IP Library Granted Patent US 10,370,395
Granted Patent B2
US 10,370,395 · App. 15/541,300 · Granted Aug 6, 2019

Cymanquine compounds and derivatives thereof and uses thereof

Inventors: William E. Geiger (Williston, VT); Kevin Lam (Genval, BE); Jon E. Ramsey (Richmond, VT); Claire F. Verschraegen (Burlington, VT)
Assignee: University of Vermont and State Agricultural College
C07F13/00A61K31/555A61K45/06
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Quick Facts
Patent No.
US 10,370,395
App. No.
15/541,300
Granted
Aug 6, 2019
Kind
B2
Abstract

Organometallic compounds comprising a chloroquinoline moiety and uses the compounds. The compounds are, for example, manganese or rhenium complexes of a ligand comprising a chloroquinoline moiety. The compounds can be used in, for example, methods of inhibiting cell growth.

Claims (16)

1. A compound having the formula:

where:

M is Mn or Re,

L is a neutral, two-electron donor ligand,

R 1 is an amine-substituted alkyl group,

R 2 is H, (CH 2 ) n CH 3 , wherein n is 0 to 20, OMe, OEt, OPh, Ph, CHO, COMe, COPh, CH 2 OH, CO 2 H, CO 2 Me, CO 2 Et, CH 2 Ph, NH 2 , NMe 2 , NEt 2 , C 6 H 4 Me, C 6 H 4 OMe, NH 2 COMe, F, Cl, Br, or I; and

E is a linker moiety connecting the cyclopentadienyl moiety with the chloroquinoline moiety.

2. The compound of claim 1 , wherein R 1 is (CH 2 ) n NR 3 R 4 , where n is an integer from 1 to 20 and R 3 and R 4 are independently H or an C 1 -C x alkyl group, wherein x is an integer from 2 to 20.

3. The compound of claim 1 , wherein L is selected from —CO, phosphines, phosphites, aryl amines, and carbenes.

4. The compound of claim 1 , wherein E is —NH(CH 2 ) n — or —NH(CH 2 ) n NHCH 2 —, wherein n is an integer from 1 to 10.

5. The compound of claim 1 , wherein a CO ligand is replaced by a second neutral, two-electron donor.

6. The compound of claim 1 , wherein M is Mn.

7. The compound of claim 1 , wherein M is Re.

8. The compound of claim 1 , wherein the compound has the following structure:

9. The compound of claim 1 , wherein the compound has the following structure:

10. A composition comprising one or more compounds of claim 1 and a pharmaceutical carrier.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 20, 2017
From: GEIGER, WILLIAM E.; LAM, KEVIN; RAMSEY, JON E.; VERSCHRAEGEN, CLAIRE F.
To: UNIVERSITY OF VERMONT AND STATE AGRICULTURAL COLLEGE
Reel/Frame 043052/0757 →
Continuity (2)
Provisional Application 62099335 · Jan 2, 2015
Related Publication 20180022771A1 · Jan 25, 2018