Tetracyclic azepinoindole compounds

Abstract

The present invention provides compounds of formula I: wherein R 1 , R 2 , X and Y have any of the values defined in the specification, as well as pharmaceutical compositions comprising the compounds. The invention also provides therapeutic methods as well as processes and intermediates useful for preparing compounds of formula (I).

1 . A compound of formula I:  
     
       
         
         
             
             
         
       
     
     wherein, 
 each R 1  is independently hydroxy, nitro, halo, cyano, trifluoromethyl, trifluoromethoxy, C 1-7 alkyl, C 1-7 alkoxy, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, C 1-7 alkanoyloxy, aryl, heteroaryl, —S(O) m NR a R b , NR c R d , —S(O) m R e , or —C(═O)NR a R b , wherein any C 1-7 alkyl, C 1-7 alkoxy, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, or C 1-7 alkanoyloxy of R 1  is optionally partially unsaturated and is optionally substituted with aryl, aryloxy, heteroaryl, heteroaryloxy, hydroxy, nitro, halo, cyano, C 1-7 alkoxy, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, C 1-7 alkanoyloxy, —S(O) m R e , —S(O) m NR a NR c R d , or —C(═O)NR a R b ;  
 R 2  is hydrogen, C 1-7 alkyl, C 1-7 alkanoyl, arylcarbonyl, aryl, (aryl)C 1-7 alkyl, C 1-7 alkoxycarbonyl, aryloxycarbonyl, arylsulfonyl, or (aryl)C 1-7 alkoxycarbonyl;  
 X and Y together are a 2, 3, or 4 membered saturated or partially unsaturated chain comprising one or more carbon atoms and optionally comprising one oxy (−O—), thio (−S—), sulfinyl (−SO—), sulfonyl (S(O) 2 —), or NR f  in the chain; wherein the chain is optionally substituted on each carbon with oxo (═O), thioxo (═S), —NR q R f , —S(O) p R s , or —OR t , or with one or two substituents independently selected from the group consisting of C 1-7 alkyl, (C 1-7 alkoxy)C 1-7 alkyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, (heteroaryl)C 1-7 alkyl, and (aryl)oxyC 1-7 alkyl; or wherein the chain is optionally substituted on a carbon with a 4, 5, or 6 membered spirocyclic carbon ring; or wherein the chain is optionally substituted on two adjacent atoms with a 2, 3, or 4 membered alkylene chain (e.g. —CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, or —CH 2 CH 2 CH 2 CH 2 —) forming a ring that is fused to the ring comprising X and Y;  
 each m is independently 0, 1, or 2;  
 n is 0, 1, 2, or 3;  
 p is 0, 1, or 2;  
 each R a  and R b  is independently hydrogen, C 1-7 alkyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, or (heteroaryl)C 1-7 alkyl; or R a  and R b  together with the nitrogen to which they are attached form a pyrrolidino, piperidino, morpholino, or thiomorpholino ring;  
 each R a  and R d  is independently hydrogen, C 1-7 alkyl, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, (heteroaryl)C 1-7 alkyl, arylcarbonyl, heteroarylcarbonyl, aryloxycarbonyl, or heteroaryloxycarbonyl; or R c  and R d  together with the nitrogen to which they are attached form a pyrrolidino, piperidino, morpholino, or thiomorpholino ring;  
 each R e  is independently hydrogen, C 1-7 alkyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, or (heteroaryl)C 17 alkyl;  
 R f  is hydrogen, C 1-7 alkyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, (heteroaryl)C 1-7 alkyl, or is a bond to a 2, 3, or 4 membered alkylene chain that forms a ring that is fused to the ring comprising X and Y;  
 each R q  and R a  is independently hydrogen, C 1-7 alkyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, or (heteroaryl)C 1-7 alkyl; or R q  and R r  together with the nitrogen to which they are attached form a pyrrolidino, piperidino, morpholino, or thiomorpholino ring;  
 R s  is C 1-7 alkyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, or (heteroaryl)C 1-7 alkyl; and  
 R t  is hydrogen, C 1-7 alkyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, or (heteroaryl)C 1-7 alkyl;  
 wherein any aryl or heteroaryl ring of R 1 , R 2 , X, Y, R a -R f , or R q -R t  is optionally substituted with one or more (e.g. 1, 2, 3, or 4) substituents independently selected from halo, hydroxy, cyano, nitro, trifluoromethyl, trifluoromethoxy, C 1-7 alkyl, C 1-7 alkoxy, phenyl, sulfonyl, NR j R k , or —C(═O)NR j R k , wherein each R j  and R k  is independently hydrogen, C 1-7 alkyl, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, aryl, (aryl)C 1-7 alkyl, arylcarbonyl, or aryloxycarbonyl; or R j  and R k  together with the nitrogen to which they are attached form a pyrrolidino, piperidino, morpholino, or thiomorpholino ring;  
 or a pharmaceutically acceptable salt thereof;  
 provided Y is not oxy, thio, sulfinyl or NR f , and  
 provided X and Y together are not a 2-membered unsaturated chain; and  
 provided no carbon of X and Y is bonded to more than one oxy, thio, sulfinyl, or NR f .  
 
   
   
       2 . The compound of  claim 1  wherein each R 1  is independently hydroxy, nitro, halo, cyano, trifluoromethyl, trifluoromethoxy, C 1-7 alkyl, C 1-7 alkoxy, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, C 1-7 alkanoyloxy, aryl, heteroaryl, —S(O) m NR a R b , NR c R d , —S(O) m R e , or —C(═O)NR a R b , wherein any C 1-7 alkyl, C 1-7 alkoxy, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, or C 1-7 alkanoyloxy of R 1  is optionally substituted with aryl, aryloxy, heteroaryl, heteroaryloxy, hydroxy, nitro, halo, cyano, C 1-7 alkoxy, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, C 1-7 alkanoyloxy, —S(O) m R e , —S(O) m NR a R b , NR c R d , or —C(═O)NR a R b .  
   
   
       3 . The compound of  claim 1  wherein each R 1  is independently hydroxy, nitro, halo, cyano, trifluoromethyl, tifluoromethoxy, C 1-7 alkyl, C 1-7 alkoxy, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, C 1-7 alkanoyloxy, aryl, heteroaryl, —S(O) m NR a R b , NR c R d , —S(O) m R c , or —C(═O)NR a R b , wherein any C 1-7 alkyl or C 1-7 alkoxy of R 1  is optionally substituted with aryl, aryloxy, heteroaryl, heteroaryloxy, hydroxy, nitro, halo, cyano, C 1-7 alkoxy, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, C 1-7 alkanoyloxy, —S(O) m R c , —S(O) m NR a R b , NR c R d , or —C(═O)NR a R b .  
   
   
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       18 . The compound of  claim 1  wherein X is —O—, —S—, or —C(R g )(R h )—, wherein R g  and R h  are each independently hydrogen, C 1-7 alkyl, (C 1-7 alkoxy)C 1-7 alkyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, (heteroaryl)C 1-7 alkyl or (aryl)oxyC 1-7 alkyl, or R g  and R h  together are oxo.  
   
   
       19 . The compound of  claim 1  wherein Y is —C(R g )(R h )—, —C(R g )(R h )C(R g )(R h )—, —C(R g )(R h )C(R g )(R h )C(R g )(R h —, —C(R g )(R h )C(═O)—, —(R g (R h )C(R g (R h )C(═O)—, —C(═O)C(R g )(R h )—, or —C(═O)C(R g )(R h )C(R g )(R h )—, and each R g  and R h  is independently hydrogen or C 1-7 alkyl.  
   
   
       20 . The compound of  claim 1  wherein X is —O—, —S—, or —C(R g )(R h )—; and Y is —C(R g )(R h )C(═O)—, or —C(R g )(R h )C(R g )(R h )—, wherein each R g  and R h  is independently hydrogen or C 1-7 alkyl.  
   
   
       21 . The compound of  claim 1  wherein X is —O— or —S—; and Y is —C(R g )(R h )C(═O)—, —C(═O)C(R g )(R h )—, or —C(R g )(R h )C(R g )(R h )—, wherein each R g  and R h  is independently hydrogen or C 1-7 alkyl.  
   
   
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       32 . The compound of  claim 1  which is: 
 5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    2-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5)pyrrolo(3,2,1-ij]quinoline;    1-methoxy-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    2-fluoro-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    6-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    (+)-6-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    (−)-6-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    (+)-5-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    (−)-5-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    (+)-4-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    (−)-4-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4,5,8,9,10,11-hexahydro-7H-azepino(4,5-b]pyrrolo[3,2,1-hi]indole;    2-fluoro-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    2-methoxy-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    5-methyl-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    4,5-dimethyl-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    2,3,4,5,8b,9,10,11,12,12a-decahydro-1H-azepino[4′,5′:4,5]pyrrolo[3,2,1-jk]carbazole;    1-chloro-2-fluoro-4,5,8,9,10,11-hexahydro-7-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    1-chloro-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    2-chloro-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    2-fluoro-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    2-chloro-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′;4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    6-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino(4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    2-fluoro-6-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    2,3-dichloro-6-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    6-propyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    6-(trifluoromethyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-ol;    4-methoxy-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    10-benzoyl-4-phenoxy-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline; or    4-phenoxy-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    or a pharmaceutically acceptable salt thereof.    
   
   
       33 . The compound 1,2,8,9,10,11-hexahydro-7H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole; or a pharmaceutically acceptable salt thereof.  
   
   
       34 . The compound of  claim 1  which is: 
 1-fluoro-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    3-fluoro-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    1-bromo-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    2-bromo-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    3-bromo-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    3-chloro-1-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    2-chloro-1-fluoro-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    1-methoxy-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole,    3-methoxy-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    4-methyl-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    1-(trifluoromethyl)-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    2-(trifluoromethyl)-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    3-(trifluoromethyl)-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    4-benzyloxy-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo(3,2,1-ij]quinoline;    4-(3-chlorophenoxy)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-(2-chlorophenoxy)5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-(4-methoxyphenoxy)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-(3-methoxyphenoxy)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-(2-methoxyphenoxy)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-(4-bromo-2-methoxyphenoxy)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-amine;    N-phenyl-5,6,9,10,11,12-hexahydro-4H8H-azepino[4′,5′;4,5]pyrrolo[3,2,1-ij]quinolin-4-amine;    N-(4-chlorophenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-4amine;    N-(3-chlorophenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-amine;    N-(2-chlorophenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5}pyrrolo[3,2,1-ij]quinolin-4-amine;    N-(4-methoxyphenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-amine;    N-(3-methoxyphenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-amine;    N-(2-methoxyphenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-amine;    N-(4-bromo-2-methoxyphenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-amine;    5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-4-thione;    4-(phenylsulfonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-(4-chlorophenylsulfonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-(3-chlorophenylsulfonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-(2-chlorophenylsulfonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-(4-methoxyphenylsulfonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-(3-methoxyphenylsulfonyl-5,,6, 10,111,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-(2-methoxyphenylsulfonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-(4-bromo-2-methoxyphenylsulfonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-5-ol;    5-methoxy-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-benzyloxy-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-phenoxy-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-(4-chlorophenoxy)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-(3-chlorophenoxy)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5)pyrrolo[3,2,1-ij]quinoline;    5-(2-chlorophenoxy)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-(4-methoxyphenoxy)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-(3-methoxyphenoxy)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-(2-methoxyphenoxy)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-(4-bromo-2-methoxyphenoxy)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-5-amine;    N-phenyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-5-amine;    N-(4-chlorophenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-5-amine;    N-(3chlorophenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-5-amine;    N-(2-chlorophenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-5-amine;    N-(4-methoxyphenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-5-amine;    N-(3-methoxyphenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-5-amine;    N-(2-methoxyphenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-5-amine;    N-(4-bromo-2-methoxyphenyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-5-amine;    5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-5-thione;    5-(phenylsulfonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-(4-chlorophenylsulfonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-(3-chlorophenylsulfonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-(2chlorophenylsulfonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-(4-methoxyphenylsulfonyl)5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-(3-methoxyphenylsulfonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-(2-methoxyphenylsulfonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    5-(4-bromo-2-methoxyphenylsufonyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    4-(4-chlorophenoxy)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(4-fluorophenoxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(3-fluorophenoxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H4, 8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(2-fluorophenoxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(4-chlorophenoxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(3-chlorophenoxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;      1  -[2-(2-chlorophenoxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(4-bromophenoxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(3-bromophenoxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(2-bromophenoxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(4-methoxyphenoxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(3-methoxyphenoxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(2-methoxyphenoxy)ethoxy}-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(4-methylphenoxy)ethoxy]-5.6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(3-methylphenoxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(2-methylphenoxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(1-naphthyloxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-(2-naphthyloxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-([1,1′-biphenyl]-4-yloxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-([1,1′-biphenyl]-3-yloxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-[2-([1,1′-biphenyl]-2-yloxy)ethoxy]-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-{2-[4-(trifluoromethoxy)phenoxy]ethoxy}-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5)pyrrolo[3,2,1-ij]quinoline;    1-{2-[3-(trifluoromethoxy)phenoxy]ethoxy}-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-{2-[2-(trifluoromethoxy)phenoxy]ethoxy}-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline;    1-{2-[4(trifluoromethyl)phenoxy]ethoxy}-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5)pyrrolo[3,2,1-ij]quinoline;    1-{2-[3-(trifluoromethyl)phenoxy]ethoxy}-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline, or    1-{2-[2-(trifluoromethyl)phenoxy]ethoxy}-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline; or a pharmaceutically acceptable salt thereof.    
   
   
       35 . A pharmaceutical composition comprising a compound of  claim 1  and a pharmaceutically acceptable excipient.  
   
   
       36 . A method for treating a disease or condition in a mammal wherein the 5-HT receptor is implicated and modulation of 5-HT function is desired comprising administering a therapeutically effective amount of a compound of  claim 1  to the mammal.  
   
   
       37 . The method of  claim 36  wherein the disease or condition is anxiety, obesity, depression, schizophrenia, a stress related disease, panic disorder, a phobia, obsessive compulsive disorder, post-traumatic-stress syndrome, immune system depression, a stress induced problem with the gastrointestinal or cardiovascular system, or sexual dysfunction.  
   
   
       38 . The method of  claim 37  wherein the disease is anxiety, obesity, depression, or a stress related disease.  
   
   
       39 . A method for treating or preventing a disease or disorder of the central nervous system in a mammal comprising administering a therapeutically effective amount of a compound of  claim 1 , or a pharmaceutically acceptable salt thereof to the mammal.  
   
   
       40 . The method of  claim 39  wherein the disease or disorder of the central nervous system is obesity, depression, schizophrenia, schizophreniform disorder, schizoaffective disorder, delusional disorder, a stress related disease, panic disorder, a phobia, obsessive compulsive disorder, post-traumatic-stress syndrome, immune system depression, a stress induced problem with the urinary, gastrointestinal or cardiovascular system, neurodegenerative disorders, autism, chemotherapy-induced vomiting, hypertension, migraine, headaches, cluster headaches, sexual dysfunction, addictive disorder and withdrawal syndrome, an adjustment disorder, an age-associated learning and mental disorder, anorexia nervosa, apathy, an attention-deficit disorder due to general medical conditions, attention-deficit hyperactivity disorder, behavioral disturbance, bipolar disorder, bulimia nervosa, chronic fatigue syndrome, conduct disorder, cyclothymic disorder, dysthymic disorder, fibromyalgia and other somatoform disorders, generalized anxiety disorder, an inhalation disorder, an intoxication disorder, movement disorder, oppositional defiant disorder, peripheral neuropathy, post-traumatic stress disorder, premenstrual dysphoric disorder, a psychotic disorder, mood disorder, seasonal affective disorder, a sleep disorder, a specific development disorder, agitation disorder, selective serotonin reuptake inhibition syndrome, or a Tic disorder.  
   
   
       41 . A compound of formula I:  
     
       
         
         
             
             
         
       
     
     wherein, 
 each R 1  is independently hydroxy, nitro, halo, cyano, trifluoromethyl, trifluoromethoxy, C 1-7 alkyl, C 1-7 alkoxy, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, C 1-7 alkanoyloxy, aryl, heteroaryl, —S(O) m NR a R b , NR c R d , —S(O) m R e , or —C(═O)NR a R b , wherein any C 1-7 alkyl, C 1-7 alkoxy, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, or C 1-7 alkanoyloxy of R 1  is optionally partially unsaturated and is optionally substituted with aryl, aryloxy, heteroaryl, heteroaryloxy, hydroxy, nitro, halo, cyano, C 1-7 alkoxy, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, C 1-7 alkanoyloxy, —S(O) m R e , —S(O) m NR a R b , NR c R d , or —C(═O)NR a R b ;  
 R 2  is a suitable protecting group;  
 X and Y together are a 2, 3 or 4 membered saturated or partially unsaturated chain comprising one or more carbon atoms and optionally comprising one oxy (−O—), thio (−S—), sulfinyl (−SO—), sulfonyl (S(O) 2 —), or NR f  in the chain; wherein the chain is optionally substituted on each carbon with oxo (═O), thioxo (═S), —NR q R t , —S(O) p R s , or —OR t  or with one or two substituents independently selected from the group consisting of C 1-7 alkyl, (C 1-7 alkoxy)C 1-7 alkylaryl, (aryl)C 1-7 alkyl, heteroaryl (heteroaryl)C 1-7 alkyl, and (aryl)oxyC 1-7 alkyl; or wherein the chain is optionally substituted on a carbon with a 4, 5, or 6 membered spirocyclic carbon ring; or wherein the chain is optionally substituted on two adjacent atoms with a 2, 3, or 4 membered alkylene chain (e.g. —CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, or —CH 2 CH 2 CH 2 CH 2 —) forming a ring that is fused to the ring comprising X and Y;  
 each m is independently 0, 1, or 2;  
 n is 0, 1, 2, or 3;  
 p is 0, 1 or 2;  
 each R a  and R b  is independently hydrogen, C 1-7 allyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, or (heteroaryl)C 1-7 alkyl; or R a  and R b  together with the nitrogen to which they are attached form a pyrrolidino, piperidino, morpholino, or thiomorpholino ring;  
 each R a  and R d  is independently hydrogen, C 1-7 alkyl, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, (heteroaryl)C 1-7 alkyl, arylcarbonyl, heteroarylcarbonyl, aryloxycarbonyl, or heteroaryloxycarbonyl; or R c  and R d  together with the nitrogen to which they are attached form a pyrrolidino, piperidino, morpholino, or thiomorpholino ring;  
 each R a  is independently hydrogen, C 1-7 alkyl, aryl (aryl)C 1-7 alkyl, heteroaryl, or (heteroaryl)C 1-7 alkyl;  
 R f  is hydrogen, C 1-7 alkyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, (heteroaryl)C 1-7 alkyl or is a bond to a 2, 3, or 4 membered alkylene chain that forms a ring that is fused to the ring comprising X and Y;  
 each R q  and R r  is independently hydrogen, C 1-7 alkyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, or (heteroaryl)C 1-7 alkyl; or R q  and R r  together with the nitrogen to which they are attached form a pyrrolidino, piperidino, morpholino, or thiomorpholino ring;  
 R s  is C 1-7 alkyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, or (heteroaryl)C 1-7 alkyl; and  
 R t  is hydrogen, C 1-7 alkyl, aryl, (aryl)C 1-7 alkyl, heteroaryl, or (heteroaryl)C 1-7 alkyl;  
 wherein any aryl or heteroaryl ring of R 1 , R 2 , X, Y, R a -R f ; or R q -R t  is optionally substituted with one or more (e.g. 1, 2, 3, or 4) substituents independently selected from halo, hydroxy, cyano, nitro, trifluoromethyl, trifluoromethoxy, C 1-7 alkyl, C 1-7 alkoxy, phenyl, sulfonyl, NR j R k , or —C(═O)NR j R k  ,; wherein each R j  and R k  is independently hydrogen, C 1-7 alkyl, C 1-7 alkanoyl, C 1-7 alkoxycarbonyl, aryl, (aryl)C 1-7 alkyl, arylcarbonyl, or aryloxycarbonyl; or  
 R j  and R k  together with the nitrogen to which they are attached form a pyrrolidino, piperidino, morpholino, or thiomorpholino ring;  
 or a pharmaceutically acceptable salt thereof;  
 provided Y is not oxy, thio, sulfinyl, or NR f′ , and  
 provided X and Y together are not a 2-membered unsaturated chain; and  
 provided no carbon of X and Y is bonded to more than one oxy, thio, sulfinyl, or NR f .  
 
   
   
       42 . The compound of  claim 41  wherein R 2  is C 1-4 alkyl, C 1-4 alkanoyl, arylcarbonyl, (aryl)C 1-2 alkyl, C 1-4 alkoxycarbonyl, aryloxycarbonyl, arylsulfonyl, or (aryl)methoxycarbonyl, wherein any aryl is optionaly substituted with 1, 2, or 3 substituents independently selected from C 1-4 alkyl and trifluoromethyl.  
   
   
       43 . The compound of  claim 41 , wherein R 2  is methyl, ethyl, propyl, isopropyl, acetyl, tert-butoxycarbonyl, benzyloxycarbonyl, benzyl, or p-toluenesulfonyl.  
   
   
       44 . The compound of  claim 1  which is: 
 10-benzoyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    10-benzoyl-2-fluoro-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′;4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    10-benzoyl-2-chloro-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    10-benzoyl-6-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′;4,5]pyrrolo[3,2,1-ij]quinolin4-one;    10-benzoyl-2-fluoro-6-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    10-benzoyl-2,3-dichloro-6-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    10-benzoyl-6-propyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    10-benzoyl-6-(trifluoromethyl)5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin4-one;    10-benzoyl-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-ol; or    10-benzoyl-4-methoxy-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin,    
   
   
       45 . The compound of claim which is: 
 benzyl 5,6,8,9,11,12-hexahydro-4H,10H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate;    benzyl 2-methyl-5,6,8,9,11,12-hexahydro-4H,10H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate;    10-benzoyl-1-methoxy-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo-[3,2,1-ij]quinoline;    benzyl 2-fluoro-5,6,8,9,11,12-hexahydro-4H,10H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate;    benzyl 6-methyl-5,6,8,9,11,12-hexahydro-4H,10H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate;    benzyl 5-methyl-5,6,8,9,11,12-hexahydro4H,10H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate;    benzyl 4-methyl-5,6,8,9,11,12-hexahydro-4H,10H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate;    (+)-benzyl 6-methyl-5,6,8,9,11,12-hexahydro-4H,10H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate;    (−)-benzyl 6-methyl-5,6,8,9,11,12-hexahydro-4H,10H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate;    (+)-benzyl 5-methyl-5,6,8,9,11,12-hexahydro-4H,10-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate;    (−)benzyl 5-methyl-5,6,8,9,11,12-hexahydro-4H,10H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate;    (+)-benzyl 4-methyl-5,6,8,9,11,12-hexahydro-4H,10H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate;    (−)-benzyl 4-methyl-5,6,8,9,11,12-hexahydro-4H,10H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate;    benzyl 2-methyl-1,2,7,8,10,11-hexahydro-9H-azepino(4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate;    benzyl 2,2-dimethyl-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate;    benzyl 4-fluoro-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate;    benzyl 4chloro-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate;    benzyl 5-fluoro-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate;    benzyl 5-chloro-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate;    benzyl 5-methyl-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate;    benzyl 6-fluoro-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate;    benzyl 6chloro-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate; benzyl 6-methyl-1,2,6b,7,8,10,11,11a-octahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate;    benzyl 6-(trifluoromethyl)-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate;    benzyl 5,6difluoro-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylatebenzyl;    benzyl 5-chloro-6-fluoro-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole9-carboxylate;    benzyl 5-fluoro-6-chloro-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate;    benzyl 5,6-dichloro-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate;    benzyl 4,6-dichloro-1,2,7,8,10,11-hexahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate;    7-benzoyl 4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    7-benzoyl 2-fluoro-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    7-benzoyl 2-methoxy-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole;    benzyl-5-methyl-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]-7-carboxylate,    benzyl-4,5-dimethyl-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole-7-carboxylate;    benzyl-2,3,4,5,8b,9,10,11,12,12a-decahydro-1H-azepino[4′,5′:4,5]pyrrolo[3,2,1-jk]carbazole-7-carboxylate;    benzyl-1-chloro-2-fluoro-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole-7-carboxylate;    benzyl-2-chloro-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole-7-carboxylate;    benzyl-1-chloro-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole-7-carboxylate;    10-benzoyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    10-benzoyl-2-fluoro-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo-[3,2,1-ij]quinolin-4-one;    10-benzoyl-2-chloro-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo-[3,2,1-ij]quinolin-4-one;    10-benzoyl-6-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo-[3,2,1-ij]quinolin-4-one;    10-benzoyl-2-fluoro-6-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]-pyrrolo[3,2,1-ij]quinolin-4-one;    10-benzoyl-2,3-dichloro-6-methyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4═,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    10-benzoyl-6-propyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo-[3,2,1-ij]quinolin-4-one;    10-benzoyl-6-(trifluoromethyl)-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-one;    10-benzoyl-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-ol; and    10-benzoyl-4-methoxy-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline.    
   
   
       46 . (canceled)  
   
   
       47 . (canceled)