CN1793160A - Process for synthesizing cholester-5-ylene-3bata-hydroxy-24-one and derivative - Google Patents

Process for synthesizing cholester-5-ylene-3bata-hydroxy-24-one and derivative Download PDF

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CN1793160A
CN1793160A CN 200510121377 CN200510121377A CN1793160A CN 1793160 A CN1793160 A CN 1793160A CN 200510121377 CN200510121377 CN 200510121377 CN 200510121377 A CN200510121377 A CN 200510121377A CN 1793160 A CN1793160 A CN 1793160A
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alkene
courage steroid
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CN100436475C (en
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颜光美
张静夏
丘鹏新
黄亦俊
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Sun Yat Sen University
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Abstract

The invention discloses a compounding method for cholest-5alkene-3beta hydroxy-24-ketone and the ramificatioin. It uses hyodesoxycholic acid as raw material that reacts with protochloride to make 3beta-acetoxy-cholest-5-alkene-24 -acyl chloride, which takes reaction with isopropyl cadion under the radiation of ultrasonic to form 3beta-acetoxy-cholest-5-alkene-24-ketone, and cholest-5-alkene-3beta-hydroxy-24-ketone, which would take reaction with methyl triphenyl bromination phosphine to gain 24-methylene-cholest-5-alkene-3beta- alcohol, would be gained by alkaline degradation; 4-methylene-cholest-5-alkene- 3beta-alcohol would take reaction with hydrazine to form cholest-5alkene-3beta hydroxy-24-ketone. The invention is low cost, and high yield.

Description

The synthetic method of courage steroid-5-alkene-3 beta-hydroxies-24-ketone and derivative
Technical field
The present invention relates to the synthetic method of courage steroid-5-alkene-3 beta-hydroxies-24-ketone and derivative.
Background technology
Steroidal compounds has multiple important physiological function in vivo, as anticancer, and anti-inflammatory; neuroprotective etc.; courage steroid-5-alkene-3 beta-hydroxies-24-ketone is the important intermediate (structure is suc as formula I, hereinafter to be referred as the I compound) of synthetic many steroidal compounds, and people such as Cui Jianguo once were that raw material is through synthetic this compound (the JianGuo Cui of multistep with the Stigmasterol; LongMei Zeng; JingYu Su, et al., Steroids; 2001; 66,33-38), and synthetic thus a series of polyhydroxy ocean steroidal compound (Lu Weigang with multiple pharmacologically active function; the Su Jing joy; once Gansu Province plum, applied chemistry, 2002; 19 (5), 471-473).
Different 17-position side-chain structures often show different pharmacologically actives, obtain a series of derivatives by courage steroid-5-alkene-3 beta-hydroxies-24-ketone is synthetic, are expected to become potential neuroprotective class medicine.
Summary of the invention
The synthetic method that the purpose of this invention is to provide a kind of courage steroid-5-alkene-3 beta-hydroxies-24-ketone and derivative.
Synthetic method of the present invention is that to get oxycholic acid with pig be raw material, prepare 3 β-acetoxyl group-courage steroid-5-alkene-24-acid, by become 3 β-acetoxyl group-courage steroid-5-alkene-24-acyl chlorides with the sulfur oxychloride prepared in reaction, under the ultrasonic wave radiation and the sec.-propyl cadion react 3 β-acetoxyl group-courage steroid-5-alkene-24-ketone, get courage steroid-5-alkene-3 beta-hydroxies-24-ketone by alkaline hydrolysis; Courage steroid-5-alkene-3 beta-hydroxies-24-ketone synthesizes the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-with methyltriphenylphosphonium bromide reaction Synthetic 2 4-methylene radical-courage steroid-5-alkene-3 β-alcohol and hydrazine reaction respectively.Reaction scheme is as shown below:
I. courage steroid-5-alkene-3 beta-hydroxies-24-ketone;
II.3 β-acetoxyl group-courage steroid-5-alkene-24-acid;
III.3 β-acetoxyl group-courage steroid-5-alkene-24-acyl chlorides;
IV.3 β-acetoxyl group-courage steroid-5-alkene-24-ketone;
V.24-methylene radical-courage steroid-5-alkene-3 β-alcohol;
VI. two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-.
The concrete steps of synthetic method of the present invention are:
(1) the II reference literature (Bharucha KR, Buckley GC, Cross CK, et al.Can J Chem., 1955,34:982-990.) synthetic;
(2) II is dissolved in the dry-out benzene, adds sulfur oxychloride, add the pyridine of catalytic amount again, at room temperature stirred 2~4 hours, be evaporated to driedly, add benzene again and continue to concentrate, boil off residual sulfur oxychloride, yellow heavy-gravity liquid III;
(3) take by weighing dry magnesium powder, add anhydrous diethyl ether, drip different N-PROPYLE BROMIDE/anhydrous ether solution, add back ultrasonic wave radiation 15~30 minutes, after the ice bath cooling, equimolar Cadmium chloride fine powder is added in batches, under 25~40 ℃, the ultrasonic wave radiation, stir, frozen water cooling slowly is added drop-wise to 30~40% dry-out benzene solution of product III of last step in the reaction system, drips off the back and continues ultrasonic backflow 1~2 hour, after the ice bath cooling, drip 1: 1 aqueous hydrochloric acid, with the benzene extraction, the benzene layer is washed till neutrality with distilled water, dry, concentrating under reduced pressure, silica gel column chromatography gets white solid IV;
(4) will go up the step product IV and be dissolved in the methyl alcohol, add strong base solution, reflux 15~30 minutes, it is neutral transferring pH, methyl alcohol is removed in underpressure distillation, ethyl acetate extraction, organic layer drying, pressure reducing and steaming solvent, get light yellow solid, silica gel column chromatography gets white solid I;
(5) methyltriphenylphosphonium bromide is added in the anhydrous tetrahydrofuran solution, inject n-Butyl Lithium, its injection rate just is dissolved as suitable with methyltriphenylphosphonium bromide, stirring reaction is 4~6 hours under the room temperature, I in the last step is added reaction system, continue reaction 2~3 hours, reaction solution is poured into rapidly in the saturated ammonium chloride solution, use extracted with diethyl ether, ether layer drying, the pressure reducing and steaming solvent gets light yellow solid, silica gel column chromatography gets white solid V;
(6) I is added be dissolved in the ethanol, add the aqueous solution reflux 2~4 hours of hydrazine, the pressure reducing and steaming solvent adds entry, and it be neutral transferring pH, ethyl acetate extraction, white solid, silica gel column chromatography gets white solid VI.
In the above-mentioned reactions steps, the concentration of the benzole soln of II is 25~45% in the step (2), and the amount of sulfur oxychloride is 1.0~2.0 times of mole number of II; The amount of magnesium powder is 1.2~3.0 times of mole number of II in the step (3); Strong base solution in the step (4) is the methanol solution of potassium hydroxide or sodium methylate, and concentration is 3~6%; The concentration of the ethanolic soln of I is 5~10% in the step (6), and the concentration of aqueous solution of hydrazine is 50%~80%.
Synthetic method of the present invention has that raw material is cheap and easy to get, synthetic route is scientific and reasonable, respectively go on foot characteristics such as synthetic yield height.Synthetic product courage steroid-5-alkene-3 beta-hydroxies-24-ketone is the important intermediate of synthetic many steroidal compounds, and steroidal compounds has multiple important physiological function in vivo, as anticancer, and anti-inflammatory, neuroprotective etc.; By the synthetic series derivates that obtains of courage steroid-5-alkene-3 beta-hydroxies-24-ketone such as 24-methylene radical-courage steroid-5-alkene-3 β-alcohol, courage steroid-5-alkene-3 beta-hydroxies-24-pair hydrazones, be expected to become potential neuroprotective class medicine.
Embodiment
Following examples are in order to explanation the present invention, but protection scope of the present invention is not only for following examples.Unless otherwise specified, in following examples: I represents courage steroid-5-alkene-3 beta-hydroxies-24-ketone; II represents 3 β-acetoxyl group-courage steroid-5-alkene-24-acid; III represents 3 β-acetoxyl group-courage steroid-5-alkene-24-acyl chlorides; IV represents 3 β-acetoxyl group-courage steroid-5-alkene-24-ketone; V represents 24-methylene radical-courage steroid-5-alkene-3 β-alcohol; VI represents the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-.
Embodiment 1
Synthesizing of courage steroid-5-alkene-3 beta-hydroxies-24-ketone
(1) get compound (II) 100 gram, add 300ml benzene, the 20ml sulfur oxychloride, the 1ml pyridine at room temperature stirred 2 hours, was evaporated to driedly, removed residual sulfur oxychloride, compound (III), with the dissolving of 200ml benzene, standby.
(2) get 37 gram exsiccant magnesium powder, add the 120ml anhydrous diethyl ether, the anhydrous ether solution of the different N-PROPYLE BROMIDE of instillation 140ml adds to keep and refluxed 30 minutes, and cooling adds 137 gram Cadmium chloride fine powdeies in four batches, refluxes 30 minutes down at 40 ℃.The ice bath cooling slowly drips the benzene mixed solution that compound (III) is made into down, drips the ultrasonic backflow of Bi Jixu 2 hours.After water-cooled on the rocks is frozen 30 minutes, drip 1: 1 aqueous hydrochloric acid of 150ml, with benzene extraction three times, the benzene layer is washed till neutrality with distilled water, anhydrous sodium sulfate drying, and concentrating under reduced pressure, silica gel column chromatography gets white solid (IV).
(3) will go up the potassium hydroxide methanol solution that step product (IV) 10g is added to 500mL3%, reflux 30 minutes, pH with 5% hydrochloride adjusted solution is neutral, methyl alcohol is removed in underpressure distillation, ethyl acetate extraction three times, organic layer merge uses anhydrous sodium sulfate drying, pressure reducing and steaming solvent, get light yellow solid, the white solid of silica gel column chromatography (I).
Embodiment 2
Synthesizing of courage steroid-5-alkene-3 beta-hydroxies-24-ketone
(1) get compound (II) 100 gram, add 400ml benzene, the 32ml sulfur oxychloride, the 1ml pyridine at room temperature stirred 4 hours, was evaporated to driedly, removed residual sulfur oxychloride, compound (III), with the dissolving of 200ml benzene, standby.
(2) step (2) with embodiment 1 is identical.
(3) step (3) with embodiment 1 is identical.
Embodiment 3
Synthesizing of courage steroid-5-alkene-3 beta-hydroxies-24-ketone
(1) step (1) with embodiment 1 is identical.
(2) get 20 gram exsiccant magnesium powder, add the 60ml anhydrous diethyl ether, the anhydrous ether solution of the different N-PROPYLE BROMIDE of instillation 73ml under 60% ultrasonic wave radiation adds and continued ultrasonic 15~30 minutes, add 78 gram Cadmium chloride fine powdeies after the cooling in four batches, under 25~40 ℃, opened for 60% ultra-sonic oscillation half an hour.The frozen water cooling slowly drips the benzene mixed solution of compound (III) down, drips the ultrasonic backflow of Bi Jixu 2 hours.After water-cooled on the rocks is frozen 30 minutes, drip 150ml (1: 1) aqueous hydrochloric acid, with benzene extraction three times, the benzene layer is washed till neutrality with distilled water, anhydrous sodium sulfate drying, and concentrating under reduced pressure, silica gel column chromatography gets white solid (IV).
(3) step (3) with embodiment 1 is identical.
Embodiment 4
Synthesizing of courage steroid-5-alkene-3 beta-hydroxies-24-ketone
(1) step (1) with embodiment 1 is identical;
(2) step (2) with embodiment 3 is identical;
(3) will go up the methanol solution that step product (IV) 10g is added to the sodium methylate of 300mL3%, stirring at room 1 hour, pH with 5% hydrochloride adjusted solution is neutral, methyl alcohol is removed in underpressure distillation, ethyl acetate extraction three times, organic layer merge uses anhydrous sodium sulfate drying, pressure reducing and steaming solvent, get light yellow solid, the white solid of silica gel column chromatography (I).
Embodiment 5
Synthesizing of 24-methylene radical-courage steroid-5-alkene-3 β-alcohol
(1) identical with step (1)~(3) of embodiment 4.
(2) in the 25mL anhydrous tetrahydrofuran solution, add 1.2 gram methyltriphenylphosphonium bromides, logical nitrogen injects an amount of n-Butyl Lithium, and stirring reaction is 4~6 hours under the room temperature, the tetrahydrofuran solution that to go up (I) in the step injects reaction system, continue reaction 23 hours, reaction solution is poured into rapidly in the saturated ammonium chloride solution, use extracted with diethyl ether, ether layer anhydrous sodium sulfate drying, the pressure reducing and steaming solvent gets light yellow solid, the white solid of silica gel column chromatography (V).
Embodiment 6
Synthesizing of 24-methylene radical-courage steroid-5-alkene-3 β-alcohol
(1) identical with step (1)~(3) of embodiment 4.
(2) in the 50mL anhydrous tetrahydrofuran solution, add 5 gram methyltriphenylphosphonium bromides, logical nitrogen injects an amount of n-Butyl Lithium, and stirring reaction is 4 hours under the room temperature, the tetrahydrofuran solution of 1 gram (I) is injected reaction system, continue reaction 2 hours, reaction solution is poured into rapidly in the saturated ammonium chloride solution, use extracted with diethyl ether, ether layer anhydrous sodium sulfate drying, the pressure reducing and steaming solvent gets light yellow solid, the white solid of silica gel column chromatography (V).
Embodiment 7
Synthesizing of 24-methylene radical-courage steroid-5-alkene-3 β-alcohol
(1) identical with step (1)~(3) of embodiment 4.
(2) in the 50mL anhydrous tetrahydrofuran solution, add 2 gram methyltriphenylphosphonium bromides, logical nitrogen injects an amount of n-Butyl Lithium, and stirring reaction is 6 hours under the room temperature, the tetrahydrofuran solution of 1 gram (I) is injected reaction system, continue reaction 4 hours, reaction solution is poured into rapidly in the saturated ammonium chloride solution, use extracted with diethyl ether, ether layer anhydrous sodium sulfate drying, the pressure reducing and steaming solvent gets light yellow solid, the white solid of silica gel column chromatography (V).
Embodiment 8
Synthesizing of the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-
(1) identical with step (1)~(3) of embodiment 4.
(2) 1g is used the 10mL dissolve with ethanol, add the aqueous solution of 5mL50% hydrazine, reflux 4 hours, the pressure reducing and steaming solvent adds suitable quantity of water, and it is neutral transferring pH, and ethyl acetate extraction gets white solid, the white solid of silica gel column chromatography (VI).
Embodiment 9
Synthesizing of the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-
(1) identical with step (1)~(3) of embodiment 4.
(2) 1g (I) is used the 20mL dissolve with ethanol, add the aqueous solution of 5mL80% hydrazine, reflux 2 hours, the pressure reducing and steaming solvent adds suitable quantity of water, and it is neutral transferring pH, and ethyl acetate extraction gets white solid, the white solid of silica gel column chromatography (VI).
Purpose product 1: the structural identification of courage steroid-5-alkene-3 beta-hydroxies-24-ketone
Fusing point: 135-137 ℃
Ultimate analysis: C:80.94, H:11.07, calculated value: C 27H 44O 2: C:81.00,11.00, O:8.00.
MS:[M +]=401,[M +-1]=401,
IR(cm -1):3409,2936,2870,1710,1466,1378,1056
1HNMR(CDCl 3):
5.37(1H,t,6β-CH),3.54(1H,m,3-CH),2.60(1H,m,25-CH),1.13(3H,d,26-CH 3,27-CH 3),1.01(3H,s,19-CH 3),0.91(3H,d,21-CH 3),0.68(3H,s,18-CH 3).
13CNMR(CDCl 3):
215.4(C),140.7(C),121.6(CH),71.7(CH),56.7(CH),56.0(CH),50.1(CH),42.3(C),42.2(CH 2),40.8(C),39.7(CH 2),37.2(CH),36.4(CH 2),35.7(CH),31.9(CH),31.6(CH 2),30.9(CH 2),29.8(CH 2),29.6(CH 2),28.2(CH 2),24.2(CH 2),21.0(CH 3),19.3(CH 2),18.7(CH 3),18.5(CH 3),18.3(CH 3),11.8(CH 3).
The structural identification of purpose product 2:24-methylene radical-courage steroid-5-alkene-3 β-alcohol
Fusing point: 148-149 ℃
Ultimate analysis: C:83.36, H:11.80, calculated value: C 28H 46O:C:84.42, H:11.56;
MS:[M +-1]=398,[M ++1]=399,[M ++1]=400
IR(cm -1):3416,3028,2936,2868,1642,1464,1377,1057.
1HNMR(CDCl 3):
5.38(1H,t,6β-H),0.71(1H,d,28-CH),.65(1H,d,28-CH),3.52(1H,m,3-CH),2.25(1H,m,25-CH),1.13(6H,d,26-CH 3,27-CH 3),1.01(3H,s,19-CH 3),0.91(3H,d,21-CH 3),0.69(3H,s,18-CH 3).
13CNMR(CDCl 3):
156.8(C),140.7(C),121.6(CH),105.9(CH 2),71.8(CH),56.8(CH),56.0(CH),50.1(CH),42.35(C),42.30(CH 2),39.8(C),37.2(CH),36.5(CH),35.7(CH),34.7(CH),33.8(CH 2),31.9(CH 2),31.6(CH 2),30.9(CH 2),28.2(CH 2),24.2(CH 2),22.0(CH 3),21.8(CH 2),21.1(CH 3),19.4(CH 3),18.7(CH 3),11.8(CH 3).
Purpose product 3: the structural identification of the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-
Ultimate analysis: C:81.52, H:11.53, N:3.36;
Calculated value: C 54H 88O 2N 2C:81.34, H:11.13, N:3.51.
MS:[M] +=897,[M+1] +=898,
IR:3382,2933,2867,2859,1637,1466,1377,1058.
1HNMR(CDCl 3):
5.35(1H,t,6β-H),3.52(1H,m,3-CH),2.62(1H,m,25-CH),1.16(6H,d,26-CH 3,27-CH 3),1.01(3H,s,19-CH 3),0.91(3H,d,21-CH 3),0.69(3H,s,18-CH 3).
13CNMR(DMSO):
169.1(C),142.1(C),121.0(CH),70.9(CH),57.1(CH),56.2(CH),50.6(CH),43.0(C),42.8(CH 2),42.4(C),37.9(CH),37.6(CH),36.9(CH),36.2(CH),35.9(CH 2),32.4(CH 2),32.2(CH 2),29.8(CH 2),29.6(CH 2),28.7(CH 2),24.7(CH 2),21.5(CH 3),21.0(CH 2),20.9(CH 3),19.9(CH 3),19.1(CH 3),12.4(CH 3).

Claims (6)

1. the synthetic method of courage steroid-5-alkene-3 beta-hydroxies-24-ketone and derivative, it is characterized in that with the Hyodeoxycholic Acid being raw material, prepare 3 β-acetoxyl group-courage steroid-5-alkene-24-acid, by become 3 β-acetoxyl group-courage steroid-5-alkene-24-acyl chlorides with the sulfur oxychloride prepared in reaction, under the ultrasonic wave radiation and the sec.-propyl cadion react 3 β-acetoxyl group-courage steroid-5-alkene-24-ketone, get courage steroid-5-alkene-3 beta-hydroxies-24-ketone by alkaline hydrolysis; Courage steroid-5-alkene-3 beta-hydroxies-24-ketone synthesizes the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-with methyltriphenylphosphonium bromide reaction Synthetic 2 4-methylene radical-courage steroid-5-alkene-3 β-alcohol and hydrazine reaction respectively.
2. synthetic method according to claim 1 is characterized in that concrete reactions steps is:
(1) II is dissolved in the dry-out benzene, adds sulfur oxychloride, add the pyridine of catalytic amount again, at room temperature stirred 2~4 hours, be evaporated to driedly, add benzene again and continue to concentrate, boil off residual sulfur oxychloride, yellow heavy-gravity liquid III;
(2) take by weighing dry magnesium powder, add anhydrous diethyl ether, drip different N-PROPYLE BROMIDE/anhydrous ether solution, add back ultrasonic wave radiation 15~30 minutes, after the ice bath cooling, equimolar Cadmium chloride fine powder is added in batches, under 25~40 ℃, the ultrasonic wave radiation, stir, frozen water cooling slowly is added drop-wise to 30~40% dry-out benzene solution of product III of last step in the reaction system, drips off the back and continues ultrasonic backflow 1~2 hour, after the ice bath cooling, drip 1: 1 aqueous hydrochloric acid, with the benzene extraction, the benzene layer is washed till neutrality with distilled water, dry, concentrating under reduced pressure, silica gel column chromatography gets white solid IV;
(3) will go up the step product IV and be dissolved in the methyl alcohol, add strong base solution, reflux 15~30 minutes, it is neutral transferring pH, methyl alcohol is removed in underpressure distillation, ethyl acetate extraction, organic layer drying, pressure reducing and steaming solvent, get light yellow solid, silica gel column chromatography gets white solid I;
(4) methyltriphenylphosphonium bromide is added in the anhydrous tetrahydrofuran solution, inject n-Butyl Lithium, its injection rate just is dissolved as suitable with methyltriphenylphosphonium bromide, stirring reaction is 4~6 hours under the room temperature, I in the last step is added reaction system, continue reaction 2~3 hours, reaction solution is poured into rapidly in the saturated ammonium chloride solution, use extracted with diethyl ether, ether layer drying, the pressure reducing and steaming solvent gets light yellow solid, silica gel column chromatography gets white solid V;
(5) I is added be dissolved in the ethanol, add the aqueous solution reflux 2~4 hours of hydrazine, the pressure reducing and steaming solvent adds entry, and it be neutral transferring pH, ethyl acetate extraction, white solid, silica gel column chromatography gets white solid VI;
In the above-mentioned steps, I represents courage steroid-5-alkene-3 beta-hydroxies-24-ketone; II represents 3 β-acetoxyl group-courage steroid-5-alkene-24-acid; III represents 3 β-acetoxyl group-courage steroid-5-alkene-24-acyl chlorides; IV represents 3 β-acetoxyl group-courage steroid-5-alkene-24-ketone; V represents 24-methylene radical-courage steroid-5-alkene-3 β-alcohol; VI represents the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-.
3. synthetic method according to claim 2 is characterized in that the concentration of the benzole soln of II in the step (1) is 25~45%, and the amount of sulfur oxychloride is 1.0~2.0 times of mole number of II.
4. synthetic method according to claim 2, the amount of magnesium powder in the step (2) of it is characterized in that are 1.2~3.0 times of mole number of II.
5. synthetic method according to claim 2 is characterized in that the strong base solution in the step (3) is the methanol solution of potassium hydroxide or sodium methylate, and concentration is 3~6%.
6. synthetic method according to claim 2 is characterized in that the concentration of the ethanolic soln of I in the step (5) is 5~10%, and the concentration of aqueous solution of hydrazine is 50%~80%.
CNB2005101213773A 2005-12-31 2005-12-31 Process for synthesizing cholester-5-ylene-3bata-hydroxy-24-one and derivative Expired - Fee Related CN100436475C (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007006549A3 (en) * 2005-07-11 2007-03-29 Plt Patent & Licence Trading L Oligomers of cholesterol, cholesterol sulfate and cholesterol esters, and medicaments containing the same

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5573700A (en) * 1978-11-30 1980-06-03 Teijin Ltd Preparation of steroidal ketone compound
CN1448399A (en) * 2003-04-24 2003-10-15 中山大学 Synthetic method of 24-methylene-cholesterol-5-alkenyl-3 beta, 19-glycol
CN1583782A (en) * 2004-05-28 2005-02-23 中山大学 Synthesis of 24-submethyl-cholesterol-5-ene-3 beta, 7 beta, 19-trialcohol
CN1583781A (en) * 2004-05-28 2005-02-23 中山大学 Synthesis of 3 beta, 7 beta, 19-tricarboxy-5-ene-cholestane

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007006549A3 (en) * 2005-07-11 2007-03-29 Plt Patent & Licence Trading L Oligomers of cholesterol, cholesterol sulfate and cholesterol esters, and medicaments containing the same
US8318961B2 (en) 2005-07-11 2012-11-27 PLT Patent & Licensing Trading Ltd. Oligomers of cholesterol, cholesterol sulphate and cholesterol esters and also drugs containing these

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