Tricyclic quinoline and quinoxaline derivatives

Abstract

The present invention relates to tricyclic quinoline and quinoxaline derivatives, to a pharmaceutical composition containing such compounds, to their use as modulators, especially agonists or partial agonists, of the 5-HT 2C receptor, their use for preparing a medicament for the prevention or treatment of conditions and disorders which respond to the modulation of 5-HT 2C receptor, and to a method for preventing or treating conditions and disorders which respond to the modulation of 5-HT 2C receptor.

We claim: 
     
         1 . A compound of the formula I 
       
         
           
           
               
               
           
         
         wherein 
         G is (CR 3a R 3b ) n ; 
         X is NR 6  or CR 7 R 8 ; 
         R 1  is selected from the group consisting of hydrogen, cyano, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, fluorinated C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, fluorinated C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, fluorinated C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy, —C(═O)R 10 , phenyl, phenyl-C 1 -C 2 -alkyl and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO 2  and optionally also 1 or 2 C═O and/or C═S groups as ring members, where the cyclic moieties in the three last-mentioned radicals may be substituted with one or more substituents R 11 ; 
         each R 2  is independently selected from the group consisting of cyano, nitro, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -alkenyl, fluorinated C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, fluorinated C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, fluorinated C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylthio, fluorinated C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, fluorinated C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, fluorinated C 1 -C 6 -alkylsulfonyl, —NR 12a R 12b , —CH 2 NR 12a R 12b ,
 —NR 12a C(O)R 10 , —C(═O)R 10 , SO 2 NR 12a R 12b , C 1 -C 6 -alkylcarbonyloxy, fluorinated C 1 -C 6 -alkylcarbonyloxy, phenyl, phenyl-C 1 -C 2 -alkyl, phenoxy, phenylsulfonyl, benzyloxy and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO, SO 2 , C═O and C═S as ring members, where the cyclic moieties in the six last-mentioned radicals may be substituted with one or more substituents R 11 ; 
 
         R 3a  and R 3b , independently of each other, are selected from the group consisting of hydrogen, cyano, nitro, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -alkenyl, fluorinated C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, fluorinated C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, fluorinated C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylthio, fluorinated C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, fluorinated C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, fluorinated C 1 -C 6 -alkylsulfonyl,
 —NR 12a R 12b , —CH 2 NR 12a R 12b , 
 —NR 12a C(O)R 10 , —C(═O)R 10 , SO 2 NR 12a R 12b , C 1 -C 6 -alkylcarbonyloxy, fluorinated C 1 -C 6 -alkylcarbonyloxy, phenyl, phenyl-C 1 -C 2 -alkyl, phenoxy, phenylsulfonyl, benzyloxy and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO, SO 2 , C═O and C═S as ring members, where the cyclic moieties in the six last-mentioned radicals may be substituted with one or more substituents R 11 ; 
 
         R 4a  and R 4b , independently of each other, are selected from the group consisting of hydrogen, cyano, nitro, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -alkenyl, fluorinated C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, fluorinated C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, fluorinated C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylthio, fluorinated C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, fluorinated C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, fluorinated C 1 -C 6 -alkylsulfonyl,
 —NR 12a R 12b , —CH 2 NR 12a R 12b , —NR 12a C(O)R 10 , —C(═O)R 10 , SO 2 NR 12a R 12b , C 1 -C 6 -alkylcarbonyloxy, fluorinated C 1 -C 6 -alkylcarbonyloxy, phenyl, phenyl-C 1 -C 2 -alkyl, phenoxy, phenylsulfonyl, benzyloxy and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO, SO 2 , C═O and C═S as ring members, where the cyclic moieties in the six last-mentioned radicals may be substituted with one or more substituents R 11 ; or 
 R 4a  and R 4b  form together a group ═O or ═S; 
 
         R 5a  and R 5b , independently of each other, are selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -alkenyl, fluorinated C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, fluorinated C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, fluorinated C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylthio, fluorinated C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, fluorinated C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, fluorinated C 1 -C 6 -alkylsulfonyl, —NR 12a R 12b , —CH 2 NR 12a R 12b , —NR 12a C(O)R 10 , —C(═O)R 10 , SO 2 NR 12a R 12b , C 1 -C 6 -alkylcarbonyloxy, fluorinated C 1 -C 6 -alkylcarbonyloxy, phenyl, phenyl-C 1 -C 2 -alkyl, phenoxy, phenylsulfonyl, benzyloxy and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO, SO 2 , C═O and C═S as ring members, where the cyclic moieties in the six last-mentioned radicals may be substituted with one or more substituents R 11 ; or
 R 5a  and R 5b , together with the carbon atom they are bound to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents R 11 ; or 
 R 5a  and R 6 , together with the atoms they are bound to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the ring may further contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents R 11 ; or 
 R 5a  and R 7 , together with the carbon atoms they are bound to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents R 11 ; 
 
         R 6  is selected from the group consisting of hydrogen, cyano, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, fluorinated C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, fluorinated C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, fluorinated C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, fluorinated C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy, —C(═O)R 10 , —SO 2 R 10 , phenyl, phenyl-C 1 -C 2 -alkyl and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO 2  and optionally also 1 or 2 C═O and/or C═S groups as ring members, where the cyclic moieties in the three last-mentioned radicals may be substituted with one or more substituents R 11 ; 
         R 7  and R 8 , independently of each other, are selected from the group consisting of deuterium, halogen, cyano, nitro, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -alkenyl, fluorinated C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, fluorinated C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, fluorinated C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylthio, fluorinated C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, fluorinated C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, fluorinated C 1 -C 6 -alkylsulfonyl,
 —NR 12a R 12b , —CH 2 NR 12a R 12b , —NR 12a C(O)R 10 , —C(═O)R 10 , SO 2 NR 12a R 12b , C 1 -C 6 -alkylcarbonyloxy, fluorinated C 1 -C 6 -alkylcarbonyloxy, phenyl, phenyl-C 1 -C 2 -alkyl, phenoxy, phenylsulfonyl, benzyloxy and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO, SO 2 , C═O and C═S as ring members, where the cyclic moieties in the six last-mentioned radicals may be substituted with one or more substituents R 11 ; or 
 R 7  and R 8 , together with the carbon atom they are bound to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents R 11 ; 
 
         each R 9  is independently selected from the group consisting of halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -alkenyl, fluorinated C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, fluorinated C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, fluorinated C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl, fluorinated C 3 -C 8 -cycloalkenyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylthio, fluorinated C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, fluorinated C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, fluorinated C 1 -C 6 -alkylsulfonyl, —NR 12a R 12b , —CH 2 NR 12a R 12b , —NR 12a C(O)R 10 , —C(═O)R 10 , SO 2 NR 12a R 12b , C 1 -C 6 -alkylcarbonyloxy, fluorinated C 1 -C 6 -alkylcarbonyloxy, phenyl, phenyl-C 1 -C 2 -alkyl, phenoxy, phenylsulfonyl, benzyloxy and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO, SO 2 , C═O and C═S as ring members, where the cyclic moieties in the six last-mentioned radicals may be substituted with one or more substituents R 11 ; or two radicals R 9  bound on neighboring carbon atoms, together with the carbon atoms they are bound to, form a 3-, 4-, 5-, 6-, 7- or 8-membered partially unsaturated or maximally unsaturated ring, where the ring may contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents R 11 ; 
         each R 10  is independently selected from the group consisting of hydrogen, cyano, hydroxy, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -alkenyl, fluorinated C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, fluorinated C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, fluorinated C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy, —NR 12a R 12b , —CH 2 NR 12a R 12b , phenyl, phenyl-C 1 -C 2 -alkyl, phenoxy, benzyloxy and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO, SO 2 , C═O and C═S as ring members, where the cyclic moieties in the five last-mentioned radicals may be substituted with one or more substituents R 11 ; 
         each R 11  is independently selected from the group consisting of halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -alkenyl, fluorinated C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, fluorinated C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, fluorinated C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylthio, fluorinated C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, fluorinated C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, fluorinated C 1 -C 6 -alkylsulfonyl, —COOH, —NR 12a R 12b , —CH 2 NR 12a R 12b , C 1 -C 6 -alkylcarbonyl, fluorinated C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, fluorinated C 1 -C 6 -alkoxycarbonyl, SO 2 NR 12a R 12b , C 1 -C 6 -alkylcarbonyloxy and fluorinated C 1 -C 6 -alkylcarbonyloxy; 
         R 12a  and R 12b , independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, cyano, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, fluorinated C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, fluorinated C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, fluorinated C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, fluorinated C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, fluorinated C 1 -C 6 -alkoxycarbonyl, phenyl and benzyl, where the phenyl moieties in the two last-mentioned radicals may carry 1, 2 or 3 substituents selected from halogen, cyano nitro, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and fluorinated C 1 -C 6 -alkoxy; or, 
         if R 12a  and R 12b  are bound to the same nitrogen atom, together with this nitrogen atom may form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the ring may further contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents selected from halogen, cyano nitro, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and fluorinated C 1 -C 6 -alkoxy; 
         a is 0, 1 or 2; 
         b is 0, 1, 2 or 3; and 
         n is 1 or 2; 
         and the N-oxides, tautomeric forms, stereoisomers and pharmaceutically acceptable salts thereof, and the compound of the general formula I, wherein at least one of the atoms has been replaced by its stable, non-radioactive isotope. 
       
     
     
         2 . The compound as claimed in  claim 1 , wherein at least one hydrogen atom has been replaced by a deuterium atom. 
     
     
         3 . The compound as claimed in any of the preceding claims, where R 1  is selected from hydrogen and C 1 -C 6 -alkyl and is preferably hydrogen. 
     
     
         4 . The compound as claimed in any of the preceding claims, where R 2  is selected from cyano, nitro, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and fluorinated C 1 -C 6 -alkoxy, and preferably from C 1 -C 6 -alkyl. 
     
     
         5 . The compound as claimed in any of the preceding claims, where R 3a  and R 3b , independently of each other, are selected from hydrogen, cyano, nitro, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and fluorinated C 1 -C 6 -alkoxy. 
     
     
         6 . The compound as claimed in  claim 5 , where R 3a  is selected from hydrogen, cyano, nitro, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and fluorinated C 1 -C 6 -alkoxy, and R 3b  is hydrogen. 
     
     
         7 . The compound as claimed in  claim 6 , where R 3a  is selected from hydrogen and methyl, and R 3b  is hydrogen. 
     
     
         8 . The compound as claimed in  claim 7 , where R 3a  and R 3b  are hydrogen. 
     
     
         9 . The compound as claimed in any of the preceding claims, where R 4a  and R 4b , independently of each other, are selected from hydrogen, C 1 -C 6 -alkyl and fluorinated C 1 -C 6 -alkyl or form together a group ═O, and are preferably hydrogen or form together a group ═O, and are in particular hydrogen. 
     
     
         10 . The compound as claimed in any of the preceding claims, where
 R 5a  is selected from hydrogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and fluorinated C 1 -C 6 -alkoxy; and in case that X is CR 7 R 8  is further selected from halogen; or
 R 5a  and R 6 , together with the atoms they are bound to, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the ring may further contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents R 11 ; or 
 R 5a  and R 7 , together with the carbon atoms they are bound to, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents R 11 ; and 
   R 5b  is selected from hydrogen and deuterium.   
     
     
         11 . The compound as claimed in  claim 10 , where
 R 5a  is selected from hydrogen, C 1 -C 6 -alkyl and fluorinated C 1 -C 6 -alkyl; and in case that X is CR 7 R 8  is further selected from halogen; or
 R 5a  and R 6  form together a group (CH 2 ), where r is 2, 3, 4 or 5; or 
 R 5a  and R 7  form together a group (CH 2 ) s , where s is 2, 3, 4 or 5; and 
   R 5b  is selected from hydrogen and deuterium.   
     
     
         12 . The compound as claimed in any of  claims 1  to  9 , where R 5a  and R 5b , together with the carbon atom they are bound to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents R 11 ; and form preferably a 5- or 6-membered saturated or partially unsaturated carbocyclic ring, and where the ring may be substituted with one or more substituents R 11 . 
     
     
         13 . The compound as claimed in any of the preceding claims, where X is NR 6 , where R 6  is as defined in  claim 1 . 
     
     
         14 . The compound as claimed in  claim 13 , where X is NR 6 , where R 6  is —SO 2 R 10  where R 10  is as defined in  claim 1 . 
     
     
         15 . The compound as claimed in  claim 14 , where R 10  is selected from C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl and phenyl, where phenyl may be substituted with 1, 2, 3, 4 or 5 radicals R 11 . 
     
     
         16 . The compound as claimed in  claim 13 , where X is NR 6 , where R 6  is selected from C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, fluorinated C 3 -C 6 -cycloalkyl, phenyl, phenyl-C 1 -C 2 -alkyl and a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO 2  and optionally also 1 or 2 C═O and/or C═S groups as ring members, where the cyclic moieties in the three last-mentioned radicals may be substituted with one or more substituents R 11 ; and is in particular phenyl-C 1 -C 2 -alkyl. 
     
     
         17 . The compound as claimed in  claim 13 , where X is NR 6 , where R 5a  and R 6 , together with the atoms they are bound to, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the ring may further contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents R 11 . 
     
     
         18 . The compound as claimed in  claim 17 , where R 5a  and R 6  form together a group (CH 2 ) r , where r is 2, 3, 4 or 5. 
     
     
         19 . The compound as claimed in any of  claims 1  to  12 , where X is CR 7 R 8 , where R 7  and R 8  are as defined in  claim 1 . 
     
     
         20 . The compound as claimed in  claim 19 , where
 R 7  and R 8 , independently of each other, are selected from the group consisting of halogen, cyano, nitro, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -alkenyl, fluorinated C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, fluorinated C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, fluorinated C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylthio, fluorinated C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, fluorinated C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, fluorinated C 1 -C 6 -alkylsulfonyl, —NR 12a R 12b , —CH 2 NR 12a R 12b , —NR 12a C(O)R 10 , —C(═O)R 10 , SO 2 NR 12a R 12b , C 1 -C 6 -alkylcarbonyloxy, fluorinated C 1 -C 6 -alkylcarbonyloxy, phenyl, phenyl-C 1 -C 2 -alkyl, phenoxy, phenylsulfonyl, benzyloxy and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO, SO 2 , C═O and C═S as ring members, where the cyclic moieties in the six last-mentioned radicals may be substituted with one or more substituents R 11 ; or   R 7  and R 8 , together with the carbon atom they are bound to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents R 11 ; or   R 5a  and R 7 , together with the carbon atoms they are bound to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents R 11 ; in which case R 8  has one of the above meanings or is deuterium.   
     
     
         21 . The compound as claimed in  claim 20 , where
 R 7  and R 8 , independently of each other, are selected from halogen, cyano, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy, phenyl, phenyl-C 1 -C 2 -alkyl, benzyloxy and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO, SO 2 , C═O and C═S as ring members, where the cyclic moieties in the four last-mentioned radicals may be substituted with one or more substituents R 11 ; or   R 7  and R 8 , together with the carbon atom they are bound to, form a 3-, 4-, 5-, 6- or 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents R 11 ; or   R 5a  and R 7 , together with the carbon atoms they are bound to, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, and where the ring may be substituted with one or more substituents R 11 ; in which case R 8  has one of the above meanings or is deuterium; and   R 5b  is selected from hydrogen and deuterium.   
     
     
         22 . The compound as claimed in  claim 21 , where
 R 7  and R 8 , independently of each other, are selected from halogen, cyano, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl and phenyl, or   R 7  and R 8 , together with the carbon atom they are bound to, form a 3-, 4-, 5-, 6- or 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may be substituted with one or more substituents R 11 ; or   R 5a  and R 7  form together a group (CH 2 ) s , where s is 2, 3, 4 or 5; in which case R 8  has one of the above meanings or is deuterium; and   R 5b  is selected from hydrogen and deuterium.   
     
     
         23 . The compound as claimed in  claim 22 , where
 R 8  is selected from halogen, cyano, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl and phenyl; and   R 7  is selected from C 1 -C 6 -alkyl and fluorinated C 1 -C 6 -alkyl, preferably from methyl and CF 3  and is in particular methyl; or   R 7  and R 8 , together with the carbon atom they are bound to, form a 3-, 4-, 5-, 6- or 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may be substituted with one or more substituents R 11 ; or   R 5a  and R 7  form together a group (CH 2 ) s , where s is 2, 3 or 4; in which case R 8  has one of the above meanings or is deuterium; and   R 5b  is selected from hydrogen and deuterium.   
     
     
         24 . The compound as claimed in any of  claims 20  to  23 , wherein the ring formed by R 7  and R 8  together with the carbon atom they are bound is a carbocyclic ring. 
     
     
         25 . The compound as claimed in  claim 24 , where R 7  and R 8 , together with the carbon atom they are bound to, form a 4-, 5- or 6-membered saturated or partially unsaturated carbocyclic ring, preferably a 4- or 5-membered saturated carbocyclic ring, in particular a 4-membered saturated carbocyclic ring, where the ring may be substituted with one or more substituents R 11 . 
     
     
         26 . The compound as claimed in any of  claims 20  to  23 , wherein the ring formed by R 7  and R 8  together with the carbon atom they are bound is a heterocyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO and SO 2  as ring members preferably containing 1 or 2 heteroatoms selected from O, S and N as ring members. 
     
     
         27 . The compound as claimed in  claim 26 , wherein the heterocyclic ring is a saturated 3-, 4- or 5-membered heterocyclic ring containing one heteroatom selected from O, S and N as ring member, where the ring may be substituted with one or more substituents R 11 , and is in particular oxetanyl which may be substituted with one or more substituents R 11 . 
     
     
         28 . The compound as claimed in any of the preceding claims, where each R 9  is independently selected from halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, fluorinated C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, fluorinated C 1 -C 6 -alkoxy and a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1 or 2 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO 2  as ring members, where the heterocyclic ring may be substituted with one or more substituents R 11 , and is in particular halogen. 
     
     
         29 . The compound as claimed in any of the preceding claims, where each R 11  is independently selected from halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and fluorinated C 1 -C 6 -alkoxy, and is in particular halogen or C 1 -C 4 -alkyl. 
     
     
         30 . The compound as claimed in any of the preceding claims, where a is 0 or 1, in particular 0. 
     
     
         31 . The compound as claimed in any of the preceding claims, where b is 0 or 1. 
     
     
         32 . The compound as claimed in any of the preceding claims, where n is 1. 
     
     
         33 . The compound as claimed in any of the preceding claims, of formula I.1 
       
         
           
           
               
               
           
         
         wherein X, R 5a , R 5b , R 9  and b are as defined in any of  claims 1  and  10  to  31 . 
       
     
     
         34 . The compound as claimed in  claim 33 , of formula I.1.1 
       
         
           
           
               
               
           
         
         wherein 
         R 9a  is H or F; and 
         R 5a , R 5b , R 6 , R 9  and b are as defined in any of  claims 1  and  10  to  31 . 
       
     
     
         35 . The compound as claimed in  claim 33 , of formula I.1.2 
       
         
           
           
               
               
           
         
         wherein 
         R 7  is selected from C 1 -C 4 -alkyl and fluorinated C 1 -C 4 -alkyl, preferably from methyl and CF 3 , and is in particular methyl; 
         R 8  is selected from C 1 -C 4 -alkyl and fluorinated C 1 -C 4 -alkyl, and preferably from methyl and CF 3 ; or 
         R 7  and R 8 , together with the carbon atom they are bound to, form a 3-, 4-, 5-, 6- or 7-membered saturated or partially unsaturated ring, where the ring may be substituted with one or more substituents R 11 ; 
         R 9a  is H or F; and 
         R 9  and b are as defined in any of  claims 1  and  10  to  31 . 
       
     
     
         36 . The compound as claimed in  claim 33 , of formula I.1.3 
       
         
           
           
               
               
           
         
         wherein R 8  is selected from deuterium, F, Cl and CN. 
       
     
     
         37 . The compound as claimed in any of  claims 1  to  32 , of formula I.2 
       
         
           
           
               
               
           
         
         wherein X, R 5a , R 5b , R 9  and b are as defined in any of  claims 1  and  10  to  31 . 
       
     
     
         38 . The compound as claimed in  claim 37 , of formula I.2.1 
       
         
           
           
               
               
           
         
         wherein 
         R 9a  is H or F; and 
         R 5a , R 5b , R 6 , R 9  and b are as defined in any of  claims 1  and  10  to  26 . 
       
     
     
         39 . The compound as claimed in  claim 37 , of formula I.2.2 
       
         
           
           
               
               
           
         
         wherein 
         R 2a , R 2b , R 3a  and R 5a , independently of each other, are selected from hydrogen and methyl; 
         R 7  is selected from C 1 -C 4 -alkyl and fluorinated C 1 -C 4 -alkyl, preferably from methyl and CF 3 , and is in particular methyl; 
         R 8  is selected from C 1 -C 4 -alkyl and fluorinated C 1 -C 4 -alkyl, and preferably from methyl and CF 3 ; or 
         R 7  and R 8 , together with the carbon atom they are bound to, form a 3-, 4-, 5-, 6- or 7-membered saturated or partially unsaturated ring, where the ring may be substituted with one or more substituents R 11 ; 
         R 9a  is H or F; and 
         R 9  and b are as defined in any of  claims 1  and  10  to  31 . 
       
     
     
         40 . The compound as claimed in  claim 39 , wherein R 2a , R 2b , R 3a  and R 5a  are selected from hydrogen and methyl, with the proviso that at most 2, preferably at most 1, of R 2a , R 2b , R 3a  and R 5a  are methyl. 
     
     
         41 . The compound as claimed in any of  claims 39  or  40 , where R 7  and R 8 , together with the carbon atom they are bound to, form a 4-, 5- or 6-membered saturated or partially unsaturated carbocyclic ring, preferably a 4- or 5-membered saturated carbocyclic ring, in particular a 4-membered saturated carbocyclic ring, where the ring may be substituted with one or more substituents R 11 . 
     
     
         42 . A compound of formula I as claimed in any of the preceding claims, selected from 8,8-dimethyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinolone;
 1,2,3,4-tetrahydrospiro[[1,4]diazepino[6,7,1-ij]quinoline-8,1′-cyclopent[2]en]-6(7H)-one 2,2,2-trifluoroacetate;   8-methyl-8-phenyl-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinolin-6(2H)-one;   8,8-dimethyl-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinolin-6(2H)-one;   1,2,3,4-tetrahydrospiro[[1,4]diazepino[6,7,1-ij]quinoline-8,1′-cyclopentan]-6(7H)-one;   1,2,3,4,6,7-hexahydrospiro[[1,4]diazepino[6,7,1-ij]quinoline-8,1′-cyclopentane];   12a-methyl-4,5,6,7,10,11,12,12a-octahydrocyclopenta[c][1,4]diazepino[6,7,1-ij]quinolin-9(9aH)-one;   8-methyl-8-(trifluoromethyl)-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinolone;   12a-methyl-4,5,6,7,10,11,12,12a-octahydrocyclopenta[c][1,4]diazepino[6,7,1-ij]quinolin-9(9aH)-one;   12a-methyl-4,5,6,7,9,9a,10,11,12,12a-decahydrocyclopenta[c][1,4]diazepino-[6,7,1-ij]quinoline;   8-methyl-8-(trifluoromethyl)-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinolin-6(2H)-one;   12a-methyl-4,5,6,7,9,9a,10,11,12,12a-decahydrocyclopenta[c][1,4]diazepino-[6,7,1-ij]quinoline;   8-methyl-8-phenyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   (R)-5,6,7,9,9a,10,11,12-octahydro-4H-[1,4]diazepino[1,7,6-de]pyrrolo[1,2-a]quinoxaline bis(2,2,2-trifluoroacetate);   (S)-5,6,7,9,9a,10,11,12-octahydro-4H-[1,4]diazepino[1,7,6-de]pyrrolo[1,2-a]quinoxaline bis(2,2,2-trifluoroacetate);   9-chloro-8,8-dimethyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline bis(2,2,2-trifluoroacetate);   10-chloro-8,8-dimethyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline bis(2,2,2-trifluoroacetate);   9-chloro-8,8-dimethyl-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinolin-6(2H)-one 2,2,2-trifluoroacetate;   10-chloro-8,8-dimethyl-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinolin-6(2H)-one 2,2,2-trifluoroacetate;   9-fluoro-8,8-dimethyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   10-fluoro-8,8-dimethyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline bis(2,2,2-trifluoroacetate);   1,2,3,4,6,7-hexahydrospiro[[1,4]diazepino[6,7,1-ij]quinoline-8,1′-cyclohexane]bis(2,2,2-trifluoroacetate);   1′,2′,3′,4′,6′,7′-hexahydrospiro[cyclobutane-1,8′-[1,4]diazepino[6,7,1-ij]quinoline];   9′-fluoro-1′,2′,3′,4′,6′,7′-hexahydrospiro[cyclobutane-1,8′-[1,4]diazepino[6,7,1-ij]quinoline];   7,8,8-trimethyl-1,2,3,4,7,8-hexahydro-6H-[1,4]diazepino[6,7,1-ij]quinoline];   9-fluoro-1-methyl-1,2,3,4,6,7-hexahydrospiro[[1,4]diazepino[6,7,1-ij]quinoline-8,1′-cyclobutane];   3-methyl-1′,2′,3′,4′,6′,7′-hexahydrospiro[cyclobutane-1,8′-[1,4]diazepino[6,7,1-ij]quinoline];   3-benzyl-2′,3′,7′,8′,9′,10′-hexahydro-1H-3′,8′,10a′-triaza-cyclohepta[de]naphthalene;   and the stereoisomers and pharmaceutically acceptable salts thereof.   
     
     
         43 . A pharmaceutical composition comprising a therapeutically effective amount of at least one compound as claimed in any of the preceding claims or an N-oxide, a tautomeric form, a stereoisomer or a pharmaceutically acceptable salt thereof, or comprising at least one compound as defined in any of the preceding claims wherein at least one of the atoms has been replaced by its stable, non-radioactive isotope, preferably wherein at least one hydrogen atom has been replaced by a deuterium atom, in combination with at least one pharmaceutically acceptable carrier and/or auxiliary substance. 
     
     
         44 . The compound as claimed in any of  claims 1  to  42  or an N-oxide, a tautomeric form, a stereoisomer or a pharmaceutically acceptable salt thereof for use as a medicament. 
     
     
         45 . The compound as claimed in any of  claims 1  to  42  or an N-oxide, a tautomeric form, a stereoisomer or a pharmaceutically acceptable salt thereof for the treatment of disorders which respond to the modulation of the 5-HT 2c  receptor. 
     
     
         46 . The use of a compound as claimed in any of  claims 1  to  42  or of an N-oxide, a tautomeric form, a stereoisomer or a pharmaceutically acceptable salt thereof for the manufacture of a medicament for the treatment of disorders which respond to the modulation of the 5-HT 2c  receptor. 
     
     
         47 . A method for treating disorders which respond to the modulation of the 5-HT 2c  receptor, which method comprises administering to a subject in need thereof at least one compound as defined in any of  claims 1  to  42  or an N-oxide, a tautomeric form, a stereoisomer or a pharmaceutically acceptable salt thereof. 
     
     
         48 . The compound as claimed in  claim 45  or the use as claimed in  claim 46  or the method as claimed in  claim 47 , where the disorders are selected from the group consisting of damage of the central nervous system, disorders of the central nervous system, eating disorders, ocular hypertension, cardiovascular disorders, gastrointestinal disorders and diabetes. 
     
     
         49 . The compound or the use or the method as claimed in  claim 48 , where the disorders are selected from the group consisting of bipolar disorder, depression, atypical depression, mood episodes, adjustment disorders, anxiety, panic disorders, post-traumatic syndrome, psychoses, schizophrenia, cognitive deficits of schizophrenia, memory loss, dementia of aging, Alzheimer's disease, behavioral disorders associated with dementia, social phobia, mental disorders in childhood, attention deficit hyperactivity disorder, organic mental disorders, autism, mutism, disruptive behavior disorder, impulse control disorder, borderline personality disorder, obsessive compulsive disorder, migraine and other conditions associated with cephalic pain or other pain, raised intracranial pressure, seizure disorders, epilepsy, substance use disorders, alcohol abuse, cocaine abuse, tobacco abuse, smoking cessation, sexual dysfunction/erectile dysfunction in males, sexual dysfunction in females, premenstrual syndrome, late luteal phase syndrome, chronic fatigue syndrome, sleep disorders, sleep apnoea, chronic fatigue syndrome, psoriasis, Parkinson's disease, spinal cord injury, trauma, stroke, pain, bladder dysfunction/urinary incontinence, encephalitis, meningitis, eating disorders, obesity, bulimia, weight loss, anorexia nervosa, ocular hypertension, cardiovascular disorders, gastrointestinal disorders, diabetes insipidus, diabetes mellitus, type I diabetes, type II diabetes, type III diabetes, diabetes secondary to pancreatic diseases, diabetes related to steroid use, diabetes complications, hyperglycemia and insulin resistance. 
     
     
         50 . The compound or the use or the method as claimed in  claim 49 , where the disorders are selected from schizophrenia, depression, bipolar disorders, obesity and substance use disorders.