C - Chemistry – Metallurgy – 07 – J
Patent
C - Chemistry, Metallurgy
07
J
260/32, 260/9
C07J 21/00 (2006.01) C07J 71/00 (2006.01)
Patent
CA 1062246
ABSTRACT OF THE DISCLOSURE The present invention relates to a novel process for the prepar- ation of 11.beta.-hydroxy-18-alkyl-estrane compounds by reacting an 11.beta.-hydroxy- 13-methyl-gonane compound with an excess of an acylhypoiodite to give an es- trano-18, 11.beta.-lactone, reacting the latter compound with a Grignard compound or an alkyl lithiun compound, possibly after hydrolysis of the lactone, and reducing the thus-obtained 11.beta.-hydroxy-18-alkyl-18-ketone to the corresponding 11.beta.-hydroxy-18-alkyl-estrane compound, and to novel intermediates of the sub- ject compounds. More particularly, this invention relates to a process for the preparation of a steriod of the estrane series of the formula: Image (IIIa) wherein R1 represents an oxygen atom, a ketalised oxygen atom, H2 or (OR3), R2 represents an oxygen atom, a ketalised oxygen atom, (OR4) or (.alpha.-alkyl) (.beta.-OR4), wherein the alkyl group has 1 to 4 carbon atoms and R3 and R4 are the same or different and represent hydrogen atoms or alkyl or acyl groups, the dotted lines represent an optional double bond in the 4,5 or 5,6-position, R5 represents a free, esterified or etherified hydroxyl group, Q is a group Image wherein R6 is alkyl of 1 to 4 carbon atoms or R5 and Q together form an epoxy group of the formula Image wherein R1 is an alkylidene group correspond- ing to R6; which comprises reacting an 18,11.beta.-ketone of the formula: Image (II) or the corresponding 11.beta.-hydroxy-13-carboxylic acid, wherein R1 and R2 and the dotted lines have the same significance as given above, with a lower alkyl or- ganometallic derivative; and when a compound of formula IIIa is required in which R5 and Q together form a group of the formula Image as defined above dehydrating the 11.beta.-hydroxy-18-ketone of formula IIIa so ob- tained. It also relates to the novel products of this process. These novel intermediates are converted into corresponding pharmacologically active 11.beta.- hydroxy-18-alkyl steriods of the estrane series conforming to the general formula: Image (VI) wherein R represents a lower alkyl group; R1 represents H2, H(OR3), an oxygen atom or a ketalised oxygen atom; R2 represents an oxygen atom, a ketalised oxygen atom, H(OR4) or (.alpha.-alkyl) (.beta.-OR4), wherein the alkyl group has 1 to 4 carbon atoms and R3 and R4 are the same or different and represent hydrogen atoms or alkyl or acyl groups; and the dotted lines represent an optional double bond in the 4,5 or 5,6-position; which comprises either:- (a) reducing a corresponding 11.beta.-hydroxy-18-alkyl-18-ketone of the formula: Image (III) wherein R, R1, R2 and the dotted lines have the same significance as in for- mula (VI) above; or (b) reducing a corresponding 11.beta.,18-epoxy-18-alkylidene compound of the formula: Image (VII) wherein R1 is a lower alkylidene group corresponding to R and R1, R2 and the dotted lines have the same significance as in formula (VI) above.
314612
de Jongh Hendrik P.
Van Bokhoven Cornelis W.
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