Spirocyclic cyclohexane compounds

1. A spirocyclic cyclohexane compound corresponding to formula I

wherein

R 1 and R 2 independently of one another represent H, C 1-5 -alkyl, branched or unbranched, saturated or unsaturated, unsubstituted or mono- or polysubstituted, or CHO; or

R 1 and R 2 together represent CH 2 CH 2 OCH 2 CH 2 , CH 2 CH 2 NR 11 CH 2 CH 2 or (CH 2 ) 3-6 ,

wherein

R 11 denotes H; C 1-5 -alkyl, in each case saturated or unsaturated, branched or unbranched, mono- or polysubstituted or unsubstituted; C 3-8 -cycloalkyl, in each case saturated or unsaturated, mono- or polysubstituted or unsubstituted; aryl-, or heteroaryl, in each case mono- or polysubstituted or unsubstituted; or aryl, C 3-8 -cycloalkyl or heteroaryl which are bonded via C 1-3 -alkyl and are in each case mono- or polysubstituted or unsubstituted;

R 3 represents C 1-5 -alkyl, in each case saturated or unsaturated, branched or unbranched, mono- or polysubstituted or unsubstituted; C 3-8 -cycloalkyl, in each case saturated or unsaturated, mono- or polysubstituted or unsubstituted; aryl, in each case unsubstituted or mono- or polysubstituted; aryl or C 3-8 -cycloalkyl which are bonded via a C 1-3 -alkylene group and are in each case unsubstituted or mono- or polysubstituted;

W represents NR 4 , O or S;

wherein

R 4 denotes H; C 1-5 -alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted; aryl, or heteroaryl, in each case substituted or unsubstituted; aryl, heteroaryl or cycloalkyl which are bonded via a C 1-3 -alkyl group and are in each case mono- or polysubstituted or unsubstituted; COR 12 ; SO 2 R 12 ,

wherein

R 12 denotes H; C 1-5 -alkyl, in each case saturated or unsaturated, branched or unbranched, mono- or polysubstituted or unsubstituted; C 3-8 -cycloalkyl, in each case saturated or unsaturated, mono- or polysubstituted or unsubstituted; aryl-, or heteroaryl, in each case mono- or polysubstituted or unsubstituted; or aryl, C 3-8 -cycloalkyl or heteroaryl which are bonded via C 1-3 -alkyl and are in each case mono- or polysubstituted or unsubstituted; OR 13 ; NR 14 R 15 ;

R 5 represents ═O; H; COOR 13 , CONR 13 , OR 13 ; C 1-5 -alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted; C 3-8 -cycloalkyl, saturated or unsaturated, unsubstituted or mono- or polysubstituted; aryl-, or heteroaryl, unsubstituted or mono- or polysubstituted; or aryl, C 3-8 -cycloalkyl or heteroaryl which are bonded via C 1-3 -alkyl and are unsubstituted or mono- or polysubstituted;

R 6 represents H; F, Cl, NO 2 , CF 3 , OR 13 , SR 13 , SO 2 R 13 , SO 2 OR 13 , CN, COOR 13 , NR 14 R 15 ; C 1-5 -alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted; C 3-8 -cycloalkyl, saturated or unsaturated, unsubstituted or mono- or polysubstituted; aryl-, or heteroaryl, unsubstituted or mono- or polysubstituted; or aryl, C 3-8 -cycloalkyl or heteroaryl which are bonded via C 1-3 -alkyl and are unsubstituted or mono- or polysubstituted; or

R 5 and R 6 together denote (CH 2 ) n , where n=2, 3, 4, 5 or 6, wherein individual hydrogen atoms can also be replaced by F, Cl, Br, I, NO 2 , CF 3 , OR 13 , CN or C 1-5 -alkyl;

R 7 , R 8 , R 9 and R 10 independently of one another represent H, F, Cl, Br, I, NO 2 , CF 3 , OR 13 , SR 13 , SO 2 R 13 , SO 2 OR 13 , SO 2 NH 2 CN, COOR 13 , NR 14 R 15 ; C 1-5 -alkyl, C 3-8 -cycloalkyl, unsubstituted or mono- or polysubstituted; aryl-, or heteroaryl, unsubstituted or mono- or polysubstituted; or aryl, C 3-8 -cycloalkyl or heteroaryl which are bonded via C 1-3 -alkyl and are unsubstituted or mono- or polysubstituted;

wherein

R 13 denotes H; C 1-5 -alkyl in each case saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted; C 3-8 -cycloalkyl, in each case saturated or unsaturated, unsubstituted or mono- or polysubstituted; aryl-, or heteroaryl, unsubstituted or mono- or polysubstituted; or aryl, C 3-8 -cycloalkyl or heteroaryl which are bonded via C 1-3 -alkyl and are unsubstituted or mono- or polysubstituted;

R 14 and R 15 independently denote H; C 1-5 -alkyl, in each case saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted; or C 3-8 -cycloalkyl, in each case saturated or unsaturated, unsubstituted or mono- or polysubstituted; aryl-, or heteroaryl, unsubstituted or mono- or polysubstituted; or aryl, C 3-8 -cycloalkyl or heteroaryl which are bonded via C 1-3 -alkyl and are unsubstituted or mono- or polysubstituted; or

R 14 and R 15 together form CH 2 CH 2 OCH 2 CH 2 , CH 2 CH 2 NR 16 CH 2 CH 2 or (CH 2 ) 3-6 ,

wherein

R 16 denotes H; C 1-5 -alkyl saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted;

X represents O, S, SO or SO 2 ;

wherein, with reference to alkyl, mono- or polysubstituted means substitution of one or more hydrogen radicals by F, Cl, Br, I, —CN, NH 2 , NH-alkyl, NH-aryl, NH-heteroaryl, NH-cycloalkyl, NH-alkyl-aryl, NH-alkyl-heteroaryl, NH-alkyl-OH, N(alkyl) 2 , N(alkyl-aryl) 2 , N(alkyl-heteroaryl) 2 , N(cycloalkyl) 2 , N(alkyl-OH) 2 , NO 2 , SH, S-alkyl, S-aryl, S-heteroaryl, S-alkyl-aryl, S-alkyl-heteroaryl, S-cycloalkyl, S-alkyl-OH, S-alkyl-SH, OH, O-alkyl, O-aryl, O-heteroaryl, O-alkyl-aryl, O-alkyl-heteroaryl, O-cycloalkyl, O-alkyl-OH, CHO, C(═O)C 1-6 -alkyl, C(═S)C 1-6 -alkyl, C(═O)aryl, C(═S)aryl, C(═O)C 1-6 -alkyl-aryl, C(═S)C 1-6 -alkyl-aryl, C(═O)-heteroaryl, C(═S)-heteroaryl, C(═O)-cycloalkyl, C(═S)-cycloalkyl, CO 2 H, CO 2 -alkyl, CO 2 -alkyl-aryl, C(═O)NH 2 , C(═O)NH-alkyl, C(═O)NHaryl, C(═O)NH-cycloalkyl, C(═O)N(alkyl) 2 , C(═O)N(alkyl-aryl) 2 , C(═O)N(alkyl-heteroaryl) 2 , C(═O)N(cycloalkyl) 2 , SO-alkyl, SO 2 -alkyl, SO 2 NH 2 , SO 3 H, PO(O—C 1-6 -alkyl) 2 , Si(C 1-6 -alkyl) 3 , Si(C 3-8 -cycloalkyl) 3 , Si(CH 2 —C 3-8 -cycloalkyl) 3 , Si(phenyl) 3 , cycloalkyl, aryl or heteroaryl on one or different atoms; and

wherein, with reference to aryl, heteroaryl and cycloalkyl, mono- or polysubstituted means substitution of one or more hydrogen atoms of the ring system by F, Cl, Br, I, CN, NH 2 , NH-alkyl, NH-aryl, NH-heteroaryl, NH— alkyl-aryl, NH— alkyl-heteroaryl, NH— cycloalkyl, NH-alkyl-OH, N(alkyl) 2 , N(alkyl-aryl) 2 , N(alkyl-heteroaryl) 2 , N(cycloalkyl) 2 , N(alkyl-OH) 2 , NO 2 , SH, S-alkyl, S-cycloalkyl, S-aryl, S-heteroaryl, S-alkyl-aryl, S-alkyl-heteroaryl, S-cycloalkyl, S-alkyl-OH, S-alkyl-SH, OH, O-alkyl, O-cycloalkyl, O-aryl, O-heteroaryl, O-alkyl-aryl, O-alkyl-heteroaryl, O-cycloalkyl, O-alkyl-OH, CHO, C(═O)C 1-6 -alkyl, C(═S)C 1-6 -alkyl, C(═O)aryl, C(═S)aryl, C(═O)—C 1-6 -alkyl-aryl, C(═S)C 1-6 -alkyl-aryl, C(═O)-heteroaryl, C(═S)-heteroaryl, C(═O)-cycloalkyl, C(═S)-cycloalkyl, CO 2 H, CO 2 -alkyl, CO 2 -alkyl-aryl, C(═O)NH 2 , C(═O)NH-alkyl, C(═O)NHaryl, C(═O)NH-cycloalkyl, C(═O)N(alkyl) 2 , C(═O)N(alkyl=aryl) 2 , C(═O)N(alkyl-heteroaryl) 2 , C(═O)N(cycloalkyl) 2 , S(O)-alkyl, S(O)-aryl, SO 2 -alkyl, SO 2 -aryl, SO 2 NH 2 , SO 3 H, CF 3 , ═O, ═S; alkyl, cycloalkyl, aryl or heteroaryl; on one or different atoms

or a physiologically acceptable salt thereof.

2. A spirocyclic cyclohexane compound according to claim 1 , wherein said compound is the form of a racemate.

3. A spirocyclic cyclohexane compound according to claim 1 , wherein said compound is in the form of a pure enantiomer or diastereomer.

4. A spirocyclic cyclohexane compound according to claim 1 , wherein said compound is in the form of a mixture of enantiomers or diastereomers.

5. A spirocyclic cyclohexane compound according to claim 1 , wherein

R 3 denotes a phenyl, benzyl or phenethyl group, which may be unsubstituted, monosubstituted polysubstituted on the ring.

6. A spirocyclic cyclohexane compound according to claim 1 , wherein

R 5 denotes H; C 1-5 -alkyl which may be branched or unbranched, unsubstituted, monosubstituted or polysubstituted; or COOR 13 ; and

R 6 denotes H or C 1-5 -alkyl.

7. A spirocyclic cyclohexane compound according to claim 1 , wherein

R 7 , R 8 , R 9 and R 10 independently of one another represent H; C 1-5 -alkyl, branched or unbranched, unsubstituted or mono- or polysubstituted; F, Cl, Br, I, CF 3 , OH, OCH 3 , NH 2 , COOH, COOCH 3 , NHCH 3 , N(CH 3 ) 2 , NO 2 , SO 3 H, SO 2 NH 2 , pyridyl or phenyl.

8. A spirocyclic cyclohexane compound according to claim 1 , wherein

W denotes NR 4 , O or S;

X denotes O, S, SO or SO 2 ;

R 1 and R 2 independently of one another denote H; C 1-4 -alkyl, branched or unbranched, mono- or polysubstituted or unsubstituted; or CHO;

R 3 denotes (CH 2 ) n -aryl, in each case unsubstituted or mono- or polysubstituted on the aryl, where n=0-2;

R 4 denotes H; C 1-3 -alkyl, mono- or polysubstituted or unsubstituted; CO(CH 2 ) m H, where m=0 to 2;

R 5 and R 6 in each case represent H; and

R 7 , R 8 , R 9 and R 10 independently of one another represent H; C 1-5 -alkyl, OC 1-3 -alkyl, in each case branched or unbranched, saturated or unsaturated, unsubstituted or mono- or polysubstituted; F, Cl, Br, I, CF 3 , OH, SH, SCH 3 , OCH 3 , NH 2 , COOH, COOCH 3 , NHCH 3 , N(CH 3 ) 2 , NO 2 , SO 3 H, SO 2 NH 2 , pyridyl or phenyl.

9. A spirocyclic cyclohexane compound according to claim 1 , wherein

R 1 and R 2 independently denote H or CH 3 ,

with the proviso that R 1 and R 2 are not simultaneously both H.

10. A spirocyclic cyclohexane compound according to claim 9 , wherein

R 3 denotes phenyl, benzyl or phenethyl, in each case unsubstituted, monosubstituted or polysubstituted on the ring.

11. A spirocyclic cyclohexane compound according to claim 10 , wherein R 3 denotes phenyl, benzyl, phenethyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 4-chlorophenyl, 3-chlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 3-trifluoromethylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4-dichlorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4-difluorophenyl, 2-fluoro-3-chlorophenyl, 2-chloro-3-fluorophenyl, 2-chloro-4-fluorophenyl, 2-fluoro-4-chlorophenyl, 4-fluoro-3-chlorophenyl, 4-fluoro-3-methylphenyl, 4-tert-butylphenyl, 4-fluoro-3-chlorophenyl, 4-bromo-3-fluorophenyl, 3,5-bis(trifluoromethyl)phenyl, 4-chloro-2-trifluoromethylphenyl, 2-methoxy-5-methylphenyl, 5-chloro-2-methoxyphenyl, 4-phenoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 5-fluoro-2-methoxyphenyl, 4-chloro-3-trifluoromethyl or 4-bromo-2-methylphenyl.

12. A spirocyclic cyclohexane compound according to claim 11 , wherein

R 3 denotes phenyl, benzyl, phenethyl, 4-fluorophenyl, or 3-fluorophenyl.

13. A spirocyclic cyclohexane compound according to claim 1 , wherein:

W represents NR 4 ;

X denotes O;

R 1 and R 2 independently of one another denote H; C 1-4 -alkyl, branched or unbranched, mono- or polysubstituted or unsubstituted; or CHO

R 3 denotes (CH 2 ) n -aryl, in each case unsubstituted, monosubstituted or polysubstituted on the aryl group, where n=0-2;

R 4 denotes H; C 1-3 -alkyl, mono- or polysubstituted or unsubstituted; or CO(CH 2 ) m H, where m=0 to 2;

R 5 and R 6 in each case represent H; and

R 7 , R 8 , R 9 and R 10 independently of one another denote H; C 1-5 -alkyl, OC 1-3 -alkyl, in each case branched or unbranched, saturated or unsaturated, unsubstituted, monosubstituted or polysubstituted; F, Cl, Br, I, CF 3 , OH, SH, SCH 3 , OCH 3 , NH 2 , COOH, COOCH 3 , NHCH 3 , N(CH 3 ) 2 , NO 2 , SO 3 H, SO 2 NH 2 , pyridyl or phenyl.

14. A spirocyclic cyclohexane compound according to claim 1 , wherein:

R 5 represents H, CH 3 , COOH, COOCH 3 or CH 2 OH;

R 6 represents H; and

R 7 , R 8 , R 9 and R 10 each denote H, or

one of R 7 , R 8 , R 9 and R 10 represents H; C 1-5 -alkyl, branched or unbranched, unsubstituted, monosubstituted or polysubstituted; F, Cl, Br, I, OH, OCH 3 , COOH, COOCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 , NO 2 , SO 3 H, SO 2 NH 2 , pyridyl or phenyl, while the others of R 7 , R 8 , R 9 and R 10 each denote H, or

two of R 7 , R 8 , R 9 and R 10 independently of one another denote H; C 1-5 -alkyl, branched or unbranched, unsubstituted, monosubstituted or polysubstituted; F, Cl, Br, I, OH, OCH 3 , COOH, COOCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 , NO 2 , SO 3 H, SO 2 NH 2 , pyridyl or phenyl, while the others of R 7 , R 8 , R 9 and R 10 each denote H.

15. A spirocyclic cyclohexane compound according to claim 9 , wherein

R 1 and R 2 each denote CH 3 , and

R 3 denotes phenyl.

16. A spirocyclic cyclohexane compound according to claim 1 , wherein:

W denotes NR 4 , and

R 4 denotes H, CH 3 , C 2 H 5 , acetyl, phenyl, benzyl or COR 12 ; and

X denotes O.

17. A spirocyclic cyclohexane compound according to claim 1 , selected from the group consisting of:

1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole hydrochloride,

1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole hemicitrate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2-thia-9-azafluorene hemicitrate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2-thia-9-azafluorene citrate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3,4-dihydro-1H-2-oxa-9-thiafluorene L-tartrate,

1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-3,4-dihydro-1H-2-oxa-9-thiafluorene triflate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3,4-dihydro-1H-2,9-dioxafluorene hemicitrate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-6-methoxy-1,3,4,9-tetrahydropyrano[3,4-b]indole hydrochloride,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole citrate,

6-bromo-1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole hemicitrate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-6-nitro-1,3,4,9-tetrahydropyrano[3,4-b]indole citrate,

6-chloro-1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole citrate,

3,9-dimethyl-1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole citrate,

1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole hemicitrate,

1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole hemicitrate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole hemicitrate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-6-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole hemicitrate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-9-phenyl-1,3,4,9-tetrahydropyrano[3,4-b]indole citrate,

1,1-(3-methylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-pyrano-[3,4-b]indole hemicitrate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-3-methyl-1,3,4,9-tetrahydro-pyrano-[3,4-b]indole hemicitrate,

3,6-dimethyl-1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-pyrano-[3,4-b]indole hemicitrate,

3,6-dimethyl-1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-pyrano-[3,4-b]indole citrate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-9-phenyl-1,3,4,9-tetrahydropyrano[3,4-b]indole citrate,

1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-2-thia-9-azafluorene methanesulfonate,

1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-2-thia-9-azafluorene methanesulfonate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3,4-dihydro-1H-9-oxa-2-thiafluorene citrate,

6,6-(3-dimethylamino-3-phenylpentamethylene)-1,2,3,4,4a,6,7,11c-octahydro-5-oxa-7-azabenzo[c]fluorene citrate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-6-bromo-1,3,4,9-tetrahydropyrano[3,4-b]indole hemicitrate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-6-ol citrate,

1,1-(3-methylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole hemicitrate,

1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-3,4-dihydro-1H-2,9-dithiafluorene methanesulfonate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3,4-dihydro-1H-2,9-dithiafluorene citrate,

1,1-(3-dimethylamino-3-phenylpentamethylene)-2-oxo-1,3,4,9-tetrahydro-2-thia-9-aza-fluorene citrate, and

salts thereof with physiologically acceptable acids or cations.