ZA200609734B

ZA200609734B - Indolizine carboxamides and the aza and diaza derivatives thereof

Info

Publication number: ZA200609734B
Application number: ZA200609734A
Authority: ZA
Inventors: Gmeiner Peter; Hubner Harald; Bettinetti Laura; Schlotter Karin
Original assignee: Sanol Arznei Schwarz Gmbh
Priority date: 2004-08-02
Filing date: 2006-11-22
Publication date: 2008-04-30
Also published as: CN101014599A; DE102004037445A1

Description

Indolizine carboxamides and their aza and diaza derivatives

Description

Dopamine is an important neurotransmitter of the central nervous system. Dopamine is effective by bonding to five different dopamine receptors. As a result of their morphology and the nature of their signal transmission these can be classified as D1-like (D1 and D5) and D2-like (D2-, D3- and D4-receptors) (Neve, K.A. The Dopamine Receptors. Humana

Press, 1997). The sub-types of the D2 family in particular have an important part to play in the regulation of central nervous processes. While the D2-receptors are predominantly expressed in the basal ganglions and are involved there in the control and modulation of neuromotor circuits, D3-receptors are mainly found in the mesolimbic system, in which emotional and cognitive processes are controlled. Disturbances in the signal transduction of these receptors lead to a number of neuropathological changes which can sometimes result in serious illnesses. As a result the D3-receptor is a promising target for the development of active substances for the treatment of psychiatric ilinesses such as schizophrenia or unipolar depressions, of disturbances of consciousness and for treatment of neurodegenerative diseases such as Parkinson's and the dyskineses that can occur in the course of long-term therapy, but also for the treatment of drug dependency (Pulvirenti, L. et al. Trends Pharmacol. Sci. 2002, 23, 151-153, Joyce, J.N. Pharmacol.

Ther. 2001, 90, 231-259). Here the most D3-receptor-selective bonding profile should be sought for such active substances. Depending on the intrinsic activity (full agonist, partial agonist, antagonist or inverse agonist) such ligands can have a stimulating, modulating or also inhibiting effect on the pathologically altered dopamine signal transduction system and can thus be used for the treatment of these diseases.

Compounds with an arylpiperazine structure have previously been described as dopamine receptor-active ligands (Robarge, M.J. J. Med. Chem. 2001, 44, 3175-3186). Benzamides and naphthamides with arylpiperazine partial structures are also known as ligands of dopamine receptors (Perrone, R. J. Med. Chem. 1998, 41, 4903-4909; EP 0 779 284 A1).

Recently heteroarene amides have also been described as D3-receptor-active compounds (Bettinetti, L. et al. J. Med. Chem. 2002, 45, 4594-4597, Leopoldo, M. et al. J. Med. Chem. 2002, 45, 5727-5735, WO 2004/004729 A1). A phenylpiperazinylnaphthamide has also recently been reported on as a selective D3-partial agonist, which demonstrated hopeful activities in the animal model, and which could be used for the treatment of cocaine

De addiction (Pilla, M. et al. Nature 1999, 400, 371-375). Furthermore, because of the characteristic features of this compound elimination of the serious motor impairments (dyskinesias) caused by long-term treatment of Parkinson's disease with the pharmaceutical preparations L-DOPA can be achieved (Bezard, E. et al. Nature Med. 2003, 9, 762-767). The most recent literature describes the neuro-protective effect of D3- selective partial agonists against MPTP-induced neurone loss in mice as a murine model for Parkinson's disease (Boeckler, F. et al. Biochem. Pharmacol. 2003, 6, 1025-1032).

Of the range of arylpiperazinylheteroarene carboxamides structure examples with oxygen-, sulphur- or nitrogen-containing heteroarene carboxylic acid components are above all described (ES 2027898; EP 343 961; US 3646047; US 3734915; WO 2004/024878,

Leopoldo, M. et al. J. Med. Chem. 2002, 45, 5727-5735, WO 2004/004729 A1). Indolizine- substituted ligands are not disclosed in these references.

Bettinetti, L. et al. J. Med. Chem. 2002, 45, 4594-4597 described for the first time a few pyrazolo[1,5-alpyridines with an affinity to the D3-receptor. Other indolizine-substituted ligands have, however, not been described to date.

In connection with our structure-effect research into dopamine receptor ligands we have discovered new compounds of formula (I) - (IX). During in vitro research these demonstrated a particularly high affinity and selective bonding characteristics to the D3- receptor. Some compounds also demonstrate a notable affinity to serotoninergic receptors, in particular to the 5-HT 1a-receptor.

The compounds according to the invention could therefore constitute valuable therapeutic agents for the treatment of central nervous system disorders, such as schizophrenia or various types of depression, for neuroprotection in neurodegenerative diseases, in addictive disorders, glaucoma, cognitive disorders, restless leg syndrome, attention deficit hyperactive syndrome (ADHS), hyperprolactinemia, hyperprolactinomia and autism, in idiopathic or medically-induced extrapyramidal motor disturbances, such as acathisia, rigor, dystonias and dyskinesias, as well as various disorders of the urinary tract.

The subject-matter of this invention comprises compounds of the general formula |,

Q

Qe” T=

A | glx od AEG

ENN SIN 2

Q; Q; in which:

Ais a saturated or aromatic 6-membered ring;

B is an aromatic 5-membered ring; the heteroarene formed from A+B has a total of a maximum of three N-atoms and precisely one X group;

Q1, Q2 and Q3 are in each case and independently of each other N, CH or C-R1;

Q4 is N-R, CH-R1’ or C-R1R1;

Q5, Q6 and Q7 are independently of each other CH-R1’' or C-R1R1’;

R1 is in each case selected from the hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino group;

R1' is absent if ring A is aromatic or is hydrogen if ring A is saturated;

Ris absent if ring A is aromatic or is selected from hydrogen, alkyl, phenyl, alkylcarbonyl, phenylcarbonyl, phenylalkyl and phenylsulfonyl, if ring A is saturated;

X is a group bonded to a C-atom of an aromatic ring A or B of the general formula X1 o R2 R3

Hi pL ho

R6 R5

In which:

Y is an unbranched, saturated or unsaturated hydrocarbon chain with 2-5 hydrocarbon atoms or a chain —(CH2),-Z-(CH2),, in which Z is selected from the residues cyclopentyl, cyclohexyl and cycloheptyl, wherein o and p in each case and independently of each other have the value 0, 1, 2 or 3 and wherein the sum of 0 and p is a maximum of 3;

R2, R3, R4, R5 and R6 are in each case selected independently of each other from the hydrogen, hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenylalkyl, phenoxy, phenylalkyloxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, phenylalkyloxycarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino group, wherein two vicinal residues R2, R3, R4, R5 and R6 together with the C-atoms of the phenyl ring to which they are bonded, can form an oxygen-containing 5-, 6- or 7-membered ring;

R7 is hydrogen, alkyl or phenylalkyl; in the form of the free base, the physiologically acceptable salts and possible enantiomers and diastereomers, with the proviso of exclusion of (a) compounds in which the heterocycle is a pyrazolo[1,5-a]pyridine, in particular if this carries as the sole substituent the X group, but no R1 substituent, wherein for X:

R2 = methoxy; R3, R4, R5, R6 and R7 are in each case hydrogen and (i) Y = ethylene, n-propylene or n-butylene or (ii) Y = n-pentylene and X is in 2- or 3-position linked with the pyrazolo[1,5- a] pyridine core

3 oe ; 5 Amended page as filed on 23™ March 2007 : Patent Attorney ~ (b) The compound N-4-(4-(2-chlorophenyl)piperazin-1-yl)butyl-7-methylpyrazolo[1,5- a]pyridin-3-ylcarbamide.

So

Inthe compounds of general formula |, as defined in more detail above, the X group can basically be linked to any ring-forming carbon of an aromatic ring A or B suitable for bonding. If Ais a saturated ring, X is bonded to a carbon atom of ring B. The significance of the groups Q1, Q2, Q3, Q4, Q5, Q6 and Q7 in formula |, as described in more detail above, must accordingly be understood according to the invention to be that one of the | ring-forming carbons of an aromatic ring contained in the groups Qf, Q2, Q3,Q4,Q5,Q6 ‘and Q7 is substituted with the X group and forms the C-X group. So bo : "The term “saturated ring A” and grammatical equivalents of this term mean in the present patent application that the ring A has maximum saturation, i.e. all ring-forming atoms of ringA which are not simultaneously part of aromatic ring B are completely saturated.

In one embodiment of the invention the two rings A and B, apart from the X group, have a : | maximum of 4,3, 2 or 1 substituents R1 or are unsubstituted apart from the X group.

In a preferred embodiment of the invention the R1 substituents of the heteroarenes in the : compounds according to the invention of general formulae Ni fil, IV, V, VI, VI, Vill and 1X are selected from the group comprising hydroxy, fluorine, chlorine, bromine, trifluoromethyl, cyano, amino, carboxy, sulfo, sulfamoyi, unsubstituted or hydroxy substituted C1-C6 alkyl, unsubstituted or hydroxy substituted C1-C6 alkyloxy, unsubstituted or hydroxy substituted C1-C6 alkylthio, unsubstituted C2-C6 alkinyl, unsubstituted or with fluorine, chlorine or bromine and/or with one or more methoxy groups substituted phenyl, unsubstituted or with fluorine, chlorine or bromine and/or with one or more methoxy groups substituted phenoxy, -C(O)-C1-C6 alkyl, wherein the alkyl is ) : unsubstituted or substituted with hydroxy, -C(O)-phenyl, wherein the phenyl is in each case unsubstituted or substituted with fluorine, chlorine or bromine and/or with one or more methoxy groups, C1-C6 alkyloxycarbony, wherein the alkyl is unsubstituted or substituted with hydroxy, C1-6 alkylaminosulfonyl, in particular methylaminosuffonyl and C1-6 alkylsulfonylamino, in particular methanesulfonylamino.

The substituent Q4 in Ring A, depending on the degree of saturation of the ring A, stands for N-R, CH-R1" or C-R1R1". In a saturated ring A, R1’ stands for hydrogen and Q4 is we oo . Amended page as filed on 23" March 2007 } . Patent Attorney selected from NR, CH, and CH-R1, wherein R is preferably selected from hydrogen, phenylalkyl and phenylsulfonyl and wherein R1 has the significance defined in more detail above. In an aromatic ring A the substituents R and R1’ are absent; Q4 is then selected \ from among N, CH and C-R1. If Q4 contains a nitrogen atom, this is preferably uncharged.

Co : R2, R3, R5 and R6 are in the compounds according to the invention of the general formulae I, II, 11, IV, V, VI, VII, VIII and IX preferably and independently of each other selected from the group comprising hydroxy, fluorine, chlorine, bromine, trifluoromethyl, cyano, amino, carboxy, sulfo, sulfamoyl, unsubstituted or hydroxy substituted C1-C6 alkyl, unsubstituted or hydroxy substituted C1-C6 alkyloxy, unsubstituted or hydroxy substituted

C1-C6 alkylthio, unsubstituted C2-C6 alkinyl, unsubstituted or with fluorine, chlorine or oh bromine and/or with one or more methoxy groups substituted phenyl, unsubstituted or with fluorine, chlorine or bromine and/or with one or more methoxy groups substituted phenoxy, - -C(0)-C1-C6 alkyl, wherein the alkyl is unsubstituted or hydroxy substituted, -C(O)-phenyl, phenylalkyloxy or phenylalkyloxycarbonyl, wherein the phenyl is in each case unsubstituted ~~ orwith fluorine, chlorine or bromine and/or with one or more methoxy groups substituted,

C1-C6 alkyloxycarbonyl, wherein the alkyl is unsubstituted or hydroxy substituted, C16 alkylaminosulfonyl, in particular methylaminosulfonyl and C1-6 alkylsulfonylamino, in particular methanesulfonytamino, or two vicinal residues R2, R3, R5 and R6 form together : 20 with the C-atoms of the phenyl ring to-which they are bonded, an oxygen-containing 5-, 6- or 7-membered ring, . ~ while R4 preferably represents hydrogen. SE oo

Ina preferred embodiment of the invention Y in the compounds according to the invention is a chain —(CH,),-Z-(CH,)o-, wherein Z is selected from the residues cyclopentyl, cyclohexyl and cycloheptyl, and wherein p and o are independently of each other selected from 0,1 and 2 and together provide a maximum value of 2 or 1 or are both 0.

In the compounds of general formula | Y is preferably a hydrocarbon chain of formula - (CH2),- with g=2, 3, 4 or 5, most particularly preferably with n=4 or 5. X thus most particularly preferably represents a group of general formula X2° :

0 R2 R3

Aah N R4 Formula X2

R6 R5 in which n has the value 4 or 5 and the substituents R2, R3, R4, R5, R6 and R7 have the significance described in more detail above.

In one embodiment of the invention at least one of the substituents R2, R3, R56 and R6 is a halogen atom, in particular fluorine or chlorine, while R4 preferably represents hydrogen.

In another preferred embodiment at least one of the two residues R2 and R3 stands for a substituent other than hydrogen, in particular for alkyl, phenyl, alkyloxy, phenylalkyloxy, alkylthio, trifluoromethyl, cyano, a nitro group or a halogen, in particular methyl, methoxy, ethoxy, benzyloxy, methylmercapto, trifluoromethyl, cyano, nitro, fluorine or chlorine, particularly preferably R2 and R3 both being halogens, and most particularly preferably chlorine, while the residues R4, RS and R6 in compounds according to the invention or in formula X1 and formula X2 stand for hydrogen in each case.

In a preferred embodiment of the invention, in particular if the heterocycle is a pyrazolo[1,5-a]pyridine, one of the two substituents R2 or R3 is selected from alkyl, phenyl, alkyloxy, phenylalkyloxy, alkylthio, trifluoromethyl, cyano, a nitro group or a halogen, in particular methyl, methoxy, ethoxy, benzyloxy, methylmercapto, trifluoromethyl, cyano, nitro, fluorine or chlorine, particularly preferably R2 and R3 both being halogens, and most particularly preferably chlorine.

In a further preferred embodiment of the invention in the compounds of general formula two vicinal substituents selected from R2, R3, R5 and R6, and in particular the substituents R2 and R3 together with the phenyl residue, with which they are bonded, form a chromane or dihydrobenzofurane, while R4 preferably represents hydrogen.

A preferred embodiment of the invention concerns compounds of general formula |, wherein:

Wt | Amended page as filed on 23" March 2007

BN -8- | g ~

Co John L. Spicer . : Patent Attorney (a) the two rings A and B of the heteroarene have, in addition to the X group, a maximum of 2 substituents R1 :

KE (b) R7is hydrogen \ (c) Xrepresents a group of general formula X2 o RR R3 ~~.

AO pm

Wa

R6 RS in which n has the value 4 or 5 and (d)R2, R3, R5 and R6 are preferably and in each case independently of each other selected from the group comprising hydroxy, fluorine, chlorine, bromine, oo trifluoromethyl, cyano, amino, carboxy, sulfo, sulfamoyl, unsubstituted or hydroxy “substituted C1-C6 alkyl, unsubstituted or hydroxy substituted C1-C6 alkyloxy, =

E unsubstituted or hydroxy substituted C1-C6 alkylthio; unsubstituted C2-C6 alkinyl, unsubstituted or with fluorine, chlorine or bromine and/or one or more methoxy groups substituted phenoxy, -C(0)-C1-C6 alkyl, wherein the alkyl is unsubstituted or hydroxy substituted, -C(O)-phenyl, phenylalkyl, phenylalkyloxy : or phenylalkyloxycarbonyl, wherein the phenyl is in each case unsubstituted or with fluorine, chlorine or bromine and/or with one or more methoxy groups oo substituted, C1-C6 alkyloxycarbonyl, wherein the alkyl is unsubstituted or - . 20 hydroxy substituted, C1-6 alkylaminosulfonyl, in particular methylaminosulfonyl »! oo and C1-6 alkylsulfonylamino, in particular methanesulfonylamino, or two vicinal oo . residues R2, R3, R5 and R6 together with the C-atoms of the phenyl ring with which they are bonded, form an oxygen-containing 5-, 6- or 7-membered ring; (e) R4 represents hydrogen; oo : : : on condition that, as described in more detail above, certain compounds are 3 excluded as a proviso. : oo :

Examples of indolizine derivatives of general formula | according to the invention are: :

CD, GIy, Ch GR

A A N A 3

N N— Kx N—y XX nN x

R

R _— _N _N

A 2 A N

N—y N— 2X NK (Tp

N

NT X

A N N ~N —N ~N N X (AT

R NN X

R in which: the ring A is in each case saturated or aromatic; the ring-forming C-atoms of rings A and B can in each case be substituted independently of each other with R1;

R, R1 and X have the significance as described in more detail above.

A preferred embodiment of the invention concerns compounds of formula Il 8 1 7 7a — X

AE) Y/ 2 Formula Il 5 3 in which: the indolizine core in positions 1-3 and 5-8, as shown in formula H, apart from the X group can also have one or more, e.g. 1, 2, 3 or 4 further substituents R1, which in each case are selected independently of each other from hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyil, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino;

X is linked to any position 1-3 or 5-8 of the indolizine and represents a group of general formula X1

R2 R3 0 r= N R4 Formula X1 __/

R7

R6 R5 in which:

Y is an unbranched, saturated or unsaturated hydrocarbon chain with 2-5 carbon atoms or a chain —-(CH2),-Z-(CH2),, in which Z is selected from the residues cyclopentyl, cyclohexyl and cycloheptyl, wherein o and p in each case and independently of each other have the value 0, 1, 2 or 3 and wherein the sum of o and p is a maximum of 3;

R2, R3, R4, R5 and R6 are in each case and independently of each other selected from the group comprising hydrogen, hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenylalkyl, phenoxy, phenylalkyloxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, phenylalkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino, wherein two vicinal residues R2, R3, R4, R5 and R6 together with the C-atoms of the phenyl ring to which they are bonded, can form an oxygen-containing 5-, 6- or 7-membered ring; wherein R4 preferably represents hydrogen.

R7 is hydrogen, alkyl or phenylalkyl.

In one embodiment of the invention the heteroarene in formula Il is unsubstituted apart from the X group or carries in positions 1 and/or 2 one or more residues R1, as defined in more detail above, in particular cyano or alkyl, e.g. methyl.

The substituent X is preferably linked with the 1,2 and 3-position of the indolizine (formula

I).

In one embodiment of the invention Y in compounds of general formula Il is a chain — (CH2),-Z-(CH2),, wherein Z is selected from the residues cyclopentyl, cyclohexyl and cycloheptyl and wherein o and p in each case and independently of each other have the value 0,1 or 2 and preferably both together have a maximum value of 2 or 1 or both are 0.

Y is in the compounds of general formula Il preferably a hydrocarbon chain of formula — (CH2)e- with g=2, 3, 4 or 5, most particularly preferably with n=4 or 5. In formula Ii, therefore, X represents particularly preferably a group of general formula X2 o R2 R3 /\

PR N R4 7 \__/ Formula X2

R7 is preferably hydrogen.

In one embodiment of the invention at least one of the substituents R2, R3, R5 and R6 in the compounds of general formula Il is a C1-6 alkyloxy group, e.g. a methoxy or a halogen atom, in particular fluorine or chlorine, while R4 preferably represents hydrogen.

In another preferred embodiment at least one of the two residues R2 and R3 in the compounds of general formula Il stands for a substituent other than hydrogen, in particular for halogen or C1-6 alkyloxy, while the residues R4, R5 and R6 in formula Il in each case stand for hydrogen.

In a preferred embodiment of the invention one of the two substituents R2 or R3 in the compounds of general formula Il is a C1-6 alkyloxy group, in particular methoxy, or a halogen, in particular fluorine or chlorine, particularly preferably R2 and R3 both being halogen, most particularly preferably chlorine.

In a further preferred embodiment of the invention, in the compounds of general formula I two vicinal substituents selected from R2, R3, R5 and R6, and in particular the substituents R2 and R3, together with the phenyl! residue, to which they are bonded, form a chromane or dihydrobenzofurane, while R4 preferably represents hydrogen.

Another preferred embodiment of the invention concerns compounds of formula l1I 4 3 =~ — X / 2

AN Np Formula lll 7 in which: 5 the pyrazolo[1,5-a]pyridine core can in positions 2-7, as shown in formula Ill, apart from the X group, also carry one or more, e.g. 1, 2, 3 or 4 further substituents R1, which are in each case selected independently of each other from hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino;

X is linked with any position 2-7 of the pyrazolo[1,5-a)pyridine and represents a group of general formula X1

R2 R3 0

Ian

N’ N N R4 Formula X1 __/

R7

R6 R5 in which:

Y is an unbranched, saturated or unsaturated hydrocarbon chain with 2-5 carbon atoms or a chain —-(CH2),-Z-(CH2),, in which Z is selected from the residues cyclopentyl, cyclohexyl and cycloheptyl, wherein o and p in each case and independently of each other have the value 0, 1, 2 or 3 and wherein the sum of 0 and p is a maximum of 3;

R2, R3, R4, R5 and R6 are in each case and independently of each other selected from the group comprising hydrogen, hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenylalkyl, phenoxy, phenylalkyloxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, phenylalkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino, wherein two vicinal residues R2, R3, R4, R5 and R6 together with the C-atoms of the phenyl ring, to which these are bonded, can form an oxygen-containing 5-, 6- or 7-membered ring, wherein R4 preferably represents hydrogen;

RY is hydrogen, alkyl or phenylalkyl.

The X group is preferably bonded with positions 2, 5 or 6 of the pyrazolo[1,5-a]pyridine of formula HII.

In one embodiment the pyrazolo[1,5-a}-pyridine core is substituted in at least one of positions 5 or 6. In a preferred embodiment of the invention the pyrazolo[1,5-a]pyridine carries in position 5 a methoxy- or CF;-residue and/or in position 6 a halogen atom, in particular if X is bonded to position 2 of the heteroarene.

In another preferred embodiment the pyrazolo[1,5-a]-pyridine core in the compounds of general formula Ill apart from the mandatory substituent X is unsubstituted, in particular if

X is bonded to positions 5 or 6 of the heteroarene.

Y is in the compounds of general formula Ill preferably a hydrocarbon chain of formula — (CH2),- with g=2, 3, 4 or 5, with quite particular preference with n=4 or 5. In formula Ill the

X group therefore represents particularly preferably a group of general formula X2 0 R2. R3

Pe N R4

Rk \/ Formula X2

R7 is preferably hydrogen.

In one embodiment of the invention at least one of the substituents R2, R3, R5 and R6 in the compounds of general formula lll is an alkyl (in particular methyl), phenyl, alkyloxy (in particular methyloxy and ethyloxy), phenylalkyloxy (in particular phenyloxy), alkylthio (in particular methylthio), trifluoromethyl, cyano or a nitro group or a halogen atom, in particular fluorine or chlorine, while R4 preferably represents hydrogen.

In another preferred embodiment at least one of the two residues R2 and R3 in the compounds of general formula lil stands for a substituent other than hydrogen, in particular for halogen, alkyl (in particular methyl), phenyl, alkyloxy (in particular methyloxy and ethyloxy), phenylalkyloxy (in particular benzyloxy), alkylthio (in particular methyithio), trifluoromethyl, cyano or nitro, while residues R4, R5 and R6 in each case stand for hydrogen.

In a preferred embodiment of the invention R4 is hydrogen and one of the two substituents

R2 or R3 in the compounds of general formula Ill is a halogen, alkyl (in particular methyl), phenyl, alkyloxy (in particular methyloxy and ethyloxy), phenylalkyloxy (in particular benzyloxy), alkylthio (in particular methylthio), trifluoromethyl, cyano or nitro, in particular fluorine or chlorine, particularly preferably R2 and R3 are both halogen or alkyl, most particularly preferably chlorine or methyl.

In one embodiment of the invention R2 in the compounds of general formula Ill stands for a C1-6 alkyloxy group, in particular for methoxy, provided that (a) at least one of the substituents R3, R5, R6 and R7 represents a residue other than hydrogen and/or (b) the pyrazolo[1,5-a]pyridine core is substituted with at least one substituent R1.

In another embodiment of the invention R2 is not a methoxy. In another embodiment of the invention R2 in the compounds of general formula lll is not an alkyloxy.

In a further embodiment of the invention in the compounds of general formula lil two vicinal substituents selected from R2, R3, R5 and R6, and in particular substituents R2 and R3 together with the phenyl residue to which they are bonded, form a chromane or dihydrobenzofurane.

A further preferred embodiment of the invention comprises compounds of general formula

Iv,

4 3 —\_-X 6 N 7 in which: the tetrahydropyrazolo[1,5-a]pyridine core can in positions 2-7 as shown in formula IV, 5 apart from the X group, also carry one or more, e.g. 1, 2, 3 or 4 additional substituents R1, which are in each case selected independently of each other from hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkyicarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino;

X is preferably linked to position 2 or 3 of the tetrahydropyrazolo[1,5-a]pyridine and represents a group of general formula X1 o R2 R3

Asp ! . _/

R6 R5 in which:

Y is an unbranched, saturated or unsaturated hydrocarbon chain with 2-5 carbon atoms or a chain —(CH2),-Z-(CH2),, in which Z is selected from the residues cyclopentyl, cyclohexyl and cycloheptyl, wherein o and p in each case and independently of each other have the value 0, 1, 2 or 3 and wherein the sum of 0 and p is a maximum of 3;

R2, R3, R4, R5 and R6 are in each case and independently of each other selected from the group comprising hydrogen, hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenylalkyl, phenoxy, phenylalkyloxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, phenylalkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino, wherein two vicinal residues R2, R3, R4, R5 and R6 together with the C-atoms of the phenyl ring to which they are bonded, can form an oxygen-containing 5-, 6- or 7-membered ring, wherein

R4 preferably represents hydrogen;

R?7 is hydrogen, alkyl or phenylalkyl.

In one embodiment of the invention the heteroarene in formula IV is unsubstituted as far as the X group or carries in positions 5 and/or 6 one or more residues R1, as defined in more detail above, in particular alkyl, e.g. methyl.

Yin the compounds of general formula IV is preferably a hydrocarbon chain of formula - (CH2),- with q=2, 3, 4 or 5, with quite particular preference with n=4 or 5. Most particularly preferably therefore in formula IV, X represents a group of general formula X2 0 R2 R3 /\

MA hey N R4 7 __/ Formula X2

R7 is preferably hydrogen.

In one embodiment of the invention at least one of the substituents R2, R3, R5 and R6 in the compounds of general formula IV is a C1-6 alkyloxy group, in particular methoxy, or a halogen atom, in particular fluorine or chlorine.

In another preferred embodiment at least one of the two residues R2 and R3 in the compounds of general formula IV stands for a substituent other than hydrogen, in particular for halogen or C1-C6 alkyloxy, while the residues R4, R5 and R6 in each case stand for hydrogen.

In a preferred embodiment of the invention one of the two substituents R2 or R3 in the compounds of general formula IV is a C1-6 alkyloxy group, in particular methoxy or halogen, in particular fluorine or chlorine, particularly preferably R2 and R3 are both halogen, with quite particular preference chlorine, while R4 preferably represents hydrogen. in a further embodiment of the invention in the compounds of general formula IV two vicinal substituents selected from R2, R3, R5 and R6, and in particular the substituents R2 and R3 together with the phenyl residue, to which they are bonded, form a chromane or dihydrobenzofurane, while R4 preferably represents hydrogen.

Another preferred embodiment of the invention concerns compounds of formula V 8 1 7 A _-X

SAT

5 3 in which: the tetrahydroindolizine core can in positions 1-3 and 5-8, as shown in formula V, apart from the X group, also carry one or more, e.g. 1, 2, 3 or 4 additional substituents R1, which in each case are selected independently of each other from hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenyicarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfony! and alkylsulfonylamino;

X is linked with any position 1-3 of the tetrahydroindolizine and represents a group of general formula X1

R2 R3 0

JP NACE N R4 Formula X1 __/

R7

R6 RS in which:

Y is an unbranched, saturated or unsaturated hydrocarbon chain with 2-5 carbon atoms or a chain —(CH2),-Z-(CH2),, in which Z is selected from the residues cyclopentyl, cyclohexyl and cycloheptyl, wherein 0 and p in each case and independently of each other have the value 0, 1, 2 or 3 and wherein the sum of 0 and p is a maximum of 3;

R4 preferably represents hydrogen;

R7 is hydrogen, alkyl or phenylalkyl. in one embodiment of the invention the heteroarene in formula V is unsubstituted as far as the X group.

The substituent X is preferably linked with the 1,2 and 3-positions of the tetrahydroindolizine (formula V) and particularly preferably with position 2.

Y is in the compounds of general formula V preferably a hydrocarbon chain of formula — (CH2),- with g=2, 3, 4 or 5, with quite particular preference with n=4 or 5. X thus represents in formula V particularly preferably a group of general formula X2 0 R2 R3

PPS Wan nd N R4 | Formula X2 \__/

R7

RYT is preferably hydrogen.

In one embodiment of the invention at least one of the substituents R2, R3, R5 and R6 in the compounds of general formula V is a C1-6 alkyloxy group, e.g. a methoxy or a halogen atom, in particular fluorine or chlorine, while R4 preferably represents hydrogen.

Another preferred embodiment of the invention concerns compounds of formula VI 8 772” =N X 2

INQ Wz Formula VI 5 3 in which: the heteroarene core can in positions 2-3 and 5-8, as shown in formula VI, apart from the

X group, also carry one or more, e.g. 1, 2, 3 or 4 additional substituents R1, which are in each case selected independently of each other from hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino;

X is linked with any position 2-3 or 5-8 of the heteroarene and represents a group of general formula X1

R2 R3 i

JG N R4 | Formula X1 ) _/

R7

R6 RS in which:

Y is an unbranched, saturated or unsaturated hydrocarbon chain with 2-5 carbon atoms or a chain —(CH2),-Z-(CH2),, in which Z is selected from the residues cyclopentyl, cyclohexyl and cycloheptyl, wherein 0 and p in each case and independently of each other have the value 0, 1, 2 or 3 and wherein the sum of o and p is a maximum of 3;

R4 preferably represents hydrogen;

R7 is hydrogen, alkyl or phenylalkyl.

In one embodiment of the invention the heteroarene in formula Vl is unsubstituted apart from the X group or carries in the 2- or 6-position a residue R1 as defined in more detail above, in particular alkyl, e.g. methyl, or halogen.

The substituent X is preferably linked with the 2,3 or 6-position of the heteroarene (formula

VI).

Ys in the compounds of general formula VI preferably a hydrocarbon chain of formula — (CH2),- with g=2, 3, 4 or 5, most particularly preferably with n=4 or 5. X thus represents in formula VI particularly preferably a group of general formula X2 0 R2 R3

Ahm gg

R7 is preferably hydrogen.

In one embodiment of the invention at least one of the substituents R2, R3, R5 and R6 in the compounds of general formula VI is a methoxy group or a halogen atom, in particular fluorine or chlorine, while R4 preferably represents hydrogen.

Another preferred embodiment of the invention concerns compounds of formula VII 72" _N X e Formula VII in which: 5 the heteroarene core can in positions 2 and 5-8, as shown in formula VII, apart from the X group, also carry one or more, e.g. 1, 2, 3 or 4 additional substituents R1, which are in each case selected independently of each other from hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino;

X is linked with any position 2 or 5-8 of the heteroarene and represents a group of general formula X1

R2 R3 oO

J NY N R4 Formula X1 __/

R7

R6 R5 in which:

R2, R3, R4, R5 and R6 are in each case and independently of each other selected from the group comprising hydrogen, hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenylalkyl, phenoxy, phenylalkyloxy, halogen, trifluoromethyl, alkylcarbonyi, phenylcarbonyl, alkyloxycarbonyl, phenylalkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino, wherein two vicinal residues R2, R3, R4, R5 and R6 together with the C-atoms of the phenyl ring to which they are bonded, can form an oxygen-containing 5-, 6- or 7-membered ring, wherein

R4 preferably represents hydrogen;

RY is hydrogen, alkyl or phenylalkyl.

In one embodiment of the invention the heteroarene in formula VII is unsubstituted as far as the X group.

The substituent X is preferably linked to the 2-position of the heteroarene (formula Vi).

Y is in the compounds of general formula Vii preferably a hydrocarbon chain of formula — (CH2)4- with g=2, 3, 4 or 5, most particularly preferably with n=4 or 5. X thus represents in formula VII particularly preferably a group of general formula X2 0 R2 R3

AR

R7 is preferably hydrogen.

In one embodiment of the invention at least one of the substituents R2, R3, R5 and R6 in the compounds of general formula Vi is a halogen atom, in particular fluorine or chlorine, while R4 preferably represents hydrogen.

-23- . BE

A preferred embodiment of the invention concerns compounds of formula Vili 4 3 2 Formula Vill

IN in which: the heteroarene core can in positions 2-6, as shown in formula VIII, apart from the X group, also carry one or more, e.g. 1, 2, 3 or 4 additional substituents R1, which are in each case selected independently of each other from hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyi, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsuifonylamino;

X is linked with any position 2-6 of the heteroarene and represents a group of general formula X1

R2 R3 it

J NACE N R4 Formula X1 \__/

R7

R6 R5 in which:

Y is an unbranched, saturated or unsaturated hydrocarbon chain with 2-5 carbon atoms or a chain —(CH2),-Z-(CH2),, in which Z is selected from the residues cyclopentyl, cyclohexyl and cycloheptyl, wherein o and p in each case and independently of each other have the value 0, 1, 2 or 3 and wherein the sum of o and p is a maximum of 3;

R2, R3, R4, R5 and R6 are in each case and independently of each other selected from the group comprising hydrogen, hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenylaikyl, phenoxy, phenylalkyloxy, halogen, trifluoromethyl, alkylcarbonyl,

phenylcarbonyl, alkyloxycarbonyl, phenylalkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonytamino, alkylaminosulfonyl and alkylsulfonylamino, wherein two vicinal residues R2, R3, R4, R5 and R6 together with the C-atoms of the phenyl ring to which they are bonded, can form an oxygen-containing 5-, 6- or 7-membered ring, wherein

R4 preferably represents hydrogen;

R7 is hydrogen, alkyl or phenylalkyl.

The substituent X is preferably linked to the 2-position of the heteroarene (formula Vill).

Y is in the compounds of general formula VII preferably a hydrocarbon chain of formula — (CH2)- with g=2, 3, 4 or 5, most particularly preferably with n=4 or 5. X thus represents in formula VIII particularly preferably a group of general formula X2 0 R2 R3 7 \ / Formula X2

R6 RS in which n has the value 4 or 5 and the substituents R2, R3, R4, R5, R6 and R7 have the significance described in more detail above.

R7 is preferably hydrogen.

In one embodiment of the invention at least one of the substituents R2, R3, R5 and R6 in the compounds of general formula Vil is a halogen atom, in particular fluorine or chlorine, while R4 preferably represents hydrogen.

A preferred embodiment of the invention concerns compounds of formula IX 8 1.2 =N__X 2

AS 7 Formula IX

N 3 in which: the heteroarene core can in positions 2-3 and 6-8, as shown in formula IX, apart from the X group, also carry one or more, e.g. 1, 2, 3 or 4 additional substituents R1, which are in each case selected independently of each other from hydroxy, alkyl, alkyloxy, alkyithio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoy!, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino;

X is linked with any position 2-3 or 6-8 of the heteroarene and represents a group of general formula X1 o R2 R3

Ap lpm nd

R6 R5 in which:

R2, R3, R4, R5 and R6 are in each case and independently of each other selected from the group comprising hydrogen, hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenylalkyl, phenoxy, phenylalkyloxy, halogen, trifluoromethyl, alkyicarbonyl, phenylcarbonyl, alkyloxycarbonyi, phenylalkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosuifonyl and alkylsuifonylamino, wherein two vicinal residues R2, R3, R4, R5 and R6 together with the C-atoms of the phenyl ring to which they are bonded, can form an oxygen-containing 5-, 6- or 7-membered ring, wherein

R4 preferably represents hydrogen;

R7 is hydrogen, alkyl or phenylalkyl.

In one embodiment of the invention the heteroarene in formula IX is unsubstituted as far as the X group or carries in position 2 and/or position 6 a residue R1 as defined in more detail above, in particular phenyl or halogen.

The substituent X is preferably linked to the 2- or 3-position of the heteroarene (formula 1X).

Y is in the compounds of general formula 1X preferably a hydrocarbon chain of formula — (CH2),- with g=2, 3, 4 or 5, most particularly preferably with n=4 or 5. X thus represents in formula 1X particularly preferably a group of general formula X2 0 R2 R3 /\

PW N R4

Lo 4 Formula X2

R7 is preferably hydrogen.

In one embodiment of the invention at least one of the substituents R2, R3, R5 and R6 in the compounds of general formula IX is a methoxy residue or a halogen atom, in particular fluorine or chlorine, while R4 preferably represents hydrogen.

The invention also concerns physiologically acceptable salts of the compounds according to the invention. Examples of such salts are described in the following definitions.

The person skilled in the art will also realise that depending on the choice of substituents geometrical isomers and/or optically active compounds can result. In this case both the isomers and racemates and also the respective pure enantiomeric or possibly diastereomeric forms are the subject-matter of the present invention.

The substituents mentioned in the description and in the attached claims include in particular the following groups.

“Alkyl” can be a branched or unbranched alkyl group, which preferably has between 1 and 10 C-atoms, particularly preferably between 1 and 6 C-atoms (“C1-C6 alkyl”) and most particularly preferably 1, 2 or 3 C-atoms. “C1-C6 alkyl" includes, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, s-butyl, t-butyl, n-pentyl, iso-pentyl, neopentyl, t-

pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl and n-hexyl.

“Alkyl” can also be cyclical or contain a cyclical component, wherein cycles with 3-7 C- atoms are preferred, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl. “Alkyl” is preferably not cyclical and contains no cyclical component.

Alkyl groups can also be substituted with one or more substituents, in particular with hydroxy or amine. “Alkyl” is preferable unsubstituted or substituted with hydroxy.

“Alkenyl” and “alkinyl” have at least one double or triple bond.

They can be branched or unbranched and preferably have between 2 and 6 C-atoms.

Alkenyls or alkinyls are preferably bonded to the heteroarene- or phenyl ring of the scaffold of the compound in such a way that the double or triple bond is conjugated with the aromatic ring.

Alkenyl and alkinyl can also be substituted with one or more substituents, preferably with phenyl, wherein the phenyl group then is preferably located at C-atom 2 (if the alkenyl or alkinyl is bonded via C-atom 1 to the heteroarene- or phenyl ring of the scaffold). The alkenyls or alkinyls are preferably unsubstituted.

“Alkyloxy” is the -O-alkyl group, in which the alkyl is preferably selected from the groups specified above for “alkyl”. “Alkyloxy” is preferably a C1-C6-alkyloxy group, particularly preferably methoxy.

“Alkylthio” can also be referred to as “alkylmercapto” and is the —S-alky! group, in which alkyl is preferably selected from the groups specified for “alkyl” above. “Alkyithio” is preferably a C1-C6-alkyl-S-group.

“Alkylaminosulfonyl” includes the —SO,-NH-alkyl and —SO.-N-dialkyl groups, in which alkyl is preferably selected from the groups specified above for “alkyl”. “Alkyl” in the “alkylaminosulfonyl” is preferably a C1-C6-alkyl group. “Alkylaminosulfonyl® examples include methylaminosulfonyl, N,N-dimethylaminosulfonyl and butylaminosulfonyt.

“Alkylsulfonylamino” is the —~NH-SO_-alkyl group, in which alkyl is preferably selected from the groups specified above for “alkyl”. “Alkylsulfonylamino” is preferably a C1-C6- alkylsulfonylamino group, e.g. methanesulfonylamino. “Phenyl” is preferably unsubstituted, but can if necessary be independently substituted one or more times, e.g. with alkoxy, alkyl, trifluoromethyl or halogen. “Phenylalkyl” is the —alkyl-phenyl group, wherein phenyl and alkyl have the significance as defined above.

Phenyl alkyl includes for example phenylethyl and benzyl and is preferably benzyl. “Phenoxy” is the -O-phenyl group, in which phenyl has the significance defined in more detail above.

“Phenylalkyloxy” is the phenylalkyl-O- group, in which phenylalkyl has the significance defined in more detail above. “Alkylcarbonyl” includes the -C(O)-alkyl group, in which alkyl is preferably selected from the groups specified above for “alkyl”, and is particularly preferably -C(O)-C1-C6-alkyl.

“Alkylcarbonyl” is preferably acetyl, propionyl or butyryl. “Phenylcarbonyl” is -C(O)-phenyl, in which phenyl has the significance as defined in more detail above

“Alkyloxycarbonyl” is the -C(O)-O-alkyl group, in which alkyl is preferably selected from the groups specified above for “alkyl”. “Alkoxycarbonyl” is preferably a (C1-C6- alkyl)oxycarbonyl group. “Phenylalkyloxycarbonyl” is the phenylalkyl-O-C(O)- group, in which phenylalky! has the significance defined in more detail above. “Halogen” includes fluorine, chlorine, bromine and iodine, and is preferably fluorine, chlorine or bromine.

“Sulfamoyl” includes the —=SO,-NH; group.

“Sulfonylamino” includes the ~NH-SO,H group. “Physiologically acceptable salts” include non-toxic addition salts of a base, in particular a compound of formulae (I) to (IV) in the form of the free base, with organic or inorganic acids. Examples of inorganic acids include HCI, HBr, sulphuric acid and phosphoric acid.

Organic acids include acetic acid, propionic acid, pyruvic acid, butyric acid, a-, f- or y- hydroxbutyric acid, valeric acid, hydroxyvaleric acid, caproic acid, hydroxycaproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, glycolic acid, lactic acid, D-glucuronic acid, L-glucoronic acid, D-galacturonic acid, glycine, benzoic acid, hydroxybenzoic acid, gallic acid, salicylic acid, vanillic acid, coumarinic acid, caffeic acid, hippuric acid, orotic acid, L-tartaric acid, D-tartaric acid, D,L-tartaric acid, meso-tartaric acid, fumaric acid, L-malic acid, D-malic acid, D,L-malic acid, oxalic acid, malonic acid, succinic acid, maleic acid, oxalic acid, glutaric acid, hydroxyglutaric acid, ketoglutaric acid, adipinic acid, ketoadipinic acid, pimelic acid, glutamic acid, aspartic acid, phthalic acid, propanetricarboxylic acid, citric acid, isocitric acid, methane sulfonic acid, toluene sulfonic acid, benzene sulfonic acid, camphor sulfonic acid, embonic acid and trifluoromethane sulfonic acid.

The following compounds represent specific embodiments of the compounds according to the invention: (B69): N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butylindolizin-1-ylcarbamide (B1): N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butylindolizin-2-ylcarbamide (B2): N-4-(4-(3-chloro-2-methoxyphenyl)piperazin-1-yhbutylindolizin-2-ylcarbamide (B3): N-4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butylindoiizin-2-ylcarbamide (B4): N-4-(4-(2,3-difluorophenyl)piperazin-1-yl)butylindolizin-2-ylcarbamide (B5): N-4-(4-(2,3-dihydrobenzofuran-7-yl)piperazin-1-yi)butylindolizin-2-ylcarbamide (B49): N-4-(4-(chroman-8-yl)piperazin-1-yl)butylindolizin-2-ylcarbamide (B70): N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-5,6,7,8-tetrahydroindolizin-2- ylcarbamide (B71): N-4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butyl-5,6,7,8-tetrahydroindolizin-2- ylcarbamide (B72): N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-1-cyano-2-methylindolizin-3- ylcarbamide (BB): N-2-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethylpyrazolo[1,5-a]pyridin-2-ylcarbamide

(B7): N-3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propylpyrazolo[1,5-alpyridin-2- ylcarbamide (B73): N-4-(4-phenylpiperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2-ylcarbamide (B74): N-4-(4-(2-methylphenyl)piperazin-1-yl)butylpyrazolo[1,5-alpyridin-2-ylcarbamide (B75): N-4-(4-(2-biphenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2-ylcarbamide (B76): N-4-(4-(2-ethoxyphenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2-ylcarbamide (B77): N-4-(4-(2-benzyloxyphenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2-ylcarbamide (B78): N-4-(4-(2-methylmercaptophenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2- ylcarbamide (B79): N-4-(4-(2-fluorphenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2-ylcarbamide (B80): N-4-(4-(2-trifluoromethylphenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2- ylcarbamide (B81): N-4-(4-(2-cyanophenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2-ylcarbamide (B82): N-4-(4-(2-nitrophenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2-ylcarbamide (B83): N-4-(4-(4-methoxyphenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2-ylcarbamide (B84): N-4-(4-(3-chloro-2-methoxyphenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2- ylcarbamide (B8): N-4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2-ylcarbamide (B85): N-4-(4-(2,3-dimethylphenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2-ylcarbamide (B86): N-4-(4-(2,3-dihydrobenzofuran-7-yl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2- ylcarbamide (B87): N-4-(4-(chroman-8-yl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2-ylcarbamide (B88): N-4-(4-(2,4-dimethoxyphenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2- ylcarbamide (B10): N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-3-bromopyrazolo[1,5-a]pyridin-2- ylcarbamide (B11): N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-3-chloropyrazolo[1,5-a]pyridin-2- ylcarbamide (B50): N-4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butyl-5-methoxypyrazolo[1,5-a]pyridin-2- ylcarbamide (B51): N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-5-methoxypyrazolo[1,5-a]pyridin-2- ylcarbamide (B12): N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-5-methylpyrazolo[1,5-a]pyridin-2- ylcarbamide (B52): N-4-(4-(2,3-dichliorophenyl)piperazin-1-yl)butyl-5-trifluoromethylpyrazolo{1,5- a)pyridin-2-ylcarbamide

Claims

1. Compounds of general formula |, Q 7 Q; —% Hos Qs NC a in which: A is a saturated or aromatic 6-membered ring; B is an aromatic 5-membered ring; the heteroarene formed by A+B has in total a maximum of three ring-forming N- atom and precisely one X group as substituents; Q1, Q2 and Q3 are in each case and independently of each other N, CH or C- R1; Q4 is N-R, CH-R1’ or C-R1R1’; Q5, Q6 and Q7 are independently of each other CH-R1' or C-R1R1’; R1 is in each case selected from the group comprising hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino; R1' is absent, if ring A is aromatic or is hydrogen, if ring A is saturated; R is absent, if ring A is aromatic or is selected from among hydrogen, alkyl, phenyl, alkyicarbonyl, phenyicarbonyl, phenylalkyl and phenylisulfonyl, if ring A is saturated;

X is a group of general formula X1 bonded to a C-atom of an aromatic ring A or B R2 R3 i J NP N R4 | Formula X1 __/ R7 R6 R5 wherein: Y is an unbranched, saturated or unsaturated hydrocarbon chain with 2-5 carbon atoms or a chain —(CH2),-Z-(CH2),, in which Z is selected from the residues cyclopentyl, cyclohexyl and cycloheptyl, wherein o and p in each case and independently of each other have the value 0, 1, 2 or 3 and wherein the sum of o and p is a maximum of 3;

R2, R3, R4, R5 and R6 are in each case and independently of each other selected from the group comprising hydrogen, hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenylalkyl, phenoxy, phenylalkyloxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, phenylalkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl,

sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino, wherein two vicinal residues R2, R3, R4, R5 and R6 together with the C-atoms of the phenyl ring to which they are bonded, can form an oxygen-containing 5-, 6- or 7-membered ring;

R7 is hydrogen, alkyl or phenylalkyl; in the form of the free base, their physiologically acceptable salts and possible enatiomers and diastereomers,

with the proviso of exclusion of

(a) compounds in which the heterocycle is a pyrazolo[1,5-a]pyridine, in particular if this carries as the sole substituent the X group, but no R1 substituent, wherein for X: R2 = methoxy; R3, R4, R5, R6 and R7 are in each case hydrogen and (i) Y = ethylene, n-propylene or n-butylene or (ii) Y = n-pentylene and X is in 2- or 3-position linked with the pyrazolo[1,5-a] pyridine core (b) The compound N-4-(4-(2-chlorophenyl)piperazin-1-yl)butyl-7- methylpyrazolo[1,5-a]pyridin-3-ylcarbamide.

2. Compounds according to one of the preceding claims [sic], selected from the group comprising — = N NE nN” TNX N R — Ky — N NK x N- Kx ge — A R N dT GI TT Fo Law ; N X R wherein: the ring A is in each case saturated or aromatic; the ring-forming C-atoms of rings A and B can in each case and independently of each other be substituted with R1,; R, R1 and X have the significance as described in claim 1.

3. Compounds according to either one of the preceding claims in which Y represents a group —(CHg)n- with n= 4 or 5.

4. Compounds according to any one of the preceding claims, wherein R7 is hydrogen.

5. Compounds according to any one of the preceding claims of general formula Il 8 1 7 wz 2 ox N / Formula 5 3 in which: the substituent X is linked with any position 1-3 and 5-8 of the indolizine and represents a group of general formula X1 as described in the preceding claims; the indolizine can in positions 1-3 and 5-8 apart from X also carry one or more additional substituents R1, selected from among hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino.

6. Compounds according to claim 5, wherein X is linked to the 1-, 2-, or 3-position of the indolizine.

7. Compounds according to either one of claims 5-6, wherein X represents a group of general formula X2 0 R2 R3 PR N R4 Lo R6 RS in which: nis 4 orb; R2, R3, R4, R5, R6 and R7 are residues, as described in claim 1.

8. Compounds according to any one of claims 5-7, wherein at least one of the two substituents R2 and R3 represents a halogen atom or a methoxy group or wherein R2 and R3 together with the phenyl residue, to which they are bonded form a chromane or dihydrobenzofurane, while R4 represents hydrogen.

9. Compounds according to any one of claims 1-4, of general formula III 4 3 5 ZZ N= XK 2 7 in which: the substituent X is linked with any position 2-7 of the pyrazolo[1,5-a]pyridine and represents a group of general formula X1, as described in any one of claims 1, 3 or 4; the pyrazolo[1,5-a]pyridine in positions 2-7, apart from X, can also carry one or more additional substituents R1, selected from among hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino.

10. Compounds according to claim 9, wherein the X group is linked to positions 2, 5 or 6 of the pyrazolo[1,5-a]pyridine.

11. Compounds according to either one of claims 9-10, wherein the pyrazolo[1,5-a]pyridine in position 5 carries a methoxy or trifluoromethyl residue and/or in position 6 a halogen atom.

12. Compounds according to any one of claims 9-11, wherein X represents a group of general formula X2 0 R2 R3 PR Or I R6 R5 in which: nis 4 or 5; R2, R3, R4, R5, R6 and R7 are residues, as described in claim 1.

13. Compounds according to any one of claims 9-12, wherein R4 represents hydrogen and the substituents R2 and R3 are selected from the group comprising halogen, alkyl, alkyloxy, phenylalkyloxy, alkylthio, trifluoromethyl, cyano or nitro or wherein the two substituents R2 and R3 together form a chromane or dihydrobenzofurane ring.

14. Compounds according to any one of claims 1-4 of general formula IV 4 3 5 _—\_-X 7)? 7 in which: the substituent X is linked to positions 2 or 3 of the 4,5,6,7- tetrahydropyrazolo[1,5-a]pyridine and represents a group of general formula X1 as described in one of claims 1, 3 or 4; the 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine can in positions 2-7 apart from the X group also carry one or more additional substituents R1, selected from among hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano,

nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino.

15. Compounds according to either one of claims 13-14, wherein X represents a group of general formula X2 0 R2 R3 /\ AT / Formula X2 R6 R5 in which: nis4orb5; R2, R3, R4, R5, R6 and R7 are residues, as described in claim 1.

16. Compounds according to either one of claims14-15, wherein R4 represents hydrogen and wherein at least one of the substituents R2 and R3 is a halogen atom or a methoxy group.

17. Compounds according to any one of claims 1-4 of general formula V 8 1 7 — X 2 Ln 5 3 in which: the substituent X is linked with positions 1, 2 or 3 of the 5,6,7,8- tetrahydroindolizine and represents a group of general formula X1 as described in any one of claims 1, 3 or 4; the 5,6,7,8-tetrahydroindolizine can in positions 1-3 and 5-8 apart from the X group also carry one or more additional substituents R1, selected from among hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen,

trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino.

18. Compounds according to claim 17, wherein X represents a group of general formula X2 o R2 R3 /\ ta \__/ Formula X2 R6 RS in which: nis 4 or5; R2, R3, R4, R5, R6 and R7 are residues, as described in claim 1.

19. Compounds according to either one of claims 17-18, wherein R4 represents hydrogen and at least one of the substituents R2 and R3 is a halogen atom or a methoxy group.

20. Compounds according to any one of claims 1-4 of general formula VI 8 7727 _N X 2 AZ / Formula VI 5 3 in which: the substituent X is linked with positions 2-3 or 5-8 of the heteroarene core and represents a group of general formula X1 as described in any one of claims 1, 3 or 4; the heteroarene core of formula VI can in positions 2-3 and 5-8 apart from the X group also carry one or more additional substituents R1, selected from among hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino.

21. Compounds according to claim 20, wherein X represents a group of general formula X2 0 R2 R3 LT R6 R5 in which: nis 4 or 5; R2, R3, R4, R5, R6 and R7 are residues, as described in claim 1.

22. Compounds according to either one of claims 20-21, wherein R4 represents hydrogen and at least one of the substituents R2 and R3 is a halogen atom or a methoxy group.

23. Compounds according to any one of claims 1-4 of general formula Vii 8 ged 7? Formula VII AN Nn 5 in which: the substituent X is linked with positions 2 or 5-8 of the heteroarene core and represents a group of general formula X1 as described in any one of claims 1, 3 or 4;

the heteroarene core of formula VII can in positions 2 and 5-8 apart from the X group also carry one or more additional substituents R1, selected from among hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenyicarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, suifonylamino, alkylaminosuifonyl and alkylsulfonylamino.

24. Compounds according to claim 23, wherein X represents a group of general formula X2 0 R2 R3 /\

J. N R4 7 __/ Formula X2 R6 R5 in which: nis 4 orb; R2, R3, R4, R5, R6 and R7 are residues, as described in claim 1.

25. Compounds according to either one of claims 23-24, wherein R4 represents hydrogen and at least one of the substituents R2 and R3 is a halogen atom.

26. Compounds according to any one of claims 1-4 of general formula Vii 4 3

5.27 —_ X / 2 6 XN Formula VIII in which: the substituent X is linked with positions 2-6 of the heteroarene core and represents a group of general formula X1 as described in any one of claims 1, 3 or 4,

the heteroarene core of formula VIII can in positions 2-6 apart from the X group also carry one or more additional substituents R1, selected from among hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsulfonylamino.

27. Compounds according to claim 26, wherein X represents a group of general formula X2 Io) R2 R3 7 \__/ Formula X2 R6 RS in which: nis 4 orb; R2, R3, R4, R5, R6 and R7 are residues, as described in claim 1.

28. Compounds according to either one of claims 26-27, wherein R4 represents hydrogen and at least one of the substituents R2 and R3 is a halogen atom.

29. Compounds according to any one of claims 1-4 of general formula IX 8 72 —N X 2 ex N Y Formula IX N 3 in which: the substituent X is linked with positions 2-3 and 6-8 of the heteroarene core and represents a group of general formula X1 as described in any one of claims 1, 3 or 4;

the heteroarene core of formula IX can in positions 2-3 and 6-8 apart from the X group also carry one or more additional substituents R1, selected from among hydroxy, alkyl, alkyloxy, alkylthio, alkenyl, alkinyl, phenyl, phenoxy, halogen, trifluoromethyl, alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, cyano, nitro, amino, carboxy, sulfo, sulfamoyl, sulfonylamino, alkylaminosulfonyl and alkylsuifonylamino.

30. Compounds according to claim 29, wherein X represents a group of general formula X2 o R2 R3 Abn LT R6 RS in which: nis 4 or 5; R2, R3, R4, R5, R6 and R7 are residues, as described in claim 1.

31. Compounds according to either one of claims 29-30, wherein R4 represents hydrogen and at least one of the substituents R2 and R3 is a methoxy residue or a halogen atom.

32. Compound, selected from among N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butylindolizin-1-ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butylindolizin-2-ylcarbamide N-4-(4-(3-chloro-2-methoxyphenyl)piperazin-1-yl)butylindolizin-2-ylcarbamide N-4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butylindolizin-2-yicarbamide N-4-(4-(2,3-difluorophenyl)piperazin-1 -yl)butylindolizin-2-yicarbamide N-4-(4-(2,3-dihydrobenzofuran-7-yl)piperazin-1-yl)butylindolizin-2-ylcarbamide N-4-(4-(chroman-8-yl)piperazin-1-yl)butylindolizin-2-ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-5,6,7,8-tetrahydroindolizin-2- yicarbamide N-4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butyl-5,6,7,8-tetrahydroindolizin-2- ylcarbamide

N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyi-1 -cyano-2-methylindolizin-3- ylcarbamide N-2-(4-(2,3-dichlorophenyl)piperazin-1 -yl)ethylpyrazolo[1,5-a]pyridin-2- ylcarbamide N-3-(4-(2,3-dichlorophenyl)piperazin-1 -yl)propylpyrazolo[1,5-a]pyridin-2-

ylcarbamide N-4-(4-phenylpiperazin-1-yl)butylpyrazolo[1 ,5-a)pyridin-2-ylcarbamide N-4-(4-(2-methylphenyl)piperazin-1-yl)butylpyrazoio[1 ,5-a]pyridin-2- ylcarbamide

N-4-(4-(2-biphenyl)piperazin-1-yl)butylpyrazolo[1 ,5-a]pyridin-2-ylcarbamide N-4-(4-(2-ethoxyphenyl)piperazin-1-yi)butylpyrazolof 1,5-a)pyridin-2- ylcarbamide N-4-(4-(2-benzyloxyphenyi)piperazin-1-yl)butylpyrazolo[1 ,5-a]pyridin-2- ylcarbamide

N-4-(4-(2-methylmercaptophenyl)piperazin-1 -yl)butyipyrazolo[1,5-a]pyridin-2- ylcarbamide N-4-(4-(2-fluorophenyl)piperazin-1-yl)butylpyrazolo[1 ,5-a]pyridin-2-ylcarbamide N-4-(4-(2-trifluoromethylphenyl)piperazin-1 -yl)butylpyrazolo[1,5-a]pyridin-2- ylcarbamide

N-4-(4-(2-cyanophenyl)piperazin-1-yl)butylpyrazolo[1 ,5-a)pyridin-2-ylcarbamide N-4-(4-(2-nitrophenyl)piperazin-1-yl)butylpyrazolo[1 ,5-a)pyridin-2-ylcarbamide N-4-(4-(4-methoxyphenyl)piperazin-1-yl)butylpyrazolo[1 ,5-alpyridin-2- ylcarbamide N-4-(4-(3-chloro-2-methoxyphenyl)piperazin-1 -yl)butylpyrazolo[1,5-a]pyridin-2-

ylcarbamide N-4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butylpyrazolo[1 ,5-a]pyridin-2- ylcarbamide N-4-(4-(2,3-dimethylphenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2- ylcarbamide

N-4-(4-(2,3-dihydrobenzofuran-7-yl)piperazin-1 -yl)butylpyrazolo[1,5-a]pyridin-2- ylcarbamide N-4-(4-(chroman-8-yl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-2-ylcarbamide N-4-(4-(2,4-dimethoxyphenyl)piperazin-1-yl)butylpyrazoio[1 ,5-a]pyridin-2- ylcarbamide

N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-3-bromopyrazolo[1 ,5-alpyridin-2- ylcarbamide

N-4-(4-(2-methoxyphenyl)piperazin-1 -yl)butyl-3-chloropyrazolo[1,5-a]pyridin-2- ylcarbamide N-4-(4-(2,3-dichiorophenyl)piperazin-1 -yl)butyl-5-methoxypyrazolo[1,5- a)pyridin-2-ylcarbamide

N-4-(4-(2-methoxyphenyl)piperazin-1 -yl)butyl-5-methoxypyrazolo[1,5-a]pyridin- 2-ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1-yl )butyl-5-methylpyrazolo[1,5-a]pyridin-2- ylcarbamide N-4-(4-(2,3-dichlorophenyl)piperazin-1 -yl)butyl-5-trifluoromethylpyrazolo[1,5-

ajpyridin-2-ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1 -yl)butyl-5-trifluoromethylpyrazolo[1,5- a)pyridin-2-ylcarbamide N-4-(4-(2,3-dichlorophenyl)piperazin-1 -yl)butyl-6-bromopyrazolo[1,5-alpyridin- 2-ylcarbamide

N-4-(4-(2-methoxyphenyl)piperazin-1 -yl)butyl-6-bromopyrazolo[1,5-a]pyridin-2- ylcarbamide N-4-(4-(2,3-dichlorophenyl)piperazin-1 -yl)butyl-6-chloropyrazoio[1,5-a]pyridin- 2-ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1 -yl)butyl-6-chloropyrazolo[1,5-alpyridin-2-

ylcarbamide N-4-(4-(2,3-dichiorophenyl)piperazin-1-yl)butyl-6-fluoropyrazolo[1,5-a]pyridin-2- ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1 -yl)butyl-6-flucropyrazolo[1,5-a}pyridin-2- ylcarbamide

N-4-(4-(2-methoxyphenyl)piperazin-1 -yl)butyl-3-methoxycarbonylpyrazolo[1,5- aJpyridin-2-ylcarbamide N-4-(4-(2,3-dichlorophenyl)piperazin-1 -yh)butyl-3-methoxycarbonylpyrazolo[1,5- a)pyridin-2-ylcarbamide N-5-(4-(2,3-dichlorophenyl)piperazin-1-yl)pentylpyrazolo[1 ,5-alpyridin-2-

ylcarbamide N-5-(4-(2,3-dichlorophenyl)piperazin-1-yl)pentyl-5-methoxypyrazolo[1,5- a)pyridin-2-ylcarbamide N-5-(4-(2-methoxyphenyl)piperazin-1-yl)pentyl-5-methoxypyrazolo[1,5- alpyridin-2-ylcarbamide

N-5-(4-(2,3-dichlorophenyl)piperazin-1 -yl)pentyi-5-trifluoromethylpyrazolo[1,5- a)pyridin-2-ylcarbamide

N-5-(4-(2-methoxyphenyl)piperazin-1 -yl)pentyl-5-trifiuoromethyipyrazolo[1 ,5- a]pyridin-2-ylcarbamide N-5-(4-(2,3-dichlorophenyl)piperazin-1 -yl)pentyi-6-bromopyrazolof[1 ,5-alpyridin- 2-ylcarbamide N-5-(4-(2-methoxyphenyl)piperazin-1-yl )pentyl-6-bromopyrazolo[1 ,5-a]pyridin-

2-ylcarbamide N-5-(4-(2,3-dichlorophenyl)piperazin-1 -yl)pentyl-6-chloropyrazolo{1,5-a]pyridin- 2-ylcarbamide N-5-(4-(2-methoxyphenyl)piperazin-1 -yl)pentyl-6-chloropyrazolo[1 ,5-a)pyridin-2-

ylcarbamide N-5-(4-(2,3-dichlorophenyl)piperazin-1 -yl)pentyl-6-fluoropyrazolo[1,5-a]pyridin- 2-ylcarbamide N-5-(4-(2-methoxyphenyl)piperazin-1 -yl)pentyl-6-fluoropyrazolo[1,5-a]pyridin-2- ylcarbamide trans-N-(4-((4-(2-methoxyphenyl)piperazin-1 -yl)methyl)cyclohex-1-yl)methyl- pyrazolo[1,5-a}pyridin-2-ylcarbamide trans-N-(4-((4-(2,3-dichlorophenyl)piperazin-1 -yl)methyl)cyclohex-1-yl)methyl- pyrazolo[1,5-a]pyridin-2-ylcarbamide N-2-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethylpyrazolo[1 ,5-a)pyridin-3-

ylcarbamide N-3-(4-(2,3-dichlorophenyl)piperazin-1-yi)propylpyrazolo[1 ,5-a]pyridin-3- ylcarbamide N-4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butylpyrazolo[1 ,5-a)pyridin-3- ylcarbamide

N-5-(4-(2,3-dichlorophenyl)piperazin-1-yl)pentylpyrazolo[1 ,5-a]pyridin-3- ylcarbamide trans-N-(4-((4-(2-methoxyphenyl)piperazin-1-yl)methyl )cyclohex-1-yl)methyl- pyrazolo[1,5-a]pyridin-3-ylcarbamide trans-N-(4-((4-(2,3-dichlorophenyl)piperazin-1-yl)methyl)cyclohex-1 -yl)methyl-

pyrazolo[1,5-a]pyridin-3-ylcarbamide N-2-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethylpyrazolo[1 ,5-a]pyridin-5- ylcarbamide N-3-(4-(2,3-dichlorophenyl)piperazin-1-yi)propylpyrazolo[1,5-a]pyridin-5- ylcarbamide

N-4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butylpyrazolo[1,5-a]pyridin-5- ylcarbamide

N-5-(4-(2,3-dichlorophenyl)piperazin-1 -yl)pentylpyrazolo[1,5-a]pyridin-5- ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1 -yl)butyl-3-bromopyrazolo[1,5-a]pyridin-5- ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1 -yl)butyl-3-chloropyrazolo[1,5-a]pyridin-5-

ylcarbamide N-5-(4-(2-methoxyphenyl)piperazin-1-yi)pentylpyrazolo[1 ,5-a]pyridin-5- ylcarbamide N-2-(4-(2,3-dichlorophenyl)piperazin-1 -yl)ethyipyrazolo[1,5-a]pyridin-6-

ylcarbamide N-3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propylpyrazolo[1 ,5-a)pyridin-6- ylcarbamide N-4-(4-(2,3-dichlorophenyl)piperazin-1 -yl)butylpyrazolo[1,5-a]pyridin-6- ylcarbamide

N-5-(4-(2,3-dichlorophenyl)piperazin-1-yl)pentylpyrazolo[1 ,5-a]pyridin-6- ylcarbamide N-2-(4-(2,3-dichlorophenyi)piperazin-1 -yl)ethyi-4,5,6,7-tetrahydropyrazolo[1,5- a]pyridin-2-ylcarbamide N-3-(4-(2,3-dichlorophenyl)piperazin-1 -yl)propyl-4,5,6,7-tetrahydropyrazolo[1,5-

a]pyridin-2-ylcarbamide N-4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butyl-4,5,6,7-tetrahydropyrazolo[1 5- alpyridin-2-ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1 -yl)butyl-4,5,6,7-tetrahydropyrazolo[1,5- a]pyridin-2-ylcarbamide

N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-5-methyl-4,5,6,7- tetrahydropyrazolo[1,5-a]pyridin-2-ylcarbamide N-5-(4-(2-methoxyphenyl)piperazin-1-yl)pentyl-4,5,6,7-tetrahyd ropyrazolo[1,5- a)pyridin-2-ylcarbamide N-5-(4-(2,3-dichlorophenyl)piperazin-1 -yl)pentyl-4,5,6,7-tetrahydropyrazolo[1,5-

a)pyridin-2-ylcarbamide N-2-(4-(2,3-dichlorophenyl)piperazin-1 -yl)ethyl-4,5,6,7-tetrahydropyrazolo[1,5- a)pyridin-3-ylcarbamide N-3-(4-(2,3-dichlorophenyl)piperazin-1 -yl)propyl-4,5,6,7-tetrahydropyrazolo[1,5- ajpyridin-3-yicarbamide

N-4-(4-(2,3-dichiorophenyl)piperazin-1 -yl)butyl-4,5,6,7-tetrahydropyrazolo[1,5- a)pyridin-3-ylcarbamide

N-5-(4-(2,3-dichlorophenyl)piperazin-1-yl )pentyl-4,5,6,7-tetrahydropyrazolo[1,5- a)pyridin-3-ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-6-chloroimidazo[1 ,2-alpyridin-2- ylcarbamide N-4-(4-(2,3-dichlorophenyl)piperazin-1-ylbutyl-6-chloroimidazo[1 ,2-a)pyridin-2- ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-6-chloro-2-methylimidazo[1,2- ajpyridin-3-ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butylimidazo[1,2-a]pyridin-6- ylcarbamide N-4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butyl-1,2,4-triazolo[1 ,5-a)pyridin-2- ylcarbamide N-4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butylpyrazolo[1,5-b}pyridazin-2- ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-6-chloroimidazo[1,2-b]pyridazin- 2-ylcarbamide N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-6-chloro-2-phenylimidazo[1,2- b]pyridazin-3-ylcarbamide

33. Compounds according to any one of the preceding claims as a pharmaceutical preparation.

34. Pharmaceutical composition comprising one or more of the compounds according to any one of the preceding claims and a pharmaceutically acceptable adjuvant.

35. Application of a compound according to one of the preceding claims for the production of a pharmaceutical preparation for the treatment of central nervous system illnesses.

36. Application of a compound according to any one of the preceding claims for the production of a pharmaceutical preparation for treatment of urinary tract disorders.

37. Use of a compound according to any one of the preceding claims for production of a pharmaceutical preparation for the treatment of ilinesses from the group comprising psychoses, schizophrenias, anxiety disorders, compulsive disorders, drug dependency, depressive disorders, drug-induced extrapyramidal motor disturbances, Parkinson's disease, Segawa syndrome, Tourette's syndrome, restless leg syndrome, sleeping disorders, nausea, cognitive disorders, male erectile dysfunction, hyperprolactinemia, hyperprolactinomia, glaucoma, attention deficit hyperactive syndrome (ADHS), autism, stroke and urinary incontinence.

38. Application according to any one of the preceding claims, wherein the compound is used for production of a pharmaceutical preparation for the treatment of schizophrenias, depressive disorders, L-dopa- or neuroleptic drug- induced motor disturbances, Parkinson's disease, Segawa syndrome, restless leg syndrome, hyperprolactinemia, hyperprolactinomia, attention deficit hyperactivity syndrome (ADHS) or urinary incontinence.

39. Method for treating a central nervous system iliness or a urinary tract disorder in a mammal characterised by the administration of one or more compounds according to any one of claims 1-32 to a mammal requiring such treatment.

40. Method according to claim 39, wherein the illness or disorder is selected from the group comprising psychoses, schizophrenias, anxiety disorders, compulsive disorders, drug dependency, depressive disorders, drug-induced extrapyramidal motor disturbances, Parkinson’s disease, Segawa syndrome, Tourette's syndrome, restless leg syndrome, sleeping disorders, nausea, cognitive disorders, male erectile dysfunction, hyperprolactinemia, hyperprolactinomia, glaucoma, attention deficit hyperactive syndrome (ADHS), autism, stroke and urinary incontinence.

41. Production of compounds according to any one of claims 1-32 by conversion of an acid derivative A

0 Br —— WwW (A) with a free base of general formula C R2 R3 /\ HN—Y—N N R4 — R6 RS wherein: W is selected from OH, Cl, Br or a group

X re” 07 in which R8 stands for alkyi; heteroarene in each case stands for a group which is selected from

9 2 ! \ 4 3 A — ’ = = 2 5 = — > B ' 2°

Qs PAN 22, 6 NN N Y 6 NN Np

Q, Q, 5 3

7 4 8 8 1 3 \ N . AJ OF Op OF 2 Vz * 2

Ny SN LN

7 5 3 5 3

8

N A) 4 3 R 8 2! * x N~ , 2

6 N 6 AN~p PANS 7

N N 3 in which 5 A, B, Q1, Q2, Q3, Q4, Q5, Q6 and Q7 in each case have the significance as defined in the preceding claims and wherein the crossed through bond for the heteroarenes stands for a bond of the —C(O)-W group to a ring-forming C- atom of an aromatic ring of the heteroarene; the heteroarene can in each case carry one or more further substituents R1 or R, as defined in the preceding claims; Y, R2, R3, R4, R5 and R6 in each case have the significance as defined in the preceding claims,

and wherein in the event that the substituent W is a hydroxy group, the appropriate acid group prior to the conversion with the free base of general formula C is activated by addition of one or more activation reagents.

42. Production of a carboxylic acid derivative of a pyrazolo[1,5-a]pyridine of general formula Rx 4 3 OR —=\ 2 R' 6 Ney 7 5 by conversion of a pyridine of formula X Rx * N with O-(2,4-dinitrophenyl)hydroxylamine to an N-aminopyridine of formula X Rx x N+ NH, and subsequent cycloaddition reaction with a propiolic acid ester of formula \ R'

in which Rx stands for 0, 1, 2, 3 or 4 identical or different substituents selected from among halogen, alkyl, alkylcarbonyl, phenyicarbonyl, hydroxyalkyl, cyano, trifluoromethyl and alkyloxycarbonyl, * denotes an unsubstituted CH group and in which R’ is selected from hydrogen, alkyl, phenyl and alkyloxycarbonyl and in which R” represents alkyl.