Process for the preparation of new prostaglandin analogues

Details Process for the preparation of new prostaglandin analogues Process for the preparation of new prostaglandin analogues

C - Chemistry, Metallurgy

08

B

260/235.03

C08B 37/16 (2006.01) C07C 391/02 (2006.01) C07C 405/00 (2006.01) C07F 1/02 (2006.01)

Patent

CA 1098125

ABSTRACT Process for the preparation of prostaglandin analogues of the formula: Image VI (wherein R3 represents the 1,1-dimethylpentyl or 2(.epsilon.)- ethylheptyl group) which comprises reacting a compound of the formula: VII Image (wherein R4 represents a 2-tetrahydropyranyl group unsubstituted or substituted by at least one alkyl radical, or a 2-tetra- hydrofuranyl or 1-ethoxyethyl group, R5 represents an alkyl group of 1 to 4 carbon atoms, and R6 represents an alkylcarbonyl group of 2 to 5 carbon atoms) with the sodio derivative of a dialkyl phosphonate of the formula: Image VIII (wherein R7 represents an alkyl group of 1 to 4 carbon atoms, and R3 is as hereinbefore defined) to obtain a compound of the formula: Image IX . reducing the 15-oxo group in the resulting compound to a hydroxy group, reacting the obtained hydroxy compound with dihydropyran unsubstituted or substituted with at least one alkyl radical, dihydrofuran or ethyl vinyl ether, to obtain a compound of the formula: Image XI . hydrolysing under alkaline conditions the resulting compound to obtain a compound of the formula: Image XII (wherein R represents a hydrogen atom or the methyl radical), converting the 9.alpha.-hydroxy group in the compound of formula XII to an oxo group, and hydrolysing the OR4 groups in the resulting compound of the formula: Image XIII to hydroxy groups to obtain a PGE compound of formula VI or methyl ester thereof. All the double bonds in the foregoing formulae are trans, and the wavy line ? indicates attachment of the group in alpha or beta configuration. The prostaglandin analogues of formula VI possess pharmacological properties.

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