IP Library Granted Patent US 8,404,732
Granted Patent B2
US 8,404,732 · App. 13/343,073 · Granted Mar 26, 2013

Methods of treating ulcerative colitis

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Quick Facts
Patent No.
US 8,404,732
App. No.
13/343,073
Granted
Mar 26, 2013
Kind
B2
Abstract

Methods of treating and managing ulcerative colitis, using imidazole-based compounds that inhibit S1P lyase, are disclosed.

Claims (28)

1. A method of treating or managing ulcerative colitis, which comprises administering to a patient in need thereof a therapeutically effective amount of a compound of the formula:

wherein:

R 1 is hydrogen, alkyl or aryl;

R 3 is OR 3A , NHC(O)R 3A , NHSO 2 R 3A or hydrogen;

each R 3A is independently hydrogen or alkyl, aryl, alkylaryl, arylalkyl, heteroalkyl, heterocycle, alkylheterocycle, or heterocyclealkyl optionally substituted with halo;

R 6 is OR 6A or OC(O)R 6A ;

R 7 is OR 7A or OC(O)R 7A ;

R 8 is OR 8A or OC(O)R 8A ;

R 9 is hydrogen, CH 2 OR 9A or CH 2 OC(O)R 9A ; and

each of R 6A , R 7A , R 8A and R 9A is independently hydrogen or lower alkyl.

2. The method of claim 1 , wherein the compound is of the formula:

3. The method of claim 1 , wherein the compound is of the formula:

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

5. The method of claim 3 , wherein R 1 is lower alkyl.

6. The method of claim 3 , wherein R 3 is OR 3A .

7. The method of claim 3 , wherein R 3 is N(R 3A ) 2 or NHC(O)R 3A .

8. The method of claim 3 , wherein R 3 is NHSO 2 R 3A .

9. The method of claim 8 , wherein R 3A is hydrogen or lower alkyl.

10. A method of treating or managing ulcerative colitis, which comprises administering to a patient in need thereof a therapeutically effective amount of a compound of the formula:

or a pharmaceutically acceptable salt thereof, wherein:

R 1 is lower alkyl;

R 3 is hydrogen, OR 3A , NHC(O)R 3A or NHSO 2 R 3A ;

R 9 is hydrogen or CH 2 OH; and

each R 3A is independently hydrogen or lower alkyl.

11. The method of claim 10 , wherein the compound is of the formula:

12. The method of claim 11 , wherein R 3 is OR 3A .

13. The method of claim 12 , wherein R 3A is hydrogen.

14. A method of treating or managing ulcerative colitis, which comprises administering to a patient in need thereof a therapeutically effective amount of (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded May 5, 2026
From: OXFORD FINANCE LLC
To: LEXICON PHARMACEUTICALS, INC.; LEXICON PHARMACEUTICALS
Reel/Frame 075545/0601 →
SECURITY INTEREST Recorded Mar 17, 2022
From: LEXICON PHARMACEUTICALS, INC.
To: OXFORD FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 059432/0709 →
RELEASE OF SECURITY INTEREST Recorded Sep 14, 2020
From: BIOPHARMA CREDIT PLC
To: LEXICON PHARMACEUTICALS, INC.
Reel/Frame 053767/0445 →
SECURITY INTEREST Recorded Dec 20, 2017
From: LEXICON PHARMACEUTICALS, INC.
To: BIOPHARMA CREDIT PLC
Reel/Frame 044958/0377 →