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Methods For The Purification Of Deoxycholic Acid

A technology of bile acid and glycocholic acid, which is applied in the fields of chemical instruments and methods, organic chemistry, pharmaceutical formulations, etc.

Inactive Publication Date: 2012-12-05
KYTHERA BIOPHARMLS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, purification to at least 99% is technically challenging

Method used

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  • Methods For The Purification Of Deoxycholic Acid
  • Methods For The Purification Of Deoxycholic Acid
  • Methods For The Purification Of Deoxycholic Acid

Examples

Experimental program
Comparison scheme
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example

[0549] In the examples below and elsewhere in the specification, the following abbreviations have the indicated meanings. If an abbreviation is not defined, it has the accepted meaning.

[0550] Ac 2 o

Acetic anhydride

ACN

Acetonitrile

AcOH

Acetic acid

CAD

Charged aerosol detector

CONC

strong

CrO 3

Chromium trioxide

DCA

deoxycholic acid

DCM (CH 2 Cl 2 )

Dichloromethane

DMAP

4-Dimethylaminopyridine

DMF

N,N-Dimethylformamide

EtAlCl 2

Ethyl aluminum dichloride

EtOAc

ethyl acetate

H or h

Hour

h 2 SO 4

sulfuric acid

HCl

hydrochloric acid

HClO 4

perchloric acid

HPLC

HPLC

[0551] HPLC-RI

High Pressure Liquid Chromatography with Refractive Index Detection

Hz

Hertz

KBr

potassium bromide

K-O t Bu

Potassium tert-butoxide

L...

example 1

[0556] Synthesis of 3α-Acetoxy-5β-Androstane-9,11-en-17-one from Hydrocortisone (36)

[0557] step 1

[0558]

[0559] To a solution of hydrocortisone (25.0 g) in DMF (150 mL) was added 10% Pd / C (1.5 g, 6-wt%) and the resulting slurry was autoclaved (60 psi) at 25-35 °C Hydrogenated for 6 hours. After the complete disappearance of the starting material was demonstrated by TLC (30% EtOAc in DCM), the The crude reaction mixture was filtered over a (8 g) bed and washed with DMF (100 mL). The solvent was completely removed by vacuum distillation below 65 °C to afford compound 15 (23.0 g, 91.5%) as a white solid.

[0560] step 2

[0561]

[0562] To a solution of compound 15 (23.0 g) in ethanol (350 mL) and DCM (350 mL) was added sodium borohydride (2.4 g), and the resulting solution was stirred at 25-35 °C for 3 hours. At this point, 50% acetone in water (200 mL) was added to quench excess reagent, followed by sodium periodate (33.7 g). The resulting solution was stir...

example 2

[0570] (Z)-3α-Acetoxy-5β-pregna-9(11), 17(20)-diene(30):

[0571]

[0572] Compound 30 can be prepared by converting compound 28 to compound 30 using a procedure similar to that described in Example 8.

[0573] Methods and examples of preparation and purification of DCA from compound 60 are described in GB2452358 and U.S. provisional application 61 / 288,132 entitled "METHODS FOR THE PURIFICATION OF DEOXYCHOLIC ACID" filed on December 18, 2009 , both of which are incorporated herein by reference in their entirety.

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Abstract

Synthetic methods for preparing deoxycholic acid and intermediates thereof, high purity synthetic deoxycholic acid, compositions and methods of use are provided. Also, provided are processes for the synthesis of 12-keto or 12-a-hydroxysteroids from Delta-9,11-ene, 11-keto or 11-hydroxy-ss-steroids. This invention is also directed to novel compounds prepared during the synthesis. This invention is also directed to the synthesis of deoxycholic acid starting from hydrocortisone.

Description

[0001] References to related applications [0002] This application asserts U.S. Provisional Application No. 61 / 288,132, filed December 18, 2009, U.S. Provisional Application No. 61 / 303,816, filed February 12, 2010, UK Application, filed May 25, 2010 1008726.0 and U.S. Provisional Application No. 61 / 348,686, filed May 26, 2010, all of which are hereby incorporated by reference in their entirety. technical field [0003] The present invention is directed to the synthesis of deoxycholic acid and its salts and intermediates suitable for the synthesis of deoxycholic acid. In one embodiment, the present invention provides a synthetic method for preparing deoxycholic acid or a salt thereof using hydrocortisone as a starting material. The invention is also directed to intermediates such as 12-keto or 12-alpha-hydroxy steroids and novel methods for their preparation. The present invention further provides purified deoxycholic acid compositions and methods of purification, wherein t...

Claims

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Application Information

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IPC IPC(8): C07J1/00C07J5/00C07J9/00C07J13/00C07J41/00
CPCC07J41/0061C07J5/0053C07J13/007C07J1/0011C07J9/005C07J9/00C07J21/008A61K31/575A61K2300/00A61P3/04Y02P20/55A61K31/56C07J21/00
Inventor 罗伯特·M·莫里亚蒂约翰·格雷戈里·里德罗伊·A·小斯瓦尔林根
Owner KYTHERA BIOPHARMLS INC
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