiazol-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(4-chloro-1,3-thiazol-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{[4-(1H-pyrazol-4-yl)-1,3-thiazol-2-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(4-phenyl-1,3-thiazol-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(4-pyridin-4-yl-1,3-thiazol-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[(4-pyridin-3-yl-1,3-thiazol-2-yl)oxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   2-[(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yloxy]-N-pyridin-4-yl-1,3-thiazole-4-carboxamide;   2-[(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yloxy]-N-(4-chlorophenyl)-1,3-oxazole-4-carboxamide;   2-[(4s)-1-azatricyclo[3.3.1.1 3,7 ]dec-4-yloxy]-N-phenyl-1,3-oxazole-4-carboxamide;   (4s)-4-{[5-(3-bromophenyl)-1,3,4-thiadiazol-2-yl]oxy}-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-{5-[1-azatricyclo[3.3.1.1 3,7 ]dec-4-yloxy]-1,3,4-thiadiazol-2-yl}phenol;   (4s)-N-pyridin-3-yl-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-N-(5-bromo-6-chloropyridin-3-yl)-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-N-[6-(1H-indol-6-yl)pyridin-3-yl]-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-N-[6-(1H-indol-3-yl)pyridin-3-yl]-1-azatricyclo[3.3.1.1 3,7 ]decan-4-amine;   (4s)-4-[5-(1H-indol-5-yl)pyridin-3-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4s)-4-[5-(1H-indol-6-yl)pyridin-3-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-[5-(1H-indol-5-yl)pyridin-3-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane;   (4r)-4-[5-(1H-indol-6-yl)pyridin-3-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane; or   (4r)-4-[5-(1-benzofuran-5-yl)pyridin-3-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane.   
     
     
         14 . A method for treating or preventing conditions, disorders, or deficits modulated by α7 nicotinic acetylcholine receptors, α4β2 nicotinic acetylcholine receptors, or both α7 and α4β2 nicotinic acetylcholine receptors wherein the condition, disorder, or deficit is selected from the group consisting of a memory disorder, cognitive disorder, neurodegeneration, and neurodevelopmental disorder comprising administration of a therapeutically suitable amount of a compound of formula (I). 
     
     
         15 . The method according to  claim 14 , wherein the condition or disorder is selected from the group consisting of attention deficit disorder, attention deficit hyperactivity disorder (ADHD), Alzheimer's disease (AD), mild cognitive impairment, schizophrenia, age-associated memory impairment (AAMI), senile dementia, AIDS dementia, Pick's disease, dementia associated with Lewy bodies, dementia associated with Down's syndrome, amyotrophic lateral sclerosis, Huntington's disease, smoking cessation, nicotinic withdrawal syndrome, schizoaffective disorder, bipolar and manic disorders, diminished CNS function associated with traumatic brain injury, acute pain, post-surgical pain, chronic pain, inflammatory pain, and neuropathic pain. 
     
     
         16 . The method according to  claim 14 , wherein the condition or disorder is cognitive deficits associated with attention deficit hyperactivity disorder, schizophrenia, Alzheimer's disease, mild cognitive impairment, age-associated memory impairment, and cognitive deficits of schizophrenia. 
     
     
         17 . The method according to  claim 14 , further comprising administering a compound of formula (I) in combination with an atypical antipsychotic. 
     
     
         18 . The method according to  claim 14 , wherein the condition or disorder is selected from the group consisting of infertility, lack of circulation, need for new blood vessel growth associated with wound healing, need for new blood vessel growth associated with vascularization of skin grafts, ischemia, inflammation, arthritis and related disorders, wound healing, and complications associated with diabetes. 
     
     
         19 . A method of using the compound of formula (V) 
       
         
           
           
               
               
           
         
         to prepare compounds of formula (I) of  claim 1 . 
       
     
     
         20 . A compound of formula (VI) 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof, wherein
 L 1  is —O— or —NR a —; 
 A is —Ar 1 , —Ar 2 -L 2 -Ar 3  or —Ar 4 -L 3 -Ar 5 ; 
 Ar 1  is aryl or heteroaryl; 
 Ar 2  is aryl or monocyclic heteroaryl; 
 Ar 3  is aryl or heteroaryl; 
 Ar 4  is bicyclic heteroaryl; 
 Ar 5  is aryl or heteroaryl; 
 L 2  is a bond, —O—, —NR a —, —CH 2 —, or —C(O)NR a —; 
 L 3  is a bond, —O—, —NR a — or —CH 2 —; and 
 R a  is hydrogen or alkyl. 
 
     
     
         21 . The compound of  claim 20 , wherein the compound is a prodrug of a compound of formula (I) of  claim 1 . 
     
     
         22 . The compound of  claim 20 , wherein the compound is
 (4r)-4-(5-bromopyridin-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4s)-4-(6-chloropyridin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4s)-4-(6-nitropyridin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4r)-4-(6-nitropyridin-3-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4s)-4-(5-bromothiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4s)-4-(5-phenyl-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4r)-4-(5-phenyl-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4s)-4-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4r)-4-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4s)-4-[5-(3-fluorophenyl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4r)-4-[5-(3-fluorophenyl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4s)-4-[5-(1H-indol-5-yl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4s)-4-(5-tert-butyl-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4r)-4-(5-tert-butyl-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4s)-4-(benzothiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4r)-4-(benzothiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4s)-4-(6-chlorobenzothiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex;   (4r)-4-(6-chlorobenzothiazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex; or   (4s)-4-(benzoxazol-2-yloxy)-1-azatricyclo[3.3.1.1 3,7 ]decane N-borane complex.