Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1990-03-05
1993-06-08
Bond, Robert T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
540113, 540114, 552505, 552582, 552653, C07J 4300, C07J 5100, C07J 900, C07J 1700
Patent
active
052181090
DESCRIPTION:
BRIEF SUMMARY
FIELD OF ART
This invention relates to novel steroid compounds.
The steroid compounds according to the invention are useful as intermediates for the synthesis of vitamin D.sub.3 derivatives having a hydroxyl group at the 1.alpha.-position, for example 1.alpha., 25-dihydroxyvitamin D.sub.3 known to be useful in the treatment of diseases resulting from disturbances in calcium metabolism, such as chronic renal insufficiency, hypoparathyroidism, osteomalacia and osteoporosis, as well as 1.alpha.-hydroxyvitamin D.sub.3, 1.alpha., 23-dihydroxyvitamin D.sub.3, 1.alpha., 24-dihydroxyvitamin D.sub.3, 1.alpha., 23,25-trihydroxyvitamin D.sub.3, 1.alpha.,24,25-trihydroxyvitamin D.sub.3 and 1.alpha., 25,26-trihydroxyvitamin D.sub.3, which are known to have vitamin D.sub.3 -like activities.
PRIOR ART
The so-far known processes for the production of vitamin D.sub.3 derivatives having a hydroxyl group at the 1.alpha.-position include, among others, the process for producing 1.alpha.-hydroxyvitamin D.sub.3 using cholesterol as the starting material (cf. Japanese Laid-open Patent Application Kokai Nos. 62750/1973 and 95956/1974), the process for producing 1.alpha., 25-dihydroxyvitamin D.sub.3 via an intermediate, cholesta-1,5,7-trien-3-one-25-ol, ##STR2## derived from cholesta-1,4,6-trien-3-one-25-ol (cf. Japanese Laid-open Patent Application Kokai No. 100056/1976), and the process for producing (24R)-1.alpha., 24,25-trihydroxyvitamin D.sub.3 which comprises irradiating (24R)-1.alpha., 3.beta.,24,25-tetrahydroxycholesta-5,7-diene with ultraviolet light in an inert organic solvent and isomerizing the resulting (24R)-1.alpha., 24,25-trihydroxyprevitamin D.sub.3 (cf. Japanese Laid-open Patent Application Kokai 108046/1986). A process is also known for the production of 1.alpha., 25-dihydroxyvitamin D.sub.3 (cf. Japanese Laid-open Patent Application Kokai No. 50152/1978) and this process uses, as an intermediate, such a pregnane derivative as (20S)-1.alpha., 3.beta.-diacetoxypregn-5-ene-20-carbaldehyde of the formula (i) shown below, which is derived from (20S)-21-hydroxy-20-methyl-6.beta.-methoxy-3.alpha.,5-cyclo-5.alpha.-pregn ane, (20S)-21-hydroxy-20-methylpregna-1,4-dien-3-one or the like. The latter process is schematically shown below. ##STR3## In the above formulas, THP means a tetrahydropyran-2-yl group, Ac means an acetyl group, . . . (dotted line) indicates that the substituent is in the .alpha.-configuration, (wedge) indicates that the substituent is in the .beta.-configuration and .about. (swung dash) indicates that the substituent is either in the .alpha.-configuration or in the .beta.-configuration.
Furthermore, a process for producing 1.alpha.,25,26-trihydroxyvitamin D.sub.3 from the above-mentioned (20S)-1.alpha.,3.beta.-diacetoxypregn-5-ene-20-carbaldehyde of formula (i) is known (cf. Japanese Laid-open Patent Application No. 51447/1981).
While, as mentioned above, various processes are known for the production of vitamin D.sub.3 derivatives having a hydroxyl group at the 1.alpha.-position, it would be desirable if many compounds become available as intermediates for the synthesis of such vitamin D.sub.3 derivatives having a hydroxyl group at the 1.alpha.-position and, as a result, an appropriate process can be selected for the production thereof according to materials availability circumstances.
Accordingly, it is an object of the invention to provide various novel steroid compounds which can be converted to vitamin D.sub.3 derivatives having a hydroxyl group at the 1.alpha.-position.
DISCLOSURE OF THE INVENTION
In accordance with the invention, the above object is accomplished by providing:
(1) Pregnane derivatives of the general formula ##STR4## wherein R.sup.1 and R.sup.2 each is a hydrogen atom or a hydroxyl-protecting group and R is a group of the formula --CH.sub.2 --X, a carboxyl group or a protected carboxyl group, X being a hydroxyl group, an acyloxyl group, a lower alkoxycarbonyloxyl group, a trisubstituted silyloxyl group, an alkoxymethoxyl group which may optionally be substituted, a benzylo
REFERENCES:
patent: 4193921 (1980-03-01), Furst et al.
patent: 4260804 (1981-04-01), DeLuca et al.
patent: 4310467 (1982-01-01), Batcho et al.
patent: 4407754 (1983-10-01), Barner et al.
Ikekawa, Medical Research Reviews, 7(3), 333-366 (1987).
Boris et al., Endocrinology of Calcium Metabolism, (Ravens Press, New York, 1982), pp. 297-320.
Nakagawa Naoshi
Takahashi Takashi
Takigawa Tetsuo
Tsuji Jiro
Tsuji Masao
Bond Robert T.
Kuraray Co. Ltd.
Ward E. C.
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