IP Library › Granted Patent US 12,419,897
Granted Patent B2
US 12,419,897 · App. 17/309,520 · Granted Sep 23, 2025

Synthetic derivatives of cholic acid 7-sulfate and uses thereof

Inventors: Abigail Sloan Devlin (Cambridge, MA); Snehal N. Chaudhari (Cambridge, MA); Eric Garland Sheu (Brookline, MA); David A. Harris (Arlington, MA); Jinbo Lee (Cambridge, MA)
Assignees: President and Fellows of Harvard College; The Brigham and Women's Hospital, Inc.
A61K31/664A61K31/575A61P3/04A61P3/10
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Quick Facts
Patent No.
US 12,419,897
App. No.
17/309,520
Granted
Sep 23, 2025
Kind
B2
Abstract

The compositions and methods provided herein are related, in part, to the discovery of cholic acid 7-sulfate as a treatment for diabetes. Provided herein is a method for treating a metabolic disorder (e.g., diabetes, obesity), or an inflammatory disease (e.g., Crohn's disease, inflammatory bowel disease, ulcerative colitis, pancreatitis, hepatitis, appendicitis, gastritis, diverticulitis, celiac disease, food intolerance, enteritis, ulcer, gastroesophageal reflux disease (GERD), psoriatic arthritis, psoriasis, and rheumatoid arthritis) in a subject in need thereof comprising administering to a subject a compound of Formulae (I)-(XVII).

Claims (51)

1. A method for treating diabetes, obesity, or an inflammatory disease in a subject, the method comprising administering to a subject in need thereof a compound of Formula (I):

wherein:

n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;

m is 1;

Z is —C(O)—, —C(O)O—, —C(O)NR 18 - or —CH 2 -;

X is H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —OR 18 , —N(R 18 ) 2 , —SR 18 , halogen, CN, —CHO, —CO 2 H, —CO 2 R 18 , —NO 2 , —ONO 2 , —SO 2 Cl, —SO 3 , —OSO 3 , —NR 18 SO 3 , —PO 3 2− , —OPO 3 2− , —OSO 2 R 18 , —OSO 2 N(R 18 ) 2 , —NR 18 SO 2 R 18 , —SO 2 N(R 18 ) 2 , -NHNH 2 , —ONH 2 , -NHC(O)NHNH 2 , or a polar amino acid;

each R 1 , R 2 , R 4 , R 11 , R 15 , R 16 , and R 17 is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —OR 18 , —N(R 18 ) 2 , —SR 18 , halogen, CN, —CHO, —CO 2 H, —CO 2 R 18 , —NO 2 , —ONO 2 , —SO 2 Cl, —SO 3 − , —OSO 3 − , —NR 18 SO 3 , —PO 3 2− , —OPO 3 2− , —OSO 2 R 18 , —OSO 2 N(R 18 ) 2 , —NR 18 SO 2 R 18 , —SO 2 N(R 18 ) 2 , -NHNH 2 , —ONH 2 , or -NHC(O)NHNH 2 ;

each R 3 , R 6 , and R 12 is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —OR 18 , —N(R 18 ) 2 , —SR 18 , halogen, —CN, —CHO, —CO 2 H, —CO 2 R 18 , —NO 2 , —ONO 2 , —SO 2 Cl, —SO 3 , —OSO 3 , —NR 18 SO 3 , —PO 3 2− , —OPO 3 2− , —OSO 2 R 18 , —OSO 2 N(R 18 ) 2 , —NR 18 SO 2 R 18 , —SO 2 N(R 18 ) 2 , -NHNH 2 , —ONH 2 , or -NHC(O)NHNH 2 ;

R 7 is —C(R 18 ) 2 SO 3 H, —C(R 18 ) 2 SO 3 , —SO 2 N(R 18 ) 2 , —OSO 2 N(R 18 ) 2 , —NR 18 SO 3 H, or —NR 18 SO 3 ;

each R 18 is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl;

or a pharmaceutically acceptable salt thereof.

2. The method of claim 1 , wherein R 7 is —C(R 18 ) 2 SO 3 H, —C(R 18 ) 2 SO 3 31 , —NR 18 SO 3 31 , —OSO 2 N(R 18 ) 2 , or —SO 2 N(R 18 ) 2 , —SO 3 31 , —SO 3 H, or —SR 18 .

3. A compound of Formula (I):

wherein:

n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;

m is 1;

Z is —C(O)—, —C(O)O—, —C(O)NR 18 -, or —CH 2 -;

X is H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —OR 18 , —N(R 18 ) 2 , —SR 18 , halogen, —CN, —CHO, —CO 2 H, —CO 2 R 18 , —NO 2 , —ONO 2 , —SO 2 Cl, —SO 3 , —OSO 3 , —NR 18 SO 3 , —PO 3 2− , —OPO 3 2− , —OSO 2 R 18 , —OSO 2 N(R 18 ) 2 , —NR 18 SO 2 R 18 , —SO 2 N(R 18 ) 2 , -NHNH 2 , —ONH 2 , -NHC(O)NHNH 2 , or a polar amino acid;

each R 1 , R 2 , R 4 , R 11 , R 15 , R 16 , and R 17 is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —OR 18 , —N(R 18 ) 2 , —SR 18 , halogen, —CN, —CHO, —CO 2 H, —CO 2 R 18 , —NO 2 , —ONO 2 , —SO 2 Cl, —SO 3 − , —OSO 3 , —NR 18 SO 3 , —PO 3 2− , —OPO 3 2− , —OSO 2 R 18 , —OSO 2 N(R 18 ) 2 , —NR 18 SO 2 R 18 , —SO 2 N(R 18 ) 2 , -NHNH 2 , —ONH 2 , or -NHC(O)NHNH 2 ;

each R 3 , R 6 , and R 12 is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —OR 18 , —N(R 18 ) 2 , —SR 18 , halogen, —CN, —CHO, —CO 2 H, —CO 2 R 18 , —NO 2 , —ONO 2 , —SO 2 CI, —SO 3 , —OSO 3 , —NR 18 SO 3 , —PO 3 2− , —OPO 3 2− , —OSO 2 R 18 , —OSO 2 N(R 18 ) 2 , —NR 18 SO 2 R 18 , —SO 2 N(R 18 ) 2 , -NHNH 2 , —ONH 2 , or -NHC(O)NHNH 2 ;

R 7 is —C(R 18 ) 2 SO 3 H, —C(R 18 ) 2 SO 3 , —SO 2 N(R 18 ) 2 , —OSO 2 N(R 18 ) 2 , —NR 18 SO 3 H, or —NR 18 SO 3 ;

each R 18 is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;

or a pharmaceutically acceptable salt thereof.

4. The compound of claim 3 , wherein the compound is of any one of the Formulae (II)-(XV):

or a pharmaceutically acceptable salt thereof.

5. The compound of claim 3 , wherein R 1 , R 2 , R 4 , R 15 , and R 16 are H.

6. The compound of claim 3 , wherein R 17 is C 1 -C 6 alkyl.

7. The compound of claim 6 , wherein R 17 is unsubstituted methyl.

8. The compound of claim 3 , wherein n is 2.

9. The compound of claim 3 , wherein at least one of R 3 , R 6 , and R 12 is —OSO 3 − , —NR 18 SO 3 − , or —OPO 3 2− .

10. The compound of claim 3 , wherein at least one of R 6 and R 12 is —OSO 3 , —NR 18 SO 3 − , or —OPO 3 2− .

11. The compound of claim 3 , wherein R 6 is —OSO 3 , —NR 18 SO 3 − , or —OPO 3 2− .

12. The compound of claim 11 , wherein R 12 is independently —OSO 3 − .

13. The compound of claim 3 , wherein R 6 is —OSO 3 − ).

14. The compound of claim 3 , wherein R 3 , R 6 , and R 12 are independently H, -OH, —OSO 3 , —NR 18 SO 3 − , or —OPO 3 2− , provided that at least one of R 3 , R 6 , R 7 , and R 12 is —OSO 3 − , —NR 18 SO 3 , or —OPO 3 2− .

15. The compound of claim 3 , wherein the compound is of the formula:

or a pharmaceutically acceptable salt thereof.

16. A pharmaceutically acceptable salt of the compound of claim 15 .

17. The pharmaceutically acceptable salt of claim 16 , wherein the pharmaceutically acceptable salt is an ammonium salt or a sodium salt.

18. A pharmaceutical composition comprising a compound of Formula (I) and a pharmaceutically acceptable carrier or excipient, wherein compound of Formula (I) has the structure:

wherein:

n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;

m is 1;

Z is —C(O)—, —C(O)O—, —C(O)NR 18 -, or —CH 2 -;

X is H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —OR 18 , —N(R 18 ) 2 , —SR 18 , halogen, —CN, —CHO, —CO 2 H, —CO 2 R 18 , —NO 2 , —ONO 2 , —SO 2 CI, —SO 3 , —OSO 3 , —NR 18 SO 3 , —PO 3 2− , —OPO 3 2− , —OSO 2 R 18 , —OSO 2 N(R 18 ) 2 , —NR 18 SO 2 R 18 , —SO 2 N(R 18 ) 2 , -NHNH 2 , —ONH 2 , -NHC(O)NHNH 2 , or a polar amino acid;

each R 1 , R 2 , R 3 , R 4 , R 11 , R 15 , R 16 , and R 17 is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —OR 18 , —N(R 18 ) 2 , —SR 18 , halogen, —CN, —CHO, —CO 2 H, —CO 2 R 18 , —NO 2 , —ONO 2 , —SO 2 CI, —SO 3 − , —OSO 3 − , —NR 18 SO 3 − , —PO 3 2− , —OPO 3 2− , —OSO 2 R 18 , —OSO 2 N(R 18 ) 2 , —NR 18 SO 2 R 18 , —SO 2 N(R 18 ) 2 , -NHNH 2 , —ONH 2 , or -NHC(O)NHNH 2 ,

each R 3 , R 6 , and R 12 is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —OR 18 , —N(R 18 ) 2 , —SR 18 , halogen, —CN, —CHO, —CO 2 H, —CO 2 R 18 , —NO 2 , —ONO 2 , —SO 2 Cl, —SO 3 , —OSO 3 , —NR 18 SO 3 , —PO 3 2− , —OPO 3 2− , —OSO 2 R 18 , —OSO 2 N(R 18 ) 2 , —NR 18 SO 2 R 18 , —SO 2 N(R 18 ) 2 , -NHNH 2 , —ONH 2 , or -NHC(O)NHNH 2 ;

R 7 is —C(R 18 ) 2 SO 3 H, —C(R 18 ) 2 SO 3 , —SO 2 N(R 18 ) 2 , —OSO 2 N(R 18 ) 2 , —NR 18 SO 3 H, or —NR 18 SO 3 ;

each R 18 is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl;

or a pharmaceutically acceptable salt thereof.

19. The compound of claim 18 , wherein R 7 is —C(R 18 ) 2 SO 3 H, —C(R 18 ) 2 SO 3 31 , —OSO 2 N(R 18 ) 2 , or —SO 2 N(R 18 ) 2 .

Assignments (3)
CONFIRMATORY LICENSE Recorded Dec 5, 2023
From: HARVARD UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 065774/0814 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2022
From: DEVLIN, ABIGAIL SLOAN; CHAUDHARI, SNEHAL N.; LEE, JINBO
To: PRESIDENT AND FELLOWS OF HARVARD COLLEGE
Reel/Frame 059646/0187 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2022
From: HARRIS, DAVID A.; SHEU, ERIC GARLAND
To: THE BRIGHAM AND WOMEN'S HOSPITAL, INC.
Reel/Frame 059646/0199 →
Continuity (2)
Provisional Application 62775029 · Dec 4, 2018
Related Publication 20220016138A1 · Jan 20, 2022
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