New application of thio-taxane derivatives

A technology of taxanes and derivatives, applied in drug combinations, medical preparations containing active ingredients, organic chemistry, etc.

Active Publication Date: 2011-10-19
HAINAN SIMCERE PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report about the antiviral research of taxane compounds.

Method used

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  • New application of thio-taxane derivatives
  • New application of thio-taxane derivatives
  • New application of thio-taxane derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Take a 100mL three-neck flask, burn it to dryness, blow nitrogen, and add BTC (3.82g) at 0°C, then add dry CH 2 Cl 2 (40mL), after the BTC is fully dissolved, add ethyl mercaptan (2.41mL), slowly drop Et 3 N (4.48mL), a white precipitate was formed. After the dropwise addition was completed, the liquid was filtered at room temperature, and the insoluble matter was filtered off from the reaction liquid. The obtained thioacyl chloride solution was directly used in the next reaction without any treatment. Get a 100mL three-necked flask, add paclitaxel intermediate compound 2 (500mg), and use CH 2 Cl 2 (10mL) was dissolved, and the excess acid chloride was slowly added dropwise in an ice-water bath. After the dropwise addition was completed, the liquid was stirred at room temperature to stop the reaction, extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed. Analysis (el...

Embodiment 2

[0037]

[0038] Compound 1g (R is isopropyl), 1 H NMR (300MHz, CDCl 3 ): δ1.11(s, 3H, 17-CH 3 ), 1.14 (d, 3H, J=7.2Hz, 1″-CH 3 ), 1.19 (d, 3H, J=7.2Hz, 3″-CH 3 ), 1.24(s, 3H, 16-CH 3 ), 1.72 (s, 3H, 19-CH 3 ), 1.83(s, 3H, 18-CH 3 ), 2.25 (d, 2H, J=7.5Hz, 14-CH 2 ), 2.35 (s, 3H, OAc), 1.83 and 2.53 (2m, 2H, 6-CH 2 ), 3.49 (m, 1H, 2″-CH), 3.86 (d, 1H, J=6.6Hz, 3-CH), 4.17 and 4.30 (2d, 2H, J=8.7Hz, 20-CH 2 ), 4.21 (m, 1H, 7-CH), 4.45 (s, 1H, 2′-OH), 4.72 (br s, 1H, 2′-CH), 4.93 (d, 1H, J=9.0Hz, 5 -CH), 5.30 (s, 1H, 10-CH), 5.59 (d, 1H, J = 9.0Hz, 3'-CH), 5.65 (d, 1H, J = 6.6Hz, 2-CH), 6.24 ( t, 1H, J=8.7Hz, 13-CH), 6.52(d, 1H, J=8.7Hz, -CONH-), 7.33(m, 1H, p-Ph), 7.39(m, 4H, o-Ph and m-Ph), 7.50(t, 2H, J=7.5Hz, m-OBz), 7.62(t, 1H, J=7.5Hz, p-OBz), 8.11(d, 2H, J=7.5Hz, o -OBz); ESIMS m / z 832.1 [M+Na] + .

[0039] Compound 1h (R is tert-butyl), 1 H NMR (300MHz, CDCl 3 ): δ1.11(s, 3H, 17-CH 3 ), 1.24(s, 3H, 16-CH 3 ), 1.35(s, 9H, t-Bu), 1.71(s, 3H, 19-CH 3 ), 1...

Embodiment 3

[0045] Compound 1m (R is benzyl), 1 H NMR (400MHz, CDCOCD 3 ): δ1.14(s, 3H, 17-CH 3 ), 1.19 (s, 3H, 16-CH 3 ), 1.71 (s, 3H, 19-CH 3 ), 1.86(s, 3H, 18-CH 3 ), 2.20 (m, 2H, 14-CH 2 ), 2.36(s, 3H, OAc), 1.82and 2.44(2m, 2H, 6-CH 2 ), 3.77 (s, 1H, 2′-OH), 3.90 (d, 1H, J=7.0Hz, 3-CH), 4.07 (d, 2H, J=4.0Hz, 1″-CH 2 ), 4.15 (d, 2H, J=5.1Hz, 20-CH 2 ), 4.29 (m, 1H, 7-CH), 4.35 (s, 1H, 10-OH), 4.68 (d, 1H, J=4.8Hz, 2′-CH), 4.94 (d, 1H, J=9.5 Hz, 5-CH), 5.21 (s, 1H, 10-CH), 5.55 (d, 1H, J=6.0Hz, 3'-CH), 5.66 (d, 1H, J=7.0Hz, 2-CH) , 6.18(t, 1H, J=8.8Hz, 13-CH), 7.25(m, 1H, p-Ph), 7.28(t, 1H, J=7.7Hz, p-1″-Ph), 7.39(m , 4H, o-Ph and m-Ph), 7.40 (t, 2H, J=7.2Hz, m-1″-Ph), 7.47 (d, 2H, J=7.3Hz, o-1″-Ph), 7.56(t, 2H, J=7.5Hz, m-OBz), 7.64(t, 1H, J=7.3Hz, p-OBz), 7.90(m, 1H, J=5.2Hz, -CONH-), 8.10( d, 2H, J=7.3Hz, o-OBz); ESIMS m / z 880.3 [M+Na] + .

[0046] Compound 1n (R is p-methylphenyl), ESIMS m / z 880.3[M+Na] + .

[0047] Compound 1o (R is p-methoxyphenyl), ESIMS m / z 896.3...

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Abstract

The invention discloses a new application of thio-taxane derivatives which have the structure shown in formula (1), wherein R is hydrogen, C1-18 are alkyl groups, C1-18 are substituted alkyl groups, C2-10 are alkenyl groups, C2-10 are alkynyl, C3-6 are naphthenic base, C4-6 are cyclenes base, aryl, substituted aryl, heterocyclic groups or substituted heterocyclic groups, and the substituent is one or several types selected from C1-8 alkyl groups, C1-8 alkoxy, C1-8 halogenated alkyl, halogen, aryl, nitryl or amino. The thio-taxane derivative can be used for preparing medicines for treating hepatitis B.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and medicine, and specifically relates to the use of a thiotaxane derivative. Background technique [0002] According to the World Health Organization, there are currently more than 300 million people suffering from hepatitis B worldwide, and 25% of them are facing the threat of liver cirrhosis and liver cancer. my country is a high-incidence area of ​​hepatitis B virus infection, the carrier rate of hepatitis B surface antigen (HBsAg) is 10%, and there are about 30 million chronic hepatitis B patients. The condition of such patients is protracted, and some may develop into liver cirrhosis and liver cancer, which is extremely harmful to human health. Big. Inoculation of hepatitis B vaccine to prevent hepatitis B is the most effective measure, but once the disease occurs, it must be actively treated. [0003] The currently domestically recognized therapy for the treatment of hepatitis ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D305/14A61K31/337A61P31/20A61P1/16
Inventor 孙逊陆洪福章思及昌军谢晨林国强檀爱民
Owner HAINAN SIMCERE PHARMA CO LTD
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