Organic compounds -- part of the class 532-570 series – Organic compounds – 9,10-seco-cyclopentanohydrophenanthrene ring system or...
Patent
1997-10-08
1999-03-16
Dees, Jose' G.
Organic compounds -- part of the class 532-570 series
Organic compounds
9,10-seco-cyclopentanohydrophenanthrene ring system or...
514167, C07C40100
Patent
active
058832718
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP6/00091 filed Jan. 22, 1996.
TECHNICAL FIELD
The present invention relates to vitamin D.sub.3 derivatives having a substituent at the 2-position. More specifically, the invention relates to compounds represented by general formula (I): ##STR2## wherein R.sub.1 and R.sub.2, which may be the same or different, each represents an alkyl group having 1 to 4 carbon atoms and R.sub.3 represents an alkoxy group having 1 to 7 carbon atoms which may be substituted by one or more substituents selected from a hydroxyl group, a halogen atom, a cyano group, an alkoxy group having 1 to 4 carbon atoms, an amino group and an acylamino group with the proviso that R.sub.1 and R.sub.2 are not a methyl group simultaneously.
BACKGROUND OF THE INVENTION
It has been known that an activated vitamin D.sub.3 has many pharmaceutical activities such as differentiation-inducing and immunoregulating actions in addition to calcium metabolic regulatory action. Up to the present time, vitamin D.sub.3 derivatives having a substituent at the 2-position have been disclosed in, for example, JP 6-23185 B and JP 6-41059 A. Among these compounds are those which are useful as a treating agent for osteoporosis.
DISCLOSURE OF THE INVENTION
In recent years, the pharmaceutical activities of vitamin D compounds have been gradually revealed. For example, 1.alpha., 25-dihydroxy vitamin D.sub.3 is known to exhibit a variety of pharmaceutical activities such as calcium metabolic regulatory action, antiproliferation and differentiation-inducing actions on cells such as tumor cells, and immunoregulatory action. Recently, numerous vitamin D derivatives have been synthesized in an attempt to separate an action from other actions exhibited by the derivatives and their pharmaceutical activities have been reviewed.
As a result of their extensive research, the present inventors have found that the compounds represented by the following general formula (I) are useful as a pharmaceutical: ##STR3## wherein R.sub.1 and R.sub.2, which may be the same or different, each represents an alkyl group having 1 to 4 carbon atoms and R.sub.3 represents an alkoxy group having 1 to 7 carbon atoms which may be substituted by one or more substituents selected from a hydroxyl group, a halogen atom, a cyano group, an alkoxy group having 1 to 4 carbon atoms, an amino group and an acylamino group with the proviso that R.sub.1 and R.sub.2 are not a methyl group simultaneously.
Thus, the present invention relates to compounds represented by general formula (I): ##STR4## wherein R.sub.1 and R.sub.2, which may be the same or different, each represents an alkyl group having 1 to 4 carbon atoms and R.sub.3 represents an alkoxy group having 1 to 7 carbon atoms which may be substituted by one or more substituents selected from a hydroxyl group, a halogen atom, a cyano group, an alkoxy group having 1 to 4 carbon atoms, an amino group and an acylanimo group with the proviso that R.sub.1 and R.sub.2 are not a methyl group simultaneously.
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 is a set of graphs which illustrate the change in the amount of bone mineral density with dose of the compound according to the present invention.
BEST MODE FOR CARRYING OUT THE INVENTION
Among the compounds represented by general formula (I), preferred are those in which R.sub.3 is an alkoxy group having 1 to 7 carbon atoms which may be substituted by one or more hydroxyl groups.
More preferred are those in which R.sub.3 is an alkoxy group having 1 to 7 carbon atoms which is substituted by one or more hydroxyl groups.
Another preferred group of the compounds represented by general formula (I) includes those represented by general formula (II): ##STR5## wherein R.sub.1 and R.sub.2, which may be the same or different, each represents an alkyl group having 1 to 4 carbon atoms and R.sub.3 represents an alkoxy group having 1 to 7 carbon atoms which may be substituted by one or more substituents selected from a hydroxyl group, a halogen atom, a cyano group, an alkoxy group havin
REFERENCES:
patent: 4666634 (1987-05-01), Miyamoto et al.
Okano et al., Biological activity and conformational analysis, Proc. Workshop Vitam. D, 9th Vitamin D, 81-2, 1994.
Nobuo Ikekawa, "Structures and Biological Activities of Vitamin D Metabolites and Their Analogs", Medicinal Research Reviews, vol. 7, No. 3, pp. 333-366, 1987.
Gary H. Posner et al., "Stereocontrolled Total Synthesis of Calcitriol Derivatives: 1,25-Dihydroxy-2-(4'-Hydroxybutyl) Vitamin D.sub.3 Analogs of an Osteoporosis Drug", J. Org. Chem., vol. 59, pp. 7855-7861, 1994.
Chugai Seiyaku Kabushiki Kaisha
Dees Jos,e G.
Pryor Alton
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