9-deoxy-9a-methylene isosters of pgi.sub.2 and process for...

C - Chemistry – Metallurgy – 07 – D

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260/235.01

C07D 317/14 (2006.01) C07D 257/04 (2006.01) C07C 177/00 (1985.01)

Patent

CA 1198418

ABSTRACT The invention relates to novel compounds of formula I Image I wherein R is (a) a free or esterified carboxy group; (b) -C(OR')3, where each R' group is independently C1-C6-alkyl or phenyl; (c) -CH2-R", where R" is hydroxy or C2-C7-alkoxy; (d) Image , where Ra and Rb are chosen inde- pendently from the group hydrogen, C1-C6-alkyl, C2-C6-alkanoyl and phenyl; (e) -C=N; (f) a Image radical; (g) -CHO; or (h) a Image , radical where each X' is independently -O- or -S- and the R'a and R'b groups, whether the same or different, are C1-C6-alkyl or together form a straight or branched C2-C6-alkenylene chain; is: -CH2-, ?CH-OH, Image (cis), Image (trans), -C=C-, ,?C=O, -O-, -S-, or ?N-RC, where Rc may be hydro- gen, C1-C6-alkyl or C2-C6-alkanoyl; one of R1 and R2 and, independently, one of R3 and R4 is hydrogen, C1-C6-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, phenyl, or aryl-C1-C6-alkyl and the other is hydrogen, hydroxy, C1-C6-alkoxy or aryl- C1-C6-alkoxy, or, R1 and R2 and, independently, R3 and R4 together form an oxo group; each R5 and R6, whether the same or different, may be hydrogen, C1-C6-alkyl or halogen, or R5, R6 and the carbon atom to which they are bound form a ?C=CH2 or Image radical; Y is: -CH2-CH2-, Image (trans), Image (cis) where Z is hydrogen; X is: -(CH2)m3- in which m3 is zero or 1, Image (cis), Image (trans), -O-, -S-, or ?N-RC where Rc is as defined above; m1, m2, n1 and n2, whether the same or different, may be zero or an integer between 0 and 12 such that each m1 + m2 and n1 + n2 is less than or equal to 15; p and q are independently zero or an integer between l and 3 such that the sum p q is an integer of l to 6; R7 is a cycloaliphatic radical, either unsubstituted or substituted with one or more C1-C6-alkyl or C1-C6-alkoxy; or a saturated or unsaturated heterocyclic ring, either unsubstituted or substituted with one or more of the following: halogen, halo-C1-C6-alkyl, C1-C6-alkoxy, phenyl, C1-C6- alkyl; and the lactones derived from compounds of formula I and the pharm- aceutically or veterinarily acceptable salts thereof. The compounds display bronchodilator, luteolytic, anti-ulcerogenic and platelet anti-aggregant activity.

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