Centrally acting 6,7,8,9-tetrahydro-3H-benz(e) indole heterocyclics

US5650427A · kind A · utility

Assignee

• The Upjohn Co. · US

Inventors

• Hakan V. Wikstrom · Mölndal, SE
• Per A. E. Carlsson · Göteborg, SE
• Bengt R. Andersson · Göteborg, SE
• Kjell A. I. Svensson · Alingsås, SE
• Stig T. Elebring · Mölndal, SE
• Nils P. Stjernlof · Mölndal, SE
• Arthur Glenn Romero · Kalamazoo, US
• Susanne R. Haadsma-Svensson · Portage, US
• Chiu-Hong Lin · Kalamazoo, US
• Michael Ennis · Mattawan, US

Key dates

• Filing date: Jun 2, 1995
• Grant date: Jul 22, 1997
• Expiry date: Jun 2, 2015

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D491/04
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

A compound of Formula I ##STR1## or pharmaceutically acceptable salts of Formula I, where R.sup.1 is H, C.sub.1 -C.sub.3 alkyl, --(CH.sub.2).sub.n CONH.sub.2 where n is 2 to 6, (CH2).sub.n -1-(4,4-dimethylpiperidine-2,6-dione-yl), or cyclopropylmethyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl or combined with R.sup.1 to form a C.sub.3 -C.sub.8 cycloalkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 akynyl, (CH.sub.2).sub.n --X--Ar where X is O, S, or NH, 3,3,3-trifluoropropyl, --(CH.sub.2).sub.m --R.sup.9 where m is 2 or 3 and R.sup.9 is phenyl, 2-thiophenyl or 3-thiophenyl; R.sup.3 is hydrogen, C.sub.1 -C.sub.3 alkyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, formyl, CN, halogen, CH.sub.2 OR.sup.2, C(O)C(O)OR.sup.1, C(O)CO NR.sup.1 R.sup.2, --(CH.sub.2).sub.q --NR.sup.1 R.sup.2 where q is 0 to 5, C.dbd.NOR.sup.2, 2(4,5-dihydro)oxazolyl, or COR.sup.10 where R.sup.10 is H, R.sup.1, NR.sup.1 R.sup.2 or CF.sub.3 ; R.sup.4 is hydrogen, C.sub.1 -C.sub.3 alkyl, cyclopropylmethyl, CF.sub.3, 2,2,2-trifluoroethyl, CN, CONR.sup.1 R.sup.2, .dbd.O, 2(4,5-dihydro)imidazolyl, 2(4,5-dihydro)oxazolyl, 2-oxazolyl, 3-oxadiazolyl, or 3,3,3-trifluoropropyl; R.sup.5 is…