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US 5,025,034 AGranted
Prostaglandins
AssigneeNational Research Development Corporation
InventorsRobert L. Jones, Norman H. Wilson
Life of this patent
Estimating the term…
Abstract
Prostaglandin analogues exhibiting activity at thromboxane receptor sites have been prepared.
Claims36
A compound of the formula (I)
- represents one of the divalent groups ##STR74## the letters a and b indicating in each case the points of attachment of the substituents R.sup.1 and C(R.sup.2).dbd.NR, respectively:
- wherein
- R.sup.1 is a group of the formula R'--COQ where R' is selected from the group consisting of --(CH.sub.2).sub.j -- where j is an integer from 4 to 8;
- --CH.dbd.CH--(CH.sub.2).sub.k --, where k is 2 or 3;
- --CH.sub.2 --CH.dbd.CH--(CH.sub.2).sub.m --, where m is an integer from 1 to 5;
- --CH.sub.2 --CH.sub.2 --CH.dbd.CH--(CH.sub.2).sub.n --, where n is 0 or an integer from 1 to 4;
- --X--(CH.sub.2).sub.p --, where p is an integer from 3 to 7;
- --CH.sub.2 --X--(CH.sub.2).sub.q --, where q is an integer from 2 to 6;
- and CH.sub.2 --CH.sub.2 --X--(CH.sub.2).sub.m --, where X is O or S;
- and COQ is carboxy, a physiologically acceptable carboxylate salt, a C.sub.1 -C.sub.5 alkyl ester or CONHSO.sub.2 CH.sub.3 ;
- R.sub.2 is selected from the group consisting of hydrogen, C.sub.1-10 aliphatic hydrocarbon groups, and C.sub.1-10 aliphatic hydrocarbon groups substituted by Ar, OAr or SAr, where Ar represents a phenyl, naphthyl, fluorenyl, dibenzocyclohexyl, dibenzocycloheptyl, pyridyl, benzthiazolyl, dihydrobenzthiazolyl, N-methyldihydrobenzthiazolyl, benzoxazolyl, dihydrobenzoxazolyl or N-methydihydrobenzoxazolyl group or such a group substituted by one or more substituents selected from C.sub.1-10 alkoxy, halogen, C.sub.1-10 halogen-substituted alkyl, sulphamoyl, amino, hydroxyl, nitro and C.sub.1-10 alkyl groups;
- and
- R is a group --OR.sup.3, --OR.sup.4, --A--R.sup.3 or --N.dbd.R.sup.5 in which A is --NH--, --NH.CO--, --NH.CO.CH.sub.2 N(R.sup.6)--, --NH.SO.sub.2 --, --NH.CO.NH-- or --NH.CS.NH-- and wherein R.sup.3 is a C.sub.1-10 aliphatic hydrocarbon group, a group Ar or a C.sub.1-10 aliphatic hydrocarbon group substituted by one or more groups selected from Ar, OAr, and SAr;
- R.sup.4 is a C.sub.1-10 aliphatic hydrocarbon group which is substituted through an oxygen atom by a C.sub.1-10 aliphatic hydrocarbon group which is itself substituted by one or more groups Ar;
- R.sup.5 is a C.sub.1-10 aliphatic hydrocarbon group, a group Ar', where Ar' represents a fluorenylidene, dibenzocyclohexylidene, dibenzocycloheptylidene, dihydrobenzthiazolylidene, N-methyldihydrobenzthiazolylidene, dihydrobenzoxazolylidene or N-methyldihydrobenzoxazolylidene group or such a group substituted on a benzene ring or rings thereof by one or more substituents selected from C.sub.1-10 alkoxy, halogen, C.sub.1-10 halogen-substituted alkyl, sulphamoyl, amino, hydroxyl, nitro and C.sub.1-10 alkyl groups, or a C.sub.1-10 aliphatic hydrocarbon group substituted by one or more groups selected from Ar, OAr and SAr;
- an R.sup.6 is hydrogen, a C.sub.1-10 aliphatic hydrocarbon group, a group Ar or a C.sub.1-10 aliphatic hydrocarbon group substituted by one or more groups selected from Ar, POAr and SAr.
13 more elements
A compound according to claim 44, in which R.sup.1 and C(R.sup.2).dbd.NR are in a trans relationship.
Dependencies are inferred from the claim text.