GB2435826A

GB2435826A - Use of substituted amine compounds in the treatment of food related disorders

Info

Publication number: GB2435826A
Application number: GB0604778A
Authority: GB
Inventors: Helmut Heinrich Buschmann; Jordi-Ramon Quintana Ruiz; Jordi Corbera Arjona; Xavier Codony Soler
Original assignee: Laboratorios del Dr Esteve SA
Current assignee: Esteve Pharmaceuticals SA
Priority date: 2006-03-09
Filing date: 2006-03-09
Publication date: 2007-09-12
Also published as: GB0604778D0

Description

Use of substituted amine compounds for the treatment of food related

disorders The present invention relates to the use of amine compounds of general formula I, A * for the prophylaxis and/or treatment of disorders or diseases that are at least partially ** * med lated via 5-HT6 receptors.

The superfamily of serotonin receptors (5-HT) includes 7 classes (5-HT1-5-HT7) encompassing 14 human subclasses [D. Hoyer, et al., Neuropharmacology, 1997, 36, 419]. The 5-HT6 receptor is the latest serotonin receptor identified by molecular:: cloning both in rats [F.J. Monsma et al., Mol. Pharmacol., 1993, 43, 320; M. Ruat et aL, Biochem. Biophys. Res. Commun., 1993, 193, 268] and in humans [R. Kohen, et al., J. Neurochem., 1996, 66, 47].

Recently, it has been shown that the 5-HI5 receptor plays a role in food ingestion [Neuropharmacology, 41,2001, 210-2191.

Food ingestion disorders, particularly obesity, are a serious, fast growing threat to the health of humans of all age groups, since they increase the risk of developing other serious, even life-threatening diseases such as diabetes or coronary diseases as well.

Therefore an object of the present invention was to provide compounds that can be used for the prophylaxis and/or treatment of disorders or diseases related to 5-HT6 receptors such as food intake related disorders.

Surprisingly, it has been found that the substituted amine compounds of general formula I given below show good to excellent affinity to 5-HT6-receptors. These compounds are therefore particularly suitable for the prophylaxis and/or treatment of disorders or diseases related to 5-HT6-receptors such as food intake related disorders like obesity.

Thus, in one of its aspects the present invention relates to the use of at least one amine compound of general formula I, wherein S. * m isOorl; n isOorl; R1, R2, R3, R4and R5, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -C1-5-alkyl, -C2-5-alkenyl, -0-C1-5- alkyl, -S-C1-5-alkyl, -C(=O)-OH, -C(=O)-C1-5-alkyl, -C1.5-alkylene-C(O)-OH, -C(=O)- O-C1-5-alkyl, -O-C(=O)-C1-5-alkyl, F, Cl, Br, I, -CN, -CF3, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(C1-5-alkyl), -N(C1-5-alkyl)2, -NH(C2-5-alkenyl), -N(C2-5-alkenyl)2, -NO2, - CHO, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH(C1-5-alkyl), -C(=O)-N(C1-5-alkyl)2, - S(=O)2-C1-5-alkyl, -S(=O)2-phenyl, -S(=O)2-OH, -NH-C(=O)-Ci-5-alkyl, -NH-C(=O)- phenyl, -NH-S(=O)2-phenyl, -NH-S(=O)2-C1-5-alkyl, -S(=O)2-NH-phenyl, -S(0)2-NH-C1-5-alkyl and -S(=O)2-N(C1-5-alkyl)2; or two radicals selected from the group consisting of R1, R2, R3, R4 and R5 which are located in adjacent positions on the phenyl ring together form a methylendioxy (-0-CH2-O-) group or ethylendioxy group (-O-CH2-CH2-O-); A represents R6 R9 R7 or R1 R8 H R6 represents a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl and phenyl, which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), -Ci-5-alkyl, -C2-5-alkenyl, -O-C1-5-alkyl, -S-C1-5-alkyl, -C(=0)-OH, -C(=0)-Ci-5-alkyl, -Ci..5-:..

alkylene-C(=O)-OH, -C(=O)-O-C1-5-alkyl, -O-C(=O)-C1-5-alkyl, F, Cl, Br, I, -CN, -CF3, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(C1 -5-alkyl), -N(C1-5-alkyl)2, -N H(C2-5-alkenyl), -N(C2-5-alkenyl)2, -NO2, -CHO, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH(C1-5-alkyl), -:: C(=O)-N(C1-5-alkyl)2, -S(=O)2-Ci-5-alkyl, -S(=O)2-phenyl, -S(0)2-OH, -NH-C(0)- C1-5-alkyl, -NH-C(=O)-phenyl, -NH-S(=O)2-phenyl, -NH-S(=O)2-C1-5-alkyl, -S(0)2-a...

NH-phenyl, -S(=O)2-NH-Ci-5-alkyl and -S(=0)2-N(C1-5-alkyl)2; .. : R7 represents a hydrogen atom; -OH; -0-CH3; -O-C2H5; -0-CH(CH3)2; -O-C(CH3)3; - 0-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, ethenyl, propenyl, butenyl, pentenyl and hexenyl which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -0-C1-5- alkyl, -S-C1-5-alkyl, F, Cl, Br, I, -CN, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(Ci-5-alkyl), -N(C1-5-alkyl)2, -NH(C2-5-alkenyl), -N(C2-5-alkenyl)2 and -NO2; or a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl and phenyl, which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), -C1-5-alkyl, -C2-5-alkenyl, -O-C1-5-alkyl, -S-Ci-5-alkyl, -C(=0)-OH, -C(=0)-C1-5-alkyl, -C1 5-alkylene-C(=O)-OH, -C(O)-0-Ci- 5-alkyl, -0-C(=0)-C1-5-alkyl, F, Cl, Br, I, -CN, -CF3, -OCF3, -SCF3, -OH, -SH, -NH2, - NH(C1-5-alkyl), -N(Ci-5-alkyl)2, -NH(C2-5-alkenyl), -N(C2-5-alkenyl)2, -NO2, -CHO, - CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH(C1-5-alkyl), -C(=O)-N(C1-5-alkyl)2, -S(=O)2-Ci-5-alkyl, -S(=O)2-phenyl, -S(=O)2-OH, -NH-C(0)-C1-5-alkyl, -NH-C(=O)-phenyl, -NH-S(=O)2-phenyl, -NH-S(=O)2-Ci-5-alkyl, -S(=O)2-NH-phenyl, -S(=O)2-NH-C1-5-alkyl and -S(=O)2-N(C 1-5-alkyl)2; R8 represents a radical selected from the group consisting of

NH H'

NH N')

NH NH / a-NH

N

NL/ hQT QD , I -P 1S

H . * -

N5 N N

NH H * I'.. * *

NNH NN 1/>-

N N

NH

H

s _-S. N_N NH NNH HNN {i-) and NJ

N

wherein any hydrogen atom can be substituted with a substituent selected from the group consisting of -C1-5-alkyl, -C2..5-alkenyl, -O-C1-5-alkyl, -S-Ci-5-alkyl, -C(=O)-OH, -C(=O)-C1-5-alkyl, -C-1..5-alkylene-C(=O)-OH, -C(=O)-O-Ci-5-alkyl, -O-C(=O)-C1..5- alkyl, F, Cl, Br, I, -CN, -CF3, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(C1-5-alkyl), -N(C1-5- alkyl)2, -NH(C2-5-alkenyl), -N(C2-5-alkenyl)2, -NO2, -CHO, -CF2H, -CFH2, -C(0)- NH2, -C(=O)-NH(Ci-5-alkyl), -C(=O)-N(Ci.5-alkyl)2, -S(=O)2-C1..5-alkyl, -S(O)2- phenyl, -S(=O)2-OH, -NH-C(=O)-C1-5-alkyl, -NH-C(=O)-phenyl, -NH-S(=O)2-phenyl, - NH-S(=O)2-C1-5-alkyl, -S(=O)2-NH-phenyl, -S(=O)2-NH-C1.. 5-alkyl, -S(0)2-N(C1-5-alkyl)2, phenyl, pyrrolyl, pyridinyl, phenoxy and benzyl; whereby said cyclic substituents pyrrolyl, pyrid inyl, -S(=O)2-phenyl, -N H C(=O)-phenyl, -N H-S(0)2-phenyl, -S(=O)2-NH-phenyl, phenyl, phenoxy and benzyl may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, F, Cl, Br, -CN, -CF3, -OCF3, -SCF3, -OH, -SH, -NH2 and NO2; R9 represents a phenyl radical, which may be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -Ci-5-alkyl, -C2-5-alkenyl, -O-Ci-5-alkyl, -S-Ci-5-alkyl, -C(=O)-OH, -C(=O)-C1-5-alkyl, -Ci..5-alkylene-C(=O)-OH, -C(=O)-O-C1-5-alkyl, -O-C(=O)-Ci-5-alkyl, F, Cl, Br, I, -CN, -CF3, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(Ci-5-alkyl), -N(C1-5-alkyl)2, -NH(C2-5-alkenyl), -N(C2-5-alkenyl)2, -NO2, -CHO, -CF2H, -CFH2, -C(O)-NH2, -C(O)-NH(Ci-5-alkyl), - C(=O)-N(C1-5-alkyl)2, -S(=O)2-Ci-5-alkyl, -S(=O)2-phenyl, -S(=O)2-OH, -NH-C(O)- Ci-5-alkyl, -NH-C(=O)-phenyl, -NH-S(=O)2-phenyl, -NH-S(=O)2-C1-5-alkyl, -S(0)2-I.e.

NH-phenyl, -S(=O)2-NH-Ci-5-alkyl and -S(=O)2-N(Ci-5-alkyl)2; * and R1 represents a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl and cyclohexenyl, which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), -C1-5-alkyl, -C2-5-alkenyl, -O-C1-5-alkyl, -S-C1-5-alkyl, -C(=O)-OH, -C(=O)-C1-5-alkyl, -C1.5-alkylene-C(=O)-OH, - C(=O)-O-C1-5-alkyl, -O-C(=O)-Ci-5-alkyl, F, Cl, Br, I, -CN, -CF3, -OCF3, -SCF3, -OH, - SH, -NH2, -NH(Ci -5-alkyl), -N(C1 -5-alkyl)2, -N H(C2-5-alkenyl), -N(C2-5-alkenyl)2, -NO2, - CHO, -CF2H, -CFH2, -C(=O)-N H2, -C(=O)-NH(C1-5-alkyl), -C(=O)-N(Ci-5-alkyl)2, -S(=O)2-C1-5-alkyl, -S(=O)2-phenyl, -S(=O)2-OH, -NH-C(=O)-Ci-5-alkyl, -NH-C(=O)- phenyl, -NH-S(=O)2-phenyl, -NH-S(=O)2-C1-5-alkyl, -S(=O)2-NH-phenyl, -S(=O)2-NH-Ci-5-alkyl and -S(=0)2-N(Ci-5-alkyl)2; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof; for the manufacture of a medicament for the prophylaxis and/or treatment of a disorder or disease related to food intake.

C1.5-alkyl denotes a linear or branched alkyl radical consisting of 1 to 5 carbon atoms in the chain. Preferably C1..5-alkyl denotes a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl and n-pentyl.

C25-alkenyl denotes a linear or branched alkenyl radical consisting of 2 to 5 carbon atoms in the chain. Preferably C2.5-alkenyl denotes a radical selected from the group consisting of ethenyl, I -propenyl, 2-propenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1-pentenyl and 2-methyl-I -propenyl. * : :: :* S... S * * S. S

Preferred is the use of at least one compound of general formula I given above, wherein m isOorl; n isOorl; R1, R2, R3, R4 and R5, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, n- butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -CF3, -C(=O)-NH2, -C(=O)-NH-CH3, - C(=O)-N(CH3)2, -C(=O)-NH-C2H5, -C(=O)-N(C2H5)2, -O-CH3, -O-C2H5, -O-CH2-CH2- CH3, -O-CH(CH3)2, -O-C(CH3)3, -C(=O)-OH, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)- O-CH2-CH2-CH3, -C(=O)-O-CH(CH3)2, -C(=O)-O-C(CH3)3, F, Cl, Br, I, -CN, -NH2, - NH-CH3, -NH-C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -NH-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; or two radicals selected from the group consisting of R1, R2, R3, R4 and R5 which are located in adjacent positions on the phenyl ring together form a methylendioxy (-0-CH2-0-) group or ethylendioxy group (-O-CH2-CH2-O-); A represents R6 R9 R7 or R1 R8 H R6 represents a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl and phenyl, which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), methyl, * .* . ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -CF3, - C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-N(CH3)2, -C(=0)-NH-C2H5, -C(=O)-N(C2H5)2, -*...

O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -0-CH(CH3)2, -O-C(CH3)3, -C(=0)-OH, -C(=0)-O- CH3, -C(=O)-O-C2H5, -C(=O)-0-CH2-CH2-CH3, -C(=O)-O-CH(CH3)2, -C(=0)-0- C(CH3)3, F, CI, Br, I, -CN, -NH2, -NH-CH3, -NH-C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -NH-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; R7 represents a hydrogen atom; -OH; -0-CH3; -0-C2H5; -0-CH(CH3)2; -0-C(CH3)3; - 0-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, ethenyl, propenyl, butenyl, pentenyl and hexenyl which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -0-CH3, - O-C2H5, -0-CH2-CH2-CH3, -S-CH3, -S-C2H5, -S-CH2-CH2-CH3, F, Cl, Br, I, -CN, - OCF3, -SCF3, -OH, -SH, -NH2, -NH-CH3, -NH-C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -NH-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; or a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl and phenyl, which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -CF3, -C(=0)-NH2, -C(0)- NH-CH3, -C(=O)-N(CH3)2, -C(=O)-NH-C2H5, -C(=O)-N(C2H5)2, -O-CH3, -O-C2H5, -0- CH2-CH2-CH3, -O-CH(CH3)2, -O-C(CH3)3, -C(=O)-OH, -C(=O)-O-CH3, -C(=0)-0- C2H5, -C(=O)-O-CH2-CH2-CH3, -C(=O)-O-CH(CH3)2, -C(=O)-O-C(CH3)3, F, Cl, Br, I, - CN, -NH2, -NH-CH3, -NH-C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -NH-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; R8 represents a radical selected from the group consisting of HQH' p s-NH ,

NH NH NH * ** IS* *

S S /

N

N/ NH * * * * *** * * S...

H * . . S* *

N) C N, N N

NH -H

NNH NN V 1/>-!

N N)-NH

S N

HNN {i-U FJi and NJ

N

wherein any hydrogen atom can be substituted with a substituent selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -CF3, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-N(CH3)2, -C(=O)-NH- C2H5, -C(=O)-N(C2H5)2, -O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, -0- C(CH3)3, -C(=O)-OH, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-O-CH2-CH2-CH3, - C(=O)-O-CH(CH3)2, -C(=O)-O-C(CH3)3, -C(=O)-CH3, -C(=O)-C2H5, -C(=O)-CH2-CH2-CH3, -C(=O)-CH(CH3)2, -C(=0)-C(CH3)3, F, Cl, Br, I, -CN, -NH2, -NH-CH3, -NH-C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -NH-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; R9 represents a phenyl radical, which may be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -CF3, - C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-N(CH3)2, -C(=O)-NH-C2H5, -C(=O)-N(C2H5)2, - O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, -O-C(CH3)3, -C(=O)-OH, -C(0)-O- CH3, -C(=O)-O-C2H5, -C(=O)-O-CH2-CH2-CH3, -C(=O)-O-CH(CH3)2, -C(=O)-O-C(CH3)3, -C(=O)-CH3, -C(=O)-C2H5, -C(=O)-CH2-CH2-CH3, -C(=O)-CH(CH3)2, -: : C(0)-C(CH3)3, F, Cl, Br, I, -CN, -NH2, -NH-CH3, -NH-C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -N H-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; * S * * S and S... * S *5*5

R1 represents a radical selected from the group consisting of cyclopropyl, cyclobutyl, * cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl and cyclohexenyl, which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -CF3, -C(=O)-NH2, -C(=O)- NH-CH3, -C(=O)-N(CH3)2, -C(=O)-NH-C2H5, -C(=O)-N(C2H5)2, -O-CH3, -O-C2H5, -0- CH2-CH2-CH3, -O-CH(CH3)2, -O-C(CH3)3, -C(=O)-OH, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-O-CH2-CH2-CH3, -C(=O)-O-CH(CH3)2, -C(=O)-O-C(CH3)3, -C(=O)-CH3, -C(=O)-C2H5, -C(=O)-CH2-CH2-CH3, -C(O)-CH(CH3)2, -C(=O)-C(CH3)3, F, Cl, Br, I, - CN, -NH2, -NH-CH3, -NH-C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -NH-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.

Particularly preferred is the use of at least one compound of general formula I given above, wherein m isOorl; n isOorl; R1, R2, R3, R4 and R5, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, CI, Br and I; I. * * * * * S. or two radicals selected from the group consisting of R1, R2, R3, R4 and R5 which are located in adjacent positions on the phenyl ring together form a methylendioxy (-0-CH2-O-) group or ethylendioxy group (-O-CH2-CH2-O-); *:.*.

Arepresents *...* S... * S.. * . S S. S R6 R9

R7 or R1 R8 H R6 represents an unsubstituted radical selected from the group consisting of cyclopentyl, cyclohexyl and cycloheptyl; or a phenyl radical which may be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -0-CH(C H3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, CI and Br; R7 represents a hydrogen atom; -OH; -O-CH3; -O-C2H5; -O-CH(CH3)2; -O-C(CH3)3; -O-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl and sec-butyl; or a phenyl radical which may be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl and Br; R8 represents a radical selected from the group consisting of f CH CH3 CH3 NL> , and CH3 R9 represents phenyl radical which may be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -O-CH3, -0-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-*.

butyl, sec-butyl, isobutyl, F, Cl and Br; * * I... S.. * . S S. S and

R1 represents a radical selected from the group consisting of cyclopentyl, cyclohexyl and cycloheptyl; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereolsomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.

More particularly preferred is the use of at least one compound of general formula Ia, Do\ )ma R1 a N) I)-r2a )-/ I-' R4a R3 Ia ** I * wherein ma isOorl; * * * I I. ** R1a, R2, R3, R4 and R5, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, -O-C2H5, -O-CH2-: : ::: CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Br and I; or two radicals selected from the group consisting of R, R2, R3a, R and R5 which are located in adjacent positions on the phenyl ring together form a methylendioxy (-O-CH2-O-) group or ethylendioxy group (-O-CH2-CH2-O-); R7a represents a hydrogen atom; -OH; -O-CH3; -O-C2H5; -O-CH(CH3)2; -O-C(CH3)3; -O-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl and sec-butyl; or a phenyl radical which may be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -O-CH3, -O-C2H5, -O-CH2-C H2-CH3, -0-C H(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl and Br; and A, B, C, 0 and E, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Brand I; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.

Also more particularly preferred is the use of at least one compound of general: :: formula Ib, : Rib.;;:;: R5b Ib, wherein mb isOorl; R, R2b, R3b, R4b and R5b, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, -O-C2H5, -O-CH2- CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Br and I; or two radicals selected from the group consisting of R, R2", R3b, R4L and R51' which are located in adjacent positions on the phenyl ring together form a methylendioxy (-O-CH2-O-) group or ethylendioxy group (-O-CH2-CH2-O-); and R7b represents a hydrogen atom; -OH; -O-CH3; -O-C2H5; -O-CH(CH3)2; -0-C(CH3)3; -O-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl and sec-butyl; or a phenyl radical which may be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -O-CH3, -O-C2H5, -O-CH2-CH2-C H3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl and Br; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, * preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof. *::::* * * * * S Also more particularly preferred is the use of at least one compound of general formula Ic, C%) R4C R3C Ic, wherein mc isOorl; R, R2C, R3C, R and R5C, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, -O-C2H5, -O-CH2- CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Br and I; or two radicals selected from the group consisting of R, R2C, R3C, R4C and R5C which are located in adjacent positions on the phenyl ring together form a methylendioxy (-O-CH2-O-) group or ethylendioxy group (-O-CH2-CH2-O-); R7C represents a hydrogen atom; -OH; -O-CH3; -O-C2H5; -O-CH(CH3)2; -O-C(CH3)3; -O-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, -butyl, tert-butyl, isobutyl and sec-butyl; or a phenyl radical which may be unsubstituted or substituted with 1, 2, 3, 4 or 5 * substituent(s) independently selected from the group consisting of -O-CH3, -O-C2H5, -pm O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, a,. *.ep

sec-butyl, isobutyl, F, Cl and Br; *:::: and A, B, C, D and E, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Brand I; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.

Also more particularly preferred is the use of at least one compound of general formula Id, o)md R1 Id, R:R2d wherein

-p

md isOorl; S-I.

Rd, R2d, R3d, R4d and R5d, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, -O-C2H5, -O-CH2- CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Br and I; or two radicals selected from the group consisting of Rd, R2d, R3d, R and R5d which are located in adjacent positions on the phenyl ring together form a methylendioxy (-O-CH2-O-) group or ethylendioxy group (-O-CH2-CH2-O-); and R7d represents a hydrogen atom; -OH; -O-CH3; -O-C2H5; -O-CH(CH3)2; -0-C(CH3)3; -O-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl and sec-butyl; or a phenyl radical which may be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -O-CH3, -O-C2H5, - 0-C H2-CH2-C H3, -0-C H(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl and Br; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.

Also more particularly preferred is the use of at least one compound of general formula le, I *

S S S

B

Di7O)rne Rie R5e \ )-r2e J.._, r R4 R3 le, wherein me isOorl; R1e, R2, R3, R4 and R, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -0-CH3, -0-C2H5, -0-CH2- CH2-CH3, -0-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Br and I; or two radicals selected from the group consisting of R1, R2, R3, R4 and R5 which are located in adjacent positions on the phenyl ring together form a methylendioxy (-0-CH2-0-) group or ethylendioxy group (-0-CH2-CH2-0-); R7 represents a hydrogen atom; -OH; -0-CH3; -0-C2H5; -O-CH(CH3)2; -O-C(CH3)3; -0-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl and sec-butyl; or a phenyl radical which may be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -O-CH3, -O-C2H5, -O-CH2-C H2-CH3, -0-C H(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl and Br; and A, B, C, D and E, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -0-CH3, -0-C2H5, -0-CH2-CH2-CH3, - 0-CH (CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Br and I;

S * S S * S*

optionally in form of one of its stereoisomers, preferably enantiomers or * .: diasteromers, a racemate or in form of a mixture of at least two of its stereolsomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically * acceptable salt thereof, or a corresponding solvate thereof. *..: S... * S S...

Even more particularly preferred is the use of at least one compound of general. ::: : formula I selected from the group consisting of [1] 2-[4-chlorophenyl]-[N-(2-[3,4-d imethoxyphenyljethyl)-N-methyl-3-aminopropoxy]methylj-1-methyl-I H-imidazole, [2] 4-[4-ch lorophenyl]-[N-(2-[3,4-d imethoxyphenyl]ethyl)-N-methyl-3-am inopropoxy]methyl]-I-methyl-I H-pyrazole, [3] 2-El -[4-ch lorophenylj-I -[N-(2-[3,4-d imethoxyphenyl]ethyl)-N-methyl-3-aminopropoxylethyl]-1 -methyl-I H-imidazole, [4] 5-[4-chlorophenyl]-[N-(2-[3,4-d imethoxyphenyl]ethyl)-N-methyl-3-aminopropoxy]methylj-1-methyl-I H-pyrazole, [5] 5-El -[4-ch lorophenyl]-I -[N-(2-[3,4-d imethoxyphenyl]ethyl)-N-methyl-3-am inopropoxy]ethyl]-1-methyl-I H-pyrazole, [6] N-(2-fluorophenethyl)-3-( I -(4-fluorophenyl)-i -(1-methyl-I H-im idazol-2-yl)ethoxy)-N-methylpropan-1 -amine, [7] 3-( 1 -(4-chlorophenyl)-I -(1-methyl-i H-imidazol-2-yl)ethoxy)-N-(2-fluorophenethyl)-N-methylpropan-i-amine, [8] N-(4-fluorophenethyl)-N-methyl-3-( I -(1-methyl-i H-im idazol-2-yl)-1 -phenylethoxy)propan-1 -amine, [9] 3-( I -cyclohexyl-I -(I-methyl-i H-imidazol-2-yl)ethoxy)-N-(4-fluorophenethyl)-N-methylpropan-1 -amine, : : : * [10] 3-(I -cyclohexyl-I -(I -methyl-I H-imidazol-2-yl)ethoxy)-N-methyl-N-phenethylpropan-i -amine, [11] 3-(i -(4-fluorophenyl)-1 -(I -methyl-I H-pyrazol-5-yl)ethoxy)-N-methyl-N-phenethylpropan-1 -amine, * :: [12] 3-( I -(4-chlorophenyl)-I -(1-methyl-I H-pyrazol-5-yl)ethoxy)-N-(4-fluorophenethyl)-N-methylpropan-I-amine, [13] N-(4-fluorophenethyl)-3-(I -(4-fluorophenyl)-I -(1 -methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-I -amine, [14] 3-(i -(4-fluorophenyl)-I -(1-methyl-I H-pyrazol-5-yl)ethoxy)-N-(4-methoxyphenethyl)-N-methylpropan-I-amine, [15] 3-(1 -cyclohexyl-1 -(1 -methyl-I H-pyrazol-5-yl)ethoxy)-N-(4-methoxyphenethyl)-N-methylpropan-1 -amine, [16] N-(2-(4-fluorophenoxy)ethyl)-3-( 1 -(4-fluorophenyl)-I -(1-methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine, [17] 3-( 1 -cyclohexyl-I -(I-methyl-IH-pyrazol-5-yl)ethoxy)-N-(2-(4-fluorophenoxy)ethyl)-N-methylpropan-I -amine, [18] 4-cyclopropyl-N-methyl-N-phenethyl-4-phenylbutan-1 -amine, [19] N-(2-(benzo[d][ I,3]d ioxol-5-yloxy)ethyl)-3-( 1 -(4-chlorophenyl)-I -(1-methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-1-amine, [20] N-(3,4-d imethoxyphenethyl)-3-( 1 -(4-chlorophenyl)-1 -(thiophen-2-yl)ethoxy)-N-methylpropan-1 -amine, a * * a * a.

[21] N-(3,4-d imethoxyphenethyl)-3-((4-chlorophenyl)(2-methyl-2H-1,2,4-triazol-3-S yl)methoxy)-N-methylpropan-I -amine, * * [22] N-(3,4-dimethoxyphenethyl)-3-(1 -(4-chlorophenyl)-I -(2-methyl-2H-1,2,4-* triazol-3-yl)ethoxy)-N-methytpropan-1 -amine, * I **** ***. * a e. *

[23] 3-( 1 -(4-chlorophenyl)-I -(1-methyl-I H-pyrazol-5-yl)ethoxy)-N-methyl-N-phenethylpropan-1 -amine, [24] 4-((3,4d imethoxyphenethyl)(methyl)amino)-I -(4-ch lorophenyl)-I -(I-methyl-I H-pyrazol-5-yl)butan-l -ol, [25] (-)-N-(2-(benzo[d][ 1, 3Jd ioxol-5-yloxy)ethyl)-3-( I -(4-chiorophenyl)-I -(1-methyl- 1 H-pyrazol-5-yI)ethoxy)-N-methylpropan-1-amine, [26] (+)-N-(2-(benzo[d][ 1, 3]dioxol-5-yloxy)ethyl)-3-( 1 -(4-ch lorophenyl)-1 -(I-methyl- 1 H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine, [27] 4-((3,4-dimethoxyphenethyl)(methyl)amino)-1 -(4-chlorophenyl)-I -(I-methyl- 1 H-imidazol-2-yl)butan-1-ol, [28] 4-((3,4-d imethoxyphenethyl)(methyl)amino)-I -(4-ch lorophenyl)-1 -(2-methyl-2H-I,2,4-triazol-3-yl)butan-I -01, [29] 4-((3,4-dimethoxyphenethyl)(methyl)am mo)-I -(4-methyl-4H-1,2,4-triazol-3-yl)-I -phenylbutan-1 -01, [30] 4-((3,4-dimethoxyphenethyl)(methyl)amino)-1 -(1-methyl-I H-imidazol-2-yI)-1-phenytbutan-I -01, [31] 4-((3,4-d imethoxyphenethyl)(methyl)amino)-I -(I-methyl-I H-pyrazol-5-yl)-I -phenylbutan-1 -01, [32] 3-( I -(4-chlorophenyl)-I -(I-methyl-I H-pyrazol-5-yl)ethoxy)-N-methyl-N-(2-phenoxyethyl)propan-1 -amine, [33] 3-((4-chlorophenyl)(2-methyl-2H-I,2,4-triazol-3-yl)methoxy)-N-methyl-N(2-phenoxyethyl)propan-I -amine,

S S...

[34] N-(2-(benzo[d][I,3jdioxol-5-yloxy)ethyl)-3-((4-chlorophenyl)(1 -methyl-I H-.::: pyrazol-5-yI)methoxy)-N-methylpropan-I -amine, [35] N-methyl-4-( 1-methyl-I H-pyrazol-5-yI)-N-phenethyl-4-phenylbutan-I -amine, [36] N-(2-(benzo[d][l, 3Jd ioxol-5-yloxy)ethyl)-N-methyl-3-(( I-methyl-I H-pyrazol-5-yl)(phenyl)methoxy)propan-1 -amine, [37] N-(2-(benzo[dJ[ 1, 3]d ioxol-5-yloxy)ethyl)-3-(cyclopropyl( 1-methyl-I H-pyrazol-5-yI)(phenyl)methoxy)-N-methylpropan-l -amine, [38] N-(2-(benzo[d][ 1, 3]dioxol-5-yloxy)ethyl)-3-( 1 -(4-fluorophenyl)-1 -(1-methyl-I H-pyrazol-5-yI)ethoxy)-N-methylpropan-1 -amine, [39] N-(2-(benzo[d][ 1, 3Jd ioxol-5-yloxy)ethyl)-3-( 1 -(3,4-d ich lorophenyl)-1 -(1-methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine, [40] N-(4-fluorophenethyl)-3-( 1 -(3,4-d ich lorophenyl)-I -(1-methyl-i H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine, [411 3-( 1 -(4-chlorophenyl)-1 -(i-methyl-i H-pyrazol-5-yl)ethoxy)-N-(2-(3,4-d imethoxyphenoxy)ethyl)-N-methylpropan-1-amine, [42] N-(2-(benzo[d][ I, 3]dioxol-5-yloxy)ethyl)-3-( I -(4-ch lorophenyl)-1 -(1-methyl-I H-imidazol-2-yl)ethoxy)-N-methylpropan-I -amine, [43J N-(2-(benzo[d][ 1, 3]dioxol-5-yloxy)ethyl)-N-methyl-3-( I -(i-methyl-I H-im idazol- 2-yl)-I -phenylethoxy)propan-I -amine, I. [44] N-(2-(benzo[d][ 1, 3]d ioxol-5-yloxy)ethyl)-N-methyl-3-( I -(1-methyl-I H-pyrazol-5-yl)-i -phenylethoxy)propan-i -amine, [45] N-(2-(benzo[d][l, 3]d ioxol-5-yloxy)ethyl)-3-( I -(4-methoxyphenyl)-I -(i-methyl-*; ::: I H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine, [46] N-(4-fluorophenethyl)-3-( I -(4-methoxyphenyl)-I -(i-methyl-I H-pyrazol-5-yl)ethoxy)-N-methy!propan-i -amine, [47] 3-( I -(4-chlorophenyl)-l -(i-methyl-I H-pyrazol-5-yl)ethoxy)-N-(2-(4-fluorophenoxy)ethyl)-N-methylpropan-I -amine, [48] N-(2-(4-fluorophenoxy)ethyl)-3-( I -(4-methoxyphenyl)-I -(I -methyl-I H-pyrazol- 5-yl)ethoxy)-N-methylpropan-1 -amine, [49] N-(2-(benzo[d][1, 3]d ioxol-5-yloxy)ethyl)-3-( I -cyclohexyl-I -(I-methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-I -amine,

-

[50] N-(4-chlorophenethyl)-3-( I -(4-ch lorophenyl)-1 -(1-methyl-I H-im idazol-2-yl)ethoxy)-N-methylpropan-I -amine, [51] N-(4-chlorophenethyl)-3-( I -(4-ch lorophenyl)-1 -(1-methyl-1 H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine, [52] N-(4-methoxyphenethyl)-3-( 1 -(4-chlorophenyl)-1 -(1-methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine, [53] N-(4-fluorophenethyl)-3-(cyclohexyl( 1 -methyl-l H-im idazol-2-yl)methoxy)-N-methylpropan-1 -amine, * S S * *5 [54] N-methyl-3-((1 -methyl-I H-imidazol-2-yl)(phenyl)methoxy)-N-phenethylpropan-s's.

1-amine, * [55] N-methyl-3-(1 -(1 -methyl-I H-imidazol-2-yl)-I -phenylethoxy)-N-phenethylpropan-1-amine and * : :: :* S... * S S

[56] 3-(cyclohexyl(I -methyl-I H-imidazol-2-yl)methoxy)-N-methyl-N-phenethylpropan-1 -amine; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.

In another aspect the present invention relates to the use of at least one substituted amine compound of general formula I, Ia, Ib, Ic, Id or le given above, in the following text referred to as compound of general formula I, optionally in form of one of their stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof, for the manufacture of a medicament suitable for 5-HT6-receptor regulation, preferably for the prophylaxis and/or treatment of a disorder or a disease that is least partially mediated via 5-HT6-receptors.

In another aspect the present invention relates to the use of at least one substituted amine compound of general formula I given above, optionally in form of one of their stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof, for the manufacture of a medicament for the regulation of appetite; for the maintenance, increase or reduction of body weight; or for the prophylaxis and/or treatment of obesity, bulimia, anorexia, cachexia or type II diabetes (non insulin dependent diabetes mellitus), for the prophylaxis and/or treatment of stroke; * seizures; migraine; head trauma; epilepsy; irritable colon syndrome; irritable bowel syndrome; disorders of the central nervous system; depression; bipolar disorders; obsessive compulsory disorder; sleep disorders; psychosis; neurodegenerative disorders, preferably selected from the group consisting of Morbus Alzheimer, : Morbus Parkinson, Morbus Huntington and Multiple Sclerosis; schizophrenia; chronic * S...

intermittent hypoxia; convulsions; or hyperactivity disorder (ADHD, attention * : : : deficit/hyperactivity disorder).

More preferred is the use of at least one substituted amine compound of general formula I as defined above, optionally in form of one of their stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof, for the preparation of a medicament for the regulation of appetite; for the maintenance, increase or reduction of body weight; or for the prophylaxis and/or treatment of obesity, bulimia, anorexia, cachexia or type II diabetes (non insulin dependent diabetes mellitus).

Most preferred is the use of at least one substituted amine compound of general formula I as defined above, optionally in form of one of their stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof, for the preparation of a med icament for the prophylaxis and/or treatment of obesity.

The inventively obtained medicament may be in any form suitable for the application to patients and can be produced by standard procedures known to those skilled in the art. The composition of the medicament may vary depending on the route of administration.

Such medicaments may be produced according to standard procedures known to those skilled in the art, e.g. from the tables of contents from,,Pharmaceutics: the Science of Dosage Forms", Second Edition, Aulton, M.E. (Ed.) Churchill Livingstone, Edinburgh (2002); ,,Encyc!opedia of Pharmaceutical Technology", Second Edition, * Swarbrick, J. and Boylan J.C. (Eds.), Marcel Dekker, Inc. New York (2002); ,,Modern Pharmaceutics", Fourth Edition, Banker G.S. and Rhodes C.T. (Eds.) Marcel Dekker, Inc. New York 2002 and The Theory and Practice of Industrial Pharmacy", Lachman L., Lieberman H. and Kanig J. (Eds.), Lea & Febiger, Philadelphia (1986). The respective descriptions are incorporated by reference and form part of the present

disclosure. * : : ::

The medicament obtained according to the present invention may, for example, be administered parentally in combination with conventional injectable liquid carriers, such as water or suitable alcohols. Conventional pharmaceutical excipients for injection, such as stabilizing agents, solubilizing agents, and buffers, may be included in such injectable compositions. These medicaments may for example be injected intramuscularly, intraperitoneally, or intravenously. The medicament obtained according to the present invention may also be administered topically, e.g. by means of a transdermal therapeutic system (US), or via a suppository.

In a preferred embodiment of the present invention, the medicament is suitable for oral administration.

Suitable oral administration forms include tablets, dragees, capsules, syrups, gels, juices (oil-or water-based), chewing gums, sprays, aqueous or oily suspensions, or dry powdered forms, preferably in a sachet, suitable for reconstitution with water or other suitable liquid medium before use.

Other suitable oral administration forms are multiparticulate formulations, preferably microtablets, microparticles, nanoparticles, pellets or granules, optionally compressed into a tablet, filled into a capsule or suspended in a suitable liquid.

Suitable liquids are known to those skilled in the art.

The inventively obtained medicament may also comprise at least one substituted amine compound of general formula I given above at least partially in sustained-release form. By incorporating one or more of the substituted amine compounds of general formula I given above at least partially or completely into a sustained-release: . form it is possible to extend the duration of their effect, allowing for the beneficial effects of such a sustained release form, e.g. the maintenance of optimal therapeutical plasma or tissue concentrations.

Suitable sustained-release forms as well as materials and methods for their preparation are known to those skilled in the art, e.g. from the tables of contents from Modified-Release Drug Delivery Technology", Rathbone, M.J. Hadgraft, J. and Roberts, M.S. (Eds.), Marcel Dekker, Inc., New York (2002); ,,Handbook of Pharmaceutical Controlled Release Technology", Wise, D.L. (Ed.), Marcel Dekker, Inc. New York, (2000);"Controlled Drug Delivery", Vol. I, Basic Concepts, Bruck, S.D.

(Ed.), CRC Press Inc., Boca Raton (1983) and from Takada, K. and Yoshikawa, H., Oral Drug delivery", Encyclopedia of Controlled Drug Delivery, Mathiowitz, E. (Ed.), John Wiley & Sons, Inc., New York (1999), Vol. 2, 728-742; Fix, J., Oral drug delivery, small intestine and colon", Encylopedia of Controlled Drug Delivery, Mathiowitz, E. (Ed.), John Wiley & Sons, Inc., New York (1999), Vol. 2, 698-728. The respective descriptions are incorporated by reference and are part of the present

disclosure.

If the med icament obtained according to the present invention comprises at least one of the substituted amine compounds of general formula I at least partially in a sustained-release form, said sustained release may preferably be achieved by the application of at least one coating or provision of a matrix comprising at least one sustainedrelease material.

The sustained-release material is preferably based on an optionally modified, water-insoluble, natural, semisynthetic or synthetic polymer, or a natural, semisynthetic or synthetic wax or fat or fatty alcohol or fatty acid, or on a mixture of at least two of these afore mentioned components.

The water-insoluble polymers used to produce a sustained-release material are preferably based on an acrylic resin, which is preferably selected from the group of poly(meth)acrylates, particularly preferably poly(C, 4alkyl (meth)acrylates, poly(Ci4dialkylamino(Ci4alkyI (meth)acrylates and/or copolymers or mixtures. " thereof, and very particularly preferably copolymers of ethyl acrylate and methyl methacrylate with a monomer molar ratio of 2:1 (Eudragit NE300 ), copolymers of ethyl acrylate, methyl methacrylate and trimethylammonium ethyl methacrylate-chloride with a monomer molar ratio of 1:2:0.1 (Eudragit RS ), copolymers of ethyl acrylate, methyl methacrylate and trimethylammonium ethyl methacrylate-chioride with a monomer molar ratio of 1:2:0.2 (Eudragit RL ), or a mixture of at least two of. :: the above-mentioned copolymers. These coating materials are commercially available as 30 wt.% aqueous latex dispersions, i.e. as Eudragit RS3OD , Eudragit NE3OD or Eudragit RL3OD , and may also be used as such for coating purposes.

In another embodiment, the sustained-release material is based on water-insoluble cellulose derivatives, preferably alkyl celluloses, particularly preferably ethyl cellulose, or cellulose esters, e.g. cellulose acetate. Aqueous ethyl cellulose dispersions are commercially available, for example, under the trademarks Aquacoat or Surelease .

As natural, semisynthetic or synthetic waxes, fats or fatty alcohols, the sustained-release material may be based on carnauba wax, beeswax, glycerol monostearate, glycerol monobehenate, glycerol d itripalmitostearate, microcrystalline wax, cetyl alcohol, cetylstearyl alcohol or a mixture of at least two of these components.

The afore mentioned polymers of the sustained-release material may also comprise a conventional, physiologically acceptable plasticizer in amounts known to those skilled in the art.

Examples of suitable plasticizers are lipophilic diesters of a C6-C40 aliphatic or aromatic dicarboxylic acid and a C1-C8 aliphatic alcohol, e.g. dibutyl phthalate, diethyl phthalate, dibutyl sebacate or diethyl sebacate, hydrophilic or lipophilic citric acid esters, e.g. triethyl citrate, tributyl citrate, acetyltributyl citrate or acetyltriethyl citrate, polyethylene glycols, propylene glycol, glycerol esters, e.g. triacetin, Myvacet (acetylated mono-and diglycerides, C23HO5 to C25H4707), medium-chain triglycerides (Miglyol ), oleic acid or mixtures of at least two of said plasticizers.

Aqueous dispersions of Eudragit RS and optionally Eudragit RL preferably contain: . triethyl citrate. The sustained-release material may comprise one or more plasticisers. : in amounts of, for example, 5 to 50 wt.% based on the amount of polymer(s) used.

The sustained-release material may also contain other conventional auxiliary substances known to those skilled in the art, eg. lubricants, coloured pigments or.. ..

surfactants.

The medicament obtained according to the present invention may also have at least one enteric coating which dissolves as a function of pH. Because of this coating, the medicament can pass through the stomach undissolved and the compounds of general formula I are only released in the intestinal tract. The enteric coating preferably dissolves at a pH of between 5 and 7.5.

The enteric coating may be based on any enteric material known to those skilled in the art, e.g. on methacrylic acid/methyl methacrylate copolymers with a monomer molar ratio of 1:1 (Eudragit L ), methacrylic acid/methyl methacrylate copolymers with a monomer molar ratio of 1:2 (Eudragit S ), methacrylic acid/ethyl acrylate copolymers with a monomer molar ratio of 1:1 (Eudragit L3OD-55 ), methacrylic acid/methyl acrylate/methyl methacrylate copolymers with a monomer molar ratio of 7:3:1 (Eudragit FS ), shellac, hydroxypropyl methyl cellulose acetate-succinates, cellulose acetate-phthalates or a mixture of at least two of these components, which can optionally also be used in combination with the above-mentioned water-insoluble poly(meth)acrylates, preferably in combination with Eudragit NE3OD and/or Eudragit RL and/or Eudragit RS .

The coatings of the med icament of the present invention may be applied by the conventional processes known to those skilled in the art, e.g. from Johnson, J.L., Pharmaceutical tablet coating", Coatings Technology Handbook (Second Edition), Satas, D. and Tracton, A.A. (Eds), Marcel Dekker, Inc. New York, (2001), 863-866; Carstensen, 1., ,,Coating Tablets in Advanced Pharmaceutical Solids", Swarbrick, J. (Ed.), Marcel Dekker, Inc. New York (2001), 455-468; Leopold, C.S., ,,Coated dosage forms for colon-specific drug delivery", Pharmaceutical Science & Technology Today, 2(5), 197-204 (1999), Rhodes, C.T. and Porter, S.C., Coatings, in Encyclopedia of Controlled Drug Delivery. Mathiowitz, E. (Ed.), John Wiley & Sons, Inc., New York (1999), Vol. 1, 299-311. The respective descriptions are incorporated by reference e

and are part of the disclosure.

In another embodiment, the med icament obtained according to the present invention may contain one or more of the substituted amine compounds of general formula I *:: ::* not only in sustained-release form, but also in non-retarded form. By combination * : : :.

with the immediately released form, a high initial dose can be achieved for the rapid onset of the beneficial effect. The slow release from the sustained release form then prevents the beneficial effect from diminishing.

Preferred is the administration of the amine compound at a dosage of 0.1 -50 mg/kg/day, more preferred 0.15 -10 mg/kg/day, even more preferred 0.2-5 mg/kg/day Preferably the medicament is designed for once daily, twice daily, or three times daily administration. More preferably the medicament is designed for once daily or twice daily administration, most preferably for once daily administration.

The inventively used substituted amine compounds can be prepared as outlined in Merce-Vidal, R.; Frigola-Constansa; Pares-Coromins, J. FR 2681322; and the references cited therein. The respective description is hereby incorporated by

reference and forms part of the disclosure.

The inventively used substituted amine compounds may, for example, be obtained by the following process, according to which at least one compound of general formula II,

A-OH II,

wherein A has the meaning given above, is reacted with at least one compound of general formula Ill,

XNR III,

wherein R1, R2, R3, R4, R5 and m have the meaning given above and X represents a leaving group, preferably a leaving group selected from the group consisting of chlorine, bromine, mesyloxy and tosyloxy, in at least one reaction medium, preferably in an aprotic solvent, more preferably in an aprotic solvent selected from the group consisting of dimethylsulfoxide, dimethylformamide, toluene, ether, dioxane, diphenylether, chloroform, dichloromethane and carbon tetrachioride, in the presence of at least one base, preferably in the presence of at least one base selected from the group consisting of pyridine, triethylamine, diisopropylethylamine, sodium carbonate, sodium hydroxide, potassium carbonate, potassium hydroxide, cesium carbonate and cesium hydroxide, optionally in the presence of at least one phase transfer catalyst, preferably in the presence of at least one phase transfer catalyst selected from the group consisting of tetrabutylammonium bromide, tetraethylbenzylammonium chloride an crown ethers, to yield a compound of general formula I, -. A R2 wherein R1, R2, R3, R4, R5 and m have the meaning given above and n is 1, which is optionally isolated and/or optionally purified.

The inventively used substituted amine compounds may also be obtained by the following process, according to which at least one compound of general formula II, * * * 0 * **

A-OH II,

wherein A has the meaning given above, is reacted with at least one compound of general formula IV, t0e. * S IV,

wherein Y represents F, Cl, Br, -OH or -OPG, whereby PG represents a protecting group, preferably a protecting group selected from the group consisting of acetyl, tetramethylsilyl, tert-butyl-d imethylsilyl, tert-butyl-d iphenylsilyl and benzyl, and X represents a leaving group, preferably a leaving group selected from the group consisting of chlorine, bromine, mesyloxy and tosyloxy, in at least one reaction medium, preferably in an aprotic solvent, more preferably in an aprotic solvent selected from the group consisting of dimethylsulfoxide, dimethylformamide, toluene, ether, dioxane, diphenylether, chloroform, dichloromethane and carbon tetrach bride, in the presence of at least one base, preferably in the presence of at least one base selected from the group consisting of pyridine, triethylamine, diisopropylethylamine, sodium carbonate, sodium hydroxide, potassium carbonate, potassium hydroxide, cesium carbonate and cesium hydroxide, optionally in the presence of at least one phase transfer catalyst, preferably in the presence of at least one phase transfer catalyst selected from the group consisting of tetrabutylammonium bromide, tetraethylbenzylammonium chloride an crown ethers, to yield a compound of general formula V,

A V,

wherein Y and A have the meaning given above, which is optionally isolated and/or optionally purified, and at least one compound of general formula V is reacted with thionyl chloride, phosphorous pentachloride, oxalyl chloride, mesyl chloride, tosyl chloride or phosphorous pentabromide, in at least one reaction medium, preferably in an aprotic solvent, more preferably in an aprotic solvent selected from the group consisting of.. . dimethylsulfoxide, dimethylformamide, toluene, ether, dioxane, diphenylether, chloroform, dichloromethane and carbon tetrachioride, preferably in the presence of at least one base selected from the group consisting of pyridine, triethylamine, diisopropylethylamine, sodium carbonate, sodium hydroxide, potassium carbonate, potassium hydroxide, cesium carbonate and cesium hydroxide, to yield a compound of general formula VI, VI, wherein X and A have the meaning given above, which is optionally isolated and/or optionally purified, and at least one compound of general formula VI is reacted with at least one compound of general formula VII, R1 R2 R4 R3 VII, wherein R1, R2, R3, R4, R5 and m have the meaning given above, in at least one reaction medium, preferably in an aprotic solvent, more preferably in an aprotic solvent selected from the group consisting of dimethylsulfoxide, dimethylformamide, toluene, ether, dioxane, diphenylether, chloroform, dichloromethane and carbon tetrachloride, in the presence of at least one base, preferably in the presence of at * least one base selected from the group consisting of pyridine, triethylamine, diisopropylethylamine, sodium carbonate, sodium hydroxide, potassium carbonate, *S..

potassium hydroxide, cesium carbonate and cesium hydroxide, optionally in the presence of at least one phase transfer catalyst, preferably in the presence of at least one phase transfer catalyst selected from the group consisting of tetrabutylammon ium bromide, tetraethylbenzylammonium chloride an crown ethers, to yield a compound of general formula I, AjJfR: wherein R1, R2, R3, R4, R5 and m have the meaning given above and n is 1, which is optionally isolated and/or optionally purified.

During the processes described above the protection of sensitive groups or of reagents may be necessary and/or desirable. The introduction of conventional -.-, protective groups as well as their removal may be performed by methods well-known to those skilled in the art.

If the substituted amine compounds of general formula I themselves are obtained in form of a mixture of stereoisomers, particularly enantiomers or diastereomers, said mixtures may be separated by standard procedures known to those skilled in the art, e.g. chromatographic methods or fractionalised crystallisation with chiral reagents.

Salts of the inventively used amine compounds of general formula I and stereoisomers thereof, may be obtained by a process, wherein at least one compound of general formula I having at least one basic group is reacted with at least one inorganic and/or organic acid, preferably in the presence of a suitable *.: reaction medium. Suitable reaction media include, for example, any of the ones given above. Suitable inorganic acids include hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid, suitable organic acids are e. g. citric acid, maleic acid, fumaric acid, tartaric acid, or derivatives thereof, p-toluenesulfonic acid, methanesulfonic acid or camphersulfonic acid. *S.

Salts of the inventively used substituted amine compounds of general formula I or stereoisomers thereof may also be prepared by a method, wherein at least one compound of general formula I having at least one acidic group is reacted with one or more suitable bases, preferably in the presence of a suitable reaction medium.

Suitable bases are e. g. hydroxides, carbonates or alkoxides, which include suitable cations, derived e. g. from alkaline metals, alkaline earth metals or organic cations, e.

g. [NHR4], wherein n is 0, 1, 2, 3 or 4 and R represents a branched or unbranched Ci4-alkyl-radical. Suitable reaction media are, for example, any of the ones given above.

The term "solvate" according to this invention is to be understood as meaning any form of the substituted amine compounds of general formula I in which they have attached to it via non-covalent binding another molecule (most likely a polar solvent) especially including hydrates and alcoholats, e.g. methanolat.

Solvates, preferably hydrates, of the inventively used substituted amine compounds of general formula I, of corresponding stereoisomers, or of corresponding salts thereof may also be obtained by standard procedures known to those skilled in the art.

Those skilled in the art understand that the term substituted amine compounds as used herein is to be understood as encompassing derivatives such as ethers, esters and complexes of these compounds as well. The term "derivatives" as used in this application is defined here as meaning a chemical compound having undergone a chemical derivation starting from an acting (active) compound to change (ameliorate for pharmaceutical use) any of its physicochemical properties, especially a so-called prodrug, e. g. their esters and ethers. Examples of well known methods of producing: *.: a prod rug of a given acting compound are known to those skilled in the art and can be found e. g. in Krogsgaard-Larsen et al., Textbook of Drugdesign and Discovery, Taylor & Francis (April 2002). The respective description is hereby incorporated by

reference and forms part of the disclosure. S...

The purification and isolation of the inventively used substituted amine compounds of general formula (I), of a corresponding stereoisomer, or salt, or solvate or any intermediate thereof may, if required, becarried out by conventional methods known to those skilled in the art, e. g. chromatographic methods or recrystallization.

Pharmacological Methods: I) BINDING TO SEROTONIN RECEPTOR 5-HT6 Cell membranes of HEK-293 cells expressing the 5HT6-human recombinant receptor were supplied by Receptor Biology. In said membranes the receptor concentration is 2.18 pmol/mg protein and the protein concentration is 9.17 mg/mI. The experimental protocol follows the method of B. L. Roth et at. [B. L. Roth, S. C. Craigo, M. S. Choudhary, A. Uluer, F. J. Monsma, Y. Shen, H. Y. Meltzer, D. R. Sibley: Binding of Typical and Atypical Antipsychotic Agents to 5-Hydroxytryptamine-6 and Hydroxytryptamine-7 Receptors. The Journal of Pharmacology and Experimental: ** :* Therapeutics, 1994, 268, 1403] with the following slight changes. The respective part of the literature description is hereby incorporated by reference and forms part of the

disclosure. * S * * * S. 65

The commercial membrane is diluted (1:40 dilution) with the binding buffer: 50 mM Tris-HCI, 10mM MgCl2,0.5 mM EDTA(pH 7.4). The radioligand used is [3H]-LSD at a concentration of 2.7 nM with a final volume of 200 p1. Incubation is initiated by adding 100 p1 of membrane suspension, ( 22.9 pg membrane protein), and is prolonged for 60 minutes at a temperature of 37 C. The incubation is ended by fast filtration in a Brandel Cell Harvester through fiber glass filters made by Schleicher & Schuell GF 3362 pretreated with a solution of polyethylenimine at 0.5 %. The filters are washed three times with three milliliters of buffer Tris-HCI 50 mM pH 7.4. The filters are transferred to flasks and 5 ml of Ecoscint H liquid scintillation cocktail are added to each flask. The flasks are allowed to reach equilibrium for several hours before counting with a Wallac Winspectral 1414 scintillation counter. Non-specific binding is determined in the presence of 100 pM of serotonin. Tests were made in triplicate. The inhibition constants (K, nM) were calculated by nonlinear regression analysis using the program EBDNLIGAND described in Munson and Rodbard, Analytical Biochemistry, 1980, 107, 220, the respective part of which is hereby incorporated by reference and forms part of the disclosure.

II.) FOOD INTAKE MEASUREMENT (BEHAVIOURAL MODEL): Male W rats (200-270 g) obtained from Harlan, S.A. are used. The animals are acclimatized to the animal facility for at least 5 days before they are subjected to any treatment. During this period the animals are housed (in groups of five) in translucid cages and provided with food and water ad libitum. At least 24 hours before the treatment starts, the animals are adapted to single-housing conditions.

The acute effect of the substituted amine compounds according to the present invention in fasted rats is then determined as follows: * S S The rats were fasted for 23 hours in their single homecages. After this period, the rats:5.,: are orally or intraperitoneally dosed with a composition comprising a substituted amine compound or a corresponding composition (vehicle) without said substituted amine compound. Immediately afterwards, the rat is left with preweighed food and.

cumulative food intake is measured after 1, 2,4 and 6 hours. *SSS 05I*

Said method of measuring food intake is also described in the literature publications of Kask et al., European Journal of Pharmacology 414 (2001), 215-224 and Turnbull et al., Diabetes, Vol. 51, August 2002. The respective parts of the descriptions are hereby incorporated by reference and form part of the disclosure.

The present invention is illustrated below with the aid of examples. These illustrations are given solely by way of example and do not limit the general spirit of the present invention.

Examples

Example 6: N-(2-fluorophenethyl)-3-(I -(4-fluorophenyl)-l -(I -methyl-I H-imidazol- 2-yl)ethoxy)-N-methylpropan-1 -amine 1H NMR (300 MHz, CDCI3) & 1.77 (m, 2H), 1.86 (s, 3H), 2.30 (s, 3H), 2.50-2.62 (m, 4H), 2.78 (m, 2H), 2.96 (m, IH), 3.20 (s, 3H), 3.56 (m, IH), 6.80 (d, J 1.2 Hz, IH), 6.91-7.05 (m, 5H), 7.13-7.21 (m, 4H). (Oil).

Example 7: N-(2-fluorophenethyl)-3-(1 -(4-chlorophenyl)-1 -(I -methyl-I H-imidazol-2-yl)ethoxy)-N-methylpropan-1 -amine S. * * S 5 1H NMR (300 MHz, CDCI3) & 1.77 (m, 2H), 1.87 (s, 3H), 2.31 (s, 3H), 2.51-2.64 (m, :5*,: 4H), 2.80 (m, 2H), 2.98 (m, IH), 3.21 (s, 3H), 3.59 (m, IH), 6.80 (d, J= 1.3 Hz, IH), 6.95-7.06 (m, 3H), 7.14-7.26 (m, 6H). (Oil).

Example 8: N-(4-fluorophenethyl)-N-methyl-3-(I -(I -methyl-I H-imidazol-2-yl)-1 -.. . 5..

phenylethoxy)propan-1 -amine 1H NMR (300 MHz, CDCI3) 8: 1.77 (m, 2H), 1.90 (s, 3H), 2.30 (s, 3H), 2.50-2.60 (m, 4H), 2.73 (m, 2H), 2,98 (m, IH), 3.19 (s, 3H), 3.60 (m, IH), 6.80 (d, J= 1.2 Hz, 1H), 6.95 (m, 2H), 7.00 (d, J= 1.2 Hz, IH), 7.15 (m, 2H), 7.20-7.31 (m, 5H). (Oil).

Example II: 3-(I -(4-fluorophenyl)-I -(I -methyl-I H-pyrazol-5-yl)ethoxy)-N-methyl-N-phenethylpropan-1 -amine 1H NMR (300 MHz, Cod3) 8: 1.72-1.84 (m, 5H, (6 = 1.75, s)), 2.32 (s, 3H), 2.54 (m, 2H), 2.63 (m, 2H), 2.79 (m, 2H), 3.03 (m, 1H), 3.44 (s, 3H), 3.52 (m, IH), 6.36 (s, IH), 6.97 (m, 2H), 7.17-7.32 (m, 7H), 7.44 (s, 1H). (Oil).

Example 12: N-(4-fluorophenethyl)-3-(1 -(4-chlorophenyl)-1 -(I -methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-I -amine 1H NMR (300 MHz, CDCI3) 6:1.71-1.82 (m, 5H, (6 = 1.74, s)), 2.29 (s, 3H), 2.42-2.60 (m, 4H), 2.73 (m, 2H), 3.03 (m, IH), 3.44 (s, 3H), 3.49 (m, 1H), 6.36 (s, IH), 6.94 (m, 2H), 7.05-7.28 (m, 6H), 7.43 (s, IH). (Oil).

Example 13: N-(4-fluorophenethyl)-3-(I -(4-fluorophenyl)-I -(1 -methyl-I H-pyrazol- 5-yl)ethoxy)-N-methytpropan-1 -amine 1H NMR (300 MHz, CDCI3) 6: 1.70-1.82 (m, 5H, (6 = 1.74, s)), 2.29 (s, 3H), 2.46-2.60 (m, 4H), 2.72 (m, 2H), 3.02 (m, IH), 3.43 (s, 3H), 3.48 (m, 1H), 6.36 (d, J 1.9 Hz, 1H), 6.90-7.00 (m, 4H), 7.10-7.24 (m, 4H), 7.44 (d, J= 1.9 Hz, 1H). (Oil).

Example 14: N-(4-methoxyphenethyl)-3-(1 -(4-fluorophenyl)-1 -(I -methyl-I H-: imidazol-2-yl)ethoxy)-N-methylpropan-I -amine: * : : 1H NMR (300 MHz, CDCI3) 6: 1.78 (m, 2H), 1.88 (s, 3H), 2.29 (s, 3H), 2.49-2.60 (m, 4H), 2.70 (m, 2H), 2.99 (m, IH), 3.21 (s, 3H), 3.60 (m, IH), 3.77 (s, 3H), 6.81 (m, 3H), 6.96 (m, 3H), 7.10 (m, 2H), 7.20 (m, 2H). (Oil). *04. *04e

Example 15: N-(4-methoxyphenethyl)-3-(1 -cyclohexyl-1 -(1 -methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine 1H NMR (300 MHz, CDCI3) 6: 0.80-1.30 (m, 6H), 1.42 (s, 3H), 1.60-1.88 (m, 6H), 2.05 (m, IH), 2.27 (s, 3H), 2.44 (m, 2H), 2.56 (m, 2H), 2.68 (m, 2H), 2.95 (m, IH), 3.30 (m, IH), 3.78 (s, 3H), 4.00 (s, 3H), 6.02 (d, J= 1.9 Hz, IH), 6.82 (d, J= 8.6 Hz, 2H), 7.10 (d, J= 8.6 HZ, 2H), 7.34 (d, J= 1,9 Hz, IH). (Oil).

Example 16: N-(2-(4-fluorophenoxy)ethyl)-3-(1 -(4-fluorophenyl)-I -(I -methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-I -amine 1H NMR (300 MHz, CDCI3) 6: 1.73-1.83 (m, 5H, (6 = 1.75,s)), 2.32 (s, 3H), 2.57 (m, 2H), 2.78 (t, J= 5.9 Hz, 2H), 3.05 (m, IH), 3.43 (s, 3H), 3.53 (m, IH), 4.01 (t, J= 5.9 Hz, 2H), 6.35 (m, IH), 6.81 (m, 2H), 6.95 (m, 4H), 7.20 (m, 2H), 7.42 (m, 1H). (Oil).

Example 17: 3-(I -cyclohexyl-I -(I -methyl-I H-pyrazol-5-yI)ethoxy)-N-(2-(4-fluorophenoxy)ethyl)-N-methylpropan-1 -amine 1H NMR (300 MHz, CDCI3) & 0.79-1.28 (m, 6H), 1.40 (s, 3H), 1.60-1.83 (m, 6H), 2.02 (m, 1H), 2.29 (s, 3H), 2.48 (m, 2H), 2.74 (m, 2H), 2.96 (m, IH), 3.31 (m, IH), 3.96- 4.00 (m, 5H, (ö = 3.97, s)), 6.00 (d, J= 2.0 Hz, IH), 6.80 (m, 2H), 6.93 (m, 2H), 7.32 (d, J 2.0 Hz, 1H). (Oil).

Example 18: 4-cyclopropyl-N-methyl-N-phenethyl-4-phenylbutan-I -amine 1H NMR (300 MHz, CDCI3) & 1.09 (m, IH), 0.23 (m, IH), 0.34 (m, IH), 0.59 (m, IH), 0.97 (m, 1H), 1.43 (m, 2H), 1.76 (m, 3H), 2.24 (s, 3H), 2.33 (m, 2H), 2.56 (m, 2H), 2.74 (m, 2H), 7.15-7.32 (m, IOH). (Oil).

Example 19: N-(2-(benzo(d][I,3]dioxol-5-yloxy)ethyl)-3-(I -(4-chlorophenyl)-1 -(1-methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-I -amine b: *.

S dill

1H NMR (300 MHz, CDCI3) & 1.75-1.82 (m, 5H, ( = 1.76, s)), 2.33 (s, 3H), 2.58 (t, J= 7.6 Hz, 2H), 2.77 (t, J= 5.9 Hz, 2H), 3.05 (m, IH), 3.44 (s, 3H), 3.55 (m, IH), 3.98 (t, J= 5.9 Hz, 2H), 5.90 (s, 2H), 6.31 (m, 1H), 6.37 (d, J= 2.0 Hz, IH), 6.49 (d, J= 2.2 Hz, 1 H), 6.69 (d, J= 8.6 Hz, I H), 7.21 (m, 4H), 7.44 (d, J= 2.0 Hz, I H). (Oil).

Example 20: N-(3,4-dimethoxyphenethyl)-3-(I -(4-chlorophenyl)-I -(thiophen-2-yl)ethoxy)-N-methylpropan-I -amine 1H NMR (300 MHz, CDCI3) & 1.79 (m, 2H), 1.87 (s, 3H), 2.30 (s, 3H), 2.50-2.62 (m, 4H), 2.70 (m, 2H), 3.34 (m, 2H), 3.85 (s, 3H), 3.86 (s, 3H), 6.72-6.92 (m, 5H), 7. 23 (m, 3H), 7.34 (m, 2H). (Oil).

Example 21: N-(3,4-dimethoxyphenethyl)-3-((4-chlorophenyl)(2-methyl-2H-I,2, 4-triazol-3-yl)methoxy)-N-methylpropan-I -amine 1H NMR (100 MHz, CDCI3) 6: 1.89 (m, 2H), 2.31 (s, 3H), 2.73-2.28 (m, 6H), 3.55 (m, 2H), 3.74 (s, 3H), 3.85 (s, 3H), 3.86 (s, 3H), 5.71 (s, IH), 6.73 (m, 3H), 7.31 (brs, 4H), 7.82 (s, IH). (Oil) Example 22: N-(3,4-dimethoxyphenethyi)-3-(I -(4-chlorophenyl)-I -(2-methyl-2H-I,2,4-triazol-3-yl)ethoxy)-N-methyipropan-I -amine 1H NMR (100 MHz, CDCI3) 6: 1.70-1.99 (m, 5H, (6= 1.92, s)), 2.31 (s, 3H), 2.45-2.70 (m, 6H), 3.50 (s, 3H), 3.60 (m, 2H), 3.85 (s, 3H), 3.87 (s, 3H), 6.73 (m, 3H), 7.23 (m, 4H), 7.85 (s, 1H). (Oil).

Example 23: 3-(I -(4-chlorophenyl)-I -(I -methyl-I H-pyrazol-5-yl)ethoxy)-N-methyl-N-phenethylpropan-I -amine 1H NMR (100 MHz, CDCI3) 6: 1.60-2.00 (m, 5H, (6= 1.76, s)), 2.32 (s, 3H), 2.40-2.80:.

(m, 6H), 3.10 (m, IH), 3.30-3.70 (m, 4H, (6= 3.46, s)), 6.38 (m, IH), 7.10-7-40 (m, 9H), 7.46 (m, IH). (Oil) Example 24: 4-((3,4-dimethoxyphenethyl)(methyl)amino)-I -(4-chlorophenyi)-I -: . (1-methyl-I H-pyrazol-5-yl)butan-1 -01 a... V..,

1H NMR (300 MHz, CDCI3) 6: 1.54 (m, IH), 1.85 (m, IH), 2.20-2.32 (m, 4H, (6= 2.27, )), 2.40-2.82 (m, 7H), 3.64 (s, 3H), 3.86 (s, 3H), 3.88 (S, 3H), 6.23 (d, J= 1.8 Hz, IH), 6.67 (m, 2H), 6.80 (d, J= 8.5 Hz, I H), 7.27 (m, 4H), 7.40 (m, I H). (Oil).

Example 25: (-)-N-(2-(benzo[d] [I,3]dioxol-5-yloxy)ethyl)-3-(1 -(4-chlorophenyl)-I - (1-methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-I -amine [a]20D -52.5 (c= 1.0, CHCI3), Oil.

Exam pie 26: (+)-N-(2-(benzo(d][1,3]dioxol-5-yioxy)ethyl)-3-(I -(4-ch iorophenyi)-I - (I-methyl-I H-pyrazoi-5-y9ethoxy)-N-methylpropan-1 -amine [cz]20D +51.1 (c= 1.0, CHCI3), Oil.

Example 27: 4-((3,4-dimethoxyphenethyl)(methyl)amino)-1 -(4-chlorophenyl)-1 - (1-methyl-I H-imidazol-2-yl)butan-1 -ol 1H NMR (100 MHz, CDCI3) ö: 1.30-2.80 (m, 13H, (= 2.15, s)), 3.32 (s, 3H), 3.76 (s, 3H), 3.78 (s, 3H), 6.60 (m, 4H), 6.86 (s, 1H), 7.18 (m, 4H). (Oil).

Example 28: 4-((3,4-dimethoxyphenethyl)(methyl)amino)-1 -(4-chlorophenyl)-1 - (2-methyl-2H-1,2,4-triazol-3-yl)butan-1 -01 1H NMR (100 MHz, CDCI3) & 1.30-2.75 (m, 13H, ( = 2.08, s)), 3.59 (s, 3H), 3.72 (s, 3H), 3.75 (s, 3H), 6.57 (m, 3H), 7.18 (m, 4H), 7.66 (s, 1H). (Oil).

Example 29: 4-((3,4-dimethoxyphenethyl)(methyl)amino)-1 -(4-methyl-4H-1,2,4-:. . triazol-3-yl)-1 -phenylbutan-I -ol 1H NMR (100 MHz, Cod3) : 1.30-2.85 (m, 13H, ( = 2.19, s)), 3.65 (s, 3H), 3.79 (s, 3H), 3.83 (s, 3H), 6.66 (m, 3H), 7.25 (m, 5H), 7.74 (s, IH). (Oil). S..

S S U...

Example 30: 4-((3,4-dimethoxyphenethyl)(methyl)amino)-1 -(1 -methyl-I H-imidazol-2-yl)-1 -phenylbutan-I -ol 1H NMR (100 MHz, CDCI3) ö: 1.40-2.85 (m, 13H, (ö = 2.17, s)), 3.31 (s, 3H), 3.75 (s, 3H), 3.78 (S, 3H), 6.60 (m, 4H), 6.88 (s, 1H), 7.20 (m, 5H). (Oil).

Example 31: 4-((3,4-dimethoxyphenethyl)(methyl)amino)-1 -(I -methyl-I H-pyrazol-5-yl)-1 -phenylbutan-1 -01 1H NMR (100 MHz, CDCI3) & 1.30-2.80 (m, 13H, ( = 2.23, s)), 3.59 (s, 3H), 3.80 (s, 3H), 3.82 (s, 3H), 6.20 (m, IH), 6.67 (m, 3H), 7.24 (m, 6H). (Oil).

Example 32: 3-(1 -(4-chlorophenyl)-I -(1 -methyl-I H-pyrazol-5-yl)ethoxy)-N-methyl-N-(2-phenoxyethyl)propan-1 -amine 1H NMR (100 MHz, CDCI3) & 1.69-1.83 (m, 5H, ( = 1.72, s)), 2.30 (s, 3H), 2.57 (m, 2H), 2.77 (m, 2H), 3.02 (m, IH), 3.40 (s, 3H), 3.50 (m, IH), 4.02 (m, 2H), 6.36 (d, 1H), 6.89 (m, 3H), 7.17 (m, 6H), 7.42 (d, IH). (Oil).

Example 33: 3-((4-chlorophenyl)(2-methyl-2H-I,2,4-triazol-3-yl)methoxy)-N-methyl-N(2-phenoxyethyl)propan-1 -amine 1H NMR (100 MHz, CDCI3) & 1.76 (m, 2H), 2.24 (s, 3H), 2.49 (m, 2H), 2.69 (t, J 5.7 Hz, 2H), 3.47 (m, 2H), 3.62 (s, 3H), 3.94 (t, J= 5.7 Hz, 2H), 5.62 (s, IH), 6.81(m, 3H), 7.19 (m, 6H), 7.72 (d, J= 1.3 Hz, IH). (Oil).

Example 34: N-(2-(benzo[d][1,3]dioxol-5-yloxy)ethyl)-3-((4-chlorophenyl)(1 -methyl-I H-pyrazol-5-yl)methoxy)-N-methylpropan-1 -amine *e * * . * 1H NMR (100 MHz, CDCI3) & 1.76 (m, 2H), 2.26 (s, 3H), 2.51 (t, J= 7.1 Hz, 2H), 2.69:...: (t, J= 5.7 Hz, 2H), 3.45 (t, J= 6.1 Hz, 2H), 3.68 (s, 3H), 3.90 (t, J= 5.7 Hz, 2H), 5.35 (s, IH), 5.84 (s, 2H), 5.92 (s, 1H), 6.25 (m, 1H), 6.41 (m, IH), 6.61 (d, J= 8.3 Hz, IH), 7.10-7.40 (m, 5H). (Oil). **.. * * S...

Example 35: N-methyl-4-(1 -methyl-I H-pyrazol-5-yI)-N-phenethyl-4-phenylbutan-* 1-amine 1H NMR (300 MHz, Cod3) & 1.53 (m, 2H), 1.92 (m, 1H), 2.04 (m, IH), 2.30 (s, 3H), 2.46 (m, 2H), 2.62 (m, 2H), 2.78 (m, 2H), 3.57 (s, 3H), 3.85 (m, IH), 6.24 (d, J= 1.9 Hz, 1H), 7.08-7.32 (m, IOH), 7.43 (d, J= 1.9 Hz, IH). (Oil).

Example 36: N-(2-(benzo[d] [1,3]dioxol-5-yloxy)ethyl)-N-methyl-3-((1 -methyl-I H-pyrazol-5-yl)(phenyl)methoxy)propan-1 -amine 1H NMR (300 MHz, CDCI3) ö: 1.83 (m, 2H), 2.32 (s, 3H), 2.56 (t, J= 7.4 Hz, 2H), 2.75 (t, J= 5.9 Hz, 2H), 3.52 (t, J= 6.2 Hz, 2H), 3.75 (s, 3H), 3.96 (t, J= 5.9 Hz, 2H), 5.44 (s, IH), 5.90 (s, 2H), 5.99 (m, IH), 6.29 (dd, J= 8.6 Hz, J'= 2.3 Hz, IH), 6.47 (d, J= 2.3 Hz, 1H), 6.68 (d, J= 8.6 Hz, IH), 7.30-7.37 (m, 6H). (Oil).

Example 37: N-(2-(benzo[d][1,3]dioxol-5-yloxy)ethyl)-3-(cyclopropyl(1 -methyl-I H-pyrazol-5-yl)(phenyl)methoxy)-N-methylpropan-i -amine 1H NMR (300 MHz, CDCI3) 6: 0.03 (m, IH), 0.17 (m, 1H), 0.50 (m, IH), 0.62 (m, IH), 1.89 (m, 3H), 2.42 (s, 3H), 2.70 (m, 2H), 2.87 (t, J= 5.9 Hz, 2H), 3.24 (m, IH), 3.43 (s, 3H), 3.84 (m, 1H), 4.07 (t, J= 5.9 Hz, 2H), 5.96 (s, 2H), 6.39 (dd, J= 8.3 Hz, J' 2.4 Hz, IH), 6.57 (d, J= 2.4 Hz, 1H), 6.68 (d, J= 1.9 Hz, IH), 6.75 (d, J= 8.3 Hz, 1H), 7.16 (m, 2H), 7.29 (m, 3H), 7.53 (d, J= 1,9 Hz, IH). (Oil).

Example 38: N-(2-(benzo(d][I,3]dioxol-5-yloxy)ethyl)-3-(1 -(4-fluorophenyl)-1 -(1-methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-I -amine 1H NMR (300 MHz, CDCI3) 6: 1.74-1.83 (m, 5H, (6 = 1.76, s)), 2.33 (s, 3H), 2.58 (m, 2H), 2.77 (t, J= 5.9 Hz, 2H), 3.06 (m, IH), 3.43 (s, 3H), 3.54 (m, IH), 3.98 (t, J 5.9:, Hz, 2H), 5.90 (s, 2H), 6.30 (m, IH), 6.36 (d, J= 1.9 Hz, IH), 6.48 (d, J 2.4 Hz, IH), 6.68 (d, J= 8.6 Hz, 1H), 6.95 (m, 2H), 7.22 (m, 2H), 7.43 (d, J= 1,9 Hz, IH). (Oil).

Example 39: N-(2-(benzo[d][I,3]dioxol-5-yloxy)ethyl)-3-(1 -(3,4-dichiorophenyl)- 1 -(1 -methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine ** * * S ** 1H NMR (300 MHz, COd3) 6: 1.73-1.83 (m, 5H, (6 = 1.75, s)), 2.32 (s, 3H), 2.57 (m, 2H), 2.76 (t, J= 5.7 Hz, 2H), 3.05 (m, IH), 3.45 (s, 3H), 3.53 (m, IH), 3.98 (t, J= 5.7 Hz, 2H), 5.90 (s, 2H), 6.30 (m, IH), 6.37 (m, IH), 6.48 (m, IH), 6.68 (m, 1H), 7.00 (m, IH), 7.33 (d, J= 8.3 Hz, IH), 7.43 (m, 2H). (Oil).

Example 40: N-(4-fluorophenethyl)-3-(I -(3,4-dichlorophenyl)-I -(I -methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-I -amine 1H NMR (300 MHz, COd3) 6: 1.70-1.82 (m, 5H, (6 = 1.73, s)), 2.28 (s, 3H), 2.43-2.60 (m, 4H), 2.72 (m, 2H), 3.01 (m, IH), 3.42-3.53 (m, 4H, (6 = 3.45, s)), 6.36 (d, J= 1.7 Hz, IH), 6.96 (m, 3H), 7.13 (m, 2H), 7.33 (d, J= 8.3 Hz, IH), 7.44 (m, 2H). (Oil).

Example 41: 3-(1-(4-chlorophenyl)-1-(I-methyl-IH-pyrazol-5-yl)ethoxy)-N-(2-(3, 4-dimethoxyphenoxy)ethyl)-N-methylpropan-1 -amine.

1H NMR (300 MHz, CDCI3) 6: 1.74 (s, 3H), 1.80 (m, 2H), 2.33 (s, 3H), 2.57 (m, 2H), 2.78 (t, J= 5.9 Hz, 2H), 3.04 (m, 1H), 3.42 (s, 3H), 3.54 (m, 1H), 3.81 (s, 6H), 4.00 (t, J= 5.9 Hz, 2H), 6.36 (m, 2H), 6.51 (d, J 3.0 Hz, IH), 6.75 (d, J 8.8 Hz, IH), 7.17 (d, J= 8.8 Hz, 2H), 7.22 (d, J= 8.8 Hz, 2H), 7.41 (d, J= 1.7 Hz, IH). (Oil).

Example 42: N-(2-(benzo[dJ[1,3]dioxol-5-yloxy)ethyl)-3-(1 -(4-chlorophenyl)-1 -(I-methyl-I H-imidazol-2-yl)ethoxy)-N-methylpropan-I -amine 1H NMR (300 MHz, CDCI3) 6: 1.79 (m, 2H), 1.86 (s, 3H), 2.30 (s, 3H), 2.56 (m, 2H), 2.75 (m, 2H), 2.96 (m, 1H), 3.18 (s, 3H), 3.59 (m, IH), 3.95 (m, 2H), 5.87 (s, 2H), 6.28 (m, IH), 6.46 (m, 1H), 6.65 (d, J= 2.3 Hz, IH), 6.78 (d, 1.2 Hz, IH), 6.96 (d, J 1.2 Hz, I H), 7.23 (m, 4H). (Oil).

S

S S

Example 43: N-(2-(benzo[d][I,3]dioxol-5-yloxy)ethyl)-N-methyl-3-(1 -(1 -methyl-I H-imidazol-2-yl)-I -phenylethoxy)propan-1 -amine a SS ** 1H NMR (300 MHz, CDCI3) 6: 1.80 (m, 2H), 1.90 (s, 3H), 2.34 (s, 3H),2.60 (m, 2H), 2.78 (t, J= 5.8 Hz, 2H), 3.00 (m, 1H), 3.19 (s, 3H), 3.62 (m, 1H), 3.99 (t, J= 5.8 Hz, 2H), 5.89 (s, 2H), 6.30 (m, 1H), 6.47 (d, J=2.4 Hz, 1H), 6.67 (d, J= 8.3 Hz, 1H), 6.80 (d, J= 1.2 Hz, IH), 6.99 (d, J= 1.2 Hz, IH), 7.19-7.28 (m, 5H). (Oil).

Example 44: N-(2-(benzo[d][I,3]dioxol-5-yloxy)ethyl)-N-methyl-3-(I -(1-methyl-I H-pyrazol-5-yl)-I -phenylethoxy)propan-I -amine 1H NMR (300 MHz, COd3) 6: 1.76-2.04 (m, 5H, (6 = 1.78, s)), 2.32 (s, 3H), 2.58 (m, 2H), 2.77 (m, 2H), 3.06 (m, IH), 3.43 (s, 3H), 3.54 (m, IH), 3.98 (t, J= 5.8 Hz, 2H), 5.88 (s, 2H), 6.30 (m, IH), 6.36 (d, J= 1.9 Hz, IH), 6.48 (d, J= 2.5 Hz, 1H), 6.67 (d, J= 8.3 Hz, IH), 7.19-7.28 (m, 5H), 7.43 (d, J= 1.9 Hz, IH). (Oil).

Example 45: N-(2-(benzo[d][1,3]dioxol-5-yloxy)ethyl)-3-(1 -(4-methoxyphenyl)-1 - (I-methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan1 -amine 1H NMR (300 MHz, CDCI3) 6: 1.74-1.82 (m, 5H, (6 = 1.75, s)), 2.31 (s, 3H), 2.57 (t, J 7.3 Hz, 2H), 2.75 (t, J= 5.9 Hz, 2H), 3.04 (m, I H), 3.44 (s, 3H), 3.51 (m, 1 H), 3.76 (s, 3H), 3.97 (t, J= 5.9 Hz, 2H), 5.87 (s, 2H), 6.28-6.33 (m, 2H), 6.48 (d, J 2.7 Hz, IH), 6.67 (d, J= 8.6 Hz, IH), 6.79 (m, 2H), 7.13 (m, 2H), 7.41 (d, J 2.0 Hz, IH). (Oil).

Example 46: N-(4-fluorophenethyl)-3-(1 -(4-methoxyphenyl)-I -(1 -methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-I -amine 1H NMR (300 MHz, CDCI3) & 1.70-1.81 (m, 5H, (6 = 1.74, s)), 2.28 (s, 3H), 2.48-2.60 (m, 4H), 2.73 (m, 2H), 3.02 (m, IH), 3.44-3.53 (m, 4H, (6 = 3.45, s)), 3.77 (s, 3H), 6.34 (d, J= 1.8 Hz, IH), 6.81 (d, J= 8.8 Hz, 2H), 6.94 (m, 2H), 7.11-7.26 (m, 4H), 7.42 (d, J 1.8 Hz, IH). (Oil).

Example 47: 3-(I -(4-chlorophenyl)-I -(1 -methyl-I H-pyrazol-5-yl)ethoxy)-N-(2-(4-: fluorophenoxy)ethyl)-N-methylpropan-1 -amine 1H NMR (300 MHz, CDCI3) 6:1.74 (s, 3H), 1.77 (m, 2H), 2.31 (s, 3H), 2.56 (m, 2H), 2.77 (t, J= 5.8 Hz, 2H), 3.03 (m, IH), 3.42 (s, 3H), 3.52 (m, IH), 3.99 (t, J= 5.8 Hz, 2H), 6.35 (d, J= 1.9 Hz, IH), 6.80 (m, 2H), 6.93 (m, 2H), 7.20 (m, 4H), 7.42 (d, J= 1.9 Hz, IH). (Oil).

Example 48: N-(2-(4-fluorophenoxy)ethyl)-3-(1 -(4-methoxyphenyl)-I -(I-methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-I -amine 1H NMR (300 MHz, CDCI3) 6: 1.71-1.83 (m, 5H, (6 = 1.75,s)), 2.33 (s, 3H), 2.58 (t, J= 7.3 Hz, 2H), 2.78 (t, J= 5.9 Hz, 2H), 3.05 (m, IH), 3.45 (s, 3H), 3.51 (m, IH), 3.78 (s, 3H), 4.01 (t, J5.9 Hz, 2H), 6.34 (d, J 1.9 Hz, IH), 6.81 (m, 4H), 6.95 (m, 2H), 7.14 (m, 2H), 7.42 (d, J 1.9 Hz, IH). (Oil).

Example 49: N-(2-(benzo(d][1,3jdioxol-5-yloxy)ethyl)-3-(1 -cyclohexyl-1 -(I -methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 - amine 1H NMR (300 MHz, CDCI3) & 0.84-1.24 (m, 6H), 1.40 (s, 3H), 1.58-1.82 (m, 6H), 2.02 (m, IH), 2.27 (s, 3H), 2.47 (m, 2H), 2.71 (t, J= 5.8 Hz, 2H), 2.94 (m, 1H), 3.30 (m, 1H), 3.94 (t, J= 5.8 Hz, 2H), 3.97 (s, 3H), 5.87 (s, 2H), 6.00 (d, J= 1.9 Hz, 1H), 6.28 (dd, J 8.6 Hz, J'= 2.5 Hz, IH), 6.46 (d, J= 2.5 Hz, IH), 6.65 (d, J= 8.6 Hz, IH), 7.31 (d, J= 1.9 Hz, IH). (Oil).

Example 50: N-(4-chlorophenethyl)-3-(I -(4-chlorophenyl)-1 -(1 -methyl-I H-imidazol-2-yl)ethoxy)-fJ-methylpropan-1 -amine 1H NMR (300 MHz, CDCI3) 6: 1.76 (m, 2H), 1.87 (s, 3H), 2.28 (s, 3H), 2.47-2.60 (m, 4H), 2.73 (m, 2H), 2.97 (m, IH), 3.20 (s, 3H), 3.58 (m, IH), 6.81 (d, J= 1.2 Hz, IH), 6.99 (d, J= 1.2 Hz, IH), 7.09-7.26 (m, 8H). (Oil).

Example 51: N-(4-chlorophenethyl)-3-(1 -(4-chlorophenyl)-1 -(1 -methyl-I H-0 pyrazol-5-yl)ethoxy)-N-methylpropan-I -amine. *. :: 1H NMR (300 MHz, CDCI3) 6: 1.70-1,80 (m, 5H, (8 = 1.73, s)), 2.27 (s, 3H), 2.50 (m, 2H), 2.56 (m, 2H), 2.71 (m, 2H), 3.00 (m, IH), 3.43 (s, 3H), 3.50 (m, IH), 6.36 (d, J= ..: 1,9 Hz, IH), 7.09-7.27 (m, 8H), 7.44 (d, J 1.9 Hz, 1H). (Oil). *4** S...

Example 52: N-(4-methoxyphenethyl)-3-(I -(4-chlorophenyl)-1 -(1 -methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine 1H NMR (300 MHz, CDCI3) 6:1.72-1,82 (m, 5H, (8 = 1.75, s)), 2.29 (s, 3H), 2.46-2.60 (m, 4H), 2.70 (m, 2H), 3.03 (m, IH), 3.44 (s, 3H), 3.52 (m, 1H), 3.78 (s, 3H), 6.36 (d, J= 1.9 Hz, IH), 6.83 (m, 2H), 7.11 (m, 2H), 7.19 (m, 2H), 7.25 (m, 2H), 7.44 (d, J= 1.9 Hz, IH). (Oil).

Example 53: N-(4-fluorophenethyl)-3-(cyclohexyl(1 -methyl-I H-imidazol-2-yl)methoxy)-N-methylpropan-1 -amine 1H NMR (300 MHz, CDCI3) 6: 0.83-1,30 (m, 6H), 1.58-1.90 (m, 6H), 2.15 (m, IH), 2.26 (s, 3H), 2.41 (m, 2H), 2.54 (m, 2H), 2.70 (m, 2H), 3.29 (t, J= 6.3 Hz, 2H), 3.70 (s, 3H), 4.18 (d, J= 9.6 Hz, IH), 6.80 (d, J= 1.2 Hz, 1H), 6.95 (m, 3H), 7.12 (m, 2H).

(Oil).

Example 54: N-methyl-3-((l -methyl-I H-imidazol-2-yl)(phenyl)methoxy)-N-phenethylpropan-I -amine 1H NMR (300 MHz, CDCI3) & 1.84 (m, 2H), 2.30 (s, 3H), 2.50-2.63 (m, 4H), 2.75 (m, 2H), 3.42 (s, 3H), 3.48 (m, IH), 3.59 (m, IH), 5.68 (s, IH), 6.80 (d, J= 1.2 Hz, 1H), 6.97 (d, J= 1.2 Hz, IH), 7.16-7.35 (m, 1OH). (Oil).

Example 55: N-methyl-3-(I -(1 -methyl-I H-imidazol-2-yl)-1 -phenylethoxy)-N-phenethylpropan-1 -amine 1H NMR (300 MHz, CDCI3) & 1.79 (m, 2H), 1.91 (s, 3H), 2.31 (s, 3H), 2.54 (m, 2H), 2.60 (m, 2H), 2. 78 (m, 2H), 3.00 (m, IH), 3.20 (s, 3H), 3.61 (m, IH), 6.80 (d, J= 1.0 Hz, 1H), 7.00 (d, J= 1.0 Hz, 1H), 7.18-7.30 (m, IOH). (Oil).

Example 56: 3-(cyclohexyl(I -methyl-I H-im idazol-2-yl)methoxy)-N-methyl-N-phenethylpropan-I -amine 1H NMR (300 MHz, CDCI3) & 0.83-1.30 (m, 6H), 1.58-1.87 (m, 6H), 2.15 (m, IH), 2.27 (s, 3H), 2.45 (m, 2H), 2.58 (m, 2H), 2.75 (m, 2H), 3.30 (t, J= 6.3 Hz, 2H), 3.69 (s, 3H), 4.18 (d, J= 9.5 Hz, 1H), 6.79 (d, J= 1.2 Hz, IH), 6.92 (d, J= 1.2 Hz, 1H), 7.16- 7.26 (m, 5H). (Oil).

Pharmacological data: The binding of the substituted amine compounds of general formula I to the 5-HI6 receptor was determined as described above.

The binding results for some of these compounds are given in the following

table:

Compound Compound Binding to 5-HT6 according to number receptor [%]

example

6 E-5535 100.6 7 E-5534 96.9 8 E-5555 66 9 E-5556 68.3 E-5568 63.6 *.

11 E-5408 95.0 12 E-5422 91.0 13 E-5423 91.3 E-5522 83.4 16 E-5500 71.7:::;:: 17 E-5521 81.7 18 E-5237 88.0 52 E-5540 66.9

Claims

Claims: Use of a substituted amine compound of general formula I,

wherein m isOorl; n isOorl; R1, R2, R3, R4 and R5, independently of one another, in each case represent a * * * radical selected from the group consisting of hydrogen, -C1-5-alkyl, -C2-5- alkenyl, -O-C1-5-alkyl, -S-C1-5-alkyl, -C(=O)-OH, -C(=O)-C1-5-alkyl, -C1..5-S...

alkylene-C(0)-OH, -C(=O)-O-C1-5-alkyl, -O-C(0)-Ci-5-alkyl, F, Cl, Br, I, -CN, -CE3, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(C1-5-alkyl), -N(C1-5-alkyl)2, -NH(C2-5- alkenyl), -N(C2-5-alkenyl)2, -NO2, -CHO, -CF2H, -CFH2, -C(0)-NH2, -C(=O)- NH(C1-5-alkyl), -C(=O)-N(Ci-5-alkyl)2, -S(0)2-C1-5-alkyl, -S(=O)2-phenyl, - S(=O)2-OH, -NH-C(=O)-C1-5-alkyl, -NH-C(=O)-phenyl, -NH-S(=O)2-phenyl, - NH-S(=O)2-C1-5-alkyl, -S(=O)2-NH-phenyl, -S(=O)2-NH-C1-5-alkyl and -S(=O)2-N(C1-5-alkyl)2; or two radicals selected from the group consisting of R1, R2, R3, R4 and R5 which are located in adjacent positions on the phenyl ring together form a methylendioxy (-O-CH2-O-) group or ethylendioxy group (-O-CH2-C H2-O-); A represents R6 R9 R7 or R1 R8 H R6 represents a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheplyl, cyclopentenyl, cyclohexenyl and phenyl, which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), -C1-5-alkyl, -C2-5-alkenyl, -O-C1-5-alkyl, -S-C1-5-alkyl, -C(0)- OH, -C(=0)-C1-5-alkyl, -C1..5-alkylene-C(=O)-OH, -C(=O)-O-C1-5-alkyl, -0- C(=O)-C1-5-alkyl, F, Cl, Br, I, -CN, -CF3, -OCF3, -SCF3, -OH, -SH, -NH2, - NH(C1-5-alkyl), -N (Ci-5-alkyl)2, -N H(C2-5-alkenyl), -N(C2-5-alkenyl)2, -NO2, - CHO, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-N H(Ci-5-alkyl), -C(=O)-N(C1-5-alkyl)2, -S(=O)2-C1-5-alkyl, -S(=O)2-phenyl, -S(=O)2-OH, -NH-C(=O)-Ci-5-alkyl, : . -NH-C(=O)-phenyl, -NH-S(=O)2-phenyl, -NH-S(=O)2-C1-5-alkyl, -S(=O)2-NH-phenyl, -S(=O)2-NH-C1-5-alkyl and -S(=0)2-N(C1-5-alkyl)2; R7 represents a hydrogen atom; -OH; -O-CH3; -0-C2H5; -O-CH(CH3)2; -0-C(CH3)3; -0-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, :: ::: ethenyl, propenyl, butenyl, pentenyl and hexenyl which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -0-C1-5-alkyl, -S-C1-5-alkyl, F, Cl, Br, I, - CN, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(Ci-5-alkyl), -N(Ci-5-alkyl)2, -NH(C2-5-alkenyl), -N(C2-5-alkenyl)2 and -NO2; or a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl and phenyl, which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), -Ci-5-alkyl, -C2-5-alkenyl, - 0C15alkyl, -S-C1-5-alkyl, -C(=O)-OH, -C(=O)-C1-5-alkyl, -C1.5-alkylene- C(=O)-OH, -C(O)-O-Ci-5-alkyl, -0-C(=O)-C1-5-alkyl, F, Cl, Br, I, -CN, -CF3, - OCF3, -SCF3, -OH, -SH, -NH2, -NH(Ci-5-alkyl), -N(Ci-5-alkyl)2, -NH(C2-5-alkenyl), -N(C2-5-alkenyl)2, -NO2, -CHO, -CF2H, -CFH2, -C(=O)-NH2, -C(=0)-N H(C1 -5-alkyl), -C(=O)-N(Ci-5-alkyl)2, -S(=O)2-C1 -5-alkyl, -S(=O)2-phenyl, - S(=O)2-OH, -NH-C(=O)-C1-5-alkyl, -NH-C(=O)-phenyl, -NH-S(=O)2-phenyl, - NH-S(=O)2-C1-5-alkyl, -S(=O)2-N H-phenyl, -S(=O)2-N H-C1-5-alkyl and -S(=O)2-N(C1 -5-alkyl)2; R8 represents a radical selected from the group consisting of s-NH KH' /C> N')

NH -NH /

NH a-NH

N, NL/ Nb * * * * *1 * * S. Q-' N N N NH NH -lH * S S S.

N N S... * *

I<NNH NN N çLN II_, *.

\ / c_i

H

r_S\ N_N NH HN {-\ , , iLl-1 and

N

wherein any hydrogen atom can be substituted with a substituent selected from the group consisting of -C1-5-alkyl, -C2..5-alkenyl, -O-C1-5-alkyl, -S-C1-5- alkyl, -C(=O)-OH, -C(=O)-Ci-5-alkyl, -C-1..5-alkylene-C(0)-OH, -C(=O)-O-C1-5- alkyl, -O-C(=O)-Cj..5-alkyl, F, CI, Br, I, -CN, -CF3, -OCF3, -SCF3, -OH, -SH, - NH2, -N H(Ci -5-alkyl), -N(Ci-5-alkyl)2, -NH(C2-5-alkenyl), -N(C2-5-alkenyl)2, -NO2, -CHO, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH(C1-5-alkyl), -C(=O)-N(C1..

5-alkyl)2, -S(=O)2-Ci..5-alkyl, -S(0)2-phenyl, -S(=O)2-OH, -NH-C(=O)-Ci-5- alkyl, -NH-C(=O)-phenyl, -NH-S(=O)2-phenyl, -NH-S(=O)2-C1-5-alkyl, -S(=O)2-NH-phenyl, -S(=O)2-N H-C1.. 5-alkyl, -S(=O)2-N(Ci-5-alkyl)2, phenyl, pyrrolyl, pyridinyl, phenoxy and benzyl; whereby said cyclic substituents pyrrolyl, pyridinyl, -S(0)2-phenyl, -N HC(=O)-phenyl, -NH-S(=O)2-phenyl, -S(0)2-NH-phenyl, phenyl, phenoxy and benzyl may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, F, Cl, Br, -CN, -CF3, -OCF3, -SCF3, -OH, -SH, -NH2 and NO2; R9 represents a phenyl radical, which may be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -C1-5-alkyl, -C2-5-alkenyl, -O-Ci-5-alkyl, -S-C1-5-alkyl, -C(=O)-OH, -C(=O)-C1- 5-alkyl, -Ci..5-alkylene-C(=O)-OH, -C(=O)-O-C1-5-alkyl, -O-C(=O)-C1-5-alkyl, F, Cl, Br, I, -CN, -CF3, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(C1-5-alkyl), -N(C1-5- alkyl)2, -NH(C2-5-alkenyl), -N(C2-5-alkenyl)2, -NO2, -CHO, -CF2H, -CFH2, - C(0)-NH2, -C(0)-NH(Ci-5-alkyl), -C(0)-N(Ci-5-alkyl)2, -S(0)2-Ci-5-alkyl, -S(=O)2-phenyl, -S(=O)2-OH, -NH-C(=O)-Ci-5-alkyl, -NH-C(=O)-phenyl, -NH-* : . S(=O)2-phenyl, -NH-S(=O)2-C1-5-alkyl, -S(=O)2-NH-phenyl, -S(=O)2-NH-C1-5-alkyl and -S(=O)2-N(Ci-5-alkyl)2; *::::

S

S and

R' represents a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl and cyclohexenyl, which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), -C1-5-alkyl, -C2-5-alkenyl, -O-Ci-5-alkyl, -S-Ci-5-alkyl, -C(=O)- OH, -C(=O)-Ci-5-alkyl, -C1..5-alkylene-C(=O)-OH, -C(0)-O-Ci-5-alkyl, -0-C(=O)-Ci-5-alkyl, F, Cl, Br, I, -CN, -CE3, -OCF3, -SCF3, -OH, -SH, -NH2, -NH(C1-5-alkyl), -N(C1 -5-alkyl)2, -NH(C2-5-alkenyl), -N(C2-5-alkenyl)2, -NO2, - CHO, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-N H(Ci-5-alkyl), -C(=O)-N(C1-5-alkyl)2, -S(=O)2-C1-5-alkyl, -S(=O)2-phenyl, -S(=O)2-OH, -NH-C(=O)-C1-5-alkyl, -NH-C(=O)-phenyl, -NH-S(=O)2-phenyl, -NH-S(=O)2-Ci-5-alkyl, -S(=O)2-NH-phenyl, -S(=O)2-N H-C1-5-alkyl and -S(=O)2-N(Ci-5-alkyl)2; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof; for the manufacture of a medicament for the prophylaxis and/or treatment of a disorder or disease related to food intake.

2. Use of a substituted amine compound according to claim 1, characterized in that m isOorl; n isOorl; * * * S R1, R2, R3, R4 and R5, independently of one another, in each case represent a **** radical selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, * S*S isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, CF3, -C(0)-NH2, -e. : C(=O)-NH-CH3, -C(=O)-N(CH3)2, -C(=O)-NH-C2H5, -C(=O)-N(C2H5)2, -O-CH3, - O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, -O-C(CH3)3, -C(=O)-OH, -C(=O)-O- CH3, -C(=O)-O-C2H5, -C(=O)-O-CH2--CH2-CH3, -C(=O)-.O-CH(CH3)2, -C(=O)-O- C(CH3)3, F, Cl, Br, I, -CN, -NH2, -NH-CH3, -NH-C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -NH-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; or two radicals selected from the group consisting of R1, R2, R3, R4 and R5 which are located in adjacent positions on the phenyl ring together form a methylendioxy (-O-CH2-O-) group or ethylendioxy group (-O-CH2-CH2-O-); A represents R6 R9 R7 or R1 R8 H R6 represents a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl and phenyl, which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec- butyl, isobutyl, n-pentyl, -CF3, -C(0)-NH2, -C(0)-NH-CH3, -C(O)-N(CH3)2, -C(=O)-NH-C2H5, -C(=O)-N(C2H5)2, -O-CH3, -0-C2H5, -0-CH2-CH2-CH3, -0-CH(CH3)2, -O-C(CH3)3, -C(=0)-OH, -C(=O)-O-CH3, -C(=O)-0-C2H5, -C(=O)-O-CH2-CH2-CH3, -C(=0)-0-CH(CH3)2, -C(=O)-O-C(CH3)3, F, Cl, Br, I, -CN, -NH2, -NH-CH3, -NH-C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -NH-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; R7 represents a hydrogen atom; -OH; -O-CH3; -O-C2H5; -O-CH(CH3)2; -0-C(CH3)3; -O-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, ethenyl, propenyl, butenyl, pentenyl and hexenyl which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -0-CH3, -O-C2H5, -0-CH2-CH2-CH3, -S- CH3, -S-C2H5, -S-CH2-CH2-CH3, F, Cl, Br, I, -CN, -OCF3, -SCF3, -OH, -SH, - NH2, -NH-CH3, -NH-C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -NH-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; or a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl and phenyl, which may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -CF3, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-N(CH3)2, -C(=O)-NH-C2H5, -C(=O)-N(C2H5)2, -O-CH3, -0-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, -0-C(CH3)3, -C(=0)-OH, -C(=O)-0-CH3, -C(=O)-O-C2H5, -C(=0)-O-CH2-CH2-CH3, -C(=O)-O-CH(CH3)2, -C(=O)-O-C(CH3)3, F, Cl, Br, I, -CN, -NH2, -NH-CH3, -NH- C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -NH-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; R8 represents a radical selected from the group consisting of

NH NH /

N

N NN/ C

H * ..

N> CN N N

NH H S * ci a e * 4

N_N (LN 4. a'.

N N

-V 5.4 \ / scsi * p 31 3

S N_N NH

3NH:xi U-s' ft, j-and NJ wherein any hydrogen atom can be substituted with a substituent selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert- butyl, sec-butyl, isobutyl, n-pentyl, -CE3, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)- N(CH3)2, -C(=O)-NH-C2H5, -C(=O)-N(C2H5)2, -O-CH3, -O-C2H5, -O-CH2-CH2- CH3, -O-CH(CH3)2, -O-C(CH3)3, -C(=O)-OH, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-O-CH2-CH2-CH3, -C(=O)--O-CH(CH3)2, -C(=O)-O-C(CH3)3, -C(=O)-CH3, -C(=O)-C2H5, -C(=O)-CH2-CH2-CH3, -C(=O)-CH(CH3)2, -C(=O)-C(CH3)3, F, Cl, Br, I, -CN, -NH2, -NH-CH3, -NH-C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -NH-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; R9 represents a phenyl radical, which may be unsubstituted or substituted with 1, 2, 3, 4 or5 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -CE3, -C(=O)-N H2, -C(=O)-N H-CH3, -C(=O)-N(CH3)2, -C(0)-NH-C2H5, -C(=O)-N(C2H5)2, -O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, -0-C(CH3)3, -C(=O)-OH, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-O-CH2-CH2-CH3, -C(=O)-O-CH(CH3)2, -C(=O)-O-C(CH3)3, -C(=O)-CH3, -C(=O)-C2H5, -C(=O)- CH2-CH2-CH3, -C(=O)-CH(CH3)2, -C(=O)-C(CH3)3, F, Cl, Br, I, -CN, -NH2, -NH- CH3, -NH-C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -NH-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; and -. * * p * ** *.* p R1 represents a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl and cyclohexenyl, which may be unsubstituted or optionally substituted with 1, 2, , : *.

4 or 5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-**l.

butyl, isobutyl, n-pentyl, -CF3, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-N(CH3)2, - C(=O)-NH-C2H5, -C(=O)-N(C2H5)2, -O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -0- CH(CH3)2, -O-C(CH3)3, -C(=O)-OH, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-O- CH2-CH2-CH3, -C(=O)-O-CH (CH3)2, -C(=O)-O-C(CH3)3, -C(=O)-CH3, -C(=O)- C2H5, -C(0)-CH2-CH2-CH3, -C(0)-CH(CH3)2, -C(0)-C(CH3)3, F, Cl, Br, I, - CN, -NH2, -NH-CH3, -NH-C2H5, -NH-CH2-CH2-CH3, -NH-CH(CH3)2, -NH-C(CH3)3, -NH-CH(CH3)(C2H5), -N(CH3)2, -N(C2H5)2 and -NO2; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.

3. Use of a substituted amine compound according to claim I or 2, characterized in that m isOorl; n isOorl; R1, R2, R3, R4 and R5, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, -O-C2H5, -0- CH2-CH2-CH3, -0-C H(CH3), methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Br and I; or two radicals selected from the group consisting of R1, R2, R3, R4 and R5 which are located in adjacent positions on the phenyl ring together form a methylendioxy (-0-CH2-O-) group or ethylendioxy group (-O-CH2-CH2-O-); A represents * * * * * R6 R9 R7 or R1 ; S..'.. S. R8 H

R6 represents an unsubstituted radical selected from the group consisting of cyclopentyl, cyclohexyl and cycloheptyl; or a phenyl radical which may be unsubstituted or substituted with I, 2, 3, 4 or substituent(s) independently selected from the group consisting of -O-CH3, - 0-C2H5, -O-CH2-CH2-CH3, -0-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl and Br; R7 represents a hydrogen atom; -OH; -O-CH3; -O-C2H5; -O-CH(CH3)2; -0-C(CH3)3; -O-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl and sec-butyl; or a phenyl radical which may be unsubstituted or substituted with 1, 2, 3, 4 or substituent(s) independently selected from the group consisting of -O-CH3, - O-C2H5, -0-C H2-CH2-CH3, -0-CH(C H3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl and Br; R8 represents a radical selected from the group consisting of s CH3 CH3 CH3 N' I -N S N) NC) and CH R9 represents phenyl radical which may be unsubstituted or substituted with 1, .* 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl and Br;

S S... and

R1 represents a radical selected from the group consisting of cyclopentyl, cyclohexyl and cycloheptyl; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.

4. Use of a substituted amine compound of general formula Pa according to one or more of claims I to 3, cB A )ma R1 a N R5a) R2 R4 R3 Ia, wherein

 S

ma isOorl; R1a, R2, R3, R4 and R5, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, - O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Br and I; *. S or two radicals selected from the group consisting of R, R2, R3, R4 and R5 which are located in adjacent positions on the phenyl ring together form a methylendioxy (-O-CH2-O-) group or ethylendioxy group (-O-CH2-CH2-O-); R7 represents a hydrogen atom; -OH; -O-CH3; -O-C2H5; -O-CH(CH3)2; -0-C(CH3)3; -O-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl and sec-butyl; or a phenyl radical which may be unsubstituted or substituted with I, 2, 3, 4 or substituent(s) independently selected from the group consisting of -O-CH3, - O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl and Br; and A, B, C, D and E, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, -O-C2H5, -0- CH2-CH2-CH3, -0-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Br and I; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.

5. Use of a substituted amine compound of general formula lb according to one or more of claims I to3, Rib R5b Ib, wherein mb isOorl; R, R2b, R3b, R4b and R5b, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, - O-C2H5, -O-CH2-CH2-CH3, -0-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Br and I; or two radicals selected from the group consisting of R'b, R21', R3b, R41' and R5" which are located in adjacent positions on the phenyl ring together form a methylend loxy (-O-CH2-O-) group or ethylendioxy group (-O-CH2-C H2-O-); and R7b represents a hydrogen atom; -OH; -O-CH3; -O-C2H5; -O-CH(CH3)2; -O-C(CH3)3; -O-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl and sec-butyl; or a phenyl radical which may be unsubstituted or substituted with 1, 2, 3, 4 or substituent(s) independently selected from the group consisting of -O-CH3, - O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl and Br;

I * S * * *5

optionally in form of one of its stereoisomers, preferably enantiomers or * diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof. S... *... * I *

S

6. Use of a substituted amine compound of general formula Ic according to one or more of claims I to 3,

D

ENmc R1c R4C R3C Ic, wherein mc isOorl; R, R2C, R3C, R4C and R5C, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, - O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-bulyl, sec-butyl, isobutyl, F, Cl, Br and I; or two radicals selected from the group consisting of R, R2C, R3C, R4C and R5C which are located in adjacent positions on the phenyl ring together form a methylend ioxy (-0- C H2-O-) group or ethylendioxy group (-O-CH2-C H2-O-); R7C represents a hydrogen atom; -OH; -0-CH3; -0-C2H5; -0-CH(CH3)2; -0-C(CH3)3; -O-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, . :* isopropyl, n-butyl, tert-butyl, isobutyl and sec-butyl; a S or a phenyl radical which may be unsubstituted or substituted with 1, 2, 3, 4 or substituent(s) independently selected from the group consisting of -O-CH3, - O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl and Br; and A, B, C, D and E, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, -O-C2H5, -0- CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Br and I; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.

7. Use of a substituted amine compound of general formula Id according to one or more of claims I to 3, R3d Id, wherein md isOorl; *.. I R, R2d, R3d, Rs* and R5d, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, - O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Br and I; *::::* *0** or two radicals selected from the group consisting of R', R2", R3d, R4d and R5d *.. * : which are located in adjacent positions on the phenyl ring together form a methylendioxy (-O-CH2-O-) group or ethylendioxy group (-O-CH2-CH2-O-); and R7d represents a hydrogen atom; -OH; -O-CH3; -O-C2H5; -O-CH(CH3)2; -O-C(CH3)3; -O-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl and sec-butyl; or a phenyl radical which may be unsubstituted or substituted with 1, 2, 3, 4 or substituent(s) independently selected from the group consisting of -O-CH3, - O-C2H5, -O-CH2-CH2-CH3, -O-CH(C H3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl and Br; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.

8. Use of a substituted amine compound of general formula le according to one or more of claims I to 3,

A

DO\?me Rie R5çf:. . R \ R3 le, *:.*.

wherein I...

me isOorl; R1, R2, R, R4 and R, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, - O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl, Br and I; or two radicals selected from the group consisting of R1, R2, R3, R and R which are located in adjacent positions on the phenyl ring together form a methylend ioxy (-O-CH2-O-) group or ethylendioxy group (-O-CH2-C H2-O-); R7 represents a hydrogen atom; -OH; -O-CH3; -O-C2H5; -O-CH(CH3)2; -0-C(CH3)3; -O-CH2-CH2-CH3; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl and sec-butyl; or a phenyl radical which may be unsubstituted or substituted with 1, 2, 3, 4 or substituent(s) independently selected from the group consisting of -O-CH3, - O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, Cl and Br; and A, B, C, D and E, independently of one another, in each case represent a radical selected from the group consisting of hydrogen, -O-CH3, -O-C2H5, -0- C H-CH-CH3, -0-C H(CH3), methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, F, CI, Br and I; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its ** stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.

9. Use of a substituted amine compound according to one or more of claims I to * 8 selected from the group consisting of * [IJ 2-[4-chlorophenylj-[N-(2-[3,4-dimethoxyphenyl]ethyl) -N-methyl-3-aminopropoxyjmethylj-1-methyl-I H-imidazole, [2] 4-[4-chlorophenyl]-[N-(2-[3,4-d imethoxyphenyl]ethyl)-N-methyl-3-aminopropoxy]methyl]-I-methyl-I H-pyrazole, [3] 2-[ I -[4-chlorophenylj-I -[N-(2-[3,4-d imethoxyphenyl]ethyl)-N-methyl-3-am inopropoxy]ethyl]-1 -methyl-i H-im idazole, [4] 5-[4-chlorophenylj-[N-(2-[3,4-dimethoxyphenyljethyl) -N-methyl-3-aminopropoxyjmethyl]-I -methyl-I H-pyrazole, [5] 5-[ 1 -[4-chlorophenylj-1 -[N-(2-[3,4-d imethoxyphenyl]ethyl)-N-methyl-3-am inopropoxy]ethyl]-l -methyl-I H-pyrazole, [6] N-(2-fluorophenethyl)-3-( I -(4-fluorophenyl)-I -(I-methyl-I H-imidazol-2-yl)ethoxy)-N-methylpropan-1 -amine, [7] 3-( 1 -(4-chlorophenyl)-I -(I-methyl-i H-imidazol-2-yl)ethoxy)-N-(2-fluorophenethyl)-N-methylpropan-1 -amine, [8] N-(4-fluorophenethyl)-N-methyl-3-( I -(I-methyl-I H-imidazol-2-yl)-I -phenylethoxy)propan-1 -amine, [9] 3-( I -cyclohexyl-1 -(1-methyl-I H-imidazol-2-yl)ethoxy)-N-(4-fluorophenethyl)-N-methylpropan-1 -amine,

S * * * * S.

[101 3-( 1 -cyclohexyl-1 -(1-methyl-I H-imidazol-2-yl)ethoxy)-N-methyl-N-p phenethylpropan-I -amine, [11] 3-(1 -(4-fluorophenyl)-I -(I -methyl-I H-pyrazol-5-yl)ethoxy)-N-methyl-N-phenethylpropan-1 -amine, * :: ::* * * , S [12] 3-(I -(4-chlorophenyl)-I -(I -methyl-I H-pyrazol-5-yl)ethoxy)-N-(4-fluorophenethyl)-N-methylpropan-I -amine, [13] N-(4-fluorophenethyl)-3-( I -(4-fluorophenyl)-i -(1-methyl-i H-pyrazol-5-yl)ethoxy)-N-methylpropan-1-amine, [14] 3-( 1 -(4-fluorophenyl)-I -(i-methyl-i H-pyrazol-5-yl)ethoxy)-N-(4-methoxyphenethyl)-N-methylpropan-I -amine, [15] 3-( I -cyclohexyl-1 -(I -methyl-I H-pyrazol-5-yl)ethoxy)-N-(4-methoxyphenethyl)-N-methylpropan-i -amine, [16] N-(2-(4-fluorophenoxy)ethyl)-3-( I -(4-fluorophenyl)-I -(1-methyl-i H-pyrazol-5-yI)ethoxy)-N-methylpropan-1-amine, [17] 3-(i -cyclohexyl-I (1 -methyl-i H-pyrazol-5-yI)ethoxy)-N-(2-(4-fluorophenoxy)ethyl)-N-methylpropan-1 -amine, [18] 4-cyclopropyl-N-methyl-N-phenethyl-4-phenylbutan-1 -amine, [19] N-(2-(benzo[d][ I, 3Jd ioxol-5-yloxy)ethyl)-3-( I -(4-ch lorophenyl)-I -( I -methyl-i H-pyrazol-5-yl)ethoxy)-N-methylpropan-1-amine, [20] N-(3,4-d imethoxyphenethyl)-3-( I -(4-chlorophenyl)-I -(th iophen-2-yI)ethoxy)-N-methylpropan-1 -amine, [211 N-(3,4-dimethoxyphenethyl)-3-((4-chlorophenyl)(2-methyl-2 I-I-i,2,4-S. triazol-3-yI)methoxy)-N-methylpropan-1-amine, [22] N-(3,4-d imethoxyphenethyl)-3-( 1 -(4-chlorophenyl)-I -(2-methyl-2H-1,2,4-* triazol-3-yI)ethoxy)-N-methylpropan-1 -amine, S... S * S...

[23] 3-(1 -(4-chlorophenyl)-1 -(1 -methyl-i H-pyrazol-5-yl)ethoxy)-N-methyl-N-*::: : phenethylpropan-1 -amine, [24] 4-((3,4-dimethoxyphenethyl)(methyl)amino)-I -(4-chlorophenyl)-I -( I -methyl-I H-pyrazol-5-yl)butan-1 -01, [25] (-)-N-(2-(benzo[d][1, 3]d ioxol-5-yloxy)ethyl)-3-( I -(4-chlorophenyl)-1 -( I -methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine, [26] (+)-N-(2-(benzo[d][1,3]d ioxol-5-yloxy)ethyl)-3-( 1 -(4-ch lorophenyl)-1 -(1-methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-i-amine, [27] 4-((3,4d imethoxyphenethyl)(methyl)amino)-1 -(4-chlorophenyl)-I -(I -methyl-I H-imidazol-2-yl)butan-1 -ol, [28] 4-((3,4-dimethoxyphenethyl)(methyl)amino)-I -(4-chlorophenyl)-1 -(2-methyl-2H-1,2,4-triazol-3-yI)butan-1 -01, [29] 4-((3,4-dimethoxyphenethyl)(methyl)amino)-I -(4-methyl-4H-1,2,4-triazol-3-yI)-I -phenylbutan-1 -01, [30] 4-((3,4-d imethoxyphenethyl)(methyl)amino)-I -(1-methyl-I H-im idazol-2-yl)-l -phenylbutan-I -ol, [31] 4-((3,4-d imethoxyphenethyl)(methyl)amino)-I -(1-methyl-I H-pyrazol-5-yI)-I -phenylbutan-I -ol, [32] 3-( 1 -(4-chlorophenyl)-i -(1-methyl-I H-pyrazol-5-yl)ethoxy)-N-methyl-N-(2-phenoxyethyl)propan-1 -amine, *. :

S * *

[33] 3-((4-ch lorophenyl)(2-methyl-2H-1,2,4-triazol-3-yl)methoxy)-N-methyl-N(2-phenoxyethyl)propan-1 -amine, * : . [34] N-(2-(benzo[dJ[i,3]dioxol-5-yloxy)ethyl)-3-((4-chlorophenyl)(1 -methyl*** S...

I H-pyrazol-5-yl)methoxy)-N-methylpropan-I -amine, * : : :: [35] N-methyl-4-( 1-methyl-i H-pyrazol-5-yl)-N-phenethyl-4-phenylbutan-1-amine, [36] N-(2-(benzo[d][i, 3Jd ioxol-5-yloxy)ethyl)-N-methyl-3-(( 1-methyl-I H-pyrazol-5-yl)(phenyl)methoxy)propan-I-amine, [37] N-(2-(benzo[dJ[ 1, 3] d ioxol-5-yloxy)ethyl)-3-(cyclopropyl( I-methyl-I H-pyrazol-5-yl)(phenyl)methoxy)-N-methylpropan-I-amine, [38]N-(2-(benzo[d][I, 3]dioxol-5-yloxy)ethyl)-3-( 1 -(4-fluorophenyl)-I -(I -methyl-I H-pyrazol-5-yI)ethoxy)-N-methylpropan-l -amine, [39] N-(2-(benzo[dJ[ 1, 3]dioxol-5-yloxy)ethyl)-3-( 1 -(3,4-dichlorophenyl)-1 -(1-methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine, [401 N-(4-fluorophenethyl)-3-( 1 -(3,4-d ichlorophenyl)-1 -(1-methyl-I H-pyrazol- 5-yl)ethoxy)-N-methylpropan-1 -amine, [41] 3-( I -(4-chlorophenyl)-I -(1-methyl-i H-pyrazol-5-yl)ethoxy)-N-(2-(3,4-dimethoxyphenoxy)ethyl)-N-methylpropan-1 -amine, [42] N-(2-(benzo[dJ[ 1, 3]dioxol-5-yloxy)ethyl)-3-( I -(4-chlorophenyl)-1 -(1-methyl-I H-imidazol-2-yI)ethoxy)-N-methylpropan-1-amine, [43] N-(2-(benzo[dJ[ I, 3]dioxol-5-yloxy)ethyl)-N-methyl-3-( 1 -(1-methyl-i H-imidazol-2-yl)-I -phenylethoxy)propan-1 -amine, * S S * .* [44] N-(2-(benzo[d][1, 3]d ioxol-5-yloxy)ethyl)-N-methyl-3-( 1 -(I-methyl-I H-* : pyrazol-5-yl)-I -phenylethoxy)propan-I-amine, [45] N-(2-(benzo[d][1,3]dioxol-5-yloxy)ethyl)-3-(I -(4-methoxyphenyl)-1 -(I -: methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine, * I... **** * S S

[46] N-(4-fluorophenethyl)-3-( I -(4-methoxyphenyl)-I -(I-methyl-I H-pyrazol- 5-yl)ethoxy)-N-methylpropan-i -amine, [47] 3-(I -(4-chlorophenyl)-1 -(I -methyl-I H-pyrazol-5-yl)ethoxy)-N-(2-(4-fluorophenoxy)ethyl)-N-methylpropan-1 -amine, [48] N-(2-(4-fluorophenoxy)ethyl)-3-(1 -(4-methoxyphenyl)-1 -(I-methyl-I H-pyrazol-5-yI)ethoxy)-N-methylpropan-l -amine, [49] N-(2-(benzo[d][I, 3]dioxol-5-yloxy)ethyl)-3-( I -cyclohexyl-I -(I-methylI H-pyrazol-5-yl)ethoxy)-N-methylpropan-I -amine, [50] N-(4-chlorophenethyl)-3-( 1 -(4-chlorophenyl)-I -(1-methyl-I H-imidazol-2-yl)ethoxy)-N-methylpropan-1 -amine, [51] N-(4-ch lorophenethyl)-3-( I -(4-ch lorophenyl)-I -(1-methyl-i H-pyrazol-5-yl)ethoxy)-N-methylpropan-1 -amine, [52] N-(4-methoxyphenethyl)-3-( I -(4-ch lorophenyl)-1 -(I-methyl-I H-pyrazol-5-yl)ethoxy)-N-methylpropan-1-amine, [531 N-(4-fluorophenethyl)-3-(cyclohexyl( 1-methyl-I H-imidazol-2-yl)methoxy)-N-methylpropan-1 -amine, [54] N-methyl-3-(( 1-methyl-I H-im idazol-2-yl)(phenyl)methoxy)-N-phenethylpropan-1 -amine, * ki * * *S [55] N-methyl-3-(1 -(I -methyl-I H-imidazol-2-yl)-1 -phenylethoxy)-N-phenethylpropan-1 -amine and [56] 3-(cyclohexyl(1 -methyl-i H-imidazol-2-yI)methoxy)-N-methyl-N-: phenethylpropan-1 -amine; * a, a.' * a.. * a.

optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.

10. Use of at least one substituted amine compound of general formula I according to one or more of claims I to 9 for the manufacture of a medicament for the regulation of appetite; for the maintenance, increase or reduction of body weight; or for the prophylaxis and/or treatment of obesity, bulimia, anorexia, cachexia or type II diabetes (non insulin dependent diabetes mellitus), more preferably for the prophylaxis and/or treatment of obesity.

11. Use of at least one substituted amine compound of general formula I according to one or more of claims I to 9 for the manufacture of a medicament for the prophylaxis and/or treatment of stroke; seizures; migraine; head trauma; epilepsy; irritable colon syndrome; irritable bowel syndrome; disorders of the central nervous system; depression; bipolar disorders; obsessive compulsory disorder; sleep disorders; psychosis; neurodegenerative disorders, preferably selected from the group consisting of Morbus Alzheimer, Morbus Parkinson, Morbus Huntington and Multiple Sclerosis; schizophrenia; chronic intermittent hypoxia; convulsions; or hyperactivity disorder (ADHD, attention deficitlhyperactivity disorder).

S * p *5 I,. S

S S * * S S

5i I * * * SI

S