Prostaglandins

Details Prostaglandins Prostaglandins

C - Chemistry, Metallurgy

07

D

260/235.01

C07D 277/62 (2006.01) C07D 213/55 (2006.01) C07C 177/00 (1985.01)

Patent

CA 1237717

ABSTRACT PROSTAGLANDINS A process for the preparation of a compound of formula (I) Image (I) wherein Image represents one of the divalent cyclic groups Image Image and the letters a and b indicating in each case the points of attachment of the substituents R1 and Image respectively; R1 represents a 6-carboxyhex-2-enyl group or a modification thereof in which the group is altered by one, or where appropriate by a combination of the following: (a) reduction of the double bond optionally accom- panied by replacement of a carbon atom at the 1, 2 or 3 position by a sulphur or oxygen atom, (b) alteration of the position of the double bond, (c) shortening or lengthening of the carbon chain by one or two methylene groups, and (d) formation of an amide, ester or salt derivative of the carboxy group; R2 represents a C1-10 aliphatic hydrocarbon group or a C1-10 aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group Ar, where Ar is a phenyl, naphthyl, fluorenyl, dibenzocyclohexyl, dibenzocycloheptyl, pyridyl, benzothiazolyl, dihydrobenzothiazolyl, N-methyldihydrobenzothiazolyl, benzoxazolyl, dihydrobenzoxazolyl or N-methyldihydrobenzoxazolyl group or such a group substituted by one or more substituents selected from C1-10 alkoxy, halogen, C1-10 halogen substituted alkyl, sulphamoyl, amino, hydroxyl, nitro and C1-10 alkyl groups; and either V represents hydrogen and W represents a hydroxy group or V and W together re- present the oxygen atom of a carbonyl group; comprises reacting a compound of formula (II) Image (II) in which Z represents (a) a formyl group or (b) a group CH(R2)OH, Y is either R1 as defined for (I) or a precursor for R1 and A and R2 are as defined for (I), the said reaction con- sisting of (a) effecting a Grignard reaction involving the formyl group and a reagent R2 MgHalogen to give a group CH(R2)OH or (b) effecting oxidation of the group CH(R2)OH to give a group C(R2)=0, and where appropriate converting the group Y in the resultant product into a group R1. The compounds prepared by this process are of value for the production of biologically active prostag- landin compounds.

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