Pregnane derivatives and processes for production thereof

Details Pregnane derivatives and processes for production thereof Pregnane derivatives and processes for production thereof

1990-06-15

1992-05-12

Pal, Asok

Organic compounds -- part of the class 532-570 series

Organic compounds

Cyclopentanohydrophenanthrene ring system containing

552560, 552562, 552580, 552582, 552583, C07J 2100, C07J 900

Patent

active

051129981

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to novel pregnane derivatives and to processes for producing the same.
The pregnane derivatives according to the invention are of value as synthetic intermediates for the production of vitamin D.sub.3 derivatives having a hydroxy group in the 1.alpha.-position, such as 1.alpha.-hydroxy-vitamin D.sub.3, which are known to be effective in the treatment of disorders of calcium metabolism such as chronic renal failure, dysparathyroidism, osteomalacia, osteoporosis and so on.


BACKGROUND ART

The hitherto-known processes for producing vitamin D.sub.3 derivatives having a hydroxy group in the 1.alpha.-position include, for example, the process for producing 1.alpha.-hydroxy-vitamin D.sub.3 using cholesterol as a starting material (Japanese Patent Application Laid-open No. 48-62750 and No. 49-95956), the process for producing 1.alpha., 25-dihydroxy-vitamin D.sub.3 using cholesta-1,5,7-trien-3-on-25-ol derived from cholesta- 1,4,6-trien-3-on-25-ol as a synthetic intermediate (Japanese Patent Application Laid-open No. 51-100056), and the process for producing (24R)-1.alpha.,24,25-trihydroxy-vitamin D.sub.3 by subjecting (24R)-1.alpha.,3.beta.,24,25-tetrahydroxycholesta-5,7-diene to ultraviolet irradiation in an inert organic solvent and, then, isomerizing the resulting (24R)-1.alpha., 24, 25-trihydroxy-previtamin D.sub.3 (Japanese Patent Application Laid-open No. 51-108046). It is also known that certain pregnane derivatives, such as (20S)-1.alpha.,3.beta.-diacetoxypregn-5-ene-20-carbaldehyde, etc., which are 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, etc. by the processes shown below can be converted to 1.alpha.,25-dihydroxy-vitamin D.sub.3 and other compounds (Japanese Patent Application Laid-open No. 53-50152). ##STR2## In the above formulas, THP is a 2-tetrahydropyranyl group; Ac is an acetyl group; the dotted line ( . . . ) indicates that the substituent is in the .alpha.-configuration; the solid line (-) indicates that the substituent is in the .beta.-configuration; the wavy line (.about.) indicates that the substituent is either in the .alpha.-configuration or in the .beta.-configuration.
There is also known a process by which 1.alpha.,25,26-trihydroxy-vitamin D.sub.3 is synthesized from the aforementioned (20S)-1.alpha.,3.beta.-diacetoxypregn-5-ene-20-carbaldehyde (Japanese Patent Application Laid-open No. 56-51447).
While a variety of processes are thus known for the production of vitamin D.sub.3 derivatives having a hydroxy group in the 1.alpha.-position, it is obviously preferable that, in the production of such vitamin D.sub.3 derivatives having a hydroxy group in the 1.alpha.-position, one have as many compounds as possible to choose from as synthetic intermediates, for one would then enjoy the utmost flexibility in selecting the optimum process sequence according to the availability of starting compounds.
It is, therefore, an object of the invention to provide novel compounds which can be converted to various vitamin D.sub.3 derivatives having a hydroxy group in the 1.alpha.-position.
It is another object of the invention to provide processes for producing such novel compounds.


Disclosure of Invention

The aforementioned objects of the present invention are accomplished by providing pregnane derivatives of the following general formula ##STR3## wherein A.sup.1 is in the .alpha.-configuration and represents a hydrogen atom or a hydroxyl group, and A.sup.2 is such that where A.sup.1 is in the .alpha.-configuration and represents a hydrogen atom, A.sup.2 is in the .beta.-configuration and represents a hydroxyl group, an acyloxy group, a lower alkoxycarbonyloxy group, an N-lower alkylcarbamoyloxy group, an N-arylcarbamoyloxy group, an N,N-di(lower alkyl)carbamoyloxy group, a tri-substituted silyloxy group or an alkoxymethoxy group which may optionally be substituted and that where A.sup.1 is in the .alpha.-configuration and represents a hydroxyl group, A.sup.

REFERENCES:
patent: 4193921 (1980-03-01), Furst
patent: 4310467 (1982-01-01), Batcho et al.

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