9-fluoro-prostaglandin derivatives, process for their...

C - Chemistry – Metallurgy – 07 – C

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260/235.01

C07C 405/00 (2006.01)

Patent

CA 1218060

ABSTRACT OF THE DISCLOSURE Novel 9-fluoro-prostane derivatives of the general formula I Image (I) in which R1 represents a -CH2OH group, or represents a group of the formula Image , in which R2 represents a hydrogen atom or an alkyl group with 1 to 4 carbon atoms, or represents a group of the formula Image , in which R3 represents a C1-C10 acyl group or a methyl sulphonyl or an isopropyl sul- phonyl group or stands for R2, A represents a -CH2-CH2- group or a cis-CH=CH- group, B represents a -CH2-CH2- group, a trans- CH=CH- group or a -C?C- group, W represents a free or func- tionally modified hydroxy methylene group in which the hydroxyl group is in the ?- or .beta. -position, D and E together represent a direct bond or D represents a straight-chain or branched- chain bivalent aliphatic hydrocarbon group containing up to 10 carbon atoms which may be substituted by at least one fluorine atom and E represents an oxygen or sulphur atom, a direct bond, a -C?C- group or a group of the formula -CR6=CR7- in which R6 and R7 have different meanings and each represents a hydrogen atom, a chlorine atom or an alkyl group, R4 repre- sents a free or functionally modified hydroxyl group, R5 represents a hydrogen atom, or a straight chained or branched saturated or unsaturated alkyl group with 1 to 6 carbon atoms or when E is oxygen, represents a phenyl group, and the fluor- ine atom in the 9-position is in the ?- or .beta.- position with the proviso that D-E-R5 is other than n-pentyl when W is hydr- oxymethylene or RO-methylene, B is trans-CH=CH-, is bis-CH=CH-, R1 is -COOH or -COOCH3, and R is H or tetrahydropyranyl or a physiologically tolerable salt thereof with a base where R1 represents a group of the formula Image in which R2 repre- sents a hydrogen atom. The 9-fluoro-prostane derivatives and pharmaceutically acceptable salts thereof have inter alia a luteolytic and abortive activity and may accordingly be made up into pharmaceutical preparations with suitable carriers.

405837

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