Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and) 1,3A,8)-di(and tri)methylpyrrolo(2,3-B)indoles, compositions and use

US4791107A · kind A · utility

Assignee

• Hoechst Roussel Pharmaceuticals · US

Inventors

• R. Richard L. Hamer · Far Hills, US
• Grover C. Helsley · Pluckemin, US
• Edward J. Glamkowski · Hackettstown, US
• Yulin Chiang · Clay, US

Key dates

• Filing date: May 15, 1987
• Grant date: Dec 13, 1988
• Expiry date: May 15, 2007

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P25/28
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

There are described compounds of the formula ##STR1## where (a) X is O or S; PA1 (b) R is H, loweralkyl, ##STR2## where Y is O or S; R.sub.2 is alkyl, cycloalkyl, bicycloalkyl, cycloalkenyl, aryl, arylloweralkyl, heteroaryl or heteroarylloweralkyl, R.sub.3 is H or alkyl, or the group --NR.sub.2 R.sub.3 taken as a whole is 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 4-thiomorpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl or 2-(2,6-dichlorophenylimino)-1-imidazolidinyl) and R.sub.4 is hydrogen, loweralkyl, arylloweralkyl, diarylloweralkyl, aryl or heteroaryl, PA1 (c) m is 1 or 2; PA1 (d) each Z is independently H, loweralkyl, halogen, nitro, --NH.sub.2, loweralkylcarbonylamino, arylcarbonylamino, loweralkoxycarbonylamino or loweralkylamino, and PA1 (e) R.sub.1 is H, loweralkyl, arylloweralkyl, heteroarylloweralkyl, cycloalkylmethyl or loweralkenylmethyl, with the proviso that when X is O, m is 1, Z is H and R.sub.1 is methyl, R is not --CONHCH.sub.3, --CONHC.sub.6 H.sub.5, hydrogen, methyl or ethyl, and that when X is O, m is 1 and Z and R.sub.1 are both hydrogen, R is not hydrogen or methyl, and pharmaceutically acceptable acid addition salts thereof which are useful as memory-en…