Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1992-08-06
1993-12-21
Cintins, Marianne M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
549350, A61K 31335, C07D32112
Patent
active
052721728
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to iridoid derivatives having anti-hyperlipemia and cholagogue actions and pharmacologically useful
BACKGROUND ART
The progress of the "aging society", has led to an increase in the number of patients suffering from hyperlipemia, as a geriatric diseases, and the development of an anti-hyperlipemia drug having a greater efficacy and safety is desired Conventional efforts to develop such anti-hyperlipemia drugs have been concentrated on absorption inhibitors and synthetic inhibitors of cholesterol
Cape Jasmim (jasminoides Ellis) is a crude drug from a Chinese recipe and has long been known to have pharmacological effects such as an anti-arteriosclerosis agent, blood coagulation inhibitor and cholagogue, and geniposide as a typical active component of Cape Jasmim has been confirmed to have excellent pharmacological activities.
In the field of anti-hyperlipemia, however, medicaments that have been developed conventionally cannot provide an entirely sufficient therapeutic effect. Therefore, the development of an anti-hyperlipemia having a different mechanism from the conventional medicaments is desired.
In the field of the cholagogue, on the other hand, genipin as the aglycon of geniposide is known as the cholagogue, and the development of iridoid derivatives having an excellent cholagogue action using this geniposide as the starting material is desired
DISCLOSURE OF THE INVENTION
As a result of intensive studies into the problems described above, the inventors of the present invention found that the iridoid derivatives sythesized using genipin as the aglycon of geniposide, which is the principal component of Cape Jasmim, as the starting material have both anti-hyperlipemia and cholagogue actions, and thus completed the present invention.
The present invention provides novel compounds expressed by the following formulas 1 to 14, and their pharmacologically permissible salts. The present invention also provides an anti-hyperlipemia drug and a cholagogue containing the compounds expressed by the following formulas 1 to 18, and their pharmacologically permissible salts, as an active principle. ##STR1##
In the formula, R.sub.1 is a benzoyloxyl group, a hydroxyl group, an acetoxyl group or an ethoxyethoxyl group, and R.sub.2 is a benzoyloxymethyl group, a methoxymethyl group, a tert-butyl-dimethylsilyloxymethyl group, a carboxyl group or a hydroxymethyl group, with the proviso that those compounds of R.sub.1 which represent a hydroxyl group and those of R.sub.2 which represent a hydroxymethyl group are excluded ##STR2##
In the formula, R.sub.1 is a methyl group or a trimethyl-acetyloxymethyl group. ##STR3##
In the formula, R.sub.1 is an .alpha.- or .beta.-oriented methyl group. ##STR4##
In the formula, R.sub.1 is a methyl group or a methoxycarbonyl group, and R.sub.2 is a hydroxyl group or an ethoxyethoxyl group, with the proviso that those compounds is which R.sub.1 represents a methyl group and R.sub.2 represents a hydroxyl group are excluded. ##STR5##
In the formula, R.sub.1 is a hydroxymethyl group, a methyl group or a hydrogen atom, R.sub.2 is a hydroxyl group or an acetoxyl group, and R.sub.3 is an .alpha.- or .beta.-oriented methyl group, with the proviso that those compounds in which R.sub.1 represents a hydrogen atom and R.sub.2 represents a hydroxyl group, and those compounds in which R.sub.1 represents a methyl group and R.sub.2 represents a hydroxyl group are excluded. ##STR6##
In the formula, R.sub.1 is a hydroxyl group or an acetoxyl group. ##STR7##
In the formula, R.sub.1 is a methoxycarbonyl group, a methyl group, a hydroxymethyl group or an acetoxymethyl group, and R.sub.2 is an .alpha.- or .beta.-oriented methyl group. ##STR8##
In the formula, R.sub.1 is a methoxycarbonyl group or a hydroxymethyl group. ##STR9##
In the formula, R.sub.1 is a methoxycarbonyl group or a methyl group, and R.sub.2 is an .alpha.- or .beta.-oriented methyl group. ##STR10##
In the formula, R.sub.1 is a hydrogen atom or a glucopyranosyl group.
BEST MODE OF CARRYING OUT THE INV
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Arai Ichiro
Fujii Yuuichi
Hatta Akira
Kigawa Masaharu
Mitsuhashi Hiroshi
Cintins Marianne M.
Peabody John
Tsumura & Co.
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