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(20s)-1alpha-hydroxy-2-methylene-19-nor-bishomopregnacalciferol and its uses

A methylene, calciferol technology, applied in organic chemistry, digestive system, medical preparations containing active ingredients, etc., can solve problems such as the inability to meet the purity standards of therapeutic drugs, achieve low cost, increase moisture, and improve barrier function Effect

Inactive Publication Date: 2007-04-04
WISCONSIN ALUMNI RES FOUND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, even chromatographically purified 1α-hydroxyvitamin D compounds, although they show consistent spectroscopic data indicating their homogeneity, do not qualify for oral, parenteral, or transdermal therapeutic use. Drug Purity Standards

Method used

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  • (20s)-1alpha-hydroxy-2-methylene-19-nor-bishomopregnacalciferol and its uses
  • (20s)-1alpha-hydroxy-2-methylene-19-nor-bishomopregnacalciferol and its uses
  • (20s)-1alpha-hydroxy-2-methylene-19-nor-bishomopregnacalciferol and its uses

Examples

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Effect test

Embodiment 1

[0088] recrystallized from acetone

[0089] (a) Dissolve the desired purified 2-MbisP product in boiling acetone (1.2ml, Aldrich) under an argon atmosphere, place it at room temperature (68°F) for several hours (1-3 hours), and then place it in the refrigerator (35~45) overnight (8~12 hours). The precipitated crystals were filtered, washed with a small amount of cold (0°C) acetone, and dried.

[0090] (b) The 2-MbisP crystals were then recrystallized from acetone (0.5 ml) as described in step 1(a). The precipitated crystals have a relatively accurate melting point (relatively narrow melting range): 162-164°C.

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Abstract

Disclosed herein is (20S)-1alpha-hydroxy-2-methylene-19-nor-bishomopregnacalciferol, pharmaceutical uses of this compound, and a method of purifying this compound to obtain it in crystalline form. This compound exhibits pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also has little, if any, calcemic activity and therefore may be used to treat immune disorders in humans as well as renal osteodystrophy.

Description

technical field [0001] The present invention relates to vitamin D compounds, more specifically (20S)-1α-hydroxyl-2-methylene-19-nor-bishomopregnacalciferol (bishomopregnacalciferol) and its pharmaceutical application. Background technique [0002] Known natural hormone 1α, 25-dihydroxyvitamin D 3 and its analogs of the ergosterol series, such as 1α, 25-dihydroxyvitamin D 2 is a regulator of calcium homeostasis in humans and animals, and its role in cell differentiation has also been established (see Ostem et al., Proc. Natl. Acad Sci. USA, 84, 2610 (1987)). Many structural analogs of these metabolites have been prepared and tested, including 1α-hydroxyvitamin D 3 , 1α-Hydroxyvitamin D 2 , various side chain homologated vitamins and their fluorinated analogues. Some of these compounds exhibit interesting differences in cell differentiation and calcium regulation. This difference in activity can be used in the treatment of many diseases such as renal osteodystrophy, vitam...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C401/00A61K31/59A61P11/06A61P17/06A61P35/00A61P29/00A61P37/00A61K31/593A61P1/00A61P3/10A61P17/00A61P19/02A61P19/08A61P25/00A61P35/02A61P37/02
CPCC07C401/00A61P1/00A61P11/00A61P11/06A61P17/00A61P17/06A61P19/02A61P19/08A61P25/00A61P29/00A61P35/00A61P35/02A61P37/00A61P37/02A61P3/10A61K31/59
Inventor 赫克托·F.·德卢卡洛里·A.·普拉姆玛格丽特·克拉格特-达梅詹姆斯·B.·托登黑兹尔·M.·霍尔登苏米斯拉·高卢加里帕维尔·格日瓦奇
Owner WISCONSIN ALUMNI RES FOUND
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