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Enzymatic process for obtaining 17 alpha-monoesters of cortexolone and/or its 9,11-dehydroderivatives

A technology for deoxycortisol and medicine, which is applied in the field of enzymatic method for obtaining 17α-monoester of 11-deoxycortisol and/or 9,11-dehydroderivatives thereof, and can solve the problem that the monoester is unstable and difficult to obtain. Operation and separation issues

Active Publication Date: 2013-12-18
CASSIOPEA SPA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] However, the monoesters thus obtained are unstable under the reaction conditions and thus difficult to handle and isolate (R. Gardi et al. Tetrahedron Letters, 448, 1961)

Method used

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  • Enzymatic process for obtaining 17 alpha-monoesters of cortexolone and/or its 9,11-dehydroderivatives
  • Enzymatic process for obtaining 17 alpha-monoesters of cortexolone and/or its 9,11-dehydroderivatives
  • Enzymatic process for obtaining 17 alpha-monoesters of cortexolone and/or its 9,11-dehydroderivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Alcoholysis of 11-deoxycortisol 17α,21-dipropionate using CCL

[0094]Butanol (0.4 g, 5.45 mmol) and CCL (17.4 g, 3.86 U / mg, FLUKA) were added to 11-deoxycortisol-17α, 21-dipropionate (0.5 g, 1.09 mmol) in toluene ( 50ml) solution. The mixture was kept stirring at 30° C., then reacted in TLC (toluene / ethyl acetate 6 / 4) until the starting material dissolved (24 h). The enzyme was removed by filtration using a Celite bed. 11-Deoxycortisol 17α-propionate (0.437, 99%) was recovered after evaporation at low pressure. The product was obtained with a purity >99% in HPLC by crystallization from diisopropyl ether.

[0095] 1 H-NMR (500MHz, CDCl 3 ) correlation signal δ (ppm) 5.78 (br s, 1H, H-4), 4.32 (dd, 1H, H-21), 4.25 (dd, 1H, H-21), 1.22 (s, 3H, CH 3 -19),1.17(t,3H,CH 3 ),0.72(s,3H,CH 3 -18).P.f.114℃

Embodiment 2

[0097] 11-Deoxycortisol 17α-butyrate was prepared according to the method described in Example 1

[0098] 1 H-NMR correlation signal δ(ppm)5.78(br s,1H,H-4),4.32(dd,1H,H-21),4.26(dd,1H,H-21),1.23(s,3H,CH 3 -19),0.97(t,3H,CH 3 ),0.73(s,3H,CH 3 -18).P.F.134-136℃

Embodiment 3

[0100] 11-Deoxycortisol-17α-valerate was prepared according to the method described in the examples

[0101] 1 H-NMR correlation signal δ(ppm)5.77(br s,1H,H-4),4.32(dd,1H,H-21),4.26(dd,1H,H-21),1.22(s,3H,CH 3 -19),0.95(t,3H,CH 3 ),0.72(s,3H,CH 3 -18). P.f. 114°C (diisopropyl ether).

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Abstract

The present invention refers to a new enzymatic process for obtaining 17a- monoesters of cortexolone and / or its 9,11-dehydroderivatives starting from the corresponding 17alpha,21-diesters which comprises an enzymatic alcoholysis reaction. Furthermore, the present invention refers to new crystalline forms of cortexolone 17alpha-propionate and 9,11-dehydro-cortexolone 17alpha-butanoate.

Description

[0001] The application date is July 24, 2008, the application number is "200880024538.9", and the title of the invention is "Used to obtain 17α-monoester of 11-deoxycortexol and / or its 9,11-dehydro derivatives Divisional application of the application of "enzyme method". field of invention [0002] The present invention relates to an enzymatic process for obtaining 17α-monoesters of 11-deoxycortisol and / or 9,11-dehydroderivatives thereof. Background technique [0003] It is known that derivatives of 11-deoxycortisol and the corresponding 9,11-dehydro derivatives in which the hydroxyl group at the C-17α position is esterified with short-chain fatty acids or aromatics have antiandrogenic effects. [0004] EP1421099 describes about 11-deoxycortisol 17α-propionate and 9,11-dehydro-11-deoxycortisol-17-α which exhibit high anti-androgenic biological activity both "in vitro" and "in vivo" in animals - Butyrate. [0005] Methods for obtaining the above derivatives are described by...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J5/00A61K31/573A61P13/00A61P15/00A61P5/00A61P17/00A61P17/10A61P17/08A61P17/14A61P13/08A61P35/00A61P15/16A61P5/24
CPCC07J5/0053C12P33/00C07B2200/13C12P33/005A61K31/573A61P13/00A61P13/08A61P15/00A61P15/16A61P17/00A61P17/08A61P17/10A61P17/14A61P25/00A61P35/00A61P5/00A61P5/24A61P5/28C07J7/008A61K9/0014A61K47/10A61K47/14A61K9/06A61K47/06A61K47/26A61K47/44
Inventor 毛罗·阿加尼卢吉·摩洛
Owner CASSIOPEA SPA
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