Claims
- 1. A compound of the formula ##STR34## where n is 0 or 1; R is hydrogen or loweralkyl; R.sub.1 is hydrogen, loweralkyl, halogen, cyano, loweralkanoyl, arylloweralkanoyl, aroyl, --CH(OH)R.sub.4, --C(OH)R.sub.4 R.sub.5 or --CH.sub.2 OR.sub.5, --CH.dbd.CR.sub.6 R.sub.7, --CH.dbd.CHCN, --CH.dbd.CHOCH.sub.3, --CH.dbd.CHCO.sub.2 C.sub.2 H.sub.5, ##STR35## R.sub.4 being hydrogen, loweralkyl, arylloweralkyl or aryl, R.sub.5 being loweralkyl, aryl or arylloweralkyl, R.sub.6 being hydrogen or loweralkyl and R.sub.7 being hydrogen, loweralkyl or aryl; R.sub.2 is hydrogen, loweralkyl, loweralkenyl, loweralkynyl, --CH.sub.2 CO.sub.2 C.sub.2 H.sub.5, arylloweralkyl, phenyl, nitrophenyl, cyanophenyl, trifluoromethylphenyl, aminophenyl, loweralkanoylaminophenyl, loweralkoxycarbonyl, arylloweralkoxycarbonyl, aryloxycarbonyl, loweralkylaminocarbonyl, arylloweralkylaminocarbonyl, arylaminocarbonyl, alkanoyl, arylloweralkanoyl, aroyl, alkenoyl, alkynoyl, --CH.sub.2 C.tbd.CCH.sub.2 --NR'R", --CH.sub.2 CH.dbd.CHCH.sub.2 --NR'R" or --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --NR'R", R' and R" being independently loweralkyl or --NR'R" taken as a hole being ##STR36## and R.sub.3 is hydrogen, NO.sub.2, NH.sub.2, halogen, loweralkanoylamino, arylloweralkanoylamino, aroylamino or loweralkyl; the term aryl in each occurrence signifying a phenyl group having 0, 1, 2, or 3 substituents each of which being independently loweralkyl, loweralkoxy, halogen, CF.sub.3, NO.sub.2 or CN; with the proviso that when n is 0, R.sub.2 is phenyl, R.sub.3 is hydrogen and the pyridine moiety is 2-pyridinyl, R and R.sub.1 may not be 2-methyl and 5-methyl; or pharmaceutically acceptable acid addition salts thereof.
- 2. The compound as defined in claim 1 where R.sub.3 is H.
- 3. The compound as defined in claim 1 where R.sub.2 is H, loweralkyl, loweralkenyl, loweralkynyl, arylloweralkyl or --CH.sub.2 C.tbd.CCH.sub.2 --NR'R".
- 4. The compound as defined in claim 1 where R.sub.1 is H, loweralkyl, halogen, loweralkanoyl, --CH(OH)R.sub.4, --CH.dbd.CR.sub.6 R.sub.7 or --CH.dbd.CHOCH.sub.3, where R.sub.4 is H or loweralkyl, R.sub.6 is H or loweralkyl and R.sub.7 is H, loweralkyl or aryl.
- 5. The compound as defined in claim 2 where R.sub.2 is H, loweralkyl, loweralkenyl, loweralkynyl, arylloweralkyl or --CH.sub.2 C.tbd.CCH.sub.2 --NR'R", and R.sub.1 is H, loweralkyl, halogen, loweralkanoyl, --CH(OH)R.sub.4, --CH.dbd.CR.sub.6 R.sub.7 or --CH.dbd.CHOCH.sub.3, where R.sub.4 is H or loweralkyl, R.sub.6 is H or loweralkyl and R.sub.7 is H, loweralkyl or aryl.
- 6. The compound as defined in claim 1, where the pyridine ring is connected to the amino nitrogen via the 4-position.
- 7. The compound as defined in claim 3, where the pyridine ring is connected to the amino nitrogen via the 4-position.
- 8. The compound as defined in claim 4, where the pyridine ring is connected to the amino nitrogen via the 4-position.
- 9. The compound as defined in claim 5, where the pyridine ring is connected to the amino nitrogen via the 4-position.
- 10. The compound as defined in claim 1, which is N-(butyl)-N-(1H-pyrrol-1-yl)-4-pyridinamine.
- 11. The compound as defined in claim 1, which is N-(2-propenyl)-N-(1H-pyrrol-1-yl)-4-pyridinamine.
- 12. The compound as defined in claim 1, which is N-(2-propynyl)-N-(1H-pyrrol-1-yl)-4-pyridinamine.
- 13. The compound as defined in claim 1, which is N-[4-(pyrrolidin-1-yl)-2-butynyl]-N-(1H-pyrrol-1-yl)-4-pyridinamine.
- 14. The compound as defined in claim 1, which is N-(2-chloro-1H-pyrrol-1-yl)-N-propyl-4-pyridinamine.
- 15. The compound as defined in claim 1, which is N-(2-ethenyl-1H-pyrrol-1-yl)-N-methyl-4-pyridinamine.
- 16. The compound as defined in claim 1, which is N-[2-(1-propenyl)-1H-pyrrol-1-yl]-N-methyl-4-pyridinamine.
- 17. The compound as defined in claim 1, which is N-[2-(2-phenylethenyl)-1H-pyrrol-1-yl]-N-methyl-4-pyridinamine.
- 18. The compound as defined in claim 1, which is N-[2-(2-methoxyethenyl)-1H-pyrrol-1-yl]-N-methyl-4-pyridinamine.
- 19. The compound as defined in claim 1, which is N-(2-ethyl-1H-pyrrol-1-yl)-N-methyl-4-pyridinamine.
- 20. The compound as defined in claim 1, which is N-(methyl-N-(2-propyl-1H-pyrrol-1-yl)-4-pyridinamine.
- 21. The compound as defined in claim 1, which is N-methyl-N-(2-phenylethyl-1H-pyrrol-1-yl)-4-pyridinamine.
- 22. The compound as defined in claim 1, which is 4-nitro-N-(1H-pyrrol-1-yl)-3-pyridinamine-N-oxide.
- 23. The compound as defined in claim 1, which is N-methyl-N-(1H-pyrrol-1-yl)-4-nitro-3-pyridinamine-N-oxide.
- 24. The compound as defined in claim 1, which is 3-[N-methyl-N-(1H-pyrrol-1-yl)9 -3,4-pyridinediamine.
- 25. The compound as defined in claim 1, which is N-(2-cyano-1H-pyrrol-1-yl)-N-methyl-4-pyridinamine.
- 26. The compound as defined in claim 1, which is N-methyl-N-(2-methyl-1H-pyrrol-1-yl)-4-pyridinamine.
- 27. The compound as defined in claim 1, which is N-propyl-N-(2-methyl-1H-pyrrol-1-yl)-4-pyridinamine.
- 28. The compound as defined in claim 1, which is N-methyl-N-(2,5-dimethyl-1H-pyrrol-1-yl)-4-pyridinamine;
- 29. The compound as defined in claim 1, which is N-methyl-N-[2-[2-(2-methylphenyl)ethenyl]-1H-pyrrol-1-yl]-4-pyridinamine.
- 30. The compound as defined in claim 1, which is N-ethyl-N-[2-[2-(4-methylphenyl)ethenyl]-1H-pyrrol-1-yl]-4-pyridinamine.
- 31. The compound as defined in claim 1, which is N-methyl-N-[2-[2-(2-methoxyphenyl)ethenyl]-1H-pyrrol-1-yl]-4-pyridinamine.
- 32. The compound as defined in claim 1, which is N-propyl-N-[2-[2-(3-methoxyphenyl)ethenyl]-1H-pyrrol-1-yl]-4-pyridinamine.
- 33. The compound as defined in claim 1, which is N-methyl-N-[2-[2-(4-methoxyphenyl)ethenyl]-1H-pyrrol-1]-4-pyridinamine.
- 34. The compound as defined in claim 1, which is N-methyl-N-[2-[2-(2-chlorophenyl)ethenyl]-1H-pyrrol-1-yl-4-pyridinamine.
- 35. The compound as defined in claim 1, which is N-methyl-N-[2-[2-(4-chlorophenyl)ethenyl]-1H-pyrrol-1-yl]-4-pyridinamine.
- 36. The compound as defined in claim 1, which is N-methyl-N-[2-[2-(2-methylphenyl)ethyl]-1H-pyrrol-1-yl]-4-pyridinamine.
- 37. The compound as defined in claim 1, which is N-ethyl-N-[2-[2-(3-methylphenyl)ethyl]-1H-pyrrol-1-yl]-4-pyridinamine.
- 38. The compound as defined in claim 1, which is N-propyl-N-[2-[2-(3-methoxyphenyl)ethyl]-1H-pyrrol-1-yl]-4-pyridinamine.
- 39. The compound as defined in claim 1, which is N-methyl-N-[2-[2-(4-methoxyphenyl)ethyl]-1H-pyrrol-1-yl]-4-pyridinamine.
- 40. The compound as defined in claim 1, which is N-ethyl-N-[2-[2-(2-chlorophenyl)ethyl]-1H-pyrrol-1-yl]-4-pyridinamine.
- 41. The compound as defined in claim 1, which is N-methyl-N-[2-[2-(4-methoxyphenyl)ethyl]-1H-pyrrol-1-yl]-4-pyridinamine.
- 42. The compound as defined in claim 1, which is N-(1H-pyrrol-1-yl)-3-pyridinamine.
- 43. The compound as defined in claim 1, which is N-methyl-N-(1H-pyrrol-1-yl)-3-pyridinamine.
- 44. A pharmaceutical composition which comprises an effective memory enhancing amount of a compound as defined in claim 1 in admixture with an inert carrier.
- 45. A method of treating a patient in need of memory enhancement which comprises administering to the patient an effective memory enhancing amount of a compound as defined in claim 1.
Parent Case Info
This is a division of a prior application Ser. No. 926,593, filed Nov. 12, 1986, now U.S. Pat. No. 4,792,562, which in turn is a continuation-in-part of a prior application Ser. No. 804,430 filed Dec. 4, 1985, now U.S. Pat. No. 4,752,610.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
4631286 |
Shutske et al. |
Dec 1986 |
|
4670562 |
Martin et al. |
Jun 1987 |
|
4695573 |
Shutske et al. |
Sep 1987 |
|
Divisions (1)
|
Number |
Date |
Country |
Parent |
926593 |
Nov 1986 |
|
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
804430 |
Dec 1985 |
|