US 12,433,962 B2
Probes for imaging b-amyloid and inhibition of β-amyloid aggregation
Benzhong Tang, Hong Kong (CN); Tianfu Zhang, Hong Kong (CN); and Wing Yip Lam, Hong Kong (CN)
Assigned to The Hong Kong University of Science and Technology, Hong Kong (CN)
Filed by The Hong Kong University of Science and Technology, Hong Kong (CN)
Filed on Oct. 26, 2022, as Appl. No. 18/049,670.
Claims priority of provisional application 63/274,945, filed on Nov. 3, 2021.
Prior Publication US 2023/0133226 A1, May 4, 2023
Int. Cl. A61K 49/00 (2006.01); A61P 25/28 (2006.01); C07D 405/06 (2006.01); C07D 409/06 (2006.01); C07D 417/06 (2006.01); G01N 33/58 (2006.01); G01N 33/68 (2006.01)
CPC A61K 49/0021 (2013.01) [A61P 25/28 (2018.01); C07D 405/06 (2013.01); C07D 409/06 (2013.01); C07D 417/06 (2013.01); G01N 33/582 (2013.01); G01N 33/6896 (2013.01); G01N 2333/4709 (2013.01); G01N 2800/2821 (2013.01)] 20 Claims
 
1. An aggregation-induced emission luminogen (AIEgen) having a Formula 1:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
m is a whole number selected from 1-4;
n for each instance is a whole number selected from 1-6;
p is a whole number selected from 1-4;
q is a whole number selected from 2-6;
A is a bond or a moiety having the structure:

OG Complex Work Unit Chemistry
Y is O, S, or —NR6—;
X is —O(C═O)— or —(R4)C═C(R4)—;
R1 for each instance is independently hydrogen, halide, cyano, nitro, —OR7, —SR7, —N(R7)2, —(C═O)R7, —(C═O)OR7, —(C═O)N(R7)2, —N(R7)(C═O)R7, —O(C═O)R7, —N(R7)(C═O)OR7, —O(C═O)N(R7)2, —SO2R7, —SO2N(R7)2, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, heteroaryl, or —(CH2)nZ;
R2 is a moiety having structure:

OG Complex Work Unit Chemistry
R3 is hydrogen or cyano;
R3 for each instance is independently hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, or heteroaryl;
R5 is hydrogen, halide, cyano, nitro, —OR7, —SR7, —N(R7)2, —(C═O)R7, —(C═O)OR7, —(C═O)N(R7)2, —N(R7)(C═O)R7, —O(C═O)R7, —N(R7)(C═O)OR7, —O(C═O)N(R7)2, —SO2R7, —SO2N(R7)2, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, heteroaryl, or —(CH2)nZ;
R6 is hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, or heteroaryl;
R7 for each occurrence is independently hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, heteroaryl, or —(CH2)2Z; or two instances of R7 taken together with the atom or atoms to which they are covalently bonded form a 3-7 membered cycloalkyl, or 3-7 membered heterocycloalkyl;
R8 for each instance is independently hydrogen, halide, cyano, nitro, —OR7, —SR7, —N(R7)2, —(C═O)R7, —(C═O)OR7, —(C═O)N(R7)2, —N(R7)(C═O)R7, —O(C═O)R7, —N(R7)(C═O)OR7, —O(C═O)N(R7)2, —SO2R7, —SO2N(R7)2, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, heteroaryl, or —(CH2)nZ;
R9 is alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, heteroaryl, —(CH2)qOH, or —(CH2)qNH2; Q is an anion; and
Z for each instance is independently halide, —C≡CH, —N3, —NCS, —NCO, —OR7, —SR7, —N(R7)2, —(C═O)R7, —(C═O)OR7, —(C═O)N(R7)2, —N(R7)(C═O)R7, —O(C═O)R7, —N(R7)(C═O)OR7, —O(C═O)N(R7)2, —SO2R7, —SO2N(R7)2, or N-maleimide.