N-(pyrrol-1-yl)pyridinamines having memory enhancing activity

Details N-(pyrrol-1-yl)pyridinamines having memory enhancing activity N-(pyrrol-1-yl)pyridinamines having memory enhancing activity

1986-11-12

1988-12-20

Rotman, Alan L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

546281, C07D40102, A61K 3144

Patent

active

047925620

ABSTRACT:
There are disclosed novel compounds of the formula ##STR1## 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, ##STR2## --CH.sub.2 CHR.sub.6 R.sub.7, --CH.sub.2 CH.sub.2 CN, --CH.sub.2 CH.sub.2 OCH.sub.3, --CH.sub.2 CH.sub.2 CO.sub.2 C.sub.2 H.sub.5, ##STR3## 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 whole being ##STR4## and R.sub.3 is hydrogen, NO.sub.2, NH.sub.2, halogen, loweralkanoylamino, arylloweralkanoylamino, aroylamino or loweralkyl; 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, which are useful for enhancing memory, methods for synthesizing them, pharmaceutical compositions comprising an effective memory enhancing amount of such a compound and a method of treating a patient in need of memory enhancement which comprises administering such a compound to the patient.

REFERENCES:
Flitsch et al., Chem. Ber., 102, pp. 3268-3276 (1969).
Petrow, J. Chem. Soc., pp. 927-928 (1945).
Epton, Chemistry and Industry, pp. 425-426 (1965).
Wesseling et al., New England Journal of Medicine, vol. 310 (15), pp. 988-989 (1984).
Delarge et al., Eur. J. Med.--Chima Therapeutica, vol. 5 (4), pp. 299-304, Jul.-Aug. 1980.
Miller et al., J. Med. Chem., vol. 13 (5) pp. 1022-1023 (1970).

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