IP Library Granted Patent US 10,202,414
Granted Patent B2
US 10,202,414 · App. 15/681,609 · Granted Feb 12, 2019

Process for preparing bile acid derivatives

Inventors: Roberto Pellicciari (Perugia, IT); Antimo Gioello (Perugia, IT)
Assignee: Intercept Pharmaceuticals, Inc.
C07J31/006C07J9/00C07J9/005
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Quick Facts
Patent No.
US 10,202,414
App. No.
15/681,609
Granted
Feb 12, 2019
Kind
B2
Abstract

The present invention relates to processes for preparing compounds of formula I or a pharmaceutically acceptable salt or solvate thereof, wherein the dashed bond (----) at position 7 indicates that the substituent is in an α or β stereochemistry; R is hydrogen or hydroxy; and R 1 is hydrogen or C 1 -C 6 alkyl

Claims (16)

1. A process for preparing a compound of formula I:

or a pharmaceutically acceptable salt or solvate thereof, wherein

the dashed bond (----) at position 7 indicates that the substituent is in an α or β stereochemistry;

R is hydrogen or hydroxy; and

R 1 is hydrogen or C1-C6 alkyl,

comprising the step of

Step 4: converting a compound of formula V to a compound of formula VI:

wherein Step 4 comprises reacting a compound of formula V with RuCl 3 , NaIO 4 , and an acid to form a compound of formula VI.

2. The process of claim 1 , wherein R 1 is ethyl.

3. The process of claim 1 , wherein the compound is selected from

4. The process of claim 1 , further comprising the step of Step 6: converting a compound of formula VII to a compound of formula I-Na comprising reacting a compound of formula VII with a sulfonating agent to form a salt of formula I-Na:

5. The process of claim 4 , further comprising the step of Step 5: converting a compound of formula VI to a compound of formula VII comprising reacting a compound of formula VI with a reducing agent to form a compound of formula VII

6. The process of claim 5 , further comprising the steps of Step 1: esterification of a compound of formula II to a compound of formula III

Step 2: a Grignard reaction to form a compound of formula IV from a compound of formula III:

and

Step 3: protection of a compound of formula IV to a compound of formula V:

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Jan 4, 2024
From: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION
To: INTERCEPT PHARMACEUTICALS, INC.
Reel/Frame 066662/0210 →
CHANGE OF ADDRESS Recorded Jun 30, 2022
From: INTERCEPT PHARMACEUTICALS, INC.
To: INTERCEPT PHARMACEUTICALS, INC.
Reel/Frame 060555/0890 →
SECURITY INTEREST Recorded Aug 18, 2021
From: INTERCEPT PHARMACEUTICALS, INC.
To: U.S. BANK NATIONAL ASSOCIATION
Reel/Frame 057650/0772 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 4, 2018
From: PELLICCIARI, ROBERTO; GIOIELLO, ANTIMO
To: INTERCEPT PHARMACEUTICALS, INC
Reel/Frame 047666/0138 →
Continuity (2)
Division 14438323
Related Publication 20180079776A1 · Mar 22, 2018