Pyrazole derivatives as sigma receptor inhibitors

Abstract

The invention relates to compounds of formula I having pharmacological activity towards the sigma receptor, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use for the treatment and or prophylaxis of a disease in which the sigma receptor is involved.

1 - 26 . (canceled) 
     
     
         27 . A method of treating or preventing a sigma receptor mediated disease or condition, said method comprising administering to a patient in need of such a treatment or prevention a therapeutically effective amount of a compound of formula (I): 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is selected from the group formed by hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkenyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO 2 , —N═CR 8 R 9 , or halogen; 
         R 2  is selected from the group formed by hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —S(O) t —R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO 2 , —N═CR 8 R 9 , or halogen; 
         Y is selected from substituted or unsubstituted phenyl or naphthyl; 
         X is selected from:
 —CH 2 -Het-CHR x —, 
 —CH 2 —CHR x -Het-, 
 -Het-CH 2 —CHR x —, 
 —CH 2 —CH 2 —CHR x —, or 
 —CH 2 —CHR x —CH 2 —,
 with 
 Het being NH, S or O, 
 —CHR x — being 
 
 
       
       
         
           
           
               
               
           
         
         
           
              wherein 
             R 5  and R 6 , identical or different, represent a hydrogen atom; an optionally substituted C 1-4  alkyl group; an optionally substituted aryl group; an optionally substituted heteroaryl group; a C 1-4  alkoxy group; a benzyl group; a phenethyl group; 
             or 
             form, together with their bridging nitrogen atom, an optionally substituted heteroaryl group which is optionally condensed to other, optionally at least one heteroatom containing mono- or polycyclic ring system which is optionally at least mono-substituted; 
           
         
         or 
         X is selected from:
 —CH 2 -Het-CHR x —, 
 —CH 2 —CHR x -Het-, 
 -Het-CH 2 —CHR x —, 
 —CH 2 —CH 2 —CHR x —, 
 —CH 2 —CHR x —CH 2 —, 
 —CH 2 —CH 2 —NR x —, or 
 —CH 2 —NR x —CH 2 —,
 with 
 Het being NH, S or O, 
 R x , being a —(C═O)—R 10 ; or a —(C═O)—O—R 11  group; wherein 
 R 10  and R 11  independently represent a hydrogen atom; a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl group; an optionally at least mono-substituted aryl group; an optionally at least mono-substituted heteroaryl group; an optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group; a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl-aryl group; a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl-heteroaryl group; or a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl-cycloalkyl group wherein the cycloalkyl group contains optionally at least one heteroatom as ring member; 
 
 
         n is selected from 1, 2, 3, 4, 5, 6, 7 or 8; 
         t is 1, 2 or 3; 
         R 8  and R 9  are each independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, or halogen; 
         optionally in form of a racemate in any mixing ratio, or a corresponding salt thereof. 
       
     
     
         28 . The method according to  claim 27 , wherein the compound of formula I comprises a compound of formula IB: 
       
         
           
           
               
               
           
         
       
       wherein
 R 1  is selected from the group formed by hydrogen; substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aromatic heterocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO2, —N═CR 8 R 9  or halogen, 
 R 2  is selected from the group formed by hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —S(O) t —R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO 2 , —N═CR 8 R 9 , or halogen; 
 R 3  and R 4  are independently selected from the group formed by hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —S(O) t —R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO2, —N═CR 8 R 9 , or halogen, or together with the phenyl ring to which they are attached they form a substituted or unsubstituted naphthyl ring, 
 X is selected from:
 —CH 2 -Het-CHR x —, 
 —CH 2 —CHR x -Het-, 
 -Het-CH 2 —CHR x —, 
 —CH 2 —CH 2 —CHR x —, or 
 —CH 2 —CHR x —CH 2 —,
 with 
 Het being NH, S or O, 
 —CHR x — being 
 
 
 
       
         
           
           
               
               
           
         
         
           
              wherein 
             R 5  and R 6 , identical or different, represent a hydrogen atom; an optionally substituted C 1-4  alkyl group; an optionally substituted aryl group; an optionally substituted heteroaryl group; a C 1-4  alkoxy group; a benzyl group; a phenethyl group; 
             or 
             form, together with their bridging nitrogen atom, an optionally substituted heteroaryl group which is optionally condensed to other, optionally at least one heteroatom containing mono- or polycyclic ring system which is optionally at least mono-substituted; 
           
         
         or 
         X is selected from:
 —CH 2 -Het-CHR x —, 
 —CH 2 —CHR x -Het-, 
 -Het-CH 2 —CHR x —, 
 —CH 2 —CH 2 —CHR x —, 
 —CH 2 —CHR x —CH 2 —, 
 —CH 2 —CH 2 —NR x —, or 
 —CH 2 —NR x —CH 2 —,
 with 
 Het being NH, S or O, 
 R x  being a —(C═O)—R 10 ; or a —(C═O)—O—R 11  group; wherein 
 R 10  and R 11  independently represent a hydrogen atom; a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl group; an optionally at least mono-substituted aryl group; an optionally at least mono-substituted heteroaryl group; an optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group; a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl-aryl group; a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl-heteroaryl group; or a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl-cycloalkyl group wherein the cycloalkyl group contains optionally at least one heteroatom as ring member; 
 
 
         n is selected from 1, 2, 3, 4, 5, 6, 7 or 8; 
         t is 1, 2 or 3; 
         R 8  and R 9  are each independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, or halogen; 
         optionally in form of a racemate in any mixing ratio, or a corresponding salt thereof. 
       
     
     
         29 . The method according to  claim 27 , wherein the compound of formula I comprises: 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is selected from the group formed by hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkenyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO 2 , —N═CR 8 R 9 , or halogen; 
         R 2  is selected from the group formed by hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —S(O) t —R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO 2 , —N═CR 8 R 9 , or halogen; 
         Y is selected from substituted or unsubstituted phenyl or naphtyl; 
         X is selected from:
 —CH 2 -Het-CHR x —, 
 —CH 2 —CHR x -Het-, 
 -Het-CH 2 —CHR x —, 
 —CH 2 —CH 2 —CHR x —, or 
 —CH 2 —CHR x —CH 2 —,
 with 
 Het being NH, S or O, 
 —CHR x — being 
 
 
       
       
         
           
           
               
               
           
         
         
           
              wherein 
             R 5  and R 6 , identical or different, represent a hydrogen atom; an optionally substituted C 1-4  alkyl group; an optionally substituted aryl group; an optionally substituted heteroaryl group; a C 1-4  alkoxy group; a benzyl group; a phenethyl group; 
             or 
             form, together with their bridging nitrogen atom, an optionally substituted heteroaryl group which is optionally condensed to other, optionally at least one heteroatom containing mono- or polycyclic ring system which is optionally at least mono-substituted; 
           
         
         n is selected from 1, 2, 3, 4, 5, 6, 7 or 8; 
         t is 1, 2, or 3; 
         R 8  and R 9  are each independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, or halogen; 
         optionally in form of a racemate in any mixing ratio, or a corresponding salt thereof. 
       
     
     
         30 . The method according to  claim 28 , wherein the compound of formula IB comprises: 
       
         
           
           
               
               
           
         
       
       wherein
 R 1  is selected from the group formed by hydrogen; substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aromatic heterocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO2, —N═CR 8 R 9  or halogen, 
 R 2  is selected from the group formed by hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —S(O) t —R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO 2 , —N═CR 8 R 9 , or halogen; 
 R 3  and R 4  are independently selected from the group formed by hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —S(O) t —R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO2, —N═CR 8 R 9 , or halogen, or together with the phenyl ring to which they are attached they form a substituted or unsubstituted naphthyl ring, 
 X is selected from:
 —CH 2 -Het-CHR x —, 
 —CH 2 —CHR x -Het-, 
 -Het-CH 2 —CHR x —, 
 —CH 2 —CH 2 —CHR x —, or 
 —CH 2 —CHR x —CH 2 —,
 with 
 Het being NH, S or O, —CHR x — being 
 
 
 
       
         
           
           
               
               
           
         
         
           
              with 
             R 5  and R 6 , identical or different, represent a hydrogen atom; an optionally substituted C 1-4  alkyl group; an optionally substituted aryl group; an optionally substituted heteroaryl group; a C 1-4  alkoxy group; a benzyl group; a phenethyl group; 
             or 
             form, together with their bridging nitrogen atom, an optionally substituted heteroaryl group which is optionally condensed to other, optionally at least one heteroatom containing mono- or polycyclic ring system which is optionally at least mono-substituted; 
           
         
         n is selected from 1, 2, 3, 4, 5, 6, 7 or 8; 
         t is 1, 2 or 3; 
         R 8  and R 9  are each independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, or halogen; 
         optionally in form of a racemate in any mixing ratio, or a corresponding salt thereof. 
       
     
     
         31 . The method according to  claim 27 , wherein the compound of formula I comprises: 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is selected from the group formed by hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkenyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO 2 , —N═CR 8 R 9 , or halogen; 
         R 2  is selected from the group formed by hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —S(O) t —R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO 2 , —N═CR 8 R 9 , or halogen; 
         Y is selected from substituted or unsubstituted phenyl or naphtyl; 
         X is selected from:
 —CH 2 -Het-CHR x —, 
 —CH 2 —CHR x -Het-, 
 -Het-CH 2 —CHR x —, 
 —CH 2 —CH 2 —CHR x —, 
 —CH 2 —CHR x —CH 2 —, 
 —CH 2 —CH 2 —NR x —, or 
 —CH 2 —NR x —CH 2 —,
 with 
 Het being NH, S or O, 
 R x  being a —(C═O)—R 10 ; or a —(C═O)—O—R 11  group; 
 and 
 R 10  and R 11  independently represent a hydrogen atom; a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl group; an optionally at least mono-substituted aryl group; an optionally at least mono-substituted heteroaryl group; an optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group; a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl-aryl group; a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl-heteroaryl group; or a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl-cycloalkyl group wherein the cycloalkyl group contains optionally at least one heteroatom as ring member; 
 
 
         n is selected from 1, 2, 3, 4, 5, 6, 7 or 8; 
         t is 1, 2 or 3; 
         R 8  and R 9  are each independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, or halogen; 
         optionally in form of a racemate in any mixing ratio, or a corresponding salt thereof. 
       
     
     
         32 . The method according to  claim 28 , wherein the compound of formula IB comprises: 
       
         
           
           
               
               
           
         
       
       wherein
 R 1  is selected from the group formed by hydrogen; substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aromatic heterocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO2, —N═CR 8 R 9  or halogen, 
 R 2  is selected from the group formed by hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —S(O) t —R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO 2 , —N═CR 8 R 9 , or halogen; 
 R 3  and R 4  are independently selected from the group formed by hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 —C═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —S(O) t —R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO2, —N═CR 8 R 9 , or halogen, or together with the phenyl ring to which they are attached they form a substituted or unsubstituted naphthyl ring, 
 X is selected from:
 —CH 2 -Het-CHR x —, 
 —CH 2 —CHR x -Het-, 
 -Het-CH 2 —CHR x —, 
 —CH 2 —CH 2 —CHR x —, 
 —CH 2 —CHR x —CH 2 —, 
 —CH 2 —CH 2 —NR x —, or 
 —CH 2 —NR x —CH 2 —,
 with 
 Het being NH, S or O, 
 R x  being a —(C═O)—R 10 ; or a —(C═O)—O—R 11  group; 
 and 
 R 10  and R 11  independently represent a hydrogen atom; a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl group; an optionally at least mono-substituted aryl group; an optionally at least mono-substituted heteroaryl group; an optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group; a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl-aryl group; a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl-heteroaryl group; or a saturated or unsaturated, optionally at least mono-substituted C 1-6  alkyl-cycloalkyl group wherein the cycloalkyl group contains optionally at least one heteroatom as ring member; 
 
 
 n is selected from 1, 2, 3, 4, 5, 6, 7 or 8; 
 t is 1, 2 or 3; 
 R 8  and R 9  are each independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, or halogen; 
 optionally in form of a racemate in any mixing ratio, or a corresponding salt thereof. 
 
     
     
         33 . The method according to  claim 27 , wherein the compound of formula I is characterized in that R 1  is selected from H, halogen, —COR 8 , or substituted or unsubstituted alkyl, preferably it is selected from H, Cl, methyl or acetyl. 
     
     
         34 . The method according to  claim 27 , wherein the compound of formula I is characterized in that R 1  is hydrogen. 
     
     
         35 . The method according to  claim 27 , wherein the compound of formula I is characterized in that R 2  is H, aryl, C(O)OR 8  or alkyl, preferably methyl, iso-propyl, phenyl, C(O)O—C 2 H 5  or H. 
     
     
         36 . The method according to  claim 28 , wherein the compound of formula IB is characterized in that R 3  and R 4  are situated in the meta and para positions of the phenyl group. 
     
     
         37 . The method according to  claim 28 , wherein the compound of formula IB is characterized in that R 3  and R 4  are independently selected from halogen, hydrogen, alkoxy, or substituted or unsubstituted alkyl, more preferably selected from hydrogen, halogen, Cl, methoxy or haloalkyl. 
     
     
         38 . The method according to  claim 28 , wherein the compound of formula IB is characterized in that R 3  and R 4  together with the phenyl ring to which they are attached form a substituted or unsubstituted naphthyl-radical. 
     
     
         39 . The method according to  claim 27 , wherein the compound of formula I is characterized in that n is selected from 2, 3, and 4. 
     
     
         40 . The method according to  claim 27 , wherein the compound of formula I is characterized in that X is selected from the group consisting of
 —CH 2 —CH 2 —CHR x —, and   —CH 2 —CHR x —CH 2 —.   
     
     
         41 . The method according to  claim 27 , wherein the compound of formula I is characterized in that R 5  and R 6  are selected from hydrogen or alkyl
 or   form, together with their bridging nitrogen atom, an optionally substituted heteroaryl group which is optionally condensed to other, optionally at least one heteroatom containing mono- or polycyclic ring system which is optionally at least mono-substituted, especially an indazole or an 1H-indazole.   
     
     
         42 . The method according to  claim 27 , wherein the compound of formula I is characterized in that the compound is selected from the group consisting of:
 3-{1-[2-(1-(3,4-Dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy)ethyl]piperidin-4-yl}-3H-imidazo[4,5-b]pyridine, and   3-{1-[2-(1-(3,4-Dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy)ethyl]piperidin-4-yl}-3H-imidazo[4,5-b]pyridine oxalate,   
       optionally in form of a racemate in any mixing ratio, or a corresponding salt thereof. 
     
     
         43 . The method according to  claim 27 , wherein the compound of formula I is characterized in that X is selected from the group consisting of
 —CH 2 —CH 2 —NR x —, and   —CH 2 —NR x —CH 2 —.   
     
     
         44 . The method according to  claim 27 , wherein the compound of formula I is characterized in that R 10  and R 11  are independently selected from hydrogen or alkyl. 
     
     
         45 . The method according to  claim 27 , wherein the compound of formula I is characterized in that the compound is selected from the group consisting of
 1-(4-(2-(1-(3,4-dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy)ethyl)piperazin-1-yl)ethanone,   1-(4-(2-(1-(3,4-dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy)ethyl)piperazin-1-yl)ethanone oxalate,   1-{1-[2-(1-(3,4-Dichlorophenyl)-1H-pyrazol-3-yloxy)ethyl]piperidin-4-yl}ethanone,   1-{1-[2-(1-(3,4-Dichlorophenyl)-1H-pyrazol-3-yloxy)ethyl]piperidin-4-yl}ethanone oxalate,   1-{4-[2-(1-(3,4-Dichlo-rophenyl)-1H-pyrazol-3-yloxy)ethyl]piperazin-1-yl}ethanone,   1-{4-[2-(1-(3,4-Dichlo-rophenyl)-1H-pyrazol-3-yloxy)ethyl]piperazin-1-yl}ethanone oxalate,   1-(1-[2-{1-(2,4-Dichlo-rophenyl)-1H-pyrazol-3-yloxy}ethyl]piperidin-4-yl)ethanone,   1-(1-[2-{1-(2,4-Dichlo-rophenyl)-1H-pyrazol-3-yloxy}ethyl]piperidin-4-yl)ethanone oxalate,   1-(1-(2-(1-(4-Chloro-phenyl)-1H-pyrazol-3-yloxy)ethyl)piperidin-4-yl)ethanone,   1-(1-(2-(1-(4-Chloro-phenyl)-1H-pyrazol-3-yloxy)ethyl)piperidin-4-yl)ethanone oxalate,   1-(1-(2-(1-(3,4-Dichlo-rophenyl)-5-methyl-1H-pyrazol-3-yloxy)ethyl)piperidin-4-yl)ethanone,   1-(1-(2-(1-(3,4-Dichlo-rophenyl)-5-methyl-1H-pyrazol-3-yloxy)ethyl)piperidin-4-yl)ethanone oxalate,   1-(4-(4-(1-(3,4-Dichlo-rophenyl)-4,5-dimethyl-1H-pyrazol-3-yloxy)butyl)piperazin-1-yl)ethanone,   1-(4-(4-(1-(3,4-Dichlo-rophenyl)-4,5-dimethyl-1H-pyrazol-3-yloxy)butyl)piperazin-1-yl)ethanone oxalate,   1-(4-(2-(1-(2,4-Dichlo-rophenyl)-1H-pyrazol-3-yloxy)ethyl)piperazin-1-yl)ethanone,   1-(4-(2-(1-(2,4-Dichlo-rophenyl)-1H-pyrazol-3-yloxy)ethyl)piperazin-1-yl)ethanone oxalate,   1-(4-(2-(1-(3,4-Dichlo-rophenyl)-4,5-dimethyl-1H-pyrazol-3-yloxy)ethyl)piperazin-1-yl)ethanone,   1-(4-(2-(1-(3,4-Dichlo-rophenyl)-4,5-dimethyl-1H-pyrazol-3-yloxy)ethyl)piperazin-1-yl)ethanone oxalate,   1-(4-{4-[1-(3,4-Dichloro-phenyl)-5-methyl-1H-pyrazol-3-yloxy]-butyl}-piperazin-1-yl)-ethanone, and   1-(4-{4-[1-(3,4-Dichloro-phenyl)-5-methyl-1H-pyrazol-3-yloxy]-butyl}-piperazin-1-yl)-ethanone oxalate;   optionally in form of a racemate in any mixing ratio, or a corresponding salt thereof.   
     
     
         46 . The method according to  claim 27 , wherein the compound of formula I is provided as a pharmaceutical composition which comprises a compound as defined in claim  1  or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle. 
     
     
         47 . The method according to  claim 27 , wherein the disease is diarrhoea, lipoprotein disorders, metabolic syndrome, treatment of elevated triglyceride levels, chylomicronemia, hyperlipoproteinemia; hyperlipidemia, especially mixed hyperlipidemia; hypercholesterolemia, dysbetalipoproteinemia, hypertriglyceridemia including both the sporadic and familial disorder (inherited hypertriglyceridemia), migraine, obesity, arthritis, hypertension, arrhythmia, ulcer, learning, memory and attention deficits, cognition disorders, neurodegenerative diseases, demyelinating diseases, addiction to drugs and chemical substances including cocaine, amphetamine, ethanol and nicotine, tardive diskinesia, ischemic stroke, epilepsy, stroke, depression, stress, psychotic condition, schizophrenia; inflammation, autoimmune diseases or cancer; disorders of food ingestion, the regulation of appetite, for the reduction, increase or maintenance of body weight, for the prophylaxis and/or treatment of obesity, bulimia, anorexia, cachexia or type II diabetes, preferably type II diabetes caused by obesity. 
     
     
         48 . The method according to  claim 27 , wherein the disease is pain, especially neuropathic pain, inflammatory pain or other pain conditions, allodynia and/or hyperalgesia, especially mechanical allodynia.