Prostaglandins
AssigneeNational Research Development Corporation
InventorsRobert L. Jones, Norman H. Wilson
Life of this patent
Estimating the term…
Abstract
Novel bicyclo [2,2,1] heptanes and hept-2Z-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by an aldoxime or ketoxime group which is O-substituted by an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. Such compounds may be prepared by the action of an oximating agent on an intermediate which is substituted at the 6-position by an aldehydic or ketonic carbonyl group. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.
Claims21
A compound which is a bicyclo[2,2,1]hept-2Z-ene substituted at the 5-position by a group of the formula --R.sup.1 --COQ, where R.sup.1 is selected from the group consisting of C.sub.4 -C.sub.8 alkyl;
- --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 an integer from 0 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;
- --CH.sub.2 --CH.sub.2 --X--(CH.sub.2).sub.m --;
- and
- --CH.dbd.CH--(CH.sub.2).sub.3 --;
- wherein X is O or S;
- COQ is carboxy, a physiologically acceptable carboxylate salt, a branched or unbranched C.sub.1 -C.sub.5 alkyl ester or CONHSO.sub.2 CH.sub.3 ;
- and wherein said bicyclo[2,2,1]heptene is substituted at the 6-position by a grouping of the formula ##STR42## in which R.sub.4 is selected from the group consisting of unsubstituted C.sub.1 -C.sub.10 branched or unbranched aliphatic hydrocarbon residues and C.sub.1 -C.sub.10 branched or unbranched aliphatic hydrocarbon residues substituted by Ar, --OAr, or --SAr, where Ar is a phenyl or pyridyl residue which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, halogen substituted C.sub.1 -C.sub.5 branched or unbranched alkyl groups, sulphonamido groups, amino groups, hydroxy and C.sub.1 -C.sub.10 alkoxy groups;
- R.sub.2 represents hydrogen and R.sub.3 represents a hydroxy group, or R.sub.2 and R.sub.3 together represent the oxygen atom of a carbonyl group.
Dependencies are inferred from the claim text.