Claims
- 1. A compound of the formula ##STR4## wherein m is an integer of 0,1 or 2;
- n is an integer of 1 or 2; and m+n is an integer of 2 or 3;
- R.sub.1 is hydrogen, alkyl, cycloalkyl, arylloweralkyl, aryl, naphthyl, furyl, thienyl, pyridinyl or pyrrolyl;
- each R.sub.2 and R.sub.3 are independently hydrogen, loweralkyl or aryllowralkyl;
- X is hydrogen, lower alkyl, cycloalkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, formyl, loweralkoxycarbonyl, arylcarbonyl, --SH, loweralkylthio, --NHCOR.sub.4 or --NR.sub.5 R.sub.6, R.sub.4 being hydrogen or loweralkyl, and R.sub.5 and R.sub.6 being independently hydrogen, loweralkyl or cycloalkyl; and Y is O or S;
- or a stereo, optical or geometrical isomer thereof, or a pharmaceutically acceptable acid addition salt thereof.
- 2. The compound as defined in claim 1, where (CHR.sub.3).sub.m is CH.sub.2, Y is S and (CHR.sub.2).sub.n is CH.sub.2 CH.sub.2.
- 3. The compound as defined in claim 2, where R.sub.1 is aryl.
- 4. The compound as defined in claim 3, where X is hydrogen, loweralkyl or trifluoromethyl.
- 5. The compound as defined in claim 1, which is N-(phenylmethylidene)-3,4-dihydro-1H-thiopyrano[4,3-b]quinolin-10-amine.
- 6. The compound as defined in claim 1, which is N-[(4-fluorophenyl)methylidene]-3,4-dihydro-1H-thiopyrano[4,3-b]quinolin-10-amine.
- 7. The compound as defined in claim 1, which is N-ethylidene-3,4-dihydro-1H-thiopyrano[4,3-b]quinolin-10-amine.
- 8. The compound as defined in claim 1, which is N-hexylidene-3,4-dihydro-1H-thiopyrano[4,3-b]quinolin-10-amine.
- 9. The compound as defined in claim 1, which is N-decylidene-3,4-dihydro-1H-thiopyrano[4,3-b]quinolin-10-amine.
- 10. The compound as defined in claim 1, which is N-hexadecylidene-3,4-dihydro-1H-thiopyrano[4,3-b]quinolin-10-amine.
- 11. The compound as defined in claim 1, which is 7-chloro-N-(phenylmethylidene)-3,4-dihydro-1H-pyrano[4,3-b]quinolin-10-amine.
- 12. The compound as defined in claim 1, which is N-[(4-nitrophenyl)methylidene]-3,4-dihydro-1H-pyrano[4,3-b]quinolin-10-amine.
- 13. The compound as defined in claim 1, which is N-(phenylmethylidene)-3,4-dihydro-2H-pyrano[3,2-b]quinolin-10-amine.
- 14. The compound as defined in claim 1, which is N-(phenylmethylidene)-1,2-dihydro-4H-pyrano[3,4-b]quinolin-10-amine.
- 15. The compound as defined in claim 1, which is N-(phenylmethylidene)-2,3-dihydrothieno[3,2-b]quinolin-9-amine.
- 16. The compound as defined in claim 1, which is 6-fluoro-N-(phenylmethylidene)-2,3-dihydrothieno[3,2-b]quinolin-9-amine.
- 17. The compound as defined in claim 1, which is N-[(2-thienyl)methylidene]-2,3-dihydrothieno[3,2-b]quinolin-9-amine.
- 18. The compound as defined in claim 1, which is N-[(2-pyridinyl)methylidene]-2,3-dihydrothieno[3,2-b]quinolin-9-amine.
- 19. The compound as defined in claim 1, which is N-hexylidene-2,3-dihydrothieno[3,2-b]quinolin-9-amine.
- 20. The compound as defined in claim 1, which is N-dodecylidene-2,3-dihydrothieno[3,2-b]quinolin-9-amine.
- 21. The compound as defined in claim 1, which is N-(phenylmethylidene)-1,3-dihydrothieno[3,4-b]quinolin-9-amine.
- 22. The compound as defined in claim 1, which is 7-methyl-N-(phenylmethylidene)-1,3-dihydrothieno[3,4-b]quinolin-9-amine.
- 23. The compound as defined in claim 1, which is N-[(4-pyridinyl)methylidene]-1,3-dihydrothieno[3,4-b]quinolin-9-amine.
- 24. The compound as defined in claim 1, which is N-[(3-pyridinyl)methylidene]-1,3-dihydrothieno[3,4-b]quinolin-9-amine.
- 25. The compound as defined in claim 1, which is N-tetradecylidene-1,3-dihydrothieno[3,4-b]quinolin-9-amine.
- 26. The compound as defined in claim 1, which is N-octadecylidene-1,3-dihydrothieno[3,4-b]quinolin-9-amine.
- 27. A pharmaceutical composition for enhancing the cholingeric function in a mammal which consists essentially of an effective amount of a compound as defined in claim 1 and a suitable carrier therefor.
- 28. The pharmaceutical composition as defined in claim 27 which consists essentially of N-(phenylmethylidene)-3,4-dihydro-1H-thiopyranoquinolin-10-amine and a suitable carrier therefor.
- 29. The pharmaceutical composition as defined in claim 27 which consists essentially of N-(phenylmethylidene)3,4-dihydro-1H-pyranoquinolin-10-amine and a suitable carrier therefor.
- 30. The pharmaceutical composition as defined in claim 27 which consists essentially of N-dodecylidene-2,3-dihydrothienoquinolin-9-amine and a suitable carrier therefor.
- 31. The pharmaceutical composition as defined in claim 27 which consists essentially of N-(phenylmethylidene)-1,3-dihydrothienoquinolin-9-amine and a suitable carrier therefor.
- 32. A method of increasing the cholinergic function in a mammal which comprises administering to the mammal in need of enhancement of cholinergic function an effective cholinergic function enhancing amount of a compound as defined in claim 1.
- 33. The method as defined in claim 32, which comprises the administration of N-(phenylmethylidene)-3,4-dihydro-1H-thiopyranoquinolin-10-amine.
- 34. The method as defined in claim 32, which comprises the administration of N-(phenylmethylidene)-3,4-dihydro-1H-pyranoquinolin-10-amine.
- 35. The method as defined in claim 32, which comprises the administration of N-dodecylidene-2,3-dihydrothienoquinolin-9-amine.
- 36. The method as defined in claim 32, which comprises the administration of N-(phenylmethylidene)-1,3-dihydrothienoquinolin-9-amine.
Parent Case Info
This is a division of a pending prior application, Ser. No. 480,388, filed Feb. 15, 1990, now U.S. Pat. No. 5,037,833, which is a continuation-in-part of a prior application, Ser. No. 223,848, filed Jul. 25, 1988, now abandoned, which is a continuation-in-part of a prior application, Ser. No. 094,181, filed Sep. 8, 1987, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
4695573 |
Shutske et al. |
Sep 1987 |
|
4843079 |
Shutske et al. |
Jun 1989 |
|
Divisions (1)
|
Number |
Date |
Country |
Parent |
480388 |
Feb 1990 |
|
Continuation in Parts (2)
|
Number |
Date |
Country |
Parent |
223848 |
Jul 1988 |
|
Parent |
94181 |
Sep 1987 |
|