IP Library Granted Patent US 9,593,136
Granted Patent B2
US 9,593,136 · App. 14/130,384 · Granted Mar 14, 2017

Compounds for inhibiting 1-deoxy-D-xylulose-5-phosphate reductoisomerase

Inventors: Helena I. Boshoff (Potomac, MD); Cynthia S. Dowd (Washington, DC); Emily R. Jackson (Springfield, VA); Kylene Kehn-Hall (Fredericksburg, VA); Richard E. Lee (Cordova, TN); Robin Lee (Cordova, TN); Geraldine San Jose (Mios, FR)
Assignees: The George Washington University; George Mason University; St. Jude Children's Research Hospital, Inc.; The United States of America, as Represented by the Secretary, Department of Health and Human Services
C07F9/4021A01N37/46A01N57/18A61K31/135A61K31/66C07F9/4018C12Q1/533G01N2500/04
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Quick Facts
Patent No.
US 9,593,136
App. No.
14/130,384
Granted
Mar 14, 2017
Kind
B2
Abstract

In particular, the compound is effective to inhibit Dxr in Mycobacterium tuberculosis (Mtb). The present invention relates to compounds having general formula (I) or (II) where X is an acidic group, such as carboxylate, phosphonate, sulfate, and tetrazole; Ar is a substituted or unsubstituted aromatic or heteroaromatic group; and n is 0, 1, 2, 3, or 4, preferably 2, 3, or 4. The compounds inhibits 1-deoxy-D-xylulose-5-phosphate reductoisomerase (Dxr), particularly Dxr in Mycobacterium tuberculosis (Mtb).

Claims (18)

1. A compound having the chemical structure of formula (II)

wherein X is 1) a carboxylate, phosphonate, sulfate, an ester thereof, or a salt thereof, or 2) a tetrazole; Ar is a substituted or unsubstituted aromatic or heteroaromatic group; and n is 0, 1, 2, 3, or 4,

wherein “n is 1” and

are not simultaneously satisfied.

2. The compound of claim 1 , wherein Ar is a phenyl or a heteroaromatic group.

3. A compound having the chemical structure of formula (II)

wherein X is 1) a carboxylate, phosphonate, sulfate, an ester thereof, or a salt thereof, or 2) a tetrazol; Ar is a substituted or unsubstituted aromatic or heteroaromatic group; and wherein n is 2, 3, or 4.

4. A compound having the chemical structure of formula (II)

wherein X is a phosphonate, an ester thereof, or a salt thereof; Ar is a substituted or unsubstituted aromatic or heteroaromatic group; and n is 0, 1, 2, 3, or 4, wherein “n is 1” and

are not simultaneously satisfied.

5. The compound of claim 1 , selected from the group consisting of:

6. A pharmaceutical composition comprising a compound having the chemical structure of formula (II)

wherein X is 1) a carboxylate, phosphonate, sulfate, an ester thereof, or a salt thereof, or 2) tetrazole; Ar is a substituted or unsubstituted aromatic or heteroaromatic group; and n is 0, 1, 2, 3, or 4, wherein “n is 1” and

are not simultaneously satisfied.

7. The composition of claim 6 , wherein Ar is a phenyl or a heteroaromatic group.

8. A pharmaceutical composition comprising a compound having the chemical structure of formula (II)

where X is 1) a carboxylate, phosphonate, sulfate, an ester thereof, or a salt thereof, or 2) a tetrazole; Ar is a substituted or unsubstituted aromatic or heteroaromatic group; wherein n is 2, 3, or 4.

9. A pharmaceutical composition comprising the compound of claim 5 .

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 6, 2015
From: BOSHOFF, HELENA INGRID
To: THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES
Reel/Frame 036795/0789 →
CONFIRMATORY LICENSE Recorded Dec 1, 2014
From: GEORGE WASHINGTON UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 034499/0559 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 11, 2014
From: DOWD, CYNTHIA; JACKSON, EMILY R.; SAN JOSE, GERALDINE
To: THE GEORGE WASHINGTON UNIVERSITY
Reel/Frame 033716/0658 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 11, 2014
From: LEE, RICHARD E.; LEE, ROBIN
To: ST. JUDE CHILDREN'S RESEARCH HOSPITAL, INC.
Reel/Frame 033716/0699 →
Continuity (2)
Provisional Application 61503736 · Jul 1, 2011
Related Publication 20140378418A1 · Dec 25, 2014