Bicyclic prostaglandins and process for their preparation
AssigneeFarmitalia Carlo Erba S.p.A.
InventorsCarmelo Gandolfi, Carlo Passarotti, Alessandro Andreoni, Angelo Fumagalli, Franco Faustini, Roberto Ceserani, Maria M. Usardi
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Abstract
Bicyclic prostaglandins and pharmaceutical and veterinary compositions containing them having numerous pharmaceutical or veterinary utilities, including, for example, hypotensive, vasodilatory, anti-aggregating, luteolytic, and cytoprotective activities. Processes for preparing the compounds and compositions are also disclosed.
Claims34
A compound of the formula ##STR53## wherein R.sub.c is H,C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is hydrogen or bromine;
- p is zero an integer of 1 to 7,
- Y is --CH.sub.2 --CH.sub.2 -- or ##STR54## one of R.sub.2 and R.sub.5 is hydrogen or C.sub.1 -C.sub.6 alkyl and the other is hydroxy;
- each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen or C.sub.1 -C.sub.6 alkyl;
- each of n.sub.1 and n.sub.2 which are the same or different is zero or an integer of 1 to 6;
- m is zero or 1;
- R.sub.6 is a C.sub.3 -C.sub.9 -cycloalkyl radical or a C.sub.3 -C.sub.9 -cycloalkenyl radical, unsubstituted or substituted by one or more substituents selected from the group consisting of C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy, and the pharmaceutically or veterinarily acceptable salts thereof.
A compound of the formula ##STR55## wherein R.sub.c is H,C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is hydrogen or bromine;
- p is zero an integer of 1 to b 7,
- Y is --CH.sub.2 --CH.sub.2 --
- one of R.sub.2 and R.sub.5 is hydrogen or C.sub.1 -C.sub.6 alkyl and the other is hydroxy;
- each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen or C.sub.1 -C.sub.6 alkyl;
- each of n.sub.1 and n.sub.2 which are the same or different is zero or an integer of 1 to 6;
- m is zero or 1;
- R.sub.6 is a C.sub.3 -C.sub.9 -cycloalkyl radical or a C.sub.3 -C.sub.9 -cycloalkenyl radical, unsubstituted or substituted by one or more substituents selected from the group consisting of C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy, and the pharmaceutically or veterinarily acceptable salts thereof.
A compound of the formula ##STR56## wherein R.sub.c is H,C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is hydrogen or bromine;
- p is zero an integer of 1 to 7,
- Y is ##STR57## one of R.sub.2 and R.sub.5 is hydrogen or C.sub.1 -C.sub.6 alkyl and the other is hydroxy;
- each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen or C.sub.1 -C.sub.6 alkyl;
- each of n.sub.1 and n.sub.2 which are the same or different is zero or an integer of 1 to 6;
- m is zero or 1;
- R.sub.6 is C.sub.3 -C.sub.9 -cycloalkyl radical or a C.sub.3 -C.sub.9 -cycloalkenyl radical, unsubstituted or substituted by one or more substituents selected from the group consisting of C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy, and the pharmaceutically or veterinarily acceptable salts thereof.
A compound selected from the group consisting of:
- 13t-6.beta.H-6(9.alpha.)-oxide-11.alpha.,15S-dihydroxy-17-cyclopentyl-18,19 ,20-trinor-prost-13-enoic acid methyl ester, and the corresponding free acid and pharmaceutically or veterinarily acceptable salts thereof;
- 13t-6.beta.H-6(9.alpha.)-oxide-11.alpha.,15S-dihydroxy-17-cyclohexyl-18,19, 20-trinor-prost-13-enoic acid methyl ester and the corresponding free acid and pharmaceutically or veterinarily acceptable salts thereof;
- 13t-6.beta.H-6,9.alpha.-oxide-11.alpha.,15S-dihydroxy-17-cyclohexyl-20,19,1 8-trinor-prost-13-enoic acid and the pharmaceutically or veterinarily acceptable salts thereof, as well as the corresponding methyl ester.
A compound 13t-5-bromo-6.beta.H-6(9.alpha.)-oxide-11.alpha.,15S-dihydroxy-17-cyclohex yl-18,19,20-trinor-prost-13-enoic acid methyl ester, and the corresponding free acid and the pharmaceutically or veterinarily acceptable salts thereof.
Dependencies are inferred from the claim text.