Hexahydrodiazepinoquinolines carrying a cyclic radical

Abstract

The present invention relates to tricyclic hexahydrodiazepinoquinolines carrying a cyclic substituent, to a method for producing them, 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, to a method for preventing or treating conditions and disorders which respond to the modulation of 5-HT 2C receptor, and processes for preparing such compounds and compositions.

We claim: 
     
         1 . A compound of the formula I 
       
         
           
           
               
               
           
         
         wherein 
         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 9 , 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 10 ; 
         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-C 1 -C 4 -alkyl, fluorinated C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, —CH 2 NR 11a R 11b , —C(O)R 9 , phenyl, phenyl-C 1 -C 2 -alkyl, 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 10 ; or
 two radicals R 2  bound to the same carbon atom, 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 10 ; 
 
         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-C 1 -C 4 -alkyl, fluorinated C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, —CH 2 NR 11a R 11b , —C(═O)R 9 , phenyl, phenyl-C 1 -C 2 -alkyl, 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 10 ; 
         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-C 1 -C 4 -alkyl, fluorinated C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, —CH 2 NR 11a R 11b , —C(═O)R 9 , phenyl, phenyl-C 1 -C 2 -alkyl, 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 10 ; or
 R 4a  and R 4b  form together a group ═O or ═S; or 
 R 4a  and R 4b , 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 10 ; 
 
         R 5a  and R 5b , independently of each other, are selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxyl, 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, fluorinated 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 11a R 11b , —CH 2 NR 11a R 11b , —NR 11a C(O)R 9 , —C(═O)R 9 , SO 2 NR 11a R 11b , 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 10 ; where R 5a  and R 5b  are not simultaneously hydroxyl; 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 10 ; 
         R 6  is a cyclic radical selected from the group consisting of C 3 -C 6 -cycloalkyl which may carry one or more radicals R 8 ; 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 groups C═O and/or C═S, as ring members, where the heterocyclic ring may be substituted with one or more substituents R 10 ; 
         each R 7  is independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, 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, fluorinated 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 11a R 11b , —CH 2 NR 11a R 11b , —NR 11a C(O)R 9 , —C(═O)R 9 , SO 2 NR 11a R 11b , 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 10 ; or
 two radicals R 7  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 10 ; 
 
         each R 8  is independently selected from the group consisting of halogen, cyano, hydroxyl, 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, fluorinated C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, —NR 11a R 11b , —CH 2 NR 11a R 11b , 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 10 ;
 or two radicals R 8  bound to the same carbon atom may form together a group ═O or ═S; 
 
         each R 9  is independently selected from the group consisting of hydrogen, cyano, hydroxyl, 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 11a R 11b , —CH 2 NR 11a R 11b , 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 10 ; 
         each R 10  is independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, 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, fluorinated 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 11a R 11b , —CH 2 NR 11a R 11b , 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 11a R 11b , C 1 -C 6 -alkylcarbonyloxy and fluorinated C 1 -C 6 -alkylcarbonyloxy;
 or two radicals R 10 , together with the atom(s) they are bound to, form a saturated, partially unsaturated or maximally unsaturated 3-, 4-, 5-, 6- or 7-membered carbocyclic or heterocyclic ring, where the heterocyclic ring contains 1, 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO, SO 2 , C═O and C═S as ring members; 
 
         R 11a  and R 11b  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 11a  and R 11b  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; and 
         b is 0, 1, 2 or 3; 
         or an N-oxide, a tautomeric form, a stereoisomer or a pharmaceutically acceptable salt thereof. 
       
     
     
         2 . The compound as claimed in  claim 1 , where R 1  is selected from hydrogen and C 1 -C 6 -alkyl. 
     
     
         3 . The compound as claimed in  claim 2 , where R 1  is hydrogen. 
     
     
         4 . The compound as claimed in any of the preceding claims, where R 2  is selected from C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl and fluorinated C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl. 
     
     
         5 . The compound as claimed in  claim 4 , where R 2  is selected from C 1 -C 6 -alkyl and fluorinated C 1 -C 6 -alkyl. 
     
     
         6 . The compound as claimed in  claim 5 , where R 2  is selected from methyl and CF 3 . 
     
     
         7 . 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 and fluorinated C 1 -C 6 -alkyl. 
     
     
         8 . The compound as claimed in  claim 7 , where R 3a  is selected from hydrogen, cyano, nitro, C 1 -C 6 -alkyl and fluorinated C 1 -C 6 -alkyl; and R 3b  is hydrogen. 
     
     
         9 . The compound as claimed in  claim 8 , where R 3a  is selected from hydrogen and methyl; and R 3b  is hydrogen. 
     
     
         10 . The compound as claimed in  claim 9 , where R 3a  and R 3b  are hydrogen. 
     
     
         11 . 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, fluorinated C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl and fluorinated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or form together a group ═O, or form together a group —(CH 2 ) m —, where m is 2, 3 or 4. 
     
     
         12 . The compound as claimed in  claim 11 , where R 4a  and R 4b  are hydrogen. 
     
     
         13 . The compound as claimed in any of the preceding claims, where R 5a  is selected from hydrogen, halogen, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl and R 5b  is hydrogen. 
     
     
         14 . The compound as claimed in  claim 13 , where R 5a  is hydrogen or methyl and R 5b  is hydrogen. 
     
     
         15 . The compound as claimed in any of the preceding claims, where R 6  is C 3 -C 6 -cycloalkyl which may carry one or more radicals R 8 ; where R 8  is as defined in  claim 1 . 
     
     
         16 . The compound as claimed in  claim 15 , where each R 8  is independently selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl, fluorinated C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl and fluorinated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl. 
     
     
         17 . The compound as claimed in any of  claim 15  or  16 , where R 6  is selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 2,2-difluorocyclopropyl and 3,3-difluorocyclobutyl. 
     
     
         18 . The compound as claimed in  claim 17 , where R 6  is selected from cyclopropyl and cyclobutyl. 
     
     
         19 . The compound as claimed in  claim 18 , where R 6  is cyclopropyl. 
     
     
         20 . The compound as claimed in  claim 17 , where R 6  is 2,2-difluorocyclopropyl. 
     
     
         21 . The compound as claimed in any of  claims 1  to  14 , where R 6  is a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO 2 , and optionally also 1 or 2 groups C═O and/or C═S, as ring members, where the heterocyclic ring may be substituted with one or more substituents R 10 ;
 where R 10  is as defined in  claim 1 . 
 
     
     
         22 . The compound as claimed in  claim 21 , where R 6  is 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 10 ;
 where R 10  is as defined in  claim 1 .   
     
     
         23 . The compound as claimed in  claim 22 , where R 6  is a 4-membered saturated heterocyclic ring containing 1 heteroatom or heteroatom group selected from N, O, S, NO, SO and SO 2  as ring member, where the heterocyclic ring may be substituted with one or more substituents R 10 ;
 where R 10  is as defined in  claim 1 .   
     
     
         24 . The compound as claimed in  claim 23 , where R 6  is a 4-membered saturated heterocyclic ring containing an oxygen atom as ring member, where the heterocyclic ring may be substituted with one or more substituents R 10 ; where R 10  is as defined in  claim 1 . 
     
     
         25 . The compound as claimed in  claim 24 , where R 6  is oxetan-3-yl which may be substituted with one or more substituents R 10 ; where R 10  is as defined in  claim 1 . 
     
     
         26 . The compound as claimed in  claim 22 , where R 6  is a 5- or 6-membered saturated heterocyclic ring containing 1 heteroatom or heteroatom group selected from N, O, S, NO, SO and SO 2  as ring member, where the heterocyclic ring may be substituted with one or more substituents R 10 ;
 where R 10  is as defined in  claim 1 .   
     
     
         27 . The compound as claimed in  claim 26 , where R 6  is a 5- or 6-membered saturated heterocyclic ring containing an oxygen atom as ring member, where the heterocyclic ring may be substituted with one or more substituents R 10 ; where R 10  is as defined in  claim 1 . 
     
     
         28 . The compound as claimed in  claim 27 , where R 6  is tetrahydrofuran-3-yl or tetrahydropyran-4-yl which may be substituted with one or more substituents R 10 ;
 where R 10  is as defined in  claim 1 .   
     
     
         29 . The compound as claimed in any of  claims 21  to  28 , where R 10  is selected from the group consisting of halogen, C 1 -C 6 -alkyl and fluorinated C 1 -C 6 -alkyl. 
     
     
         30 . The compound as claimed in  claim 29 , where R 10  is methyl. 
     
     
         31 . The compound as claimed in any of the preceding claims, where each R 7  is independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, 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 and fluorinated C 1 -C 6 -alkoxy. 
     
     
         32 . The compound as claimed in  claim 31 , where each R 7  is independently selected from halogen, C 1 -C 4 -alkyl, fluorinated C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy and fluorinated C 1 -C 4 -alkoxy. 
     
     
         33 . The compound as claimed in  claim 32 , where R 7  is fluorine. 
     
     
         34 . The compound as claimed in any of  claims 1  to  31 , where each R 7  is independently selected from the group consisting of cyano and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl. 
     
     
         35 . The compound as claimed in any of the preceding claims, where a is 0 or 1. 
     
     
         36 . The compound as claimed in  claim 35 , where in case that a is 1, R 2  is bound in β-position to the nitrogen ring atom carrying R 1 . 
     
     
         37 . The compound as claimed in any of the preceding claims, where b is 0 or 1. 
     
     
         38 . The compound as claimed in any of the preceding claims, of formula I.1 
       
         
           
           
               
               
           
         
         wherein R 2 , R 6 , R 7  and b are as defined in any of  claims 1 ,  4  to  6 ,  15  to  34  and  37  and a is 0 or 1. 
       
     
     
         39 . The compound as claimed in  claim 38 , of formula I.1.1 
       
         
           
           
               
               
           
         
         wherein 
         R 7a  is H, Cl, F or methyl; 
         a is 0 or 1; and 
         R 2 , R 6 , R 7  and b are as defined in any of  claims 1 ,  4  to  6 ,  15  to  34  and  37 . 
       
     
     
         40 . A compound selected from the group consisting of
 8-Cyclopropyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   (R)-8-Cyclopropyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   (S)-8-Cyclopropyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   8-Cyclobutyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   (R)-8-Cyclobutyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   (S)-8-Cyclobutyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   8-(3-Methyloxetan-3-yl)-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   8-(2,2-Difluorocyclopropyl)-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   8-(Oxetan-3-yl)-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   8-(Tetrahydro-2H-pyran-4-yl)-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   8-(Tetrahydrofuran-3-yl)-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   8-Cyclopropyl-10-(2-methoxyethyl)-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;   8-Cyclopropyl-10-(methoxymethyl)-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline; and   8-Cyclopropyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-10-carbonitrile;   and stereoisomers and pharmaceutically acceptable salts thereof.   
     
     
         41 . A method for producing a compound of formula I according to  claim 1  wherein R 1 , R 4b  and R 5b  are hydrogen and R 2 , if present, is bound in β-position to the nitrogen ring atom carrying R 1  (compound I′), comprising following steps:
 reacting a quinoline compound 1 in which X is a leaving group with a boron compound of R 6  to the quinoline compound 2 in the presence of a Pd catalyst; 
 reacting the quinoline compound 2 with benzyl bromide to the N-protected quinolinium compound 3; 
 reducing the quinolinium compound 3 to the N-protected 1,2,3,4-tetrahydroquinoline compound 4; 
 deprotecting the N-protected 1,2,3,4-tetrahydroquinoline compound 4 to the 1,2,3,4-tetrahydroquinoline compound 5; 
 reacting the 1,2,3,4-tetrahydroquinoline compound 5 with the 2-halogenoacetamide 6, wherein Y is Cl, Br or I, to the 1-acetamide-substituted 1,2,3,4-tetrahydroquinoline compound 7; 
 reducing the carbonyl group of the 1-acetamide-substituted 1,2,3,4-tetrahydroquinoline compound 7 to the ethylamine-substituted tetrahydroquinoline compound 8; 
 reacting 8 with the aldehyde or ketone 9, wherein R ia  and R ab  are as defined in  claim 1 , but for nitro or cyano, in the presence of a strong acid to I′; or 
 reacting 2 with the 2-halogenoacetamide 6 to 10, which is then reduced to 7, which is further reacted as described above: 
 
       
         
           
           
               
               
           
         
       
     
     
         42 . A method for producing a compound of formula I according to  claim 1  wherein R 1 , R 4a , R 4b  and R 5b  are hydrogen, and R 2 , if present, is bound in β-position to the nitrogen ring atom carrying R 1  (compound I″), comprising following steps:
 reacting the boronic acid 11 and the α,β-unsaturated ester 12 in the presence of a Rhodium catalyst to the dihydroquinolone 13; 
 reducing the dihydroquinolone 13 to the 1,2,3,4-tetrahydroquinoline 14; 
 reacting the 1,2,3,4-tetrahydroquinoline 14 with the 2-halogenoacetamide 6, wherein Y is Cl, Br or I, to the 1-acetamide-substituted 1,2,3,4-tetrahydroquinoline compound 15; 
 reducing the carbonyl group of the 1-acetamide-substituted 1,2,3,4-tetrahydroquinoline compound 15 to the ethylamine-substituted tetrahydroquinoline compound 16; and 
 reacting 16 with the aldehyde or ketone 9, wherein R 3a  and R 3b  are as defined in  claim 1 , but for nitro or cyano, in the presence of a strong acid to I″: 
 
       
         
           
           
               
               
           
         
       
     
     
         43 . A pharmaceutical composition comprising a therapeutically effective amount of at least one compound as claimed in any of  claims 1  to  40  or an N-oxide, a tautomeric form, a stereoisomer or a pharmaceutically acceptable salt thereof, in combination with at least one pharmaceutically acceptable carrier and/or auxiliary substance. 
     
     
         44 . The compound as claimed in any of  claims 1  to  40  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  40  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  40  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  40  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, neuropsychiatric symptoms in 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, psychosis in Parkinson's disease, neuropsychiatric symptoms in Parkinson's disease, Lewy Body dementia, neuropsychiatric symptoms in Lewy Body dementia, 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, substance use disorders, neuropsychiatric symptoms in Alzheimer's disease and neuropsychiatric symptoms in Parkinson's disease.