Imidazo-pyrimidine derivatives as ligands for gaba receptors

1. A compound of formula I, or a pharmaceutically acceptable salt thereof:

wherein

X 1 represents halogen, trifluoromethyl or C 1-6 alkoxy;

X 2 represents hydrogen or halogen;

Y represents a chemical bond, an oxygen atom, or a —NH— linkage;

Z represents an optionally substituted aryl or heteroaryl group;

R 1 represents hydrogen, hydrocarbon, a heterocyclic group, halogen, cyano, trifluoromethyl, nitro, —OR a , —SR a , —SOR a , —SO 2 R a , —SO 2 NR a R b , —NR a R b , —NR a COR b , —NR a CO 2 R b , —COR a , —CO 2 R a , —CONR a R b or —CR a ═NOR b ;

R 2 represents hydrogen or halogen; and

R a and R b independently represent hydrogen, hydrocarbon or a heterocyclic group.

2. A compound as claimed in claim 1 represented by formula IIA, or a pharmaceutically acceptable salt thereof:

wherein

Z and R 2 are as defined in claim 1 ;

X 11 represents fluoro, chloro, trifluoromethyl or methoxy;

X 12 represents hydrogen or fluoro;

R 11 represents hydrogen, C 1-6 alkyl, halo(C 1-6 )alkyl, dihalo(C 1-6 )alkyl, hydroxy(C 1-6 )alkyl, dihydroxy(C 1-6 )alkyl, C 1-6 alkoxy(C 1-6 )alkyl, di(C 1-6 )alkoxy(C 1-6 )alkyl, cyano(C 1-6 )alkyl, C 2-6 alkoxycarbonyl(C 1-6 )alkyl, heteroaryl, C 1-6 alkyl-heteroaryl, heteroaryl(C 1-6 )alkyl, halogen, cyano, trifluoromethyl, formyl, C 2-6 alkylcarbonyl, C 2-6 alkoxycarbonyl or —CR 5 ═NOR 6 ;

R 5 represents hydrogen or C 1-6 alkyl; and

R 6 represents hydrogen, C 1-6 alkyl, hydroxy(C 1-6 )alkyl or di(C 1-6 )alkylamino(C 1-6 )alkyl.

3. A compound as claimed in claim 2 represented by formula IIB, or a pharmaceutically acceptable salt thereof:

wherein X 11 , X 12 and R 11 are as defined in claim 2 ; and

R 7 represents hydrogen, fluoro or chloro.

4. A compound as claimed in claim 3 wherein R 7 represents fluoro.

5. A compound as claimed in claim 4 wherein R 11 represents trifluoromethyl.

6. A compound as claimed in claim 2 represented by formula IIC, or a pharmaceutically acceptable salt thereof:

wherein X 11 , X 12 and R 11 are as defined in claim 2 ; and

R 7 represents hydrogen, fluoro or chloro.

7. A compound as claimed in claim 2 represented by formula IID, or a pharmaceutically acceptable salt thereof:

wherein X 11 , X 12 and R 11 are as defined in claim 2 ; and

R 8 represents hydrogen, fluoro, cyano or methyl.

8. A compound as claimed in claim 7 wherein R 8 represents hydrogen.

9. A compound as claimed in claim 8 wherein R 11 represents 2-hydroxyprop-2-yl.

10. A compound as claimed in claim 2 represented by formula IIE, or a pharmaceutically acceptable salt thereof:

wherein X 11 , X 12 and R 11 are as defined in claim 2 ;

R 8 represents hydrogen, fluoro, cyano or methyl; and

R 9 represents hydrogen or fluoro.

11. A compound as claimed in claim 5 wherein X 11 represents fluoro.

12. A compound as claimed in claim 9 wherein X 11 represents fluoro.

13. A compound as claimed in claim 11 wherein X 12 represents hydrogen.

14. A compound as claimed in claim 12 wherein X 12 represents hydrogen.

15. A compound selected from:

2′-fluoro-5′-(imidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

2′-fluoro-5′-(7-methylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

5′-(7-acetylimidazo[1,2-α]pyrimidin-3-yl)-2′-fluorobiphenyl-2-carbonitrile;

2′-fluoro-5′-(7-isopropylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

2′-fluoro-5′-(7-tert-butylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

2′-fluoro-5′-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-[7-(1-fluoro-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-(7-hydroxymethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

2′-fluoro-5′-[7-(1-hydroxyethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-[7-(1-fluoroethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-[7-(2-methylthiazol-5-yl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

5′-[7-(1,1-difluoroethyl)imidazo[1,2-α]pyrimidin-3-yl]-2′-fluorobiphenyl-2-carbonitrile;

5′-(7-chloroimidazo[1,2-α]pyrimidin-3-yl)-2′-fluorobiphenyl-2-carbonitrile;

5′-(7-difluoromethylimidazo[1,2-α]pyrimidin-3-yl)-2′-fluorobiphenyl-2-carbonitrile;

2′-fluoro-5′-(7-methoxymethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

3-(2′-cyano-6-fluorobiphenyl-3-yl)imidazo[1,2-α]pyrimidine-7-carbonitrile;

2′-fluoro-5′-[7-(3-methyl-[1,2,4]oxadiazol-5-yl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-[7-(oxazol-5-yl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-[7-(hydroxyiminomethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

5′-{7-[1-(2-dimethylaminoethoxyimino)methyl]imidazo[1,2-α]pyrimidin-3-yl}-2′-fluorobiphenyl-2-carbonitrile;

3′-(7-difluoromethylimidazo[1,2-α]pyrimidin-3-yl)-4′-fluorobiphenyl-2-carbonitrile;

2′-fluoro-5′-(7-fluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

2′-fluoro-5′-[7-(furan-3-yl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-[7-(thien-3-yl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-[7-(pyridin-2-yl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-(6-fluoro-7-methylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

7-(1,1-difluoroethyl)-3-[4-fluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyrimidine;

2-[3-(4-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

3′-fluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

3′-fluoro-5′-(7-hydroxymethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

2′-fluoro-3′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

3-[4-fluoro-3-(pyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(pyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

2′-fluoro-5′-[7-([1,2,4]triazol-1-ylmethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-[7-(imidazol-1-ylmethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-[7-([1,2,3]triazol-1-ylmethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-[7-([1,2,3]triazol-2-ylmethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

3-[4-fluoro-3-(pyridin-4-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[2,4-difluoro-3-(pyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[2,4-difluoro-3-(pyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

2-[3-(4-fluoro-3-(pyridin-4-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

3-[2-fluoro-3-(pyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

2-[3-(2-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

3-[2-fluoro-3-(pyridin-4-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

2-[3-(2-fluoro-3-(pyridin-4-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

3-[2-fluoro-3-(pyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

2-[3-(2-fluoro-3-(pyridin-2-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

3-[4-fluoro-3-(4-methylpyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(pyridazin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

2-[2-fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenyl]nicotinonitrile;

3-[4-fluoro-3-(pyridin-2-yl)phenyl]imidazo[1,2-α]pyrimidine;

3,2′-difluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

6,2′-difluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

5,2′-difluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

4,2′-difluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

2′,6′-difluoro-3′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

3-[4-fluoro-3-(pyrazin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(pyrimidin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[2-fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenyl]pyridine-2-carbonitrile;

3-[4-fluoro-3-(5-fluoropyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

7-(1,1-difluoroethyl)-3-[4-fluoro-3-(pyridin-4-yl)phenyl]imidazo[1,2-α]pyrimidine;

7-(1,1-difluoroethyl)-3-[2,4-difluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyrimidine;

3-[4-chloro-3-(pyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-methoxy-3-(pyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

and pharmaceutically acceptable salts thereof.

16. A compound selected from:

2-[3-(2,4-difluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

1-[3-(4-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]ethanone;

3′-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]-4,2′,6′-trifluorobiphenyl-2-carbonitrile;

2-[3-(4-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propane-1,2-diol;

3-[2-fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenyl]thiophene-2-carbonitrile;

3-{2-fluoro-5-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]phenyl}thiophene-2-carbonitrile;

2-{3-[4-fluoro-3-(1-oxypyridin-3-yl)phenyl]imidazo[1,2-α]pyrimidin-7-yl}propan-2-ol;

3-{2,6-difluoro-3-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]phenyl}thiophene-2-carbonitrile;

3-{2,6-difluoro-3-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]phenyl}thiophene-2-carboxylic acid amide;

3-[4-fluoro-3-(3-fluoropyridin-4-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

4-chloro-2′-fluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile;

3-[4-fluoro-3-(5-methylpyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[2-fluoro-2′-(methanesulfonyl)biphenyl-5-yl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

2-[3-(4-fluoro-3-(pyrazin-2-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

2-[3-(4-fluoro-3-(5-fluoropyridin-2-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

3-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

2-[3-(4-fluoro-3-(3-fluoropyridin-2-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

3-[3-(3,5-difluoropyridin-2-yl)-4-fluorophenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

2-[3-(3-(3,5-difluoropyridin-2-yl)-4-fluorophenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

3-[2,4-difluoro-3-(pyridin-4-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

2-[3-(2,4-difluoro-3-(pyridin-4-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

4,2′-difluoro-5′-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile;

2′-fluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-3-carbonitrile;

2′-fluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-4-carbonitrile;

3-[2,4-difluoro-3-(pyridin-3-yl)phenyl]-7-(1-fluoro-1-methylethyl)imidazo[1,2-α]pyrimidine;

7-(1-fluoro-1-methylethyl)-3-[4-fluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyrimidine;

2-[3-(2,4-difluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]-2-methylpropionic acid methyl ester;

2-[3-(4-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]-2-methylpropionitrile;

2-[3-(4-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]-2-methylpropan-1-ol;

3-[4-fluoro-3-(6-methoxypyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

5-[2-fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenyl]pyridin-2-ol;

3-[4-fluoro-3-(4-fluoropyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(pyrrol-1-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(5-fluoropyridin-2-yl)phenyl]imidazo[1,2-α]pyrimidine;

3-[2,4-difluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyrimidine;

3-[4-chloro-3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyrimidine;

3-[5-fluoro-3-(pyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(4-methylpyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[2-fluoro-5-(pyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(pyridazin-4-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(imidazol-1-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(isothiazol-4-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(pyrimidin-5-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(5-methoxypyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(2-methylpyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(2-methyltetrazol-5-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(1-methyltetrazol-5-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

and pharmaceutically acceptable salts thereof.

17. A compound selected from:

3-[4-fluoro-3-(6-methoxypyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(4-methoxypyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

3-[4-fluoro-3-(thiazol-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

2-{2-fluoro-5-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]phenyl}nicotinonitrile;

4-[2-fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenyl]nicotinonitrile;

4-{2-fluoro-5-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]phenyl}nicotinonitrile;

3-[2-fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenyl]isonicotinonitrile;

3-[2-fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenyl]isonicotinamide;

3-{2-fluoro-5-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]phenyl}isonicotinamide;

2-[3-(4-fluoro-3-(pyridazin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

2-[3-(4-fluoro-3-(pyridazin-4-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

3-[4-fluoro-3-(pyrazol-1-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

2-[3-(4-fluoro-3-(pyrazol-1-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

3-[4-fluoro-3-([1,2,4]triazol-1-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine;

2-[3-(4-fluoro-3-([1,2,4]triazol-1-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol;

2-[2-fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenyl]nicotinamide;

2-{3-[4-fluoro-3-(5-fluoropyridin-3-yl)phenyl]imidazo[1,2-α]pyrimidin-7-yl}propan-2-ol;

and pharmaceutically acceptable salts thereof.

18. A pharmaceutical composition comprising an effective amount of a compound of formula I as defined in claim 1 , or a pharmaceutically acceptable salt thereof, in association with a pharmaceutically acceptable carrier.

19. A method for the treatment and/or prevention of adverse neurological conditions which comprises administering to a patient in need of such treatment an effective amount of a compound of formula I as defined in claim 1 or a pharmaceutically acceptable salt thereof.

20. 2-[3-(4-Fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol, or a pharmaceutically acceptable salt thereof.

21. The bis-hydrochloride salt of 2-[3-(4-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol.

22. A pharmaceutical composition comprising an effective amount of 2-[3-(4-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol, or a pharmaceutically acceptable salt thereof, in association with a pharmaceutically acceptable carrier.

23. A pharmaceutical composition comprising an effective amount of the bis-hydrochloride salt of 2-[3-(4-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol in association with a pharmaceutically acceptable carrier.

24. A method for the treatment of anxiety which comprises administering to a patient in need of such treatment an effective amount of 2-[3-(4-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol, or a pharmaceutically acceptable salt thereof.

25. A method for the treatment of anxiety which comprises administering to a patient in need of such treatment an effective amount of the bis-hydrochloride salt of 2-[3-(4-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol.

26. 4,2′-Difluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile.

27. A pharmaceutical composition comprising an effective amount of 4,2′-difluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile in association with a pharmaceutically acceptable carrier.

28. A method for the treatment of anxiety which comprises administering to a patient in need of such treatment an effective amount of 4,2′-difluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile.