US 11,673,855 B2
Voltage gated sodium channel imaging agents
Matthias Schoenberger, Charlestown, MA (US); and Jacob Hooker, Charlestown, MA (US)
Assigned to The General Hospital Corporation, Boston, MA (US)
Filed by The General Hospital Corporation, Boston, MA (US)
Filed on Aug. 5, 2021, as Appl. No. 17/395,356.
Application 17/395,356 is a continuation of application No. 16/477,257, granted, now 11,117,858, previously published as PCT/US2018/013287, filed on Jan. 11, 2018.
Claims priority of provisional application 62/445,045, filed on Jan. 11, 2017.
Prior Publication US 2022/0267254 A1, Aug. 25, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 231/12 (2006.01); C07C 237/04 (2006.01); A61K 51/04 (2006.01)
CPC C07C 231/12 (2013.01) [C07C 237/04 (2013.01); A61K 51/04 (2013.01); C07B 2200/05 (2013.01)] 20 Claims
 
1. A process of preparing a compound of Formula VIII:

OG Complex Work Unit Chemistry
or a salt thereof, comprising reacting a compound of Formula Ic:

OG Complex Work Unit Chemistry
with a compound of Formula IX:

OG Complex Work Unit Chemistry
in the presence of a base, wherein:
LG is a leaving group;
R1 is selected from the group consisting of H, C1-6 alkyl, and C1-6 haloalkyl;
each R3 is independently selected from the group consisting of halo, C1-6 alkyl, and C1-6 haloalkyl; and
n is an integer from 0 to 5.
 
5. A process of preparing a compound of Formula X:

OG Complex Work Unit Chemistry
or a salt thereof, comprising reacting a compound of Formula Ic:

OG Complex Work Unit Chemistry
with a compound of Formula IXa:

OG Complex Work Unit Chemistry
wherein:
LG is a leaving group;
R1 is selected from the group consisting of H, C1-6 alkyl, and C1-6 haloalkyl;
each R3 is independently selected from the group consisting of halo, C1-6 alkyl, and C1-6 haloalkyl; and
n is an integer from 0 to 5.
 
14. A process of preparing a compound of the following formula:

OG Complex Work Unit Chemistry
or a salt thereof, comprising reacting N-(2,6-dimethylphenyl)-2-(ethylamino)acetamide with 2-(fluoro-18F)ethyl 4-methylbenzenesulfonate, wherein the reacting is performed in a polar aprotic solvent.
 
17. A process of preparing a compound of the following formula:

OG Complex Work Unit Chemistry
or a salt thereof, comprising reacting N-(2,6-dimethylphenyl)-2-(ethylamino)acetamide with 1-bromo-2-(fluoro-18F)ethane in the presence of NaI, wherein the reaction is performed in a polar aprotic solvent.
 
18. A process of preparing a compound of the following formula:

OG Complex Work Unit Chemistry
or a salt thereof, comprising reacting N-(2,6-dimethylphenyl)-2-(ethylamino)acetamide with 1-(fluoro-18F)-2-iodoethane, wherein the reaction is performed in a polar aprotic solvent.