摘要 |
1515540 4 - Amino - trans - decahydroquinoline derivatives LABAZ 24 Nov 1976 [16 Dec 1975] 51507/75 Heading C2C Novel trans decahydroquinoline derivatives of the Formula I and pharmaceutically acceptable acid addition salts thereof, wherein R<SP>1</SP> is alkyl, alkoxy, dialkylamino, a saturated heterocyclic ring attached through a ring nitrogen atom, an unsaturated heterocyclic group or an optionally substituted phenyl, R<SP>2</SP> is alkyl, optionally substituted phenyl, naphthyl, unsaturated heterocyclic optionally substituted by alkyl, aralkyl, aralkenyl or alicyclic and R<SP>3</SP> is alkyl substituted furyl, aralkyl, aralkenyl or a group where A is C 1-4 -alkylene, Y is oxygen, sulphur, carbonyl > C = NOH, >C = NNH 2 or sulphoxide or a group X R<SP>4</SP> and R<SP>5</SP> each are hydrogen, halogen, methyl, methoxy or acetyl and n is zero or 1, with the proviso that when n is zero, Y is carbonyl, where alkyl groups unless otherwise specified have 1 to 4 carbon atoms, may be prepared, when R 1 is other than dialkylamino or saturated heterocyclic group attached by a ring nitrogen atom and when R<SP>3</SP> is a group II, Y is other than hydroxyiminomethylene or hydrazonomethylene by reacting a compound III with R<SP>1</SP>COCl or (R<SP>1</SP>CO) 2 O or when R<SP>1</SP> is dialkylamino or a saturated heterocyclic group attached by a ring nitrogen atom, and when R<SP>3</SP> is a group II, Y is other than hydroxyiminomethylone or hydrazonomethylene by reacting a compound VI with an amine R<SP>1</SP>H, optionally followed by acid addition salt formation and/or reacting a carbonyl at Y with hydroxylamine or hydrazine to form a hydroxylimino methylene or a carbonyl hydrazonomethylene. Intermediates of the Formula III are prepared by reacting 4-oxo-trans-decahydroquinoline with an amine R<SP>2</SP>NH 2 and reducing the imine so formed to produce a compound VIII which is reacted with R<SP>3</SP>-Hal, where Hal is chlorine, bromine or iodine. When R<SP>3</SP> is a group II and Y is carbonyl, the carbonyl group is protected with a group X and thereafter optionally hydrolysed. The isomers of the compound VIII are separated. Pharmaceutical compositions of the compounds I with the usual excipients show analgesic activity when administered orally, parenterally or rectally. The compounds I in which R<SP>1</SP> is alkoxy also show antihypertensive action. |