2-(aminomethyl) arylamide analgesics

1. A compound of formula

wherein

U is chosen from CH, N and CR 5 ;

A is chosen from the group consisting of (C 4 to C 6 )alkane; (C 2 to C 6 )fluoroalkane; (C 2 to C 6 )alkene; (C 2 to C 6 )alkyne; (C 2 to C 6 )oxaalkane and (C 2 to C 6 )thiaalkane;

Ar 1 is chosen from the group consisting of aryl, heteroaryl, substituted aryl and substituted heteroaryl;

R 2 , R 3 and R 5 are independently chosen from —H, loweralkyl, fluoroloweralkyl, halo, loweralkoxy, fluoroloweralkoxy and NO 2 ; and

R 1 and R 4 , together with the nitrogen to which they are attached, form a pyridoindole or substituted pyridoindole.

2. A compound according to claim 1 wherein U is N and R 2 and R 3 are H.

3. A compound according to claim 1 wherein U is CH.

4. A compound according to claim 3 wherein A is chosen from the group consisting of (C 4 to C 6 )alkane; (C 3 to C 5 )alkene; (C 3 to C 5 )alkyne; (C 3 to C 5 )oxaalkane and (C 3 to C 5 )thiaalkane.

5. A compound according to claim 3 wherein A is chosen from the group consisting of —CH 2 CH 2 CH═CH—; —(CH 2 ) 5 —; —(CH 2 ) 4 —; —CH 2 CH 2 C(CH 3 )═CH—; —CH 2 CH 2 C(CF 3 )═CH—; —CH 2 CH 2 OCH 2 —; —CH 2 CH 2 CH≡CH—; —(CH 2 ) 3 O—; —CH 2 CH 2 SCH 2 —; and

6. A compound according to claim 5 wherein A is (C 4 to C 5 )alkane or (C 3 to C 5 )alkene.

7. A compound according to claim 1 wherein Ar 1 is chosen from the group consisting of phenyl, halophenyl, dihalophenyl, methoxyphenyl, trifluoromethoxyphenyl, trifluoromethylphenyl, loweralkylphenyl, hydroxyphenyl, and pyridinyl.

8. A compound according to claim 1 – 7 wherein R 1 and R 4 , together with the nitrogen to which they are attached form a residue of the formula chosen from the group consisting of:

wherein

R 6 is chosen from the group consisting of hydrogen, hydroxy, loweralkyl, fluoroloweralkyl, loweralkoxyl, fluoroloweralkoxyl and halo;

R 7 is chosen from the group consisting of —R 16 , —OR 16 , —NH 2 , NO 2 , —CN, —NH(CO)NHR 17 , —CONH 2 , —NH(CO)CH 3 , —SO 2 NHR 17 , -halo, —CH 2 OH, —COOR 17 , —NH(SO 2 )CH 3 , and —NH(CO)H;

R 8 and R 9 are independently chosen from the group consisting of —R 16 , —CH 2 OH, and —COOR 17 ;

R 16 is chosen from the group consisting of hydrogen, loweralkyl and fluoroloweralkyl; and

R 12 and R 17 are independently chosen from the group consisting of hydrogen and loweralkyl.

9. A compound according to claim 8 wherein

R 6 is hydrogen or hydroxy;

R 7 is hydrogen;

R 8 is hydrogen or methyl; and

R 9 is hydrogen, methyl or —CH 2 OH.

10. A compound according to claim 9 wherein R 2 and R 3 are hydrogen.

11. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound according to claim 1 .

12. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound according to claim 9 .

13. A method for treating pain comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound according to claim 1 .

14. A method for treating pain comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound according to claim 9 .