US 11,667,628 B2
Compounds for imaging tau proteins that accumulate in brain
Makoto Higuchi, Chiba (JP); Tetsuya Suhara, Chiba (JP); Masahiro Maruyama, Chiba (JP); Meiei Cho, Chiba (JP); and Hitoshi Shimada, Chiba (JP)
Assigned to NATIONAL INSTITUTES FOR QUANTUM AND RADIOLOGICAL SCIENCE AND TECHNOLOGY, Chiba (JP)
Filed by National Institutes for Quantum and Radiological Science and Technology, Chiba (JP)
Filed on Sep. 16, 2021, as Appl. No. 17/477,479.
Application 17/477,479 is a continuation of application No. 16/798,226, filed on Feb. 21, 2020, abandoned.
Application 16/798,226 is a continuation of application No. 14/346,914, granted, now 10,604,516, issued on Mar. 31, 2020, previously published as PCT/JP2012/083286, filed on Dec. 21, 2012.
Prior Publication US 2022/0056020 A1, Feb. 24, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 417/06 (2006.01); C07F 7/18 (2006.01); C07D 401/06 (2006.01); C07D 405/06 (2006.01); C07D 417/14 (2006.01); C07D 277/64 (2006.01); A61K 49/00 (2006.01); C07D 401/14 (2006.01); C07D 405/14 (2006.01)
CPC C07D 417/06 (2013.01) [A61K 49/0017 (2013.01); A61K 49/0021 (2013.01); C07D 277/64 (2013.01); C07D 401/06 (2013.01); C07D 401/14 (2013.01); C07D 405/06 (2013.01); C07D 405/14 (2013.01); C07D 417/14 (2013.01); C07F 7/1804 (2013.01)] 26 Claims
 
1. A method for imaging tau proteins that accumulate in the brain, the method comprising the steps of:
(a) administering to a mammal an effective amount of a compound of the Formula (I), or a pharmaceutically acceptable salt or a solvate thereof, and
(b) imaging the brain of the mammal,
wherein the compound of Formula (I) is:

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wherein:
R1 and R2 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, acyl, and hydroxyalkyl;
R3 is hydrogen or halogen;
ring A is a benzene ring or a pyridine ring;
ring B is selected from the group consisting of the following formulae (i), (ii), (iii), and (iv):

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in the formula (ii), Ra is alkyl;
R4 and R5 are each independently selected from the group consisting of hydrogen, hydroxy, alkoxy, haloalkoxy, halohydroxyalkoxy, and aminoalkyl; and

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 represents a double bona or a triple bond,
wherein the compound of Formula (I) is not:

OG Complex Work Unit Chemistry