IP Library Granted Patent US 9,315,532
Granted Patent B2
US 9,315,532 · App. 11/920,909 · Granted Apr 19, 2016

Fatty acid carbohydrate hybrid molecules as therapeutic agents and methods thereof

Inventors: Kevin J. Yarema (Woodstock, MD); Srinivasa-Gopalan Sampathkumar (Towson, MD); Mark B. Jones (Baltimore, MD); Christopher T. Campbell (Baltimore, MD); Udayanath Aich (Baltimore, MD)
Assignee: The Johns Hopkins University
C07H1/00C07H5/04C07H5/06
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Quick Facts
Patent No.
US 9,315,532
App. No.
11/920,909
Granted
Apr 19, 2016
Kind
B2
Abstract

Described herein are fatty acid carbohydrate hybrid compounds and derivatives thereof, and methods of treating or preventing disease and disease symptoms using the compounds and compositions thereof.

Claims (28)

1. A compound of formula (I), or pharmaceutically acceptable salt,thereof:

wherein,

each R′ is independently is —C(O)(CH 2 ) 2-7 CH 3 ; and

R is selected from the group consisting of

CH 2 (CH 2 ) 1-4 COCH 3 ,

CH 2 (CH 2 ) 1 COCH 2 CH 3 ,

CH 2 N 3 ,

CH 2 OCOCH 3 ,

(CH 2 ) 1-3 SCOCH 3 ,

CH 2 Ph,

CH(CH 3 ) 2 ,

CH 2 CF 3 ,

(CH 2 ) 3 CH(CH 3 ) 2 , and

CH 2 CH═CH(CH 3 ).

2. The compound of claim 1 , wherein each R′ is —C(O)(CH 2 ) n CH 3 wherein n=2-4.

3. A pharmaceutical composition comprising a compound of Formula (I) in claim 1 and a pharmaceutically acceptable carrier.

4. The composition of claim 3 , further comprising an additional therapeutic agent.

5. A kit comprising an effective amount of a compound of Formula (I) in claim 1 in unit dosage form, together with instructions for administering the compound to a subject suffering from or susceptible to a cancer disease or disorder or symptoms thereof.

6. A method of treating a subject suffering from or susceptible to a disease or disorder, the method comprising the step of administering to the subject a therapeutic amount of a compound of Formula (I) in claim 1 sufficient to treat the disease or disorder or symptoms thereof under conditions such that the disease or disorder is treated.

7. A method of treating a subject suffering from or susceptible to a disease or disorder, the method comprising the steps of: (i) identifying the patient as in need of administration of a histone deacetylase inhibitor (HDACi) compound that activates sialic acid biosynthesis; and (ii) administering to the subject a therapeutic amount of a compound of Formula (I) in claim 1 sufficient to treat the disease or disorder or symptoms thereof under conditions such that the disease or disorder is treated.

8. A method of inducing apoptosis in a subject, the method comprising the steps of identifying a subject as in need thereof and administering to the subject a therapeutic amount of a compound of the formula (I) in claim 1 capable of inducing apoptosis.

9. A method of inducing apoptosis in a subject, the method comprising the steps of identifying a subject as in need thereof and administering to the subject a therapeutic amount of a compound of the formula (I) in claim 1 capable of inducing apoptosis and activating silalic acid biosynthesis.

10. The method of claim 6 , wherein the disease or disorder is not cancer.

11. A method of treating multiple sclerosis, Crohn's disease, rheumatoid arthritis, fibrosis, myocardial infarction, osteoid arthritis, Kaposi's sarcoma-associated herpes virus, Parkinson's disease, Huntington's disease, spinal muscular atrophy (increase survival motor neuron protein), cystic fibrosis, ulcerative colitis, antibiotic-associated diarrhea, stem cell fate and regenerative medicine, immune disorders, congenital abnormalities, infectious diseases and related diseases in a subject, the method comprising the steps of identifying a subject as in need thereof and administering to the subject a therapeutic amount of a compound of the of formula (I) in claim 1 sufficient to treat multiple sclerosis, Crohn's disease, rheumatoid arthritis, fibrosis, myocardial infarction, osteoid arthritis, Kaposi's sarcoma-associated herpes virus, Parkinson's disease, Huntington's disease, spinal muscular atrophy (increase survival motor neuron protein), cystic fibrosis, ulcerative colitis, antibiotic-associated diarrhea, stem cell fate and regenerative medicine, immune disorders, congenital abnormalities, infectious diseases and related diseases in a subject.

12. A method of sensitizing a cancer cell in a subject to anticancer agents, the method comprising the steps of identifying a subject as in need thereof and administering to the subject a therapeutic amount of a compound of formula (I) in claim 1 sufficient to sensitizing a cancer cell in a subject to anticancer agents.

13. A method of treating cancer in a subject, the method comprising the steps of administering to the subject a therapeutic amount of a compound of formula (I) in claim 1 .

14. A method of modulating gene expression in a subject, the method comprising the steps of identifying a subject as in need thereof and administering to the subject a therapeutic amount of a compound of formula (I) in claim 1 sufficient to modulate the protein.

15. A method of modulating sialyltransferase activity in a subject, the method comprising the steps of identifying a subject as in need thereof and administering to the subject a therapeutic amount of a compound of formula (I) in claim 1 sufficient to modulate the sialyltransferase activity.

Assignments (2)
CONFIRMATORY LICENSE Recorded Oct 30, 2017
From: JOHNS HOPKINS UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 044314/0880 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 15, 2009
From: YAREMA, KEVIN J.; SAMPATHKUMAR, SRINLVASA-GOPALAN; JONES, MARK B.; CAMPBELL, CHRISTOPHER T.; AICH, UDAYANATH
To: JOHNS HOPKINS UNIVERSITY, THE
Reel/Frame 022116/0635 →
Continuity (2)
Provisional Application 60683839 · May 24, 2005
Related Publication 20100144653A1 · Jun 10, 2010