IP Library Granted Patent US 9,200,035
Granted Patent B2
US 9,200,035 · App. 14/352,891 · Granted Dec 1, 2015

Bifunctional compounds

Inventors: Peter Wipf (Pittsburgh, PA); Joel S. Greenberger (Sewickley, PA); Michael W. Epperly (Pittsburgh, PA); Melissa M. Sprachman (Pittsburgh, PA); Julie Pamela Goff (Pittsburgh, PA)
Assignee: University of Pittsburgh—of the Commonwealth System of Higher Education
C07K5/0812C07D205/04C07D305/06C07D405/12C07D405/14C07K5/06078
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Quick Facts
Patent No.
US 9,200,035
App. No.
14/352,891
Granted
Dec 1, 2015
Kind
B2
Abstract

A compound having the formula: wherein X is S, SO or SO 2 ; one of R 1 , R 2 , and R 3 is O and the others of R 1 , R 2 and R 3 are independently, the same or different, CH 2 , or CR 13 wherein, R 13 is an alkyl group, an alkenyl group, an alkynyl group, a trialkylsilyl group, or —(CH 2 ) m OR 15 , wherein R 15 is an alkyl group or an aryl group and m is an integer in the range of 1 to 10, and one of R 5 , R 6 , and R 7 is O and the others of R 5 , R 6 and R 7 are independently, the same or different, CH 2 , or CR 14 wherein, R 14 is an alkyl group, an alkenyl group, an alkynyl group, a trialkylsilyl group, or —(CH 2 ) n OR 16 , wherein R 16 is an alkyl group or an aryl group and n is an integer in the range of 1 to 10; R 4 and R 8 are independently, the same or different, H, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a C 1 -C 3 alkoxy group, an aryloxy group, or —(CH 2 ) q OR 17 , wherein R 17 is an alkyl group or an aryl group and q is an integer in the range of 1 to 10, provided that R 4 is not a C 1 -C 3 alkoxy group or an aryloxy group when R 1 or R 3 is O and R 8 is not a C 1 -C 3 alkoxy group or an aryloxy group when R 5 or R 7 is O; R 9 , R 10 , R 11 and R 12 are independently, the same or different, H, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group.

Claims (16)

1. A compound having the formula:

wherein X is S, SO or SO 2 ;

one of R 1 , R 2 , and R 3 is O and the others of R 1 , R 2 and R 3 are independently, the same or different, CH 2 , or CR 13 wherein, R 13 is an alkyl group, an alkenyl group, an alkynyl group, a trialkylsilyl group, or —(CH 2 ) m OR 15 , wherein R 15 is an alkyl group or an aryl group and m is an integer in the range of 1 to 10, and one of R 5 , R 6 , and R 7 is O and the others of R 5 , R 6 and R 7 are independently, the same or different, CH 2 , or CR 14 wherein, R 14 is an alkyl group, an alkenyl group, an alkynyl group, a trialkylsilyl group, or —(CH 2 ) n OR 16 , wherein R 16 is an alkyl group or an aryl group and n is an integer in the range of 1 to 10;

R 4 and R 8 are independently, the same or different, H, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a C 1 -C 3 alkoxy group, an aryloxy group, or —(CH 2 ) q OR 17 , wherein R 17 is an alkyl group or an aryl group and q is an integer in the range of 1 to 10, provided that R 4 is not a C 1 -C 3 alkoxy group or an aryloxy group when R 1 or R 3 is O and R 8 is not a C 1 -C 3 alkoxy group or an aryloxy group when R 5 or R 7 is O;

R 9 , R 10 , R 11 and R 12 are independently, the same or different, H, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group.

2. The compound of claim 1 wherein R 13 is a C 1 -C 3 alkyl group, a C 2 -C 3 alkenyl group, a C 2 -C 3 alkynyl group, or a trialkylsilyl group and R 14 is a C 1 -C 3 alkyl group, a C 2 -C 3 alkenyl group, a C 2 -C 3 alkynyl group, or a trialkylsilyl group.

3. The compound of claim 1 wherein one of R 9 and R 10 is H and one of R 11 and R 12 is H.

4. The compound of claim 1 wherein one of R 1 , R 2 , and R 3 is O and the others of R 1 , R 2 and R 3 are CH 2 , and one of R 5 , R 6 , and R 7 is O and the others of R 5 , R 6 and R 7 are CH 2 .

5. The compound of claim 1 wherein X is SO.

6. The compound of claim 1 wherein the compound has the formula:

7. The compound of claim 1 wherein R 2 and R 6 are each O; and R 1 , R 3 , R 5 , R 7 are each CH 2 .

8. The compound of claim 1 wherein R 2 and R 6 are each O; R 1 , R 3 , R 5 , R 7 are each CH 2 ; R 4 and R 8 are each C 1 -C 10 alkyl such as a methyl, ethyl, propyl, isopropyl, butyl, iso-butyl, sec-butyl, pentyl, 3-pentyl, or hexyl; and R 9 -R 12 are each H.

9. The compound of claim 1 wherein R 9 -R 12 are each H.

10. The compound of claim 1 wherein X is SO; R 2 and R 6 are each O; R 1 , R 3 , R 5 , R 7 are each CH 2 ; R 4 and R 8 are each C 1 -C 10 alkyl such as a methyl, ethyl, propyl, isopropyl, butyl, iso-butyl, sec-butyl, pentyl, 3-pentyl, or hexyl; and R 9 -R 12 are each H.

11. The compound of claim 1 wherein the compound has the formula

12. A composition comprising the compound of claim 1 , and a water soluble cosolvent.

Assignments (2)
CONFIRMATORY LICENSE Recorded Aug 3, 2015
From: UNIVERSITY OF PITTSBURGH
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 036245/0233 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2014
From: WIPF, PETER; GREENBERGER, JOEL S.; EPPERLY, MICHAEL W.; SPRACHMAN, MELISSA M.; GOFF, JULIE PAMELA
To: UNIVERSITY OF PITTSBURGH - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION
Reel/Frame 032721/0954 →
Continuity (3)
Provisional Application 61550114 · Oct 21, 2011
Provisional Application 61561030 · Nov 17, 2011
Related Publication 20140256654A1 · Sep 11, 2014