IP Library Granted Patent US 8,946,450
Granted Patent B2
US 8,946,450 · App. 13/735,511 · Granted Feb 3, 2015

Composition, synthesis, and use of new substituted pyran and pterin compounds

Inventors: Partha Basu (Pittsburgh, PA); Igor Pimkov (Pittsburgh, PA)
Assignee: Duquesne University of the Holy Ghost
C07D475/04C07D409/04C07D487/04C07D495/04C07D495/14
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Quick Facts
Patent No.
US 8,946,450
App. No.
13/735,511
Granted
Feb 3, 2015
Kind
B2
Abstract

The present invention relates to substituted pterin compounds, their synthesis and use. In particular, the present invention relates to a new precursor compound and its analogs for synthesizing a new substituted pterin compound and its analogs. These new compounds are particularly suitable for treating molybdenum cofactor deficiency.

Claims (17)

1. A method for preparing a compound of structure I:

wherein X is selected from the group consisting of oxygen and sulfur and, R 1 and R 2 are each independently unsubstituted C 1 -C 6 alkyl,

comprising:

a. obtaining an acetylene compound of structure II:

wherein R 1 and R 2 are defined as above for structure I;

b. combining the compound of structure II with a hydroxyl protecting group which forms a compound of structure III:

wherein R 1 and R 2 are defined as above for structure I, and Y is a hydroxyl protecting group;

c. deprotonating the compound of structure III and condensing the compound of the structure III with ethyl 2,2-diethoxy acetate ester which forms a substituted acetylene compound of structure IV:

wherein R 1 and R 2 are defined as above for structure I, Et is ethyl, and Y is as defined above for structure III

d. combining the substituted acetylene compound of structure IV with sulfurating agent 4-phenyl-1,3-dithiolane-2-thione to form a dithiolene substituted compound of structure V:

wherein R 1 and R 2 are defined as above for structure I, and Et is as defined above for structure IV; and

e. deprotecting acetal in the compound of structure V to form the compound of structure I.

2. The method of claim 1 wherein the acetylene compound is 2-methyl-3-butyn-2-ol.

3. The method of claim 1 wherein step b further comprises catalyst.

4. The method of claim 3 wherein the catalyst comprises p-toluensulfonic acid.

5. The method of claim 1 wherein the hydroxyl protecting group in steps b and c is tetrahydropyran.

6. The method of claim 1 wherein the deprotecting of the acetal in the compound of structure V comprises combining the compound of structure V with trimethylsilyl trifluoromethane sulfonate.

Assignments (2)
CONFIRMATORY LICENSE Recorded Jul 17, 2017
From: DUQUESNE UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 043208/0773 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 7, 2013
From: BASU, PARTHA; PIMKOV, IGOR
To: DUQUESNE UNIVERSITY OF THE HOLY GHOST
Reel/Frame 029578/0930 →
Continuity (2)
Division 13072092 · Mar 25, 2011
Related Publication 20130310390A1 · Nov 21, 2013