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-2-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by a grouping --C(R).dbd.N--NHCO--(NH).sub.a --R' in which R is hydrogen, an aliphatic hydrocarbon residue, an aromatic residue or an aliphatic hydrocarbon residue substituted by an aromatic residue, a is 0 or 1 and R' is 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. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.
Claims32
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 --, wherein 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 COOH, 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)heptane or hept-2Z-ene is substituted at the 6-position by a grouping of the formula:
- --C(R).dbd.NNHCO--(NH).sub.a --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, 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;
- a is 0 or 1;
- 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.
5-endo-(6'-Carboxyhex-2'Z-enyl)-6-exo-(N-(phenylcarbamoyl)-hydrazonomet hyl)-bicyclo(2,2,1)heptane.
5-endo-(6'-Carboxyhex-2 'Z-enyl)-6-exo-(N-diphenylacetylhydrazonomethyl)-bicyclo(2,2,1)heptane.
Dependencies are inferred from the claim text.