1. An N,N\u2032-disubstituted piperazine compound corresponding to formula I,
wherein
R1 and R2, identical or different, in each case denote a linear or branched, saturated or unsaturated aliphatic residue, or together form a (CH2)n chain, wherein n denotes an integer;
R3 and R5, identical or different, in each case denote a linear or branched, saturated or unsaturated aliphatic residue, a saturated or unsaturated cycloaliphatic residue, an aryl residue or a heteroaryl residue; and
R4 denotes hydrogen or an optionally identically or differently mono- or polysubstituted aryl or heteroaryl residue,
or a salt thereof with a physiologically acceptable acid.
2. The compound of claim 1, wherein the respective ring system of R3 or R5 is mono- or polysubstituted or attached via a linear or branched, saturated or unsaturated aliphatic bridge or the aryl or heteroaryl residue is part of a polycyclic system.
3. The compound of claim 1, wherein the aryl or heteroaryl residue of R4 is part of a polycyclic system.
4. The compound of claim 1, wherein said compound is present in the form of a free base.
5. The compound of claim 1, wherein said compound is present in the form of a pure enantiomer or pure diastereoisomer.
6. The compound of claim 1, wherein said compound is present in the form of a mixture of stereoisomers.
7. The compound of claim 1, wherein said compound is present in the form of a racemic mixture.
8. The compound of claim 1, wherein said compound is present in the form of a solvate.
9. The compound of claim 1, wherein
R1 and R2, identical or different, in each case denote a linear or branched, saturated or unsaturated aliphatic C1-6 residue, or together form a (CH2)n chain, wherein n denotes an integer from 2-9;
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-6 residue, a saturated or unsaturated cycloaliphatic C3-7 residue, a phenyl residue or a five- or six-membered heteroaryl residue;
R4 denotes hydrogen or a phenyl residue; and
R5 denotes a linear or branched, saturated or unsaturated aliphatic C1-6 residue or a phenyl residue.
10. A compound according to claim 9, wherein the respective ring system of R3 is mono- or polysubstituted or attached via a linear or branched, saturated or unsaturated aliphatic C1-5 bridge.
11. A compound according to claim 9, wherein the phenyl residue of R5 is substituted.
12. A compound according to claim 1, wherein
R1 and R2, identical or different, in each case denote a linear or branched, saturated or unsaturated aliphatic C1-3 residue, or together form a (CH2)n chain, wherein n denotes an integer from 2-9;
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-3 residue, a saturated or unsaturated cycloaliphatic C5-6 residue, a phenyl residue or a five- or six-membered heteroaryl residue;
R4 denotes hydrogen or a phenyl residue; and
R5 denotes a linear or branched, saturated or unsaturated aliphatic C1-3 residue or a phenyl residue optionally substituted with halogen or an alkoxy group.
13. A compound according to claim 12, wherein the respective ring system of R3 is optionally mono- or polysubstituted with halogen, an alkyl group, an alkoxy group or a trihalogenated alkyl group or is attached via a linear or branched, saturated or unsaturated aliphatic C1-3 bridge.
14. A compound according to claim 12, wherein the phenyl residue of R5 is substituted.
15. A compound according to claim 1, wherein
R1 and R2 in each case denote a methyl group, or together form a (CH2)n chain, wherein n denotes 3, 4, 5 or 9;
R3 denotes a vinyl residue, a cyclopentyl residue, a cyclohexyl residue, a thiophenyl residue or a phenyl residue;
R4 denotes hydrogen or a phenyl residue; and
R5 denotes a methyl group or a phenyl residue.
16. A compound according to claim 15, wherein the cyclohexyl residue of R3 is attached via a methylene bridge or the phenyl residue is mono- or polysubstituted with fluorine, chlorine, a methyl group, an isopropyl group, a methoxy group or a trifluoroethyl group or is attached via a linear saturated aliphatic C1-3 bridge or an ethynyl bridge.
17. A compound according to claim 5, wherein the phenyl residue of R5 is substituted with chlorine or a methoxy group.
18. A compound according to claim 1, wherein said compound corresponds to formula II
19. A compound according to claim 1, said compound corresponding to formula III,
wherein
X denotes hydrogen, halogen or an alkoxy group.
20. A compound according to claim 19, wherein X denotes hydrogen, chlorine or a methoxy group.
21. A compound according to claim 1, said compound corresponding to formula IV,
wherein n denotes an integer from 2-9.
22. A compound according to claim 1, said compound corresponding to formula V,
wherein n denotes an integer from 2-9 and
X denotes hydrogen, halogen or an alkoxy group.
23. A compound according to claim 22, wherein X denotes hydrogen, chlorine or a methoxy group.
24. A compound according to claim 1, said compound corresponding to formula VI,
wherein n denotes an integer from 2-9.
25. A compound according to claim 1, said compound corresponding to formula VII,
wherein n denotes an integer from 2-9 and
X denotes hydrogen, halogen or an alkoxy group.
26. A compound according to claim 25, wherein X denotes hydrogen, chlorine or a methoxy group.
27. A compound according to claim 18, wherein
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-6 residue, a saturated or unsaturated cycloaliphatic C3-7 residue, a phenyl residue or a five- or six-membered heteroaryl residue, wherein the respective ring system may optionally be mono- or polysubstituted or attached via a linear or branched, saturated or unsaturated aliphatic C1-5 bridge.
28. A compound according to claim 19, wherein
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-6 residue, a saturated or unsaturated cycloaliphatic C3-7 residue, a phenyl residue or a five- or six-membered heteroaryl residue, wherein the respective ring system may optionally be mono- or polysubstituted or attached via a linear or branched, saturated or unsaturated aliphatic C1-5 bridge.
29. A compound according to claim 21, wherein
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-6 residue, a saturated or unsaturated cycloaliphatic C3-7 residue, a phenyl residue or a five- or six-membered heteroaryl residue, wherein the respective ring system may optionally be mono- or polysubstituted or attached via a linear or branched, saturated or unsaturated aliphatic C1-5 bridge.
30. A compound according to claim 22, wherein
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-6 residue, a saturated or unsaturated cycloaliphatic C3-7 residue, a phenyl residue or a five- or six-membered heteroaryl residue, wherein the respective ring system may optionally be mono- or polysubstituted or attached via a linear or branched, saturated or unsaturated aliphatic C15 bridge.
31. A compound according to claim 24, wherein
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-6 residue, a saturated or unsaturated cycloaliphatic C3-7 residue, a phenyl residue or a five- or six-membered heteroaryl residue, wherein the respective ring system may optionally be mono- or polysubstituted or attached via a linear or branched, saturated or unsaturated aliphatic C15 bridge.
32. A compound according to claim 25, wherein
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-6 residue, a saturated or unsaturated cycloaliphatic C3-7 residue, a phenyl residue or a five- or six-membered heteroaryl residue, wherein the respective ring system may optionally be mono- or polysubstituted or attached via a linear or branched, saturated or unsaturated aliphatic C15 bridge.
33. A compound according to claim 18, wherein
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-3 residue, a saturated or unsaturated cycloaliphatic C5-6 residue, a phenyl residue or a five- or six-membered heteroaryl residue, wherein the respective ring system may optionally be mono- or polysubstituted with halogen, an alkyl group, an alkoxy group or a trihalogenated alkyl group or may be attached via a linear or branched, saturated or unsaturated aliphatic C1-3 bridge.
34. A compound according to claim 19, wherein
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-3 residue, a saturated or unsaturated cycloaliphatic C5-6 residue, a phenyl residue or a five- or six-membered heteroaryl residue, wherein the respective ring system may optionally be mono- or polysubstituted with halogen, an alkyl group, an alkoxy group or a trihalogenated alkyl group or may be attached via a linear or branched, saturated or unsaturated aliphatic C1-3 bridge.
35. A compound according to claim 21, wherein
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-3 residue, a saturated or unsaturated cycloaliphatic C5-6 residue, a phenyl residue or a five- or six-membered heteroaryl residue, wherein the respective ring system may optionally be mono- or polysubstituted with halogen, an alkyl group, an alkoxy group or a trihalogenated alkyl group or may be attached via a linear or branched, saturated or unsaturated aliphatic C1-3 bridge.
36. A compound according to claim 22, wherein
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-3 residue, a saturated or unsaturated cycloaliphatic C5-6 residue, a phenyl residue or a five- or six-membered heteroaryl residue, wherein the respective ring system may optionally be mono- or polysubstituted with halogen, an alkyl group, an alkoxy group or a trihalogenated alkyl group or may be attached via a linear or branched, saturated or unsaturated aliphatic C1-3 bridge.
37. A compound according to claim 24, wherein
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-3 residue, a saturated or unsaturated cycloaliphatic C5-6 residue, a phenyl residue or a five- or six-membered heteroaryl residue, wherein the respective ring system may optionally be mono- or polysubstituted with halogen, an alkyl group, an alkoxy group or a trihalogenated alkyl group or may be attached via a linear or branched, saturated or unsaturated aliphatic C1-3 bridge.
38. A compound according to claim 25, wherein
R3 denotes a linear or branched, saturated or unsaturated aliphatic C1-3 residue, a saturated or unsaturated cycloaliphatic C5-6 residue, a phenyl residue or a five- or six-membered heteroaryl residue, wherein the respective ring system may optionally be mono- or polysubstituted with halogen, an alkyl group, an alkoxy group or a trihalogenated alkyl group or may be attached via a linear or branched, saturated or unsaturated aliphatic C1-3 bridge.
39. A compound according to claim 18, wherein
R3 denotes a vinyl residue, a cyclopentyl residue, a cyclohexyl residue, a thiophenyl residue or a phenyl residue, wherein the cyclohexyl residue may optionally be attached via a methylene bridge or the phenyl residue may optionally be mono- or polysubstituted with fluorine, chlorine, a methyl group, an isopropyl group, a methoxy group or a trifluoroethyl group or may optionally be attached via a linear saturated aliphatic C1-3 bridge or an ethynyl bridge.
40. A compound according to claim 19, wherein
R3 denotes a vinyl residue, a cyclopentyl residue, a cyclohexyl residue, a thiophenyl residue or a phenyl residue, wherein the cyclohexyl residue may optionally be attached via a methylene bridge or the phenyl residue may optionally be mono- or polysubstituted with fluorine, chlorine, a methyl group, an isopropyl group, a methoxy group or a trifluoroethyl group or may optionally be attached via a linear saturated aliphatic C1-3 bridge or an ethynyl bridge.
41. A compound according to claim 21, wherein
R3 denotes a vinyl residue, a cyclopentyl residue, a cyclohexyl residue, a thiophenyl residue or a phenyl residue, wherein the cyclohexyl residue may optionally be attached via a methylene bridge or the phenyl residue may optionally be mono- or polysubstituted with fluorine, chlorine, a methyl group, an isopropyl group, a methoxy group or a trifluoroethyl group or may optionally be attached via a linear saturated aliphatic C1-3 bridge or an ethynyl bridge.
42. A compound according to claim 22, wherein
R3 denotes a vinyl residue, a cyclopentyl residue, a cyclohexyl residue, a thiophenyl residue or a phenyl residue, wherein the cyclohexyl residue may optionally be attached via a methylene bridge or the phenyl residue may optionally be mono- or polysubstituted with fluorine, chlorine, a methyl group, an isopropyl group, a methoxy group or a trifluoroethyl group or may optionally be attached via a linear saturated aliphatic C1-3 bridge or an ethynyl bridge.
43. A compound according to claim 24, wherein
R3 denotes a vinyl residue, a cyclopentyl residue, a cyclohexyl residue, a thiophenyl residue or a phenyl residue, wherein the cyclohexyl residue may optionally be attached via a methylene bridge or the phenyl residue may optionally be mono- or polysubstituted with fluorine, chlorine, a methyl group, an isopropyl group, a methoxy group or a trifluoroethyl group or may optionally be attached via a linear saturated aliphatic C1-3 bridge or an ethynyl bridge.
44. A compound according to claim 25, wherein
R3 denotes a vinyl residue, a cyclopentyl residue, a cyclohexyl residue, a thiophenyl residue or a phenyl residue, wherein the cyclohexyl residue may optionally be attached via a methylene bridge or the phenyl residue may optionally be mono- or polysubstituted with fluorine, chlorine, a methyl group, an isopropyl group, a methoxy group or a trifluoroethyl group or may optionally be attached via a linear saturated aliphatic C1-3 bridge or an ethynyl bridge.
45. An N,N\u2032-disubstituted piperazine compound according to claim 1, wherein said compound is selected from the group consisting of:
2-Methyl-1-(4-methyl-piperazin-1-yl)-3-phenyl-pentan-3-ol;
3-(4-Chloro-phenyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-Benzyl-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(4-Fluoro-3-methyl-phenyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
2-Methyl-1-(4-methyl-piperazin-1-yl)-3-o-tolyl-pentan-3-ol;
3-Ethyl-4-methyl-5-(4-methyl-piperazin-1-yl)-pent-1-en-3-ol;
3-(4-tert-Butyl-phenyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-Cyclopentyl-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
2-Methyl-1-(4-methyl-piperazin-1-yl)-3-m-tolyl-pentan-3-ol;
3-Cyclohexyl-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(4-Fluoro-phenyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-Ethyl-2-methyl-1-(4-methyl-piperazin-1-yl)-5-phenyl-pentan-3-ol;
3-Ethyl-4-methyl-5-(4-methyl-piperazin-1-yl)-1-phenyl-pent-1-yn-3-ol;
2-Methyl-1-(4-methyl-piperazin-1-yl)-3-thiophen-2-yl-pentan-3-ol;
3-(3-Methoxy-phenyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-Ethyl-2-methyl-1-(4-methyl-piperazin-1-yl)-6-phenyl-hexan-3-ol;
2-Methyl-1-(4-methyl-piperazin-1-yl)-3-p-tolyl-pentan-3-ol;
3-(4-Methoxy-phenyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-phenyl-cyclohexanol;
1-Benzyl-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(4-Fluoro-3-methyl-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-o-tolyl-cyclohexanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-vinyl-cyclohexanol
1-Cyclopentyl-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-m-tolyl-cyclohexanol;
2-(4-Methyl-piperazin-1-ylmethyl)-bicyclohexyl-1-ol;
1-(4-Fluoro-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-phenethyl-cyclohexanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-thiophen-2-yl-cyclohexanol;
1-(2,4-Dichloro-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(3-Methoxy-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-(3-phenyl-propyl)-cyclohexanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-p-tolyl-cyclohexanol;
1-(4-Methoxy-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-Benzyl-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-vinyl-cyclooctanol
1-(4-tert-Butyl-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
1-Cyclopentyl-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-phenethyl-cyclooctanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-phenylethynyl-cyclooctanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-thiophen-2-yl-cyclooctanol;
1-(3-Methoxy-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-(3-phenyl-propyl)-cyclooctanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-p-tolyl-cyclooctanol;
1-(4-Methoxy-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-phenyl-cycloheptanol;
1-(4-Chloro-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-Benzyl-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(4-Fluoro-3-methyl-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-o-tolyl-cycloheptanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-vinyl-cycloheptanol;
1-(4-tert-Butyl-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-Cyclopentyl-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-m-tolyl-cycloheptanol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-2-methyl-3-phenyl-pentan-3-ol;
3-(4-Chloro-phenyl)-1-4-(3-chloro-phenyl)-piperazin-1-yl-2-methyl-pentan-3-ol;
3-Benzyl-1-4-(3-chloro-phenyl)-piperazin-1-yl-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-(4-fluoro-3-methyl-phenyl)-2-methyl-pentan-3-ol;
5-4-(3-Chloro-phenyl)-piperazin-1-yl-3-ethyl-4-methyl-pent-1-en-3-ol;
3-(4-tert-Butyl-phenyl)-1-4-(3-chloro-phenyl)-piperazin-1-yl-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-2-methyl-3-m-tolyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-cyclohexyl-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-(4-fluoro-phenyl)-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-ethyl-2-methyl-5-phenyl-pentan-3-ol;
5-4-(3-Chloro-phenyl)-piperazin-1-yl-3-ethyl-4-methyl-1-phenyl-pent-1-yn-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-2-methyl-3-thiophen-2-yl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-ethyl-2-methyl-6-phenyl-hexan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-2-methyl-3-p-tolyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-(4-methoxy-phenyl)-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-(5-fluoro-2-methoxy-phenyl)-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-(3-fluoro-phenyl)-2-methyl-pentan-3-ol;
3-(3-Chloro-phenyl)-1-4-(3-chloro-phenyl)-piperazin-1-yl-2-methyl-pentan-3-ol;
3-(2-Chloro-benzyl)-1-4-(3-chloro-phenyl)-piperazin-1-yl-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-(4-fluoro-benzyl)-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-(3-methoxy-benzyl)-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-(3-fluoro-benzyl)-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-(2-methoxy-phenyl)-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-2-methyl-3-(2-methyl-benzyl)-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-2-methyl-3-(3-trifluoromethyl-phenyl)-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-2-methyl-3-(3-methyl-benzyl)-pentan-3-ol;
3-(4-Chloro-benzyl)-1-4-(3-chloro-phenyl)-piperazin-1-yl-2-methyl-pentan-3-ol;
3-(2-Chloro-6-fluoro-benzyl)-1-4-(3-chloro-phenyl)-piperazin-1-yl-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-(2,5-dimethyl-benzyl)-2-methyl-pentan-3-ol;
3-(3-Chloro-benzyl)-1-4-(3-chloro-phenyl)-piperazin-1-yl-2-methyl-pentan-3-ol;
1-4-(3-Chloro-phenyl)-piperazin-1-yl-3-(2,4-dichloro-benzyl)-2-methyl-pentan-3-ol;
3-Cyclohexylmethyl-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(5-Fluoro-2-methoxy-phenyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(3-Fluoro-phenyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(3-Chloro-phenyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(3,5-Dichloro-phenyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(2-Chloro-benzyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(4-Fluoro-benzyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(3-Methoxy-benzyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(4-Chloro-3-trifluoromethyl-phenyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(3-Fluoro-benzyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(2-Methoxy-phenyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
2-Methyl-3-(2-methyl-benzyl)-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(3-Chloro-4-fluoro-phenyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
2-Methyl-1-(4-methyl-piperazin-1-yl)-3-(3-trifluoromethyl-phenyl)-pentan-3-ol;
2-Methyl-3-(3-methyl-benzyl)-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(4-Chloro-benzyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(2-Chloro-6-fluoro-benzyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol 3-(2,5-Dimethyl-benzyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(3-Chloro-benzyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
3-(2,4-Dichloro-benzyl)-2-methyl-1-(4-methyl-piperazin-1-yl)-pentan-3-ol;
1-Cyclohexylmethyl-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(5-Fluoro-2-methoxy-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(3-Fluoro-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(3-Chloro-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(3,5-Dichloro-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(2-Chloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(4-Fluoro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(3-Methoxy-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(4-Chloro-3-trifluoromethyl-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(3-Fluoro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(2-Methoxy-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(2-Methyl-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(3-Chloro-4-fluoro-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-(3-trifluoromethyl-phenyl)-cyclohexanol;
1-(3-Methyl-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(4-Chloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(2,5-Dimethyl-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(3-Chloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-(2,4-Dichloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;
1-Cyclohexylmethyl-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
1-(5-Fluoro-2-methoxy-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
1-(2-Chloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
1-(4-Fluoro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
1-(3-Fluoro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
1-(2-Methoxy-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
1-(3-Methyl-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
1-(4-Chloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
1-(2-Chloro-6-fluoro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
1-(2,5-Dimethyl-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
1-(3-Chloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
1-(2,4-Dichloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclooctanol;
1-Cyclohexylmethyl-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(5-Fluoro-2-methoxy-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(3-Fluoro-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(3-Chloro-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(3,5-Dichloro-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(2-Chloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(4-Fluoro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(3-Methoxy-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(4-Chloro-3-trifluoromethyl-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(3-Fluoro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(2-Methoxy-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(2-Methyl-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(3-Chloro-4-fluoro-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-(3-trifluoromethyl-phenyl)-cycloheptanol;
1-(3-Methyl-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(4-Chloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(2-Chloro-6-fluoro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(2,5-Dimethyl-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(3-Chloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-(2,4-Dichloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cycloheptanol;
1-Benzyl-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-vinyl-cyclododecanol;
1-Cyclopentyl-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-phenethyl-cyclododecanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-phenylethynyl-cyclododecanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-thiophen-2-yl-cyclododecanol;
2-(4-Methyl-piperazin-1-ylmethyl)-1-(3-phenyl-propyl)-cyclododecanol;
1-(5-Fluoro-2-methoxy-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
1-(2-Chloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
1-(4-Fluoro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
1-(3-Methoxy-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
1-(3-Fluoro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
1-(2-Methoxy-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
1-(2-Methyl-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
1-(3-Methyl-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
1-(4-Chloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
1-(2,5-Dimethyl-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
1-(3-Chloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
1-(2,4-Dichloro-benzyl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclododecanol;
2-4-(3-Chloro-phenyl)-piperazin-1-ylmethyl-1-cyclohexylmethyl-cyclohexanol;
2-4-(3-Chloro-phenyl)-piperazin-1-ylmethyl-1-(5-fluoro-2-methoxy-phenyl)-cyclohexanol;
2-4-(3-Chloro-phenyl)-piperazin-1-ylmethyl-1-(3-fluoro-phenyl)-cyclohexanol;
1-(3-Chloro-phenyl)-2-4-(3-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(3-Chloro-phenyl)-piperazin-1-ylmethyl-1-(3,5-dichloro-phenyl)-cyclohexanol;
1-(2-Chloro-benzyl)-2-4-(3-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(3-Chloro-phenyl)-piperazin-1-ylmethyl-1-(4-fluoro-benzyl)-cyclohexanol;
2-4-(3-Chloro-phenyl)-piperazin-1-ylmethyl-1-(4-chloro-3-trifluoromethyl-phenyl)-cyclohexanol;
2-4-(3-Chloro-phenyl)-piperazin-1-ylmethyl-1-(3-fluoro-benzyl)-cyclohexanol;
2-4-(3-Chloro-phenyl)-piperazin-1-ylmethyl-1-(2-methoxy-phenyl)-cyclohexanol;
1-(3-Chloro-4-fluoro-phenyl)-2-4-(3-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(3-Chloro-phenyl)-piperazin-1-ylmethyl-1-(3-trifluoromethyl-phenyl)-cyclohexanol;
2-4-(3-Chloro-phenyl)-piperazin-1-ylmethyl-1-(3-methyl-benzyl)-cyclohexanol;
1-(4-Chloro-benzyl)-2-4-(3-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(2-Chloro-6-fluoro-benzyl)-2-4-(3-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(3-Chloro-phenyl)-piperazin-1-ylmethyl-1-(2,5-dimethyl-benzyl)-cyclohexanol;
1-(3-Chloro-benzyl)-2-4-(3-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-phenyl-cyclohexanol;
1-(4-Chloro-phenyl)-2-4-(2-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-Benzyl-2-4-(2-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(4-fluoro-3-methyl-phenyl)-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-O-tolyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-vinyl-cyclohexanol;
1-(4-tert-Butyl-phenyl)-2-4-(2-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-cyclopentyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-m-tolyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-bicyclohexyl-1-ol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(4-fluoro-phenyl)-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-phenethyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-phenylethynyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-thiophen-2-yl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(3-methoxy-phenyl)-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(3-phenyl-propyl)-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-p-tolyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(4-methoxy-phenyl)-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-cyclohexylmethyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(5-fluoro-2-methoxy-phenyl)-cyclohexanol;
1-(3-Chloro-phenyl)-2-4-(2-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(3,5-dichloro-phenyl)-cyclohexanol;
1-(2-Chloro-benzyl)-2-4-(2-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(4-fluoro-benzyl)-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(3-methoxy-benzyl)-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(4-chloro-3-trifluoromethyl-phenyl)-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(3-fluoro-benzyl)-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(2-methoxy-phenyl)-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(2-methyl-benzyl)-cyclohexanol;
1-(3-Chloro-4-fluoro-phenyl)-2-4-(2-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(3-trifluoromethyl-phenyl)-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(3-methyl-benzyl)-cyclohexanol;
1-(4-Chloro-benzyl)-2-4-(2-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(2-Chloro-6-fluoro-benzyl)-2-4-(2-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(2,5-dimethyl-benzyl)-cyclohexanol;
1-(3-Chloro-benzyl)-2-4-(2-chloro-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Chloro-phenyl)-piperazin-1-ylmethyl-1-(2,4-dichloro-benzyl)-cyclohexanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-phenyl-cyclohexanol;
1-(4-Chloro-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-Benzyl-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(4-Fluoro-3-methyl-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-O-tolyl-cyclohexanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-vinyl-cyclohexanol;
1-(4-tert-Butyl-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-Cyclopentyl-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-m-tolyl-cyclohexanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-bicyclohexyl-1-ol;
1-(4-Fluoro-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-phenethyl-cyclohexanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-phenylethynyl-cyclohexanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-thiophen-2-yl-cyclohexanol;
1-(3-Methoxy-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-(3-phenyl-propyl)-cyclohexanol;
1-(2,3-Dichloro-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-p-tolyl-cyclohexanol;
1-(4-Methoxy-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-Cyclohexylmethyl-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(5-Fluoro-2-methoxy-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(3-Fluoro-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(3-Chloro-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(3,5-Dichloro-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(2-Chloro-benzyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(4-Fluoro-benzyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(3-Methoxy-benzyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(4-Chloro-3-trifluoromethyl-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(3-Fluoro-benzyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(2-Methoxy-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-(2-methyl-benzyl)-cyclohexanol;
1-(3-Chloro-4-fluoro-phenyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-(3-trifluoromethyl-phenyl)-cyclohexanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-(3-methyl-benzyl)-cyclohexanol;
1-(4-Chloro-benzyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(2-Chloro-6-fluoro-benzyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(2,5-Dimethyl-benzyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(3-Chloro-benzyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-(2,4-Dichloro-benzyl)-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclohexanol;
1-Benzyl-2-4-(2-methoxy-phenyl)-piperazin-1-ylmethyl-cyclododecanol;
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-vinyl-cyclododecanol;
1-Phenethyl-2-phenyl-(4-phenyl-piperazin-1-yl)-methyl-cyclohexanol;
-Benzyl-2-(4-methyl-piperazin-1-yl)-phenyl-methyl-cyclohexanol;
-Benzyl-2-phenyl-(4-phenyl-piperazin-1-yl)-methyl-cyclohexanol;
2-(4-Methyl-piperazin-1-yl)-phenyl-methyl-1-phenethyl-cyclohexanol; and
2-4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl-1-phenethyl-cyclododecanol.
46. A method for producing an N,N\u2032-disubstituted piperazine compound according to claim 1, comprising the steps of:
A1) reacting a ketone corresponding to formula (1),
\u2003with paraformaldehyde and a piperazine corresponding to formula (2),
\u2003by a Mannich reaction in a suitable solvent;
working up the reaction mixture; and
isolating the product corresponding to formula (3)
or
A2) reacting an enamine corresponding to formula (1a), wherein R denotes an aliphatic C1-6 residue, a morpholinyl, piperidyl or pyrrolidinyl residue, wherein the two residues R are the same or different,
\u2003with an aldehyde corresponding to formula (4), wherein R4 is not hydrogen
\u2003and a piperazine corresponding to formula (2),
\u2003by a Mannich reaction in the presence of triethylamine, chlorotrimethylsilane and sodium iodide in a suitable solvent;
working up the reaction mixture; and
isolating the product corresponding to formula (3a)
or
A3) reacting an enamine corresponding to formula (1a), wherein R denotes an aliphatic C1-6 residue, a morpholinyl, piperidyl or pyrrolidinyl residue, wherein the two residues R are the same or different
\u2003with an iminium salt corresponding to formula (5), wherein R4 is not hydrogen and Y\u2212 denotes a chloride, bromide, iodide or AlCl4\u2212 ion,
\u2003by a Mannich reaction in a suitable solvent;
working up the reaction mixture; and
isolating the product corresponding to formula (3a)
and
B) reacting a compound corresponding to formula (3) or (3a) with a Grignard compound or an organolithium compound corresponding to formulae R3MgCl, R3MgBr, R3MgI, MgR32 or LiR3, in a suitable solvent;
working up the reaction mixture; and
isolating the compound corresponding to formula I.
46. The method of claim 45, wherein the solvent of step A1) is ethanol with the addition of hydrochloric acid or is acetic acid, or with heating provided to said Mannich reaction.
47. The method of claim 45, wherein in step A2), the piperazine corresponding to formula (2) is provided in the form of the hydrochloride thereof.
48. The method of claim 45, wherein the solvent of step A2) or A3) is acetonitrile.
49. The method of claim 45, wherein the solvent of step B) is diethyl ether or tetrahydrofuran.
50. A pharmaceutical formulation comprising at least one compound according to claim 1 as active ingredient and a physiologically acceptable auxiliary substances.
51. A method of alleviating pain in a larger mammal comprising the step of administering to said mammal an effective pain-alleviating amount of a pharmaceutical formulation according to claim 50.
52. A method of anaesthetizing a mammal comprising the step of administering to said mammal an anaesthetically effective amount of a pharmaceutical formulation according to claim 50.
53. A method of treating or inhibiting a disease or condition selected from the group consisting of arrhythmia, emesis, cardiovascular disease, urinary incontinence, diarrhea, pruritus, dependency on alcohol, drugs, or other substances, inflammation, depression, or for increasing vigilance or increasing libido in a mammal comprising the step of administering to said mammal an effective amount of a pharmaceutical formulation according to claim 50.
54. A method of achieving a nootropic or neurotropic effect in a mammal, said method comprising the step of administering an effective amount of a pharmaceutical formulation according to claim 50.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
What is claimed is:
1. A jig for positioning and fixing a workpiece to a workbench (12), said jig comprising:
a first clamping member (13) having a screw hole (13b) extending in the vertical direction;
a second clamping member (14), wherein the second clamping member has an insertion hole (14c) extending in the vertical direction and a male screw portion (14a) screwed into a screw hole (13b) of said first clamping member (13) so as to be capable of adjusting a position, and wherein the second clamping member includes a flange portion (14b) at a periphery of the upper portion thereof;
a fixing member (B, N), wherein the fixing member pierces said screw hole (13b) of said first clamping member (13) and said insertion hole (14c) of said second clamping member (14) and fixes said first and second clamping members (13, 14) to said workbench (12); and
a fastening member (15), wherein the fastening member determines a position of said workpiece W with respect to said workbench by utilizing said first and second clamping members (13, 14) fixed to said workbench (12) by said fixing member (B, N), and wherein the fastening member fixes said workpiece (W) moved to a space between a clamping face (13d) of said first clamping member (13) and said flange portion (14b) of said second clamping member (14).
2. The jig according to claim 1, wherein a base member (11) including a male screw portion (11a), a flange portion (11b) and an insertion hole (11c) is further provided, wherein said male screw portion (11a) of said base member (11) is screwed into the lower portion of said screw hole (13b) of said first clamping member (13), wherein said flange portion (11b) of said base member (11) is mounted on said workbench (12), and wherein said fixing member (B, N) is inserted into said insertion hole (11c) of said base member (11).
3. The jig according to claim 1 or 2, wherein said fixing members include a fixing bolt (B) and a nut (N), wherein said fixing bolt (B) is engaged and fixed to said workbench (12) at a head portion (Ba) thereof and inserted into said insertion hole (14c) of said second clamping member (14) at a shaft portion thereof, and wherein said nut (N) is screwed into the distal end of said fixing bolt (B).
4. The jig according to claim 1 or 2, wherein a concave portion (14f) having a diameter larger than that of said insertion hole (14c) is formed in said second clamping member (14), wherein said fixing member includes a fixing bolt (B) and a nut (N), wherein a shaft portion of said fixing bolt (B) is inserted into said insertion hole (14c) of said second clamping member (14), wherein said fixing bolt (B) is engaged and fixed to said workbench (12) at the lower end of a shaft portion thereof by said nut (N), and wherein a head portion (Ba) of said fixing bolt (B) is accommodated in said concave portion (14f).
5. The jig according to claim 1, wherein said fastening member is a clamping bolt (15) screwed downwardly into said screw hole (14e) formed in said flange portion (14b) of said second clamping member (14).
6. The jig according to claim 1, wherein passages (13c, 14d) along which said fixing member is inserted or removed from a side portion are respectively formed in said first and second clamping members (13, 14).
7. The jig according to claim 2, wherein passages (11d, 13c, 14d) along which said fixing member is inserted or removed from a side portion are respectively formed in said base member (11), said first clamping member (13), and said second clamping member (14).
8. The jig according to claim 1, wherein said flange portion (14b) of said second clamping member (14) is caused to protrude in the side direction away from the outer peripheral face of said first clamping member (13), and wherein a fastening member (15a) for fixing said workpiece supported on said workbench (12) is provided at a protrusion portion of said flange portion (14b).
9. The jig according to claim 1, wherein the lower end of said male screw portion (14a) of said second clamping member (14) is supported on the upper face of said workbench (12), and wherein said first clamping member (13) is screwed into an intermediate portion of said male screw portion (14a) so as to be capable of adjusting the position.
10. The jig according to claim 9, wherein said base member (11) supported on said upper face of said workbench (12) is screwed into the lower end portion of said male screw portion (14a) of said second clamping member (14).
11. The jig according to any of claims 1 to 10, wherein a fastening member (15c) which presses said workpiece (W) upwardly is provided at said first clamping member (13).