Triazole compounds and the therapeutic use thereof

1. A triazole compound of the formula I

in which

A is C 4 -C 10 -alkylene or C 3 -C 10 -alkylene which includes at least one group Z which is selected from O, S, NR 5 , CONR 5 , COO and CO, where alkylene may also have a C 3 -C 6 -cycloalkylene group and/or a double or triple bond,

B is CH 2 or CH 2 -CH 2 ;

R 1 is an aromatic radical which is selected from phenyl and a 5- or 6-membered heteroaromatic radical having 1, 2, 3 or 4 heteroatoms which are selected independently of one another from O, N and S, where the aromatic radical may have one or more substituents which are selected independently of one another from C 1 -C 6 -alkyl which is optionally substituted by OH, C 1 -C 4 -alkoxy, halogen or phenyl, or C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl which is optionally substituted by halogen or C 1 -C 4 -alkyl, or halogen, CN, OR 6 , COOR 6 , NR 7 R 8 , NO 2 , SR 9 , SO 2 R 9 , SO 2 NR 7 R 8 , COR 10 , and phenyl which is optionally substituted by one or two radicals which are selected independently of one another from C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, NR 7 R 8 , CN, CF 3 , CHF 2 or halogen, where phenyl and the heteroaromatic radical may also be fused to a 5 or 6-membered, aromatic or nonaromatic carbocycle;

R 2 is H, C 1 -C 6 -alkyl which is optionally substituted by OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, halogen or phenyl, or OH, C 1 -C 6 -alkoxy, OCF 3 , OCHF 2 , OSO 2 CF 3 , SH, C 1 -C 6 -alkylthio, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, halogen, CN or NO 2 ;

R 3 is C 2 -C 10 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 10 -alkyl which is substituted by C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio or phenyl which may in turn have one, two or three substituents selected from C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, halogen, CN, OR 6 , COOR 6 , NR 7 R 8 , NO 2 , SR 9 , SO 2 R 9 , SO 2 NR 7 R 8 , COR 10 and halogen, is C 3 -C 6 -cycloalkyl which is optionally substituted by halogen or C 1 -C 4 -alkyl, or is an aromatic radical which is selected from phenyl, naphthyl and a 5- or 6-membered heteroaromatic radical having 1, 2, or 3 heteroatoms which are selected independently of one another from O, N and S, where the aromatic radical may have one or two substituents which are selected independently of one another from C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, halogen, CN, COOR 6 , NR 7 R 8 , NO 2 , SO 2 R 9 , SO 2 NR 7 R 8 , COR 10 , CF 3 , CHF 2 or halogen, where R 3 may also be methyl if R 1 is an optionally substituted heteroaromatic radical;

R 4 is H, C 1 -C 6 -alkyl which is optionally substituted by OH, C 1 -C 4 -alkoxy or phenyl, or C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl which is optionally substituted by C 1 -C 4 -alkyl or halogen, or phenyl;

R 5 is H, C 1 -C 6 -alkyl which is optionally substituted by OH, C 1 -C 4 -alkoxy or phenyl, or C 1 -C 6 -haloalkyl, phenyl or a COR 11 group;

R 6 to R 10 are independently of one another H, C 1 -C 6 -alkyl which is optionally substituted by OH, C 1 -C 4 -alkoxy or phenyl, or C 1 -C 6 -haloalkyl or phenyl, where R 8 may also be a COR 11 group in which R 11 has one of the meanings mentioned for R 4 ;

R 7 may also form together with R 8 a 5- or 6-membered saturated or unsaturated carbocycle which may have a heteroatom selected from O, S, N and NR 12 as ring member, where R 12 is hydrogen or C 1 -C 4 -alkyl,

or a physiologically tolerated salt of this compound.

2. The compound as claimed in claim 1 in which B is CH 2 CH 2 .

3. The compound as claimed in claim 1 in which A is C 4 -C 10 -alkylene or Z-C 3 -C 10 -alkylene, where alkylene may have a double bond, Z is bonded to the triazole ring and is selected from O, S, COO, NR 5 and CO.

4. The compound as claimed in claim 3 in which A is a group S—(C 3 -C 10 -alkylene) in which alkylene may have a double bond.

5. The compound as claimed in claim 1 in which R 2 is H.

6. The compound as claimed in claim 1 in which R 1 is phenyl which is unsubstituted or has one or two substituents which are selected independently of one another from C 1 -C 6 -alkyl, OH, C 1 -C 6 -alkoxy, phenyl, CN and halogen and/or which may be fused to a 6-membered aromatic carbocyle.

7. The compound as claimed in claim 1 in which R 1 is a heteroaromatic radical which is selected from thienyl, furanyl, tetrazolyl, pyrrolyl, benzothienyl, indolyl, benzothiazolyl, pyridyl or pyrazinyl, where the aromatic radical may be substituted in the manner indicated in claim 1 .

8. The compound as claimed in claim 7 , in which R 1 is pyrrolyl which optionally has 1 or 2 substituents selected from C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl.

9. The compound as claimed in claim 1 in which R 3 is C 2 -C 10 -alkyl, C 3 -C 6 -cycloalkyl, benzyl or phenyl which may have one or two substituents which are selected independently of one another from C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, halogen, CN, NO 2 , CF 3 , CHF 2 or halogen.

10. The compound as claimed in claim 1 of the formula Ia

in which A, R 1 R 3 and R 4 have the meanings indicated above.

11. The compound as claimed in claim 10 in which

A is C 4 -C 10 -alkylene or Z-C 3 -C 10 -alkylene, where alkylene may have a double bond, Z is bonded to the triazole ring and is selected from O, S, COO, CONR 5 , NR 5 and CO;

R 1 is an aromatic radical which is selected from phenyl, thienyl, furanyl, tetrazolyl, pyrrolyl, benzothienyl, indolyl, benzothiazolyl, pyridyl or pyrazinyl, where the aromatic radical may be substituted in the manner indicated in claim 1 ;

R 3 is C 2 -C 10 -alkyl, C 3 -C 6 -cycloalkyl, benzyl or phenyl which may have one or two substituents which are selected independently of another from C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, halogen, CN, NO 2 , CF 3 , CHF 2 or halogen, where R 3 may also be methyl if R 1 is not optionally substituted phenyl, and

R 4 is hydrogen, C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl.

12. The compound as claimed in claim 1 in which R 1 is pyrrolyl which optionally has 1 or 2 substituents selected from C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl.

13. The compound as claimed in claim 10 of the formula Ia in which A is a group S—(C 3 -C 10 -alkylene) in which alkylene may have a double bond.

14. The compound as claimed in claim 11 in which R 2 is methyl, A is a group Z′-(CH 2 ) k where Z′ is bonded to the triazole ring and is oxygen, sulfur or CH 2 , k is 3 or 4,

R 1 is phenyl, 4-fluorophenyl, pyrrol-2-yl, 1-methylpyrrol-2-yl, 2-thienyl, 3-thienyl, benzothien-2-yl, 2-furyl, 3-furyl, benzothiazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl or 2-pyrazinyl, and

R 3 is C 2 -C 4 -alkyl or phenyl which may be substituted once or twice by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, CF 3 , CHF 2 or halogen, or may also be methyl if R 1 is different from phenyl.

15. A pharmaceutical composition comprising at least one compound of the formula I as claimed in claim 1 , where appropriate together with physiologically acceptable carriers and/or excipients.

16. A method for the treatment of disorders which respond to influencing of dopamine D 3 receptors, selected from Parkinson's disease, schizophrenia, cognitive disturbances, depression, axiety, addiction, kidney function disturbances and eating disturbances, comprising administering to a patent in need of such treatment an effective amount of at least one compound of claim 1 .