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Water-soluble pregnenolone derivative and use thereof

A technology of pregnenolone and derivatives, which is applied in the field of water-soluble pregnenolone derivatives and their uses, and can solve problems such as potential safety hazards

Inactive Publication Date: 2018-09-11
JIANGSU NHWALUOKANG PHARMA RES & DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cyclodextrin is a polymer compound, which has a certain risk of nephrotoxicity (1. Safety research on cyclodextrin derivatives of medicinal supramolecular materials. China Materials Science and Technology and Equipment. Issue 5, 2009, pages 1-3;), Therefore, there is a security risk

Method used

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  • Water-soluble pregnenolone derivative and use thereof
  • Water-soluble pregnenolone derivative and use thereof
  • Water-soluble pregnenolone derivative and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] W is the preparation of the formula I compound of W-1

[0077] Dissolve N-tert-butoxycarbonyl-glycine (10mmol), allopregnenolone (5mmol), and DCC (15mmol) in dry dichloromethane (100ml), add DMAP (5%), react at room temperature for 24h, filter, The organic layer was washed successively with saturated aqueous ammonium chloride solution (40ml*3), saturated sodium bicarbonate (30ml*3) and saturated brine (40ml), the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and the residue was subjected to column chromatography Separation gives N-tert-butoxycarbonyl-glycine-pregnenolone ester.

[0078] Dissolve N-tert-butoxycarbonyl-glycine-pregnenolone ester in ethyl acetate, pass through dry HCl gas, react for 16 hours, concentrate, and crystallize the residue with ethanol and methyl tert-butyl ether to obtain W It is the compound of formula I of W-1.

Embodiment 2

[0080] W is the preparation of the formula I compound of W-5

[0081] With allopregnenolone and N-tert-butoxycarbonyl-valine as raw materials, according to the operation of Example 1, the compound of formula I with W as W-5 can be obtained.

[0082] Using different protecting groups for different amino acids, according to the operation of Example 1, the compound of formula I in which W is W-(1-25) can be prepared.

Embodiment 3

[0084] W is the preparation of the formula I compound of W-27

[0085] Suspend 4-N,N-dimethylaminobutyric acid hydrochloride (10mmol) in dry DCM (40ml), add oxalyl chloride (100mmol) and a drop of DMF, stir overnight at room temperature, evaporate the solvent and excess Oxalyl chloride, the residue was dissolved in dry DCM (30ml) and set aside.

[0086] Dissolve allopregnenolone (5mmol) and DMAP (11mmol) in dry DCM (50ml), cool in an ice bath, slowly add the acid chloride prepared in the step above, after the addition, react at room temperature, detect by HPLC, and react After that, the organic layer was washed successively with saturated ammonium chloride (30ml*3) and saturated brine (30ml), the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and the residue was crystallized with ethanol and ether to obtain W as W-27 The compound of formula I.

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PUM

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Abstract

The invention relates to the technical field of biomedicines, and provides a water-soluble pregnenolone derivatives (represented by formula 1). In the formula 1, L is a bond or a linking moiety, and Wis a water-soluble group. The water-soluble pregnenolone derivative has stable chemical properties and a good water solubility, and rapidly decomposes and releases viable pregnenolone in plasma or invivo to generate pharmacological action.

Description

technical background: [0001] Neurosteroids (Neurosteroids) play an important physiological role in the human body, and its synthesis is impaired, which can lead to different neurological (CN 104736158) or mental diseases ( Expert Opin The Targets. 2014;18(6):679-90). Neurosteroid Allopregnanolone is an agonist of GABA (ν-aminobutyric acid) receptors in the human body, which can combine with GABA to exert physiological effects ( J Physiol .2001;537(Pt 2):453–465). Aiming at the characteristics of allopregnenolone, scientists have conducted a lot of research on it, such as: treatment of Alzheimer's disease (1.Alzheimer'sAssocIntConf (AAIC), 2013, Abst P4-012; 2.12th IntConf Alzheimer Parkinson Dis( AD / PD), 2015, Abst 155), Epilepsy (1.Epilepsia 2013,54:81; 2.68th Annu Meet Am AcadNeurol(AAN), 2016, Abst P4.210; 3.68th Annu Meet Am AcadNeurol(AAN), 2016, Abst S14.003.), postpartum depression (DailyDrugNews.com, June11, 2015) and other nerve-related diseases. [0002] Patent ...

Claims

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Application Information

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IPC IPC(8): C07J7/00C07J43/00C07J17/00C07J41/00A61K31/58A61K31/57A61K31/765A61P25/08A61P25/24A61P25/28A61P25/20C08G65/331C08G65/332
CPCC07J7/002A61P25/08A61P25/20A61P25/24A61P25/28C07J17/00C07J41/005C07J43/003C08G65/331C08G65/3322
Inventor 李勤耕王涛邓金根申义
Owner JIANGSU NHWALUOKANG PHARMA RES & DEV CO LTD
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