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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
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  • 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

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  • 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).

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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 specifically relates to a steroid compound and its preparation method and application. Background technique [0002] Lanosterol, also known as isocholesterol, is a white, odorless powder with a variety of important biological activities and extensive pharmacological effects, such as anti-cancer, lowering blood pressure, treating leukemia, lowering blood sugar, and alleviating cataracts in experimental animals (experimental rabbits and experimental dogs) illness, etc. Lanosterol is an intermediate in the biosynthesis of sterols. It has important physiological effects and is an important raw material in the cosmetics, medicine, and chemical industries. Lanosterol is also an endogenous substance in eye tissue and has a basic concentration in each tissue. There are reports of using lanosterol to treat cataracts. However, during the experiment, it was found that local administration of lanosterol to the e...

Claims

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Application Information

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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
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