The present invention relates to nitro-substituted phenyl-piperazine compounds of general formula I,

a process for their preparation, medicaments comprising said nitro-substituted phenyl-piperazine compounds as well as the use of said nitro-substituted phenyl- piperazine compounds for the preparation of medicaments, which are particularly suitable for the prophylaxis and/or treatment of disorders or diseases that are at least partially mediated via 5-HT ₆ receptors.

The superfamily of serotonin receptors (5-HT) includes 7 classes (5-HT ₁ -S-HT ₇ ) encompassing 14 human subclasses [D. Hoyer, et al., Neuropharmacology, 1997, 36, 419]. The 5-HTβ receptor is the latest serotonin receptor identified by molecular cloning both in rats [FJ. Monsma et al., MoI. 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].

Compounds with 5-HT ₆ receptor affinity are useful for the treatment of various disorders of the Central Nervous System and of the gastrointestinal tract, such as irritable intestine syndrome. Compounds with 5-HT ₆ receptor affinity are also useful in the treatment of anxiety, depression and cognitive memory disorders [M. Yoshioka et al., Ann. NY Acad. Sci., 1998, 861 , 244; A. Bourson et al., Br. J. Pharmacol. , 1998, 125, 1562; D.C. Rogers et al., Br. J. Pharmacol. Suppl., 1999, 127, 22P; A. Bourson

et al., J. Pharmacol. Exp. Ther. , 1995, 274, 173; AJ. Sleight, et al., Behav. Brain Res. , 1996, 73, 245; T.A. Branchek et al., Annu. Rev. Pharmacol. Toxicol. , 2000, 40, 319; C. Routledge et al., Br. J. Pharmacol. , 2000, 130, 1606]. It has been shown that typical and atypical antipsychotic drugs for treating schizophrenia have a high affinity for 5-HT ₆ receptors [B.L. Roth et al., J. Pharmacol. Exp. Ther. , 1994, 268, 1403; CE. Glatt et al., MoI. Med. , 1995, 1 , 398; F.J. Mosma,et al., MoI. Pharmacol. , 1993, 43, 320; T. Shinkai et al., Am. J. Med. Genet. , 1999, 88, 120]. Compounds with 5-HT ₆ receptor affinity are useful for treating infant hyperkinesia (ADHD, attention deficit / hyperactivity disorder) [W. D. Hirst et al., Br. J. Pharmacol. , 2000, 130, 1597; C. Gerard et al., Brain Research , 1997, 746, 207; M. R. Pranzatelli, Drugs of Today , 1997, 33, 379].

Recently, it has been shown that the 5-HT ₆ receptor also plays a role in food ingestion [Neuropharmacology, 41 , 2001 , 210-219].

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 are particularly suitable as active ingredients in medicaments, especially in medicaments for the prophylaxis and/or treatment of disorders or diseases related to 5-HT ₆ receptors such as food intake related disorders.

Surprisingly, it has been found that the nitro-substituted phenyl-piperazine compounds of general formula I, Ia and Ib given below show good to excellent affinity for 5-HT ₆ -receptors. These compounds are therefore particularly suitable as pharmacologically active agents in a medicament for the prophylaxis and/or treatment of disorders or diseases related to 5-HT ₆ -receptors such as food intake related disorders like obesity.

Thus, in one aspect the present invention relates to nitro-substituted phenyl piperazine compounds of general formula I,

wherein

X represents a -NR J1 D R2 moiety or a -OR moiety;

R ¹ represents a saturated or unsaturated 3- to 9-membered cycloaliphatic radical, which may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of oxo (=O), thioxo (=S), Ci _-5 -alkyl, -O-Ci _-5 -alkyl, -S- Ci- ₅ -alkyl, -C(=O)-OH, -C(=O)-C _1-5 -alkyl, -C(=O)-O-C _1-5 -alkyl, -O-C(=O)-C _1-5 - alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH ₁ -SH, -NH ₂ , -NH(C _1-5 -alkyl), - N(Ci _-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ , -S(=O) ₂ -Ci _-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl and which may contain 1 , 2 or 3 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulfur as ring member(s) and which is bonded via a linear or branched Ci. ₆ alkylene, C _2-6 alkenylene or C _2-6 alkinylene group which may be unsubstituted or substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, I, - CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -O-Ci- ₅ -alkyl, -S-Ci _-5 -alkyl, -NH-(C _1- 5-alkyl) and -N(Ci _-5 -alkyl) ₂ ;

a heteroaryl radical selected from the group consisting of furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl which may be substituted with 1 , 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of d-s-alkyl, -O-Ci _-5 -alkyl, -S-C _1-5 -alkyl, -C(=O)-OH, -C(=O)-Ci _-5 -alkyl, -C(=O)-O- Ci _-5 -alkyl, -O-C(=O)-Ci _-5 -alkyl, F, Cl, Br, I, -CN ₁ -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(C _1-5 -alkyl), -N(C _1-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(Ci _-5 -alkyl), -C(=O)-N(Ci _-5 -alkyl) ₂ , -S(=O) ₂ -Ci _-5 -alkyl, -S(=O) ₂ - phenyl, phenyl, phenoxy and benzyl;

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ )-group and may be substituted with 1 , 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of Ci _-5 -alkyl, -O-C _1-5 -alkyl, -S-Ci _-5 -alkyl, -C(=O)-Ci _-5 -alkyl, - C(=O)-O-C _1-5 -alkyl, -O-C(=O)-Ci _-5 -alkyl, F, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , - OH, -SH, -NH ₂ , -NH(Ci _-5 -alkyl), -N(C _1-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , - C(=O)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(C^ _s -a\kyl) ₂ , -S(=O) ₂ -Ci _-5 -alkyl, - S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

an aryl or heteroaryl radical selected from the group consisting of naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ ) ₂ -group and/or may be substituted with 1 , 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of C _1-5 -alkyl, -O-C _1-5 -alkyl, -S-C _1-5 -alkyl, -C(=O)-OH, -C(=O)- Ci- ₅ -alkyl, -C(=O)-O-Ci _-5 -alkyl, -O-C(=O)-C _1-5 -alkyl, F, Cl, Br, I, -CN, -CF ₃ , -

OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(C _1-5 -alkyl), -N(C _1-5 -alkyl) ₂ , -NO ₂ , -CHO, - CF ₂ H, -CFH ₂ , -C(=O)-NH ₂₎ -C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ 2, - S(=O) ₂ -Ci _-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1- b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ ) ₃ - group and/or may be substituted with 1 , 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of Ci _-5 -alkyl, -O-Ci _-5 -alkyl, - S-C-ι- ₅ -alkyl, -C(=O)-OH, -C(=O)-C _1-5 -alkyl, -C(=O)-O-C _1-5 -alkyl, -0-C(^O)-C _{1 -5} - alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(C _1-5 -alkyl), - N(C _1-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(Ci _-5 -alkyl) ₂ , -S(=O) ₂ -Ci _-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

or

a -C(=O)-R ^η ^ moiety;

R ² represents a hydrogen atom or a linear or branched, saturated or unsaturated Ci-io aliphatic radical which may be unsubstituted or substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, I, ^â–  CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -O-Ci _-5 -alkyl, -S-Ci _-5 -alkyl, -NH-(C _1- 5-alkyl) and -N(Ci _-5 -alkyl) ₂ ; or

R ¹ and R ² together with the bridging nitrogen a saturated or unsaturated, but not aromatic 3- to 6-membered heterocyclic ring which contains 1 , 2 or 3 additional heteroatom(s) independently selected from the group consisting of nitrogen and sulfur as ring member(s) and which may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of Ci _-5 - alkyl, -O-C _1-5 -alkyl, -S-Ci _-5 -alkyl, oxo (=0), thioxo (=S), -C(=O)-OH, -CC=O)-C _1-

₅ -alkyl, -C(=O)-O-Ci _-5 -alkyl, -O-C(=O)-C _1-5 -alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(C _1-5 -alkyl), -N(C _1-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, - CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ , -S(=O) ₂ -C _1-5 - alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

R ³ represents a 5- to 10-membered aryl or heteroaryl radical, which may be unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of Ci-5-alkyl, -O-Ci _-5 -alkyl, - S-d-s-alkyl, -C(=O)-OH, -C(=O)-Ci _-5 -alkyl, -C(=O)-O-C _1-5 -alkyl, -O-C(=O)-C _1-5 - alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(C _1-5 -alkyl), - N(Ci _-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(Ci- ₅ -alkyl) ₂ , -S(=O) ₂ -Ci _-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl and which may be bonded via a linear or branched Ci- ₆ alkylene, C _2-6 alkenylene or C _2-6 alkinylene group which may be unsubstituted or substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -O-Ci _-5 -alkyl, -S-C _1-5 - alkyl, -NH-(Ci- ₅ -alkyl) and -N(Ci- ₅ -alkyl) ₂ and whereby the heteroaryl radical contains 1 , 2 or 3 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulfur as ring member(s);

R ⁴ , R ⁵ and R ⁶ each represent a hydrogen atom;

R ⁷ and R ⁸ , identical or different, each represent a hydrogen atom or a linear or branched, saturated or unsaturated Ci_i ₀ aliphatic radical which may be unsubstituted or substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , - OH, -SH, -NH ₂ , -O-d- ₅ -alkyl, -S-C _1-5 -alkyl, -NH-(C _1-5 -alkyl) and -N(C _1-5 -alkyl) ₂ ;

R ⁹ and R ¹⁰ , identical or different, each represent a hydrogen atom or a linear or branched, saturated or unsaturated Ci-i ₀ aliphatic radical which may be unsubstituted or substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , - OH, -SH, -NH ₂ , -O-Ci _-5 -alkyl, -S-C _1-5 -alkyl, -NH-(C _1-5 -alkyl) and -N(C _1-5 -alkyl) ₂ ;

R ¹¹ represents a linear or branched, saturated or unsaturated, unsubstituted C-M _O aliphatic radical or a 5- to 10-membered aryl or heteroaryl radical which may be unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of Ci-5-alkyl, -O-Ci _-5 -alkyl, - S-d-5-alkyl, -C(=O)-OH, -C(=O)-C _1-5 -alkyl, -C(=O)-O-Ci _-5 -alkyl, -O-C(=O)-Ci _-5 - alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(Ci _-5 -alkyl), - N(C _1-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(d _-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ , -S(=O) ₂ -Ci _-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl and whereby the heteroaryl radical contains 1 , 2 or 3 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulfur as ring member(s);

and

R ¹² represents an aryl radical which may be substituted with 1 , 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of Ci _-5 -alkyl, - O-Ci-s-alkyl, -S-Ci _-5 -alkyl, -C(=O)-OH, -C(=O)-C _1-5 -alkyl,-C(=O)-O-C _1-5 -alkyl, - O-C(=O)-C _1-5 -alkyl, F, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -SH ₁ -NH ₂ , -NH(C _1-5 - alkyl), -N(C _1-5 -alkyl) ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(C _1-5 - alkyl), -C(=O)-N(Ci _-5 -alkyl) ₂ , -S(=O) ₂ -C _1-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

a heteroaryl radical selected from the group consisting of furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl which may be unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of Ci _-5 -alkyl, -O-C _1-5 -alkyl, -S-C _1-5 -alkyl, -C(=O)-OH, -C(=O)-C _1-5 -alkyl, -C(=O)-O-C _1-5 -alkyl, -O-C(=O)-C _1-5 -alkyl, F, Cl, Br, I, -CN, - CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(Ci _-5 -alkyl), -N(C _1-5 -alkyl) ₂ , -NO ₂ , - CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(Ci _-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ , -S(=O) ₂ -Ci- ₅ -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

or

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, which may be unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of Ci _-5 -alkyl, -O-Ci _-5 -alkyl, - S-C _1-5 -alkyl, -C(=O)-OH, -C(=O)-C _1-5 -alkyl, -C(=O)-O-C _1-5 -alkyl, -O-C(=O)-C _1-5 - alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(C _1-5 -alkyl), - N(C _1-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(d _-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ , -S(=O) ₂ -Ci _-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl and which is bonded via a -(CH ₂ )i _{( 2 o} r3- group;

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

Preferably the compound Benzyl-[5-(4-methyl-piperazin-1-yl)-2-nitro-phenyl]-amine may be excluded in any of the definitions given herein.

Preferred are compounds of general formula I given above, wherein R ¹ represents

an (hetero)cycloaliphatic radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, cycloheptenyl, cyclooctyl, cyclooctenyl, cyclononyl, imidazolidinyl, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl and azepanyl whereby said (hetero)cylcoaliphatic radical can be bonded via a -(CH ₂ ) _{I1 2 o} r ₃ - group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of oxo (=O), thioxo (=S), methyl, ethyl, n-propyl, isopropyl, n-butyl, tert- butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ ,

-0-C(CHs) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S-C(CHg) ₃ , -C(=O)- OH, -C(=O)-O-CH ₃ , -C(SO)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , - C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)- CH(CHa) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN ₁ -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , - NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CHs) ₂ , -NH-C(CH ₃ ) ₃ , -N(CH ₃ J ₂ , - N(C ₂ Hs) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH- C ₂ H ₅ , -C(=O)-N(CHs) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ,

a heteroaryl radical selected from the group consisting of furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said heteroaryl radical may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , - 0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S- CH(CHs) ₂ , -S-C(CHg) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ - CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , - C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , - OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH- CH(CHs) ₂ , -NH-C(CHa) ₃ , -N(CH ₃ ) ₂ , -N(C ₂ Hg) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)- NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and - S(=O) ₂ -CH _3l

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a - (CH ₂ )-group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert- butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CHs) ₂ , -S-C(CHs) ₃ , -C(=O)-O- CH ₃ , -C(=O)-O-C ₂ Hs, -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-

C(CHg) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , - C(=O)-C(CH ₃ ) ₃ , F, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH- C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CH ₃ ) ₃ , -N(CH ₃ ) _2l -N(C ₂ Hg) ₂ , -NO ₂ , - CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)- N(CHg) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ,

an aryl or heteroaryl radical selected from the group consisting of naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ ) ₂ -group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , - O-CH(CH ₃ ) _2l -O-C(CH ₃ ) _3> -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S- C(CH ₃ ) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃₎ -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , - C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ - CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, - SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CHg) ₂ , -NH-C(CH ₃ ) ₃ , - N(CHa) ₂ , -N(C ₂ Hs) ₂ , -NO ₂ , -CHO ₁ -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , - C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ,

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ ) ₃ -group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , - 0-CH(CHs) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CHs) ₂ , -S- C(CHa) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , - C(=O)-O-CH(CHs) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ - CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -

SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CH ₃ ) ₃ , - N(CH ₃ ) ₂ , -N(C ₂ Hs) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , - C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ,

or

a -C(=O)-R ¹² moiety;

preferably R ¹ represents

an unsubstituted pyrrolyl radical;

an aryl or heteroaryl radical selected from the group consisting of phenyl and pyrrolyl, whereby said phenyl radical is bonded via a -(CH ₂ )-group and said pyrrolyl radical is bonded via a -(CH ₂ ) ₂ -group and/or said phenyl or pyrrolyl radical may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -O- CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ - CH ₂ -CH ₃ , -S-CH(CHa) ₂ , -S-C(CH ₃ ) ₃ , -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ - CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , - C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Br, I, -CN, -CF ₃ , -OCF ₃ , - SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH- C(CHg) ₃ , -N(CH ₃ ) ₂ , -N(C ₂ Hg) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH- CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N (CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ or

a -C(=O)-R ¹² moiety;

more preferably R ¹ represents an unsubstituted pyrrolyl radical;

an aryl or heteroaryl radical selected from the group consisting of phenyl and pyrrolyl, whereby said phenyl radical is bonded via a -(CH ₂ )-group and said pyrrolyl radical is bonded via a -(CH ₂ ) ₂ -group and/or said phenyl or pyrrolyl radical may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, F, Br

and I or

a -C(=O)-R ¹² moiety;

and X and R ² to R ¹² have the above defined meaning, 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.

Furthermore such nitro-substituted phenyl-piperazine compounds of general formula are preferred, wherein

R ² represents a hydrogen atom or a linear or branched, unsubstituted Ci-i _O alkyl radical;

preferably R ² represents a hydrogen atom or an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert- butyl;

more preferably R ² represents a hydrogen atom or a methyl radical;

and X, R ¹ and R ³ to R ¹² have the above defined meaning, 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.

Also preferred are such nitro-substituted phenyl-piperazine compounds of general formula I, wherein

R ¹ and R ² together with the bridging nitrogen atom form a moiety selected from the group consisting of

whereby each of these afore mentioned cyclic moieties may be substituted in any position including the -NH-groups with 1 , 2 or 3 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, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , - O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃₎ -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S- C(CHa) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , - C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ - CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, - SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CH ₃ ) ₃ , - N(CH ₃ ) ₂ , -N(C ₂ Hg) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , - C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) _2l -S(=O) ₂ -CH ₃ , -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

preferably R ¹ and R ² together with the bridging nitrogen atom form a pyridazin-3-one moiety which may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, -O- CH ₃ , -0-C ₂ H ₅ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅₎ -C(=O)-CH ₃ , -C(=O)- C ₂ H ₅ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , - NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , phenyl, phenoxy and benzyl;

more preferably R ¹ and R ² together with the bridging nitrogen atom form an unsubstituted pyridazin-3-one moiety;

and X and R ³ to R ¹² have the above defined meaning, 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.

Moreover, such nitro-substituted phenyl-piperazine compounds of general formula I given above are preferred, wherein

R ³ represents an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, fury! (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical may be bonded via a -(CH ₂ )i, 2 _o r3-group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -0-C(CHg) ₃ , -S-CH ₃ , -S- C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CHs) ₂ , -S-C(CH ₃ ) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , - C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂₎ -C(=O)-O-C(CH ₃ ) ₃ , - C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ - CH ₂ -CH ₃ , -NH-CH(CHs) ₂ , -NH-C(CH ₃ ) ₃ , -N(CH ₃ ) ₂₎ -N(C ₂ H ₅ ) ₂ , -NO ₂ , -CHO, -CF ₂ H, - CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)- N(C ₂ Hs) ₂ and -S(=O) ₂ -CH ₃ ;

preferably R ³ represents a phenyl radical which may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n- propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , - 0-CH ₂ -CH ₂ -CH ₃ , -0-CH(CHs) ₂ , -O-C(CH ₃ ) ₃ , -S-CH3, -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S- CH(CHs) ₂ , -S-C(CHs) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ - CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , - C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , - OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH- CH(CHs) ₂ , -NH-C(CHs) ₃ , -N(CHs) ₂ , -N(C ₂ Hg) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)- NH ₂ , -C(=O)-NH-CHs, -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and - S(=O) ₂ -CH ₃ ;

more preferably R ³ represents an unsubstituted phenyl radical;

and X, R ¹ , R ² and R ⁴ to R ¹² have the above defined meaning, 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.

Also preferred are nitro-substituted phenyl-piperazine compounds of general formula I, wherein

R ⁷ and R ⁸ , identical or different, each represent a hydrogen atom or a linear or branched, unsubstituted Ci-i _O alkyl radical;

preferably R ⁷ and R ⁸ , identical or different, each represent a hydrogen atom or an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl;

more preferably R ⁷ and R ⁸ each represent a hydrogen atom;

and X, R ¹ to R ⁶ and R ⁹ to R ¹² have the above defined meaning, 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.

Also preferred are nitro-substituted phenyl-piperazine compounds of general formula I, wherein R ⁹ and R ¹⁰ , identical or different, each represent a hydrogen atom or a linear or branched, unsubstituted CM ₀ alkyl radical;

preferably R ⁹ and R ¹⁰ , identical or different, each represent a hydrogen atom or an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl;

more preferably R ⁹ and R ¹⁰ each represent a hydrogen atom;

and X, R ¹ to R ⁸ and R ¹¹ and R ¹² have the above defined meaning, 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.

Also preferred are nitro-substituted phenyl-piperazine compounds of general formula I, wherein

R ¹¹ represents an alkyl radical selected from the group consisting of methyl, ethyl, n- propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl; or an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazoiyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, pyrimidinyl, pyridinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , - 0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S- CH(CHs) ₂ , -S-C(CHg) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ - CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅₍ - C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃₎ F, Cl, Br, I, -CN, -CF ₃ , - OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH- CH(CHa) ₂ , -NH-C(CH ₃ ) _S , -N(CH ₃ ) ₂ , -N(C ₂ H ₅ ) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)- NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and - S(=O) ₂ -CH ₃ ;

preferably R ¹¹ represents an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl and n-butyl; or an aryl or heteroaryl radical selected from the group consisting of phenyl and pyridinyl whereby said aryl or heteroaryl may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, -0-CH ₃ , -0-C ₂ H ₅ , - C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , F ₁ Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , - OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-

C(CHs) ₃ , -N(CHg) ₂ , -N(C ₂ Hg) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH- CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ;

more preferably R ¹¹ represents an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl and n-butyl; or an unsubstituted phenyl or pyridinyl radical;

and X, R ¹ to R ¹⁰ and R ¹² have the above defined meaning, 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.

Also preferred are nitro-substituted phenyl-piperazine compounds of general formula I, wherein

R ¹² represents an aryl radical which may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -O-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , - O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH3, -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂₎ -S- C(CHa) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , - C(=O)-O-CH(CH ₃ ) _2> -C(=O)-O-C(CH ₃ ) ₃₎ -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ - CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -SH, - NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CH ₃ ) ₃ , - N(CHs) ₂ , -N(C ₂ Hs) ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH- C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ Hs) ₂ and -S(=O) ₂ -CH ₃ ;

a heteroaryl radical selected from the group consisting of furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl whereby said heteroaryl radical may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , - 0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH3, -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-

CH(CHa) ₂ , -S-C(CHs) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ - CH ₂ -CH ₃ , -C(^O)-O-CH(CHs) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅₎ - C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , - OCF ₃ , -SCF ₃ , -OH ₁ -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH- CH(CH ₃ ) ₂ , -NH-C(CHg) ₃ , -N(CH ₃ ) ₂ , -N(C ₂ H ₅ ) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)- NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and - S(=O) ₂ -CH ₃ ;

or

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1 -b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ )i. _{2 o} r ₃ - group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n- propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -O-CH ₃ , -0-C ₂ H ₅ , - 0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S- CH(CHa) ₂ , -S-C(CH ₃ ) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H _5l -C(=O)-O-CH ₂ - CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂₎ -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH _3> -C(=O)-C ₂ H ₅ , - C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃₎ F, Cl, Br, I, -CN, -CF ₃ , - OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH- CH(CH ₃ ) ₂ , -NH-C(CHa) ₃ , -N(CH ₃ ) ₂ , -N(C ₂ H ₅ ) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)- NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and - S(=O) ₂ -CH ₃ ;

preferably R ¹² represents a phenyl radical which may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n- propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , - 0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂₎ -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S- CH(CH ₃ ) ₂ , -S-C(CH ₃ )S, -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ - CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , - C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Br, I, -CN, -CF ₃ , -OCF ₃ , -

SCF ₃ , -SH ₁ -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) _2> -NH- C(CHs) ₃ , -N(CH ₃ ) ₂ , -N(C ₂ Hg) ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , - C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) _2l -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ;

more preferably R ¹² represents an unsubstituted phenyl radical;

and X and R ¹ to R ¹¹ have the above defined meaning, 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.

Also preferred are nitro-substituted phenyl-piperazine compounds of general formula I, wherein

R ¹ represents an unsubstituted pyrrolyl radical; an aryl or heteroaryl radical selected from the group consisting of phenyl and pyrrolyl, whereby said phenyl radical is bonded via a -(CH ₂ )-group and said pyrrolyl radical is bonded via a -(CH ₂ ) ₂ -group and/or said phenyl or pyrrolyl radical may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , - O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S- C(CHs) ₃ , -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , -C(=O)-O- CH(CHs) ₂ , -C(=O)-O-C(CH ₃ )s, -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ -CH ₃ , - C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Br, I ₁ -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CH ₃ ) _3l -N(CH ₃ ) _2l - N(C ₂ Hg) ₂ , -NO ₂ , -CHO, -CF ₂ H ₁ -CFH ₂ , -C(=O)-NH _2l -C(=O)-NH-CH ₃ , -C(=O)-NH- C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ )s and -S(=O) ₂ -CH ₃ or a -C(=O)-R ¹² moiety;

R ² represents a hydrogen atom or an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl;

or

R ¹ and R ² together with the bridging nitrogen atom form a pyridazin-3-one moiety which may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, -0-CH ₃ , - 0-C ₂ H ₅ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , phenyl, phenoxy and benzyl;

R ³ represents a phenyl radical which may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , - O-CH(CH ₃ ) ₂₎ -O-C(CH ₃ ) ₃ , -S-CH3, -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S- C(CH ₃ ) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , - C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ - CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, - SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CHg) ₂ , -NH-C(CHs) ₃ , - N(CH ₃ ) ₂ , -N(C ₂ Hs) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , - C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ;

R ⁴ , R ⁵ and R ⁶ each represent a hydrogen atom;

R ⁷ and R ⁸ , identical or different, each represent a hydrogen atom or an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec- butyl, isobutyl and tert-butyl;

R ⁹ and R ¹⁰ , identical or different, each represent a hydrogen atom or an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec- butyl, isobutyl and tert-butyl;

R ¹¹ represents an alkyl radical selected from the group consisting of methyl, ethyl, n- propyl, isopropyl and n-butyl; or an aryl or heteroaryl radical selected from the group consisting of phenyl and pyridinyl whereby said aryl or heteroaryl may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, -0-CH ₃ , -0-C ₂ H ₅ , -C(=O)-OH, - C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ ,

-NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CH ₃ ) ₃ , -N(CH ₃ J ₂ , - N(C ₂ Hs) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH _3j -C(=O)-NH- C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ;

and

R ¹² represents a phenyl radical which may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -O-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , - 0-CH(CHs) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CHg) ₂ , -S- C(CHs) ₃ , -CO=O)-OH, -C(=O)-O-CHs, -CO=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , - C(=O)-O-CH(CHs) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -CO=O)-CH ₂ -CH ₂ - CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CHs)s, F, Br, I ₁ -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -SH, - NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CHs) ₃ , - N(CHs) ₂ , -N(C ₂ Hg) ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -CO=O)-NH-CH ₃ , -C(=O)-NH- C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ .

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 are nitro-substituted phenyl-piperazine compounds of general formula I, wherein

R ¹ represents an unsubstituted pyrrolyl radical; an aryl or heteroaryl radical selected from the group consisting of phenyl and pyrrolyl, whereby said phenyl radical is bonded via a -(CH ₂ )-group and said pyrrolyl radical is bonded via a -(CH ₂ ) ₂ -group and/or said phenyl or pyrrolyl radical may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, F, Br and I or a -C(=O)-R ¹² moiety;

R ² represents a hydrogen atom or a methyl radical;

or

R ¹ and R ² together with the bridging nitrogen atom form an unsubstituted pyridazin-3- one moiety;

R ³ represents an unsubstituted phenyl radical;

R ⁴ , R ⁵ and R ⁶ each represent a hydrogen atom;

R ⁷ and R ⁸ each represent a hydrogen atom;

R ⁹ and R ¹⁰ each represent a hydrogen atom;

R ¹¹ represents an alkyl radical selected from the group consisting of methyl, ethyl, n- propyl and n-butyl; or an unsubstituted phenyl or pyridinyl radical

and

R ¹² represents an unsubstituted phenyl radical;

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 are nitro-substituted phenyl-piperazine compounds selected from the group consisting of

[1 ] [5-(4-Methyl-piperazin-1 -yl)-2-nitro-phenyl]-(2-pyrrol-1 -yl-ethyl)-amine,

[2] (4-Fluoro-benzyl)-[5-(4-methyl-piperazin-1-yl)-2-nitro-pheny l]-amine,

[3] N-[5-(4-Methyl-piperazin-1 -yl)-2-nitro-phenyl]-benzamide,

[4] N-Mθthyl-N-[5-(4-methyl-pipθrazin-1-yl)-2-nitro-phenyl]-be nzamide,

[5] [5-(4-Methyl-piperazin-1 -yl)-2-nitro-phenyl]-pyrrol-1 -yl-amine,

[6] 2-[5-(4-Methyl-piperazin-1-yl)-2-nitro-phenyl]-2H-pyridazin- 3-one,

[7] 1 -Methyl-4-(4-nitro-3-phenoxy-phenyl)-piperazine,

[8] Benzyl-[5-(4-butyl-piperazin-1 -yl)-2-nitro-phenyl]-amine,

[9] Benzyl-[2-nitro-5-(4-pyridin-2-yl-piperazin-1 -yl)-phenyl]-amine and

[10] Benzyl-[2-nitro-5-(4-phenyl-2-yl-piperazin-1 -yl)-phenyl]-amine;

optionally in form of a physiologically acceptable salt thereof, or a corresponding solvate thereof.

In yet another aspect the present invention relates to nitro-substituted phenyl- piperazine compounds of general formula I,

wherein

X represents a -NR ¹ R ² moiety or a -OR ³ moiety;

R ¹ represents a saturated or unsaturated, optionally at least mono-substituted 3- to 9-membered cycloaliphatic radical, which is bonded via a linear or branched, optionally at least mono-substituted C ₁ - ₆ alkylene, C ₂ - ₆ alkenylene or C-2-6 alkinylene group and/or which may contain 1 , 2 or 3 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulphur as ring member(s);

an optionally at least mono-substituted heteroaryl radical selected from the group consisting of furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1- b]thiazolyl;

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ )-group and/or may be substituted with 1 , 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of Ci. ₅ -alkyl, -O-Ci _-5 -alkyl, -S-Ci _-5 -alkyl, -C(=O)-Ci _-5 -alkyl, - C(=O)-O-Ci _-5 -alkyl, -O-C(=O)-C _1-5 -alkyl, F, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , - OH, -SH, -NH ₂ , -NH(C _1-5 -alkyl), -N(Ci _-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , - CK=O)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ , -S(=O) ₂ -C _1-5 -alkyl, - S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

an aryl or heteroaryl radical selected from the group consisting of naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby

said aryl or heteroaryl radical is bonded via a -(CH ₂ )2-group and/or may be substituted with 1 , 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of Ci _-5 -alkyl, -O-C _1-5 -alkyl, -S-Ci _-5 -alkyl, -C(=O)-OH, -C(=O)- d-s-alkyl, -C(=O)-O-C _1-5 -alkyl, -O-C(=O)-C _1-5 -alkyl, F, Cl, Br, I, -CN, -CF ₃ , - OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(C _1-5 -alkyl), -N(C _1-5 -alkyl) ₂ , -NO ₂ , -CHO, - CF ₂ H, -CFH ₂ , -C(=O)-NH ₂₎ -C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂₎ - S(=O) ₂ -Ci- ₅ -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ ) ₃ -group and/or may be substituted with 1 , 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of C _1-5 -alkyl, -O-Ci _-5 -alkyl, -S-Ci _-5 -alkyl, -C(=O)-OH, -C(=O)- d-s-alkyl, -C(=O)-O-C _1-5 -alkyl, -O-C(=O)-Ci _-5 -alkyl, F, Cl, Br, I, -CN, -CF ₃ , - OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(C _1-5 -alkyl), -N(C _1-5 -alkyl) ₂ , -NO ₂ , -CHO, - CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ , - S(=O) ₂ -Ci- ₅ -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

or

a -C(=O)-R ¹² moiety;

R ² represents a hydrogen atom or a linear or branched, saturated or unsaturated, optionally at least mono-substituted CM _O aliphatic radical;

R ¹ and R ² together with the bridging nitrogen form an optionally at least mono- substituted, saturated or unsaturated, but not aromatic 3- to 9-membered heterocyclic ring which may contain 1 , 2 or 3 additional heteroatom(s) independently selected from the group consisting of nitrogen and sulphur as ring member(s);

R ³ represents an optionally at least mono-substituted 5- to 10-membered aryl or heteroaryl radical, which may be bonded via a linear or branched, optionally at least mono-substituted Ci _-6 alkylene, C _2-6 alkenylene or C _2-6 alkinylene group and whereby the heteroaryl radical contains 1 , 2 or 3 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulphur as ring member(s);

R ⁴ , R ⁵ and R ⁶ each represent a hydrogen atom;

R ⁷ and R ⁸ , identical or different, each represent a hydrogen atom or a linear or branched, saturated or unsaturated, optionally at least mono-substituted CM ₀ aliphatic radical;

R ⁹ and R ¹⁰ , identical or different, each represent a hydrogen atom or a linear or branched, saturated or unsaturated, optionally at least mono-substituted C-M _O aliphatic radical;

R ¹¹ represents a linear or branched, saturated or unsaturated, unsubstituted CM ₀ aliphatic radical or an optionally at least mono-substituted 5- to 10-membered aryl or heteroaryl radical whereby the heteroaryl radical contains 1 , 2 or 3 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulphur as ring member(s);

and

R ¹² represents an aryl radical which may be substituted with 1 , 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of Ci- ₅ -alkyl, O-C _1-5 -alkyl, -S-C _1-5 -alkyl, -C(=O)-OH, -C(=O)-Ci^-alkyl,-C(=O)-O-Ci^-alkyl, O-C(=O)-Ci-5-alkyl, F, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -SH ₁ -NH ₂ , -NH(C _1-5 - alkyl), -N(C _1-5 -alkyl) ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(Ci _-5 - alkyl), -C(=O)-N(C _1-5 -alkyl) ₂₎ -S(=O) ₂ -Ci- ₅ -alkyl, -S(=O) ₂ -phenyi, phenyl, phenoxy and benzyl;

an optionally at least mono-substituted heteroaryl radical selected from the group consisting of furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1- b]thiazolyl;

or

an optionally at least mono-substituted aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ )i, ₂ or ₃ - group;

with the proviso that the following compound

(1 ) Benzyl-[5-(4-methyl-piperazin-1 -yl)-2-nitro-phenyl]-amine may preferably be excluded;

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.

If any of the substituents represents or comprises a (hetero)cycloaliphatic radical [(hetero)cycloaliphatic group], said (hetero)cycloaliphatic radical may - if not defined otherwise - be unsubstituted or substituted by one or more substituents, preferably unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituent(s). Said substituent(s) may preferably be selected independently from the group consisting of oxo (=0), thioxo C=S) ₁ Ci- ₅ -alkyl, -O-Ci _-5 -alkyl, -S-C _1-5 -alkyl, -C(=O)-OH, -C(=O)-C _1-5 -alkyl, -C(=O)-O- d-s-alkyl, -O-C(=O)-Ci _-5 -alkyl, F, Cl, Br, I ₁ -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ ,

-NH(C ₁ .5-alkyl), -N(Ci _-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)- NH(Ci _-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ , -S(=O) ₂ -C _1-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl; whereby in each occurence Ci _-5 -alkyl may be linear or branched and whereby said cyclic substituents may be unsubstituted or substituted by 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, F, Cl, Br, -CN, -CF ₃ , -OCF ₃ , - SCF ₃ , -OH, -SH, -NH ₂ and NO ₂ .

More preferably said substituents may be selected independently from the group consisting of oxo (=O), thioxo (=S), methyl, ethyl, n-propyl, isopropyl, n-butyl, tert- butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CHg) ₂ , -S-C(CH ₃ ) ₃ , -C(=O)- OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , - C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH _3l -C(=O)-C ₂ H _5> -C(=O)-CH ₂ -CH ₂ -CH ₃₍ -C(=O)- CH(CHs) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I ₁ -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , - NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CHs) ₂ , -NH-C(CH ₃ ) ₃ , -N(CH ₃ ) _2l - N(C ₂ Hs) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH- C ₂ H ₅ , -C(=O)-N(CH ₃ ) _2> -C(=O)-N(C ₂ H ₅ ) _2l -S(=O) ₂ -CH ₃ , -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl; whereby in each occurence said cyclic substituents may be unsubstituted or substituted by 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, F, Cl, Br, - CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ and NO ₂ .

If any of the substituents represents or comprises a cycloaliphatic radical, which contains one or more, preferably 1 , 2 or 3 heteroatom(s) as ring member(s), unless defined otherwise, each of these heteroatom(s) may preferably be selected independently from the group consisting of N, O and S.

Suitable (hetero)cycloaliphatic radicals, which may be unsubstituted or at least mono- substituted, include cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, cycloheptenyl, cyclooctyl, cyclooctenyl, cyclononyl, imidazolidinyl, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl and

azepanyl.

If any of the substituents represents or comprises an aryl radical (aryl group), including a phenyl or naphthyl group, said aryl radical may - if not defined otherwise - be unsubstituted or substituted by one or more substituents, preferably unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituent(s). Said substituent(s) may preferably be selected independently from the group consisting of Ci- ₅ -alkyl, -O-Ci _-5 -alkyl, -S-Ci _-5 - alkyl, -C(=O)-OH, -Cl=O)-C _{1 -5} -alkyl, -C(=O)-O-C _1-5 -alkyl, -O-C(=O)-C _1-5 -alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -SH, -NH ₂ , -NH(Ci. ₅ -alkyl), -N(C _1-5 -alkyl) _2> -NO ₂ , - CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ , - S(=O) ₂ -Ci- ₅ -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl; whereby in each occurrence Ci- ₅ -alkyl may be linear or branched and whereby said cyclic substituent(s) may be unsubstituted or substituted by 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, F, Cl, Br, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ and NO ₂ .

More preferably said substituents may be selected independently from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S- C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S-C(CH ₃ ) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , - C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH _3l -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , - C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -CC=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ - CH ₂ -CH ₃ , -NH-CH(CHg) ₂ , -NH-C(CH ₃ ) _3> -N(CH ₃ ) ₂ , -N(C ₂ Hs) ₂ , -NO ₂ , -CHO, -CF ₂ H, - CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)- N(C ₂ Hs) ₂ and -S(=O) ₂ -CH ₃ .

Preferred aryl radicals, which may optionally be at least mono-substituted, are phenyl and naphthyl.

If any of the substituents represents or comprises a heteroaryl radical (heteroaryl group), said heteroaryl radical may - if not defined otherwise - be unsubstituted or substituted by one or more substituents, preferably unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituent(s). Said substituent(s) may preferably be

selected independently from the group consisting of C _1-5 -alkyl, -O-C _1-5 -a!kyl, -S-C _1-5 - alkyl, -C(=0)-0H, -C(=O)-Ci _-5 -alkyl, -C(=O)-O-C _1-5 -alkyl, -O-C(=O)-C _1-5 -alkyl, F, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -SH ₁ -NH ₂ , -NH(C _1-5 -alkyl), -N(Ci _-5 -alkyl) _2l -CHO, -CF ₂ H, - CFH ₂ , -C(=0)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(Ci _-5 -alkyl) ₂ , -S(=O) ₂ -Ci _-5 -alkyl, - S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl; whereby in each occurrence Ci- ₅ -alkyl may be linear or branched and whereby said cyclic substituent(s) may be unsubstituted or substituted by 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, F, Cl, Br, - CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ and NO ₂ .

More preferably said substituents may be selected independently from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S- C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S-C(CH ₃ ) ₃ , -C(=0)-0H, -C(=O)-O-CH ₃ , - C(=O)-O-C ₂ H ₅ , -CC=O)-O-CH ₂ -CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , - C(=0)-CH ₃₎ -CC=O)-C ₂ H ₅ , -CC=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ - CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CH ₃ ) ₃ , -N(CH ₃ ) ₂ , -N(C ₂ H ₅ ) ₂ , -NO ₂ , -CHO, -CF ₂ H, - CFH ₂ , -C(=0)-NH ₂ , -C(=0)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂₍ -C(=0)- N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ .

The heteroatom(s), which are present as ring member(s) in the heteroaryl radical, may, unless defined otherwise, independently be selected from the group consisting of nitrogen, oxygen and sulphur. Preferably the heteroaryl radical comprises 1 , 2 or 3 heteroatom(s).

Suitable heteroaryl radicals, which may optionally be at least mono-substituted, may preferably be selected from the group consisting of furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl, benzoxadiazolyl, benzoxazolyl, benzthiazolyl, benzisoxazolyl, benzisothiazolyl and imidazo[2,1 -b]thiazolyl.

If at least two of the substituents together with the bridging nitrogen atom form a saturated or unsaturated heterocyclic ring, said heterocyclic ring may preferably be selected from the group consisting of

Those skilled in the art understand that the afore mentioned cyclic moieties, which contain an NH group may also be substituted in this position, i.e. the hydrogen atom may be exchanged for another substituent.

Said heterocyclic rings may - if not defined otherwise - be unsubstituted or substituted by one or more substituents, preferably unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituent(s). Said substituent(s) may preferably be selected independently from the group consisting of C-i-s-alkyl, -O-Ci- ₅ -alkyl, -S-Ci- ₅ -alkyl, oxo (=0), thioxo (=S), -C(=O)-OH, -C(=O)-C _1-5 -alkyl, -C(=O)-O-C _1-5 -alkyl, -O-C(=O)-C _1-5 - alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(Ci _-5 -alkyl), -N(C _1-5 - alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), -C^O)-N(C _{1- 5} -alkyl) ₂ , -S(=O) ₂ -C _1-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl; whereby in each occurrence C _1-5 -alkyl may be linear or branched and whereby said cyclic substituent(s) may be unsubstituted or substituted by 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, F, Cl, Br, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ and NO ₂ .

More preferably said substituents may be selected independently from the group consisting of oxo (=0), thioxo (=S), methyl, ethyl, n-propyl, isopropyl, n-butyl, tert- butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S-C(CH ₃ J ₃ , -C(=O)- OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , - C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)- CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , - NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CH ₃ ) ₃ , -N(CH ₃ ) ₂ , - N(C ₂ Hs) ₂ , -NO ₂ , -CHO ₁ -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH- C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ , -S(=O) ₂ -CH ₃ , -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl; whereby said cyclic substituent(s) may be unsubstituted or substituted by 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, F, Cl, Br, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ and NO ₂ .

If any of the substituents represents a saturated or unsaturated aliphatic radical (aliphatic group), i.e. an alkyl radical, an alkenyl radical or an alkinyl radical, said aliphatic radical may - if not defined otherwise - be unsubstituted or substituted by one or more substituents, preferably unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituent(s). Said substituent(s) may preferably be selected independently from the group consisting of -O-C _1-5 -alkyl, -S-C _1-5 -alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , - OH, -SH, -NH ₂ , -NH(Ci _-5 -alkyl) and -N(Ci _-5 -alkyl) ₂ , whereby in each occurence Ci _-5 - alkyl may be linear or branched. More preferably said substituent(s) may preferably be selected independently from the group consisting of -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ - CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S- CH(CH ₃ ) ₂ , -S-C(CHa) ₃ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , NH- CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CH ₃ ) ₃ , -N(CH ₃ ) ₂ , -

An alkenyl radical comprises at least one carbon-carbon double bond, an alkinyl radical comprises at least one carbon-carbon triple bond.

Suitable alkyl radicals, which may be substituted by one or more substituents, may preferably be selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and n-decyl.

Suitable alkenyl radicals, which may be substituted by one or more substituents, may preferably be selected from the group consisting of vinyl, 1-propenyl, 2-propenyl, 1- butenyl, 2-butenyl and 3-butenyl.

Suitable alkinyl radicals, which may be substituted by one or more substituents, may preferably be selected from the group consisting of ethinyl, 1-propinyl, 2-propinyl, 1- butinyl, 2-butinyl and 3-butinyl.

Preferred are compounds of general formula I given above, wherein R ¹ represents an (hetero)cycloaliphatic radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, cycloheptenyl, cyclooctyl, cyclooctenyl, cyclononyl, imidazolidinyl, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl and azepanyl whereby said (hetero)cylcoaliphatic radical can be bonded via a linear or branched, optionally at least mono-substituted Ci _-6 alkylene, C _2-6 alkenylene or C _2-6 alkinylene group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of oxo (=O), thioxo (=S), Ci- ₅ -alkyl, -O-Ci _-5 -alkyl, -S-Ci _-5 -alkyl, - C(=O)-OH, -C(=O)-Ci- ₅ -alkyl, -CC=O)-O-C _{1 -5} -alkyl, -O-C(=O)-C _1-5 -alkyl, F, Cl, Br, I, - CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(C _1-5 -alkyl), -N(C _1-5 -alkyl) ₂ , -NO ₂ , - CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(Ci _-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ , - S(=O) ₂ -Ci- ₅ -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

a heteroaryl radical selected from the group consisting of furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said heteroaryl radical may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of Ci- ₅ -alkyl, -O- d- ₅ -alkyl, -S-Ci- ₅ -alkyl, -C(=O)-OH, -C(=O)-C _1-5 -alkyl, -C(=O)-O-Ci _-5 -alkyl, -O-C(=O)-

d-s-alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH ₁ -NH ₂ , -NH(Ci _-5 -alkyl), - N(C _1-5 -alkyl)2, -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), - C(=O)-N(C _1-5 -alkyl) ₂ , -S(=O) ₂ -Ci _-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a - (CH ₂ )-group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of Ci _-5 -alkyl, -O-Ci- ₅ -alkyl, -S-Ci. ₅ -alkyl, -C(=O)- Ci- ₅ -alkyl, -CC=O)-O-C _{1 -5} -alkyl, -O-C(=O)-C _1-5 -alkyl, F, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(Ci _-5 -alkyl), -N(C _1-5 -alky!) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)- NH ₂ , -C(=O)-NH(Ci _-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ , -S(=O) ₂ -C _1-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

an aryl or heteroaryl radical selected from the group consisting of naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ ) ₂ -group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of Ci- ₅ -alkyl, -O-Ci _-5 -alkyl, -S-Ci- ₅ - alkyl, -C(=O)-OH, -C(=O)-C _1-5 -alkyl, -C(=O)-O-Ci _-5 -alkyl, -O-C(=O)-C _1-5 -alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(Ci _-5 -alkyl), -N(C _1-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(Ci _-5 -alkyl), -C(=O)-N(Ci _-5 -alkyl) ₂ , - S(=O) ₂ -Ci- ₅ -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ ) ₃ -group and/or may be substituted with 1 , 2 or 3 substituent(s)

independently selected from the group consisting of Ci _-5 -alkyl, -O-Ci _-5 -alkyl, -S-Ci _-5 - alkyl, -C(=O)-OH, -C(=O)-Ci _-5 -alkyl, -C(=O)-O-Ci _-5 -alkyl, -O-C(=O)-C _1-5 -alkyl, F, Cl ₁ Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(Ci _-5 -alkyl), -N(Ci _-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(C ₁ . ₅ -alkyl) ₂ , - S(=O) ₂ -Ci- ₅ -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

or

a -C(=O)-R ¹² moiety;

preferably R ¹ represents an (hetero)cycloaliphatic radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, cycloheptenyl, cyclooctyl, cyclooctenyl, cyclononyl, imidazolidinyl, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl and azepanyl whereby said (hetero)cylcoaliphatic radical can be bonded via a -(CH ₂ )i, _{2 or 3} - group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of oxo (=O), thioxo (=S), methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -O-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ - CH ₂ -CH ₃ , -0-CH(CHs) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S- CH(CHg) ₂ , -S-C(CHa) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ - CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , - C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , - OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH- CH(CHs) ₂ , -NH-C(CH ₃ )S, -N(CHs) ₂ , -N(C ₂ Hg) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)- NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and - S(=O) ₂ -CH ₃ ,

a heteroaryl radical selected from the group consisting of furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said heteroaryl radical may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl,

n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -O-C ₂ H ₅ , - 0-CH ₂ -CH ₂ -CH ₃ , -0-CH(CHs) ₂ , -0-C(CHs) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S- CH(CHa) ₂ , -S-C(CHa) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)~O-C ₂ H ₅ , -C(=O)-O-CH ₂ - CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , - C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , - OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH- CH(CH ₃ ) ₂ , -NH-C(CH ₃ )S, -N(CHs) ₂ , -N(C ₂ Hs) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)- NH ₂ , -C(=O)-NH-CH _3> -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N (C ₂ Hg) ₂ and - S(=O) ₂ -CHs,

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a - (CH ₂ )-group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert- butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S-C(CH ₃ ) ₃ , -C(=O)-O- CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O- C(CH ₃ ) _3> -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , - C(=O)-C(CH ₃ ) ₃ , F, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH- C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CHa) ₂ , -NH-C(CHa) ₃ , -N(CH ₃ ) ₂ , -N(C ₂ Hs) ₂ , -NO ₂ , - CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-N H-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)- N(CHs) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ,

an aryl or heteroaryl radical selected from the group consisting of naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ ) ₂ -group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -

O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂₎ -S- C(CHa) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , - C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) _3> -C(=O)-CH ₃ , -C(=O)-C ₂ H _5> -C(=O)-CH ₂ -CH ₂ - CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) _3l F ₁ Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, - SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CH ₃ ) ₃ , - N(CH ₃ ) ₂ , -N(C ₂ Hs) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂₎ -C(=O)-NH-CH ₃ , - C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ,

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ ) ₃ -group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , - O-CH(CH ₃ ) _2l -0-C(CHg) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S- C(CHg) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , - C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ - CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN ₁ -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, - SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CHg) ₂ , -NH-C(CHg) ₃ , - N(CHg) ₂ , -N(C ₂ Hs) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , - C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ,

or

a -C(=O)-R^ moiety;

more preferably R ¹ represents an unsubstituted pyrrolyl radical; an aryl or heteroaryl radical selected from the group consisting of phenyl and pyrrolyl, whereby said phenyl is bonded via a -(CH ₂ )-group and said pyrrolyl radical is bonded via a -(CH ₂ J _{1 or 2} - group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert- butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ ,

-0-C(CHs) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S-C(CH ₃ ) ₃ , -C(=O)-O- CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O- C(CHs) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , - C(=O)-C(CH ₃ ) ₃ , F, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH- C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CH ₃ ) ₃ , -N(CH ₃ ) ₂ , -N(C ₂ Hs) ₂ , -NO ₂ , - CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)- N(CH ₃ ) ₂ , -C(=O)-N (C ₂ Hg) ₂ and -S(=O) ₂ -CH ₃ or a -C(=O)-R ¹² moiety

and X and R ² to R ¹² have the above defined meaning, 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.

Furthermore such nitro-substituted phenyl-piperazine compounds of general formula I are preferred, wherein R ² represents a hydrogen atom or a linear or branched, unsubstituted C ₁ -10 alkyl radical;

preferably R ² represents a hydrogen atom or an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert- butyl;

more preferably R ² represents a hydrogen atom or a methyl radical;

and X, R ¹ and R ³ to R ¹² have the above defined meaning, 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.

Also preferred are such nitro-substituted phenyl-piperazine compounds of general formula I, wherein R ¹ and R ² together with the bridging nitrogen atom form a moiety selected from the group consisting of

whereby each of these afore mentioned cyclic moieties may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of Ci- ₅ -alkyl, -O- Ci-s-alkyl, -S-C _1-5 -alkyl, oxo (=0), thioxo (=S), -C(=O)-OH, -C(=O)-Ci _-5 -alkyl, -C(=0)- O-Ci- ₅ -alkyl, -O-C(=O)-Ci _-5 -alkyl, F ₁ Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, - NH ₂ , -NH(Ci _-5 -alkyl), -N(Ci _-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)- NH(Ci _-5 -alkyl), -C(=O)-N(Ci- ₅ -alkyl) ₂ , -S(=O) ₂ -C _1-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

preferably R ¹ and R ² together with the bridging nitrogen atom form a moiety selected from the group consisting of

whereby each of these afore mentioned cyclic moieties may be substituted with 1 , 2 or 3 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, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S- C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂₍ -S-C(CH ₃ ) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , - C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) _3l - C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) _3> F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ - CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CHg) ₃ , -N(CH ₃ ) ₂ , -N(C ₂ Hs) ₂ , -NO ₂ , -CHO, -CF ₂ H, - CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)- N(C ₂ H ₅ ) ₂ , -S(=O) ₂ -CH ₃ , -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

more preferably R ¹ and R ² together with the bridging nitrogen atom form a pyridazin- 3-one moiety;

and X and R ³ to R ¹² have the above defined meaning, 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.

Moreover, such nitro-substituted phenyl-piperazine compounds of general formula I given above are preferred, wherein R ³ represents an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical may be bonded via a - (CH ₂ )L _{2 o} r ₃ -group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of Ci _-5 -alkyl, -O-Ci _-5 -alkyl, -S-Ci _-5 - alkyl, -C(=O)-OH, -C(=O)-C _1-5 -alkyl, -C(=O)-O-C _1-5 -alkyl, -O-C(=O)-Ci _-5 -alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(d. ₅ -alkyl), -N(C _1-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(Ci _-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ , - S(=O) ₂ -Ci _-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

preferably R ³ represents an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical may be bonded via a -(CH ₂ )i, _{2 O} r ₃ -group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S- CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S-C(CHg) ₃ , -C(=O)-OH, -C(=O)-O- CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O- C(CHg) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ -CH ₃₎ -C(=O)-CH(CH ₃ ) ₂ , - C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH- C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CH ₃ ) ₃ , -N(CH ₃ ) ₂ , -N(C ₂ Hg) ₂ , -NO ₂ , - CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH _2> -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)- N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ,

more preferably R ³ represents a phenyl radical which may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n- propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , - 0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂₎ -O-C(CH ₃ ) ₃ , -S-CH3, -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S- CH(CHs) ₂ , -S-C(CHs) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃₎ -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ - CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , - C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F ₁ Cl, Br, I, -CN, -CF ₃ , - OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH- CH(CHs) ₂ , -NH-C(CHs) ₃ , -N(CH ₃ ) _2l -N(C ₂ Hg) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)- NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N (C ₂ Hg) ₂ and - S(=O) ₂ -CH ₃ ;

and X, R ¹ , R ² and R ⁴ to R ¹² have the above defined meaning, 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.

Also preferred are nitro-substituted phenyl-piperazine compounds of general formula I, wherein R ⁷ and R ⁸ , identical or different, each represent a hydrogen atom or a linear or branched, unsubstituted Ci-i _O alkyl radical;

preferably R ⁷ and R ⁸ , identical or different, each represent a hydrogen atom or an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl;

more preferably R ⁷ and R ⁸ each represent a hydrogen atom;

and X, R ¹ to R ⁶ and R ⁹ to R ¹² have the above defined meaning, 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.

Also preferred are nitro-substituted phenyl-piperazine compounds of general formula I, wherein R ⁹ and R ¹⁰ , identical or different, each represent a hydrogen atom or a linear or branched, unsubstituted C-t-io alkyl radical;

preferably R ⁹ and R ¹⁰ , identical or different, each represent a hydrogen atom or an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl;

more preferably R and R >10 each represent a hydrogen atom;

and X, R ¹ to R ⁸ and R ¹¹ and R ¹² have the above defined meaning, 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.

Also preferred are nitro-substituted phenyl-piperazine compounds of general formula I, wherein R ¹¹ represents a linear or branched, unsubstituted Ci-i _O alkyl radical; or an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl whereby said aryl or heteroaryl may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of C _1-5 -alkyl, -O-Ci. ₅ -alkyl, -S-Ci _-5 -alkyl, -C(=O)-OH, -C(=O)-C _1-5 -alkyl, - C-C=O)-O-C ₁ -s-alkyl, -O-C(=O)-Ci _-5 -alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, - SH, -NH ₂ , -NH(C _1-5 -alkyl), -N(C _1-5 -alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , - C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(C _1-5 -alkyl) ₂ , -S(=O) ₂ -C _1-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

preferably R ¹¹ represents an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl; or an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S- C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S-C(CH ₃ ) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , - C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , - C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C^O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ - CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CHg) ₃ , -N(CH ₃ ) ₂ , -N(C ₂ Hg) ₂ , -NO ₂ , -CHO, -CF ₂ H, - CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)- N(C ₂ Hs) ₂ and -S(=O) ₂ -CH ₃ ;

more preferably R ¹¹ represents an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl and n-butyl; or an unsubstituted phenyl or pyridinyl radical;

and X ₁ R ¹ to R ¹⁰ and R ¹² have the above defined meaning, 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.

Also preferred are nitro-substituted phenyl-piperazine compounds of general formula I, wherein R ¹² represents an aryl radical which may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of whereby said aryl radical may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of Ci _-5 -alkyl, -O-Ci _-5 -alkyl, -S-C _1-5 -alkyl, -C(=O)-OH, -C(=O)-Ci _-5 - alkyl, -C(=O)-O-C _1-5 -alkyl, -O-C(=O)-C _1-5 -alkyl, F, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , - SH, -NH ₂ , -NH(C _1-5 -alkyl), -N(C _1-5 -alkyl) ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH _2> -C(=O)- NH(C _1-5 -alkyl), -C(=O)-N(Ci _-5 -alkyl) ₂ , -S(=O) ₂ -C _1-5 -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

an optionally at least mono-substituted heteroaryl radical selected from the group consisting of furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl whereby said heteroaryl radical may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of Ci- ₅ -alkyl, -O-Ci- ₅ -alkyl, -S-C- _t -5-alkyl, -C(=O)- OH, -C(=O)-C _1-5 -alkyl, -C(=O)-O-C _1-5 -alkyl, -O-C(=O)-Ci _-5 -alkyl, F, Cl, Br, I, -CN, - CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH(C _1-5 -alkyl), -N(C _1-5 -alkyl) ₂ , -NO ₂ , -CHO, - CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), -C(=O)-N(Ci _-5 -alkyl) ₂ , -S(=O) ₂ -C _1-5 - alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

or

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ )i, 2 or 3- group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of Ci _-5 -alkyl, -0-C _1-5 - alkyl, -S-d-s-alkyl, -C(=O)-OH, -C(=O)-Ci _-5 -alkyl, -C(=O)-O-C _1-5 -alkyl, -O-C(=O)-C _1-5 - alkyl, F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH ₁ -SH, -NH ₂ , -NH(C _1-5 -alkyl), -N(C _1-5 - alkyl) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH(C _1-5 -alkyl), -Ct=O)-N(C _{1- 5} -alkyl) ₂ , -Sl=O) ₂ -C _{1 -5} -alkyl, -S(=O) ₂ -phenyl, phenyl, phenoxy and benzyl;

preferably R ¹² represents an aryl radical which may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n- propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , - 0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH3, -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S- CH(CHs) ₂ , -S-C(CHs) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ - CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , - C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) _2l -C(=O)-C(CH ₃ ) ₃ , F, Br, I, -CN, -CF ₃ , -OCF ₃ , - SCF ₃ , -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH- C(CHg) ₃ , -N(CHs) ₂ , -N(C ₂ Hs) ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , - C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ;

an optionally at least mono-substituted heteroaryl radical selected from the group consisting of furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl whereby said heteroaryl radical may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert- butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , -0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH3, -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S-CH(CH ₃ ) ₂ , -S-C(CHs) ₃ , -C(=O)- OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ -CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) _2> - C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , -C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-

CH(CH ₃ ) ₂ , -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , -OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , - NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH-CH(CH ₃ ) ₂ , -NH-C(CH ₃ ) ₃ , -N(CHg) ₂ , - N(C ₂ Hs) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)-NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH- C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and -S(=O) ₂ -CH ₃ ;

or

an aryl or heteroaryl radical selected from the group consisting of phenyl, naphthyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzothiadiazolyl and imidazo[2,1-b]thiazolyl, whereby said aryl or heteroaryl radical is bonded via a -(CH ₂ )i, _{2 o} r3- group and/or may be substituted with 1 , 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, n- propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, -0-CH ₃ , -0-C ₂ H ₅ , - 0-CH ₂ -CH ₂ -CH ₃ , -O-CH(CH ₃ ) ₂ , -O-C(CH ₃ ) ₃ , -S-CH ₃ , -S-C ₂ H ₅ , -S-CH ₂ -CH ₂ -CH ₃ , -S- CH(CHs) ₂ , -S-C(CHs) ₃ , -C(=O)-OH, -C(=O)-O-CH ₃ , -C(=O)-O-C ₂ H ₅ , -C(=O)-O-CH ₂ - CH ₂ -CH ₃ , -C(=O)-O-CH(CH ₃ ) ₂ , -C(=O)-O-C(CH ₃ ) ₃ , -C(=O)-CH ₃ , -C(=O)-C ₂ H ₅ , - C(=O)-CH ₂ -CH ₂ -CH ₃ , -C(=O)-CH(CH ₃ ) _2> -C(=O)-C(CH ₃ ) ₃ , F, Cl, Br, I, -CN, -CF ₃ , - OCF ₃ , -SCF ₃ , -OH, -SH, -NH ₂ , -NH-CH ₃ , -NH-C ₂ H ₅ , -NH-CH ₂ -CH ₂ -CH ₃ , -NH- CH(CH ₃ ) ₂ , -NH-C(CHs) ₃ , -N(CH ₃ ) ₂ , -N(C ₂ Hg) ₂ , -NO ₂ , -CHO, -CF ₂ H, -CFH ₂ , -C(=O)- NH ₂ , -C(=O)-NH-CH ₃ , -C(=O)-NH-C ₂ H ₅ , -C(=O)-N(CH ₃ ) ₂ , -C(=O)-N(C ₂ H ₅ ) ₂ and - S(=O) ₂ -CH ₃ ;