Von Prostaglandinen abgeleitete Verbindungen und Verfahren zu ihrer Herstellung

• Main Author: EDWARD PIKE,JOHN
• Format: Patent
• Language: German
• Published: 10.07.1969
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY

1,172,200. Prostaglandins. UPJOHN CO. 9 Oct., 1968 [9 Oct., 1967], No. 47885/68. Heading C2C. Novel compounds of the Formulµ III, IV and I are prepared from compounds of the Formula II by the process shown below in which X is -CH 2 CH 2 or trans -CH= CH- and both Y and Z are -CH 2 CH 2 , or X is trans -CH = CH--, Y is cis -CH=CH and Z is -CH 2 CH 2 - or cis -CH=CH-; m is 0, 1 or 2; n is 2, 3, 4 or 5; R 1 is H or C 1-8 alkyl; and Q is a group which, with -N= on hydrolysis with nitrous acid yields an oxo group, e.g. -OH, -O-C 1-4 alkyl, -NHCONH 2 or -NRCSNR 2 . Conversion of II to III is effected with the appropriate reagent, i.e. hydroxylamine &c., III is reduced to IV with lithium aluminium hydride, lithium borohydride or diisobutyl aluminium hydride, and IV is hydrolysed with nitrous acid, preferably formed in situ. Compounds I may be acylated with carboxylic acids to give their novel tri-acylates. The compounds of the Formula I and their triacylates are stated to be antagonists of epinephrine-induced mobilization of free fatty acids and to be active in inhibiting blood platelet aggregation and thrombus formation, and they may be made up into pharmaceutical compositions with suitable carriers.