21-nor-vitamin D compounds

Details 21-nor-vitamin D compounds 21-nor-vitamin D compounds

1996-11-18

1998-12-08

Clardy, S. Mark

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

Organic compounds

Cyclopentanohydrophenanthrene ring system containing

552546, 552552, 552554, 552555, C07J 900

Patent

active

058471731

ABSTRACT:
21-norvitamin D.sub.3 analogs in which the methyl group normally attached to the side chain at carbon 20 has been replaced by a hydrogen atom. The compounds are characterized by a marked intestinal calcium transport activity while exhibiting much lower activity than 1.alpha.,25-dihydroxyvitamin D.sub.3 in their ability to mobilize calcium from bone. Because of their preferential calemic activity, these compounds would be useful for the treatment of diseases where bone formation is desired, such as osteodystrophy. Novel intermediates formed during the synthesis of the end products are also disclosed.

REFERENCES:
patent: 4568491 (1986-02-01), rst et al.
patent: 4711881 (1987-12-01), Ikekawa
Calverley, "Vitamin D" in Antitumour Steroids, (1992) pp. 193-270.
Pumar et al, "Estudios en la sintesis de metabolitos de la vitamin D y analogos. Sintesis de triacetato de 1.alpha.,3.beta.,25-trihidroxi-21-nor-colesta-5,7-dieno", Anales De Quimica, Serie C, vol. 84, No. 1, pp. 105-111, 1988.
Kubodera et al, "Synthetic studies of vitamin D analogues. X. Synthesis and biological activities of 1.alpha.,25-dihydroxy-21-norvitamin D.sub.3 ", Chemical and Parmaceutical Bulletin, vol. 40, No. 3, pp. 648-651, 1992.
Lam et al, "Structural analogs of 1.alpha.,25-dihydroxycholecalciferol: preparation and biological assay of 1.alpha.-hydroxypregnacalciferol", Steroids, vol. 26, No. 4, pp. 422-436, 1975.

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