# US 2023/0057232 A1 · Isotopically labeled bile acid derivatives

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- Number: US 2023/0057232 A1
- Document ID: US20230057232A1
- Status: Published application
- Kind: A1
- Application number: 17/939,326
- Filed: 2022-09-07
- Published: 2023-02-23
- Earliest claimed: 2017-07-24
- Assignees: Intercept Pharmaceuticals, Inc.
- Applicants: Intercept Pharmaceuticals, Inc.
- Inventors: Gabriel GALVIN; Kevin SCHAAB; Matthew YANIK
- Web page: https://patentgrep.com/patent/US20230057232A1

## CPC

- C07J 41/0061: {one of the carbon atoms being part of an amide group}
- C07J 9/005: {containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton}
- C07J 17/005: {Glycosides}
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C07J 9/00: Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J 41/0094: {containing nitrile radicals, including thiocyanide radicals}
- C07J 51/00: Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
- C07J: STEROIDS (seco-steroids C07C)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present application relates to isotopically labeled compounds of Formula I and methods of preparation and use thereof

## Claims

### Claim 1

A compound of Formula I
or a pharmaceutically acceptable salt thereof, wherein
R1 is OH, O-glucuronide, OSO3H, SO3H, CO2R5, 14CO2R5, C(O)R6, 14C(O)R6;
R2 is H, D, or OH;
R3 is OH or O-glucuronide;
R4 is OH or O-glucuronide;
R5 is H or substituted or unsubstituted alkyl;
R6 is NH(CH2)2SO3H, NHCH2CO2H, or N(CH3)CH2CO2H or glucuronic acid moieties,
wherein hydrogens in can be replaced with deuterium;
R11 is Z11b, hydroxy, halogen, alkoxy, or oxo when Z11a is not present;
R16 is Z16a, hydroxy, halogen, alkoxy, or oxo when Z16b is not present;
R23 is Z23a or alkyl; and
Z1a, Z1b, Z2a, Z2b, Z3, Z4a, Z4b, Z5, Z6, Z7, Z8, Z9, Z11a, Z11b, Z12, Z14, Z15a, Z15b, Z16a, Z16b, Z17, Z18, Z19, Z20, Z21, Z22a, Z22b, Z23a, Z23b, Z24a, Z24b, or Z25 is independently selected from H (hydrogen) or D (deuterium), and at least one of Z1a, Z1b, Z2a, Z2b, Z3, Z4a, Z4b, Z5, Z6, Z7, Z8, Z9, Z11a, Z11b, Z12, Z14, Z15a, Z15b, Z16a, Z16b, Z17, Z18, Z19, Z20, Z21, Z22a, Z22b, Z23a, Z23b, Z24a, Z24b, or Z25 is D; and
any carbon atom is 12C, 13C, or 14C.

### Claim 2 (depends on 1)

The compound of claim 1 wherein R2 is H.

### Claim 3 (depends on 1)

The compound of claim 1 wherein R2 is OH.

### Claim 4 (depends on 3)

The compound of claim 3 wherein R2 is alpha-OH.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R6 is taurine (—NH(CH2)2SO3H), glycine (—NHCH2CO2H), or sarcosine (—N(CH3)CH2CO2H).

### Claim 6 (depends on 1)

The compound of claim 1, wherein compound of Formula I is a compound of Formula II

### Claim 7 (depends on 1)

The compound of claim 1, wherein compound of Formula I is a compound of Formula III

### Claim 8 (depends on 1)

The compound of claim 1, wherein compound of Formula I is a compound of Formula IV

### Claim 9 (depends on 1)

The compound of claim 1, wherein compound of Formula I is a compound of Formula V

### Claim 10 (depends on 1)

The compound of claim 1, wherein compound of Formula I is a compound of Formula VI

### Claim 11 (depends on 1)

The compound of claim 1, wherein compound of Formula I is a compound of Formula VII

### Claim 12 (depends on 1)

The compound of claim 1, wherein compound of Formula I is a compound of Formula VIII
wherein R1 is 14CO2R5 or 14C(O)R6.