Positive allosteric modulators of the muscarinic acetylcholine receptor m1

Abstract

Described are positive allosteric modulators of muscarinic acetylcholine receptor M1 (mAChR M1), pharmaceutical compositions including the compounds, and methods of using the compounds and compositions for treating neurological disorders, psychiatric disorders, or a combination thereof.

What is claimed is: 
     
         1 . A compound of formula (I), 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, wherein 
         X is CR 3a  or N; 
         Y is CR 3b  or N; 
         Z is S, O, or NR 4 ; 
         L is —[C(R a R b )] p —, C 2 -C 6 -alkenylenyl, C(O), O, or S; 
         A 1  is Cyc 1  or Cyc 2 -Q-Cyc 3 ; 
         R 1  is hydrogen, alkyl, alkoxy, alkoxyalkyl, halogen, cyano, or haloalkyl; 
         R 2  is hydrogen, alkyl or haloalkyl; 
         M is a bond, C 2 -C 6 -alkenylenyl, or —[C(R c R d )] t —[C(R e R f )] k —; 
         A 2  is alkyl, alkoxy, hydroxyalkyl, alkoxyalkyl, haloalkyl, cyanoalkyl, cycloalkyl, heterocycle, heteroaryl, or aryl, each of which is independently substituted or unsubstituted; or A 2  and R 2 , together with the atoms to which they are attached, form a heterocycle; 
         R 3a  and R 3b  are each independently selected from hydrogen, alkyl, cyano, alkoxy, alkoxyalkyl, haloalkyl, and halogen; 
         R 4  is hydrogen, or alkyl; 
         R 5  is independently, at each occurrence, hydrogen, alkyl, or —C(O)R g ; 
         Cyc 1  is aryl, heteroaryl, heterocycle or cycloalkyl; 
         Cyc 2  is aryl, heteroaryl, heterocycle or cycloalkyl; 
         Q is a bond, C 1 -C 6 -alkylenyl, C 2 -C 6 -alkenylenyl, C(O)NH, O, S, or NR 5 ; 
         Cyc 3  is aryl, heteroaryl, heterocycle or cycloalkyl, each of which is independently substituted or unsubstituted; 
         R a , R b , R c , R d , R e , and R f  are each independently hydrogen, alkyl, hydroxyalkyl, haloalkyl, hydroxy, cyano, alkoxy, alkoxyalkyl, or halogen; 
         p is 1, 2, 3, 4, 5, or 6; 
         t is 0, 1, 2, or 3; 
         k is 0, 1, 2, or 3; and 
         R g  is independently, at each occurrence, alkyl, aryl, heteroaryl, cycloalkyl or alkoxy; wherein said aryl, heteroaryl, cycloalkyl, and heterocycle, at each occurrence, are independently substituted or unsubstituted. 
       
     
     
         2 . The compound of  claim 1 , wherein
 X is CR 3a ;   Y is CR 3b ; and   Z is S or O.   
     
     
         3 . The compound of  claim 2 , wherein
 R 3a  is hydrogen;   R 3b  is hydrogen; and   Z is S.   
     
     
         4 . The compound of  claim 1 , wherein
 X is CR 3a ;   Y is CR 3b ; and   Z is NR 4 .   
     
     
         5 . The compound of  claim 4 , wherein
 R 3a  is hydrogen;   R 3b  is hydrogen; and   R 4  is alkyl.   
     
     
         6 . The compound of  claim 1 , wherein
 X is CR 3a ;   Y is N; and   Z is NR 4 .   
     
     
         7 . The compound of  claim 6 , wherein
 R 3  is hydrogen; and   R 4  is alkyl.   
     
     
         8 . The compound of any one of  claims 1 - 7 , wherein
 R 1  is hydrogen; and   R 2  is hydrogen.   
     
     
         9 . The compound of  claim 1 , wherein the compound is a compound of formula (I-a): 
       
         
           
           
               
               
           
         
       
     
     
         10 . The compound of  claim 1 , wherein the compound is a compound of formula (I-b): 
       
         
           
           
               
               
           
         
       
     
     
         11 . The compound of  claim 1 , wherein the compound is a compound of formula (I-c): 
       
         
           
           
               
               
           
         
       
     
     
         12 . The compound of  claim 10  or  claim 11 , wherein R 4  is methyl or ethyl. 
     
     
         13 . The compound of any one of  claims 1 - 12 , wherein
 L is —[C(R a R b )] p —;
 R a  and R b  are each independently hydrogen or alkyl; 
 p is 1; 
   A 1  is Cyc 2 -Q-Cyc 3 ;
 Cyc 2  is aryl or heteroaryl; 
 Q is a bond; and 
 Cyc 3  is heteroaryl. 
   
     
     
         14 . The compound of  claim 13 , wherein
 R a  and R b  are each hydrogen.   
     
     
         15 . The compound of  claim 14 , wherein
 Cyc 2  is selected from phenyl and a six-membered heteroaryl ring having 1 or 2 nitrogen atoms.   
     
     
         16 . The compound of  claim 15 , wherein the six-membered heteroaryl ring is pyridyl. 
     
     
         17 . The compound of any of  claims 13 - 16 , wherein
 Cyc 3  is a five-membered heteroaryl ring having 1 or 2 heteroatoms selected from nitrogen, oxygen and sulfur.   
     
     
         18 . The compound of  claim 17 , wherein
 Cyc 3  is selected from pyrazolyl, oxazolyl and thiazolyl, each of which may be unsubstituted or substituted with 1 or 2 substituents independently selected from the group consisting of alkyl, halogen, and haloalkyl.   
     
     
         19 . The compound of any one of  claims 1 - 18 , wherein
 M is a bond or —[C(R c R d )] t —[C(R e R f )] k —;
 R c , R d , R e , and R f  are each independently hydrogen, alkyl, hydroxyalkyl, or hydroxy; 
 t is 0 or 1; 
 k is 0 or 1; and 
   A 2  is selected from cycloalkyl, heterocycle, and alkoxyalkyl, each of which may be unsubstituted or substituted with 1 or 2 substituents selected from halo, alkyl, haloalkyl and hydroxy.   
     
     
         20 . The compound of  claim 19 , wherein
 t is 1;   k is 0; and   R c  and R d  are each independently hydrogen.   
     
     
         21 . The compound of any one of  claims 1 - 20 , wherein
 A 2  is selected from cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and 2-oxaspiro[3.3]heptan-6-yl, each of which is independently unsubstituted or substituted with 1 or 2 substituents selected from alkyl, hydroxy, halo and haloalkyl.   
     
     
         22 . The compound of any one of  claims 1 - 20 , wherein
 A 2  is a 4-, 5- or 6-membered heterocyclic ring having one or two heteroatoms independently selected from oxygen, nitrogen and sulfur.   
     
     
         23 . The compound of  claim 22 , wherein
 A 2  is selected from azetidinyl, oxetanyl, tetrahydrofuranyl, and tetrahydropyranyl, each of which is independently unsubstituted or substituted with 1 or 2 substituents selected from alkyl, hydroxy, halo, haloalkyl, and heterocyclyl.   
     
     
         24 . The compound of  claim 1 , wherein the compound is selected from:
 1-methyl-N-tetrahydropyran-4-yl-4-[(4-thiazol-4-ylphenyl)methyl]pyrazolo[3,4-b]pyridine-6-carboxamide;   1-methyl-N-tetrahydropyran-4-yl-4-[(4-thiazol-4-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclobutyl]-1-methyl-4-[(4-thiazol-4-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]-N-tetrahydropyran-4-yl-thieno[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[(4-pyrazol-1-ylphenyl)methyl]-N-tetrahydropyran-4-yl-pyrazolo[3,4-b]pyridine-6-carboxamide;   1-methyl-N-(2-oxaspiro[3.3]heptan-6-yl)-4-[(4-pyrazol-1-ylphenyl)methyl]pyrazolo[3,4-b]pyridine-6-carboxamide;   N-[(3R,4S)-3-hydroxytetrahydropyran-4-yl]-1-methyl-4-[(4-pyrazol-1-ylphenyl)methyl]pyrazolo[3,4-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-4-[(4-pyrazol-1-ylphenyl)methyl]pyrazolo[3,4-b]pyridine-6-carboxamide;   1-ethyl-N-[(3R,4S)-3-hydroxytetrahydropyran-4-yl]-4-[(4-pyrazol-1-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-ethyl-N-[(1S,2S)-2-hydroxycyclohexyl]-4-[(4-pyrazol-1-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-ethyl-4-[(4-pyrazol-1-ylphenyl)methyl]-N-tetrahydropyran-4-yl-pyrrolo[2,3-b]pyridine-6-carboxamide;   1-ethyl-N-(2-oxaspiro[3.3]heptan-6-yl)-4-[(4-pyrazol-1-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-ethyl-N-[(1S,2S)-2-hydroxycyclobutyl]-4-[(4-pyrazol-1-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-ethyl-N-[(1S,2S)-2-hydroxycyclopentyl]-4-[(4-pyrazol-1-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-ethyl-N-[(1S,2S)-2-hydroxycycloheptyl]-4-[(4-pyrazol-1-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(3R,4S)-3-hydroxytetrahydropyran-4-yl]-1-methyl-4-[(4-pyrazol-1-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-4-[(4-pyrazol-1-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[(4-pyrazol-1-ylphenyl)methyl]-N-tetrahydropyran-4-yl-pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-N-(2-oxaspiro[3.3]heptan-6-yl)-4-[(4-pyrazol-1-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclobutyl]-1-methyl-4-[(4-pyrazol-1-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(3R,4S)-3-hydroxytetrahydropyran-4-yl]-1-methyl-4-[(4-thiazol-4-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-4-[(4-thiazol-4-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-N-(2-oxaspiro[3.3]heptan-6-yl)-4-[(4-thiazol-4-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-(2,6-dimethyltetrahydropyran-4-yl)-1-methyl-4-[(4-thiazol-4-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-(2,2-dimethyltetrahydropyran-4-yl)-1-methyl-4-[(4-thiazol-4-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-N-(tetrahydropyran-4-ylmethyl)-4-[(4-thiazol-4-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(3R,4S)-3-hydroxytetrahydropyran-4-yl]-1-methyl-4-[(4-thiazol-4-ylphenyl)methyl]pyrazolo[3,4-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-4-[(4-thiazol-4-ylphenyl)methyl]pyrazolo[3,4-b]pyridine-6-carboxamide;   1-methyl-N-(tetrahydropyran-4-ylmethyl)-4-[(4-thiazol-4-ylphenyl)methyl]pyrazolo[3,4-b]pyridine-6-carboxamide;   1-methyl-N-(2-oxaspiro[3.3]heptan-6-yl)-4-[(4-thiazol-4-ylphenyl)methyl]pyrazolo[3,4-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclobutyl]-1-methyl-4-[(4-thiazol-4-ylphenyl)methyl]pyrazolo[3,4-b]pyridine-6-carboxamide;   1-methyl-N-[(3R)-tetrahydropyran-3-yl]-4-[(4-thiazol-4-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-N-[(3S)-tetrahydrofuran-3-yl]-4-[(4-thiazol-4-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-N-[(3R)-tetrahydrofuran-3-yl]-4-[(4-thiazol-4-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-N-(oxetan-3-yl)-4-[(4-thiazol-4-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-N-[1-(oxetan-3-yl)azetidin-3-yl]-4-[(4-thiazol-4-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(3R,4S)-3-hydroxytetrahydropyran-4-yl]-1-methyl-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-tetrahydropyran-4-yl-pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-(2-oxaspiro[3.3]heptan-6-yl)pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1R,2R)-2-hydroxycyclobutyl]-1-methyl-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1R,2R)-2-hydroxycyclopentyl]-1-methyl-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-(tetrahydropyran-4-ylmethyl)pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-(oxetan-3-yl)pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(3R,4S)-3-hydroxytetrahydropyran-4-yl]-1-methyl-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]-N-tetrahydropyran-4-yl-pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]-N-(2-oxaspiro[3.3]heptan-6-yl)pyrrolo[2,3-b]pyridine-6-carboxamide;   N-(2,2-dimethyltetrahydropyran-4-yl)-1-methyl-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclobutyl]-1-methyl-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(3R,4S)-3-hydroxytetrahydropyran-4-yl]-1-methyl-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]-N-tetrahydropyran-4-yl-pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]-N-(2-oxaspiro[3.3]heptan-6-yl)pyrrolo[2,3-b]pyridine-6-carboxamide;   N-(2,2-dimethyltetrahydropyran-4-yl)-1-methyl-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclopentyl]-1-methyl-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclobutyl]-1-methyl-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]-N-(tetrahydropyran-4-ylmethyl)pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(3R,4S)-3-hydroxytetrahydropyran-4-yl]-1-methyl-4-[(4-thiazol-2-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-4-[(4-thiazol-2-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-N-tetrahydropyran-4-yl-4-[(4-thiazol-2-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-N-(2-oxaspiro[3.3]heptan-6-yl)-4-[(4-thiazol-2-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclobutyl]-1-methyl-4-[(4-thiazol-2-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclopentyl]-1-methyl-4-[(4-thiazol-2-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(2S,6R)-2,6-dimethyltetrahydropyran-4-yl]-1-methyl-4-[(4-thiazol-2-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-(2,2-dimethyltetrahydropyran-4-yl)-1-methyl-4-[(4-thiazol-2-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-(3,3-dimethyltetrahydropyran-4-yl)-1-methyl-4-[(4-thiazol-2-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-N-(tetrahydropyran-4-ylmethyl)-4-[(4-thiazol-2-ylphenyl)methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-4-[(4-pyrazol-1-ylphenyl)methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-[(3R,4S)-3-hydroxytetrahydropyran-4-yl]-4-[(4-pyrazol-1-ylphenyl)methyl]thieno[2,3-b]pyridine-6-carboxamide;   4-[(4-pyrazol-1-ylphenyl)methyl]-N-tetrahydropyran-4-yl-thieno[2,3-b]pyridine-6-carboxamide;   N-(2,2-dimethyltetrahydropyran-4-yl)-4-[(4-pyrazol-1-ylphenyl)methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2,6-dimethyltetrahydropyran-4-yl)-4-[(4-pyrazol-1-ylphenyl)methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(3,3-dimethyltetrahydropyran-4-yl)-4-[(4-pyrazol-1-ylphenyl)methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(3-methyltetrahydropyran-4-yl)-4-[(4-pyrazol-1-ylphenyl)methyl]thieno[2,3-b]pyridine-6-carboxamide;   4-[(4-pyrazol-1-ylphenyl)methyl]-N-(tetrahydropyran-4-ylmethyl)thieno[2,3-b]pyridine-6-carboxamide;   4-[(4-pyrazol-1-ylphenyl)methyl]-N-[(3S)-tetrahydrofuran-3-yl]thieno[2,3-b]pyridine-6-carboxamide;   4-[(4-pyrazol-1-ylphenyl)methyl]-N-[(3R)-tetrahydrofuran-3-yl]thieno[2,3-b]pyridine-6-carboxamide;   4-[(4-pyrazol-1-ylphenyl)methyl]-N-(tetrahydrofuran-3-ylmethyl)thieno[2,3-b]pyridine-6-carboxamide;   N-(2-oxaspiro[3.3]heptan-6-yl)-4-[(4-pyrazol-1-ylphenyl)methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(oxetan-3-yl)-4-[(4-pyrazol-1-ylphenyl)methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(3-fluorocyclobutyl)-4-[(4-pyrazol-1-ylphenyl)methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(3,3-difluorocyclobutyl)-4-[(4-pyrazol-1-ylphenyl)methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(azetidin-2-ylmethyl)-4-[(4-pyrazol-1-ylphenyl)methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2-methoxyethyl)-4-[(4-pyrazol-1-ylphenyl)methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2-methoxy-1-methyl-ethyl)-4-[(4-pyrazol-1-ylphenyl)methyl]thieno[2,3-b]pyridine-6-carboxamide;   4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-tetrahydropyran-4-yl-thieno[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-[(3R,4S)-3-hydroxytetrahydropyran-4-yl]-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2,2-dimethyltetrahydropyran-4-yl)-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2,6-dimethyltetrahydropyran-4-yl)-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(3,3-dimethyltetrahydropyran-4-yl)-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-(3-methyltetrahydropyran-4-yl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-(tetrahydropyran-4-ylmethyl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-(tetrahydrofuran-3-ylmethyl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-(2-oxaspiro[3.3]heptan-6-yl)thieno[2,3-b]pyridine-6-carboxamide;   N-(3-fluorocyclobutyl)-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(3,3-difluorocyclobutyl)-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2-methoxyethyl)-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2-methoxy-1-methyl-ethyl)-4-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]-N-tetrahydropyran-4-yl-thieno[2,3-b]pyridine-6-carboxamide;   N-(2,2-dimethyltetrahydropyran-4-yl)-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2,6-dimethyltetrahydropyran-4-yl)-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(3,3-dimethyltetrahydropyran-4-yl)-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]-N-(3-methyltetrahydropyran-4-yl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]-N-(tetrahydropyran-4-ylmethyl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]-N-(tetrahydrofuran-3-ylmethyl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]-N-(2-oxaspiro[3.3]heptan-6-yl)thieno[2,3-b]pyridine-6-carboxamide;   N-(3-fluorocyclobutyl)-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2-methoxyethyl)-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2-methoxy-1-methyl-ethyl)-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]-N-tetrahydropyran-4-yl-thieno[2,3-b]pyridine-6-carboxamide;   N-(2,2-dimethyltetrahydropyran-4-yl)-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2,6-dimethyltetrahydropyran-4-yl)-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(3,3-dimethyltetrahydropyran-4-yl)-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]-N-(3-methyltetrahydropyran-4-yl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]-N-(tetrahydropyran-4-ylmethyl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]-N-[(3S)-tetrahydrofuran-3-yl]thieno[2,3-b]pyridine-6-carboxamide;   4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]-N-[(3R)-tetrahydrofuran-3-yl]thieno[2,3-b]pyridine-6-carboxamide;   4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]-N-(tetrahydrofuran-3-ylmethyl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]-N-(2-oxaspiro[3.3]heptan-6-yl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]-N-(oxetan-3-yl)thieno[2,3-b]pyridine-6-carboxamide;   N-(3-fluorocyclobutyl)-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(3,3-difluorocyclobutyl)-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2-methoxyethyl)-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2-methoxy-1-methyl-ethyl)-4-[[6-(1-methylpyrazol-4-yl)-3-pyridyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-[(3R,4S)-3-hydroxytetrahydropyran-4-yl]-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2,2-dimethyltetrahydropyran-4-yl)-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2,6-dimethyltetrahydropyran-4-yl)-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(3,3-dimethyltetrahydropyran-4-yl)-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]-N-(3-methyltetrahydropyran-4-yl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]-N-(tetrahydropyran-4-ylmethyl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]-N-[(3S)-tetrahydrofuran-3-yl]thieno[2,3-b]pyridine-6-carboxamide;   4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]-N-[(3R)-tetrahydrofuran-3-yl]thieno[2,3-b]pyridine-6-carboxamide;   4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]-N-(tetrahydrofuran-3-ylmethyl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]-N-(2-oxaspiro[3.3]heptan-6-yl)thieno[2,3-b]pyridine-6-carboxamide;   4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]-N-(3-methyloxetan-3-yl)thieno[2,3-b]pyridine-6-carboxamide;   N-(3-fluorocyclobutyl)-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(azetidin-2-ylmethyl)-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2-methoxyethyl)-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   N-(2-methoxy-1-methyl-ethyl)-4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]thieno[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]-N-tetrahydropyran-4-yl-pyrrolo[2,3-b]pyridine-6-carboxamide;   N-(2,2-dimethyltetrahydropyran-4-yl)-1-methyl-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-(3,3-dimethyltetrahydropyran-4-yl)-1-methyl-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-(2,6-dimethyltetrahydropyran-4-yl)-1-methyl-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]-N-(2-oxaspiro[3.3]heptan-6-yl)pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]-N-(tetrahydropyran-4-ylmethyl)pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]-N-(tetrahydrofuran-3-ylmethyl)pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-N-(3-methyloxetan-3-yl)-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclopentyl]-1-methyl-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-(3,3-difluorocyclobutyl)-1-methyl-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   N-[(1S,2S)-2-hydroxycyclobutyl]-1-methyl-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide;   1-methyl-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]-N-(1-tetrahydrofuran-2-ylethyl)pyrrolo[2,3-b]pyridine-6-carboxamide; and   1-methyl-4-[[6-(1-methylpyrazol-3-yl)-3-pyridyl]methyl]-N-[[(2S)-tetrahydrofuran-2-yl]methyl]pyrrolo[2,3-b]pyridine-6-carboxamide,   or a pharmaceutically acceptable salt thereof.   
     
     
         25 . A pharmaceutical composition comprising a therapeutically effective amount of at least one compound of any one of  claims 1 - 24 , or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. 
     
     
         26 . A method for the treatment of a disorder associated with muscarinic acetylcholine receptor activity in a mammal, comprising administering to the mammal an effective amount of a compound of any one of  claims 1 - 24 , or a pharmaceutically acceptable salt thereof. 
     
     
         27 . The method of  claim 26 , wherein the mammal is human. 
     
     
         28 . The method of  claim 26 , wherein the muscarinic acetylcholine receptor is mAChR M 1 . 
     
     
         29 . The method of  claim 26 , wherein the mammal has been diagnosed with a need for treatment of the disorder prior to the administering step. 
     
     
         30 . The method of  claim 26 , further comprising the step of identifying a mammal in need of treatment of the disorder. 
     
     
         31 . The method of  claim 26 , wherein the disorder is a neurological disorder or psychiatric disorder, or a combination thereof. 
     
     
         32 . The method of  claim 26 , wherein the disorder is psychosis, schizophrenia, conduct disorder, disruptive behavior disorder, bipolar disorder, psychotic episodes of anxiety, anxiety associated with psychosis, psychotic mood disorders, severe major depressive disorder, mood disorders associated with psychotic disorders, acute mania, depression associated with bipolar disorder, mood disorders associated with schizophrenia, behavioral manifestations of mental retardation, conduct disorder, autistic disorder, movement disorders, Tourette's syndrome, akinetic-rigid syndrome, movement disorders associated with Parkinson's disease, tardive dyskinesia, drug induced and neurodegeneration based dyskinesias, attention deficit hyperactivity disorder, cognitive disorders, dementias, or memory disorders, or a combination thereof. 
     
     
         33 . The method of  claim 26 , wherein the disorder is Alzheimer's disease, schizophrenia, a sleep disorder, a pain disorder, or a cognitive disorder, or a combination thereof. 
     
     
         34 . The method of  claim 33 , wherein the pain disorder is neuropathic pain, central pain syndrome, postsurgical pain syndrome, bone and joint pain, repetitive motion pain, dental pain, cancer pain, myofascial pain, perioperative pain, chronic pain, dysmennorhea, inflammatory pain, headache, migraine headache, cluster headache, headache, primary hyperalgesia, secondary hyperalgesis, primary allodynia, secondary allodynia, or a combination thereof.