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.
Claims35
A compound which is a bicyclo[2,2,1]heptane or hept-2Z-ene which is 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 of CONHSO.sub.2 CH.sub.3 ;
- and wherein said bicyclo[2,2,1]heptane or hept-2Z-ene is substituted at the 6-position by a grouping of the formula:
- --C(R).dbd.NO--R';
- wherein
- R is selected from the group consisting of hydrogen, unsubstituted C.sub.1 -C.sub.10 branched or unbranched aliphatic hydrocarbon residues and C.sub.1 -C.sub.10 aliphatic hydrocarbon residues substituted by Ar, --OAr or --SAr, where Ar represents a monocyclic aromatic hydrocarbon or pyridyl residue, or such a residue substituted by one or more substituents selected from the group consisting of halogen, halogen substituted branched or unbranched C.sub.1 -C.sub.5 alkyl groups, sulphonamido groups, amino groups, hydroxy and C.sub.1 -C.sub.10 alkoxy;
- and
- R' is selected from the group consisting of unsubstituted C.sub.1 -C.sub.10 branched or unbranched aliphatic hydrocarbon residues, Ar and C.sub.1 -C.sub.10 branched or unbranched aliphatic hydrocarbon residues substituted by Ar, --OAr, or --SAr.
Dependencies are inferred from the claim text.