Claims
- 1. A compound of formula I: ##STR9## wherein: R.sup.1 is hydrogen, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, straight-chain or branched alkyl group having up to 6 carbons or benzyl optionally substituted by one to three substituents selected from halogen, amino, nitro, hydroxy, and C.sub.1 -C.sub.6 alkoxy;
- R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl;
- R.sup.3 is hydrogen, straight-chain or branched alkyl group having up to 10 carbon atoms, cyclohexylmethyl, --(CH.sub.2).sub.m Ar where Ar is phenyl, thienyl, furanyl, or pyridinyl, each optionally substituted by one to two substituents selected from halogen, C.sub.1 -C.sub.6 alkoxy, trifluoromethyl and C.sub.1 -C.sub.6 alkyl, and m is 1-3;
- or NR.sup.2 R.sup.3 is 1,2,3,4-tetrahydroquinolin-1-yl or 1,2,3,4-tetrahydroisoquinolin-2-yl;
- Y is hydrogen, halogen, lower alkyl, amino, or lower alkoxy; and
- n is 1-5,
- provided, however, that where R.sup.1 is aminoloweralkyl, both R.sup.2 and R.sup.3 may not be hydrogen,
- or a pharmaceutically acceptable salt thereof.
- 2. A compound according to claim 1 wherein R.sup.3 is benzyl, substituted benzyl, thienylmethyl, furanylmethyl, phenybutyl, or cyclohexylmethyl, R.sup.1 is trifluoromethyl or pentafluoroethyl; and NR.sup.2 R.sup.3 tetrahydroisoquinolinyl.
- 3. A compound according to claim 1 which is [2-(1H-benzoimidazol4-yloxy)-ethyl]-benzyl-amine or a pharmaceutically acceptable salt thereof.
- 4. A compound according to claim 1 which is benzyl-[2-(2-methyl-1H-benzoimidazol-4-yloxy)-ethyl]-amine or a pharmaceutically acceptable salt thereof.
- 5. A compound according to claim 1 which is benzyl-[2-(2-trifluoromethyl-1H-benzoimidazol-4-yloxy)-ethyl]-amine or a pharmaceutically acceptable salt thereof.
- 6. A compound according to claim 1 which is (4methyl-benzyl)-[2-(2-trifluoromethyl-1H-benzoimidazol-4-yloxy)-ethyl]-amine or a pharmaceutically acceptable salt thereof.
- 7. A compound according to claim 1 which is [2-(2-benzyl-1H-benzoimidazol-4-yloxy)ethyl]-(4-methyl-benzyl)-amine or a pharmaceutically acceptable salt thereof.
- 8. A compound according to claim 1 which is (4-methyl-benzyl)-{2-[2-(1,1,2,2,2-pentafluoro ethyl)-1H-benzoimidazol-4-yloxy]-ethyl}-amine or a pharmaceutically acceptable salt thereof.
- 9. A compound according to claim 1 which is thiophen-2-ylmethyl-[2-(2-trifluoromethyl-1H-benzoimidazol-4yloxy)-ethyl]-amine or a pharmaceutically acceptable salt thereof.
- 10. A compound according to claim 1 which is benzyl-[3-(2-trifluoromethyl-1H-benzoimidazol-4-yloxy)-propyl]-amine or a pharmaceutically acceptable salt thereof.
- 11. A compound according to claim 1 which is benzyl-{2-[2-(1,1,2,2,2-pentafluoro-ethyl)-1H-benzoimidazol-4-yloxy]-ethyl}-amine or a pharmaceutically acceptable salt thereof.
- 12. A compound according to claim 1 which is naphthlene-1-ylmethyl-[2-(2-trifluoromethyl-1H-benzoimidazol-4-yloxy]-ethyl]-amine or a pharmaceutically acceptable salt thereof.
- 13. A compound according to claim 1 which is thiophen-2-ylmethyl-[2-(1H-benzoimidazol-4-yloxy)-ethyl]-amine or a pharmaceutically acceptable salt thereof.
- 14. A compound according to claim 1 which is (4-methyl-benzyl)-{2-[2-(1,1,2,2,3,3,3-heptafluoro-propyl)-1H-benzoimidazol-4-yloxy]-ethyl}-amine or a pharmaceutically acceptable salt thereof.
- 15. A compound according to claim 1 which is 2-[2-(2-trifluoromethyl-1H-benzoimidazol-4-yloxy-ethyl]-1,2,3,4-tetrahydro-isoquinoline or a pharmaceutically acceptable salt thereof.
- 16. A compound according to claim 1 which is benzyl-[2-(6-chloro-2-trifluoromethyl-1H-benzoimidazol-4-yloxy)-ethyl-amine or a pharmaceutically acceptable salt thereof.
- 17. A compound according to claim 1 which is 4chloro-benzyl-[2-(6chloro-2-trifluoromethyl-1H-benzoimidazol-4yloxy)-ethyl-amine or a pharmaceutically acceptable salt thereof.
- 18. A compound according to claim 1 which is (4-fluoro-benzyl)-2[2-(2-trifluoromethyl-1H-benzoimidazol-4-yloxy)-ethyl]-amine or a pharmaceutically acceptable salt thereof.
- 19. A compound according to claim 1 which is [2-(2-trifluoromethyl-1H-benzoimidazol-4-yloxy)-ethyl]-(4-trifluoromethyl-benzyl)-amine or a pharmaceutically acceptable salt thereof.
- 20. A compound according to claim 1 which is (3-phenyl-propyl)-[2-(2-trifluoromethyl-1H-benzoimidazol-4-yloxy)-ethyl]-amine or a pharmaceutically acceptable salt thereof.
- 21. A method of treating diseases in a mammal which respond to treatment with dopamine D.sub.2 agonists which comprises administering to a mammal in need thereof a therapeutically effective amount of a compound of the formula ##STR10## wherein: R.sup.1 is hydrogen, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, straight-chain or branched alkyl group having up to 6 carbons or benzyl optionally substituted by one to three substituents selected from halogen, amino, nitro, hydroxy, and C.sub.1 -C.sub.6 alkoxy;
- R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl;
- R.sup.3 is hydrogen, straight-chain or branched alkyl group having up to 10 carbon atoms, cyclohexylmethyl or --(CH.sub.2).sub.m Ar where Ar is phenyl, naphthalenyl, thienyl, furanyl, or pyridinyl, each optionally substituted by one to two substituents selected from halogen, C.sub.1 -C.sub.6 alkoxy, trifluoromethyl and C.sub.1 -C.sub.6 alkyl, and m is 1-3;
- or NR.sup.2 R.sup.3 is 1,2,3,4-tetrahydroquinolin-1-yl or 1,2,3,4-tetrahydroisoquinolin-2-yl;
- Y is hydrogen, halogen, lower alkyl, amino, or lower alkoxy; and
- n is 1-5,
- or a pharmaceutically acceptable salt thereof.
- 22. The method of treatment according to claim 21 wherein the disease treated is schizophrenia.
- 23. The method of treatment according to claim 21 wherein the disease treated is Parkinson's disease.
- 24. The method of treatment according to claim 21 wherein the disease treated is Tourette's syndrome.
- 25. The method of treatment according to claim 21 wherein the disease treated is drug or alcohol addiction.
- 26. A pharmaceutical composition which comprises a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of the formula ##STR11## wherein: R.sup.1 is hydrogen, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, straight-chain or branched alkyl group having up to 6 carbons or benzyl optionally substituted by one to three substituents selected from halogen, amino, nitro, hydroxy, and C.sub.1 -C.sub.6 alkoxy;
- R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl;
- R.sup.3 is hydrogen, straight-chain or branched alkyl group having up to 10 carbon atoms, cyclohexylmethyl or --(CH.sub.2).sub.m Ar where Ar is phenyl naphthalenyl, thienyl, furanyl, or pyridinyl, each optionally substituted by one to two substituents selected from halogen, C.sub.1 -C.sub.6 alkoxy, trifluoromethyl and C.sub.1 -C.sub.6 alkyl, and m is 1-3;
- or NR.sup.2 R.sup.3 is 1,2,3,4-tetrahydroquinolin-1-yl or 1,2,3,4-tetrahydroisoquinolin-2-yl;
- Y is hydrogen, halogen, lower alkyl, amino, or lower alkoxy; and
- n is 1-5,
- provided, however, that where R.sup.1 is aminoloweralkyl, both R.sup.2 and R.sup.3 may not be hydrogen.
- or a pharmaceutically acceptable salt thereof.
Parent Case Info
This application claims benefit of priority of provisional patent application 60/038,681 filed Feb. 18, 1997.
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