US 12,139,481 B2
Compositions comprising macrocycle derivatives incorporating bridged macrocycles and methods of producing and using same
Timothy J. Hubin, Weatherford, OK (US); M. O. Faruk Khan, Weatherford, OK (US); Stephen James Archibald, Hull (GB); and Babu Lal Tekwani, Oxford, MS (US)
Assigned to Southwestern Oklahoma State University, Weatherford, OK (US); and University of Mississippi, University, MS (US)
Filed by Southwestern Oklahoma State University, Weatherford, OK (US); and University of Mississippi, University, MS (US)
Filed on Oct. 20, 2020, as Appl. No. 17/075,167.
Application 17/075,167 is a division of application No. 15/753,409, granted, now 10,927,108, previously published as PCT/US2016/043165, filed on Jul. 20, 2016.
Claims priority of provisional application 62/206,023, filed on Aug. 17, 2015.
Prior Publication US 2021/0179606 A1, Jun. 17, 2021
Int. Cl. A61K 31/55 (2006.01); A61K 31/4985 (2006.01); A61K 31/4995 (2006.01); A61K 45/06 (2006.01); A61P 31/00 (2006.01); C07D 273/00 (2006.01); C07D 401/04 (2006.01); C07D 471/00 (2006.01); C07D 487/04 (2006.01); C07D 519/00 (2006.01); G01N 33/58 (2006.01); G01N 33/60 (2006.01); A61K 33/30 (2006.01); A61K 33/32 (2006.01); A61K 33/34 (2006.01); A61P 31/04 (2006.01); A61P 31/10 (2006.01)
CPC C07D 471/00 (2013.01) [A61K 31/4985 (2013.01); A61K 31/4995 (2013.01); A61K 31/55 (2013.01); A61K 45/06 (2013.01); A61P 31/00 (2018.01); C07D 273/00 (2013.01); C07D 401/04 (2013.01); C07D 487/04 (2013.01); C07D 519/00 (2013.01); G01N 33/582 (2013.01); G01N 33/60 (2013.01); A61K 33/30 (2013.01); A61K 33/32 (2013.01); A61K 33/34 (2013.01); A61P 31/04 (2018.01); A61P 31/10 (2018.01); G01N 2800/26 (2013.01); Y02A 50/30 (2018.01)] 20 Claims
 
1. A method of inhibiting the growth and/or activity of at least one microbe selected from at least one bacteria, at least one fungus, and at least one parasite, the method comprising the step of:
contacting the at least one microbe with a composition containing at least one macrocyclic ligand, the composition comprising a compound of Formula (II):
A1-J-A2  (II)
wherein each “A” is a macrocyclic ligand that is independently selected from the group consisting of Formulas (a)-(e), with the proviso that at least one “A” must come from Formulas (a)-(d):
(a) a tetradentate ethylene cross-bridged macropolycyclic rigid ligand with ring size 12-14 and having the structure:

OG Complex Work Unit Chemistry
(b) a tetradentate ethylene side-bridged macropolycyclic rigid ligand with ring size 12-15 and having the structure:

OG Complex Work Unit Chemistry
(c) a tetradentate propylene cross-bridged macropolycyclic rigid ligand with ring size 12-14 and having the structure:

OG Complex Work Unit Chemistry
(d) a pentadentate ethylene cross-bridged macropolycyclic rigid ligand having the structure:

OG Complex Work Unit Chemistry
and
(e) a tetradentate or pentadentate-macrocyclic ligand having the structure:

OG Complex Work Unit Chemistry
wherein, in Formulas (a)-(e):
each “R” is independently selected from the group consisting of H, alkyl, heteroalkyl, aryl, heteroaryl, alkylaryl, and heteroalkylaryl groups;
each “n” is an integer independently selected from 0, 1, and 2, completing the valence of the atoms to which the “R” moieties are covalently bonded;
each “z” is an integer independently selected from 0 and 1; and
each “t” is an integer independently selected from 1 and 2; and
and wherein “J” in Formula (II) is a linking m-, o-, or p-xylyl group.