15-epi-prostacyclin and analogous prostacyclins and process...

Details 15-epi-prostacyclin and analogous prostacyclins and process... 15-epi-prostacyclin and analogous prostacyclins and process...

C - Chemistry, Metallurgy

07

D

260/235.01

C07D 257/04 (2006.01) C07C 405/00 (2006.01) C07D 307/935 (2006.01) C07D 307/937 (2006.01) C07D 311/94 (2006.01)

Patent

CA 1198416

Abstract of the Disclosure The invention is bicyclic prostagiandi.ns of formula I Image (I) tI) wherein R is a substituent chosen from the following: a) -COOR' wherein R' is hydrogen or C1 - C6 alkyl; b) -CH2OH; c) Image in which the R" groups, whether the same or different, are C1 - C6 alkyl or phenyl; d) Image , in which Ra and Rb are independently chosen from hydrogen, C1 - C6 alkyl, C2 - C6 alkanoyl and phenyl; d) Image f) -C=N; p is zero or an integer between 1 and 7; q is 1 or 2; R1 is hydrogen, hydroxy, C1 - C6 alkoxy, aryl-C1 - C6 alkoxy, acyloxy Y is chosen from the group: -CH2-CH2-- -C=C-, Image (cis), Image (trans) where Z1 is hydrogen or halogen; R2 is hydrogen, C1 - C6 alkyl, C2 - C6 alkenyl, C2 - C6 alkynyl, aryl; R5 is hydrogen, C1 - C6 alkyl, aryl-C1 - C6 alkyl; n1 and n2, whether the same or different, are zero or an integer between 1 and 6; R3 and R4, whether the same or different, may be hydrogen, C1 - C6 alkyl or fluorine, or may form a -C- or -C- group with a carbon atom to which they are bound CH2 CH2-CH2 X is chosen from -O-, -S- and -(CH2)m wherein m is zero or 1; R6 is a substituent chosen from a') hydrogen, b') C1 - C4 alkyl; c') a cycloaliphatic radical, optionally substituted with one or more C1 - C6 alkyl and C1 - C6 alkoxy groups; d') an aryl group optionally substituted with one or more halogen, C1 - C6 alkyl, halo-C1 - C6 alkyl or C1 - C6 alkoxy; e') a saturated or unsaturated heterocyclic radical optionally substituted with one or more halogen, C1 - C6 alkyl, C1 - C6 alkoxy, or halo-C1 - C6 alkyl, and a pharmaceutically or veterinarily acceptable salt thereof, which process comprises dehydrohalogenating a compound of formula(II) (II) Image wherein R, P q, R1, Y, R2, R5, n1, R3, R4, X, n2 and R6 are as defined above and Z2 is a halogen atom, and, if required, converting a compound of formula (I) into another compound of formula (I), or, if required, transforming a compound of formula (I) into a pharmaceutically or veterinarily acceptable salt or, if required) resolving a mixture of isomers into the single isomers. The compounds display the ability to inhibit platelet aggregation, to dissolve clots and to cause the coronary vessels to dilate.

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