Fluoro-prostaglandins and process for their preparation

C - Chemistry – Metallurgy – 07 – D

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260/235.03

C07D 319/12 (2006.01) C07C 405/00 (2006.01) C07D 307/935 (2006.01) C07D 309/12 (2006.01)

Patent

CA 1103663

ABSTRACT OF THE DISCLOSURE This invention relates to optically active or racemic compounds having the following formula (I) Image (I) wherein R is a member selected from the group consisting of hydrogen, a C1-C12 alkyl group and a cation of a pharmaceutically acceptable base; the symbol - - - - represents a single or a double bond, wherein, when the symbol - - - - is a double bond, R3 is a hydrogen atom and R1 and R2 together form an oxo group, while, when the symbol - - - - is a single bond, R3 is hydroxy, and one of R1 and R2 is hydrogen and the other is hydroxy or acyloxy or R1 and R2, taken together, form an oxo group; A is trans-CH=CH- or -C?C-; one of R4 and R5 is hydroxy and the other is hydrogen; R6 is a member selected from the group consisting of hydrogen, methyl and fluorine; n is zero, or an integer of 1 to 6; R7, when A is trans-CH=CH-, is a cycloalkyl group containing 3 to 7 ring carbon atoms, while, when A is -C?C-, R7 is a member selected from the group consisting of methyl, cycloalkyl containing 3 to 7 ring carbon atoms and phenyl unsubstituted or optionally substituted by one or more substituents selected from the group consisting of halogen, C1-C6 alkoxy and trihalomethyl. The compounds of formula (I) may be used for the same therapeutical indica- tions as natural prostaglandins. In particular, the compounds of formula (I), wherein R2 and R3 are hydroxy, are provided with an outstanding lutcolytic activity, i.e. they are useful as abortive agents.

248218

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