Ethynodiol

EthynodlolDia.ceta.te, Ethynodiol diacetate has been used alone, and in combination with an strogen, as an oral contraceptive and to treat disorders associated with progesterone deficiency (76). It may be crystallised from aqueous methanol (77) and is soluble in chloroform, ether, and ethanol sparingly soluble in fixed oils and insoluble in water (76). Extensive spectral and chromatographic data have been compiled (78). 

Ethynodiol diacetate (53) is prepared by reduction of the 3-oxo group of norethindrone (28) with lithium tributoxyalurninum hydride, followed by acylation with acetic anhydride-pyridine (78,79). It has been reported that higher yields can be obtained in the reduction step by using triethylanainoalurninum hydride (80). 

In further modifications of these norprogestins, reaction of norethindrone with acetic anhydride in the presence of p-toluene-sulfonic acid, followed by hydrolysis of the first-formed enol acetate, affords norethindrone acetate (41). This in turn affords, on reaction with excess cyclopentanol in the presence of phosphorus pentoxide, the 3-cyclopentyl enol ether (42) the progestational component of Riglovic . Reduction of norethindrone affords the 3,17-diol. The 33-hydroxy compound is the desired product since reactions at 3 do not show nearly the stereoselectivity of those at 17 by virtue of the relative lack of stereo-directing proximate substituents, the formation of the desired isomer is engendered by use of a bulky reducing agent, lithium aluminum-tri-t-butoxide. Acetylation of the 33,173-diol iffords ethynodiol diacetate, one of the most potent oral proves tins (44). ... 

MonophasicOral Contraceptives 50 meg ethinyl estradiol acetate img norethindrone 50 meg ethinyl estradiol, 1 mg ethynodiol diacetate 50 meg ethinyl estradiol, 0.5 mg norgestrel 35 mg ethinyl estradiol, 1 mg norethindrone 35 meg ethinyl estradiol, 0.5 mg norethindrone 35 meg ethinyl estradiol, 0.4 mg norethindrone 35 meg ethinyl estradiol, 0.25 mg norgestimate 35 meg ethinyl estradiol, 1 mg ethynodiol diacetate... 

Desogen (Organon) Estrostep (Parke Davis) Ethynodiol Diacetate and Ethinyl Estradiol (Watson) Levlen (Berlex)... 

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