5-beta-sapogenin and pseudosapogenin derivatives and their use in the treatment of dementia

A technology of aglycone and derivatives, applied in the field of 5-beta saponin and pseudosaponin derivatives and their use in the preparation of drugs for treating dementia, can solve basic key defects, Lack of synaptic transmission, no supply, etc.

Inactive Publication Date: 2009-04-22
PHYTOPHARM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages in the above three traditional methods of treating AD / SDAT are: Ach precursor supplementation, stimulant replacement and inhibition of acetylcholinesterase
However, this disclosure is of uncertain value because it is well recognized that there is no infectious factor for a very large number of symptoms characterized by a lack of synaptic transmission, so the fundamental key to the so-called invention is flawed
In addition, they do not provide any data that would enable those skilled in the art to select a preferred compound from the large number of compounds they claim

Method used

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  • 5-beta-sapogenin and pseudosapogenin derivatives and their use in the treatment of dementia
  • 5-beta-sapogenin and pseudosapogenin derivatives and their use in the treatment of dementia
  • 5-beta-sapogenin and pseudosapogenin derivatives and their use in the treatment of dementia

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0151] In CHO cell lines expressing recombinant human muscarinic receptors in vitro, the number of muscarinic receptors tended to decrease over time. Muscarinic receptor density was increased after 72 hours of incubation with saponin derivatives (1-10 μm) according to the invention.

[0152] method:

[0153] Effect of saponin derivatives of the present invention on muscarinic receptor density in CHO cells expressing recombinant human muscarinic receptors.

[0154] Chinese hamster ovary (CHO) cells expressing high levels of receptor (-2.2 pmole receptor / mg protein) were cultured in flasks (150 ml) for 24 hours before starting the experiment. Vehicle (DMSO) and saponin derivatives (1 and 10 [mu]M) were added to the medium for 48 hours. The culture medium was removed, the cells were scraped and resuspended in Hanks solution, centrifuged, and passed through with [ 3 [H]-QNB were incubated for 30 minutes, after which the level of m receptor was determined by liquid scintillation...

Embodiment 2

[0158]

[0159] 3-O-2Oxycarbonyl-5β, 20α, 22α, 25R-spirostan-3β-ol

[0160] Ethyl chloroformate (1.40g, 12.9mmol) was added dropwise to a solution of smilagenin (2.08g, 5.0mmol) in anhydrous dichloromethane (15ml) and anhydrous pyridine (1.02g, 12.9mmol). in the stirred solution. The mixture was stirred at room temperature for 18 hours, then partitioned between water (30 mL) and dichloromethane. The aqueous layer was extracted twice with dichloromethane, and the combined organic layers were washed with water, then dried over magnesium sulfate (anhydrous). The solvent was evaporated in vacuo to give an oil which crystallized rapidly (2.1 g). This material was chromatographed on silica gel (about 70 g), eluting with ethyl acetate-hexane (1:9), and recrystallized from methanol to give 3-O-2oxycarbonyl-5β,20α,22α,25R-spiro White crystals of stan-3β-ol (1.08 g).

[0161] mp154-156℃; m / z 488 (M + for C 30 h 48 o 5 ); 1 H nmr (270MHz, CDCl 3 )δ 0.76 (3H, s, 18-CH 3 ), 0...

Embodiment 3

[0163] Epismilagen succinate

[0164]

[0165] A solution of epismilagenin (200 mg, 0.48 mmol) and succinic anhydride (60 mg, 0.59 mmol) in anhydrous pyridine was stirred overnight at room temperature under nitrogen. Another portion of succinic anhydride (120 mg, 1.18 mmol) was added and the reaction mixture was stirred for an additional 24 hours. After adding another portion of succinic anhydride (120 mg, 1.18 mmol), the reaction mixture was heated at 50° C. for a further 24 hours with stirring. After the reaction was cooled, water (10 mL) was added. The aqueous solution was extracted with ether (4 x 20 mL). The combined organic extracts were washed with water (3 x 20 mL). Dry (anhydrous magnesium sulfate), filter. The solvent was evaporated in vacuo to give an orange oil (1.8 g), which was chromatographed on silica gel using ethyl acetate / petroleum ether (1:4) as eluent. Recrystallization from acetone gave white crystals of epismilagenyl succinate (87 mg).

[0166] ...

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PUM

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Abstract

The invention discloses the use of sapogenin derivatives in the treatment of cognitive disfunction and similar conditions. In addition, methods of treatment and pharmaceutical compositions are also disclosed.

Description

[0001] This application is a divisional application of the following patent application: the application number is 00813606.8, the application date is September 29, 2000, and the invention name is "5-β saponin and pseudosapogenin derivatives and their derivatives in Use in the preparation of medicaments for the treatment of dementia". technical field [0002] The present invention relates to saponin derivatives and their use in the treatment of cognitive impairment and similar conditions, and to compositions for such treatment. The invention also relates to the treatment of conditions characterized by deficits in the number and function of membrane-bound receptors. In the following, the invention will be described primarily with reference to the treatment of Alzheimer's disease (AD) and Alzheimer's-type senile dementia (SDAT), in which defects of many receptor types are shown. However, it should be understood that the present invention generally relates to the treatment of sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/58A61P25/28A61P25/16A61P25/00C07J71/00A61P9/02A61P21/04A61P25/14A61P43/00
CPCC07J71/00C07J71/0005A61P21/04A61P25/00A61P25/14A61P25/16A61P25/28A61P43/00A61P9/02
Inventor P·巴勒克拉夫J·汉森P·冈宁D·里斯夏宗勤胡雅儿
Owner PHYTOPHARM LTD
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