Vitamin D analogues

Details Vitamin D analogues Vitamin D analogues

1993-08-30

1995-03-28

Richter, Johann

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

9,10-seco- cyclopentanohydrophenanthrene ring system doai

552653, C07C40100

Patent

active

054017319

ABSTRACT:
##STR1## The present invention relates to compounds of formula (I), in which formula, n is 0 or 1, m is 0 or an integer from 1-7, R.sup.1 and R.sup.2 (which may be the same or different) stand for hydrogen or C.sub.1 l-C.sub.8 -hydrocarbyl, or, taken together with the carbon bearing the hydroxyl group (starred in formula I), R.sup.1 and R.sup.2 can form a saturated or unsaturated C.sub.3 -C.sub.8 carbocyclic ring. In addition, R.sup.1 and/or R.sup.2 and/or one of the m carbons designated by the ".degree." may be optionally substituted with a hydroxyl group or one or more chlorine or fluorine atom(s); and finally one of the carbons designated ".degree." may optionally be substituted by one or two C.sub.1 -C.sub.2 alkyl group(s); and derivatives of the compounds of formula I in which one or more hydroxy have been transformed into --O-acyl or --O-glycosyl or phosphate ester groups; such masked groups being hydrolyzable in vivo. The present compounds find use in both the human and veterinary practice in the treatment and prophylaxis of autoimmune diseases (including diabetes mellitus), hypertension, ache, alopecia, skin ageing, imbalance in the imune system, inflammatory diseases such as rheumatoid arthritis and asthma as well as diseases characterized by abnormal cell differentiation and/or cell proliferation, such as e.g. psoriasis and cancer.

REFERENCES:
patent: 4069321 (1978-01-01), Jones et al.
patent: 4188345 (1980-02-01), DeLuca et al.
patent: 4195027 (1980-03-01), DeLuca et al.
WO A1 8404527, Nov. 22, 1984, p. 26, Claim 22.
Andrews et al, J. Org. Chem., 51:4819-4828, 1986.
Kutner et al, J. Org. Chem., 53:3450-3457, 1988.
J. Org. Chem. vol. 51, 1986 D. R. Andrews et al: "Synthesis of 25-Hydroxy-and 1, 25-Dihydroxyvitamin D3 from Vitamin D2 (Calciferol)", see p. 4819-p. 4828, 1986.
J. Org. Chem., vol. 53, 1988 A. Kutner et al.: "Novel Convergent Synthesis of Side-Chain-Modified Analogues of 1, 25-Dihydroxycholecalciferol and 1,25-Dihydroxyergocalciferol", see p. 3450-p. 3457, 1988.

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