US 12,110,270 B2
Systems and methods for generation of hyperpolarized materials
Ilai Schwartz, Neu-Ulm (DE); Michael Keim, Neu-Ulm (DE); and Stephan Knecht, Stuttgart (DE)
Assigned to NVision Imaging Technologies GmbH, Ulm (DE)
Filed by NVISION IMAGING TECHNOLOGIES GMBH, Ulm (DE)
Filed on Sep. 23, 2023, as Appl. No. 18/473,243.
Application 18/473,243 is a continuation of application No. PCT/IB2022/000160, filed on Mar. 23, 2022.
Claims priority of provisional application 63/266,986, filed on Jan. 21, 2022.
Claims priority of provisional application 63/260,631, filed on Aug. 27, 2021.
Claims priority of provisional application 63/164,585, filed on Mar. 23, 2021.
Prior Publication US 2024/0018087 A1, Jan. 18, 2024
Int. Cl. C07C 69/732 (2006.01); C07B 59/00 (2006.01); C07C 67/40 (2006.01)
CPC C07C 69/732 (2013.01) [C07B 59/001 (2013.01); C07C 67/40 (2013.01); C07B 2200/05 (2013.01)] 26 Claims
OG exemplary drawing
 
1. A composition comprising a compound of Formula (I):

OG Complex Work Unit Chemistry
wherein Z comprises: (i) a carbon-carbon double bond (—C═C—) which is substituted to include 1H (proton), 2H (deuterium), or a combination thereof, or (ii) a carbon-carbon triple bond (—C≡C—);
R1 comprises a parahydrogen induced polarization (PHIP) transfer moiety;
R2 comprises an optionally substituted hydrocarbon, alkoxy group, primary amine, secondary amine, or tertiary amine; and
R3 comprises a biorelevant imaging agent comprising a non-hydrogen nuclear spin and is at least partially isotopically labeled with the non-hydrogen nuclear spin;
wherein the PHIP transfer moiety comprises *CH2, *CH2—*CH2, *CHY, *C═Y, *CR4R5, *CR4Y, *C═Y, *CR6R7—* CR8R9, or any deuterated version thereof, wherein:
*C is a 12C or 13C carbon isotope;
R4 and R5 are each independently selected from: hydrogen, 1H, 2H, 3H, a linear, branched, or cyclic C1-C10 alkyl hydrocarbon, a C6 aryl, a benzyl, a phenyl, a heteroaryl, and a haloalkyl group;
Y is selected from: a spin-1/2 atom, and a spin-1/2 atom covalently bonded to one or more chemical moiety chosen from: a linear, branched, or cyclic C1-C10 alkyl hydrocarbon, a C6 aryl, benzyl, phenyl, heteroaryl, halogen or haloalkyl group, or a heteroatom selected from the group consisting of N, O, S, optionally substituted with a linear, branched, or cyclic C1-C10 alkyl hydrocarbon, a C6 aryl, benzyl, phenyl, heteroaryl, halogen or haloalkyl group; and
R6, R7, R8, and R9 are each independently selected from: 1H, 2H, 3H, a linear, branched, or cyclic C1-C10 alkyl hydrocarbon, a C6 aryl, a benzyl, a phenyl, a heteroaryl, and a haloalkyl group.