Steroid compound as well as preparation method and application thereof

A compound and composition technology, applied in the field of medicine, can solve problems such as poor drug absorption

Pending Publication Date: 2022-06-07
GUANGZHOU OCUSUN OPHTHALMIC BIOTECHNOLOGY CO LTD
View PDF0 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Lanosterol is also an endogenous substance in eye tissue, and there is a basal concentration in each tissue. It has been reported that lanosterol is used to treat cataracts, but it was found that local administration of lanosterol to the eye did not increase the concentration of ocular tissue during the experiment. The concentration of lanosterol in various parts especially the lens, which shows that lanosterol is poorly absorbed after topical administration in the eye

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Steroid compound as well as preparation method and application thereof
  • Steroid compound as well as preparation method and application thereof
  • Steroid compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1. Synthesis of compound I-1 (SZY1906-P21)

[0044] Specific steps are as follows:

[0045] 1.1. Synthesis of CDP-Y120-3:

[0046]

[0047] Add CDP-Y120-1 (25g) to a 1000ml round-bottomed flask, add 500ml DMF and stir to form a suspension, add imidazole (9.56g), stir and react for half an hour, add TBSCl (10.6g) in batches, heat to 80°C Dissolved and reacted for 8h. The temperature of the reaction solution was monitored by TLC until the reaction was completed, and the temperature of the reaction solution was lowered to room temperature. The reaction solution was added to 3000ml of water, extracted with DCM 500ml*5, the organic phases were combined and concentrated, washed with 3000ml of water again, extracted with DCM 500ml*5, and the organic phases were combined and concentrated. Repeat the operation one more time. The organic phase was dried with anhydrous sodium sulfate, rotary evaporated, and purified by column chromatography four times using n-hexane ...

Embodiment 2

[0056] Example 2. Synthesis of compound I-2 (SZY1906-P23)

[0057]

[0058] Add CDP-Y120-1 (2.8g) to a 100ml round-bottomed flask, add 80ml DCM to dissolve, add DMAP (160mg) and stir for half an hour, then add EDCI (2.5g), o-methylaminobenzoic acid (1.2g), The reaction was stirred for 12h. The reaction solution was washed with 700 ml of water, extracted with DCM 300*3, dried and rotary evaporated, and purified by column chromatography to obtain about 0.85 g of white solid compound I-2.

[0059] 1 HNMR CDCl 3 δ:7.64-7.70(d,J=8.0Hz,1H),7.32-7.38(t,1H),6.94-6.98(d,J=8.0Hz,1H),6.83-6.88(t,1H),5.11- 5.17(t,1H), 4.70-4.76(q,1H), 3.72-3.79(q,1H), 2.85-2.95(s,3H), 2.00-2.14(q,5H), 1.72-1.90(q,10H) ),1.58-1.66(q,8H),1.27-1.47(q,6H),0.90-1.06(q,16H),0.72(s,3H)

[0060] LC-MS: m / z=574.4 (M+1).

Embodiment 3

[0061] Example 3. Synthesis of compound I-3 (SZY1906-P22)

[0062]

[0063] Add CDP-Y120-1 (2.2g) to a 100ml round bottom flask, add 80ml DCM to dissolve, add DMAP (125mg) and stir for half an hour, then add EDCI (1.98g), o-dimethylaminobenzoic acid (1.02g) , and the reaction was stirred for 12h. The reaction solution was washed with 500 ml of water, extracted with 300 ml of DCM*3, dried and rotary evaporated, and purified by column chromatography to obtain about 1.9 g of white solid compound I-3.

[0064] 1HNMR CDCl 3 δ:7.66-7.72(d,J=8.0Hz,1H),7.33-7.39(t,1H),6.96-7.00(d,J=8.0Hz,1H),6.84-6.89(t,1H),5.10- 5.16(t, 1H), 4.72-4.78(q, 1H), 3.71-3.79(q, 1H), 2.83-2.93(s, 6H), 2.01-2.11(t, 5H), 1.72-1.92(t, 10H) ),1.56-1.64(t,8H),1.25-1.47(t,6H),0.90-1.04(t,16H),0.72(s,3H)

[0065] LC-MS: m / z=588.5 (M+1).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a steroid compound and pharmaceutically acceptable salt thereof, and a preparation method and application thereof. The structural formula of the steroid compound is shown as a formula I ', in the formula I', R is dimethylamino or methylamino, and the eye drops taking the compound (SZY1906-P22) of the formula I with R being dimethylamino as an active ingredient can reduce the lens opacity of New Zealand rabbits with spontaneous senile cataract.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a steroid compound and a preparation method and application thereof. Background technique [0002] Lanosterol, also known as isocholesterol, is a white odorless powder with a variety of important biological activities and a wide range of pharmacological effects, such as anticancer, lowering blood pressure, treating leukemia, lowering blood sugar, and relieving cataracts in experimental animals (experimental rabbits and experimental dogs). illness, etc. Lanosterol is an intermediate in the biosynthesis of sterols, has important physiological functions, and is an important raw material in the cosmetic, pharmaceutical and chemical industries. Lanosterol is also an endogenous substance in eye tissue, with a basal concentration in each tissue. It has been reported that lanosterol is used to treat cataracts, but during the experiment, it was found that local administration of lanos...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00C07J9/00A61K31/575A61P27/12
CPCC07J41/0088C07J41/0055C07J9/00A61P27/12
Inventor 刘国强刘伟其他发明人请求不公开姓名
Owner GUANGZHOU OCUSUN OPHTHALMIC BIOTECHNOLOGY CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap