GB1326925A - 9-amino-alkyl-1,10-dihydro-9,10-etheno-anthracenes and process for their manufacture - Google Patents

Abstract

1326925 Aminoalkyl-9, 10-ethenoanthracenes CIBA-GEIGY AG 20 Nov 1970 [28 Nov 1969 5 Oct 1970] 55320/70 Heading C2C Novel optionally substituted 9-(R-alkyl)- 9,10 - dihydro - 9,10 - etheno - anthracenes, in which R is a secondary or tertiary amino group such as an amino group substituted by one or two lower alkyl or phenyl-lower alkyl residues or by one lower alkylene residue which may be interrupted by oxygen, sulphur or nitrogen atoms, and the aliphatic portion of the said substituents may also carry a hydroxyl group, the alkylene residue that links the amino group with the anthracene nucleus separates both these units by 1 to 3 carbon atoms, the etheno bridge is optionally lower alkyl substituted, the position 10 is unsubstituted or substituted by a halogen atom, or lower alkyl group and the positions 1-8 are unsubstituted or substituted by lower alkyl, alkoxy, alkenyloxy, alkylmercapto, alkanoyloxy, alkylsulphonyl, hydroxyl or trifluoromethyl groups or by halogen atoms, where "lower" denotes groups containing up to 8 carbon atoms and salts thereof, are prepared by one of the following methods: (a) compounds wherein R is NH 2 are substituted by reaction with a suitable reactive ester of an alcohol; (b) compounds wherein R is a reactive ester group are reacted with a suitable compound R-H; (c) reduction of a corresponding amide; (d) a 9 - oxoalkyl - 9,10 - dihydro - 9,10 - ethenoanthracene is reacted under reducing conditions with an amine H-R with optional isolation of the imine, or (e) a compound wherein R is NH 2 is reacted under reducing conditions with an aldehyde or ketone. # - (9,10 - Dihydro - 9,10 - etheno - 9 - anthryl)- propionic acid alkylamides are prepared by reaction of the alkylamine with the methyl ester of the above acid which is obtained by action of Zn/Cu on #-[11,12-dichloro-9,10-dihydro-9,10- ethano - 9 - anthryl] - propionic acid methyl ester prepared by action of trans-dichloroethylene on #-(9-anthryl)-propionic acid methyl ester. 9 - (Methyliminomethyl)- 9,10 - dihydro - 9,10- ethenoanthracene is obtained by action of methylamine on 9,10-dihydro-9,10-etheno-9-anthracene aldehyde prepared by action of Zn/Cu on 9,10- dihydro - 11,12 - dichloro - 9,10 - ethano - 9- anthracene aldehyde obtained by action of transdichloroethylene on 9-anthracene aldehyde. Pharmaceutical compositions in conventional forms for enteral or parenteral administration and having psychotropic, tranquillizing, antidepressive and sedative effects as well as promoting better feed utilization comprise an above novel compound or salt and a carrier or diluent therefor.