US Patent No. 10,214,765

CELL-PERMEABLE PROBES FOR IDENTIFICATION AND IMAGING OF SIALIDASES


Patent No. 10,214,765
Issue Date February 26, 2019
Title Cell-permeable Probes For Identification And Imaging Of Sialidases
Inventorship Chi-Huey Wong, Rancho Santa Fe, CA (US)
Jim-Min Fang, Taipei (TW)
Yih-Shyun E. Cheng, Taipei (TW)
Chamg-Sheng Tsai, New Taipei (TW)
Assignee Academia Sinica, Taipei (TW)

Claim of US Patent No. 10,214,765

1. A compound of formula (I):
or a salt thereof,
wherein
F atom at the C3-position is axial or equatorial;
R1 is H or C1-6 alkyl;
R2 is OR2O, N3, N(R2N)2, or —NH(C?NH)NH2;
each instance of R2O is independently hydrogen, C1-6 alkyl, acyl, or a hydroxyl protecting group;
each instance of R2N is independently hydrogen, C1-6 alkyl, acyl, or an amine protecting group;
each instance of R3a and R3b is independently hydrogen, —C(?O)—R3r, or a hydroxyl protecting group;
each instance of R3r is C1-6 alkyl, aryl, heteroaryl, heterocyclyl, alkylaryl, alkylheteroaryl, or alkylheterocyclyl;
X is selected from the group consisting of —O—, —O(C?O)—, —NH—, —NH(C?O)—, —(C?O)NH—, —O(C?O)NH—, —O(C?S)NH—, —NH(C?O)NH—, and —NH(C?S)NH—;
R4 is H, C1-6 alkyl, or -L-Z;
Y is CF3, C1-6 alkyl or -L-Z;
each instance of L is independently selected from the group consisting of —(CH2)n—, —(CH2)nC?O—, —(CH2)nNH—, —(C?O)(CH2)n—, —(CH2)nNH(C?O)—, —(C?O)(CH2)nNH(C?O)—, —(CH2)nSCH2(C?O)—, and —(CH2CH2O)n—;
each instance of n is an integer from 1 to 8, inclusive;
each instance of Z is alkynyl, alkenyl, halogen, N(RN)2, ORO, SRS, or CO2RO;
each instance of RN is independently hydrogen, C1-6 alkyl, acyl, or an amine protecting group;
each instance of RO is independently hydrogen, C1-6 alkyl, acyl, or a hydroxyl protecting group;
each instance of RS is independently hydrogen, C1-6 alkyl, or a thiol protecting group;
provided that the compound is not of the formula

provided that when R4 is -L-Z, Y is C1-6 alkyl; and
provided that when Y is -L-Z, R4 is H or C1-6 alkyl.